GB788530A - Epoxides and method of making the same - Google Patents
Epoxides and method of making the sameInfo
- Publication number
- GB788530A GB788530A GB7909/55A GB790955A GB788530A GB 788530 A GB788530 A GB 788530A GB 7909/55 A GB7909/55 A GB 7909/55A GB 790955 A GB790955 A GB 790955A GB 788530 A GB788530 A GB 788530A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- group
- allyl
- epoxy
- per cent
- 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
- 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
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- 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
-
- 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)
Abstract
The invention comprises epoxy compounds having the general formula: <FORM:0788530/IV (b)/1> wherein R1 is a hydrogen atom or an alkyl group containing from 1 to 14 carbon atoms, R2 is a straight chain alkylene group containing from 1 to 15 carbon atoms and having a CH2 group adjacent to the carbonyl radical, the sum of the carbon atoms in R1 and R2 being from 7 to 15, and R represents a vinyl or an allyl group. The compounds may be obtained by reacting peracetic acid in an inert volatile organic solvent, e.g. acetone, with an alkenyl ester of a monoethylenic fatty acid of the formula R1-CH = CH-R2-COOR, wherein R, R1, R2 and the sum of the carbon atoms in R1 and R2 are as defined above, at a temperature within the range of - 10 DEG C. to 75 DEG C. and recovering the epoxy compound formed. The monoethylenic fatty acids used to form the ester starting materials are those containing from 10 to 18 carbon atoms per molecule, e.g. the decenoic, undecenoic, dodecenoic and hexadecenoic acids, and the octadenoic acids, e.g. oleic acid or elaidic acid. Mixtures of fatty acids containing a monoethylenic fatty acid having 10 to 18 carbon atoms can also be employed. The epoxidation can be carried out by charging the unsaturated ester to a reaction vessel and then adding gradually a solution of peracetic acid in a volatile organic solvent and it is preferred to maintain the reaction temperature at from 25 DEG to 50 DEG C. After the reaction is complete any excess peracetic acid and acetic acid is removed from the reaction vessel, e.g. by distillation or extraction, but it is preferred to add the reaction mixture to a kettle still containing an inert volatile organic solvent, e.g. ethylbenzene, which is refluxing at a pressure of about 25 millimetres of mercury and then distill off peracetic acid, acetic acid, ethylbenzene solvent (e.g. acetone) and any low boiling material. The residue product may then be purified by further distillation, e.g. by continuous low pressure distillation. Examples are given for the preparation of (1) allyl 9, 10-epoxy stearate; (2) vinyl 9,10-epoxy stearate; (3) mixed allyl esters of epoxy and saturated fatty acids by epoxidation with peracetic acid in acetone of the mixed allyl esters derived from a commercial mixture of fatty acids having the approximate composition oleic acid (46 per cent), palmitic acid (25 per cent), stearic acid (17 per cent), myristic acid (3 per cent), linoleic acid (8 per cent), linolenic acid (1 per cent) and small amounts of unsaponifiable constituents; (4) allyl esters of mixed epoxy and saturated fatty acids by epoxidation of the mixed allyl esters derived from a commercial mixture of fatty acids consisting of oleic acid (41 per cent), linoleic acid (54 per cent), linolenic acid (2 per cent) and saturated acids higher than lauric acid (3 per cent); (5) allyl trans-9,10-epoxy stearate by epoxidation of allyl elaidate; and (6) allyl-10,11-epoxyundecanoate by epoxidation of the allyl ester of 10-undecylenic acid. It is stated that vinyl 10,11-epoxyundecanoate can be obtained by epoxidation of vinyl 10-undecylenate. The allyl esters used in examples (1), (3) and (4) are obtained by refluxing, with removal of water at the still head, the appropriate fatty acid or fatty acid mixture with allyl alcohol in the presence of toluene and concentrated sulphuric acid as catalyst. In (5) and (6) the allyl esters are obtained similarly except that in (5) p-toluene sulphonic acid is used as catalyst whilst in (6) benzene is used instead of toluene. The vinyl oleate used in Example (2) is obtained by reacting vinyl acetate and oleic acid in the presence of mercuric sulphate and vinyl 10,11-undecylenate may be obtained similarly. The epoxy esters may be polymerized by themselves or may be copolymerized with other compounds (see Group IV (a)) and since they contain an epoxide group and an olefinic group they may be subjected to conditions whereby polymerization occurs through one group to the exclusion of polymerization through the second group and the resulting polymer can then be further polymerized through the unaffected second group. Specification 788,531 and U.S.A. Specification 2,559,177 are referred to.ALSO:Epoxy compounds having the general formula <FORM:0788530/IV (a)/1> wherein R1 is a hydrogen atom or an alkyl group containing 1 to 14 carbon atoms, R2 is a straight chain alkylene group containing from 1 to 15 carbon atoms and having a CH2 group adjacent to the carbonyl radical, the sum of the carbon atoms in R1 and R2 being from 7 to 15, and R represents a vinyl group or an allyl group, e.g. vinyl and allyl 9,10-epoxy-stearates and 10, 11-epoxy-undecanoates, (see Group IV (b)), may be polymerized with themselves or copolymerized with other compounds which are copolymerizable therewith by virtue of the unsaturated group. Since the monomers contain an expoxide group and an olefinic group they may 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. The monomers are useful as plasticizers, stabilizers, and crosslinking agents for various types of synthetic resins.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US788530XA | 1954-03-25 | 1954-03-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB788530A true GB788530A (en) | 1958-01-02 |
Family
ID=22146594
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7909/55A Expired GB788530A (en) | 1954-03-25 | 1955-03-18 | Epoxides and method of making the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB788530A (en) |
-
1955
- 1955-03-18 GB GB7909/55A patent/GB788530A/en not_active Expired
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