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Cas Database

106-89-8

106-89-8

Identification

  • Product Name:Epichlorohydrin

  • CAS Number: 106-89-8

  • EINECS:203-439-8

  • Molecular Weight:92.5251

  • Molecular Formula: C3H5ClO

  • HS Code:2932999099

  • Mol File:106-89-8.mol

Synonyms:Oxirane,(chloromethyl)- (9CI);Propane, 1-chloro-2,3-epoxy- (6CI,8CI);(Chloromethyl)ethylene oxide;(Chloromethyl)oxirane;(RS)-Epichlorhydrin;1,2-Epoxy-3-chloropropane;1-Chloro-2,3-epoxypropane;2,3-Epoxypropyl chloride;2-(Chloromethyl)oxirane;3-Chloro-1,2-epoxypropane;3-Chloro-1,2-propylene oxide;3-Chloropropene-1,2-oxide;3-Chloropropylene oxide;Chloropropylene oxide;Glycerol epichlorohydrin;Glycidyl chloride;J 006;NSC 6747;dl-a-Epichlorohydrin;a-Epichlorohydrin;g-Chloropropylene oxide;

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  • Hazard Codes: T:Toxic;

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Relevant articles and documentsAll total 151 Articles be found

Mechanism of olefin epoxidation in the presence of a titanium-containing zeolite

Danov,Krasnov,Sulimov,Ovcharova

, p. 1809 - 1812 (2013)

The effect of the nature of a solvent on the liquid-phase epoxidation of olefins with an aqueous solution of hydrogen peroxide over a titanium-containing zeolite is studied. Butanol-1, butanol-2, propanol-1, isopropanol, methanol, ethanol, water, acetone, methyl ethyl ketone, isobutanol, and tert-butanol are examined as solvents. A mechanism of olefin epoxidation with hydrogen peroxide in an alcohol medium over a titanium-containing zeolite is proposed. Epoxidation reactions involving hydrogen peroxide and different olefins are studied experimentally.

Efficient Catalytic System Involving Molybdenyl Acetylacetonate and Immobilized Tributylammonium Chloride for the Direct Synthesis of Cyclic Carbonates from Carbon Dioxide and Olefins

Siewniak, Agnieszka,Jasiak-Jaroń, Katarzyna,Kotyrba, ?ukasz,Baj, Stefan

, p. 1567 - 1573 (2017)

Abstract: An effective direct method for preparing of cyclic carbonates from CO2 and olefins in the presence of tert-butyl hydroperoxide as an oxidant was provided. The first stage, the epoxidation of olefins, was carried out using MoO2(acac)2 as a catalyst (1h, 100 °C), and the second stage, the cycloaddition of CO2 to the resulting epoxide, was proceeded in the presence of immobilized tributylmethylammonium chloride on a polystyrene cross-linked with divinylbenzene, and an aqueous solution of ZnBr2 (100 °C, 0.9?MPa of CO2, 4?h). The proposed method allowed to obtain cyclic carbonates with high yields (50–77%) under mild conditions. Moreover, the immobilized catalyst could be reused at least five times without significant loss of its catalytic activity.

Continuous flow upgrading of glycerol toward oxiranes and active pharmaceutical ingredients thereof

Morodo, Romain,Gérardy, Romaric,Petit, Guillaume,Monbaliu, Jean-Christophe M.

, p. 4422 - 4433 (2019)

A robust continuous flow procedure for the transformation of bio-based glycerol into high value-added oxiranes (epichlorohydrin and glycidol) is presented. The flow procedure features a central hydrochlorination/dechlorination sequence and provides economically and environmentally favorable conditions involving an organocatalyst and aqueous solutions of hydrochloric acid and sodium hydroxide. Pimelic acid (10 mol%) shows an exceptional catalytic activity (>99% conversion of glycerol, a high selectivity toward 1,3-dichloro-2-propanol and 81% cumulated yield toward intermediate chlorohydrins) for the hydrochlorination of glycerol (140 °C) with 36 wt% aqueous HCl. These conditions are validated on a sample of crude bio-based glycerol. The dechlorination step is effective (quantitative conversion based on glycerol) with concentrated aqueous sodium hydroxide (20 °C) and can be directly concatenated to the hydrochlorination step, hence providing a ca. 2:3 separable mixture of glycidol and epichlorohydrin (74% cumulated yield). An in-line membrane separation unit is included downstream, providing usable streams of epichlorohydrin (in MTBE, with an optional concentrator) and glycidol (in water). The scalability of the dechlorination step is then assessed in a commercial pilot-scale continuous flow reactor. Next, bio-based epichlorohydrin is further utilized for the continuous flow preparation of β-amino alcohol active pharmaceutical ingredients including propranolol (hypertension, WHO essential), naftopidil (prostatic hyperplasia) and alprenolol (angina pectoris) within a concatenable two-step procedure using a FDA class 3 solvent (DMSO). This work provides the first example of direct upgrading of bio-based glycerol into high value-added pharmaceuticals under continuous flow conditions.

