Epichlorohydrin

Base Information

• Chemical Name: Epichlorohydrin
• CAS No.: 106-89-8
• Deprecated CAS: 109351-74-8,13403-37-7,36250-81-4,9009-12-5,61630-87-3,209008-81-1,209008-82-2,95522-44-4,117277-19-7,1286163-93-6,95522-43-3,2232867-15-9,2480253-11-8,13403-37-7,36250-81-4
• Molecular Formula: C3H5ClO
• Molecular Weight: 92.5251
• Hs Code.: 2932999099
• European Community (EC) Number: 203-439-8
• ICSC Number: 0043
• NSC Number: 6747
• UN Number: 2023
• UNII: 08OOR508C0
• DSSTox Substance ID: DTXSID1020566
• Nikkaji Number: J4.037A
• Wikipedia: Epichlorohydrin
• Wikidata: Q423083
• NCI Thesaurus Code: C44381
• Metabolomics Workbench ID: 144475
• ChEMBL ID: CHEMBL1421613
• Mol file: 106-89-8.mol

Synonyms:Epichlorhydrin;Epichlorohydrin;Epichlorohydrin, (+-)-Isomer;Epichlorohydrin, (S)-Isomer

Chemical Property of Epichlorohydrin

Chemical Property:

• Appearance/Colour: clear, colorless
• Vapor Pressure: 22mmHg at 25°C
• Melting Point: -57 °C
• Refractive Index: n20/D 1.438(lit.)
• Boiling Point: 116.1 °C at 760 mmHg
• Flash Point: 33.9 °C
• PSA: 12.53000
• Density: 1.205 g/cm³
• LogP: 0.62400
• Water Solubility.: 6 g/100 mL (10℃)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 92.0028925
• Heavy Atom Count: 5
• Complexity: 37.9
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T:Toxic
• Statements: R10:; R23/24/25:; R34:; R43:; R45:
• Safety Statements: S45:; S53:

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Epoxides
• Canonical SMILES: C1C(O1)CCl
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of the vapour may cause lung oedema. The effects may be delayed. Medical observation is indicated. Inhalation of the vapour may cause asthma-like reactions. The substance may cause effects on the central nervous system, kidneys and liver. This may result in convulsions, kidney impairment and liver impairment. Exposure at high levels could cause death.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the kidneys, liver and lungs. This may result in impaired functions. May cause heritable genetic damage to human germ cells. This substance is probably carcinogenic to humans.

Technology Process of Epichlorohydrin

There total 63 articles about Epichlorohydrin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(C4H9)3SnOCH(CH2Cl)2 (35952-61-5) → tributyltin chloride (1461-22-9) + chloroacetone (78-95-5) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7)

Guidance literature:

63% decompn. at 210°C (1 h);

DOI:10.1016/S0022-328X(00)86886-2

Reference yield: 94.0%

3-chloroprop-1-ene (107-05-1) → 1-chloro-3-methoxypropan-2-ol (4151-97-7) + 3-monochloro-1,2-propanediol (96-24-2) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7)

Guidance literature:

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

Reference yield: 80.5%

1,3-Dichloro-2-propanol (96-23-1) → chloroacetone (78-95-5) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7)

Guidance literature:

With HT₄-c823; In water; at 149.84 ℃; for 0.5h; under 750.075 Torr; Reagent/catalyst; Temperature; chemoselective reaction; Catalytic behavior; Flow reactor;

DOI:10.1039/c7gc02610b

upstream raw materials:

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

2,3-Dichloro-1-propanol

1,3-Dichloro-2-propanol

1,3-dichloro-2-acetoxypropane

Downstream raw materials:

2-hydroxy-3-chloropropylamine

1-bromo-2-benzyloxy-3-chloropropane

2-benzyl-4-chloromethyl[1,3]dioxolane

1,2-diacetoxy-3-chloro-propane

Refernces

• 1、 Siewniak, Agnieszka,Jasiak-Jaroń, Katarzyna,Kotyrba, ?ukasz,Baj, Stefan. "Efficient Catalytic System Involving Molybdenyl Acetylacetonate and Immobilized Tributylammonium Chloride for the Direct Synthesis of Cyclic Carbonates from Carbon Dioxide and Olefins". . p. 1567 - 1573. Retrieved 2017.
• 2、 Panicheva,Meteleva,Ageikina,Panichev. "Phase Transfer of the Organic Substrate in the Epoxidation Reaction of Allyl Chloride in Two-Phase Aqueous–Organic Systems". . p. 884 - 888. Retrieved 2018.
• 3、 Gao, Huanxin,Suo, Jishuan,Li, Shuben. "An Easy Way to Prepare Titanium Silicalite-1 (TS-1)". . p. 835 - 836. Retrieved 1995.
• 4、 Peng, Xinxin,Xia, Changjiu,Lin, Min,Shu, Xingtian,Zhu, Bin,Wang, Baorong,Zhang, Yao,Luo, Yibin,Mu, Xuhong. "A safer and greener chlorohydrination of allyl chloride with H2O2 and HCl over hollow titanium silicate zeolite". . p. 17 - 25. Retrieved 2017.
• 5、 Sulimov,Danov,Ovcharova,Ovcharov,Flid. "Kinetics of allyl chloride epoxidation with hydrogen peroxide catalyzed by extruded titanium silicalite". . p. 712 - 721. Retrieved 2014.
• 6、 Taghiyar, Hamid,Yadollahi, Bahram. "New perspective to catalytic epoxidation of olefins by Keplerate containing Keggin polyoxometalates". . p. 98 - 104. Retrieved 2018.
• 7、 Bogdal,Lukasiewicz,Pielichowski,Bednarz. "Microwave-assisted epoxidation of simple alkenes in the presence of hydrogen peroxide". . p. 2973 - 2983. Retrieved 2005.
• 8、 Peng,Lu,Ma,Shen,Wei,He,Zhou,Xia. "Highly efficient epoxidation of cyclohexene with aqueous H2O2 over powdered anion-resin supported solid catalysts". . p. 393 - 399. Retrieved 2016.
• 9、 Cui, Yu,Jiang, Xuchuan,Sun, Guoxin,Sun, Junhua,You, Qi,Zhao, Xiuxian. "Epoxidation of allyl chloride with H2O2 catalyzed by three structurally related quaternary ammonium modified polyoxophosphotungstates". . . Retrieved 2020.
• 10、 Schallmey, Marcus,Floor, Robert J.,Hauer, Bernhard,Breuer, Michael,Jekel, Peter A.,Wijma, Hein J.,Dijkstra, Bauke W.,Janssen, Dick B.. "Biocatalytic and Structural Properties of a Highly Engineered Halohydrin Dehalogenase". . p. 870 - 881. Retrieved 2013.