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 PDF

Info

Publication number
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
Authority
CN
China
Prior art keywords
tert
benzoic acid
butyl benzoic
catalyst
methanol
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.)
Granted
Application number
CN201710486625.7A
Other languages
Chinese (zh)
Other versions
CN107311868B (en
Inventor
吴芹
黎汉生
周广增
宋淑芬
任荣
史大昕
成金玉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Juancheng Dingsheng Chemical Technology Co Ltd
Beijing Institute of Technology BIT
Original Assignee
Juancheng Dingsheng Chemical Technology Co Ltd
Beijing Institute of Technology BIT
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Juancheng Dingsheng Chemical Technology Co Ltd, Beijing Institute of Technology BIT filed Critical Juancheng Dingsheng Chemical Technology Co Ltd
Priority to CN201710486625.7A priority Critical patent/CN107311868B/en
Publication of CN107311868A publication Critical patent/CN107311868A/en
Application granted granted Critical
Publication of CN107311868B publication Critical patent/CN107311868B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/08Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/584Recycling of catalysts

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

A kind of method for preparing p-tert-butyl benzoic acid methyl esters
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.
CN201710486625.7A 2017-06-23 2017-06-23 Method for preparing p-tert-butyl methyl benzoate Active CN107311868B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710486625.7A CN107311868B (en) 2017-06-23 2017-06-23 Method for preparing p-tert-butyl methyl benzoate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710486625.7A CN107311868B (en) 2017-06-23 2017-06-23 Method for preparing p-tert-butyl methyl benzoate

Publications (2)

Publication Number Publication Date
CN107311868A true CN107311868A (en) 2017-11-03
CN107311868B CN107311868B (en) 2020-05-22

Family

ID=60181084

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710486625.7A Active CN107311868B (en) 2017-06-23 2017-06-23 Method for preparing p-tert-butyl methyl benzoate

Country Status (1)

Country Link
CN (1) CN107311868B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
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

Citations (3)

* Cited by examiner, † Cited by third party
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 (4)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
CN107311868B (en) 2020-05-22

Similar Documents

Publication Publication Date Title
CN107311868A (en) A kind of method for preparing p-tert-butyl benzoic acid methyl esters
CN104447443A (en) Preparation method for apremilast and intermediate of apremilast
CN103212437A (en) Method for preparing titanium-based catalyst and synthesizing epoxypropane and dicumyl peroxide
CN104151164A (en) Method for preparing methyl chloroacetate
CN102311420B (en) Method for synthesizing epsilon-caprolactone
CN104557809A (en) Method for producing furfural from pentose
CN107056670B (en) A kind of preparation method of two tertiary base peroxide
CN101838198A (en) Method for preparing carboxylic ester
CN103387495A (en) Method for continuously preparing carboxylic acid ester
CN105523982A (en) Method for preparing tert-butyl hydroperoxide
CN102464633B (en) Synthetic method for (methyl) glycidyl acrylate
Journoux-Lapp et al. Elucidation of the role of betaine hydrochloride in glycerol esterification: Towards bio-based ionic building blocks
CN106631684A (en) Method for preparing SBA(sec-butyl alcohol) through hydrolysis with sec-butyl acetate
CN101544587B (en) Preparation method of alpha, alpha'-bis(tert-butyl peroxy) diisopropylbenzene
CN105237453A (en) Method used for preparing methylethyl ketone peroxide by taking acidic ion exchange resin as catalyst
CN106187703B (en) A kind of preparation method of pyrogallic acid
CN102557932B (en) Method for producing isobutyl acetate
CN103709004A (en) Preparation method of 1, 3-propanediol
CN105585468B (en) A method of cyclopentanone is prepared by raw material of cyclopentene
CN106946697A (en) A kind of method for synthesizing trioctyl trimellitate (TOTM)
CN103319383A (en) Preparation method of p-methylsulfonylbenzoic acid
CN107032986A (en) A kind of method that presence of acidic ionic liquid catalyst synthesizes the propanol ether acetate of 2 methoxyl group 1
CN209810143U (en) Low boiling point alcohol continuous esterification reaction rectification system
CN103664520B (en) The method of Virahol is prepared in a kind of propylene hydration reaction
CN102557877A (en) Method for increasing yield of terpinol in near homogenous phase double-phase reaction system

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant