GB1179673A - A Process for the Production of Sebacic Acid - Google Patents
A Process for the Production of Sebacic AcidInfo
- Publication number
- GB1179673A GB1179673A GB882768A GB882768A GB1179673A GB 1179673 A GB1179673 A GB 1179673A GB 882768 A GB882768 A GB 882768A GB 882768 A GB882768 A GB 882768A GB 1179673 A GB1179673 A GB 1179673A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sebacic acid
- adipate
- methanol
- acid
- monomethyl adipate
- 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
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 title abstract 12
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 12
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 abstract 6
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- -1 alkali metal monomethyl adipate Chemical class 0.000 abstract 3
- 229940014772 dimethyl sebacate Drugs 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 abstract 2
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- XWMAGYLNUHTFKC-UHFFFAOYSA-M sodium;6-methoxy-6-oxohexanoate Chemical compound [Na+].COC(=O)CCCCC([O-])=O XWMAGYLNUHTFKC-UHFFFAOYSA-M 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,179,673. Sebacic acid. VSESOJUZNY NAUCHNO-ISSLEDOVATELSKY I PROEKTNY INSTITUT MONOMEROV. 23 Feb., 1968, No. 8827/68. Heading C2C. [Also in Division C7] A process for the production of sebacic acid comprises producing dimethyl sebacate by the electrolytic condensation of monomethyl adipate in methanol medium in the presence of an alkali metal monomethyl adipate, e.g. sodium monomethyl adipate, stripping off methanol from the mixture of electrolytic condensation products thus obtained, allowing the mixture to separate into an ester layer containing dimethyl sebacate and a layer containing the alkali metal monomethyl adipate, converting the dimethyl sebacate contained in the ester layer into sebacic acid by a two-stage hydrolysis step comprising hydrolysis using water at a temperature above 100‹ C. under superatmospheric pressure, and the amount of water added being not less than five times the weight of ester present, and hydrolysis using an aqueous solution of a mineral acid, e.g. nitric acid, and recovering the sebacic acid thus formed, e.g. by recrystallization from water. The sebacic acid formed may be purified with activated carbon. The starting material monomethyl adipate may be produced from adipic acid by esterification with methanol in the presence of dimethyl adipate. The methanol, alkali metal monoethyl adipate and the mineral acid used may be recycled.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB882768A GB1179673A (en) | 1968-02-23 | 1968-02-23 | A Process for the Production of Sebacic Acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB882768A GB1179673A (en) | 1968-02-23 | 1968-02-23 | A Process for the Production of Sebacic Acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1179673A true GB1179673A (en) | 1970-01-28 |
Family
ID=9859985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB882768A Expired GB1179673A (en) | 1968-02-23 | 1968-02-23 | A Process for the Production of Sebacic Acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1179673A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113582844A (en) * | 2021-08-12 | 2021-11-02 | 山东元利科技有限公司 | Method for removing monoester compound from sebacate compound |
-
1968
- 1968-02-23 GB GB882768A patent/GB1179673A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113582844A (en) * | 2021-08-12 | 2021-11-02 | 山东元利科技有限公司 | Method for removing monoester compound from sebacate compound |
| CN113582844B (en) * | 2021-08-12 | 2023-05-26 | 山东元利科技有限公司 | Method for removing monoester compound from sebacate compound |
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