GB1032363A - Improvements in or relating to the preparation of di-or tri-basic acids and derivatives thereof - Google Patents
Improvements in or relating to the preparation of di-or tri-basic acids and derivatives thereofInfo
- Publication number
- GB1032363A GB1032363A GB3559262A GB3559262A GB1032363A GB 1032363 A GB1032363 A GB 1032363A GB 3559262 A GB3559262 A GB 3559262A GB 3559262 A GB3559262 A GB 3559262A GB 1032363 A GB1032363 A GB 1032363A
- Authority
- GB
- United Kingdom
- Prior art keywords
- conjugated
- fatty acids
- products
- methyl esters
- maleic
- 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
- 239000002253 acid Substances 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000004135 Bone phosphate Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 3
- 229930195729 fatty acid Natural products 0.000 abstract 3
- 239000000194 fatty acid Substances 0.000 abstract 3
- 150000004665 fatty acids Chemical class 0.000 abstract 3
- 150000004702 methyl esters Chemical class 0.000 abstract 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 235000019438 castor oil Nutrition 0.000 abstract 2
- 230000003197 catalytic effect Effects 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
- 239000000203 mixture Substances 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 244000020551 Helianthus annuus Species 0.000 abstract 1
- 235000003222 Helianthus annuus Nutrition 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 239000003784 tall oil Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 1
Classifications
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/58—Esters of straight chain acids with eighteen carbon atoms in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F242/00—Copolymers of drying oils with other monomers
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09G—POLISHING COMPOSITIONS; SKI WAXES
- C09G1/00—Polishing compositions
- C09G1/06—Other polishing compositions
- C09G1/08—Other polishing compositions based on wax
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
Abstract
Mixtures of conjugated and non-conjugated unsaturated fatty acids, esters, alcohols, amines or amides including as the predominant component free or combined mixed positional and geometrical isomers of the conjugated compounds are heated with a reactive dienophile in an amount equivalent to the conjugated diene content of the mixture, in the presence of catalytic amounts of iodine and in the absence of U.V. light. The products are Diels-Alden adducts and dienophiles mentioned are maleic acid or anhydride, acrylonitrile, actylic acid, methyl acrylate, and acrolein and the conjugated materials may be dehydrated castor oil fatty acids, and isomerized unsaturated fatty products obtained by the catalytic isomerization of polyunsaturated oils. Solvents and polymerization inhibitors may be used and the products may be separated by distillation or solvent extraction. Examples describe the reaction of conjugated soya fatty acids with maleic anhydrides, conjugated tall oil methyl esters with acrylic acid, conjugated soya methyl esters with methyl acrylate, dehydrated castor oil fatty acids with maleic anhydride, and alkali isomerized sunflower methyl esters with maleic anhydride. The products may be used as plasticizers or intermediate therefor, for curing epoxy resins and for the preparation of alkyds.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3559262A GB1032363A (en) | 1962-09-19 | 1962-09-19 | Improvements in or relating to the preparation of di-or tri-basic acids and derivatives thereof |
| DEB73541A DE1272918B (en) | 1962-09-19 | 1963-09-17 | Process for the large-scale production of di- or tribasic cyclohexenecarboxylic acids or their functional derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3559262A GB1032363A (en) | 1962-09-19 | 1962-09-19 | Improvements in or relating to the preparation of di-or tri-basic acids and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1032363A true GB1032363A (en) | 1966-06-08 |
Family
ID=10379443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3559262A Expired GB1032363A (en) | 1962-09-19 | 1962-09-19 | Improvements in or relating to the preparation of di-or tri-basic acids and derivatives thereof |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1272918B (en) |
