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4437-69-8 Usage

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4,4-Dimethyl-1,3-dioxolan-2-one (cas# 4437-69-8) is a compound useful in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 4437-69-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,4,3 and 7 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 4437-69:
(6*4)+(5*4)+(4*3)+(3*7)+(2*6)+(1*9)=98
98 % 10 = 8
So 4437-69-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O3/c1-5(2)3-7-4(6)8-5/h3H2,1-2H3

4437-69-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,4-dimethyl-1,3-Dioxolan-2-one

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:4437-69-8 SDS

4437-69-8Relevant articles and documents

Chemical fixation of CO2 to cyclic carbonate catalyzed by new environmental- friendly bifunctional bis-Β-cyclodextrin derivatives

Peng, Jing,Wang, Sheng,Yang, Hai-Jian,Ban, Binru,Wei, Zidong,Wang, Lihua,Bo, Lei

, p. 76 - 84 (2019)

In present work, three amino-bridged biomass bis-β-cyclodextrins (bis-β-CDs) and eight bifunctionalized bis-β-CDs derivatives were designed and synthesized as environmental friendly catalysts to fix CO2. Both the bridged bis-β-CDs 1a-3a/potassium halide and haloalkane functionalized bis-β-CDs 1b-8b were poven to be efficient catalytic systems for the solvent-free coupling reaction of CO2 and epoxides. After systematic investigation, the optimized conditions of (120 °C, 4 MPa, 0.14mol% 1a, 1.25mol% KI, 2 h) have been established for dual catalytic system 1a/KI and the excellent yield (94%) with high selectivity (99%) can be achieved for the cycloaddition of CO2 and propylene oxide. Furthermore, after functionalization with alkyl halides, bis-β-CD derivative 1b-8b as sigle bifunctional catalyst exhibited better activity under milder optimal conditions of (110 °C, 2 MPa, 0.125mol% 1b and 4 h). Moreover, these bifunctional catalysts are also applicable to a variety of epoxides (including diepoxides) and good catalytic performances were abtained for producing the corresponding cyclic carbonates in most cases. Furthermore, this catalyst can be reused at least for five times without significant activity decrease. Finally, a possible mechanism including the activation of both epoxide and CO2 was proposed based on the literatures and experimental results.

Metal-Organic Frameworks with Tb4 Clusters as Nodes: Luminescent Detection of Chromium(VI) and Chemical Fixation of CO2

Dong, Jie,Xu, Hang,Hou, Sheng-Li,Wu, Zhi-Lei,Zhao, Bin

, p. 6244 - 6250 (2017)

Two multifunctional metal-organic frameworks based on cubane-like tetrahedron Tb4 clusters as nodes have been synthesized and characterized. Compound 1 exhibits a 2D lanthanide-organic framework with Tb4 clusters as nodes, and compound 2 possesses a 3D framework with Tb4 clusters and Mn2+ as nodes. Interestingly, luminescent investigations on them reveal that the two compounds can act as recyclable luminescent probes for chromium(VI) anion species and the corresponding detection limit can reach 10-7 mol/L. Furthermore, 1 and 2 own efficient catalytic activity for the chemical fixation of CO2 with epoxides under mild conditions. Importantly, they both can be recycled at least three times without compromising the activity.

New lanthanide(iii) coordination polymers: Synthesis, structural features, and catalytic activity in CO2 fixation

Xu, Cong,Liu, Yan,Wang, Li,Ma, Jingxin,Yang, Lizi,Pan, Fu-Xin,Kirillov, Alexander M.,Liu, Weisheng

, p. 16426 - 16431 (2017)

