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Cas Database

616-38-6

616-38-6

Identification

  • Product Name:Dimethyl carbonate

  • CAS Number: 616-38-6

  • EINECS:210-478-4

  • Molecular Weight:90.0788

  • Molecular Formula: C3H6O3

  • HS Code:2920 90 10

  • Mol File:616-38-6.mol

Synonyms:Methyl carbonate ((MeO)2CO);Carbonic acid, dimethyl ester;Dimethyl carbonate [UN1161] [Flammable liquid];Carbonic acid,esters,dimethyl ester;Methyl Carbonate;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF

  • Hazard Codes:F

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapour

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Rinse and then wash skin with water and soap. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Esters and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Explosion: In case of fire: keep drums, etc., cool by spraying with water. Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. Use water spray to cool and disperse vapors and protect personnel. Control runoff and isolate discharged material for proper disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from strong oxidants. Well closed. Store in an area without drain or sewer access.Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Air sensitive.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Dimethyl Carbonate
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  • Product Description:Dimethyl Carbonate >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl Carbonate >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl Carbonate >98.0%(GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dimethyl carbonate Msynth plus. CAS 616-38-6, chemical formula (CH O) CO., Msynth plus
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dimethyl carbonate for synthesis. CAS 616-38-6, chemical formula (CH O) CO., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
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Relevant articles and documentsAll total 379 Articles be found

Direct synthesis of dimethyl carbonate from methanol and carbon dioxide over Ga2O3/Ce0.6Zr0.4O2 catalysts: Effect of acidity and basicity of the catalysts

Lee, Hye Jin,Park, Sunyoung,Song, In Kyu,Jung, Ji Chul

, p. 531 - 537 (2011)

Ce X Zr1-X O2 catalysts with different cerium content (X) (X = 0, 0.2, 0.4, 0.5, 0.6, 0.8, and 1.0) were prepared by a sol-gel method for use in the direct synthesis of dimethyl carbonate from methanol and carbon dioxide. Among these catalysts, Ce0.6Zr 0.4O2 was found to show the best catalytic performance. In order to enhance the acidity and basicity of Ce0.6Zr 0.4O2 catalyst, Ga2O3 was supported on Ce0.6Zr0.4O2 (XGa2O 3/Ce0.6Zr0.4O2 (X = 1, 5, 10, and 15)) by an incipient wetness impregnation method with a variation of Ga 2O3 content (X, wt%). Effect of acidity and basicity of Ga2O3/Ce0.6Zr0.4O2 on the catalytic performance in the direct synthesis of dimethyl carbonate was investigated using NH3-TPD and CO2-TPD experiments. Experimental results revealed that both acidity and basicity of the catalysts played a key role in determining the catalytic performance in the direct synthesis of dimethyl carbonate from methanol and carbon dioxide. Large acidity and basicity of the catalyst facilitated the formation of dimethyl carbonate. The amount of dimethyl carbonate produced over XGa2O 3/Ce0.6Zr0.4O2 catalysts increased with increasing both acidity and basicity of the catalysts. Among the catalysts tested, 5Ga2O3/Ce0.6Zr0.4O 2, which retained the largest acidity and basicity, showed the best catalytic performance in the direct synthesis of dimethyl carbonate from methanol and carbon dioxide. Graphical Abstract: In the direct synthesis of dimethyl carbonate (DMC) from methanol and carbon dioxide over Ga 2O3/Ce0.6Zr0.4O2 catalysts, the amount of DMC showed a volcano-shaped curve with respect to Ga2O3 content. The amount of DMC increased with increasing both acidity and basicity of the catalysts [Figure not available: see fulltext.]

Efficient fixation and conversion of CO2 into dimethyl carbonate catalyzed by an imidazolium containing tri-cationic ionic liquid/super base system

Chaugule, Avinash A.,Tamboli, Ashif H.,Kim, Hern

, p. 42279 - 42287 (2016)

The synthesis route used to prepare dimethyl carbonate from CO2 and methanol is a most attractive route from a green chemistry point of view. Herein, we systematically studied binary catalyst systems for the synthesis of dimethyl carbonate from CO2 and methanol. It was found that [GLY(mim)3][NTf2]3IL/DBU, [GLY(mim)3][NTf2]3/MTBD and [GLY(mim)3][NTf2]3/TBD are effective binary catalysts for the direct synthesis of DMC without the need of a dehydration system. In particular, the [GLY(mim)3][NTf2]3 IL/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) system was found to have 37% MeOH conversion and 93% DMC selectivity under mild reaction conditions. However, the tri-imidazolium salts were compatible with DBU for effective CO2 adsorption, possibly because of the reactive C(2)-H in the imidazolium ring. Furthermore, the [GLY(mim)3][NTf2]3 IL/DBU catalytic system could be easily recovered and reused three times without any obvious loss of catalytic activity. The catalytic reactivity of [GLY(mim)3][NTf2]3 IL/DBU for the synthesis of DMC was proved by its predictable mechanism on the basis of 13C NMR spectroscopy.

Triorganotin(iv) cation-promoted dimethyl carbonate synthesis from CO2 and methanol: Solution and solid-state characterization of an unexpected diorganotin(iv)-oxo cluster

?vec, Petr,Cattey, Hélène,R??i?ková, Zdeňka,Holub, Josef,R??i?ka, Ale?,Plasseraud, Laurent

, p. 8253 - 8260 (2018)

Two novel C,N-chelated organotin(iv) complexes bearing weakly coordinating carborane moieties were prepared by the reaction of the corresponding C,N-chelated organotin(iv) chloride (i.e. LCNR2SnCl, R = n-Bu (1) and Ph (2); LCN = 2-(N,N-dimethylaminomethyl)phenyl)) with monocarba-closo-dodecaborate silver salt (AgCB11H12; Ag·3). Both products of the metathesis, [LCN(n-Bu)2Sn]+[CB11H12]- (4) and [LCNPh2Sn]+ [CB11H12]- (5), respectively, were characterized by both multinuclear NMR spectroscopy and elemental analysis. The instability of 4 and 5 towards water is discussed. The solid-state structure of LCN(n-Bu)2SnOH·B(C6F5)3 (4a) as a model compound with a Sn-O(H)?B linkage is also reported. The evaluation of the catalytic activity of 4 and 5 was carried out within the direct synthesis of dimethyl carbonate (DMC) from methanol and CO2. While 5 was shown to be definitively inactive, presumably due to cleavage of the Sn-Ph bond, compound 4 exhibits a beneficial action, since it leads to an amount of DMC higher than the stoichiometry (nDMC/nSn(cat) = 1.5). In addition, the solid state structures of [BnNMe3]+[CB11H12]- (6) and [(n-Bu)20Sn10O2(OMe)6(CO3)2]2+·2[CB11H12]- (7), isolated as single-crystals and resulting from the recombination of 4 under the reaction conditions (methanol/CO2), were established by sc-XRD analyses within the term of this work as well. 6 and 7 were also fully characterized by IR spectroscopy, multinuclear NMR in solution and elemental analysis.

Zn/Fe mixed oxide: Heterogeneous catalyst for the synthesis of dimethyl carbonate from methyl carbamate and methanol

Wang, Dengfeng,Zhang, Xuelan,Gao, Yangyan,Xiao, Fukui,Wei, Wei,Sun, Yuhan

, p. 430 - 433 (2010)

A series of Zn-Fe-O mixed oxides were prepared for the synthesis of dimethyl carbonate (DMC) from methyl carbamate and methanol. X-ray diffraction revealed that zinc ferrite crystal phase appeared and changed with different Zn/Fe molar ratio. The DMC yield could reach 30.7% under suitable conditions. In addition, elemental chemical analysis and the reusability test indicated that these catalysts presented good stability.

Graphene oxide supported molybdenum cluster: First heterogenized homogeneous catalyst for the synthesis of dimethylcarbonate from CO2and methanol

Kumar, Subodh,Khatri, Om P.,Cordier, St??phane,Boukherroub, Rabah,Jain, Suman L.

, p. 3488 - 3494 (2015)

The octahedral molybdenum cluster-based compound, Cs2Mo6Bri8Bra6 was immobilized on graphene oxide (GO) by using a facile approach. High resolution transmission electron microscopy results revealed that molybdenum clusters were uniformly distributed on the GO nanosheets. Cs2Mo6Bri8Bra6 was attached to the GO support via chemical interaction between apical ligands of Mo6Bri8Bra6 cluster units and oxygen functionalities of GO, as revealed by XPS studies. The developed material was used for the synthesis of dimethyl carbonate by reduction of carbon dioxide. The synthesized catalyst, that is, GO-Cs2Mo6Bri8Brax, exhibited higher catalytic efficiency than its homogeneous analogue without using dehydrating agent. The catalyst was found to be efficiently recyclable without significant loss of catalytic activity.