| GB (1) | GB1032363A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3890259A (en) * | 1973-04-09 | 1975-06-17 | Duco Spa | Acidic oleo-acrylic resins and processes for preparing same |
| US3953479A (en) | 1973-09-04 | 1976-04-27 | Westvaco Corporation | Diglycidyl esters of C21 -cycloaliphatic dicarboxylic acid |
| US3971728A (en) | 1972-03-07 | 1976-07-27 | Ethyl Corporation | Sequestering agent |
| USRE29337E (en) | 1971-10-12 | 1977-08-02 | Westvaco Corporation | Dicarboxylic acid soaps |
| US4196134A (en) | 1977-01-31 | 1980-04-01 | Westvaco Corporation | Vegetable oil adducts |
| US4547224A (en) * | 1984-09-17 | 1985-10-15 | Westvaco Corporation | Emulsifiers for bituminous emulsions |
| US4561901A (en) * | 1984-10-05 | 1985-12-31 | Westvaco Corporation | Emulsifiers for bituminous emulsions |
| US5182326A (en) * | 1991-04-08 | 1993-01-26 | Westvaco Corporation | Rosin and fatty acid based pigment grinding aids for water-based ink formulations |
| US5262525A (en) * | 1991-03-19 | 1993-11-16 | Societe Nationale Elf Aquitaine | Method for the chemical modification of proteins |
| US5336438A (en) * | 1989-05-22 | 1994-08-09 | Westvaco Corporation | Rapid and medium setting high float bituminous emulsions from difficult asphalts |
| US5596032A (en) * | 1994-05-27 | 1997-01-21 | Westvaco Corporation | Slow-setting bituminous emulsions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1046207A (en) * | 1964-07-15 | 1966-10-19 | Bibby & Sons Ltd J | Improvements in or relating to the preparations of dior tri-basic acids and derivatives thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2374381A (en) * | 1945-04-24 | Drying oil products and process of | ||
| US2342113A (en) * | 1942-10-06 | 1944-02-22 | Petrolite Corp | Composition of matter, method of making same, and improved lubricating oil |
| US2444328A (en) * | 1943-12-31 | 1948-06-29 | Petrolite Corp | Composition of matter |
| DE1048272B (en) * | 1953-02-20 | 1959-01-08 | Konink Stearine Kaarsenfabriek | Process for the manufacture of fatty acid adducts |
-
1962
- 1962-09-19 GB GB3559262A patent/GB1032363A/en not_active Expired
-
1963
- 1963-09-17 DE DEB73541A patent/DE1272918B/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE29337E (en) | 1971-10-12 | 1977-08-02 | Westvaco Corporation | Dicarboxylic acid soaps |
| US3971728A (en) | 1972-03-07 | 1976-07-27 | Ethyl Corporation | Sequestering agent |
| DE2416726C3 (en) * | 1973-04-09 | 1980-07-03 | Duco S.P.A., Triest (Italien) | Process for the production of acidic resins by reacting polyunsaturated monocarbon fatty acids with an α, β-unsaturated monocarboxylic acid |
| DE2416726B2 (en) * | 1973-04-09 | 1979-10-18 | Duco S.P.A., Triest (Italien) | Process for the production of acidic resins by reacting polyunsaturated monocarboxylic fatty acids with an α, ß-unsaturated monocarboxylic acid |
| US3890259A (en) * | 1973-04-09 | 1975-06-17 | Duco Spa | Acidic oleo-acrylic resins and processes for preparing same |
| US3953479A (en) | 1973-09-04 | 1976-04-27 | Westvaco Corporation | Diglycidyl esters of C21 -cycloaliphatic dicarboxylic acid |
| US4196134A (en) | 1977-01-31 | 1980-04-01 | Westvaco Corporation | Vegetable oil adducts |
| US4547224A (en) * | 1984-09-17 | 1985-10-15 | Westvaco Corporation | Emulsifiers for bituminous emulsions |
| US4561901A (en) * | 1984-10-05 | 1985-12-31 | Westvaco Corporation | Emulsifiers for bituminous emulsions |
| US5336438A (en) * | 1989-05-22 | 1994-08-09 | Westvaco Corporation | Rapid and medium setting high float bituminous emulsions from difficult asphalts |
| US5262525A (en) * | 1991-03-19 | 1993-11-16 | Societe Nationale Elf Aquitaine | Method for the chemical modification of proteins |
| US5182326A (en) * | 1991-04-08 | 1993-01-26 | Westvaco Corporation | Rosin and fatty acid based pigment grinding aids for water-based ink formulations |
| US5596032A (en) * | 1994-05-27 | 1997-01-21 | Westvaco Corporation | Slow-setting bituminous emulsions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1272918B (en) | 1968-07-18 |
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