Phase Transfer of the Organic Substrate in the Epoxidation Reaction of Allyl Chloride in Two-Phase Aqueous–Organic Systems

Panicheva,Meteleva,Ageikina,Panichev

, p. 884 - 888 (2018)

Abstract: The mechanism of synergism for mixtures of phase-transfer carriers QХ with tertiary amines and pyridine in the epoxidation reaction of allyl chloride has been established. It has been shown that tertiary amines (triethylamine, tributylamine, N,N-dimethylaniline, and N-methyldiethanolamine) and pyridine oxidizable in situ to N-oxides promote the transfer of the organic substrate (allyl chloride) to the interface (PB). It is assumed that the synergism of mixtures of phase-transfer carriers QХ with a tertiary amine oxide or pyridine oxide can also be due to the formation of a mixture of two catalysts, Q3[PW4O24] and WO(O2)2L (where L = a tertiary amine oxide or pyridine oxide). The WO(O2)2L complex will provide the stage of reoxidation of the complex Q3[PW4O24 ?х] in the organic phase and, hence, the possibility for the development of the process of epoxidation not only at the interface but also in the bulk of the organic phase. The maximum coefficient of synergistic effect (ks = 2) is observed for a mixture of cetylpyridinium bromide (90 mol %) and pyridine N-oxide (10 mol %).

Controlling the Morphology and Titanium Coordination States of TS-1 Zeolites by Crystal Growth Modifier

Chang, Xinyu,Chen, Ziyi,Hu, Dianwen,Jia, Mingjun,Li, Yingying,Song, Xiaojing,Yang, Xiaotong,Yu, Jihong,Zhang, Hao,Zhang, Peng,Zhang, Qiang,Zhang, Tianjun

, p. 13201 - 13210 (2020)

Developing an effective strategy to synthesize perfect titanosilicate TS-1 zeolite crystals with desirable morphologies, enriched isolated framework Ti species, and thus enhanced catalytic oxidation properties is a pervasive challenge in zeolite crystal engineering. We here used an amino acid l-carnitine as a crystal growth modifier and ethanol as a cosolvent to regulate the morphologies and the Ti coordination states of TS-1 zeolites. During the hydrothermal crystallization process, the introduced l-carnitine can not only tailor the anisotropic growth rates of zeolite crystals but also induce the formation of uniformly distributed framework Ti species through building a suitable chemical interaction with the Ti precursor species. Condition optimizations could afford the generation of perfect hexagonal plate TS-1 crystals and elongated platelet TS-1 crystals enriched in tetrahedral framework Ti sites (TiO4) or mononuclear octahedrally coordinated Ti species (TiO6). Both samples showed significant improvement in catalytic activity for the H2O2-mediated epoxidation of alkenes. In particular, the elongated platelet TS-1 enriched in "TiO6"species afforded the highest activity in 1-hexene epoxidation, with a turnover frequency (TOF) of up to 131 h-1, which is approximately twice as high as that of the conventional TS-1 zeolite (TOF: 65 h-1) and even higher than those of the literature-reported TiO6-containting TS-1 catalysts derived from the hydrothermal post-treatment of TS-1 zeolites. This work demonstrates that the morphologies and the titanium coordination states of TS-1 zeolites can be effectively tuned by directly introducing suitable crystal growth modifiers, thus providing new opportunities for developing highly efficient titanosilicate zeolite catalysts for important catalytic applications.

An Easy Way to Prepare Titanium Silicalite-1 (TS-1)

Gao, Huanxin,Suo, Jishuan,Li, Shuben

, p. 835 - 836 (1995)

Titanium silicalite-1 (TS-1) is easily synthesized using an aqueous solution of TiCl3 as the titanium source.

A New, Effective Catalytic System for Epoxidation of Olefins by Hydrogen Peroxide under Phase-Transfer Conditions

Venturello, Carlo,Alneri, Enzo,Ricci, Marco

, p. 3831 - 3833 (1983)

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A safer and greener chlorohydrination of allyl chloride with H2O2 and HCl over hollow titanium silicate zeolite

Peng, Xinxin,Xia, Changjiu,Lin, Min,Shu, Xingtian,Zhu, Bin,Wang, Baorong,Zhang, Yao,Luo, Yibin,Mu, Xuhong

, p. 17 - 25 (2017)