Preparation and characterization of H3PW12O40/ZrO2 catalyst for carbonation of methanol into dimethyl carbonate

Chiang, Chao Lung,Lin, Kuen Song,Yu, Ssu-Han

, p. 3797 - 3811 (2018)

A H3PW12O40/ZrO2 catalyst for effective dimethyl carbonate (DMC) formation via methanol carbonation was prepared using the sol–gel method. X-ray photoelectron spectra showed that reactive and dominant (63%) W(VI) species, in WO3 or H2WO4, enhanced the catalytic performances of the supported ZrO2. The mesoporous structure of H3PW12O40/ZrO2 was identified by nitrogen adsorption–desorption isotherms. In particular, partial sintering of catalyst particles in the duration of methanol carbonation caused a decrease in the Brunauer–Emmett–Teller surface area of the catalyst from 39 to 19?m2/g. The strong acidity of H3PW12O40/ZrO2 was confirmed by the desorption peak observed at 415?°C in NH3 temperature-programmed desorption curve. At various reaction temperatures (T = 110, 170, and 220?°C) and CO2/N2 volumetric flow rate ratios (CO2/N2 = 1/4, 1/7, and 1/9), the calculated catalytic performances showed that the optimal methanol conversion, DMC selectivity, and DMC yield were 4.45, 89.93, and 4.00%, respectively, when T = 170?°C and CO2/N2 = 1/7. Furthermore, linear regression of the pseudo-first-order model and Arrhenius equation deduced the optimal rate constant (4.24 × 10?3?min?1) and activation energy (Ea = 15.54?kJ/mol) at 170?°C with CO2/N2 = 1/7 which were favorable for DMC formation.

Synthesis of dimethyl carbonate from methyl carbamate and methanol catalyzed by mixed oxides from hydrotalcite-like compounds

Wang, Dengfeng,Zhang, Xuelan,Zhao, Wenbo,Peng, Weicai,Zhao, Ning,Xiao, Fukui,Wei, Wei,Sun, Yuhan

, p. 427 - 430 (2010)

A series of mixed oxides calcined from hydrotalcite-like compounds with different cations were prepared and their catalytic activities were studied by the synthesis of dimethyl carbonate (DMC) from methyl carbamate and methanol. Among them, ZnFe mixed oxide possessed the best catalytic ability. Furthermore, the zinc-based mixed oxides as well as the corresponding hydrotalcite-like compounds were characterized by using ICP, TGA, CO2-TPD and N2 adsorption/desorption techniques.

Reaction of dibutyltin oxide with methanol under CO2 pressure relevant to catalytic dimethyl carbonate synthesis

Kohno, Kazufumi,Choi, Jun-Chul,Ohshima, Yoshihiro,Yili, Abulimiti,Yasuda, Hiroyuki,Sakakura, Toshiyasu

, p. 1389 - 1392 (2008)

Dibutyltin oxide (Bu2SnO)n (3) reacts with methanol to give the tetrabutyl(dimethoxy)stannoxane dimer (4). The presence of 2,2-dimethoxypropane under a CO2 pressure accelerates the reaction resulting in nearly quantitative yield. Complex 4 exhibits catalytic activity as high as that of {Bu2Sn(OMe)2}2 (1) in the dimethyl carbonate (DMC) synthesis from CO2 and methanol. These results indicate that the conversion of 3 to 4 occurs under catalytic DMC production conditions.

Effects of Mo promoters on the Cu-Fe bimetal catalysts for the DMC formation from CO2 and methanol

Zhou, Ying-Jie,Xiao, Min,Wang, Shuan-Jin,Han, Dong-Mei,Lu, Yi-Xin,Meng, Yue-Zhong

, p. 307 - 310 (2013)

The Mo-promoted Cu-Fe bimetal catalysts were prepared and used for the formation of dimethyl carbonate (DMC) from CO2 and methanol. The catalysts were characterized by X-ray diffraction (XRD), temperature programmed reduction (TPR), laser Raman spectra (LRS), energy dispersive spectroscopy (EDS) and temperature programmed desorption (TPD) techniques. The experimental results demonstrated that the Mo promoters can decrease the reducibility and increase the dispersion of Cu-Fe clusters. The concentration balance of base-acid sites can be readily adjusted by changing the Mo content. The moderate concentration balance of acid and base sites was in favor of the DMC formation. Under optimal experimental conditions, the highest methanol conversion of 6.99% with a DMC selectivity of 87.7% can be obtained when 2.5 wt% of Mo was loaded.

Graphene oxide immobilized copper phthalocyanine tetrasulphonamide: The first heterogenized homogeneous catalyst for dimethylcarbonate synthesis from CO2 and methanol

Kumar, Subodh,Kumar, Pawan,Jain, Suman L.

, p. 18861 - 18866 (2014)

The first successful synthesis of DMC directly from methanol and carbon dioxide using a heterogenized homogeneous graphene oxide immobilized copper phthalocyanine tetrasulphonamide catalyst in the presence of N,N′-dicyclohexylcarbodiimide (DCC) as a dehydrating agent is described. The presence of a dehydrating agent was found to be vital and in its absence the yield of DMC was found to be decreased significantly. Under the optimized reaction conditions, the maximum yield of DMC reaches up to 13.3%. Although the homogeneous copper phthalocyanine tetrasulphonamide catalyst provided a little higher yield of DMC (14.2%), the facile recovery and recycling ability of the heterogeneous catalyst make the developed method more attractive from environmental and economical viewpoints.

Synthesis of dimethyl carbonate from ethylene carbonate and methanol over nano-catalysts supported on CeO2-MgO

Jun, Jin Oh,Lee, Joongwon,Kang, Ki Hyuk,Song, In Kyu

, p. 8330 - 8335 (2015)

A series of CeO2(X)-MgO(1-X) (X = 0, 0.25, 0.5, 0.75, and 1.0) nano-catalysts were prepared by a co-precipitation method for use in the synthesis of dimethyl carbonate from ethylene carbonate and methanol. Among the CeO2(X)-MgO(1-X) catalysts, CeO2(0.25)-MgO(0.75) nano-catalyst showed the best catalytic performance. Alkali and alkaline earth metal oxides (MO = Li2O, K2O, Cs2O, SrO, and BaO) were then supported on CeO2(0.25)-MgO(0.75) by an incipient wetness impregnation method with an aim of improving the catalytic performance of CeO2(0.25)-MgO(0.75). Basicity of the catalysts was determined by CO2-TPD experiments in order to elucidate the effect of basicity on the catalytic performance. The correlation between catalytic performance and basicity showed that basicity played an important role in the reaction. Yield for dimethyl carbonate increased with increasing basicity of the catalysts. Among the catalysts tested, Li2O/CeO2(0.25)-MgO(0.75) nano-catalyst with the largest basicity showed the best catalytic performance in the synthesis of dimethyl carbonate.

Gas-phase oxycarbonylation of methanol for the synthesis of dimethyl carbonate using copper-based Supported Ionic Liquid Phase (SILP) catalysts

Schneider, Martin Johannes,Haumann, Marco,Stricker, Marion,Sundermeyer, Joerg,Wasserscheid, Peter

, p. 71 - 78 (2014)

Catalyst systems for the gas-phase oxycarbonylation of methanol often suffer from low catalyst activities and strong catalyst deactivation. In this work, the continuous gas-phase oxycarbonylation of methanol was realized by using Supported Ionic Liquid-Phase (SILP) catalysts. Copper(I) bromide dissolved in various ionic liquids and dispersed on Polymer-Based Spherical Activated Carbon (PBSAC) as supporting material was found to be an active catalyst. The poor activity and stability of copper halide catalysts reported in literature was substantially increased by the presence of ionic liquids. In particular, trioctylmethylammonium bromide in combination with a basic salt additive increased the activity of the CuBr catalyst and led to comparatively stable SILP catalyst operation reaching a total turnover number of 600 over 50 h time-on-stream.