A new series of lanthanide coordination polymers formulated as [Ln(μ-L)(μ3-L)(H2O)]nXn (Ln/X = Er/Cl (1), Er/Br (2), Tm/Cl (3), Tm/Br (4), Yb/Cl (5), and Yb/Br (6); L = 1,3-bis(4-carboxyphenyl) imidazolium carboxylate(1+)) were solvothermally generated and fully characterized. Single-crystal X-ray diffraction analysis shows that all products possess isomorphous structures that are composed of cationic 1D double chains with encapsulated halide anions. From a topological perspective, such 1D chains can be classified as a binodal 3,5-connected net with a unique topology defined by the point symbol of (3·42)(32·42·53·62·7). All products 1-6 feature a remarkable thermal stability and were applied as highly active heterogeneous catalysts for the coupling reactions between halogenated propylene oxides and CO2 to give the corresponding cyclic carbonates. The reaction conditions, substrate and catalyst scope, and mechanistic features of this catalytic transformation were investigated. High products yields (up to 98%), elevated TONs (up to 3920) or TOFs (up to 326 h-1) were attained under mild reaction conditions. In addition, catalyst 6 can be recycled at least eight times with no loss of catalytic activity.

Synthesis of carbonates from CO2 and epoxides catalyzed by the system of N-heterocyclic carbene, hydrogen bond donor, CrCl2, and tetrabutylammonium bromide

Zhang, Kuikui,Liu, Zhenbang,Liu, Ning

, (2021)

A three-component catalytic system including pyridine-bridged benzimidazolium salts, CrCl2, and tetrabutylammonium bromide (TBAB) was developed. Based on the control experiments and spectroscopic measurements, the role of the three components in the catalytic process was clarified, in which benzimidazolium salts were used as N-heterocyclic carbene precursor, a new Cr complex generating from the coordination of CrCl2 with pyridine nitrogen and pyrazole nitrogen bearing benzimidazolium salts was employed as hydrogen bond donor, TBAB was used as nucleophilic reagent, respectively. Under mild conditions (50°C and 1?bar CO2), the terminal epoxides displayed high reactivity in the three-component catalytic system. The catalytic system showed also high catalytic activity for the internal epoxides by increasing the temperature and CO2 pressure and/or prolonging the reaction time.

A Mechanochemical-Assisted Synthesis of Boron, Nitrogen Co-Doped Porous Carbons as Metal-Free Catalysts

Zhao, Li-Yuan,Dong, Xiao-Ling,Chen, Jun-Yue,Lu, An-Hui

, p. 2041 - 2050 (2020)

A green and convenient solid-state method assisted by mechanical energy is employed for the synthesis of boron (B) and nitrogen (N) co-doped porous carbons (B,N-Cs). Glutamic acid (Glu) and boric acid (H3BO3) are used as the N-containing carbon precursor and boron source, respectively. This method is easy to perform and proved to be efficient towards co-doping B and N into the carbon matrix with high contents of B (7 atom %) and N (10 atom %). By adjusting the molar ratio of H3BO3 to Glu, the surface chemical states of B and N could be readily modulated. When increasing H3BO3 dosage, the pore size of B,N-Cs could be tuned ranging from micropores to mesopores with a Brunauer–Emmett–Teller (BET) surface area up to 940 m2 g?1. Finally, the B,N-Cs were applied as metal-free catalysts for the cycloaddition of CO2 to epoxides, which outperform the N-doped carbon catalyst (NC-900) and the physically mixed catalyst of NC-900/B4C. The enhanced activity is attributed to the cooperative effect between B and N sites. X-ray photoelectron spectroscopy (XPS) analysis reveals that BN3 in the B,N-Cs serves as a critical active site for the cooperative catalysis.

Fixation of atmospheric CO2as C1-feedstock by nickel(ii) complexes

Mayilmurugan, Ramasamy,Muthuramalingam, Sethuraman,Velusamy, Marappan

, p. 7984 - 7994 (2021)

