GB784620A - Manufacture of aliphatic chloroepoxides - Google Patents

Manufacture of aliphatic chloroepoxides

Info

Publication number
GB784620A
GB784620A GB16537/55A GB1653755A GB784620A GB 784620 A GB784620 A GB 784620A GB 16537/55 A GB16537/55 A GB 16537/55A GB 1653755 A GB1653755 A GB 1653755A GB 784620 A GB784620 A GB 784620A
Authority
GB
United Kingdom
Prior art keywords
chloride
epoxybutane
acid
peracetic
butene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB16537/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Union Carbide Corp filed Critical Union Carbide Corp
Publication of GB784620A publication Critical patent/GB784620A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Epoxy Compounds (AREA)

Abstract

Aliphatic chlorepoxides are manufactured by reacting an allylic chlorohydrocarbon containing the group: <FORM:0784620/IV (a)/1> with peracetic or perpropionic acid substantially free from hydrogen peroxide, water, mineral acids and salts, preferably at 25-200 DEG C. Advantageously the allylic chlorohydrocarbon is heated to refluxing temperature and the peracetic or perpropionic acid is gradually added, if desired in admixture with acetaldehyde and/or acetone. To prevent decomposition of the peracid by heavy metal ions during the reaction, it may be carried out in the presence of a sequestering agent (e.g. an alkali metal salt of a polyphosphate or partially esterified polyphosphate, gluconic acid, ethylenediaminetetracetic acid or sodium silicate) or of a compound which inhibits the decomposition (e.g. pyrogallol, trinitrobenzene or sodium pyrophosphate). Preferred starting materials are compounds containing either one or two chlorine atoms in the allylic position but none attached directly to either of the olefinic carbon atoms, and having the general formula: <FORM:0784620/IV (a)/2> wherein R1, R2, R3, R4 and R5 represent hydrogen or alkyl or chloroalkyl radicals. Examples describe the preparation, using peracetic acid, of chloroisobutylene oxide from methallyl chloride, 3 - chloro - 1 : 2 - epoxybutane from 3 - chloro - 1 - butene, 1 : 4 - dichloro - 2 : 3-epoxybutane from 1 : 4-dichloro-2-butene, epichlorhydrin from allyl chloride, 3 : 4-dichloro1 : 2-epoxybutane from 3 : 4-dichloro-1-butene and 2 : 3-epoxy-2-ethylhexyl chloride from 2-ethyl-2-hexenyl chloride; and the preparation of 1-chloro-2 : 3-epoxybutane from crotyl chloride and perpropionic acid. Starting materials. Peracetic and perpropionic acids of the desired degree of purity are prepared by treating acetaldehyde and propionaldehyde respectively with oxygen at a low temperature, advantageously in the presence of a catalytic amount of a heavy metal salt or under ultra-violet irradiation, thermally decomposing the resulting acetaldehyde monoperacetate or propionaldehyde monoperpropionate, and rapidly separating the resulting peracid from the simultaneously liberated aldehyde. The preparation of each of the peracids is described in detail. 2-Ethyl-2-hexenyl chloride is prepared by treating 2-ethyl-2-hexenol with thionyl chloride in the presence of pyridine.
GB16537/55A 1954-06-28 1955-06-08 Manufacture of aliphatic chloroepoxides Expired GB784620A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US784620XA 1954-06-28 1954-06-28

Publications (1)

Publication Number Publication Date
GB784620A true GB784620A (en) 1957-10-09

Family

ID=22144173

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16537/55A Expired GB784620A (en) 1954-06-28 1955-06-08 Manufacture of aliphatic chloroepoxides

Country Status (1)

Country Link
GB (1) GB784620A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2060190A1 (en) * 1970-12-08 1972-07-06 Degussa Process for epoxidizing unsaturated compounds
US4944847A (en) * 1989-06-12 1990-07-31 Nalco Chemical Company Method for inhibiting epichlorohydrin fouling

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2060190A1 (en) * 1970-12-08 1972-07-06 Degussa Process for epoxidizing unsaturated compounds
US4944847A (en) * 1989-06-12 1990-07-31 Nalco Chemical Company Method for inhibiting epichlorohydrin fouling

Similar Documents

Publication Publication Date Title
McKillop et al. Sodium perborate and sodium percarbonate: Cheap, safe and versatile oxidising agents for organic synthesis
US2448252A (en) Preparation of peracid solutions
US4303587A (en) Catalytic epoxidation of olefins
FR2479825B1 (en)
US2284477A (en) Preparation of peracids
GB784620A (en) Manufacture of aliphatic chloroepoxides
US2692271A (en) Method of epoxidation
GB791875A (en) Process for the preparation of per-fatty acids
JPS61115075A (en) Manufacture of storable benzthiazole sulfenamides
GB1498365A (en) Process for preparing 3-oxy-4h-pyran-4-one derivatives
GB1014361A (en) Improvements in and relating to the production of aliphatic per-acids
US3265716A (en) Epoxidation of olefins during the simultaneous air oxidation of secondary aldehydes
US4024165A (en) Process for the epoxidation of olefins
MX9304140A (en) PURINE SALT, PROCESS FOR ITS PREPARATION AND PROCESS FOR PREPARING AN ANTIVIRAL AGENT THROUGH THE REACTION OF SUCH SALT.
GB1585011A (en) Process for the epoxidation of olefins
FR2500453B1 (en)
CH610318A5 (en) Catalytic process for the epoxidation of an olefin
US3159655A (en) 1, 1-dihalo-2-oxirane derivatives of cyclopropane
US3113951A (en) Epoxidation of olefins with hydrogen peroxide and a cyanamide
US2992237A (en) Process for the production of com-
ES367096A1 (en) (1,2-epoxypropyl)phosphonous acid derivatives
ES393839A1 (en) Process for the preparation of percarboxylic acids
GB889652A (en) Liquid washing agent incorporating glycol derivatives containing peroxide groups
US5157131A (en) Epoxides and a process for their preparation
US3419621A (en) Halogen containing ether compositions