GB1005641A - Dihalocarbene addition products of unsaturated carboxylic acids - Google Patents
Dihalocarbene addition products of unsaturated carboxylic acidsInfo
- Publication number
- GB1005641A GB1005641A GB4308/62A GB430862A GB1005641A GB 1005641 A GB1005641 A GB 1005641A GB 4308/62 A GB4308/62 A GB 4308/62A GB 430862 A GB430862 A GB 430862A GB 1005641 A GB1005641 A GB 1005641A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- dihalocarbene
- carboxylic acids
- unsaturated carboxylic
- addition products
- 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
- 150000001735 carboxylic acids Chemical class 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 abstract 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 abstract 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 abstract 1
- ZDQUDOWRBBJPQM-UHFFFAOYSA-N 9,10-bis(chloromethylidene)-2-methyloctadecanoic acid Chemical compound CC(C(=O)O)CCCCCCC(C(CCCCCCCC)=CCl)=CCl ZDQUDOWRBBJPQM-UHFFFAOYSA-N 0.000 abstract 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 abstract 1
- QYDYPVFESGNLHU-ZHACJKMWSA-N Methyl (9E)-9-octadecenoate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OC QYDYPVFESGNLHU-ZHACJKMWSA-N 0.000 abstract 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical class Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 abstract 1
- 125000005908 glyceryl ester group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 abstract 1
- 229940073769 methyl oleate Drugs 0.000 abstract 1
- 229960005235 piperonyl butoxide Drugs 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000003549 soybean oil Substances 0.000 abstract 1
- 235000012424 soybean oil Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Carboxylic acid derivatives containing dihalocyclopropane rings are prepared by reacting a dihalocarbene with an olefinically unsaturated aliphatic carboxylic acid having its carboxyl group protected with a non-protonic radical, e.g. as a salt or an ester, e.g. an alkyl or glyceryl ester. Temperatures between -90 and + 20 DEG C. may be used. The products may be used as plasticizers and may be converted to the free acid by hydrolysis or to other esters by alcoholysis. In examples, dichlorocarbene is produced from hexachloroacetone and sodium methoxide or from chloroform and potassium t.-butoxide and reacted with methyl oleate (to give methyl 9,10-dichloromethylene octadecanoic acid), methyl linoleate, methyl linoleneate, linseed oil, soybean oil and methyl elaidate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4308/62A GB1005641A (en) | 1962-02-05 | 1962-02-05 | Dihalocarbene addition products of unsaturated carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4308/62A GB1005641A (en) | 1962-02-05 | 1962-02-05 | Dihalocarbene addition products of unsaturated carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1005641A true GB1005641A (en) | 1965-09-22 |
Family
ID=9774722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4308/62A Expired GB1005641A (en) | 1962-02-05 | 1962-02-05 | Dihalocarbene addition products of unsaturated carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1005641A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012430A (en) * | 1972-05-16 | 1977-03-15 | Shell Oil Company | Process for the preparation of cyclopropane derivatives |
| WO2000001658A1 (en) * | 1998-07-02 | 2000-01-13 | Cargill, Incorporated | Process for modifying unsaturated triacylglycerol oils; resulting products and uses thereof |
| US6051539A (en) * | 1998-07-02 | 2000-04-18 | Cargill, Inc. | Process for modifying unsaturated triacylglycerol oils resulting products and uses thereof |
-
1962
- 1962-02-05 GB GB4308/62A patent/GB1005641A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012430A (en) * | 1972-05-16 | 1977-03-15 | Shell Oil Company | Process for the preparation of cyclopropane derivatives |
| WO2000001658A1 (en) * | 1998-07-02 | 2000-01-13 | Cargill, Incorporated | Process for modifying unsaturated triacylglycerol oils; resulting products and uses thereof |
| US6051539A (en) * | 1998-07-02 | 2000-04-18 | Cargill, Inc. | Process for modifying unsaturated triacylglycerol oils resulting products and uses thereof |
| US6291409B1 (en) | 1998-07-02 | 2001-09-18 | Cargill, Inc. | Process for modifying unsaturated triacylglycerol oils; Resulting products and uses thereof |
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