GB877632A - Improvements in and relating to epoxidation - Google Patents
Improvements in and relating to epoxidationInfo
- Publication number
- GB877632A GB877632A GB41620/59A GB4162059A GB877632A GB 877632 A GB877632 A GB 877632A GB 41620/59 A GB41620/59 A GB 41620/59A GB 4162059 A GB4162059 A GB 4162059A GB 877632 A GB877632 A GB 877632A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- unsaturated compounds
- olefines
- unsaturation
- aliphatic
- 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
- 238000006735 epoxidation reaction Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 hydroxy, carboxyl Chemical group 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 239000000370 acceptor Substances 0.000 abstract 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 abstract 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 abstract 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 abstract 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 abstract 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 abstract 1
- 239000005062 Polybutadiene Substances 0.000 abstract 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003172 aldehyde group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 abstract 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 abstract 1
- 229930006739 camphene Natural products 0.000 abstract 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229940087305 limonene Drugs 0.000 abstract 1
- 235000001510 limonene Nutrition 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical class CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 abstract 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 abstract 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 229920002857 polybutadiene Polymers 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000004760 silicates Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 abstract 1
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
- C07D303/04—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
- C07D303/48—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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Ethylenically unsaturated compounds are epoxidized by reacting with a preformed percarboxylic acid having not more than 10 carbon atoms in the molecule in the presence of sufficient acid acceptor to neutralise 15% to 80% of the acid present in the reaction mixture. The reaction is effected at -10 DEG C. to +80 DEG C. for 1/2 to 8 hours and the peracid is employed in an amount sufficient to epoxidize all desired unsaturation. Preferred starting materials are the 4 to 6 carbon aliphatic and cyclo-aliphatic olefines such as pentene and cyclohexene. Olefines which carry alkyl and aromatic hydrocarbon-substituents on carbons alpha to the unsaturation are exemplified by a -methyl styrene, limonene, a -pinene, myrcene, allooccimene, diisobutylene, camphene, polybutadiene, copolymers of butadiene with other unsaturated compounds, tripropylene and tetrapropylene. The unsaturated compounds may also carry hydroxy, carboxyl, sulphonic acid, halogen or aldehyde groups. Thus the process may be used to form epoxides of fatty acid esters. Typical acid acceptors are the alkali and alkaline earth metal hydroxides, carbonates, bicarbonates, acetates, propionates, butyrates, valerates, caproates, caprylates, pelargonates, phosphates, silicates and borates. The preferred percarboxylic acids are performic, peracetic, percyclohexanoic, perpelargonic.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US877632XA | 1958-12-09 | 1958-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB877632A true GB877632A (en) | 1961-09-20 |
Family
ID=22207099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB41620/59A Expired GB877632A (en) | 1958-12-09 | 1959-12-08 | Improvements in and relating to epoxidation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB877632A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3235568A (en) * | 1961-03-20 | 1966-02-15 | Swift & Co | Epoxy polyamides |
| US3979425A (en) | 1967-06-15 | 1976-09-07 | Firmenich S.A. | Process for the preparation of unsaturated aldehydes |
| US4882442A (en) * | 1980-12-30 | 1989-11-21 | Peroxid-Chemie Gmbh | Process for the production of epoxides |
-
1959
- 1959-12-08 GB GB41620/59A patent/GB877632A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3235568A (en) * | 1961-03-20 | 1966-02-15 | Swift & Co | Epoxy polyamides |
| US3979425A (en) | 1967-06-15 | 1976-09-07 | Firmenich S.A. | Process for the preparation of unsaturated aldehydes |
| US4882442A (en) * | 1980-12-30 | 1989-11-21 | Peroxid-Chemie Gmbh | Process for the production of epoxides |
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