CN111099996A - Preparation method of tert-butyl acrylate - Google Patents
Preparation method of tert-butyl acrylate Download PDFInfo
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- CN111099996A CN111099996A CN201911384902.9A CN201911384902A CN111099996A CN 111099996 A CN111099996 A CN 111099996A CN 201911384902 A CN201911384902 A CN 201911384902A CN 111099996 A CN111099996 A CN 111099996A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
- B01J29/0308—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
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Abstract
The invention discloses a preparation method of tert-butyl acrylate, which comprises the following steps: putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 20-50 ℃ and the pressure of 1-3 MPa at the isobutene volume airspeed of 0.5/h-5.0/h to synthesize tert-butyl acrylate; the feeding molar ratio of acrylic acid to a polymerization inhibitor to isobutene is 1: 0.05-0.2: 0.2-0.8, the catalyst is selected from at least one of strong-acid cation exchange resin, p-toluenesulfonic acid and acid group modified SBA-15 mesoporous molecular sieve, the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 1-3. According to the preparation method of tert-butyl acrylate, the special catalyst and the polymerization inhibitor are combined, so that the yield of the esterification reaction is greatly improved, the reaction temperature is reduced, and the reaction is milder, greener and more economical.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of tert-butyl acrylate.
Background
Tert-butyl acrylate is an extremely important chemical basic raw material and intermediate, and has unique and strong-activity polar molecule, unsaturated double bond and carboxylic ester (-COOR) structure, so that a plurality of polymer formulas with good performance can be derived, and plastic, crosslinking and other polymers can be prepared by processing modes such as emulsion polymerization, solution polymerization, copolymerization and the like. The polymer has the characteristics of strong cohesiveness, good transparency, clear film forming and the like, has great potential in the modification aspect of various chemicals, and is widely applied to the aspects of coatings, papermaking, non-woven fabrics, high water absorption materials, detergents, synthetic fibers, synthetic rubbers, plastics, leather, adhesives and the like. The acrylic acid and the butanol are synthesized by esterification under the catalysis of concentrated sulfuric acid in industry, and the method has the advantages of multiple side reactions, deep product color, complex post-treatment process, serious equipment corrosion and large wastewater discharge.
However, in the conventional process, in order to prepare tert-butyl acrylate, the method mainly adopts esterification synthesis of acrylic acid and tert-butyl alcohol under the catalysis of sulfuric acid, i.e. acrylic acid is used as a raw material to perform esterification reaction with tert-butyl alcohol. And then the final product is obtained through the process steps of extraction, recovery, rectification and the like. The process has the problems of more side reactions, deep product color, complex post-treatment process, serious equipment corrosion, large wastewater discharge, difficult treatment of reaction waste liquid and the like. In addition, in the process of preparing the tertiary alcohol ester by esterifying the carboxylic acid and the corresponding alcohol, because the steric effect of the tertiary butanol is larger, the two competing reactions of esterification and elimination are more prone to elimination, and the purpose of esterification can not be achieved, so that the esterification of the tertiary alcohol is much more difficult than that of primary alcohol and secondary alcohol, and the actual reaction yield is very low.
Chinese patent with publication No. CN104276948A and publication No. 2015, 1 month and 14 days discloses a method for synthesizing tert-butyl (meth) acrylate, and specifically discloses that (meth) acrylic acid and isobutene with a molar ratio of 1.0: 1.0-5.0: 1.0 are esterified with an acidic catalyst at a temperature of 40-120 ℃ and a reaction pressure of 1.0-5.0 MPa to synthesize tert-butyl (meth) acrylate at a volume space velocity of 0.5/h-5.0/h of isobutene. However, the esterification rate of the preparation method is low.
