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Cas Database




  • Product Name:Styrene

  • CAS Number: 100-42-5

  • EINECS:202-851-5

  • Molecular Weight:104.152

  • Molecular Formula: C8H8

  • HS Code:2902500000

  • Mol File:100-42-5.mol

Synonyms:Styrene(8CI);Cinnamene;Ethenylbenzene;NSC 62785;Phenethylene;Phenylethene;Phenylethylene;Styrol;Styrole;Styrolene;Styropol SO;TTB 7302;Vinylbenzene;Vinylbenzol;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,ToxicT,FlammableF

  • Hazard Codes: Xn:Harmful;

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH315 Causes skin irritation H319 Causes serious eye irritation H332 Harmful if inhaled H372 Causes damage to organs through prolonged or repeated exposure H361d

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. 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. Do NOT induce vomiting. Give one or two glasses of water to drink. Rest. Moderate irritation of eyes and skin. High vapor concentrations cause dizziness, drunkeness, and anesthesia. (USCG, 1999)Excerpt from ERG Guide 133 [Flammable Solids]: Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control 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. /Aromatic hydrocarbons and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use water spray to cool unopened containers. Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back. At elevated temperatures such as in fire conditions, polymerization may take place which may lead to container explosion. (USCG, 1999)Excerpt from ERG Guide 133 [Flammable Solids]: Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare-burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished. (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: particulate filter respirator adapted to the airborne concentration of the substance. Ventilation. Remove all ignition sources. Sweep spilled substance into covered suitable, labelled containers. If styrene is spilled or leaked ... /in/ small quantities, absorb on paper towels. Evaporate in a safe place (such as a fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork. Burn the paper in a suitable location away from combustible materials. Large quantities can be collected and atomized in a suitable combustion chamber. Combustion may be improved by mixing with a more flammable liq.

  • 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 incompatible materials. See Chemical Dangers. Cool. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access.Must be inhibited during storage.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 15 Minute Short-Term Exposure Limit: 100 ppm (425 mg/cu m).Recommended Exposure Limit: 10 Hour Time-Weighted Average: 50 ppm (215 mg/cu m).Biological 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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Relevant articles and documentsAll total 1443 Articles be found



, p. 3579 - 3580 (1981)

It is shown that Ni-B catalysts modified with a small amount of copper(II) salt have a hgher selectivity than palladium and modified Raney nickel catalysts for partial hydrogenation of phenylacetylene, 1-heptyne, 1-ethynylcyclohexene, and propargyl alcoho

Promoting Role of Iron Series Elements Modification on Palladium/Nitrogen Doped Carbon for the Semihydrogenation of Phenylacetylene

Zhang, Wei,Wu, Wei,Long, Yu,Qin, Jiaheng,Wang, Fushan,Ma, Jiantai

, p. 1510 - 1517 (2019)

In this work, an effective and versatile modification approach of palladium (Pd)/nitrogen doped carbon by iron series element for the semihydrogenation of phenylacetylene is presented. Pd and iron series element M (M=Fe, Co or Ni) particles were co-reduce

Defect-site promoted surface reorganization in nanocrystalline ceria for the low-temperature activation of ethylbenzene


, p. 3062 - 3063 (2007)

Defect-site enriched nanocrystalline ceria prepared by an alcoholysis method favors oxidative dehydrogenation of ethylbenzene using nitrous oxide with high conversion and selectivity at much lower temperatures compared to ceria samples prepared by other c

Oxorhenium-catalyzed deoxydehydration of glycols and epoxides

Davis, Jacqkis,Srivastava, Radhey S.

, p. 4178 - 4180 (2014)

The conversion of renewable cellulosic biomass into hydrocarbons has attracted significant attention with a growing demand of sustainability. MeReO3 catalyzes the deoxydehydration (DODH) of glycols and epoxides to alkenes by primary and secondary alcohols (5-nonanol, 3-octanol, 1-butanol) in the benzene solvent. The product yield range from moderate to excellent.

The reactivity of ketyl and alkyl radicals in reactions with carbonyl compounds


, p. 2110 - 2116 (1998)

A parabolic model of bimolecular radical reactions was used for analysis of the hydrogen transfer reactions of ketyl radicals: >C+OH + R1COR2 → >C=O + R1R2C+OH. The parameters describing the reactivity of the reagents were calculated from the experimental data. The parameters that characterize the reactions of ketyl and alkyl radicals as hydrogen donors with olefins and with carbonyl compounds were obtained: >C+OH + R1CH=CH2 → >C=O + R1C+ HCH3; >R1CH=CH2 + R2C+HCH2R3 → R2C+HCH3 + R2CH=CHR3. These parameters were used to calculate the activation energies of these transformations. The kinetic parameters of reactions of hydrogen abstraction by free radicals and molecules (aldehydes, ketones, and quinones) from the C-H and O-H bonds were compared.

Selective Reduction of Alkynes to (Z)-Alkenes via Niobium- or Tantalum-Alkyne Complexes

Kataoka, Yasutaka,Takai, Kazuhiko,Oshima, Koichiro,Utimoto, Kiitiro

, p. 1615 - 1618 (1992)


Mercury in Organic Chemistry. 25. Rhodium(I)-Catalyzed Alkenylation of Arylmercurials

Larock, R. C.,Narayanan, K.,Hershberger, S. S.

, p. 4377 - 4380 (1983)

Arylmercurials and vinyl halides are catalytically cross-coupled to aryl olefins in fair to good yields by 10percent ClRh(PPh3)3.This reaction appears to proceed through an arylvinylrhodium(III) intermediate.

Practical iron-catalyzed dehalogenation of aryl halides

Czaplik, Waldemar Maximilian,Grupe, Sabine,Mayer, Matthias,Wangelin, Axel Jacobi Von

, p. 6350 - 6352 (2010)

An operationally simple iron-catalyzed hydrodehalogenation of aryl halides has been developed with 1 mol% Fe(acac)3 and commercial t-BuMgCl as reductant. The mild reaction conditions (THF, 0 °C, 1.5 h) effect rapid chemoselective dehalogenation of (hetero)aryl halides (I, Br, Cl) and tolerate F, Cl, OR, SR, CN, CO2R, and vinyl groups.