Industrial production of dichloropropanols through chlorohydrination of allyl chloride suffers from a series of disadvantages such as use of hazardous Cl2, low atom economy, low dichloropropanol concentration and serious pollution. In this work, a safer and greener route for chlorohydrination of allyl chloride with H2O2 and HCl over hollow titanium silicate (HTS) at mild condition is developed. Unlike the traditional Cl2-based chlorohydrination, this novel method is initiated via synergistic effect of Lewis acidity (HTS) and Br?nsted acidity (HCl) to promote occurrence of oxidation, protonation and nucleophilic reaction of allyl chloride simultaneously and hence dichloropropanols are generated. Owing to a completely different reaction route, the formation of 1,2,3-trichloropropane by-product is depressed and the content of dichloropropanol exceeded 22?wt%, which increase by about 4 times compared with traditional Cl2-based chlorohydrination (the content of dichloropropanol is below 4?wt%). At the optimized conditions, both of the allyl chloride conversion and dichloropropanol selectivity could approach 99% simultaneously and the waste is minimized. What's more, the HTS was reusable. Concentrated HCl solution treatment was adopted to test HTS's stability. The characterization and catalytic evaluation results reveal that, although parts of the framework Ti species have transformed into non-framework Ti and then leached into the solution, HTS remains structural stable, and the allyl chloride conversion and dichloropropanol selectivity didn't decrease obviously during the treatment.

Converting wastes into added value products: From glycerol to glycerol carbonate, glycidol and epichlorohydrin using environmentally friendly synthetic routes

Dibenedetto, Angela,Angelini, Antonella,Aresta, Michele,Ethiraj, Jayashree,Fragale, Carlo,Nocito, Francesco

, p. 1308 - 1313 (2011)

Glycerol carbonate, synthesised via a non-phosgene route using glycerol and CO2 or urea in presence of a heterogeneous catalyst, was efficiently converted into a series of derivatives through the functionalization of the -OH moiety, using high yield, high selectivity synthetic routes not affecting the carbonate functionality. So, for example, glycerol carbonate was converted into epichlorohydrin, a product that has a large industrial application, under very mild conditions, using a two-step reaction with a 98% yield and 100% selectivity. The high yield and mild reaction conditions (very often close to the ambient conditions) make the environmentally friendly synthetic approach described in this work of potential applicative interest. All compounds prepared were fully characterized.

Kinetics of allyl chloride epoxidation with hydrogen peroxide catalyzed by extruded titanium silicalite

Sulimov,Danov,Ovcharova,Ovcharov,Flid

, p. 712 - 721 (2014)

A mechanism is suggested for the heterogeneous catalytic epoxidation of allyl chloride with hydrogen peroxide in methanol. The kinetics of allyl chloride oxidation into epichlorohydrin in the presence of extruded titanium silicalite has been investigated. A kinetic model of the process has been derived from experimental data, and the activation energies of the target and side reactions, the rate constants of the reactions, and the adsorption equilibrium constant have been determined. The allyl chloride epoxidation process has been tested using a bench-scale continuous apparatus, and the adequacy of the kinetic model has been estimated.

Synthesis of 1,3-dichloropropanol from glycerol using muriatic acid as chlorinating agent

Herliati,Yunus, Robiah,Rashid, Umer,Abidin, Zurina Zainal,Ahamad, Intan Salwani

, p. 2907 - 2912 (2014)

Today, one of the problems associated with biodiesel production is the availability of high amount of glycerol byproduct. Among the various possibilities, technology to convert glycerol to dichloropropanol has diverted our attention. Dichloropropanol an important raw material for epichlorohydrin production was successfully synthesized via hydrochlorination reaction of glycerol with aqueous hydrogen chloride to produce 1,3-dichloropropanol. Experimental study was carried out under temperatures ranged; 80 to 120 °C, reactant molar ratio; 1:16 to 1:32 and various carboxylic acid catalysts. The optimal reaction conditions were: temperature, 110 °C; reactant molar ratio glycerol to HCl, 1:24; catalyst, malonic acid; and time duration, 3 h.

New perspective to catalytic epoxidation of olefins by Keplerate containing Keggin polyoxometalates

Taghiyar, Hamid,Yadollahi, Bahram

, p. 98 - 104 (2018)

Different Keggin encapsulated in Keplerate polyoxometalates (Mo72Fe30, PMo12 ? Mo72Fe30, SiMo12 ? Mo72Fe30 and BW12 ? Mo72Fe30) have been synthesized and their catalytic efficiency in the epoxidation of olefins with hydrogen peroxide investigated. Results were confirmed that Keggin encapsulated in Keplerates could show higher catalytic activity than parent ones. These POM catalysts lead to heterogeneous epoxidation of alkenes by hydrogen peroxide with green features of convenient recovery, steady reuse, high conversion and selectivity, and simple preparation.