Chinese patent with publication No. CN104987288A and publication No. 2015, 10, 21 discloses a preparation process of tert-butyl acrylate, and specifically discloses that acrylic acid and isobutene with a molar ratio of 1.0: 1.0-5.0: 1.0, together with an acidic catalyst and a polymerization inhibitor are esterified to synthesize tert-butyl acrylate at the temperature of 40-120 ℃ and the reaction pressure of 0.5-5.0 MPa at the volume space velocity of 0.5-5.0/h of isobutene, wherein the polymerization inhibitor is tert-butyl catechol, p-hydroxyanisole, 2, 5-di-tert-butyl hydroquinone and diphenylamine, and the weight ratio of the 4 polymerization inhibitors is 1:3:2: 7. However, the process still has the defects of complex polymerization inhibitor, high reaction temperature and the like.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method of tert-butyl acrylate, wherein a polymerization inhibitor used in the preparation method is simple, the reaction temperature is low, and the esterification rate is high.
In order to solve the technical problem, the invention provides a preparation method of tert-butyl acrylate, which comprises the following steps: putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 20-50 ℃ and the pressure of 1-3 MPa at the isobutene volume airspeed of 0.5/h-5.0/h to synthesize tert-butyl acrylate;
the feeding molar ratio of acrylic acid to a polymerization inhibitor to isobutene is 1: 0.05-0.2: 0.2-0.8, the catalyst is selected from at least one of strong-acid cation exchange resin, p-toluenesulfonic acid and acid group modified SBA-15 mesoporous molecular sieve, the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 1-3.
Further, the mass ratio of tert-butyl catechol to tert-butyl alcohol is 1: 3.
Further, the mass of the catalyst is 5-12% of that of acrylic acid.
Further, the catalyst is a mixture of strong-acid cation exchange resin and p-toluenesulfonic acid, or a mixture of an acid group modified SBA-15 mesoporous molecular sieve and p-toluenesulfonic acid, and the molar ratio of the two is 1-5: 1.
Furthermore, the particle size of the strong-acid cation exchange resin and the acid group modified SBA-15 mesoporous molecular sieve is 0.1-0.25 mm.
Further, the strong-acid cation exchange resin is sulfonic acid type cation exchange resin, and the acid group modified SBA-15 mesoporous molecular sieve is sulfonic acid modified SBA-15 mesoporous molecular sieve.
Further, the reaction temperature is 30-45 ℃.
Further, the pressure is 1 to 1.5 MPa.
Furthermore, the volume space velocity of the isobutene is 1.0/h-3.0/h.
The invention has the beneficial effects that:
1. according to the preparation method of tert-butyl acrylate, the special catalyst and the polymerization inhibitor are combined, so that the yield of the esterification reaction is greatly improved, the reaction temperature is reduced, and the reaction is milder, greener and more economical.
2. The preparation method of tert-butyl acrylate has the advantages of simple process and high utilization rate of raw materials, and does not generate waste acid and waste water and does not need waste acid and waste water treatment.
Detailed Description
The present invention is further described below in conjunction with specific examples to enable those skilled in the art to better understand the present invention and to practice it, but the examples are not intended to limit the present invention.
Example 1
Putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 30 ℃ and the pressure of 1MPa at the volume space velocity of 1.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of the acrylic acid to the polymerization inhibitor to the isobutene is 1:0.1:0.5, the catalyst is a mixture of sulfonic acid type cation exchange resin and p-toluenesulfonic acid, the mass ratio of the sulfonic acid type cation exchange resin to the p-toluenesulfonic acid is 3:1, and the total mass of the catalyst is 10% of the mass of the acrylic acid; the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 1.
Example 2
Putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 30 ℃ and the pressure of 1MPa at the volume space velocity of 1.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of the acrylic acid to the polymerization inhibitor to the isobutene is 1:0.1:0.5, the catalyst is a mixture of a sulfonic acid modified SBA-15 mesoporous molecular sieve and p-toluenesulfonic acid, the mass ratio of the two is 3:1, and the total mass of the catalyst is 10% of the mass of the acrylic acid; the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 1.