The influence of halogen anions and N-ligands in CuXn/N-ligands on the catalytic performance in oxidative carbonylation of methanol

Mo, Wanling,Xiong, Hui,Hu, Jianglin,Ni, Youming,Li, Guangxing

, p. 576 - 580 (2010)

The catalytic properties of CuXn/N-ligands (X=Cl, Br and I; n = 1 or 2) in oxidative carbonylation ofmethanolwere investigated. It was found that the interaction of halogen anions, N-ligands and Cu (I) affected the catalytic performance of copper complex catalyst in the reaction, especially iodide anion and 1,10-phenanthroline (Phen). When CuI/Phen was used as a catalyst, the conversion of methanol was 42.6%, the selectivity to dimethyl carbonate was 99.2% and the TOF was 13.1 h-1 at an optimized conditions: CuI/Phen 0.2 mol l-1, 120 °C, 2 h, 2.4 MPa, PCO/PO2 = 2:1. Compared with the plain CuI catalyst, the catalytic activity of CuI/Phen increased about 36 times.When CuI/Phen catalystwas immobilized on polystyrene (PS), the heterogenized catalyst,CuI/Phen-NH-PS, also exhibited veryhigh catalytic activity in oxidative carbonylation. The CuI/Phen - NH - PS catalyst remained its high catalytic activity even after seven recycles. The average weight loss of CuI/Phen - NH - PS after reaction was less than 1.0%, and the leaching of copper was only about 0.15% in each recycling test. Copyright

A new redox strategy for low-temperature formation of strong basicity on mesoporous silica

Zhu, Li,Lu, Feng,Liu, Xiao-Dan,Liu, Xiao-Qin,Sun, Lin-Bing

, p. 10058 - 10061 (2015)

A redox strategy was designed to generate strong basicity on mesoporous silica by using the redox interaction of a precursor with methanol vapor. The formation of strongly basic sites was realized at 400 °C, which breaks the tradition of thermally induced decomposition that usually requires much higher temperatures (>600 °C).

Efficient ceria-zirconium oxide catalyst for carbon dioxide conversions: Characterization, catalytic activity and thermodynamic study

Kumar, Praveen,With, Patrick,Srivastava, Vimal Chandra,Gl?ser, Roger,Mishra, Indra Mani

, p. 718 - 726 (2017)

In this study, ceria-zirconia based catalysts (CeO2, ZrO2and Ce0.5Zr0.5O2) were synthesized by hydrothermal method and characterized by N2-sorption, X-ray diffraction (XRD), scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Acidity and basicity of synthesized catalysts were investigated by NH3[sbnd] and CO2[sbnd] temperature-programmed desorption (TPD). Brunauer-Emmett-Teller (BET) surface area of CeO2, Ce0.5Zr0.5O2and ZrO2were found to be 88, 117 and 70?m2?g?1and average crystallite sizes was 9.48, 7.09 and 9.45?nm, respectively. These catalysts were further used for direct conversion of CO2with methanol for the synthesis of dimethyl carbonate (DMC). DMC yield was found to be highly dependent upon the both basicity and acidity of catalysts. Ce0.5Zr0.5O2catalysts showed better activity as compared to CeO2and ZrO2catalysts. Effect of reaction conditions (such as catalyst dose, reaction temperature and reaction time) and catalyst reusability was studied with Ce0.5Zr0.5O2catalyst. The optimum operating condition for direct conversion of CO2into DMC at constant pressure of 150 bar were found to be reaction time?=?24?h, catalyst dose?=?1.25?g and temperature?=?120?°C. Moreover, chemical equilibrium modeling was performed using Peng–Robinson–Stryjek–Vera equation of state (PRSV-EoS) along with the van der Waals one-fluid (1PVDW) mixing rule to calculate the heat of reaction and Gibbs free energy change.

On the existence of the elusive monomethyl ester of carbonic acid [CH 3OC(O)OH] at 300 K: 1H- and 13C NMR measurements and DFT calculations

Dibenedetto, Angela,Aresta, Michele,Giannoccaro, Potenzo,Pastore, Carlo,Papai, Imre,Schubert, Gabor

, p. 908 - 913 (2006)

The elusive monomethyl ester of carbonic acid [CH3OC(O)-OH] has been prepared at 300 K by protonation of the sodium salt NaOC(O)OCH3 with anhydrous HCl or water and characterized by 1H- and 13C NMR spectroscopy. The stability of the acid and its reactivity towards hydroxo ions and methylating agents under ambient conditions are discussed. The energetics and the mechanism of the investigated reactions are examined on the basis of density functional calculations. For kinetic and thermodynamic reasons CH3OC(O)OH is unlikely to be formed by insertion of CO2 into the O-H bond of methanol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Carbon dioxide conversion to dimethyl carbonate: The effect of silica as support for SnO2 and ZrO2 catalysts

Ballivet-Tkatchenko, Danielle,Dos Santos, Jo?o H.Z.,Philippot, Karine,Vasireddy, Sivakumar

, p. 780 - 785 (2011)

Abundant in nature, CO2 poses few health hazards and consequently is a promising alternative to phosgene feedstock according with the principles of Green Chemistry and Engineering. The synthesis organic carbonates from CO2 instead of phosgene is highly challenging as CO2 is much less reactive. As part of our ongoing research on the investigation of catalysts for dimethyl carbonate (DMC) synthesis from methanol and CO 2, we herein report results aimed at comparing the catalytic behavior of new SnO2-based catalysts with that of ZrO2. Silica-supported SnO2 and ZrO2 exhibit turnover numbers which are an order of magnitude higher than those of the unsupported oxides. Tin-based catalysts also promote methanol dehydration which makes them less selective than the zirconium analogues. Last but not least, comparison with soluble Bu2Sn(OCH3)2 highlights the superiority of the organometallic precursor for achieving 100% selectivity to DMC but it deactivates by intermolecular rearrangement into polynuclear tin species.

Fixation of CO2by electrocatalytic reduction to synthesis of dimethyl carbonate in ionic liquid using effective silver-coated nanoporous copper composites

Wang, Xuan Yun,Liu, Su Qin,Huang, Ke Long,Feng, Qiu Ju,Ye, De Lai,Liu, Bing,Liu, Jin Long,Jin, Guan Hua

, p. 987 - 990 (2010)

With high surface area, open porosity and high efficiency, a catalyst was prepared and firstly employed in electrocatalytic reduction of CO2 and electrosynthesis of dimethyl carbonate (DMC). The electrochemical property for electrocatalytic reduction of CO2 in ionic liquid was studied by cyclic voltammogram (CV). The effects of various reaction variables like temperature, working potential and cathode materials on the electrocatalytic performance were also investigated. 80% yield of DMC was obtained under the optimal reaction conditions.

Dimethyl carbonate production via the oxidative carbonylation of methanol over Cu/SiO2 catalysts prepared via molecular precursor grafting and chemical vapor deposition approaches

Drake, Ian J.,Fujdala, Kyle L.,Bell, Alexis T.,Tilley, T. Don

, p. 14 - 27 (2005)

The influence of catalyst synthesis method and Cu source on the activity and selectivity of Cu/SiO2 catalysts for the gas-phase oxidative carbonylation of methanol to dimethyl carbonate (DMC) is reported. [CuOSi(O tBu)3]4, [CuO tBu]4, and CuCl were used as precursors to produce highly dispersed silica-supported copper. XANES and EXAFS characterization prior to reaction (but after thermal treatment under He) showed that Cu in the catalysts prepared with CuCl and [CuOSi(O tBu)3]4 was present primarily as isolated Cu(I) species, whereas [CuO tBu]4 produced 1-nm Cu particles. During the catalytic reaction, the Cu in catalysts prepared from CuCl and [CuOSi(O tBu)3]4 formed highly dispersed CuO moieties, whereas the Cu in catalysts prepared from [CuO tBu]4 formed a cuprous oxide layer over a Cu(0) core. For comparison, poorly dispersed Cu on silica was prepared via traditional incipient wetness impregnation with Cu(NO3)2. It was found that activity for DMC formation increased with increasing Cu dispersion. The selectivity for DMC formation (relative to CO) decreased with decreasing Cu dispersion when the original state of the Cu was Cu(0) directly preceding reaction conditions.

Transesterification of cyclic carbonates to dimethyl carbonate using solid oxide catalyst at ambient conditions: Environmentally benign synthesis

Sankar, Meenakshisundaram,Satav, Srikanth,Manikandan, Palanichamy

, p. 575 - 578 (2010)

Continuous synthesis at ambient conditions: Dimethyl carbonate (DMC) is an important methylating and carbonylating agent. Transesterification of cyclic carbonates using methanol for the synthesis of DMC is environmentally benign. CaO-ZnO catalysts, prepared by a wet impregnation method, are effective catalysts for the transesterification of ethylene carbonate using methanol in batch and in continuous reactors. Yields of ca. 84?% DMC can be achieved at ambient conditions.