Highly efficient and selective production of epichlorohydrin through epoxidation of allyl chloride with hydrogen peroxide over Ti-MWW catalysts

Wang, Lingling,Liu, Yueming,Xie, Wei,Zhang, Haijiao,Wu, Haihong,Jiang, Yongwen,He, Mingyuan,Wu, Peng

, p. 205 - 214 (2007)

The catalytic properties of Ti-MWW in the epoxidation of allyl chloride (ALC) with hydrogen peroxide to epichlorohydrin (ECH) were studied by comparing these properties with those of TS-1, Ti-MOR, and Ti-Beta. Issues concerning the stability and reuse of Ti-MWW were also considered. The investigation on various reaction parameters showed that Ti-MWW is an active and selective catalyst for ALC epoxidation. Ti-MWW prefers aprotic solvents, such as acetonitrile and acetone, over protic alcohols, which is favorable for suppressing the formation of solvolysis byproducts. ALC conversion and ECH selectivity were both as high as 99% on Ti-MWW. 3-Chloro-1,2-propanediol and other heavy byproducts with high boiling points had a negative effect on ALC conversion for both TS-1 and Ti-MWW. A novel secondary synthesis caused a structural rearrangement of the Ti-MWW framework and then improved its stability.

Microwave-assisted epoxidation of simple alkenes in the presence of hydrogen peroxide

Bogdal,Lukasiewicz,Pielichowski,Bednarz

, p. 2973 - 2983 (2005)

A novel application of microwave irradiation for the epoxidation of some simple alkenes, in which hydrogen peroxide was used as an oxidant together with sodium tungsten and phosphorous acid under phase-transfer catalytic (PTC) conditions, is described as a new environmentally benign method. In comparison with conventional heating, the microwave process is a very useful alternative for introducing of the oxirane ring into some unsaturated hydrocarbons because of reduction of the reaction time and increase in yield. Copyright Taylor & Francis, Inc.

Enhanced catalytic activity of titanosilicates controlled by hydrogen-bonding interactions

Deng, Xiujuan,Zhang, Shuo,Wang, Binshen,Wang, Yuning,Wu, Haihong,Liu, Yueming,He, Mingyuan

, p. 7504 - 7506 (2013)

A typical volcano-shaped curve has been found in heterogeneous catalytic systems containing titanosilicates for the first time. A new reactive intermediate with double H-bonds is proposed. Systematic results clearly evidence another H-bond formed between the high-electronegativity atom of the H-bond acceptor and the Hend atom of Ti-Oα-O β-Hend.

Highly efficient epoxidation of cyclohexene with aqueous H2O2 over powdered anion-resin supported solid catalysts

Peng,Lu,Ma,Shen,Wei,He,Zhou,Xia

, p. 393 - 399 (2016)

Resin supported solid acid catalysts have extended the application of conventional solid acid catalysts in the field of selective oxidations. The present work describes selectively catalytic epoxidation of cyclohexene with aqueous 30% H2O2 over powdered anion-resin supported peroxo phosphotungstic acid heterogeneous catalysts prepared through a simple anion-exchange from powdered chloride-form anion resin without any special pre-exchanged treatment. Among these powdered solid catalysts, anion-exchanged resin D201 supported peroxo phosphotungstic acid exhibits the best activity for the titled reaction to obtain 92.4?mol% conversion and 98.1% selectivity of epoxide, for which D201-PWAR(4) behaves as a truly heterogeneous catalyst. Some factors such as various peroxo phosphotungstic acid concentrations, the oxidants, the solvents, the molar ratios of H2O2/cyclohexene, the catalyst amount, the reaction temperature and time play important roles in controlling the epoxidation.

Solvent effect on epoxidation of allyl chloride with hydrogen peroxide on titanium-containing silicalite

Danov,Sulimov,Sulimova

, p. 1963 - 1966 (2008)

The solvent effect on liquid-phase epoxidation of allyl chloride with an aqueous solution of hydrogen peroxide on TS-1 titanium-containing silicalite was examined. 1-Butanol, 2-butanol, 1-propanol, isopropanol, methanol, ethanol, water, acetone, methyl ethyl ketone, and 1-pentanol were tested as solvents.

