CN101717333B - Preparation method of (-)-di(p-toluoyl)tartaric acid - Google Patents
Preparation method of (-)-di(p-toluoyl)tartaric acid Download PDFInfo
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- CN101717333B CN101717333B CN2009102127167A CN200910212716A CN101717333B CN 101717333 B CN101717333 B CN 101717333B CN 2009102127167 A CN2009102127167 A CN 2009102127167A CN 200910212716 A CN200910212716 A CN 200910212716A CN 101717333 B CN101717333 B CN 101717333B
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- paratolunitrile
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Abstract
The invention discloses a preparation method of (-)-di(p-toluoyl)tartaric acid. The preparation method comprises the following steps of: adding certain quantity of para-toluylicacid, solvent and catalyst into a flask which is provided with a reflux condenser, simultaneously dropwise adding thionyl chloride; and then adding certain quantity of tartaric acid after heating for reflux for a while; then continuing to heat for reflux for a while; after reaction is finished, cooling to room temperature; adjusting pH value to be neutral by using an alkali solution; after finishing pH adjusting, heating for reflux for a while; after reaction, cooling to below 20 DEG C; filtrating to obtain a crystal; washing twice with a reactive solvent; and baking to obtain the product. The process has the characteristics of simple process, high efficiency, direct product obtaining without treating a semi-finished product, and adaptability to actual production.
Description
Technical field
The present invention relates to the preparation method of the acid resolving agent of a kind of optics, be meant (-)-two couples of tartaric preparing methods of toluyl especially.
Background technology
In scientific research and actual production, the acid resolving agent of optics commonly used is very limited, and it is several only to be confined to only a few such as tartrate, is difficult to satisfy the research and production needs, and the acid resolving agent of the optics of developing new product variety is very urgent.(-)-two pair toluyl tartrate belongs to a kind of of tartaric acids resolving agent, and compound method has relevant report at present, but production stage is more loaded down with trivial details, and production link is more, influences production efficiency.
Summary of the invention
The purpose of this invention is to provide the tartaric preparation method of (-)-two pair toluyl that a kind of technology is simple, adapt to needs of production.
For realizing above-mentioned purpose, the present invention adopts following technical scheme to realize:
(-)-two pair toluyl is tartaric preparation method may further comprise the steps:
The preparation of a, Butyltriphenylphosphonium chloride:
In the flask of reflux exchanger is housed, add a certain amount of paratolunitrile, solvent and catalyzer, the while dripping thionyl chloride, after waiting to dropwise, reflux 2～6 hours;
B, the tartaric preparation of (-)-two pair toluyl:
In the reaction solution that above-mentioned reaction obtains, add a certain amount of tartrate, reflux 1～4 hour, question response is reduced to room temperature after finishing; Be adjusted to neutrality with liquid caustic soda, after pH regulator finishes, reflux 1～3 hour; Reaction finishes, and blowing is cooled to below 20 ℃ while hot; Leach crystallization, with reaction solvent washing two oven dry, obtain white crystal again; Said catalyzer is: N, dinethylformamide.Described solvent is: toluene, benzene;
Said solvent load is 1～4 times of paratolunitrile weight;
Catalyst levels is 0.02～0.1 times of paratolunitrile weight;
The sulfur oxychloride consumption is 1.2～2.5 times of paratolunitrile molar weight;
The tartrate consumption is 0.4～0.6 times of paratolunitrile molar weight;
Described liquid caustic soda concentration is: 20～30%.
The invention has the advantages that: technology is simple, efficient, directly obtains product, need not handle intermediates.Be suitable for actual production.
Embodiment
Below in conjunction with embodiment, the present invention is done further description.
Embodiment 1
The preparation of a, Butyltriphenylphosphonium chloride:
In the 500ml flask of reflux exchanger is housed, add 100g paratolunitrile, 200g toluene and 2gDMF, drip the 120g sulfur oxychloride simultaneously, after waiting to dropwise, reflux 4 hours.
B, the tartaric preparation of (-)-two pair toluyl:
In above-mentioned reaction solution, add 65g tartrate, reflux 2 hours.Question response is reduced to room temperature after finishing, and is adjusted to neutrality with liquid caustic soda.After pH regulator finishes, reflux 3 hours, reaction finishes, and blowing is cooled to below 20 ℃ while hot, leaches crystallization, uses the reaction solvent washed twice again, and oven dry obtains white crystal 241g, yield 85%.