Synthesis of dimethyl carbonate from propylene carbonate and methanol over Y2O3/CeO2-La2O3 catalysts

Song, Ji Hwan,Jun, Jin Oh,Kang, Ki Hyuk,Han, Seung Ju,Yoo, Jaekyeong,Park, Seungwon,Kim, Do Heui,Song, In Kyu

, p. 10810 - 10815 (2016)

A series of CeO2(1 - X)-La2O3(X) (X = 0, 0.05, 0.1, 0.15, and 0.2) mixed metal oxide catalysts with different La2O3 molar ratio (X) were prepared by a citric acid-assisted sol-gel method. The catalysts were applied to the synthesis of dimethyl carbonate (DMC) via transesterification of propylene carbonate with methanol. Among these catalysts, it was found that CeO2(0.85)-La2O3(0.15) catalyst showed the highest DMC yield. To improve the catalytic performance of CeO2(0.85)-La2O3(0.15), different amount of Y2O3 was introduced onto CeO2(0.85)-La2O3(0.15) by an incipient wetness impregnation method. The prepared XY2O3/CeO2(0.85)-La2O3(0.15) (X = 0, 3, 6, 9, 12, and 15 wt%) catalysts were then applied to the synthesis of DMC from propylene carbonate and methanol. Basicity of the catalysts was measured by CO2-TPD (temperature-programmed desorption) experiments to investigate the effect of basicity on the catalytic performance. A correlation between basicity and catalytic performance demonstrated that basicity of the catalyst played an important role in the transesterification of propylene carbonate with methanol. Yield for DMC increased with increasing basicity of the catalyst. Among the catalysts tested, 9Y2O3/CeO2(0.85)-La2O3(0.15) catalyst with the largest basicity showed the highest DMC yield.

A remarkable effect of alkali addition in the oxidative carbonylation of methanol to dimethyl carbonate catalyzed by a polymer-complexed Cu(II) catalyst system

Feng, Wei-Liang,Cao, Yong,Yi, Nan,Dai, Wei-Lin,Fan, Kang-Nian

, p. 958 - 959 (2004)

The presence of a small amount of alkali additive in the polymer-complexed copper catalysts can lead to a remarkable increase in the reaction efficiency for the oxidative carbonylation of methanol to dimethyl carbonate.

Oxidative carbonylation of methanol to dimethyl carbonate (DMC): a new catalytic system

Delledonne, Daniele,Rivetti, Franco,Romano, Ugo

, p. C15 - C19 (1995)

Oxidative carbonylation of methanol to dimethylcarbonate catalysed by cobalt complexes is reported.Cobalt complexes with oxygen and or nitrogen donor ligands such as carboxylate, acetylacetonate, picolinate and Schiff bases are suitable catalysts.The oxidative carbonylation of methanol catalysed by cobalt complexes which has never been reported, affords dimethylcarbonate with remarkably high selectivities.Of the cobalt complexes, those with Schiff bases show the highest reactivity.The influence of co-solvents was also examined.Keywords: Cobalt; Carbonylation; Methanol; Catalysis; Dimethyl carbonate

Structure of the active sites on H3Po4/ZrO2 catalysts for dimethyl carbonate synthesis from methanol and carbon dioxide

Ikeda, Yoshiki,Asadullah, Mohammad,Fujimoto, Kaoru,Tomishige, Keiichi

, p. 10653 - 10658 (2001)

The catalytic properties of H3PO4/ZrO2 catalysts for dimethyl carbonate (DMC) synthesis from CH3OH and CO2 were investigated. The modification of ZrO2 with H3PO4 promoted the activity for selective DMC formation. The characterization of H3PO4/ZrO2 catalysts was performed by means of BET, XRD, 31P MAS NMR, LRS, DRIFT, and NH3-TPD. From the characterization results, it was determined that ZrO2 had Lewis acid sites and did not have Br??nsted acid sites. The presence of Br??nsted acid sites as well as Lewis acid sites was observed on H3PO4/ZrO2 (P/Zr = 0.05). The acidity of the Br??nsted sites is weak, and the site's structure is a bridged OH. Furthermore, this Br??nsted site is formed by the interaction between tetragonal Zr and P. In the reaction scheme of DMC formation, the Br??nsted acid site can contribute to CH3OH activation and to the enhancement of the catalytic activity.

Graphene supported Cu nanoparticles as catalysts for the synthesis of dimethyl carbonate: Effect of carbon black intercalation

Shi, Ruina,Ren, Meijiao,Li, Haixia,Zhao, Jinxian,Liu, Shusen,Li, Zhong,Ren, Jun

, p. 257 - 268 (2018)

Reduced graphene oxide (rGO) intercalated with a carbon black (CB) supported copper catalyst (Cu/rGO-CB) was employed in the synthesis of dimethyl carbonate (DMC) via liquid-phase oxidative carbonylation of methanol. The conversion of methanol and the space-time yield of DMC (STYDMC) over Cu/rGO-CB reached 5.6% and 2757 mg/(g h), higher than over a Cu/rGO catalyst, 4.7% and 2334 mg/(g h), respectively. The characterization indicates that CB particles, acting as spacers, ensured the high utilization of graphene layers and enhanced the interaction between Cu and the support, and the oxygen containing groups on the surface of CB play an important role in stabilizing Cu clusters. In comparison with Cu/rGO, the loss of copper concentration in Cu/rGO-CB is significantly decreased, from 15.37% to 1.96%. Catalyst reusability tests show that Cu/rGO-CB could be reused five times without almost any catalytic activity loss, implying distinct enhanced catalytic stability compared to the Cu/rGO catalyst.

Facile synthesis of potassium tetrathiooxalate – The “true” monomer for the preparation of electron-conductive poly(nickel-ethylenetetrathiolate)

Tkachov, Roman,Stepien, Lukas,Roch, Aljoscha,Komber, Hartmut,Hennersdorf, Felix,Weigand, Jan J.,Bauer, Ingmar,Kiriy, Anton,Leyens, Christoph

, p. 2250 - 2254 (2017)

Herein, aiming at optimization of the polymerization process leading to a family of hole- and electron-conducting 1,1,2,2-ethenetetrathiolate-based polymers, such as poly(nickel-1,1,2,2-ethenetetrathiolate), poly[Kx(Ni-ett)], we investigated transformations of the monomer precursor 1,3,4,6-tetrathiapentalene-2,5-dione (TPD) occurring under polymerization conditions. We found that only one ring of TPD opens upon its reaction with potassium methoxide under inert conditions at room temperature which leads to the formation of potassium 2-oxo-1,3-dithiol-4,5-dithiolate (K2[3]). Heating of K2[3] under reflux in methanol solution under inert conditions opens the second ring, however the resulting product is not potassium ethenetetrathiolate (K4[2]), the product of an exhaustive methanolysis of TPD, but potassium tetrathiooxalate (K2[4]), the product of the decarbonylation of K2[3]. Preliminary experiments reveal that the involvement of K2[4] in the polymerization process is beneficial for reproducible formation of high quality 1,1,2,2-ethenetetrathiolate-based polymers suitable for thermoelectric applications.

Phosphinite-Ni(0) Mediated Formation of a Phosphide-Ni(II)-OCOOMe Species via Uncommon Metal-Ligand Cooperation

Kim, Yeong-Eun,Oh, Seohee,Kim, Seji,Kim, Onnuri,Kim, Jin,Han, Sang Woo,Lee, Yunho

, p. 4280 - 4283 (2015)

Reversible transformations are observed between a phosphide-nickel(II) alkoxide and a phosphinite-nickel(0) species via a P-O bond formation coupled with a 2-e- redox change at the nickel center. In the forward reaction, the nickel(0) dinitrogen species (PPOMeP)Ni(N2) (2) and {(PPOMeP)Ni}2(μ-N2) (3) were formed from the reaction of (PPP)NiCl (1) with a methoxy anion. In the backward reaction, a (PPP)Ni(II) moiety was regenerated from the CO2 reaction of 3 with the concomitant formation of a methyl carbonate ligand in (PPP)Ni(OCOOMe) (7). Thus, unanticipated metal-ligand cooperation involving a phosphide based ligand is reported.

Marsh, J. E.

, p. 2368 - 2370 (1914)

Synthesis of dimethyl carbonate from ethylene carbonate and methanol using TS-1 as solid base catalyst

Tatsumi,Watanabe,Koyano

, p. 2281 - 2282 (1996)

The titanium silicate molecular sieve, TS-1, exchanged with an aqueous solution of K2CO3 is an excellent heterogeneous catalyst for the synthesis of dimethyl carbonate by an ester exchange reaction between ethylene carbonate and methanol.

