CN101092362A - Method for preparing 3,5 - di-tert-butyl - hydroxy phenyl methyl propionate - Google Patents
Method for preparing 3,5 - di-tert-butyl - hydroxy phenyl methyl propionate Download PDFInfo
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- CN101092362A CN101092362A CN 200710043551 CN200710043551A CN101092362A CN 101092362 A CN101092362 A CN 101092362A CN 200710043551 CN200710043551 CN 200710043551 CN 200710043551 A CN200710043551 A CN 200710043551A CN 101092362 A CN101092362 A CN 101092362A
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- butyl
- tert
- hydroxy phenyl
- methyl propionate
- phenyl methyl
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Abstract
This invention relates to a method for preparing methyl 3,5-di(tert-butyl)-4-hydroxylphenyl propionate. The method comprises: mixing 26 phenol and catalyst at a mol. ratio of 1:(0.01-0.03), adding methyl propionate so that the mol. ratio of 26 phenol to methyl propionate is 1:(0.85-1.20), controlling the reaction temperature at 100-140 deg.C, performing heat preservation reaction for 3-8 h, adding neutralizing acid catalyst at a 26 phenol/neutralizing acid mol. ratio of 1:(0.01-0.03), filtering, vacuum-evaporating to remove light components and obtain methyl 3,5-di(tert-butyl)-4-hydroxylphenyl propionate addition solution, and sending the addition solution to a light component removal and refinery column system to obtain 3,5-di(tert-butyl)-4-hydroxylphenyl propionate (purity greater than or equal to 99.50%). The method has such advantages as high product quality, low cost and high yield.
Description
Technical field
The present invention relates to a kind of oxidation inhibitor intermediate manufacturing technology field, relate in particular to a kind of 3, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate.
Background technology
26 phenol and methyl acrylate carry out addition reaction under the basic catalyst effect, generate a kind ofly 3, and the 5-di-tert-butyl-hydroxy phenyl methyl propionate is called for short 35 addition liquid.35 addition liquid are 3, the crude product of 5-di-tert-butyl-hydroxy phenyl methyl propionate, it can the method by crystallization or rectifying be purified, obtain a kind of 3, the product of 5-di-tert-butyl-hydroxy phenyl methyl propionate.
At present, 3, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate (being called for short 35 methyl esters) uses lower alcohols mostly, carry out the method for decrease temperature crystalline as solvent as methyl alcohol, ethanol etc., because under the condition of lesser temps, 35 methyl esters also have certain solubleness in alcohol, so low with crystalline method of purification yield, part 3, the 5-di-tert-butyl-hydroxy phenyl methyl propionate enters mother liquor and can not reclaim, so material loss is big, the production cost height.
Summary of the invention
Purpose of the present invention is exactly to provide 3 of a kind of low cost, high yield, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate for the defective that overcomes above-mentioned prior art existence.
Purpose of the present invention can be achieved through the following technical solutions:
A kind of 3, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate, it is characterized in that, this method is by 1: 0.01～0.05 mol ratio thorough mixing with 26 phenol and catalyzer, add methyl acrylate, make 26 phenol: the mol ratio of methyl acrylate is 1: 0.85～1.25, and control reaction temperature is 100 ℃～140 ℃, carry out the addition insulation reaction, insulation reaction 2～8 hours, by 26 phenol: the neutralizing acid mol ratio is 1: 0.01～0.03 to add sour catalyst neutralisation, promptly get 3 after the filtration, the addition liquid of 5-di-tert-butyl-hydroxy phenyl methyl propionate is after addition liquid removes light constituent, the tower still take off light liquid through refining obtain a kind of highly purified 3, the 5-di-tert-butyl-hydroxy phenyl methyl propionate.
Described catalyzer is a kind of basic catalyst.
Described 26 phenol, catalyzer, methyl acrylate, antacid mol ratio ratio are: 1: 0.01～0.03: 0.90～1.10: 0.01～0.02.
Described temperature of reaction is 110 ℃～130 ℃.
The described insulation reaction time is 3～6 hours.
The acid of described catalyst neutralisation comprises formic acid, acetate etc., and the reactant after the neutralization filters removes salt.
Described addition liquid adopts rectificating method to purify, and described rectifying is two tower continuous rectifications under high vacuum condition.
Compared with prior art, the present invention is by changing the optimization of proportioning raw materials, and temperature, the pressure of rectifying carried out strictness control, make produced 3, the 5-di-tert-butyl-hydroxy phenyl methyl propionate reduces 6～10% to the consumption rate crystallization process of 26 phenol, has low cost, high yield and high-quality characteristics.
Embodiment
The invention will be further described below in conjunction with specific embodiment.
Embodiment 1
26 phenol and the alkaline liquid catalyzer of specified amount are pressed phenol: the proportioning of the mol ratio of catalyzer=1: 0.01 adds, then according to 26 phenol: catalyzer: the ratio of methyl acrylate=1: 0.01: 0.90 is added dropwise to methyl acrylate, and control reaction temperature is carried out addition reaction at 125 ± 5 ℃.After dropwising, insulation reaction 4 hours, add the acetic acid catalyst neutralisation then, the mol ratio of 26 phenol and acetic acid is 1: 0.01, filters and removes salt, obtains 35 addition liquid, analyze 3, the content of 5-di-tert-butyl-hydroxy phenyl methyl propionate is 92.02%, gets 3 through high vacuum rectification, and the content of 5-di-tert-butyl-hydroxy phenyl methyl propionate is 99.65%.