The development of molecular catalysts for the activation and conversion of atmospheric carbon dioxide (CO2) into a value-added product is a great challenge. A series of nickel(ii) complexes, [Ni(L)(CH3CN)3](BPh4)2,1-4of diazepane based ligands, 4-methyl-1-[(pyridin-2-yl-methyl)]-1,4-diazepane (L1), 4-methyl-1-[2-(pyridine-2-yl)ethyl]-1,4-diazepane (L2), 4-methyl-1-[(quinoline-2-yl)-methyl]-1,4-diazepane (L3) and 1-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl]-4-methyl-1,4-diazepane (L4), have been synthesized and characterized as catalysts for the activation of atmospheric CO2. The single-crystal X-ray structure of1shows a distorted octahedral geometry with acis-β configuration around the NiN6coordination sphere. All the complexes are used as catalysts for the conversion of atmospheric CO2and epoxides into cyclic carbonates at 1 atmosphere (atm) pressure and in the presence of Et3N. Catalyst4was found to be the most efficient catalyst and showed a 31% formation of cyclic carbonates with a TON of 620 under 1 atm air as the CO2source. This yield was enhanced to 94% with a TON of 1880 under 1 atm pure CO2gas and it is the highest catalytic efficiency known for nickel(ii)-based catalysts. Catalyst4enabled the transformation of a wide range of epoxides (eight examples) into corresponding cyclic carbonates with excellent selectivity (>99%) and yields of 59-94% and 11-31% under pure CO2and atmospheric CO2, respectively. The catalytic efficiency is strongly influenced by the electronic nature of the complexes. The CO2fixation reactions without an epoxide substrate led to the formation of the carbonate bridged dinuclear nickel(ii) complexes [(LNiII)2CO3](BPh4)21a-4a, which are speculated as catalytically active intermediates. The formation of these species was accompanied by the formation of new absorption bands around 592-681 nm and was further confirmed by the ESI-MS and IR spectral studies. The molecular structures of these carbonate-bridged key intermediates were determined by X-ray analysis. The structures contain two Ni2+-centers bridgedviaa carbonate ion that originated from CO2. Distorted square pyramidal geometries are adopted around each Ni(ii) center. All these results support that CO2fixation reactions occurviaCO2-bound nickel key intermediates.

DIASTEREOSELECTIVE FORMATION OF CYCLIC CARBONATES BY CYCLIZATION OF ALKENYLOXYCARBONYLOXY RADICALS

Beckwith, Athelstan L. J.,Davison, G. E.

, p. 49 - 52 (1991)

The alkenyloxycarbonyloxy radical (8) derived from trans-hex-2-en-1-ol via the N-hydroxypyridin-2-thione carbonate (4) undergoes fast (kc > 4.0 x 108 s-1 at 80 deg C) cyclization exclusively in the exo mode to give a cyclic radical (9) which is converted into products (6, 7) by diastereoselective SH2 reactions; radicals derived from homoallylic alcohols behave similarly.

Availability of other aliphatic polycarbonates derived from geometric isomers of butene oxide and carbon dioxide coupling reactions

Darensbourg, Donald J.,Chung, Wan-Chun

, p. 4943 - 4948 (2014)

In this study, we investigate the selectivity for copolymer versus cyclic carbonate production from the coupling of isomeric forms of butene oxide with carbon dioxide in the presence of binary and bifunctional cobalt(III) and chromium(III) salicylaldimine catalysts. Use of the less problematic 1-butene oxide has previously been reported to preferentially afford copolymer from its coupling with CO2. Of the epoxides, cis- and trans-2-butene oxide and isobutene oxide, only cis-2-butene oxide was shown to selectively provide polycarbonate, with both cobalt(III) catalysts being more effective than their chromium(III) analogues. The binary chromium catalyst system produced both cis- and trans-cyclic carbonates from the cycloaddition of CO2 and cis-2-butene oxide, whereas, the corresponding cobalt(III) catalyst selectively yielded 75.4% copolymer at 40 °C with the remaining product being trans-cyclic carbonate. In this instance, the trans-cyclic carbonate results from copolymer degradation, consistent with the observation that depolymerization of the copolymer derived from CO2 and cis-2-butene oxide affords trans-cyclic carbonate exclusively. By way of contrast, both bifunctional catalysts were efficient at producing copolymers with selectivities of 100% (40 °C) and 79% (70 °C) for the cobalt and chromium catalysts, respectively. The glass transition temperature (Tg) of poly(trans-2-butene carbonate) derived from the completely alternating copolymerization of CO2 and cis-2-butene oxide was found to be 68 °C, some 30 deg higher than poly(propylene carbonate). Furthermore, it was shown to have a significantly lower % elongation-to-break value than poly(propylene carbonate).

