CN107311868A - A kind of method for preparing p-tert-butyl benzoic acid methyl esters - Google Patents
A kind of method for preparing p-tert-butyl benzoic acid methyl esters Download PDFInfo
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- CN107311868A CN107311868A CN201710486625.7A CN201710486625A CN107311868A CN 107311868 A CN107311868 A CN 107311868A CN 201710486625 A CN201710486625 A CN 201710486625A CN 107311868 A CN107311868 A CN 107311868A
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- butyl benzoic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
The present invention relates to a kind of method for preparing p-tert-butyl benzoic acid methyl esters, methods described is using methanol, p-tert-butyl benzoic acid as raw material, to carry out esterification in the presence of catalyst is sulfonate resin, separation produces p-tert-butyl benzoic acid methyl esters.Wherein described azochlorosulfonate acid resin catalyst environmental protection, easily separate, can recycle with product.This method has that catalyst stability is good, reactivity is high, it is environment-friendly, can be easily separated without equipment corrosion, product, many advantages, such as catalyst can be recycled.
Description
Technical field
The present invention relates to a kind of method for preparing p-tert-butyl benzoic acid methyl esters, and in particular to one kind is in green acid catalyst
In the presence of prepare the method for p-tert-butyl benzoic acid methyl esters.
Background technology
P-tert-butyl benzoic acid methyl esters is widely used in chemical conjunction as important organic synthesis intermediate and medicine intermediate
Into, the industry such as cosmetics, medicine, essence and flavoring agent.The annual requirement in market is very big, therefore, studies p-tert-butyl benzoic acid first
The synthesis of ester has important value.
P-tert-butyl benzoic acid process for production of methyl urging in acid catalyst with methanol mainly by p-tert-butyl benzoic acid
The lower generation esterification of change effect is made.The synthetic method of traditional p-tert-butyl benzoic acid methyl esters is as urging using the concentrated sulfuric acid
Agent, direct catalytic esterification, although yield is high, but the easy dehydration of organic matter, carbonization, and the reaction time is long, separation post processing
Deng difficulty.And this method environmental pollution influence is larger, and its wastewater discharge is big, serious to equipment corrosion.And it is another
Method is typically to use anhydrous AlCl3、FeCl3, titanium sulfate be used as catalyst synthesis p-tert-butyl benzoic acid methyl esters, this method
Need to use esterification technology controlling and process back flow reaction, although high conversion rate, simple to operate, but the catalyst used in the method
Facile hydrolysis, reaction need to be carried out under strict anhydrous condition, and need persistently to divide water in course of reaction.Therefore, seek active height, urge
It is to need solution at present that agent stability is good, the segregative green acidic catalyst catalysis of product prepares p-tert-butyl benzoic acid methyl esters
Certainly the problem of.
The content of the invention
It is sulfonic acid tree in catalyst it is an object of the invention to provide one kind using methanol, p-tert-butyl benzoic acid as raw material
The new method that esterification prepares p-tert-butyl benzoic acid methyl esters is carried out in the presence of fat.This method has catalyst stability
It is good, reactivity is high, environment-friendly, can be easily separated without equipment corrosion, product, the advantages of catalyst can be recycled.
Methods described is specially：Methanol, p-tert-butyl benzoic acid, sulfonate resin are mixed, heating carries out esterification,
Centrifuge, it is p-tert-butyl benzoic acid methyl esters to take upper strata product revolving separation；
Wherein, lower floor is azochlorosulfonate acid resin catalyst after the centrifugation.
The azochlorosulfonate acid resin catalyst is containing SO3It is the resin catalyst of H functional groups, preferably polystyrene sulfonic acid resin, complete
One or both of perfluorosulfonic acid resin.
Wherein, resinae catalyst containing sulfonic acid functional group is more easily separated.
The azochlorosulfonate acid resin catalyst is solid, and after the completion of reaction, product is easily isolated with catalyst, therefore the sulphur
Acid resin catalyst can be repeatedly circulated.