Described addition reaction equation is:
Embodiment 2
With 26 phenol of specified amount and liquid basified catalyzer by 26 phenol: the proportioning of catalyst molar ratio=1: 0.02 adds, then according to 26 phenol: catalyzer: the ratio dropwise addition of acrylic acid methyl esters of methyl acrylate mol ratio=1: 0.02: 0.95, control reaction temperature is carried out addition reaction at 120 ± 5 ℃.After dropwising, insulation reaction 5 hours, add the acetic acid catalyst neutralisation then, the mol ratio of 26 phenol and acetic acid is 1: 0.02, filters and removes salt, obtains 35 addition liquid, analyze 3, the content of 5-di-tert-butyl-hydroxy phenyl methyl propionate is 93.01%, gets 3 through high vacuum rectification, and the content of 5-di-tert-butyl-hydroxy phenyl methyl propionate is 99.53%.
Described addition reaction equation is:
Embodiment 3
With 26 phenol of specified amount and liquid basified catalyzer by 26 phenol: the proportioning of catalyst molar ratio=1: 0.03 adds, then according to 26 phenol: catalyzer: the ratio dropwise addition of acrylic acid methyl esters of the mol ratio of methyl acrylate=1: 0.03: 1.05, control reaction temperature is carried out addition reaction at 115 ± 5 ℃.After dropwising, insulation reaction 6 hours, add the acetic acid catalyst neutralisation then, the mol ratio of 26 phenol and acetic acid is 1: 0.03, filters and removes salt, obtains 35 addition liquid, analyze 3, the content of 5-di-tert-butyl-hydroxy phenyl methyl propionate is 95.03%, gets 3 through high vacuum rectification, and the content of 5-di-tert-butyl-hydroxy phenyl methyl propionate is 99.61%.
Described addition reaction equation is:
Claims (7)
1, a kind of 3, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate, it is characterized in that, this method is by 1: 0.01～0.05 mol ratio thorough mixing with 26 phenol and catalyzer, add methyl acrylate, make 26 phenol: the mol ratio of methyl acrylate is 1: 0.85～1.20, and control reaction temperature is 100 ℃～140 ℃, carry out the addition insulation reaction, insulation reaction 2～8 hours, by 26 phenol: the neutralizing acid mol ratio is 1: 0.01～0.03 to add sour catalyst neutralisation, filters, and promptly gets 3 after extracting light constituent, the addition liquid of 5-di-tert-butyl-hydroxy phenyl methyl propionate, after addition liquid removes light constituent, the tower still take off light liquid obtain after refining a kind of 3, the 5-di-tert-butyl-hydroxy phenyl methyl propionate.
2, according to claim 1 a kind of 3, the preparation method of 5-di-t-butyl～4-hydroxy phenyl methyl propionate is characterized in that described catalyzer is a kind of basic catalyst.
3, according to claim 1 a kind of 3, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate, it is characterized in that described 26 phenol, catalyzer, methyl acrylate, antacid mol ratio ratio are: 1: 0.01～0.03: 0.90～1.10: 0.01～0.02.
4, according to claim 1 a kind of 3, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate is characterized in that, described temperature of reaction is 110 ℃～130 ℃.
5, according to claim 1 a kind of 3, the preparation method of 5-di-t-butyl-4 monohydroxy phenylpropionic acid methyl esters is characterized in that the described insulation reaction time is 3～6 hours.
6, according to claim 1 a kind of 3, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate is characterized in that, the acid of described catalyst neutralisation comprises formic acid, acetate etc., and the reactant after the neutralization filters removes salt.
7, according to claim 1 a kind of 3, the preparation method of 5-di-tert-butyl-hydroxy phenyl methyl propionate is characterized in that, described addition liquid adopts rectificating method to purify, and described rectifying is two tower continuous rectifications under high vacuum condition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN 200710043551 CN101092362A (en) | 2007-07-06 | 2007-07-06 | Method for preparing 3,5 - di-tert-butyl - hydroxy phenyl methyl propionate |
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| CN 200710043551 CN101092362A (en) | 2007-07-06 | 2007-07-06 | Method for preparing 3,5 - di-tert-butyl - hydroxy phenyl methyl propionate |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060705A (en) * | 2010-11-24 | 2011-05-18 | 上海华谊（集团）公司 | Synthesis method of beta-(3,5-tertbutyl-4-hydroxy)methyl propionate |
| CN101475806B (en) * | 2009-01-24 | 2012-01-18 | 南亚塑胶工业股份有限公司 | Preparation of hindered phenol type anti-oxidant |
| CN104910008A (en) * | 2015-05-25 | 2015-09-16 | 新乡市瑞丰新材料股份有限公司 | Purification method of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl propionate |
| CN104910007A (en) * | 2015-04-24 | 2015-09-16 | 新乡市瑞丰新材料股份有限公司 | 3-(3, 5-ditertiary butyl-4-hydroxy phenyl) methyl propionate synthesis process |
-
2007
- 2007-07-06 CN CN 200710043551 patent/CN101092362A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101475806B (en) * | 2009-01-24 | 2012-01-18 | 南亚塑胶工业股份有限公司 | Preparation of hindered phenol type anti-oxidant |
| CN102060705A (en) * | 2010-11-24 | 2011-05-18 | 上海华谊（集团）公司 | Synthesis method of beta-(3,5-tertbutyl-4-hydroxy)methyl propionate |
| CN104910007A (en) * | 2015-04-24 | 2015-09-16 | 新乡市瑞丰新材料股份有限公司 | 3-(3, 5-ditertiary butyl-4-hydroxy phenyl) methyl propionate synthesis process |
| CN104910008A (en) * | 2015-05-25 | 2015-09-16 | 新乡市瑞丰新材料股份有限公司 | Purification method of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl propionate |
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Open date: 20071226 |