Polar group and defect engineering in a metal-organic framework: Synergistic promotion of carbon dioxide sorption and conversion

Jiang, Zhuo-Rui,Wang, Hengwei,Hu, Yingli,Lu, Junling,Jiang, Hai-Long

, p. 878 - 885 (2015)

Abstract A sulfone-functionalized metal-organic framework (MOF), USTC-253, has been synthesized that exhibits a much higher CO2 uptake capacity (168-182 %) than the corresponding unfurnished MOFs. The introduction of trifluoroacetic acid (TFA) during the synthesis of USTC-253 affords defect-containing USTC-253-TFA with exposed metal centers, which has an increased CO2 uptake (167 %) compared to pristine USTC-253. USTC-253-TFA exhibits a very high ideal adsorption solution theory selectivity (S=75) to CO2 over N2 at 298K. In addition, USTC-253-TFA demonstrates good catalytic activity and recyclability in the cycloaddition of CO2 and epoxide at room temperature under 1bar CO2 pressure as a result of the presence of Lewis and Bronsted acid sites, which were evaluated by diffuse reflectance infrared Fourier transform spectroscopy with a CO probe molecule. We propose that the CO2 adsorption capability has a positive correlation with the catalytic performance toward CO2 conversion.

8-Hydroxyquinolates of trivalent metals as new catalysts for the reaction of CO2 with epoxides

Lermontov, S. A.,Velikokhat'ko, T. N.,Golovin, E. Yu.,Zavel'skii, V. O.

, p. 836 - 838 (2002)

Tris(8-hydroxyquinolates) of aluminum(III), chromium(III), and iron(III) in the presence of triphenylphosphine oxide efficiently catalyze the formation of alkylenecarbonates by the reaction of CO2 with oxiranes, viz., propylene oxide, but-2-ene oxides, and isobutylene oxide. The catalytic system is active at 140-170 deg C and a CO2 pressure of 15-100 atm.

Cooperative calcium-based catalysis with 1,8-diazabicyclo[5.4.0]-undec-7-ene for the cycloaddition of epoxides with CO2 at atmospheric pressure

Liu, Xi,Zhang, Shuai,Song, Qing-Wen,Liu, Xiao-Fang,Ma, Ran,He, Liang-Nian

, p. 2871 - 2876 (2016)

A bifuncational catalytic system consisting of CaBr2 and 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) was developed for the efficient fixation of CO2 with epoxides to cyclic carbonates. Such a dual catalysis facilitates the reaction to proceed smoothly at atmospheric CO2 pressure, presumably due to the simultaneous activation of CO2 by DBU and epoxides by CaBr2. In addition, the activation role of CaBr2 was also studied using density functional theory (DFT) calculations. A plausible mechanism involving the DBU-CO2 adduct-assisted ring opening path and the bromide anion-promoted ring opening path is proposed, in combination with the activation of epoxides by the calcium cation. This process represents a simple, cost-effective and biocompatible route to obtain cyclic carbonates from CO2 under mild conditions, especially at atmospheric CO2 pressure.

Boron-doped melamine-derived carbon nitrides tailored by ionic liquids for catalytic conversion of CO2 into cyclic carbonates

Su, Qian,Yao, Xiaoqian,Cheng, Weiguo,Zhang, Suojiang

, p. 2957 - 2965 (2017)