Epoxidation of allyl chloride with H2O2 catalyzed by three structurally related quaternary ammonium modified polyoxophosphotungstates

Cui, Yu,Jiang, Xuchuan,Sun, Guoxin,Sun, Junhua,You, Qi,Zhao, Xiuxian

, (2020)

The one-step epoxidation of allyl chloride has always been a great challenge for the industrial production. The key of this technology is to find efficient and friendly catalyst. In this paper, three structurally related quaternary ammonium modified polyoxophosphotungstates were synthesized by green and facile method. Among them, [C16H33(CH3)3N]3PW4O24 and [π-C5H5NC16H33]3PW4O24 are reaction-controlled phase transfer catalyst (RPTC) and [(C18H37)2(CH3)2N]3PW4O24 is temperature-controlled phase transfer catalyst (TPTC). All three catalysts could achieve the epoxidation of allyl chloride with equimolar H2O2 under solvent-free and mild conditions. Moreover, the catalysts exhibited excellent catalytic performance and reusability. The catalytic mechanism was explored by FT-IR spectroscopy. The results of kinetic experiments show that the chain length of alkanes and heterocyclic structure of cations have a great influence on the catalytic activity of the catalysts.

Synthesis of ethyl (R)-4-cyano-3-hydroxybutyrate in high concentration using a novel halohydrin dehalogenase HHDH-PL from Parvibaculum lavamentivorans DS-1

Wan, Nan-Wei,Liu, Zhi-Qiang,Huang, Kai,Shen, Zhen-Yang,Xue, Feng,Zheng, Yu-Guo,Shen, Yin-Chu

, p. 64027 - 64031 (2014)

We identified and characterized a novel halohydrin dehalogenase HHDH-PL from Parvibaculum lavamentivorans DS-1. Study of substrate specificity indicated that HHDH-PL possessed a high activity toward ethyl (S)-4-chloro-3-hydroxybutanoate ((S)-CHBE). After optimizations of the pH and temperature, whole cell catalysis of HHDH-PL was applied to the synthesis of ethyl (R)-4-cyano-3-hydroxybutyrate (HN) at 200 g L-1 of (S)-CHBE, which gave 95% conversion and 85% yield in 14 h.

Biocatalytic and Structural Properties of a Highly Engineered Halohydrin Dehalogenase

Schallmey, Marcus,Floor, Robert J.,Hauer, Bernhard,Breuer, Michael,Jekel, Peter A.,Wijma, Hein J.,Dijkstra, Bauke W.,Janssen, Dick B.

, p. 870 - 881 (2013)

Two highly engineered halohydrin dehalogenase variants were characterized in terms of their performance in dehalogenation and epoxide cyanolysis reactions. Both enzyme variants outperformed the wild-type enzyme in the cyanolysis of ethyl (S)-3,4-epoxybutyrate, a conversion yielding ethyl (R)-4-cyano-3-hydroxybutyrate, an important chiral building block for statin synthesis. One of the enzyme variants, HheC2360, displayed catalytic rates for this cyanolysis reaction enhanced up to tenfold. Furthermore, the enantioselectivity of this variant was the opposite of that of the wild-type enzyme, both for dehalogenation and for cyanolysis reactions. The 37-fold mutant HheC2360 showed an increase in thermal stability of 8°C relative to the wild-type enzyme. Crystal structures of this enzyme were elucidated with chloride and ethyl (S)-3,4-epoxybutyrate or with ethyl (R)-4-cyano-3-hydroxybutyrate bound in the active site. The observed increase in temperature stability was explained in terms of a substantial increase in buried surface area relative to the wild-type HheC, together with enhanced interfacial interactions between the subunits that form the tetramer. The structures also revealed that the substrate binding pocket was modified both by substitutions and by backbone movements in loops surrounding the active site. The observed changes in the mutant structures are partly governed by coupled mutations, some of which are necessary to remove steric clashes or to allow backbone movements to occur. The importance of interactions between substitutions suggests that efficient directed evolution strategies should allow for compensating and synergistic mutations during library design.

Synthesis and enzymatic resolution of racemic 2,3-epoxy propyl esters obtained from glycerol

Araujo, Yara Jaqueline Kerber,Avvari, Naga Prasad,Paiva, Derisvaldo Rosa,De Lima, Dênis Pires,Beatriz, Adilson

, p. 1696 - 1698 (2015)

A method is described for the synthesis of (±)-2,3-epoxy propyl esters from glycerol, involving reaction of epichlorohydrin with sodium or potassium salts of carboxylic acids in the presence of TBAB as catalyst, with moderate to excellent yields. Kinetic resolution of glycidyl butyrate by lipase of Thermomyces lanuginosa has been achieved with remarkable enantiomeric excess (ee >99%) using 1,4-dioxane as a co-solvent in pure buffer solution (30 and 50 °C, pH = 7.0).

