GB784620A - Manufacture of aliphatic chloroepoxides - Google Patents
Manufacture of aliphatic chloroepoxidesInfo
- 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
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.
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)
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 |
-
1955
- 1955-06-08 GB GB16537/55A patent/GB784620A/en not_active Expired
Cited By (2)
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 |
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