An ionic compound containing Ru(III)-complex cation and phosphotungstate anion as the efficient and recyclable catalyst for clean aerobic oxidation of alcohols

Wang, Sa-Sa,Zhang, Jing,Zhou, Cheng-Liang,Vo-Thanh, Giang,Liu, Ye

, p. 152 - 154 (2012)

A novel ionic compound (3, [RuCl4(L)2] 3PW12O40) containing the Ru(III)-complex cation and α-Keggin-type phosphotungstate anion was synthesized and proven to be the efficient catalyst for aerobic oxidations of alcohols free of base and nitroxyl radical. Specially, 3 could be reused at least five runs without obvious activity loss. The stability of 3 was dramatically improved due to the incorporation of [PW12O40]3 - as the counter-anions, leading to its available recyclability.

Facile Styrene Formation from Ethylene and a Phenylplatinum(II) Complex Leading to an Observable Platinum(II) Hydride

Pal, Shrinwantu,Kusumoto, Shuhei,Nozaki, Kyoko

, p. 502 - 505 (2017)

A new 2-(di-tert-butylphosphanyl)benzenesulfonate-supported phenylplatinum(II) complex instantaneously but reversibly binds ethylene at room temperature. Direct and rapid styrene formation at room temperature via insertion of the PtII-bound ethylene into the PtII-Ph fragment followed by β-hydride elimination results in the formation of a solution-stable PtII-H complex. The PtII-H fragment is resistant toward protonolysis by acetic acid. Oxidation of the PtII-H fragment by excess CuII(OTf)2 leads to an inorganic PtII complex incapable of C-H activation.

Anhydrous Copper(II) Sulfate: An Efficient Catalyst for the Liquid-Phase Dehydration of Alcohols

Hoffman, Robert V.,Bishop, Richard D.,Fitch, Patricia M.,Hardenstein, Richard

, p. 917 - 919 (1980)


Viologens Used in "Electron Phase Transfer". Catalytic Debromination of vic-Dibromides under Heterophase Condition Using Viologens.

Endo, Takeshi,Saotome, Yashushi,Okawara, Makoto

, p. 1124 - 1125 (1984)


Thermal Ring-Splitting Reactions of Diarylcyclobutanes: Significance of Steric Effects on Orbital Interactions in Transition States and Biradical Intermediates

Yasuda, Masahide,Yoshida, Kouhei,Shima, Kensuke,Pac, Chyongjin,Yanagida, Shozo

, p. 1943 - 1950 (1989)

Regiochemistry and rectivities in the thermal ring-splitting reactions of diarylcyclobutanes (1-5) have been studied and shown to depend on the stable conformations and rotational mobilities of the aryl substituents.The reactions of 1 and 2 result in a regiospecific symmetric cleavage to give indene or styrene along with significant isomerization of 2 to 3.In the cases of 3-5 both the symmetric and unsymmetric cleavages competitively occur with decreasing symmetric-to-unsymmetric ratios with an increase in methyl substitution.The olefin products from 4 are mixtures of cis- and trans-2-butene, cis- and trans-β-methylstyrene, and trans-stilbene.Thermochemical analyses combined with product analyses indicate that the symetric cleavage of 1 and the unsymmetric cleavage of 3 proceed with a concerted mechanism, whereas 1,4-biradicals are involved in the other reactions.Structure-reactivity relationships of the present reactions are discussed in terms of mixing of the ?* character in a bonding MO by specific ?-?* interactions, depending on the conformational situations of the aryl groups and in terms of the steric effects which destabilize 1,4-biradicals as well as transition states of the biradical fragmentation to the olefins.

Nickel-catalyzed Kumada reaction of tosylalkanes with Grignard reagents to produce alkenes and modified arylketones

Wu, Ji-Cheng,Gong, Lu-Bing,Xia, Yuanzhi,Song, Ren-Jie,Xie, Ye-Xiang,Li, Jin-Heng

, p. 9909 - 9913 (2012)

Open a new door: The first example of alkene synthesis from alkyl electrophiles with Grignard reagents using the Kumada cross-coupling reaction strategy is reported. This method opens a new door for the Kumada cross-coupling reaction, allowing alkenes to be prepared from the reaction of tosylalkanes with Grignard reagents. Copyright



, p. 3190 (1933)



Traynelis,V.J. et al.

, p. 2377 - 2383 (1962)


New Ruthenium-Molybdenum and -Tungsten Heterodinuclear Complexes with trans-Styryl Ligand

Fukuoka, Atsushi,Ohashi, Nobutoshi,Komiya, Sanshiro

, p. 69 - 72 (1992)

New styryl ruthenium-molybdenum and -tungsten complexes Cp(CO)3M-Ru (trans-styryl)(CO)(PPh3)2 have been prepared by the metathetical reactions of Ru(trans-styryl)Cl(CO)(PPh3)2 with Na.The reactions of 2 with CO and with PMe3

A Gas-phase Anionic Analog of the Wittig Reaction. An Ion Cyclotron Resonance Study of the Gas-phase Ion Chemistry of Silyl Carbanions

Campanaro, A.,Marvin, C. H.,Morehouse, S. P.,McMahon, T. B.

, p. 663 - 668 (1988)

Gas-phase ion-molecule reactions of a variety of fluorosilyl carbanions with compounds containing double bonds to oxygen, X=O, have been examined using pulsed ion cyclotron resonance spectroscopy.The predominant reaction channel observed for species not containing acidic hydrogen is a Wittig-like process involving Si-O bond formation and elimination of X=CH2 species.The gas-phase acidity of F3Si(CH3) has been determined and those of F2Si(CH3)2 and FSi(CH3)3 have been estimated.From the fluoride transfer reactions of F3SiCH2- the fluoride affinity of F2Si=CH2 has been estimated and limits on the ? bond strength in this silaethene obtained.Potential analytical applications of the Wittig reactivity have been discussed.

Palladium-catalyzed convenient one-pot synthesis of multi-substituted 2-pyrones via transesterification and alkenylation of enynoates

Pathare, Ramdas S.,Sharma, Shivani,Gopal, Kandasamy,Sawant, Devesh M.,Pardasani, Ram T.