Wherein the present invention is limited without strict anhydrous condition, therefore methanol can participate in anti-with the state of any concentration
Should, preferably pure methanol.
Present invention further propose that, methods described is specifically prepared using step：
1) methanol, p-tert-butyl benzoic acid, sulfonate resin are mixed, temperature be 50~200 DEG C, pressure be 0.1~
Under conditions of 4Mpa, 0.1~15h of stirring is reacted, and obtains reaction solution；
2) by step 1) obtained by reaction solution be centrifuged, take upper strata crude product to carry out revolving processing, produce to uncle
Butylbenzoic acid methyl esters.
The upper strata crude product revolving first removes methanol, water, and the revolving that then heats up again obtains target product to tert-butyl benzene
Methyl formate, wherein unreacted p-tert-butyl benzoic acid and Methanol Recovery are utilized, lower catalyst agent is recycled.
The mol ratio of the p-tert-butyl benzoic acid and methanol is 1:1~1:30, preferably:1:8~1:10.
The weight of the catalyst is the 1%~20% of the raw material weight, preferably 10%.
The pressure is 0.1~4Mpa；
The temperature is 50~200 DEG C；
The time of the reaction is 0.1~15h.
Present invention further propose that preferred scheme be, a kind of method for preparing p-tert-butyl benzoic acid methyl esters, the side
Method comprises the following steps：
1) it is 1 by mol ratio:8~1:10 p-tert-butyl benzoic acid, the raw material of methanol are added in reactor, are added and are accounted for
Raw material weight percentage is 10% polystyrene sulfonic acid resin or perfluorinated sulfonic resin catalyst, is 100~120 in temperature
DEG C, pressure be 1~1.6Mpa under conditions of, stirring 2~8h reacted, obtain reaction solution；
2) by step 1) obtained by reaction solution be centrifuged, take upper strata crude product to carry out revolving processing, produce to uncle
Butylbenzoic acid methyl esters；
Lower floor is catalyst after the centrifugation, and the catalyst is recycled.
Another object of the present invention is to propose a kind of p-tert-butyl benzoic acid methyl esters prepared using any of the above-described method.
A kind of method for preparing p-tert-butyl benzoic acid methyl esters of the present invention, including at least following advantage：
1) the azochlorosulfonate acid resin catalyst stability that is used is good, environmental protection；
2) catalytic reaction activity is high, and reaction speed is fast, and reaction condition is relatively mild, and reaction requires low, it is easy to industrial metaplasia
Production.
3) present invention does not result in the corrosion and environmental pollution of consersion unit, and production process is environment-friendly, and reduction is to reaction
Equipment is corrosion resistant to be required；
4) after reaction terminates, catalyst can be easily separated with product, and catalyst can be recycled, and advantageously reduces and is produced into
This.
Embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
Embodiment 1
It is 10 by mol ratio:1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight
Percentage is 10% polystyrene sulfonic acid resin catalyst, heating, in 100 DEG C of reaction temperature, reaction pressure 1Mpa condition
Under, stirring carries out esterification.React after 8h, reaction solution is discharged and centrifuged, gained upper strata product is to tert-butyl benzene
Methyl formate, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, methanol, water are first removed by upper strata product revolving,
Then acquisition target product p-tert-butyl benzoic acid methyl esters is rotated again, wherein unreacted p-tert-butyl benzoic acid and Methanol Recovery
Utilize, lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 95%, purity >=99.99%.
Embodiment 2
It is 10 by mol ratio:1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight
Percentage is 10% perfluorinated sulfonic resin catalyst, heating, under conditions of 120 DEG C of reaction temperature, reaction pressure 1.5Mpa,
Stirring, carries out esterification.React after 5h, reaction solution is discharged and centrifuged, gained upper strata product is to tert-butyl benzene first
Sour methyl esters, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, first remove methanol, water, so by upper strata product revolving
Acquisition target product p-tert-butyl benzoic acid methyl esters is rotated again afterwards, wherein unreacted p-tert-butyl benzoic acid and Methanol Recovery profit
With lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 96%, purity >=99.99%.