A new approach to tailoring edge active groups of graphitic carbon nitrides for catalytic conversion of CO2 into cyclic carbonates was proposed in this work. To improve the catalytic performance, boron-doped melamine-derived graphitic carbon nitrides (MCNB) with numerous exposed edge defects were prepared by using 1-butyl-3-methylimidazolium tetrafluoroborate (BmimBF4) as the soft template and boron source. Different mass ratios of BmimBF4 to melamine were explored for MCNB preparation, MCNB(x) (x is the mass ratio) with different polymerization degree, pore structure and boron doping content were obtained, and the relationship between MCNB properties and the corresponding catalytic activity was then investigated. With low polymerization degree, abundant meso-macroporous structure and small amounts of boron (1.59 atm%) doped in the skeleton, MCNB(0.01) exhibited better catalytic performance and could be suitable for various epoxide substrates with the yield of cyclic carbonates up to 89.0% at 130°C in 6 h. According to the XPS analysis and DFT calculation results, the active centers were confirmed to be the partially-condensed amino groups in edge defects, which were enhanced by moderate doping of boron in the skeleton.

Nano-sized polydopamine-based biomimetic catalyst for the efficient synthesis of cyclic carbonates

Yang, Zifeng,Sun, Jian,Liu, Xiaomin,Su, Qian,Liu, Ying,Li, Qian,Zhang, Suojiang

, p. 3239 - 3243 (2014)

Polydopamine (PDA) is a biocompatible and biomimetic material. Herein, nano-sized PDA sphere was prepared and the combination of alkali metal halide and PDA was investigated as a catalyst for the synthesis of cyclic carbonates from epoxide and carbon dioxide. It was found that the activity of PDA could be obviously enhanced in the presence of alkali metal salts. After reaction, the catalyst and the products could be separated easily, and the catalyst was reusable. The origin of the high catalytic efficiency and the reaction mechanism were also discussed.

Radii-dependent self-assembly polynuclear lanthanide complexes as catalysts for CO2transformation into cyclic carbonates

Chen, Changjuan,Zhang, Aijiang

, p. 20155 - 20163 (2021/12/02)

Multidentate acylhydrazone ligand dinuclear and pentanuclear complexes were constructed with the lighter lanthanide ions (La3+, Pr3+, and Eu3+) and the heavier lanthanide ions (Tb3+ and Er3+), respectively, which indicated the structural change of polynuclear lanthanide complexes is controlled by the ionic radii of Ln3+ ions. In addition, these polynuclear lanthanide complexes as catalysts in combination with tetrabutylammonium bromide (TBAB) as a co-catalyst displayed excellent catalytic performance for CO2 conversion to obtain cyclic carbonates with a wide scope of substrates and high selectivity under solvent-free conditions. This journal is

Catalytic, Kinetic, and Mechanistic Insights into the Fixation of CO2 with Epoxides Catalyzed by Phenol-Functionalized Phosphonium Salts

Hu, Yuya,Wei, Zhihong,Frey, Anna,Kubis, Christoph,Ren, Chang-Yue,Spannenberg, Anke,Jiao, Haijun,Werner, Thomas

, p. 363 - 372 (2020/11/30)

A series of hydroxy-functionalized phosphonium salts were studied as bifunctional catalysts for the conversion of CO2 with epoxides under mild and solvent-free conditions. The reaction in the presence of a phenol-based phosphonium iodide proceeded via a first order rection kinetic with respect to the substrate. Notably, in contrast to the aliphatic analogue, the phenol-based catalyst showed no product inhibition. The temperature dependence of the reaction rate was investigated, and the activation energy for the model reaction was determined from an Arrhenius-plot (Ea=39.6 kJ mol?1). The substrate scope was also evaluated. Under the optimized reaction conditions, 20 terminal epoxides were converted at room temperature to the corresponding cyclic carbonates, which were isolated in yields up to 99 %. The reaction is easily scalable and was performed on a scale up to 50 g substrate. Moreover, this method was applied in the synthesis of the antitussive agent dropropizine starting from epichlorohydrin and phenylpiperazine. Furthermore, DFT calculations were performed to rationalize the mechanism and the high efficiency of the phenol-based phosphonium iodide catalyst. The calculation confirmed the activation of the epoxide via hydrogen bonding for the iodide salt, which facilitates the ring-opening step. Notably, the effective Gibbs energy barrier regarding this step is 97 kJ mol?1 for the bromide and 72 kJ mol?1 for the iodide salt, which explains the difference in activity.

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