, p. 1387 - 1389 (2017)

An efficient one-pot protocol for the synthesis of multi-substituted 2-pyrone derivatives from internal alkynes and unactivated alkenes is reported. The methodology involves difunctionalization of internal alkynes by using Pd(II) as a catalyst alongwith X-Phos as ligand via 6-endo transesterification and subsequent alkenylation pathway. Notable features include simple and easily available starting materials, including a range of unactivated alkenes, reduced synthetic steps and mild reaction conditions with high efficiency.

Amine hemilability enables boron to mechanistically resemble either hydride or proton

Lee, C. Frank,Diaz, Diego B.,Holownia, Aleksandra,Kaldas, Sherif J.,Liew, Sean K.,Garrett, Graham E.,Dudding, Travis,Yudin, Andrei K.

, p. 1062 - 1070 (2018)

Tetracoordinate MIDA (N-methyliminodiacetic acid) boronates have found broad utility in chemical synthesis. Here, we describe mechanistic insights into the migratory aptitude of the MIDA boryl group in boron transfer processes, and show that the hemilabil

Atomic layer deposition of aluminium on anatase: A solid acid catalyst with remarkable performances for alcohol dehydration

Song, Yingji,Xu, Shaodan,Ling, Fei,Tian, Panpan,Ye, Tao,Yu, Deqing,Chu, Xuefeng,Lin, Yingzi,Yang, Xiaotian,Tang, Junhong

, p. 34 - 38 (2017)

Here we reported the synthesis of Al sites with ultra-high dispersion on anatase by an atomic layer deposition (ALD) method (ALD-Al/TiO2), which exhibits Br?nsted acidity and satisfactory activity in the dehydration of alcohols, a key step in the deoxygenation of biomass. More importantly, the ALD-Al/TiO2 catalyst has good stability, which is sintering-resistant and gives constant catalytic performances after treatments at high temperature.

Stereospecific rhenium catalyzed desulfurization of thiiranes

Jacob, Josemon,Espenson, James H.

, p. 1003 - 1004 (1999)

Methyltrioxorhenium catalyzes the efficient and stereospecific desulfurization of thiiranes by triphenylphosphine at room temperature, moreso when MTO has been pretreated with hydrogen sulfide, with a Re(v) species as the active form of the catalyst.

Readily recyclable catalysts of zeolite nanoparticles linked with polymer chains

Okamoto, Masaki,Watanabe, Satoshi,Nitta, Junya

, p. 55 - 60 (2013)

Aggregates of zeolite nanoparticles were linked together with polypropylene oxide or polydimethylsiloxane polymer chains, and were used as catalysts for liquid-phase reactions. The polymer-linked catalysts showed high catalytic activity in esterification of acetic acid with 1-propanol and hydrolysis of ethyl acetate, and were readily separated from reaction mixtures by decantation. Moreover, the linkage with the polymer chains enhanced shape selectivity in esterification of acetic acid with cyclohexanol and dehydration of 1-phenylethanol because of passivating the external acid sites of the zeolite with the polymer.

The Dehalogenation of vic-Dihaloalkanes to Alkenes with Sodium Trithiocarbonate or Sodium Dithiocarbonate in the Presence of Phase-Transfer Catalysts

Sugawara, Akira,Nakamura, Atsushi,Araki, Akitoshi,Sato, Ryu

, p. 2739 - 2741 (1989)

The reductive dehalogenation of vic-dihaloalkanes with aqueous sodium trithiocarbonate or sodium dithiocarbonate in the presence of a phase-transfer catalyst gave the corresponding alkenes in high yields under mild conditions.

Liquid-phase dehydration of 1-phenylethanol to styrene over sulfonated D-glucose catalyst

Hasan, Zubair,Hwang, Jin-Soo,Jhung, Sung Hwa

, p. 30 - 33 (2012)

Dehydration of 1-phenylethanol to produce styrene has been studied in liquid phase without any solvent with carbon-based solid acid catalysts prepared in one step from renewable resources like d-glucose for the first time. The carbon-based catalyst shows


, p. 3027 (1967)

Phosphine and N-heterocyclic carbene ligands on Pt(II) shift selectivity from ethylene hydrophenylation toward benzene vinylation

Brosnahan, Anna M.,Talbot, Austin,McKeown, Bradley A.,Kalman, Steven E.,Gunnoe, T. Brent,Ess, Daniel H.,Sabat, Michal

, p. 248 - 255 (2015)

Abstract A series of Pt(II) complexes of the type ([(L~L)Pt(L′)(Ph)][BAr′4] (L~L = 1,2-bis(dimethylphosphino)ethane, 1,2-bis(diphenylphosphino)ethane, (N-pyrrolyl)2P(CH2)2P(N-pyrrolyl)2, 1,3-bis(diphe

A stable well-defined copper hydride cluster consolidated with hemilabile phosphines

Yuan, Shang-Fu,Luyang, Heng-Wang,Lei, Zhen,Wan, Xian-Kai,Li, Jiao-Jiao,Wang, Quan-Ming

, p. 4315 - 4318 (2021)

Copper hydrides are very useful in hydrogenation reactions. We report a stable Stryker-type copper hydride reagent protected by hemilabile phosphines: [Cu8H6(dppy)6](OTf)2(Cu8-H, dppy = diphenylphosphino-2-pyridine). The metal core of this cluster has a bicapped octahedral configuration, and the copper-bound hydrides each triply bridges over a triangular face of the octahedron. This cluster is attractive due to its facile preparation and excellent stability under ambient conditions. The comparable activity and selectivity both in the stoichiometric and catalytic reactions makeCu8-Ha promising alternative to Stryker's reagent.

Pyrolysis of Ethylbenzene

Brooks, C. Terence,Peacock, Stanley J.,Reuben, Bryan G.

, p. 3187 - 3202 (1982)

The pyrolysis of ethylbenzene has been studied using a static reactor.At low conversion hydrogen and styrene are the major products together with methane, toluene, ethylene, ethane and benzene plus traces of higher molecular-weight hydrocarbons.The pyroly

Domino Methylenation/Hydrogenation of Aldehydes and Ketones by Combining Matsubara's Reagent and Wilkinson's Catalyst

Maazaoui, Radhouan,Pin-Nó, María,Gervais, Kevin,Abderrahim, Raoudha,Ferreira, Franck,Perez-Luna, Alejandro,Chemla, Fabrice,Jackowski, Olivier

, p. 5732 - 5737 (2016)

The methylenation/hydrogenation cascade reaction of aldehydes or ketones through a domino process involving two ensuing steps in a single pot is realized. The compatibility of Matsubara's reagent and Wilkinson's complex give a combination that allows, under dihydrogen, the transformation of a carbonyl function into a methyl group. This new method is suitable to introduce an ethyl motif from aromatic and aliphatic aldehydes with total chemoselectivity and total retention of α-stereochemical purity. The developed procedure is also extended to the introduction of methyl groups from ketones.