Embodiment 3
It is 10 by mol ratio:1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight
Percentage is 15% polystyrene sulfonic acid resin catalyst, heating, in 120 DEG C of reaction temperature, reaction pressure 1.5Mpa bar
Under part, stirring carries out esterification.React after 3h, reaction solution is discharged and centrifuged, gained upper strata product is to the tert-butyl group
Methyl benzoate, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, by upper strata product revolving first remove methanol,
Water, then rotates acquisition target product p-tert-butyl benzoic acid methyl esters, wherein unreacted p-tert-butyl benzoic acid and methanol again
Recycle, lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 94%, purity >=99.99%.
Embodiment 4
It is 10 by mol ratio:1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight
Percentage is 5% perfluorinated sulfonic resin catalyst, heating, under conditions of 120 DEG C of reaction temperature, reaction pressure 1.5Mpa,
Stirring, carries out esterification.React after 8h, reaction solution is discharged and centrifuged, gained upper strata product is to tert-butyl benzene first
Sour methyl esters, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, first remove methanol, water, so by upper strata product revolving
Acquisition target product p-tert-butyl benzoic acid methyl esters is rotated again afterwards, wherein unreacted p-tert-butyl benzoic acid and Methanol Recovery profit
With lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 94%, purity >=99.99%.
Embodiment 5
It is 10 by mol ratio:1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight
Percentage is 10% polystyrene sulfonic acid resin catalyst, heating, in 80 DEG C of reaction temperature, reaction pressure 0.8Mpa condition
Under, stirring carries out esterification.React after 8h, reaction solution is discharged and centrifuged, gained upper strata product is to tert-butyl benzene
Methyl formate, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, methanol, water are first removed by upper strata product revolving,
Then acquisition target product p-tert-butyl benzoic acid methyl esters is rotated again, wherein unreacted p-tert-butyl benzoic acid and Methanol Recovery
Utilize, lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 80%, purity >=99.99%.
Embodiment 6
It is 5 by mol ratio:1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight hundred
Point than the perfluorinated sulfonic resin catalyst for 10%, heating under conditions of 140 DEG C of reaction temperature, reaction pressure 2Mpa, is stirred
Mix, carry out esterification.React after 4h, reaction solution is discharged and centrifuged, gained upper strata product is p-tert-butyl benzoic acid
Methyl esters, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, first remove methanol, water, then by upper strata product revolving
Acquisition target product p-tert-butyl benzoic acid methyl esters is rotated again, wherein unreacted p-tert-butyl benzoic acid and Methanol Recovery profit
With lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 94%, purity >=99.99%.
Embodiment 7
It is 20 by mol ratio：1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight
Percentage is 10% polystyrene sulfonic acid resin catalyst, heating, in 100 DEG C of reaction temperature, reaction pressure 1.5Mpa bar
Under part, stirring carries out esterification.React after 4h, reaction solution is discharged and centrifuged, gained upper strata product is to the tert-butyl group
Methyl benzoate, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, by upper strata product revolving first remove methanol,
Water, then rotates acquisition target product p-tert-butyl benzoic acid methyl esters, wherein unreacted p-tert-butyl benzoic acid and methanol again
Recycle, lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 96%, purity >=99.99%.
Embodiment 8
It is 20 by mol ratio：1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight
Percentage is 10% polystyrene sulfonic acid resin catalyst, heating, in 120 DEG C of reaction temperature, reaction pressure 1.6Mpa bar
Under part, stirring carries out esterification.React after 2h, reaction solution is discharged and centrifuged, gained upper strata product is to the tert-butyl group
Methyl benzoate, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, by upper strata product revolving first remove methanol,
Water, then rotates acquisition target product p-tert-butyl benzoic acid methyl esters, wherein unreacted p-tert-butyl benzoic acid and methanol again
Recycle, lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 95%, purity >=99.99%.