Dimethyl carbonate synthesis from carbon dioxide using ceria-zirconia catalysts prepared using a templating method: Characterization, parametric optimization and chemical equilibrium modeling

Kumar, Praveen,With, Patrick,Srivastava, Vimal Chandra,Shukla, Kartikeya,Gl?ser, Roger,Mishra, Indra Mani

, p. 110235 - 110246 (2016)

In this paper, a series of CexZr1-xO2 solid solution spheres were synthesized by exo- and endo-templating methods and tested for dimethyl carbonate (DMC) synthesis using direct conversion of CO2. The synthesized catalysts were characterized by X-ray diffraction (XRD), N2-physisorption, scanning electron microscopy (SEM), and CO2/NH3-temperature-programmed desorption (TPD). Formation of CexZr1-xO2 solid solutions with tetragonal and cubic crystal structures depending on cerium/zirconium compositions was confirmed by XRD analysis. The specific surface area of the mixed oxide decreased and the average pore diameter increased with an increase in the ceria content, with the exception of the mixed oxides with x = 0.4-0.5 i.e. Ce0.4Zr0.6O2 and Ce0.5Zr0.5O2. The basic and acidic site density of the synthesized catalysts was in the order: ZrO2 2 0.5Zr0.5O2, and the basic and acidic site density per unit area followed the same order. The best Ce0.5Zr0.5O2 catalyst was further used for the optimization of reaction conditions such as reaction time, reaction temperature, catalyst dose and reusability for DMC synthesis. Furthermore, study of chemical equilibrium modeling was done using the Peng-Robinson-Stryjek-Vera equation of state (PRSV-EoS) along with the van der Waals one-fluid reaction condition so as to calculate change of Gibbs free energy (ΔG°) and heat of reaction (ΔH°).

PREPARATION OF DIMETHYL CARBONATE FROM METHANOL AND CARBON DIOXIDE IN THE PRESENCE OF Sn(IV) and Ti(IV) ALKOXIDES AND METAL ACETATES

Kizlink, Juraj,Pastucha, Ivan

, p. 687 - 692 (1995)

The synthesis of dimethyl carbonate by the reaction of methanol with carbon dioxide in the presence of metal alkoxides and metal carboxylates was studied.The best results have been achieved with Ti(IV) and Sn(IV) alkoxides which at 130 to 180 deg C and low CO2 pressures yield dimethyl carbonate in 30 to 100 mole percent or 40 to 130 mole percent yields with respect to the metal alkoxides, depending on the carbon dioxide (gaseous and solid one, respectively).The yields can be further increased up to 70-190 mole percent and 90-270 mole percent, respectively, by the use of chemical scavengers of the reaction water.

Efficient, direct synthesis of dimethyl carbonate from CO2 using a solid, calcined zirconium phenylphosphonate phosphite catalyst

Unnikrishnan, Pulikkeel,Varhadi, Poonam,Srinivas, Darbha

, p. 23993 - 23996 (2013)

Direct synthesis of dimethyl carbonate (DMC) from CO2 and methanol with 100 mol% selectivity using a solid, reusable, hydrophobic, calcined zirconium phenylphosphonate phosphite catalyst is reported for the first time. DMC yield as high as 26 mmol g-1 catalyst correlated with the concentration of acid and base sites is obtained.

Spectro-Electrochemical Examination of the Formation of Dimethyl Carbonate from CO and Methanol at Different Electrode Materials

Figueiredo, Marta C.,Trieu, Vinh,Eiden, Stefanie,Koper, Marc T.M.

, p. 14693 - 14698 (2017)

In this work, we report a fundamental mechanistic study of the electrochemical oxidative carbonylation of methanol with CO for the synthesis of dimethyl carbonate on metallic electrodes at low overpotentials. For the first time, the reaction was shown to take place on the metallic catalysts without need of oxidized metals or additives. Moreover, in-situ spectroelectrochemical techniques were applied to this electrosynthesis reaction in order to reveal the reaction intermediates and to shed light into the reaction mechanism. Fourier transformed infrared spectroscopy was used with different electrode materials (Au, Pd, Pt, and Ag) to assess the effect of the electrode material on the reaction and the dependence of products and intermediates on the applied potentials. It was observed that the dimethyl carbonate is only formed when the electrode is able to decompose/oxidize MeOH to form (adsorbed) methoxy groups that can further react with CO to dimethyl carbonate. Furthermore, the electrode needs to adsorb CO not too strongly; otherwise, further reaction will be inhibited because of surface poisoning by CO.

Dehydrating agent effect on the synthesis of dimethyl carbonate (DMC) directly from methanol and carbon dioxide

Bernard, Franciele Longaray,Carmona da Motta Resende, Maria Angélica,Einloft, Sandra,Faria, Douglas José,Moreira dos Santos, Leonardo,Selbacch Pinto, Ingrid

, p. 34895 - 34902 (2020)

CO2emissions and global warming have increased with the growth of the world economy and industrialization. Direct synthesis of dimethyl carbonate (DMC) from CO2and methanol (CH3OH) has been considered a promising route from a green chemistry point of view due to global warming mitigation by CO2emission reduction. However, DMC yield, when obtained by direct synthesis, is limited due to unfavorable thermodynamics and catalyst deactivation by water formation in the reaction process. This problem motivated us to investigate the effect of dehydration on DMC production by direct synthesis. Herein, different dehydrating agents (2,2-dimethoxypropane, sodium sulfate, magnesium oxide and butylene oxide) were combined with molecular sieves to remove the water and minimize the reverse reaction. A new reactor presenting a compartment to accommodate molecular sieves in the gas phase was developed as well. The chemical/product analysis was carried out by gas chromatography and the results were used to calculate methanol conversion and DMC selectivity. The highest methanol conversion value was found for the combination of molecular sieves in the gas phase with 2,2-dimethoxypropane in the reaction liquid phase (methanol conversion = 48.6% and 88% selectivity). The results showed that dehydration systems may promote increased yield in direct DMC synthesis under mild conditions. The dehydration systems tested in this work exhibited excellent conversion and yield as compared to other reported studies.

La-modified mesoporous Mg-Al mixed oxides: Effective and stable base catalysts for the synthesis of dimethyl carbonate from methyl carbamate and methanol

Wang, Dengfeng,Zhang, Xuelan,Ma, Jie,Yu, Haiwen,Shen, Jingzhu,Wei, Wei

, p. 1530 - 1545 (2016)

A series of La-containing Mg-Al hydrotalcite-like (HTl) precursors with different La contents (Mg2+:Al3+:La3+ = 3:1:x, where x varies from 0 to 1.0) were synthesized using a co-precipitation method followed by hydrothermal treatment. X-ray diffraction and thermogravimetric measurements demonstrated that the yield of the HTl phase decreased with increasing La content. The La-modified Mg-Al mixed oxides (HTC-La) were then obtained by thermal decomposition of the corresponding HTl precursors, and the mesoporous structure was formed during calcination. It was demonstrated that the structure and surface basic properties of the HTC-La samples strongly depended on the amount of La additive. Simultaneously, the resulting HTC-La materials were used as solid base catalysts for the synthesis of dimethyl carbonate (DMC) from methyl carbamate (MC) and methanol. Then, the correlation between their basic properties and catalytic performance was studied in detail. The incorporation of a suitable amount of La into HTC-La catalysts was beneficial for the production of DMC, and a DMC yield of 54.3% with a high DMC selectivity of 80.9% could be achieved when x was tuned to 0.5 under the optimized reaction conditions. In addition, the HTC-La catalyst could be readily recycled while maintaining high catalytic activity and selectivity for DMC. Furthermore, in situ FTIR experiments were carried out to elucidate the adsorption behaviours of the reactants. On the basis of the experimental results, a plausible basic catalytic mechanism wherein MC and methanol were activated simultaneously on the basic sites of the catalyst was proposed for this catalytic reaction.

Kinetic study for the direct synthesis of dimethyl carbonate from methanol and CO2 over CeO2 at high pressure conditions

Santos,Pereira,Silva,Loureiro,Rodrigues

, p. 219 - 226 (2013)

The kinetics for the direct synthesis of dimethyl carbonate was studied over CeO2 at high pressure conditions in a batch reactor. Langmuir-Hinshelwood and Eley-Rideal mechanisms were proposed and compared by the performance of the respective reaction rate expression in fitting to the experimental kinetic data. The reactions were held at different temperatures (378-408 K), CO2/methanol molar ratios (1.1-4.0) and pressures (15-20 MPa) in order to adjust the kinetic parameters. An activation energy of 106 kJ mol-1, as well as the standard enthalpy and Gibbs energy of reaction (-20.10 and 31.50 kJ mol-1) were calculated from experiments. Furthermore, the changes in pressure revealed an effect on the kinetic constant, with an activation volume equal to -0.208 cm3 mol-1.