Catalytic reactions of samarium(II) iodide

Corey,Zheng, Guo Zhu

, p. 2045 - 2048 (1997)

A system for in situ regeneration of SmI2 from SmI3 is described which allows the annulation of ketones to γ-lactones, the deoxygenation of oxiranes to olefins and radical π-cyclization to be conducted with 10 mole % SmI2.

Measurement of Deuterium Kinetic Isotope Effects in Organic and Biochemical Reactions by Natural Abundance Deuterium NMR Spectroscopy

Pascal, Robert A. Jr.,Baum, Mary W.,Wagner, Carol K.,Rodgers, Lauren R.,Huang, Ded-Shih

, p. 6477 - 6482 (1986)

Natural abundance deuterium NMR spectroscopy is a powerful and convenient tool for the estimation of deuterium kinetic isotope effects in organic reactions, obviating in many cases the preparation of isotopically enriched reactants for such measurements.Determinations of the primary or secondary kinetic isotope effects for a broad variety of reaction types are described to illustrate this technique.

β-Cyclodextrin as a Molecular Reaction Vessel: Reactions of Included Phenylmethyldiazirine

Abelt, Christopher J.,Pleier, Jennifer M.

, p. 2159 - 2162 (1988)

Phenylmethyldiazirine forms a stable, solid complex with β-cyclodextrin.The diazirine was decomposed by pyrolysis or irradiation of the complex, and the reaction products were analyzed.The major volatile products consist of the isomeric 1,2-diphenyl-1-methylcyclopropanes.Under photolytic conditions a significant amount of styrene also is formed.The selectivity for trans isomer formation is 10 times greater from the CD complex than from the neat state.Carbene insertion products with β-cyclodextrin are formed under both reaction conditions.The product distributions are explained by cage and shape-selective effects exerted by β-cyclodextrin.

Alkene Formation through Condensation of Phenylmethanesulphonyl Fluoride with Carbonyl Compounds

Kagabu, Shinzo,Hara, Kenji,Takahashi, Junko

, p. 408 - 410 (1991)

Arylmethanesulphonyl fluorides condense with aromatic, aliphatic and conjugated aldehydes and ketones in the presence of potassium carbonate and a crown ether to give aryl-substituted alkenes in satisfactory to modest yields.

Reduction of Organic Halides with Diethyl Phosphonate and Triethylamine

Hirao, Toshikazu,Kohno, Shuichiro,Ohshiro, Yoshiki,Agawa, Toshio

, p. 1881 - 1882 (1983)

Reduction of organic halides with diethyl phosphonate and triethylamine is surveyed.

Catalytic activity of iron-substituted polyoxotungstates in the oxidation of aromatic compounds with hydrogen peroxide

Estrada, Ana C.,Simoes, Mario M. Q.,Santos, Isabel C. M. S.,Neves, M. Graca P. M. S.,Cavaleiro, Jose A. S.,Cavaleiro, Ana M. V.

, p. 1223 - 1235 (2010)

The tetrabutylammonium (TBA) salts of Keggin-type polyoxotungstates of the general formula [XW11FeIII(H2O)O39] n-, where X = P, B or Si, were evaluated as catalysts in the oxidation, under mild conditions, of ethylbenzene, cumene, p-cymene and sec-butylbenzene with aqueous H2O2 in CH3CN at 80 °C. The influence of various factors, such as the substrate/catalyst molar ratio, the amount of oxidant added or the reaction time, was investigated in a systematic way. Generally, the system exhibited moderate conversion, with good selectivity towards the corresponding acetophenone and hydroperoxide. In order to understand the reaction pathways, the oxidation of several products and presumed intermediates was also carried out in the presence of TBA 4[PW11Fe(H2O)O39]?2H 2O. Under the conditions used, the oxidation of styrene and styrene derivatives gave rise mainly to carbon-carbon double-bond cleavage, affording the corresponding products in very high yields (81-87%). Possible reaction pathways are presented.


Wakita, Yoshiaki,Yasunaga, Tomoyuki,Kojima, Masaharu

, p. 261 - 268 (1985)

Secondary and/or tertiary alcohols and unsymmetrical ketones have been obtained in moderate to good yields by palladium-catalyzed (5 molpercent) carbonylative coupling of aryl iodides with alkylaluminum compounds under very mild conditions (20-50 deg C, 1 atm of carbon monoxide).The type of th reaction product depended on the aluminum reagent employed.While the selective formation of secondary alcohols was observed in the reaction with i-Bu3Al, the use of Et3Al led to a mixture of a ketone and two alcoholic products.With Et2AlCl predominantly unsymmetrical ketones were produced.In all cases, formation of directly cross-coupled products was not observed.DME and benzene can be used as solvents, but THF is unsuitable.Nickel catalysts were found to be ineffective for this reaction.

Hydrophobic aluminosilicate zeolites as highly efficient catalysts for the dehydration of alcohols

Xu, Shaodan,Sheng, Huadong,Ye, Tao,Hu, Dan,Liao, Shangfu

, p. 75 - 79 (2016)

Efficient dehydration of alcohols to olefins, acting as a control step in the upgrading of phenolic biofuel into alkane fuels, is an important topic in biomass conversion. Here, we report the design and synthesis of hydrophobic aluminosilicate ZSM-5 zeolites by an organosilane-modification approach (ZSM-5-OS). Water-droplet contact angle tests confirm the formation of hydrophobic surface after the modification. Interestingly, the obtained ZSM-5-OS catalysts exhibit excellent catalytic properties in dehydration of various alcohols into the corresponding olefins in water solvent. The approach reported in this work would be potentially important for developing more efficient catalysts for biomass conversion in the future.