Embodiment 9
It is 8 by mol ratio：1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight hundred
Point than the polystyrene sulfonic acid resin catalyst for 10%, heating, in 120 DEG C of reaction temperature, reaction pressure 1.4Mpa condition
Under, stirring carries out esterification.React after 5h, reaction solution is discharged and centrifuged, gained upper strata product is to tert-butyl benzene
Methyl formate, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, methanol, water are first removed by upper strata product revolving,
Then acquisition target product p-tert-butyl benzoic acid methyl esters is rotated again, wherein unreacted p-tert-butyl benzoic acid and Methanol Recovery
Utilize, lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 96%, purity >=99.99%.
Embodiment 10
It is 8 by mol ratio：1 methanol, the raw material of p-tert-butyl benzoic acid are added in reactor, add raw material weight hundred
Point than the polystyrene sulfonic acid resin catalyst for 10%, heating, in 100 DEG C of reaction temperature, reaction pressure 0.9Mpa condition
Under, stirring carries out esterification.React after 8h, reaction solution is discharged and centrifuged, gained upper strata product is to tert-butyl benzene
Methyl formate, water and a small amount of raw material p-tert-butyl benzoic acid, the crude product of methanol, methanol, water are first removed by upper strata product revolving,
Then acquisition target product p-tert-butyl benzoic acid methyl esters is rotated again, wherein unreacted p-tert-butyl benzoic acid and Methanol Recovery
Utilize, lower catalyst agent is recycled.The yield of p-tert-butyl benzoic acid methyl esters is 95%, purity >=99.99%.
Although above having made to retouch in detail to the present invention with general explanation, embodiment and experiment
State, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, are belonged to claimed
Scope.
Claims (9)
1. a kind of method for preparing p-tert-butyl benzoic acid methyl esters, using methanol, p-tert-butyl benzoic acid as raw material, in sulfonate resin
Esterification is carried out in the presence of catalyst, separation produces p-tert-butyl benzoic acid methyl esters.
2. according to the method described in claim 1, it is characterised in that methods described is specially：By methanol, to tert-butyl benzene first
Acid, sulfonate resin mixing, heating carry out esterification, and reaction terminates through separation of solid and liquid, takes liquid phase to produce p-tert-butyl benzoic acid
Methyl esters product；
After the separation of solid and liquid, the azochlorosulfonate acid resin catalyst is retained in solid phase.
3. method according to claim 1 or 2, its spy is being, the described method comprises the following steps：
1) by methanol, p-tert-butyl benzoic acid, sulfuric acid mixed with resin, temperature be 50~200 DEG C, pressure be 0.1~4Mpa's
Under the conditions of, 0.1~15h of stirring is reacted, and obtains reaction solution；
2) by step 1) obtained by reaction solution be centrifuged, take upper strata crude product to carry out revolving processing, produce to the tert-butyl group
Methyl benzoate.
4. according to any described methods of claim 1-3, it is characterised in that the azochlorosulfonate acid resin catalyst is recycled.
5. according to any described methods of claim 1-4, it is characterised in that mole of the p-tert-butyl benzoic acid and methanol
Than for 1:1~1:30, preferably 1:5~1:20, more preferably 1:8~1:10.
6. according to any described methods of claim 1-5, it is characterised in that the azochlorosulfonate acid resin catalyst is selected from polystyrene
It is one or two kinds of in sulfonate resin, perfluorinated sulfonic resin.
7. according to any described methods of claim 1-6, it is characterised in that the weight of the catalyst is the raw material weight
1%~20%, preferably 5%~10%.
8. according to any described methods of claim 3-7, it is characterised in that the pressure of the reaction is 0.8~1.5Mpa；
The temperature of the reaction is 80~140 DEG C；
The time of the reaction is 2~8h.
