CN104513170B - A kind of trans production technology to cyclohexane-carboxylic acid - Google Patents
A kind of trans production technology to cyclohexane-carboxylic acid Download PDFInfo
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- CN104513170B CN104513170B CN201310464998.6A CN201310464998A CN104513170B CN 104513170 B CN104513170 B CN 104513170B CN 201310464998 A CN201310464998 A CN 201310464998A CN 104513170 B CN104513170 B CN 104513170B
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- cyclohexane
- carboxylic acid
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- clear liquid
- trans
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Abstract
The invention provides a kind of trans production technology to cyclohexane-carboxylic acid, by in p-aminobenzoic acid and palladium carbon catalyst input autoclave, open stirring, 80 DEG C are heated to, and hydrogen is passed through into its reactor with hydrogen gas cylinder, the pressure in its reactor is maintained 8.0Mpa, reaction 5 hours is kept on this condition, reaction cools later, filters reaction product, collects clear liquid.By step（1）In the clear liquid input reactor of middle collection, absolute ethyl alcohol is added, stirring is warming up to 50 DEG C, is kept for 1 hour, is then cooled to 20 DEG C, and the sediment of white is filtered out, and collects clear liquid, adds absolute ether, stirs 1 hour at normal temperatures, then filters, is dried to obtain finished product.The beneficial effects of the invention are as follows：This method prepares trans simple to cyclohexane-carboxylic acid step, and that produces is trans to cyclohexane-carboxylic acid high purity 98%, and yield rises to 60% compared with prior art.
Description
Technical field
The present invention relates to drug field, more particularly, to a kind of trans production technology to cyclohexane-carboxylic acid.
Background technology
Trans is a kind of important pharmaceutical intermediate in drug field to cyclohexane-carboxylic acid, but now right on the market
The trans preparation method to cyclohexane-carboxylic acid also there is yield poorly, purity is not high the shortcomings of, the invention provides one kind
Yield reaches the trans to cyclohexane-carboxylic acid preparation method of 60%, purity 98%, this method now on the market also not by
It was found that have to be developed.
The content of the invention
The invention provides a kind of trans production technology to cyclohexane-carboxylic acid.
To realize above-mentioned goal of the invention, the embodiment that the present invention takes is as follows：
A kind of trans production technology to cyclohexane-carboxylic acid, its preparation process are as follows：
（1）Synthesis
By p-aminobenzoic acid and palladium carbon catalyst using mass ratio as 1:In 0.5 ratio input autoclave, open
Stirring, is heated to 80 DEG C, and is passed through hydrogen into its reactor with hydrogen gas cylinder, maintains the pressure in its reactor
8.0Mpa, reaction 5 hours is kept on this condition, reaction cools later, filters reaction product, collects clear liquid.
（2）Purification
By step（1）In the clear liquid input reactor of middle collection, absolute ethyl alcohol is added, stirring is warming up to 50 DEG C, and holding 1 is small
When, 20 DEG C are then cooled to, the sediment of white is filtered out, collects clear liquid, adds absolute ether, is stirred 1 hour at normal temperatures,
Then filter, be dried to obtain finished product.
The beneficial effects of the invention are as follows：This method prepares trans simple to cyclohexane-carboxylic acid step, produces
It is trans to cyclohexane-carboxylic acid high purity 98%, yield rises to 60% compared with prior art.
Embodiment
With reference to embodiments, to according to embodiment provided by the invention, details are as follows：
Embodiment 1
By p-aminobenzoic acid and palladium carbon catalyst using mass ratio as 1:In 0.5 ratio input autoclave, open
Stirring, is heated to 80 DEG C, and is passed through hydrogen into its reactor with hydrogen gas cylinder, maintains the pressure in its reactor
8.0Mpa, reaction 5 hours is kept on this condition, reaction cools later, filters reaction product, collects clear liquid.Add clear liquid into
In reactor, absolute ethyl alcohol is added, stirring is warming up to 50 DEG C, is kept for 1 hour, is then cooled to 20 DEG C, by the sediment of white
Filter out, collect clear liquid, add absolute ether, stir 1 hour at normal temperatures, then filter, be dried to obtain finished product.
One embodiment of the present of invention is described in detail above, but the content is only the preferable implementation of the present invention
Example, it is impossible to be considered as the practical range for limiting the present invention.All equivalent changes made according to the present patent application scope and improvement
Deng, all should still belong to the present invention patent covering scope within.