Protophilic versus Silicophilic Reactions in β-Substituted Silanes

Jones, Steven L.,Stirling, Charles J. M.

, p. 1153 - 1154 (1988)

Reactivity in β-eliminations mediated by nucleophilic attack at silicon has been measured as a function of nucleophile, leaving group, and α-substituent; in some instances competition between protophilic and silicophilic reactions is observed.


Overberger et al.

, p. 687 (1969)


Mechanistic Studies of Single-Step Styrene Production Catalyzed by Rh Complexes with Diimine Ligands: An Evaluation of the Role of Ligands and Induction Period

Zhu, Weihao,Luo, Zhongwen,Chen, Junqi,Liu, Chang,Yang, Lu,Dickie, Diane A.,Liu, Naiming,Zhang, Sen,Davis, Robert J.,Gunnoe, T. Brent

, p. 7457 - 7475 (2019)

Studies of catalytic benzene alkenylation using different diimine ligated Rh(I) acetate complexes and Cu(OAc)2 as the oxidant revealed statistically identical results in terms of activity and product selectivity. Under ethylene pressure, two representative diimine ligated rhodium(I) acetate complexes were demonstrated to exchange the diimine ligand with ethylene rapidly to form [Rh(μ-OAc)(??2-C2H4)2]2 and free diimine. Thus, it was concluded that diimine ligands are not likely coordinated to the active Rh catalysts under catalytic conditions. At 150 °C under catalytic conditions using commercial Cu(OAc)2 as the oxidant, [Rh(μ-OAc)(??2-C2H4)2]2 undergoes rapid decomposition to form catalytically inactive and insoluble Rh species, followed by gradual dissolution of the insoluble Rh to form the soluble Rh, which is active for styrene production. Thus, the observed induction period under some conditions is likely due to the formation of insoluble Rh (rapid), followed by redissolution of the Rh (slow). The Rh decomposition process can be suppressed and the catalytically active Rh species maintained by using soluble Cu(II) oxidants or Cu(OAc)2 that has been preheated. In such cases, an induction period is not observed.

A Cp-based Molybdenum Catalyst for the Deoxydehydration of Biomass-derived Diols

Li, Jing,Lutz, Martin,Klein Gebbink, Robertus J. M.

, p. 6356 - 6365 (2020)

Dioxo-molybdenum complexes have been reported as catalysts for the deoxydehydration (DODH) of diols and polyols. Here, we report on the DODH of diols using [Cp*MoO2]2O as catalyst (Cp*=1,2,3,4,5-pentamethylcyclopentadienyl). The DODH reaction was optimized using 2 mol % of [Cp*MoO2]2O, 1.1 equiv. of PPh3 as reductant, and anisole as solvent. Aliphatic vicinal diols are converted to the corresponding olefins by [Cp*MoO2]2O in up to 65 % yield (representing over 30 turnovers per catalyst) and 91 % olefin selectivity, which rivals the performance of other Mo-based DODH catalysts. Remarkably, cis-1,2-cyclohexanediol, which is known as quite a challenging substrate for DODH catalysis, is converted to 30 % of 1-cyclohexene under optimized reaction conditions. Overall, the mass balances (up to 79 %) and TONs per Mo achievable with [Cp*MoO2]2O are amongst the highest reported for molecular Mo-based DODH catalysts. A number of experiments aimed at providing insight in the reaction mechanism of [Cp*MoO2]2O have led to the proposal of a catalytic pathway in which the [Cp*MoO2]2O catalyst reacts with the diol substrate to form a putative nonsymmetric dimeric diolate species, which is reduced in the next step at only one of its Mo-centers before extrusion of the olefin product.

Use of Kinetic Isotope Effects in Mechanism Studies. 3. Measurements of Hydrogen Isotope Effects on the Primary Chlorine Effect during Elimination Reactions

Koch, H. F.,Koch, J. G.,Tumas, W.,McLennan, D. J.,Dobson, B.,Lodder, G.

, p. 7955 - 7956 (1980)


Dichloropalladium(II): An Effective Catalyst for Cross-Coupling of secondary and Primary Alkyl Grignard and Alkylzinc Reagents with Organic Halides

Hayashi, Tamio,Konishi, Mitsuo,Kobori, Yuji,Kumada, Makoto,Higuchi, Taiichi,Hirotsu, Ken

, p. 158 - 163 (1984)

Several phosphine-palladium and -nickel complexes were examined for their catalytic activity in the reaction of sec-butylmagnesium chloride with bromobenzene, (E)-β-bromostyrene, 4-bromoanisole, and 2-bromotoluene.Dichloropalladium(II) was found to be by far the most active and selective catalyst to give the corresponding sec-butyl derivatives in high yields with no byproducts.The palladium-dppf complex was also found highly effective in catalyzing the reaction of n-butylmagnesium chloride and sec- and n- butylzinc chloride with organic bromides to give the corresponding cross-coupling products in high yields.The structure of PdCl2(dppf) has been determined by an X-ray diffraction study.It is proposed that the high efficiency of PdCl2(dppf) catalyst can be ascribed to its large P-Pd-P angle and small Cl-Pd-Cl angle.

Selective Semi-Hydrogenation of Terminal Alkynes Promoted by Bimetallic Cu-Pd Nanoparticles

Buxaderas, Eduardo,Volpe, María Alicia,Radivoy, Gabriel

, p. 1466 - 1472 (2019)

The selective semi-hydrogenation of terminal alkynes was efficiently performed, under mild reaction conditions (H 2 balloon, 110 °C), promoted by a bimetallic nanocatalyst composed of copper and palladium nanoparticles (5:1 weight ratio) supported on mesostructured silica (MCM-48). The Cu-PdNPS@MCM-48 catalyst, which demonstrated to be highly chemoselective towards the alkyne functionality, is readily prepared from commercial materials and can be recovered and reused after thermal treatment followed by reduction under H 2 atmosphere.

Para-hydrogen-induced polarization in rhodium complex-catalyzed hydrogenation reactions

Kirss, Rein U.,Eisenberg, Richard

, p. C22 - C26 (1989)

The homogeneous hydrogenation of PhCCH catalyzed by RhClL3, Rh(COD)L2+, and Rh(COD)dppe+ (L=PPh3; COD=1,5-cyclooctadiene; dppe=1,2-bis(diphenylphosphino)ethane) has been investigated using para-hydrogen-induced polarization (PHIP) which shows that in accord with earlier studies, for RhClL3 the addition of H2 is reversible, whereas for Rh(COD)(dppe)+ and Rh(COD)L2+, H2 addition in hydrogenation catalysis is irreversible.