Example 3
Putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 30 ℃ and the pressure of 1MPa at the volume space velocity of 1.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of the acrylic acid to the polymerization inhibitor to the isobutene is 1:0.2:0.8, the catalyst is a mixture of a sulfonic acid modified SBA-15 mesoporous molecular sieve and p-toluenesulfonic acid, the mass ratio of the two is 3:1, and the total mass of the catalyst is 8% of the mass of the acrylic acid; the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 1.
Example 4
Putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 30 ℃ and the pressure of 1MPa at the volume space velocity of 1.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of the acrylic acid to the polymerization inhibitor to the isobutene is 1:0.2:0.8, the catalyst is a mixture of a sulfonic acid modified SBA-15 mesoporous molecular sieve and p-toluenesulfonic acid, the mass ratio of the two is 3:1, and the total mass of the catalyst is 8% of the mass of the acrylic acid; the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 3.
Example 5
Putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 40 ℃ and the pressure of 3MPa at the volume space velocity of 3.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of the acrylic acid to the polymerization inhibitor to the isobutene is 1:0.2:0.8, the catalyst is a mixture of a sulfonic acid modified SBA-15 mesoporous molecular sieve and p-toluenesulfonic acid, the mass ratio of the two is 3:1, and the total mass of the catalyst is 8% of the mass of the acrylic acid; the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 3.
Example 6
Putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 40 ℃ and the pressure of 3MPa at the volume space velocity of 3.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of the acrylic acid to the polymerization inhibitor to the isobutene is 1:0.2:0.8, the catalyst is a mixture of a sulfonic acid modified SBA-15 mesoporous molecular sieve and p-toluenesulfonic acid, the mass ratio of the two is 3:1, and the total mass of the catalyst is 12% of the mass of the acrylic acid; the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 3.
Comparative example 1
Putting acrylic acid, a catalyst and isobutene into a reactor, and carrying out esterification reaction at the temperature of 80 ℃ and the pressure of 3MPa at the volume space velocity of 3.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of acrylic acid to isobutene is 1:0.8, the catalyst is sulfonic acid type cation exchange resin, and the mass of the catalyst is 10% of that of the acrylic acid.
Comparative example 2
Putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 60 ℃ and the pressure of 3MPa at the volume space velocity of 3.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of the acrylic acid to the polymerization inhibitor to the isobutene is 1:0.1:0.8, the catalyst is sulfonic acid type cation exchange resin, and the mass of the catalyst is 10% of that of the acrylic acid; the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 5.
Comparative example 3
Putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 60 ℃ and the pressure of 3MPa at the volume space velocity of 3.0/h of the isobutene to synthesize tert-butyl acrylate;
wherein the feeding molar ratio of the acrylic acid to the polymerization inhibitor to the isobutene is 1:0.1:0.8, the catalyst is sulfonic acid type cation exchange resin, and the mass of the catalyst is 10% of that of the acrylic acid; the polymerization inhibitor is a mixture of tert-butyl catechol, p-hydroxyanisole, 2, 5-di-tert-butyl hydroquinone and diphenylamine, and the weight ratio of the 4 polymerization inhibitors is 1:3:2: 7.
The t-butyl acrylates prepared in examples 1-6 and comparative examples 1-3 were tested and the esterification rates determined using standard tests and specifications customary in the art, and the results are given in Table 1.
TABLE 1 esterification rate test results of examples and comparative examples
From the results in table 1, it can be seen that, compared with the comparative example, the preparation method of the present invention greatly increases the yield of the esterification reaction, and simultaneously reduces the temperature required for the reaction, and the reaction is milder, more green and more economical.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (8)
1. A method for preparing tert-butyl acrylate is characterized by comprising the following steps: putting acrylic acid, a catalyst, a polymerization inhibitor and isobutene into a reactor, and carrying out esterification reaction at the temperature of 20-50 ℃ and the pressure of 1-3 MPa at the isobutene volume airspeed of 0.5/h-5.0/h to synthesize tert-butyl acrylate;
the feeding molar ratio of acrylic acid to a polymerization inhibitor to isobutene is 1: 0.05-0.2: 0.2-0.8, the catalyst is selected from at least one of strong-acid cation exchange resin, p-toluenesulfonic acid and acid group modified SBA-15 mesoporous molecular sieve, the polymerization inhibitor is a mixture of tert-butyl catechol and tert-butyl alcohol, and the mass ratio of the two is 1: 1-3.