Isomeric complexes of [RuII(trpy)(L)Cl] (trpy = 2,2′:6′,2″-terpyridine and HL = quinaldic acid): Preference of isomeric structural form in catalytic chemoselective epoxidation process

Chowdhury, Abhishek Dutta,Das, Amit,Irshad,Mobin, Shaikh M.,Lahiri, Goutam Kumar

, p. 1775 - 1785 (2011)

The present work deals with the isomeric complexes of the molecular composition [RuII(trpy)(L)Cl] in 1 and 2 (trpy = 2,2′:6′, 2″-terpyridine, L = deprotonated form of quinaldic acid, HL). Isomeric identities of 1 and 2 have been established by their single-crystal X-ray structures, which reveal that under the meridional configuration of trpy, O - and N donors of the unsymmetrical L are in trans, cis and cis, trans configurations, respectively, with respect to the Ru-Cl bond. Compounds 1 and 2 exhibit appreciable differences in bond distances involving Ru-Cl and Ru-O1/Ru-N1 associated with L on the basis of their isomeric structural features. In relation to isomer 2, the isomeric complex 1 exhibits a slightly lower Ru(II)-Ru(III) oxidation potential [0.35 (1), 0.38 (2) V versus SCE in CH3CN] as well as lower energy MLCT transitions [559 nm and 417 nm (1) and 533 nm and 378 nm (2)]. This has also been reflected in the DFT calculation where a lower HOMO-LUMO gap of 2.59 eV in 1 compared to 2.71 eV in 2 is found. The isomeric structural effect in 1 and 2 has also been prominent in their 1H NMR spectral profiles. The relatively longer Ru-Cl bond in 1 (2.408(2) A) as compared to 2 (2.3813(9) A) due to the trans effect of the anionic O- of coordinated L makes it labile, which in turn facilitates the transformation of [RuII(trpy)(L)(Cl)] (1) to the solvate species, [RuII(trpy)(L)(CH3CN)](Cl) (1a) while crystallizing 1 from the coordinating CH3CN solvent. The formation of 1a has been authenticated by its single-crystal X-ray structure. However, no such exchange of "Cl-" by the solvent molecule occurs in 2 during the crystallization process from the coordinating CH3CN solvent. The labile Ru-Cl bond in 1 makes it a much superior precatalyst for the epoxidation of alkene functionalities. Compound 1 is found to function as an excellent precatalyst for the epoxidation of a wide variety of alkene functionalities under environmentally benign conditions using H 2O2 as an oxidant and EtOH as a solvent, while isomer 2 remains almost ineffective under identical reaction conditions. The remarkable differences in catalytic performances of 1 and 2 based on their isomeric structural aspects have been addressed.

EPOXIDIZATION OF ALLYL CHLORIDE BY COMBINED OXIDATION WITH ETHYLBENZENE ON LAYERED COMPOUNDS OF GRAPHITE WITH TRANSITION-METAL CHLORIDES

Kovtyukhova, N. I.,Belousov, V. M.,Novikov, Yu. N.,Vol'pin, M. E.

, p. 1566 - 1570 (1983)

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Goettig

, p. 2742 (1891)

Physicochemical relationships of the synthesis of epoxy compounds

Sulimov,Danov,Ovcharova,Ovcharov,Flid

, p. 89 - 96 (2015)

Quantitative information on the effect of process parameters on the main relationships of the liquid-phase epoxidation of propylene, allyl chloride, and allyl alcohol with hydrogen peroxide in an organic solvent in the presence of powdered titanium silicalite in a batch reactor was obtained and summarized for the first time. The influence of the solvent amount, reactant ratio, and temperature was examined, and the area of the process parameters ensuring high yields of the epoxy compounds (propylene oxide, epichlorohydrin, and glycidol) was localized.

Continuous dehydrochlorination of 1,3-dichloropropan-2-ol to epichlorohydrin: Process parameters and by-products formation

Krzy?anowska, Anna,Milchert, Eugeniusz

, p. 1218 - 1224 (2013)

The influence of pre-reactor and reactor temperatures on the conversion of 1,3-dichloropropan-2-ol and the selectivity of its transformation to epichlorohydrin in continuous dehydrochlorination for two modes of the reaction product collection was studied. The dehydrochlorination process and mechanism of diglycidyl ether formation are described.

Fully utilizing seeds solution for solvent-free synthesized nanosized TS-1 zeolites with efficient epoxidation of chloropropene

Chai, Yongming,Li, Bin,Li, Yichuan,Liu, Hanfang,Liu, Jia,Liu, Yanru,Ran, Saisai,Wang, Fupeng,Wang, Lei,Wang, Yu,Xie, Huijie,Ye, Tiantian

, (2021/12/27)

Nanosized titanium silicalite-1 (TS-1) demonstrates excellent catalytic ability in the selective catalytic oxidation reaction. However, their synthesis process is usually complicated with low yield under hydrothermal conditions, which is not in line with the concept of green chemistry. Herein, via fully utilizing untreated seeds solution, we report firstly an entirely green strategy for solvent-free synthesizing anatase-free nanosized TS-1 zeolite. The success lies in the fully utilization of seeds solution which is composed of supersaturated structure directing agent (TPAOH), unreacted silica source, water and formed MFI seeds (silicalite-1) without external purification. In the followed solvent-free synthesis of final nanosized TS-1 product, no additional TPAOH is added, which greatly reduces the synthesis cost and synthetic procedure and maintains a high product yield. The obtained nanosized TS-1 zeolite without anatase phase has high crystallinity, large specific surface area. More importantly, the nanosized TS-1 (Si/Ti ?= ?77) catalysts exhibit excellent catalytic ability for the epoxidation of chloropropene with 40.0% conversion and 97.6% selectivity. This sustainable and green synthesis method opens up a new way to regulate nanosized zeolite.

