GB788531A - Diepoxides and process of producing the same - Google Patents
Diepoxides and process of producing the sameInfo
- Publication number
- GB788531A GB788531A GB8245/55A GB824555A GB788531A GB 788531 A GB788531 A GB 788531A GB 8245/55 A GB8245/55 A GB 8245/55A GB 824555 A GB824555 A GB 824555A GB 788531 A GB788531 A GB 788531A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- allyl
- group
- mixture
- solution
- 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
-
- 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
- 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
- C07D303/48—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
An alkenyl ester of a diepoxy fatty acid is obtained by reacting peracetic acid with an alkenyl ester of a dienoic fatty acid at a temperature within the range of - 10 DEG C. to 75 DEG C. The invention also comprises as new products vinyl 9, 10, 12, 13 diepoxystearate and allyl 9, 10, 12, 13 diepoxystearate. In the epoxidation process it is preferred to provide an excess of from 10 to 25 mol. per cent peracetic acid in the reaction mixture and to use the peracetic acid in the form of a solution thereof in an inert volatile organic solvent, e.g. acetone. After the reaction is complete the solvent is removed from the mixture and acetic acid and any unconsumed peracetic acid are then removed, e.g. by distillation or extraction. The preferred method of separation is to add the reaction mixture to a kettle-still containing ethylbenzene which is refluxing at about 25 mm. of Hg. pressure and then distilling off the volatile solvent (e.g. acetone), peracetic acid, acetic acid, and ethylbenzene. The residue product may be further purified by continuous distillation at pressures of from one to two mm. of Hg. Examples are given for the epoxidation of: (1) the allyl ester obtained by esterifying a commercial mixture of fatty acids consisting of oleic acid and linoleic acid and small amounts of linolenic acid and of saturated acids above lauric acid with allyl alcohol in the presence of toluene and concentrated sulphuric acid as catalyst; and (2) the allyl ester of linoleic acid (obtained from safflower oil), the allyl ester being obtained by esterifying linoleic acid with allyl alcohol in the presence of benzene and of concentrated sulphuric acid as catalyst. The epoxidation is carried out by means of a solution of peracetic acid in acetone and the epoxidized product is recovered as above by adding the reaction mixture to a kettle still containing ethyl benzene refluxing at 25 mm. Hg. pressure. Purified allyl 9,10,12,13-diepoxy stearate is recovered in (2) and it is stated that vinyl linoleate can be epoxidized in a similar manner to yield vinyl 9,10,12, 13-diepoxystearate. The diepoxides are stated to be useful as plasticizers and stabilizers for synthetic resins and to be capable of forming polymers (see Group IV (a)) having a diversity of properties on account of the presence in the monomer of epoxide groups and an olefinic group. The linoleic acid used in Example (2) is prepared by refluxing safflower oil with a solution of KOH in methanol for two hours and then removing the methanol by distillation. Water and cold dilute sulphuric acid are added to the residue and the fatty acid layer is separated, washed with hot water, filtered while hot, and then dried at 140 DEG C. The resulting crude acid mixture is then added to a solution of urea in hot methanol and the mixture is heated to effect complete solution and then cooled and filtered. Methanol is evaporated from the filtrate and water is then added followed by a small amount of concentrated HCl. After heating for a short period the water layer is drained off from the acid layer and the latter distilled twice through a packed column to yield a product analysing 96.2 per cent as linoleic acid. Specification 788,530 is referred to.ALSO:Alkenyl esters of diepoxy fatty acids, e.g. allyl and vinyl 9,10,12,13-diepoxystearates, which are obtainable by reacting peracetic acid with an alkenyl ester of a dienoic fatty acid (see Group IV (b)) are stated to be useful as plasticizers and stabilizers for synthetic resins. They may be polymerized to form insoluble and infusible polymers. Since the esters contain an epoxide group and an olefinic group, they can be subjected to conditions whereby polymerization occurs only through one type of group and the resulting polymer can then be further polymerized under different conditions through the second type of group to form an infusible and insoluble polymer. Specification 788,530 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US788531XA | 1954-03-25 | 1954-03-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB788531A true GB788531A (en) | 1958-01-02 |
Family
ID=22146595
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8245/55A Expired GB788531A (en) | 1954-03-25 | 1955-03-22 | Diepoxides and process of producing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB788531A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0604364A2 (en) * | 1992-12-23 | 1994-06-29 | Ciba-Geigy Ag | New (cyclo)aliphatic epoxy compounds |
-
1955
- 1955-03-22 GB GB8245/55A patent/GB788531A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0604364A2 (en) * | 1992-12-23 | 1994-06-29 | Ciba-Geigy Ag | New (cyclo)aliphatic epoxy compounds |
EP0604364A3 (en) * | 1992-12-23 | 1995-01-04 | Ciba Geigy Ag | New (cyclo)aliphatic epoxy compounds. |
US5468886A (en) * | 1992-12-23 | 1995-11-21 | Ciba-Geigy Corporation | (Cyclo)aliphatic epoxy compounds |
AU672645B2 (en) * | 1992-12-23 | 1996-10-10 | Vantico Ag | Novel (cyclo)aliphatic epoxy compounds |
US5599651A (en) * | 1992-12-23 | 1997-02-04 | Ciba-Geigy Corporation | (Cyclo)aliphatic epoxy compounds |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2482761A (en) | Polymerization of unsaturated fatty acids | |
US2411567A (en) | Manufacture of carboxylic acid anhydrides | |
US2482760A (en) | Purification of oleic acid | |
US2391226A (en) | Method of preparing a cyclic dicarboxylic acid anhydride | |
US2921957A (en) | Process for the production of fluoroesters | |
US2371281A (en) | Lactyuactic esters and process of | |
US2779771A (en) | Higher fatty ester diepoxides and process of producing the same | |
Danzig et al. | Reactions of conjugated fatty acids. V. Preparation and properties of diels‐alder adducts and their esters from trans, trans‐conjugated fatty acids derived from soybean oil | |
US2372409A (en) | Process for preparing 2-oxazolines | |
US2467926A (en) | Preparation of monomeric alkyl alpha-cyano-acrylates | |
US2441183A (en) | Hexahydrobenzyl ester | |
GB788531A (en) | Diepoxides and process of producing the same | |
GB903613A (en) | Improvements in or relating to the production of acetoacetic acid esters | |
US2229997A (en) | Process for the manufacture of tetrahydrofurfuryl acrylate and its polymers | |
US2312298A (en) | Process of preparing esters of | |
KR102109134B1 (en) | Method for preparing monoglycerides | |
US2373583A (en) | Conversion of methyl formate to formic acid | |
US2755303A (en) | Polymerizable esters | |
US2340268A (en) | Esters of nitrohydroxy compounds | |
US3147236A (en) | Epoxy monomers and resins thereof | |
US2738356A (en) | Nortricyclyl esters | |
US2457300A (en) | Lower polymer of glycidyl sorbate and method of making it | |
US2897231A (en) | Method for the recovery of azelaic acid from a mixture of oxidized acids | |
US2374484A (en) | Esters of nitrohydroxy compounds | |
GB834029A (en) | Allyl 3, 4-epoxy-2-hydroxyalkanoates and process for preparing the same |