Embodiment 2
The preparation of a, Butyltriphenylphosphonium chloride:
In the 500ml flask of reflux exchanger is housed, add 100g paratolunitrile, 300g toluene and 4gDMF, drip the 140g sulfur oxychloride simultaneously, after waiting to dropwise, reflux 6 hours.
B, the tartaric preparation of (-)-two pair toluyl:
In above-mentioned reaction solution, add 70g tartrate, reflux 4 hours.Question response is reduced to room temperature after finishing, and is adjusted to neutrality with liquid caustic soda.After pH regulator finishes, reflux 1 hour, reaction finishes, and blowing is cooled to below 20 ℃ while hot, leaches crystallization, uses the reaction solvent washed twice again, and oven dry obtains white crystal 250g, yield 87%.
Claims (4)
1. the tartaric preparation method of (-)-two pair toluyl is characterized in that, may further comprise the steps:
The preparation of a, Butyltriphenylphosphonium chloride:
In the flask of reflux exchanger is housed, add a certain amount of paratolunitrile, solvent and catalyzer, the while dripping thionyl chloride, after waiting to dropwise, reflux 2～6 hours;
B, the tartaric preparation of (-)-two pair toluyl:
In the reaction solution that above-mentioned reaction obtains, add a certain amount of tartrate, reflux 1～4 hour, question response is reduced to room temperature after finishing; Be adjusted to neutrality with liquid caustic soda, after pH regulator finishes, reflux 1～3 hour, reaction finishes; Blowing is cooled to below 20 ℃ while hot, leaches crystallization; Use the reaction solvent washed twice again, oven dry obtains white crystal;
Said catalyzer is: N, dinethylformamide.
2. the tartaric preparation method of (-) according to claim 1-two pair toluyl is characterized in that described solvent is: toluene, benzene.
3. the tartaric preparation method of (-) according to claim 1-two pair toluyl; It is characterized in that; Said solvent load is 1～4 times of paratolunitrile weight; Catalyst levels is 0.02～0.1 times of paratolunitrile weight, and the sulfur oxychloride consumption is 1.2～2.5 times of paratolunitrile molar weight, and the tartrate consumption is 0.4～0.6 times of paratolunitrile molar weight.
4. the tartaric preparation method of (-) according to claim 1-two pair toluyl is characterized in that described liquid caustic soda concentration is: 20～30%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102127167A CN101717333B (en) | 2009-10-30 | 2009-10-30 | Preparation method of (-)-di(p-toluoyl)tartaric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102127167A CN101717333B (en) | 2009-10-30 | 2009-10-30 | Preparation method of (-)-di(p-toluoyl)tartaric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101717333A CN101717333A (en) | 2010-06-02 |
| CN101717333B true CN101717333B (en) | 2012-08-22 |
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| CN2009102127167A Expired - Fee Related CN101717333B (en) | 2009-10-30 | 2009-10-30 | Preparation method of (-)-di(p-toluoyl)tartaric acid |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945259A (en) * | 2015-06-02 | 2015-09-30 | 安徽兴东化工有限公司 | Synthetic method of di(p-toluoyl)tartaric acid |
| CN105330531B (en) * | 2015-12-14 | 2018-03-16 | 山东凯盛新材料股份有限公司 | To the continuous production processes of methyl benzoyl chloride |
| CN105330532B (en) * | 2015-12-14 | 2018-07-20 | 山东凯盛新材料股份有限公司 | To the preparation method of methyl benzoyl chloride |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0600714A1 (en) * | 1992-11-30 | 1994-06-08 | Toray Industries, Inc. | Process for producing O,O'-diacyltartaric anhydride and process for producing O,O'-diacyltartaric acid |
-
2009
- 2009-10-30 CN CN2009102127167A patent/CN101717333B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0600714A1 (en) * | 1992-11-30 | 1994-06-08 | Toray Industries, Inc. | Process for producing O,O'-diacyltartaric anhydride and process for producing O,O'-diacyltartaric acid |
Non-Patent Citations (3)
| Title |
|---|
| 曾善麟 等.左或右旋二对甲苯甲酰酒石酸合成工艺的改进.《化学试剂》.2002,第24卷(第5期),309、311. * |
| 贺蕴普 等.拆分剂(+ )-2, 3-二对甲苯甲酰氧丁二酸的合成.《化学试剂》.1999,第21卷(第2期),106-107. * |
| 贺蕴普等.拆分剂(+)-2 3-二对甲苯甲酰氧丁二酸的合成.《化学试剂》.1999 |
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