Claims (1)
1. a kind of trans production technology to cyclohexane-carboxylic acid, its preparation process is as follows：
（1）Synthesis
By p-aminobenzoic acid and palladium carbon catalyst using mass ratio as 1:In 0.5 ratio input autoclave, stirring is opened,
80 DEG C are heated to, and hydrogen is passed through into its reactor with hydrogen gas cylinder, the pressure in its reactor is maintained 8.0Mpa,
Reaction 5 hours is kept under the conditions of this, reaction cools later, filters reaction product, collects clear liquid；
（2）Purification
By step（1）In the clear liquid input reactor of middle collection, absolute ethyl alcohol is added, stirring is warming up to 50 DEG C, is kept for 1 hour,
Then 20 DEG C are cooled to, the sediment of white is filtered out, collects clear liquid, adds absolute ether, at normal temperatures stirring 1 hour, so
After filter, be dried to obtain finished product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310464998.6A CN104513170B (en) | 2013-09-29 | 2013-09-29 | A kind of trans production technology to cyclohexane-carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201310464998.6A CN104513170B (en) | 2013-09-29 | 2013-09-29 | A kind of trans production technology to cyclohexane-carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
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| CN104513170A CN104513170A (en) | 2015-04-15 |
| CN104513170B true CN104513170B (en) | 2018-02-27 |
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| CN201310464998.6A Active CN104513170B (en) | 2013-09-29 | 2013-09-29 | A kind of trans production technology to cyclohexane-carboxylic acid |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108602758B (en) * | 2016-02-05 | 2021-01-26 | 斯福瑞股份公司 | Process for preparing trans-4-amino-1-cyclohexanecarboxylic acids and derivatives thereof |
| EP3255033A1 (en) * | 2016-06-10 | 2017-12-13 | Basf Se | Discrimination of cis- and trans-1,3-diaminocyclohexanes |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2888484A (en) * | 1957-09-09 | 1959-05-26 | Hercules Powder Co Ltd | Production of hexahydroterephthalic acid |
| US5965565A (en) * | 1996-12-12 | 1999-10-12 | Merck & Co., Inc. | Piperidines promote release of growth hormone |
| CN1453265A (en) * | 2002-04-26 | 2003-11-05 | 中国人民解放军军事医学科学院毒物药物研究所 | Aromatic amino acid derivative and its prepn process and medicinal use |
| CN1517335A (en) * | 2003-01-17 | 2004-08-04 | 中国人民解放军军事医学科学院毒物药 | Improved preparation method of Nagelinei |
-
2013
- 2013-09-29 CN CN201310464998.6A patent/CN104513170B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2888484A (en) * | 1957-09-09 | 1959-05-26 | Hercules Powder Co Ltd | Production of hexahydroterephthalic acid |
| US5965565A (en) * | 1996-12-12 | 1999-10-12 | Merck & Co., Inc. | Piperidines promote release of growth hormone |
| CN1453265A (en) * | 2002-04-26 | 2003-11-05 | 中国人民解放军军事医学科学院毒物药物研究所 | Aromatic amino acid derivative and its prepn process and medicinal use |
| CN1517335A (en) * | 2003-01-17 | 2004-08-04 | 中国人民解放军军事医学科学院毒物药 | Improved preparation method of Nagelinei |
Non-Patent Citations (3)
| Title |
|---|
| Highly selective preparation of trans-4-aminocyclohexanecarboxylic acid from cis-isomer over Raney nickel catalyst;Gobolos,Sandor 等;《Chemical Industries》;20071231;第115卷;第45-53页 * |
| Synthesis of rigid analogs of (D,L)-arginine methyl ester with antiarrhythmic activity;Banfi,A. 等;《Synthetic Communications》;19891231;第19卷(第9-10期);第1788页倒数第1-3行和1790页第1-6行和第1789页图解1以及第1792页第4段 * |
| 负载型Rh催化剂上对氨基苯甲酸加氢反应研究;邵国刚 等;《河北工业大学学报》;20080831;第37卷(第4期);第7-13页 * |
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| CN104513170A (en) | 2015-04-15 |
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Effective date of registration: 20200731 Address after: 300270 No. 1266 Triumph Street, Dagang Street, Binhai New District, Tianjin Patentee after: RIONLON BOHUA (TIANJIN) MEDICINE CHEMICAL Co.,Ltd. Address before: 300000, 1266, Triumph Street, petrochemical industrial park, Binhai New Area, Tianjin Patentee before: TIANJIN RUIAN MEDICAL TECHNOLOGY DEVELOPMENT Co.,Ltd. |