9. a kind of method for preparing p-tert-butyl benzoic acid methyl esters according to claim 1, it is characterised in that methods described
Comprise the following steps：
1) it is 1 by mol ratio:8~1:10 p-tert-butyl benzoic acid, the raw material of methanol are added in reactor, are added and are accounted for raw material
Percentage by weight is 10% polystyrene sulfonic acid resin or perfluorinated sulfonic resin catalyst, is 100~120 DEG C, pressure in temperature
Power is under conditions of 1~1.6Mpa, 2~8h of stirring is reacted, and obtains reaction solution；
2) by step 1) obtained by reaction solution be centrifuged, take upper strata crude product to carry out revolving processing, produce to the tert-butyl group
Methyl benzoate；
Lower floor is catalyst after the centrifugation, and the catalyst is recycled.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108084021A (en) * | 2017-12-27 | 2018-05-29 | 上海应用技术大学 | A kind of preparation method of isobutyl palmitate |
| CN108658761A (en) * | 2018-04-27 | 2018-10-16 | 宿迁科思化学有限公司 | A kind of preparation of p-tert-butyl benzoic acid methyl esters |
| CN109704960A (en) * | 2018-12-28 | 2019-05-03 | 京博农化科技有限公司 | A kind of synthetic method of m-trifluoromethylbenzoic acid methyl esters |
| CN111302937A (en) * | 2020-04-08 | 2020-06-19 | 北京理工大学 | Method for preparing p-tert-butyl methyl benzoate |
| CN114436829A (en) * | 2020-11-02 | 2022-05-06 | 杭州千泰生物科技有限公司 | Preparation method of phenyl salicylate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4332738A (en) * | 1980-11-24 | 1982-06-01 | Exxon Research & Engineering Co. | Esterification of neo acids by the use of cation exchange resins |
| CN101074197A (en) * | 2007-06-26 | 2007-11-21 | 上海应用技术学院 | Production of p-tert-methyl benzoate by catalysis |
| CN104774284A (en) * | 2014-01-14 | 2015-07-15 | 山东华夏神舟新材料有限公司 | Preparation method of porous perfluorinated sulfonic acid resin for catalysts |
-
2017
- 2017-06-23 CN CN201710486625.7A patent/CN107311868B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4332738A (en) * | 1980-11-24 | 1982-06-01 | Exxon Research & Engineering Co. | Esterification of neo acids by the use of cation exchange resins |
| CN101074197A (en) * | 2007-06-26 | 2007-11-21 | 上海应用技术学院 | Production of p-tert-methyl benzoate by catalysis |
| CN104774284A (en) * | 2014-01-14 | 2015-07-15 | 山东华夏神舟新材料有限公司 | Preparation method of porous perfluorinated sulfonic acid resin for catalysts |
Non-Patent Citations (3)
| Title |
|---|
| G.PIPUS ET AL: "Esterification of benzoic acid in microwave tubular flow reactor", 《CHEMICAL ENGINEERING JOURNAL》 * |
| 姚崇正等: "《精细化工产品合成原理》", 31 March 2000, 中国石化出版社 * |
| 沈玉龙等: "《绿色化学 第2版》", 31 May 2009, 中国环境科学出版社 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108084021A (en) * | 2017-12-27 | 2018-05-29 | 上海应用技术大学 | A kind of preparation method of isobutyl palmitate |
| CN108658761A (en) * | 2018-04-27 | 2018-10-16 | 宿迁科思化学有限公司 | A kind of preparation of p-tert-butyl benzoic acid methyl esters |
| CN109704960A (en) * | 2018-12-28 | 2019-05-03 | 京博农化科技有限公司 | A kind of synthetic method of m-trifluoromethylbenzoic acid methyl esters |
| CN111302937A (en) * | 2020-04-08 | 2020-06-19 | 北京理工大学 | Method for preparing p-tert-butyl methyl benzoate |
| CN114436829A (en) * | 2020-11-02 | 2022-05-06 | 杭州千泰生物科技有限公司 | Preparation method of phenyl salicylate |
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