CN102491894A - Preparation method of 2,4,6-trimethylbenzoic acid - Google Patents
Preparation method of 2,4,6-trimethylbenzoic acid Download PDFInfo
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- CN102491894A CN102491894A CN2011103883807A CN201110388380A CN102491894A CN 102491894 A CN102491894 A CN 102491894A CN 2011103883807 A CN2011103883807 A CN 2011103883807A CN 201110388380 A CN201110388380 A CN 201110388380A CN 102491894 A CN102491894 A CN 102491894A
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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
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- Y02P20/584—Recycling of catalysts
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Abstract
The invention discloses a preparation method of 2,4,6-trimethylbenzoic acid, which comprises the following steps: proportionally putting sym-trimethyl benzene and a catalyst into a reaction kettle, introducing carbon dioxide gas, maintaining the system to react for 6-12 hours, adding a certain amount of hydrochloric acid and water to react, recycling the catalyst from the water phase, and cooling the oil phase to crystallize, thereby obtaining the 2,4,6-trimethylbenzoic acid product. The invention has the advantages of fewer steps and simple preparation technique, and is an economical and green chemical reaction of atoms.
Description
Technical field
The invention belongs to the fine chemical product preparing technical field, especially relate to a kind of preparation method of mesitylene carboxylic acid.
Background technology
Mesitylene carboxylic acid is the important intermediate of preparation agricultural chemicals, medicine and light trigger etc.Mesitylene carboxylic acid tradition synthetic route has: the hydrolysis under the aluminum trichloride (anhydrous) effect of sym-trimethylbenzene and oxalyl chloride makes; Sym-trimethylbenzene makes with carbonic acid gas addition hydrolysis behind the bromination grignard reaction again; Sym-trimethylbenzene and chloroacetyl chloride generation acylation reaction, hydrolysis and getting again after haloform reaction again.Shortcomings such as this several method all exists reactions step many, and process is complicated, and the raw material atom utilization is low, and three waste discharge is serious.The open CN 100569726C of Chinese patent has stated with the chloroacetyl chloride to be that acylating agent and sym-trimethylbenzene carry out acylation reaction and make 2,4,6-trimethylammonium chloroacetophenone; 2; 4,6-trimethylammonium chloroacetophenone and Youxiaolin carry out haloform reaction in the presence of phase-transfer catalyst, and reactant obtains 2 through separatory, neutralization, recrystallization again; 4, the 6-trimethylbenzoic acid.This invention is raw materials used more with reactions step, and product yield is lower, and the production process three waste discharge is comparatively serious.
Summary of the invention
The objective of the invention is: overcome the problem that prior art exists, the preparation method of the mesitylene carboxylic acid that a kind of reactions step is few, preparation technology is easy is provided.
Technical scheme of the present invention is: may further comprise the steps:
(1) sym-trimethylbenzene and catalyzer are dropped in the reaction kettle by a certain percentage, reactor temperature is at 10-25 ℃;
(2) under the whipped state, in reaction kettle, feed dioxide gas, keep temperature of reaction, still internal pressure 0.18-0.4Mpa, maintenance system reaction 6-12 hour at 10-25 ℃;
(3) in above-mentioned reaction system, add a certain amount of hydrochloric acid and water, be warming up to 65-75 ℃ and keep phase-splitting after 1-2 hour, water reclaims catalyzer, and the oil phase crystallisation by cooling obtains mesitylene carboxylic acid product, mother liquid recycle.
Said sym-trimethylbenzene and catalyzer are by weight percentage: sym-trimethylbenzene accounts for 96-99.5 %, and catalyzer accounts for 0.5-4%.
Said catalyzer and carbonic acid gas weight ratio are 1:8-20.
The invention has the beneficial effects as follows: the present invention is carboxylating agent with the carbonic acid gas, in the presence of catalyzer, and the phenyl ring of direct carboxylation sym-trimethylbenzene; Reactant obtains 2 through hydrolysis, separatory, crystallization; 4,6-trimethylbenzoic acid product is to use the direct carboxylation phenyl ring of carbonic acid gas single stage method preparation 2; 4,6-trimethylbenzoic acid method.Raw material is simple and easy to, and reactions step is few, and preparation technology is easy, is the reaction of atom economy and Green Chemistry.
Embodiment
Following instance is used to specify the present invention, should not think the qualification to the scope of the invention, and except that specializing, inventory all is meant weight.