2. The method of preparing t-butyl acrylate as claimed in claim 1, characterized in that the mass of the catalyst is 5% to 12% of the mass of acrylic acid.
3. The method for preparing tert-butyl acrylate according to claim 1, wherein the catalyst is a mixture of a strong acid cation exchange resin and p-toluenesulfonic acid, or a mixture of an acid group-modified SBA-15 mesoporous molecular sieve and p-toluenesulfonic acid, and the molar ratio of the two is 1-5: 1.
4. The method of claim 1, wherein the particle size of the strong acid cation exchange resin and the acid group modified SBA-15 mesoporous molecular sieve is 0.1-0.25 mm.
5. The method of claim 1, wherein the strong acid cation exchange resin is a sulfonic acid type cation exchange resin and the acid group-modified SBA-15 mesoporous molecular sieve is a sulfonic acid-modified SBA-15 mesoporous molecular sieve.
6. The method for preparing tert-butyl acrylate according to claim 1, wherein the reaction temperature is 30 to 45 ℃.
7. The method of claim 1, wherein the pressure is 1 to 1.5 MPa.
8. The process for preparing tert-butyl acrylate according to claim 1, characterized in that the volume space velocity of isobutene is from 1.0/h to 3.0/h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112062678A (en) * | 2020-09-24 | 2020-12-11 | 岳阳富和科技有限公司 | Method for preventing polymerization in tert-butyl acrylate production process |
| CN114507131A (en) * | 2022-01-24 | 2022-05-17 | 华谊合丰特种化学淄博有限公司 | Synthesis method of tert-butyl (meth) acrylate |
| CN115069294A (en) * | 2022-07-08 | 2022-09-20 | 北京石油化工学院 | Supported catalyst and application thereof in preparation of tert-butylhydroquinone |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924272A (en) * | 2012-11-20 | 2013-02-13 | 南京工业大学 | Method for synthesizing carboxylic ether by performing direct addition to carboxylic acid and alkene |
| CN104844455A (en) * | 2015-04-13 | 2015-08-19 | 徐德良 | Method used for catalyzed synthesis of tert-butyl acrylate |
| CN106040282A (en) * | 2016-05-27 | 2016-10-26 | 南京工业大学 | SO3H-SBA-15 molecular sieve catalyst for catalyzing isobutene and carboxylic acid to synthesize carboxylic acid tert-butyl ester and preparation method and application thereof |
-
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- 2019-12-28 CN CN201911384902.9A patent/CN111099996A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924272A (en) * | 2012-11-20 | 2013-02-13 | 南京工业大学 | Method for synthesizing carboxylic ether by performing direct addition to carboxylic acid and alkene |
| CN104844455A (en) * | 2015-04-13 | 2015-08-19 | 徐德良 | Method used for catalyzed synthesis of tert-butyl acrylate |
| CN106040282A (en) * | 2016-05-27 | 2016-10-26 | 南京工业大学 | SO3H-SBA-15 molecular sieve catalyst for catalyzing isobutene and carboxylic acid to synthesize carboxylic acid tert-butyl ester and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 周峰等: "《SO3H-MCM-41对丙烯酸和异丁烯加成反应的催化性能》", 《石油学报(石油加工)》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112062678A (en) * | 2020-09-24 | 2020-12-11 | 岳阳富和科技有限公司 | Method for preventing polymerization in tert-butyl acrylate production process |
| CN114507131A (en) * | 2022-01-24 | 2022-05-17 | 华谊合丰特种化学淄博有限公司 | Synthesis method of tert-butyl (meth) acrylate |
| CN115069294A (en) * | 2022-07-08 | 2022-09-20 | 北京石油化工学院 | Supported catalyst and application thereof in preparation of tert-butylhydroquinone |
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