The promotion and stabilization effects of surface nitrogen containing groups of CNT on cu-based nanoparticles in the oxidative carbonylation reaction

Zhang, Guoqiang,Zhao, Dan,Yan, Junfen,Jia, Dongsen,Zheng, Huayan,Mi, Jie,Li, Zhong

, p. 18 - 29 (2019)

N-doped carbon nanotubes (NCNTs)with different contents of N were prepared by pre-oxidation and subsequent N-doping strategy and employed as the supports to fabricate Cu-based catalysts for oxidative carbonylation of methanol. The supports and their corresponding catalysts were characterized thoroughly by BET, XPS, XRD, H2-TPR, TEM, N2O chemisorption, CO-TPD, CH3OH-TPD and ICP-OES measurements. It is found that the increase of oxygen containing groups generated by pre-oxidation can effectively improve the content of the nitrogen containing groups during the subsequent N-doping process. The nitrogen containing groups, especially the pyridine N groups, serving as the preferred anchoring site, significantly promotes the dispersion of Cu species. With the increased content of N from 0 to 5.2%, the dispersion of Cu species increases from 11.0 to 21.6% and the space time yield of DMC increases from 150.5 to 1789.6 mg g?1h?1. Moreover, the incorporation of nitrogen containing groups enhances the interaction between Cu species and CNT support, which suppresses the auto-reduction of Cu2+ to Cu+ and Cu0, while improves the anti-agglomeration, anti-oxidation and anti-leaching properties of Cu species. From the perspective of stability, the space time yield of DMC for Cu/CNT decreases from 150.5 to 86.9 mg g?1 h?1 after four consecutive runs, while that of Cu/NCNT200 slightly decreases from 1789.6 to 1557.9 mg g?1 h?1, and the declined degrees are 42.3% and 12.9%, respectively. The superior dispersion, anti-agglomeration, anti-oxidation and anti-leaching properties of Cu species as well as the promotion effect of pyridine N groups are contributed to the increased activity and stability of the Cu/NCNT200 catalyst.

Synthesis of mesoporous carbon nitride: Via a novel detemplation method and its superior performance in base-catalyzed reactions

Xu, Jie,Wang, Yue,Shang, Jie-Kun,Jiang, Quan,Li, Yong-Xin

, p. 4192 - 4200 (2016)

A series of mesoporous graphitic carbon nitride materials have been synthesized using dicyandiamide as a precursor by a nanocasting method through a new detemplation process. Alkaline solutions could effectively eliminate hard siliceous templates, and ordered mesostructures have been well retained over the final synthesized CND materials. Fourier transform infrared and X-ray photoelectron spectroscopy characterization revealed that the employment of alkaline solution during the synthesis of the CND samples facilitated the condensation of tri-s-triazine fragments and thus enhanced the amount of bridging N species. According to the profiles of CO2 temperature programmed desorption and elemental analysis, the detemplating agent could not only preserve the original basic sites but also improve the overall basic intensity of the mesoporous CND samples. In base-catalyzed reactions, represented by Knoevenagel condensation and transesterification reactions, the mesoporous CND materials demonstrated excellent and stable catalytic performance, which is especially much higher than that of the mesoporous sample detemplated by traditional HF solution.

Template-derived carbon: An unexpected promoter for the creation of strong basicity on mesoporous silica

Sun, Lin-Bing,Liu, Xiao-Yan,Li, Ai-Guo,Liu, Xiao-Dan,Liu, Xiao-Qin

, p. 11192 - 11195 (2014)

Template-derived carbon is demonstrated to effectively promote the creation of strong basicity on mesoporous silica, for the first time. New materials owning ordered mesoporous structure, strong basicity, and excellent catalytic activity are thus successfully constructed at low temperatures, which are impossible to achieve using conventional methods.

Driving dimethyl carbonate synthesis from CO2 and methanol and production of acetylene simultaneously using CaC2

Zhang, Zhaofu,Liu, Shuaishuai,Zhang, Lujun,Yin, Shuai,Yang, Guanying,Han, Buxing

, p. 4410 - 4412 (2018)

The synthesis of dimethyl carbonate (DMC) from CO2 and methanol is a very interesting reaction, but is thermodynamically limited. In this work, CaC2 was used to consume the water produced in the reaction to shift the reaction equilibrium, and C2H2 was produced at the same time. This is the first work on the combination of driving a thermodynamically unfavorable reaction and producing C2H2 using CaC2.

Kinetics of dimethyl carbonate synthesis from methanol and carbon dioxide over ZrO2-MgO catalyst in the presence of butylene oxide as additive

Eta, Valerie,M?ki-Arvela, P?ivi,W?rn, Johan,Salmi, Tapio,Mikkola, Jyri-Pekka,Murzin, Dmitry Yu.

, p. 39 - 46 (2011)

A kinetic investigation of dimethyl carbonate (DMC) synthesis from methanol and CO2 over ZrO2-MgO was performed by using butylene oxide as a chemical trap for the water formed during the reaction. The effect of the catalyst amount, the stirring speed, the temperature, as well as the amount of butylene oxide on the reaction rate and the selectivity to DMC was studied. The analysis of the reaction pathway suggests that DMC and butylene glycol are formed via the reaction of adsorbed mono-methoxycarbonate intermediate and methoxybutanol or methanol. A kinetic model was developed based on the reaction mechanism and it was in agreement with the experimental data. The apparent activation energy for the formation of DMC was 62 kJ/mol.

ZrO2 Nanocrystals As Catalyst for Synthesis of Dimethylcarbonate from Methanol and Carbon Dioxide: Catalytic Activity and Elucidation of Active Sites

Akune, Takayuki,Morita, Yusuke,Shirakawa, Shinya,Katagiri, Kiyofumi,Inumaru, Kei

, p. 23 - 29 (2018)

The catalytic activity of zirconium oxide (ZrO2) nanocrystals for the reaction of carbon dioxide (CO2) with methanol to form dimethylcarbonate (DMC) was investigated. ZrO2 nanocrystals prepared by hydrothermal synthesis at various temperatures were compared. The size of the ZrO2 nanocrystals monotonically increased with the hydrothermal temperature, according to specific surface area, transmission electron microscope measurements, and their X-ray diffraction peak widths. The ZrO2 nanocrystals prepared by hydrothermal synthesis were found to exhibit high catalytic activity owing to their high surface area and catalytically active surfaces arising from their high crystallinity. Next, adsorbed species generated from CO2 on the ZrO2 surfaces were measured using CO2 temperature-programmed desorption (TPD) and in situ FT-IR spectroscopy. The results confirmed the presence of several kinds of adsorbed species including bidentate bicarbonate (b-HCO3-), bidentate carbonate (b-CO32-), and monodentate carbonate (m-CO32-). The relationship between the amounts of these surface species and the catalytic activity of the ZrO2 was investigated for the first time. The amount of the bidentate species (b-HCO3- and b-CO32-) was found to correlate well with the catalytic activity, demonstrating that the surface sites that afford these species contribute to the catalytic activity for this reaction.

Selective carbonylation of methanol to dimethyl carbonate by gas-liquid-solid-phase boundary electrolysis

Yamanaka, Ichiro,Funakawa, Akiyasu,Otsuka, Kiyoshi

, p. 448 - 449 (2002)

Selective and efficient electrochemical carbonylation of MeOH to DMC was performed over PdCl2/VGCF (vapor grown carbon fiber) anode by utilizing the three-phase boundary electrolysis at 1 atm (CO) and 298 K.

Dimethyl carbonate synthesis via transesterification of ethylene carbonate and methanol using ionic liquid catalysts immobilized on mesoporous cellular foams

Lee, Kwang-Hyeok,Lee, Seungjea,Shin, Dongil,Hahm, Hyun-Sik

, p. 109 - 121 (2016)

Dimethyl carbonate (DMC) was synthesized via transesterification of ethylene carbonate and methanol with ionic liquid catalysts. For this reaction, 1,4-diazobicyclo[2.2.2]octane (DABCO), [Choline]OH, and [BMIM]Cl were used as a homogeneous catalyst, and hydrotalcite, [DABCO]OH@MCF, [DABCO]Cl@MCF, and DABCO/MCF were used as a heterogeneous catalyst. To support the ionic liquids, mesoporous cellular foam (MCF) was prepared and characterized by SEM, TEM and BET surface area analyzer. The average cell and window sizes of the prepared MCF were 34.4 and 21.3 nm, respectively. The prepared MCF had a well structured three-dimensional structure. Among the homogeneous catalysts used, DABCO showed the highest DMC yield about 84 %, and among the heterogeneous catalysts, [DABCO]OH@MCF showed the highest DMC yield about 77 %. In the reusability test of the used catalysts, there was only 8 % point decrease in DMC yield with [DABCO]OH@MCF, whereas 58 percent point decrease in DMC yield with DABCO/MCF after four times recycling tests. The effects of an anion on the catalytic activity were investigated. The optimum reaction condition for DMC synthesis was also investigated with [DABCO]OH@MCF catalyst.