Electrochemically supported deoxygenation of epoxides into alkenes in aqueous solution

Huang, Jing-Mei,Lin, Zhi-Quan,Chen, Dong-Song

, p. 22 - 25 (2012)

An efficient synthesis of alkenes from epoxides in a mixture of saturated aqueous NH4Br and tetrahydrofuran (8:1) has been developed in an undivided cell fitted with a pair of zinc electrodes, and it is proposed that the reaction is mediated by Zn(0) with a hierarchically organized nanostructure.

Minimizing side reactions in chemoenzymatic dynamic kinetic resolution: Organometallic and material strategies

Pollock, Ciara L.,Fox, Kevin J.,Lacroix, Sophie D.,McDonagh, James,Marr, Patricia C.,Nethercott, Alanna M.,Pennycook, Annie,Qian, Shimeng,Robinson, Linda,Saunders, Graham C.,Marr, Andrew C.

, p. 13423 - 13428 (2012)

Chemoenzymatic dynamic kinetic resolution (DKR) of rac-1-phenyl ethanol into R-1-phenylethanol acetate was investigated with emphasis on the minimization of side reactions. The organometallic hydrogen transfer (racemization) catalyst was varied, and this



, p. 5311 (1950)


An evaluation of phosphine and carbene adducts of phosphite- and phosphinite-based palladacycles in the coupling of alkyl bromides with aryl boronic acids

Bedford, Robin B.,Betham, Michael,Coles, Simon J.,Frost, Robert M.,Hursthouse, Michael B.

, p. 9663 - 9669 (2005)

A range of palladacyclic catalysts and their phosphine and carbene adducts were tested in the Suzuki coupling of an alkyl bromide with phenylboronic acid and showed modest activity in some cases. Unlike with aryl halide substrates it appears that there is no particular benefit in the use of palladacycles as the palladium source. Initial data indicate that the rate determining step is not the oxidative addition of the alkyl halide substrate, but rather lies later in the catalytic cycle.

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

Chen, Jingyun,Chen, Shufang,Jiang, Jun,Lu, Qianqian,Shi, Liyang,Xu, Zekun,Yimei, Zhao

supporting information, (2021/11/09)

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

Selective C(sp3)?N Bond Cleavage of N,N-Dialkyl Tertiary Amines with the Loss of a Large Alkyl Group via an SN1 Pathway

Bai, Lu,Li, Linqiang,Liu, Mengtian,Luan, Xinjun,Wu, Jiaoyu

supporting information, (2021/12/01)

Polar disconnection of the C(sp3)?N bond of N,N-dialkyl-substituted tertiary amines via ammonium species conventionally favored the loss of the smaller alkyl group by an SN2 displacement, while selective C(sp3)?N bond cleavage by cutting off the larger alkyl group is still underdeveloped. Herein, we present a novel Pd0-catalyzed [2+2+1] annulation, proceeding through an alkyne-directed palladacycle formation and consecutive diamination with a tertiary hydroxylamine by cleaving its N?O bond and one C(sp3)?N bond, for the rapid assembly of tricyclic indoles in a single-step transformation. Noteworthy, experimental results indicated that large tert-butyl and benzyl groups were selectively cleaved via an SN1 pathway, in the presence of a smaller alkyl group (Me, Et, iPr). Under the guidance of this new finding, tricyclic indoles bearing a removable alkyl group could be exclusively obtained by using a (α-methyl)benzyl/benzyl or tert-butyl/2-(methoxycarbonyl)ethyl mixed amino source.

Oxidative Alkenylation of Arenes Using Supported Rh Materials: Evidence that Active Catalysts are Formed by Rh Leaching

Luo, Zhongwen,Whitcomb, Colby A.,Kaylor, Nicholas,Zhang, Yulu,Zhang, Sen,Davis, Robert J.,Gunnoe, T. Brent

, p. 260 - 270 (2020/12/01)

This work focuses on the synthesis of supported Rh materials and study of their efficacy as pre-catalysts for the oxidative alkenylation of arenes. Rhodium particles supported on silica (Rh/SiO2; ~3.6 wt% Rh) and on nitrogen-doped carbon (Rh/NC

Recoverable palladium-catalyzed carbon-carbon bond forming reactions under thermomorphic mode: Stille and suzuki-miyaura reactions

Chan, Ka Long,Chiu, Chiao-Fan,Elakkat, Vijayanath,Lu, Norman,Shen, Chia-Rui,Su, Han-Chang,Tessema, Eskedar,Tsai, Zong-Lin

, (2021/05/31)

The reaction of [PdCl2(CH3CN)2] and bis-4,40-(RfCH2OCH2)-2,2'-bpy (1a-d), where Rf = n- C11F23 (a), n-C10F21 (b), n-C9F19 (c) and n-C8F17 (d), respectively, in the presence of dichloromethane (CH2Cl2) resulted in the synthesis of Pd complex, [PdCl2[4,4'-bis-(RfCH2OCH2)-2,2'-bpy] (2a-d). The Pd-catalyzed Stille arylations of vinyl tributyltin with aryl halides were selected to demonstrate the feasibility of recycling usage with 2a as the catalyst using NMP (N-methyl-2-pyrrolidone) as the solvent at 120-150 °C. Additionally, recycling and electronic effect studies of 2a-c were also carried out for Suzuki-Miyaura reaction of phenylboronic acid derivatives, 4-X-C6H4-B(OH)2, (X = H or Ph) with aryl halide, 4-Y-C6H4-Z, (Y = CN, H or OCH3; Z = I or Br) in dimethylformamide (DMF) at 135-150 °C. At the end of each cycle, the product mixtures were cooled to lower temperature (e.g., -10 °C), and then catalysts were recovered by decantation with Pd leaching less than 1%. The products were quantified by gas chromatography/mass spectrometry (GC/MS) analysis or by the isolated yield. The complex 2a-catalyzed Stille reaction of aryl iodides with vinyl tributyltin have good recycling results for a total of 8 times, with a high yield within short period of time (1-3 h). Similarly, 2a-c-catalyzed Suzuki-Miyaura reactions also have good recycling results. The electronic effect studies from substituents in both Stille and Suzuki-Miyaura coupling reactions showed that electron withdrawing groups speed up the reaction rate. To our knowledge, this is the first example of recoverable fluorous long-chained Pd-catalyzed Stille reactions under the thermomorphic mode.

