GB911884A - Process for the oxidation and simultaneous esterification of unsaturated fatty acids - Google Patents
Process for the oxidation and simultaneous esterification of unsaturated fatty acidsInfo
- Publication number
- GB911884A GB911884A GB19626/59A GB1962659A GB911884A GB 911884 A GB911884 A GB 911884A GB 19626/59 A GB19626/59 A GB 19626/59A GB 1962659 A GB1962659 A GB 1962659A GB 911884 A GB911884 A GB 911884A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fatty acids
- products
- acids
- low pressure
- hydrogen peroxide
- 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
- 235000021122 unsaturated fatty acids Nutrition 0.000 title abstract 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 title abstract 3
- 230000032050 esterification Effects 0.000 title abstract 2
- 238000005886 esterification reaction Methods 0.000 title abstract 2
- 230000003647 oxidation Effects 0.000 title abstract 2
- 238000007254 oxidation reaction Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- -1 undecylenic Chemical group 0.000 abstract 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 6
- 239000004698 Polyethylene Substances 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- 229920000573 polyethylene Polymers 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- 229960000583 acetic acid Drugs 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- 230000002378 acidificating effect Effects 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 235000019438 castor oil Nutrition 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 2
- 125000005481 linolenic acid group Chemical group 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 150000002739 metals Chemical class 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- 230000000737 periodic effect Effects 0.000 abstract 2
- 230000008961 swelling Effects 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000012153 distilled water Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 229940093915 gynecological organic acid Drugs 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/18—Quaternary ammonium compounds
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Products of the simultaneous oxidation and esterification of unsaturated fatty acids containing 10 to 22 carbon atoms such as undecylenic, oleic, linoleic, linolenic acids and castor oil fatty acids, with hydrogen peroxide and glacial acetic acid or acetic anhydride, (Group IV(b)), are used as swelling agents for low pressure polyethylene, or in the form of ammonium or alkali metal salts as emulsifying agents, or as their compounds with metals of the second to fourth Periodic Groups for improving and stabilizing low pressure polyethylene.ALSO:Unsaturated fatty acids containing 10 to 22 carbon atoms such as undecylenic, oleic, linolenic acids and castor oil fatty acids, are oxidised and esterified simultaneously with hydrogen peroxide, added portionwise, and glacial acetic acid or acetic anhydride, in the presence of an acidic catalyst and at elevated temperature to yield products with iodine number below 3 and an epoxy-oxygen content below 0.5%. For every mole of double bond of the acid at least one mole of hydrogen peroxide, 0.5-0.6 mol of anhydrous acetic acid and 1.5 to 8.5 grams of catalyst are used and the final product is washed with distilled water at 40-48 DEG C. until free from catalyst. Strong inorganic or organic acids such as phosphoric, ethyl sulphuric and p-toluene sulphonic acids, or strongly acidic ion-exchange resins are used as catalysts and the temperature may be between 40 DEG and 95 DEG C. The products are soluble in cold aqueous alkali or dilute aqueous ammonia at a pH 8, and are pale coloured products suitable as swelling agents for polyethylene or as ammonia or alkali metal salts, as emulsifying agents, or in the form of their compounds with metals of the second to fourth groups of the periodic system as stabilizers for low pressure polyethylene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEW23460A DE1107657B (en) | 1958-06-07 | 1958-06-07 | Process for the production of products used as swelling, remediation or stabilizing agents for plastics and as starting materials for the production of emulsifiers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB911884A true GB911884A (en) | 1962-11-28 |
Family
ID=7597588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19626/59A Expired GB911884A (en) | 1958-06-07 | 1959-06-08 | Process for the oxidation and simultaneous esterification of unsaturated fatty acids |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1107657B (en) |
| GB (1) | GB911884A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003047630A2 (en) * | 2001-12-04 | 2003-06-12 | Bertha Andras | Method for oxygen treatment of unsaturated carbon compounds, novel epoxy-structured material obtained by the method, apparatus for carrying out the method and a therapeutic composition using the material |
-
1958
- 1958-06-07 DE DEW23460A patent/DE1107657B/en active Pending
-
1959
- 1959-06-08 GB GB19626/59A patent/GB911884A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003047630A2 (en) * | 2001-12-04 | 2003-06-12 | Bertha Andras | Method for oxygen treatment of unsaturated carbon compounds, novel epoxy-structured material obtained by the method, apparatus for carrying out the method and a therapeutic composition using the material |
| WO2003047630A3 (en) * | 2001-12-04 | 2003-09-12 | Andras Bertha | Method for oxygen treatment of unsaturated carbon compounds, novel epoxy-structured material obtained by the method, apparatus for carrying out the method and a therapeutic composition using the material |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1107657B (en) | 1961-05-31 |
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