Synthesis of Dimethyl Carbonate by Electrolytic Carbonylation of Methanol in the Gas Phase

Otsuka, Kiyoshi,Yagi, Toshikazu,Yamanaka, Ichiro

, p. 495 - 498 (1994)

Electrolytic carbonylation of methanol has been attempted in the gas phase under atmospheric pressure at 343 K. The graphites added with PdCl2 and CuCl2 are favorable anodes for the synthesis of dimethyl carbonate (DMC). The formation of DMC occurs at a lower applied voltage than that for dimethoxy methane and methyl formate. However, a considerable CO2 formation accompanies the DMC formation.

Copper supported on N-heterocyclic carbene-functionalized porous organic polymer for efficient oxidative carbonylation of methanol

Lei, Yizhu,Fan, Meitao,Lan, Guosong,Li, Guangxing

, (2020)

A new heterogeneous catalyst for the oxidative carbonylation of methanol to dimethyl carbonate based on copper coordinated in N-heterocyclic carbene-functionalized porous organic polymer (Cu@PQP-NHC) was presented. The solid catalyst that featured relatively large surface area, hierarchical pore structure, and excellent swelling property, was prepared via a facile copolymerization reaction of tetra-vinylphosphonium salt and bis-vinylimidazolium salt, followed by successful immobilization of CuCl. Accordingly, the resulting Cu@PQP-NHC showed excellent catalytic performance for the oxidative carbonylation of methanol. A 10 mmol/l of Cu usage was sufficient for 9.3percent conversion of methanol with a high TOF number of 57 h?1. Importantly, the catalyst was easily recovered by simple centrifugation, and could be reused up to 10 consecutive recycles without obvious loss of its initial activity. Also, the solid catalyst showed negligible Cu leaching during the recycling, and 99percent Cu species was still retained after reusing 10 times. The results in this study highlights the advantages of porous organic polymer supported NHC-Cu catalyst as a highly active and stable heterogeneous catalyst, providing a promising route for the synthesis of dimethyl carbonate.

NiO/CeO2-ZnO nano-catalysts for direct synthesis of dimethyl carbonate from methanol and carbon dioxide

Kang, Ki Hyuk,Lee, Chang Hoon,Kim, Dong Baek,Jang, Boknam,Song, In Kyu

, p. 8693 - 8698 (2014)

XNiO/CeO2(0.7)-ZnO(0.3) (X =0, 1, 5, 10, and 15) nano-catalysts were prepared by a wet impregnation method with a variation of NiO content (X, wt%). The prepared catalysts were then applied to the direct synthesis of dimethyl carbonate from methanol and carbon dioxide. Successful formation of XNiO/CeO2(0.7)-ZnO(0.3) nano-catalysts was confirmed by XRD and ICP-AES analyses. Acidity and basicity of XNiO/CeO2-ZnO were measured by NH3-TPD (temperature-programmed desorption) and CO2-TPD experiments, respectively, with an aim of elucidating the effect of acidity and basicity of the catalysts on the catalytic performance in the reaction. It was revealed that the catalytic activity of XNiO/CeO2(0.7)-ZnO(0.3) was closely related to both acidity and basicity of the catalysts. The amount of dimethyl carbonate produced over XNiO/CeO2(0.7)-ZnO(0.3) increased with increasing acidity and basicity of the catalysts. Thus, both acidity and basicity of the catalysts played important roles in determining the catalytic performance in the direct synthesis of dimethyl carbonate from methanol and carbon dioxide.

Phosphoric acid intercalated Mg-Al hydrotalcite-like compounds for catalytic carboxylation reaction of methanol in a continuous system

Bougacha Ghorbel, Salwa,Medina, Francisco,Ghorbel, Abdelhamid,Segarra, Anna M.

, p. 142 - 148 (2015)

Mg-Al-hydrotalcite-like catalysts (HTlcs) with different amount of P/Mg molar ratio were prepared via co-precipitation method and calcined at 450 °C. The synthesized catalysts were tested in the direct-carboxylation reaction of methanol in gas phase in a continuous system such as chemical route for CO2 valorization. Activities around 2% with total selectivity towards the dimethyl carbonate (DMC) was obtained at moderate temperatures (150 °C) with both Mg/Al mixed oxides (HTO) and phosphated Mg/Al mixed oxides (HTc-9c). Even though the conversion increased until 16% at higher temperatures (200 °C), the selectivity with both catalysts (HTO and HTc-9c) decreased due to the decomposition of DMC to dimethyl ether (DME). Nevertheless, the catalyst with P showed less DMC decomposition and a higher selectivity towards the desired product. This is explained by the presence of orthophosphate species bonded to the Al3+ metals of the HTs (O-P(OAl)3) which give to the catalyst a higher structural stability and specific acid properties. In addition, the solids were characterized in-depth by XRD, ICP, NH3-TPD, FTIR, Raman, 27Al and 31P MAS NMR spectroscopy and SEM.

CuCl catalyst heterogenized on diamide immobilized SBA-15 for efficient oxidative carbonylation of methanol to dimethylcarbonate

Cao, Yong,Hu, Jun-Cheng,Yang, Ping,Dai, Wei-Lin,Fan

, p. 908 - 909 (2003)

CuCl has been successfully immobilized on a novel diamide modified SBA-15, and proven to be an efficient heterogenized catalyst for the oxidative carbonylation of methanol to dimethylcarbonate.

Utilization of environmentally benign dicyandiamide as a precursor for the synthesis of ordered mesoporous carbon nitride and its application in base-catalyzed reactions

Xu, Jie,Chen, Ting,Jiang, Quan,Li, Yong-Xin

, p. 3269 - 3277 (2014)

Assisted by a new dissolution procedure, dicyandiamide (DCDA), an environmentally benign and cheap precursor, has been employed for the synthesis of mesoporous carbon nitride (CN) materials through a nanocasting approach. The synthesized mesoporous materials possessed high specific surface areas (269-715 m2g-1) with narrow pore-size distributions (about 5 nm) and faithfully replicated the mesostructures of the SBA-15 and FDU-12 templates. Several characterization techniques, including XRD, SAXS, TEM, Raman and FTIR spectroscopy, XPS, and CO2-TPD, were used to analyze the physicochemical properties of these materials and the results showed that the mesoporous CND materials had graphitic-like structures and consisted of CN heterocycles, as well as amino groups. In a series of Knoevenagel condensation reactions, as exemplified by the reaction of various aldehydes and nitriles, these mesoporous CND materials demonstrated high and stable catalytic activities, owing to an abundance of basic sites.

Method for synthesizing dimethyl carbonate through transesterification

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Paragraph 0021-0028; 0031; 0032; 0033, (2021/07/31)

The invention relates to a method for synthesizing dimethyl carbonate through transesterification, and belongs to the technical field of chemical engineering. According to the method, propylene carbonate or ethylene carbonate and methanol are used as raw materials, guanidine salt ionic liquid is used as a catalyst, dimethyl carbonate is synthesized through transesterification, the use amount of the ionic liquid is 0.1%-5% of the total mass of methanol and propylene (or ethylene) carbonate, the reaction pressure is 50-200 kPa, the reaction temperature is 60-95 DEG C, and the reaction time is 0.5-4 h. The ionic liquid catalyst provided by the invention has good catalytic activity and can be recycled, and the method for producing dimethyl carbonate has the advantages of simple process flow, mild reaction conditions, environmental friendliness, low production cost and the like, and is a novel method for easily realizing industrial production.

The Influence of Iron Group Promoters on the Synthesis of Dimethyl Carbonate over CuY Catalysts Prepared via Modified Vapor Impregnation Method

Yuchun Wang,Liu, Zhaorong,Tan, Chao,Sun, Hong,Li, Zhong

, p. 705 - 712 (2021/04/22)

Abstract: CuY and CuMY (M = Fe, Co, Ni) catalysts were prepared by modified vapor impregnation using cupric acetylacetonate as copper source and M acetylacetonate as promoter. The catalysts were evaluated in heterogeneous catalytic vapor phase oxidative carbonylation of methanol to dimethyl carbonate (DMC). The catalyst samples were analyzed by XRD, H2-TPR, XPS, CO-TPD, and NH3?TPD, and their catalytic performance was assessed in a fixed-bed reactor. The experimental results indicate that all introduced species were well dispersed on zeolite Y, and the addition of iron group promoters have effect on the Cu+ contents, acidity and CO adsorption-desorption performance. Finally the influence of various promoters was examined with the aim of increasing space-time yield of DMC from methanol. Space-time yield of DMC was increased with the addition of iron group promoters in the order Fe? Co Ni, but the selectivity follows the order of Fe Ni Co, respectively.

