GB1049229A - Process for the preparation of aliphatic ªÏ-cyanocarboxylic acids - Google Patents
Process for the preparation of aliphatic ªÏ-cyanocarboxylic acidsInfo
- Publication number
- GB1049229A GB1049229A GB4636664D GB4636664D GB1049229A GB 1049229 A GB1049229 A GB 1049229A GB 4636664 D GB4636664 D GB 4636664D GB 4636664 D GB4636664 D GB 4636664D GB 1049229 A GB1049229 A GB 1049229A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aliphatic
- cyanocarboxylic
- acid
- ammonia
- reaction mixture
- 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
- 125000001931 aliphatic group Chemical group 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 8
- 229910021529 ammonia Inorganic materials 0.000 abstract 4
- 239000011541 reaction mixture Substances 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000001256 steam distillation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aliphatic o -cyanocarboxylic acids are prepared by heating an aliphatic o -dicarboxylic acid together with an amount of ammonia equivalent to one carboxyl group or less either as free ammonia or in the form of a substance that splits off ammonia under the reaction conditions, or the monoammonium salt of an aliphatic o -dicarboxylic acid either alone or in the presence of the free acid at 140 DEG to 220 DEG C. until the evolution of gas ceases and then heating the reaction mixture to 240 DEG to 350 DEG C. until the evolution of gas which has recommenced ceases again. The o -cyanocarboxylic acid can be recovered from the reaction mixture by dissolving said mixture in dilute ammonia, extracting the neutral substances therefrom with a water-immiscible organic solvent, subjecting the residual ammoniacal solution to steam distillation, and extracting the cyanocarboxylic acid from the remaining solution by dilution with water or extraction with a water-immiscible organic solvent. The addition to the initial reaction mixture of 5 to 10% by weight of the o -dicarbonitrile corresponding to the o -cyanocarboxylic acid to be produced and based upon the weight of o -dicarboxylic acid present in the starting material either in the free form or as the mono-ammonium salt, is stated to practically completely eliminate the formation of the o -dicarbonitrile as by-product.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1432363 | 1963-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1049229A true GB1049229A (en) | 1966-11-23 |
Family
ID=4399845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4636664D Expired GB1049229A (en) | 1963-11-22 | 1964-11-13 | Process for the preparation of aliphatic ªÏ-cyanocarboxylic acids |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE654172A (en) |
| CH (1) | CH456562A (en) |
| DE (1) | DE1468114A1 (en) |
| ES (1) | ES305430A1 (en) |
| GB (1) | GB1049229A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014072641A1 (en) | 2012-11-09 | 2014-05-15 | Arkema France | Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4470928A (en) * | 1981-10-15 | 1984-09-11 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing cyanovaleric esters and caprolactam |
-
1964
- 1964-06-04 CH CH1432364A patent/CH456562A/en unknown
- 1964-09-19 DE DE19641468114 patent/DE1468114A1/en active Pending
- 1964-10-09 BE BE654172D patent/BE654172A/xx unknown
- 1964-10-29 ES ES0305430A patent/ES305430A1/en not_active Expired
- 1964-11-13 GB GB4636664D patent/GB1049229A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014072641A1 (en) | 2012-11-09 | 2014-05-15 | Arkema France | Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH456562A (en) | 1968-07-31 |
| ES305430A1 (en) | 1965-03-16 |
| DE1468114A1 (en) | 1968-12-19 |
| BE654172A (en) | 1965-02-01 |
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