RUTHENIUM COMPLEX AND PRODUCTION METHOD THEREOF, CATALYST, AND PRODUCTION METHOD OF OXYGEN-CONTAINING COMPOUND

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Paragraph 0145-0148, (2021/01/29)

PROBLEM TO BE SOLVED: To provide a ruthenium complex that is particularly useful as a catalyst for oxidizing a substrate having a carbon-hydrogen bond. SOLUTION: The ruthenium complex represented by the general formula (i) or a cis conformer thereof is provided. In the general formula (i), R1 represents H, a phenyl group or a substituted phenyl group; R2 represents H, a phenyl group or an alkyl group; L1 represents halogen or water molecule; L2 represents triphenylphosphine, pyridine, imidazole or dimethylsulfoxide; X represents halogen; and n represents 1 or 2. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPO&INPIT

Selective synthesis of epichlorohydrin: Via liquid-phase allyl chloride epoxidation over a modified Ti-MWW zeolite in a continuous slurry bed reactor

Ding, Luoyi,Yin, Jinpeng,Tong, Wen,Peng, Rusi,Jiang, Jingang,Xu, Hao,Wu, Peng

, p. 331 - 342 (2021/01/11)

The epoxidation of allyl chloride (ALC) to epichlorohydrin (ECH) with H2O2 using a piperidine (PI)-modified Ti-MWW catalyst (Ti-MWW-PI) in a continuous slurry reactor was investigated to develop an efficient reaction system for the corresponding industrial process. The reaction parameters, including solvent, reaction temperature, t-butanol/ALC mass ratio, ALC/H2O2 molar ratio, weight hourly space velocity of H2O2, and the addition amount of ammonia, were studied in detail to pursue high H2O2 conversion and ECH selectivity. A long catalytic lifetime of 244 h was achieved at high H2O2 conversion (>97.0%) and ECH selectivity (>99.8%) under optimized reaction conditions. The crystallinity was well maintained for the deactivated Ti-MWW-PI catalyst, which was regenerated by a combination of calcination and piperidine treatment. This journal is

Epoxidation of Allyl Chloride in the Presence of Tungsten Oxo–Peroxo Heteropoly Compounds of P(V), As(V), and Si(IV) Under Phase-Transfer Catalysis Conditions

Panicheva,Meteleva,Ageikina,Panichev

, p. 1270 - 1274 (2021/10/20)

Abstract: This study investigates the behavior of nonmetals in tungsten oxo–peroxoheteropoly compounds in the reaction of allyl chloride epoxidation. Thecatalytic efficiency in epoxidation was shown to increase in the followingorder: Si(IV) As(V) P(V). Synergism in allyl chloride epoxidation wasdemonstrated for the first time for mixtures of tungsten oxo–peroxo heteropolycompounds of P and As, as well as P and Si. It was also shown that mixturesconsisting of 70% P + 30% Si and 75% P + 25% As exhibit the highest catalyticactivity. Finally, the article suggests a mechanism for the synergisticeffect. [Figure not available: see fulltext.].

A method for efficient preparation of epichlorohydrin by biomass glycerol

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Paragraph 0040-0041; 0051-0052; 0062-0063; 0073, (2022/01/10)

The present invention discloses a method for efficiently preparing epichlorohydrin by biomass glycerol, comprising the following steps: 1) the mass ratio of 1: 0.06 ~ 0.08 of biomass glycerol and a composite catalyst poured into the reactor, and then using an ultrasonic probe to extend into the reactor, 2) step 1) after the end of the reaction, the resulting material is cooled to room temperature and transferred to the reaction vessel, maintaining a temperature of 15 ~ 30 ° C, and then adding an alkaline cyclizer for the reaction; 3) after the completion of the reaction to filter the resulting solids, The filtrate is a solution of epichlorohydrin oxide; the glycerol of the present invention can be completely converted, the intermediate product dichloropropanol yield is high, and the selectivity of collecting 1,3-dichloropropanol is improved, which accelerates the reaction rate; and the process can be co-produced with biodiesel and chlor-alkali industry, and the industrialization prospect is good.