Mild and efficient desulfurization of thiiranes with MoCl5/Zn system

Lee, Yeong Jin,Shin, Jeong Won,Yoo, Byung Woo

, (2021/11/10)

Desulfurization of a variety of thiiranes to alkenes occurs chemoselectively in high yields upon treatment with MoCl5/Zn system under mild conditions. The new methodology demonstrates high functional group tolerance toward chloro, bromo, fluoro, methoxy, ester, ether and keto groups.

Process route upstream and downstream products

Process route

Conditions Yield
With acetic acid; at 105 ℃;
With methanol; at 150 ℃;
Conditions Yield
With diethyl ether;
With chromium chloride; diethyl ether;
With chromium chloride; diethyl ether;
With diethyl ether;
Conditions Yield
With diethyl ether;
With chromium chloride; diethyl ether;
With chromium chloride; diethyl ether;
With diethyl ether;
Conditions Yield
With BaFe0.02Zr0.98O3; at 549.84 ℃; under 760.051 Torr; Reagent/catalyst;
With carbon dioxide; at 544.84 ℃; under 760.051 Torr; Reagent/catalyst;
at 525 ℃; Leiten ueber Chrom(III)-oxyd;
With Ni-V-Sb; water; oxygen; at 599.9 ℃; for 0.000277778h; Product distribution; Mechanism; var. catalyst, var. temp., time, and partial pressure of ethylbenzene;
With metal oxide incorporated zirconium vanadate; at 400 ℃; Flow reactor;
Conditions Yield
With carbon dioxide; at 550 ℃; for 1h; under 750.075 Torr;
TiO2-ZrO2 P; In gas; at 620 ℃;
92.2 % Chromat.
5.8 % Chromat.
3.4 % Chromat.
zirconium(IV) oxide; In gas; at 620 ℃;
89.0 % Chromat.
3.4 % Chromat.
7.6 % Chromat.
TiO2-ZrO2 A; In gas; at 620 ℃;
1.1 % Chromat.
2.1 % Chromat.
96.8 % Chromat.
Leiten ueber Zinkchromat-Katalysatoren;
at 550 - 650 ℃;
zinc(II) oxide; at 599.9 ℃; Product distribution; variously modified ZnO;
vanadia; magnesium oxide; at 520 ℃; Product distribution; var. catalysts (var. temp. of calcination);
With cobalt(II) oxide; air; water; vanadia; magnesium oxide; at 439.9 - 559.9 ℃; Rate constant; Thermodynamic data; apparent activation energy; pre-exponential factor in Arrhenius equation;
With air; Zn0.5Ni0.5Fe2O4; at 500 ℃; Further Variations:; Reagents; Product distribution;
lanthanum(III) oxide; tin(IV) oxide; at 449.85 - 499.85 ℃; for 3h; Further Variations:; Catalysts; Temperatures; Product distribution; Enzymatic reaction;
samarium(III) oxide; vanadia; at 475 ℃; for 1h; Further Variations:; Catalysts; Temperatures; Product distribution;
vanadia; at 475 ℃; Further Variations:; Catalysts; Product distribution;
With (H3O)2[(Mo6Cl8)Cl6]*6H2O; hydrogen; at 400 ℃; Product distribution;
With cerium(IV) oxide; air; molybdenum; at 500 ℃; for 2h; Further Variations:; Reagents; Product distribution;
lanthanum nitrate (7 wtpercent as lanthanum metal); potassium nitrate (1 wtpercent as potassium metal); alumina; mixture of, calcined; at 522 - 582 ℃; Product distribution / selectivity; Continuous reaction;
lanthanum aluminate (LaAlO3); at 555 - 602 ℃; Product distribution / selectivity; Continuous reaction;
lanthanum carbonate (30 wtpercent as lanthanum metal); cerium carbonate (2.6 wtpercent as cerium metal); neodymium carbonate (1.5 wtpercent as neodymium metal); praseodymium carbonate (9 wtpercent as praseodymium metal); nitric acid; potassium nitrate (1 wtpercent as potassium metal); alumina; mixture of, calcined; at 542 - 602 ℃; Product distribution / selectivity; Continuous reaction;
iron and potassium salts; at 590 - 630 ℃; under 300.03 - 637.564 Torr; Conversion of starting material;
With carbon dioxide; at 660 ℃; Autoclave;
With Mg3Fe0.2Co0.25Al0.5; at 550 ℃; for 3h; Inert atmosphere;
With aluminum oxide; at 600 ℃; for 20h; under 760.051 Torr; Reagent/catalyst; Kinetics; Inert atmosphere;
With carbon dioxide; hydrogen; for 5h; under 760.051 Torr; Reagent/catalyst; Kinetics; Inert atmosphere;
With nitrogen doped reducedgraphene oxide dispersed in nanodiamond; at 550 ℃; for 20h; Reagent/catalyst; Inert atmosphere;
With carbon dioxide; at 544.84 ℃; under 760.051 Torr;
With nanodiamond(at)carbon nitride; at 550 ℃; for 20h; Reagent/catalyst; Autoclave; Inert atmosphere;
With carbon dioxide; at 550 ℃; under 760.051 Torr; Reagent/catalyst;
Conditions Yield
With methoxy(cyclooctadiene)rhodium(I) dimer; N,N-Dimethylacrylamide; 3-Methoxybenzoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 90 ℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;
With sodium amalgam; Behandeln mit Wasser;
Conditions Yield
With C21H29ClIrN4O2(1+)*CF3O3S(1-); In 1,2-dichloro-benzene; at 150 ℃; for 4h; Reagent/catalyst; Inert atmosphere;
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 0 ℃; for 3h;
With para-tert-butylphenol; toluene-4-sulfonic acid; In toluene; at 130 ℃; Reagent/catalyst; Large scale;
toluene-4-sulfonic acid; at 225 - 232 ℃; under 300.03 - 322.532 Torr;
With γ-iron(III) oxide; at 219 - 223 ℃;