Urea-Functionalized Swelling Poly(ionic liquid)s as Efficient Catalysts for the Transesterification and Hydrolysis of Ethylene Carbonate

Hu, Hao,Wang, Xin,Chen, Bihua,Gao, Guohua

, p. 3945 - 3952 (2021/07/31)

Urea-functionalized poly(ionic liquid)s (PILs) were synthesized through polymerization of urea tethered imidazolium ionic liquid monomers (urea-IL) with sodium acrylate, and N,N′-methylenebisacrylamide (MBA) as a crosslinker. Close-packed and interconnected pores (1–4 (Formula presented.)) under swollen state could be observed from the cryogenic scanning electron microscopy (cryo-SEM) images. The promising catalytic activity of the PILs was illustrated for the transesterification reaction of ethylene carbonate with methanol. High activity and selectivity could be achieved by using poly(urea-IL)-n catalysts, which was similar to that of corresponding homogeneous ionic liquid catalysts. The urea tethered imidazolium in PILs acted as hydrogen-bonding donor to activate ethylene carbonate and intermediate 2-hydroxyethyl methyl carbonate (HEMC) for enhancing catalytic activity. The swelling ability of urea-functionalized PILs in methanol enabled active urea sites accessible for substrates. However, the complete conversion of ethylene carbonate was limited by reversible reaction between ethylene carbonate and HEMC. A possible synergistic activation mechanism for the transesterification reaction was proposed and supported by NMR titrations. The catalyst can be reused and recycled five times with stable activity. Furthermore, urea-functionalized swelling PILs also exhibited high catalytic activity for the hydrolysis of ethylene carbonate.

One-step bulk fabrication of a CaO/carbon heterogeneous catalyst from calcium citrate for rapid synthesis of dimethyl carbonate (DMC) by transesterification of ethylene carbonate (EC)

Wei, Qiang,Zhang, Gang,Yao, Jie,Chen, Xuejun,Wang, Gongying,Yang, Xiangui

supporting information, p. 5540 - 5550 (2021/04/06)

Dimethyl carbonate (DMC) is well known as an extremely industrially valuable substance. The demand for high-efficiency synthesis of DMC has greatly driven the exploration of novel catalysts and their low-cost preparation methods. Herein, a novel method for the rapid batch preparation of CaO/carbon catalysts using calcium citrate (CaCi) was provided, and these catalysts were used to catalyze the transesterification reaction of methanol and ethylene carbonate (EC) to synthesize DMC and ethylene glycol (EG). Accordingly, the structure and properties of the catalysts were characterized using XRD, FTIR, N2adsorption-desorption, TG, TG-IR, CO2-TPD, XPS, SEM, TEM and ICP-OES techniques. Meanwhile, the effect of various process conditions such as carbonization temperature, reaction temperature, reaction time and catalyst amount has been extensively evaluated. Under the optimal process parameters, the conversion of EC and the selectivity of DMC and EG were 81.2, 99.3 and 99.5%, while the turnover number (TON) and turnover frequency (TOF) were 54.1 and 162 h?1, respectively. Furthermore, kinetic analysis was carried out, and the value ofk(reaction rate constant) was ≈0.159 mol L?1min?1. The reusability was also investigated.

Method for direct conversion of carbon dioxide to dialkyl carbonates using ethylene oxide as feedstock

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Page/Page column 17-20, (2021/03/11)

A method for co-production of high purity dimethyl carbonate and mono-ethylene glycol by applying a reactor, such as a membrane reactor and/or an adsorbent-catalytic reactor by capturing and reacting carbon dioxide with methanol and ethylene oxide. Carbon dioxide may be recovered from primary sources (utilities and industrial processes) by a membrane or solid adsorbent, and subsequently converted to an intermediate hydroxy-ethyl-methyl carbonate by reacting with ethylene oxide and methanol. For high-purity carbon dioxide (obtained by carbon capture technologies or from an ethanol fermentation process), the membrane reactor is replaced with a catalytic reactor for direct conversion of carbon dioxide to hydroxy-ethyl-methyl carbonate by reacting with ethylene oxide and methanol. The hydro-ethyl-methyl carbonate is further reacted with methanol for conversion to dimethyl carbonate. A combination of heterogeneous and homogeneous catalysts is implemented for an effective conversion of carbon dioxide. An integrated reactive distillation process using side reactors is used for facilitating catalytic reaction for production of high purity dimethyl carbonate.

Process route upstream and downstream products

Process route

C<sub>8</sub>H<sub>18</sub>N<sub>2</sub>O<sub>3</sub>Si
87580-31-2

C8H18N2O3Si

Trimethylmethoxysilane
1825-61-2

Trimethylmethoxysilane

C<sub>3</sub>H<sub>6</sub>N<sub>3</sub>O<sub>3</sub><sup>(1-)</sup>*K<sup>(1+)</sup>
135516-79-9

C3H6N3O3(1-)*K(1+)

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With potassium methanolate; tin(IV) chloride; dinitrogen pentoxide; Yield given. Multistep reaction; 1.) CH2Cl2, -15 deg C, 90 min, 2.) -40 deg C, 30 min;
C<sub>8</sub>H<sub>18</sub>N<sub>2</sub>O<sub>4</sub>Si
87580-29-8

C8H18N2O4Si

Trimethylmethoxysilane
1825-61-2

Trimethylmethoxysilane

C<sub>3</sub>H<sub>6</sub>N<sub>3</sub>O<sub>4</sub><sup>(1-)</sup>*K<sup>(1+)</sup>
135516-78-8

C3H6N3O4(1-)*K(1+)

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With potassium methanolate; tin(IV) chloride; dinitrogen pentoxide; Yield given. Multistep reaction; 1.) CH2Cl2, -20 deg C, 50 min, 2.) -40 deg C, 30 min;
methanol
67-56-1

methanol

C<sub>14</sub>H<sub>10</sub>ClN<sub>3</sub>O<sub>5</sub>

C14H10ClN3O5

4-chlorobenzamidoxime
5033-28-3

4-chlorobenzamidoxime

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With sodium methylate; at 25 ℃; Rate constant; also with 18-crown-6;
methanol
67-56-1

methanol

C<sub>15</sub>H<sub>13</sub>N<sub>3</sub>O<sub>5</sub>

C15H13N3O5

p-toluamidoxime
19227-13-5

p-toluamidoxime

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With sodium methylate; at 25 ℃; Rate constant; also with 18-crown-6;
methanol
67-56-1

methanol

C<sub>14</sub>H<sub>10</sub>ClN<sub>3</sub>O<sub>5</sub>

C14H10ClN3O5

3-chloro-N-hydroxy-benzamidine
22179-77-7

3-chloro-N-hydroxy-benzamidine

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With sodium methylate; at 25 ℃; Rate constant; also with 18-crown-6;
methanol
67-56-1

methanol

C<sub>15</sub>H<sub>13</sub>N<sub>3</sub>O<sub>6</sub>

C15H13N3O6

4-methoxybenzamidoxime
5373-87-5

4-methoxybenzamidoxime

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With sodium methylate; at 25 ℃; Rate constant; also with 18-crown-6;
methanol
67-56-1

methanol

C<sub>14</sub>H<sub>10</sub>N<sub>4</sub>O<sub>7</sub>

C14H10N4O7

m-nitrobenzamide oxime
5023-94-9

m-nitrobenzamide oxime

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With sodium methylate; at 25 ℃; Rate constant; also with 18-crown-6;
methanol
67-56-1

methanol

C<sub>14</sub>H<sub>10</sub>N<sub>4</sub>O<sub>7</sub>

C14H10N4O7

N'-hydroxy-4-nitrobenzimidamide
192332-48-2

N'-hydroxy-4-nitrobenzimidamide

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With sodium methylate; at 25 ℃; Rate constant; also with 18-crown-6;
methanol
67-56-1

methanol

C<sub>14</sub>H<sub>11</sub>N<sub>3</sub>O<sub>5</sub>

C14H11N3O5

N-hydroxybenzenecarboximidamide
613-92-3

N-hydroxybenzenecarboximidamide

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
With sodium methylate; at 25 ℃; Rate constant; also with 18-crown-6;
difluorocarbamoyl chloride
16847-30-6

difluorocarbamoyl chloride

sodium methylate
124-41-4

sodium methylate

tetrafluorohydrazine
10036-47-2

tetrafluorohydrazine

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
Conditions Yield
-106°C;
-106°C;

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