Process route upstream and downstream products

Process route

1-bromo-3-chloro-propan-2-ol
4540-44-7

1-bromo-3-chloro-propan-2-ol

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
1-chloro-3-iodopropan-2-ol
26484-95-7

1-chloro-3-iodopropan-2-ol

hydrogen iodide
10034-85-2

hydrogen iodide

Conditions
Conditions Yield
1,3-Dichloropropane
142-28-9

1,3-Dichloropropane

1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

glycidyl methyl ether
930-37-0

glycidyl methyl ether

1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

2,3-Dichloroprop-1-ene
78-88-6

2,3-Dichloroprop-1-ene

2-chloroallyl alcohol
5976-47-6

2-chloroallyl alcohol

1,2,2-trichloropropane
3175-23-3

1,2,2-trichloropropane

1,2-Dichloropropane
26198-63-0,78-87-5

1,2-Dichloropropane

cis-1,3-Dichloropropene
10061-01-5

cis-1,3-Dichloropropene

1,2,3-trichloro-1-propene
13116-58-0

1,2,3-trichloro-1-propene

(1Z)-1,2,3-trichloroprop-1-ene
96-19-5,13116-58-0,13116-57-9

(1Z)-1,2,3-trichloroprop-1-ene

1,3,3-trichloro-propene
2953-50-6

1,3,3-trichloro-propene

1<i>t</i>,3,3-trichloro-propene
2598-01-8

1t,3,3-trichloro-propene

chlorodibromomethane
124-48-1

chlorodibromomethane

1,1,2-trichloropropane
598-77-6

1,1,2-trichloropropane

2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

1,2,3-trichloropropane
96-18-4

1,2,3-trichloropropane

3,3-dichloropropene
563-57-5

3,3-dichloropropene

3,3-dichloroallyl chloride
2567-14-8

3,3-dichloroallyl chloride

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

allyl alcohol
107-18-6

allyl alcohol

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

chloroacetone
78-95-5

chloroacetone

cyclopentanone
120-92-3

cyclopentanone

chlorobenzene
108-90-7

chlorobenzene

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

(E)-1,3-dichloro-prop-1-ene
10061-02-6

(E)-1,3-dichloro-prop-1-ene

Conditions
Conditions Yield
With sodium hydroxide; water; at 45 - 62.4 ℃; under 112.511 - 750.075 Torr; Product distribution / selectivity;
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With molybdenum blue; dihydrogen peroxide; bis(tri-n-butyltin)oxide; In chloroform; at 25 ℃; for 10h;
1%
48 % Turnov.
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

1,3-Dichloroacetone
534-07-6

1,3-Dichloroacetone

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

Conditions
Conditions Yield
With hydrogenchloride; dihydrogen peroxide; In water; at 30 ℃; for 2h;
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

1-chloro-3-methoxypropan-2-ol
4151-97-7

1-chloro-3-methoxypropan-2-ol

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

Conditions
Conditions Yield
With dihydrogen peroxide; TS-1; In methanol; water; 1,2-dichloro-benzene; at 25 - 40 ℃; for 1h; Product distribution / selectivity;
94%
methanol
67-56-1

methanol

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

1-chloro-3-methoxypropan-2-ol
4151-97-7

1-chloro-3-methoxypropan-2-ol

3-chloro-2-methoxy-propan-1-ol
2858-55-1

3-chloro-2-methoxy-propan-1-ol

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

Conditions
Conditions Yield
With dihydrogen peroxide; In water; at 59.84 ℃; for 2h; Reagent/catalyst; Catalytic behavior;
1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

epifluorohydrine
503-09-3

epifluorohydrine

1,3-difluoro-2-propanol
453-13-4

1,3-difluoro-2-propanol

1-chloro-3-fluoroisopropanol
146580-24-7,453-11-2

1-chloro-3-fluoroisopropanol

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

Conditions
Conditions Yield
With potassium fluoride; at 80 ℃; for 0.5h; under 750.075 Torr; Reagent/catalyst; Temperature; Inert atmosphere;
1,2-Dichloropropane
26198-63-0,78-87-5

1,2-Dichloropropane

epifluorohydrine
503-09-3

epifluorohydrine

1,3-difluoro-2-propanol
453-13-4

1,3-difluoro-2-propanol

1-chloro-3-fluoroisopropanol
146580-24-7,453-11-2

1-chloro-3-fluoroisopropanol

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

Conditions
Conditions Yield
With potassium fluoride; at 95 ℃; for 24.7h; under 750.075 Torr; Time; Inert atmosphere;
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

Conditions
Conditions Yield
With hydrogenchloride; dihydrogen peroxide; In water; at 30 ℃; for 2h; Reagent/catalyst; Temperature; Catalytic behavior; Green chemistry;

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