With MoO2Cl2(H2O)2; In tetrahydrofuran; for 16h; Reflux; Schlenk technique; Green chemistry;
With copper(II) sulfate; In neat (no solvent); at 120 ℃; for 1.5h; under 25 Torr;
With tin(II) trifluoromethanesulfonate; In toluene; at 120 ℃; for 7h;
toluene-4-sulfonic acid; In toluene; at 25 - 110 ℃; for 1 - 2.5h; Heating / reflux;
at 270 - 350 ℃;
at 380 - 400 ℃; Leiten ueber Aluminiumoxyd;
at 400 - 500 ℃; under 10 - 20 Torr; Leiten ueber Aluminiumoxyd oder Bleicherde;
With sulfuric acid;
With potassium hydroxide; at 140 - 170 ℃;
With potassium hydroxide; at 200 ℃;
With ethanol; silica gel; at 350 ℃;
With iodine;
With phosphoric acid;
With copper; at 330 ℃;
With hydrogenchloride; at 100 ℃;
With sulfuric acid; at 110 ℃;
With (R)-10-camphorsulfonic acid; at 82.6 ℃; under 20 Torr;
With oxalyl dichloride;
With oxalic acid;
With toluene-4-sulfonic acid; at 82.6 ℃; under 20 Torr;
With sodium hydrogen sulfate; silica gel; In hexane; for 0.166667h; Heating;
64 % Chromat.
With aluminium trichloride; In tetrahydrofuran; for 2h; Heating;
75 % Chromat.
H-montmorillonite; In 1,4-dioxane; for 4h; Heating;
75 % Chromat.
methyltrioxorhenium(VII); for 72h;
100 % Turnov.
With sodium hydrogen sulfate; silica gel; In hexane; for 0.166667h; Product distribution; Mechanism; Heating; other solvents, catalysts, different time;
64 % Chromat.
With water; defective calcium hydroxyapatite; at 250 ℃; for 2h; Further Variations:; CaO/P2O5 ratio; Product distribution;
for 52h;
toluene-4-sulfonic acid; at 218 - 239 ℃; under 150.015 Torr; Product distribution / selectivity; Continuous process;
With phenol; star-shaped catalyst; at 300 ℃; under 750.075 Torr; Product distribution / selectivity;
With 4-Ethylphenol; benzyl alcohol; star-shaped catalyst; at 300 ℃; under 750.075 Torr; Product distribution / selectivity;
With benzyl alcohol; phenol; star-shaped catalyst; at 300 ℃; under 750.075 Torr; Product distribution / selectivity;
With 4-Ethylphenol; star-shaped catalyst; at 300 ℃; under 750.075 Torr; Product distribution / selectivity;
Conversion of starting material;
With o-toluenesulfonic acid; toluene-4-sulfonic acid; at 230 ℃; Product distribution / selectivity; Industry scale;
With rhenium(VII) oxide; In toluene; at 100 ℃; for 24h;
98 %Chromat.
at 160 ℃; for 0.75h; Inert atmosphere; Microwave irradiation; Ionic liquid;
85 %Spectr.
With sodium hydrogen sulfate; at 110 ℃; for 1h; Neat (no solvent);
94 %Spectr.
With sulfonated D-glucose; at 180 ℃; for 2h; under 600.06 Torr; Neat (no solvent);
With LiCl-acidic alumina; at 85 ℃; for 0.05h; Microwave irradiation;
83 %Chromat.
With polydimethytlsiloxane linked ZSM-5 nanoparticle; In toluene; at 110 ℃;
With ZSM-5 n-hexadecyltrimethoxysilane modified; In water; at 165 ℃; for 20h; under 22502.3 Torr; stereoselective reaction; Inert atmosphere; Autoclave;
In water; at 180 ℃; for 20h; under 22502.3 Torr; Inert atmosphere; Autoclave;
With ARB (activated redbrick clay) clay catalyst; at 250 ℃; under 760.051 Torr; Green chemistry;
With sulfuric acid; at 119.84 ℃; for 4h; under 2250.23 Torr; Autoclave;
Conditions Yield
With potassium hydroxide; at 200 ℃;
With potassium hydroxide; at 140 - 170 ℃;
With potassium hydroxide; copper flask;
copper(II) sulfate; In tetrachloromethane; for 0.833333h; Heating;
83 % Chromat.
With calcium carbide; caesium carbonate; In water; dimethyl sulfoxide; at 160 ℃; for 16h; Inert atmosphere; Sealed tube;
87 %Spectr.
Conditions Yield
at 140 ℃; for 4h; Ionic liquid;
With copper; In quinoline; at 185 - 195 ℃;
bei der Destillation von zimtsaurem Calcium;
With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)]; In toluene; at 120 ℃; for 16h;
90 %Chromat.
With dodecacarbonyl-triangulo-triruthenium; Inert atmosphere;
With ferulic acid decarboxylase from Saccharomyces cerevisiae; phenylacrylic acid decarboxylase from Saccharomyces cerevisiae; sodium chloride; In aq. phosphate buffer; at 25 ℃; pH=7; pH-value; Kinetics; Enzymatic reaction;
With ubiX co-expressed Aspergillus niger Fdc1 protein; potassium chloride; In aq. phosphate buffer; at 25 ℃; pH=6; Kinetics; Enzymatic reaction;
With ferulic acid decarboxylase from Saccharomyces cerevisiae; In aq. phosphate buffer; dimethyl sulfoxide; at 25 ℃; pH=7.4; Kinetics; Enzymatic reaction;
With phenylacrylic acid decarboxylases; In aq. phosphate buffer; Hexadecane; at 30 ℃; Reagent/catalyst; Enzymatic reaction;
With 3Ru*2CO; at 200 ℃; for 4h; Reagent/catalyst; Catalytic behavior; Sealed tube; Inert atmosphere; Glovebox; Schlenk technique;
With Saccharomyces cerevisiae ferulic acid decarboxylase; In tetrahydrofuran; aq. phosphate buffer; at 30 ℃; for 1h; pH=6; Temperature; Enzymatic reaction;
Conditions Yield
at 315 - 320 ℃;

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