Embodiment 1:
1200kg sym-trimethylbenzene, 20kg catalyzer are dropped in the reaction kettle, open and stir, reactor temperature added the 220kg dioxide gas in the reaction kettle at 15 ℃ in 5 hours continuously again, kept temperature of reaction 15-25 ℃, and the still internal pressure is 0.18-0.4MPa.Carbonic acid gas is reinforced to finish, and temperature of reaction is risen to 24 ± 1 ℃, keeps reaction 1 hour.Reaction finishes, and adds 30kg hydrochloric acid and water, is warming up to 65 ℃, stirs phase-splitting after 1 hour.Catalyzer is reclaimed in the water distillation, and the oil phase crystallization obtains the mesitylene carboxylic acid product.
Embodiment 2:
1200kg sym-trimethylbenzene, 20kg catalyzer are dropped in the reaction kettle, open and stir, reactor temperature added the 220kg dioxide gas in the reaction kettle at 10 ℃ in 6 hours continuously again, kept 20 ± 2 ℃ of temperature of reaction, and the still internal pressure is 0.18-0.4MPa.Carbonic acid gas is reinforced to finish, and temperature of reaction is risen to 23 ± 2 ℃, keeps reaction 1 hour.Reaction finishes, and adds 30kg hydrochloric acid and water, is warming up to 70 ℃, stirs phase-splitting after 1.5 hours.Catalyzer is reclaimed in the water distillation, and the oil phase crystallization obtains the mesitylene carboxylic acid product.
Embodiment 3:
1200kg sym-trimethylbenzene, 20kg catalyzer are dropped in the reaction kettle, open and stir, reactor temperature added the 220kg dioxide gas in the reaction kettle at 10 ℃ in 7 hours continuously again, kept 24 ± 1 ℃ of temperature of reaction, and the still internal pressure is 0.18-0.3MPa.Carbonic acid gas is reinforced to finish, and temperature of reaction is risen to 24 ± 1 ℃, keeps reaction 1 hour.Reaction finishes, and adds 30kg hydrochloric acid and water, is warming up to 70 ℃, stirs phase-splitting after 2 hours.Catalyzer is reclaimed in the water distillation, and the oil phase crystallization obtains the mesitylene carboxylic acid product.
Embodiment 4:
1200kg sym-trimethylbenzene, 25kg catalyzer are dropped in the reaction kettle, open and stir, reactor temperature added the 220kg dioxide gas in the reaction kettle at 15 ℃ in 8 hours continuously again, kept 20 ± 1 ℃ of temperature of reaction, 0.18-0.4MPa.Carbonic acid gas is reinforced to finish, and temperature of reaction is risen to 20 ± 1 ℃, keeps reaction 1 hour.Reaction finishes, and adds 30kg hydrochloric acid and water, is warming up to 75 ℃, stirs phase-splitting after 1 hour.Catalyzer is reclaimed in the water distillation, and the oil phase crystallization obtains the mesitylene carboxylic acid product.
Embodiment 5:
1200kg sym-trimethylbenzene, 11kg catalyzer are dropped in the reaction kettle, open and stir, reactor temperature added the 220kg dioxide gas in the reaction kettle at 15 ℃ in 9 hours continuously again, kept 20 ± 1 ℃ of temperature of reaction, and the still internal pressure is 0.18-0.3MPa.Carbonic acid gas is reinforced to finish, and temperature of reaction is risen to 24 ± 1 ℃, keeps reaction 1 hour.Reaction finishes, and adds 30kg hydrochloric acid and water, is warming up to 70 ℃, stirs phase-splitting after 1.5 hours.Catalyzer is reclaimed in the water distillation, and the oil phase crystallization obtains the mesitylene carboxylic acid product.
Embodiment 6:
1200kg sym-trimethylbenzene, 22kg catalyzer are dropped in the reaction kettle, open and stir, reactor temperature added the 440kg dioxide gas in the reaction kettle at 15 ℃ in 10 hours continuously again, kept 22 ± 1 ℃ of temperature of reaction, and the still internal pressure is 0.18-0.4MPa.Carbonic acid gas is reinforced to finish, and temperature of reaction is risen to 24 ± 1 ℃, keeps reaction 1 hour.Reaction finishes, and adds 30kg hydrochloric acid and water, is warming up to 72 ℃, stirs phase-splitting after 1 hour.Catalyzer is reclaimed in the water distillation, and the oil phase crystallization obtains the mesitylene carboxylic acid product.
Embodiment 7:
1200kg sym-trimethylbenzene, 40kg catalyzer are dropped in the reaction kettle, open and stir, reactor temperature added the 330kg dioxide gas in the reaction kettle at 15 ℃ in 11 hours continuously again, kept 22 ± 1 ℃ of temperature of reaction, and the still internal pressure is 0.18-0.4MPa.Carbonic acid gas is reinforced to finish, and temperature of reaction is risen to 23 ± 1 ℃, keeps reaction 1 hour.Reaction finishes, and adds 30kg hydrochloric acid and water, is warming up to 70 ℃, stirs phase-splitting after 1 hour.Catalyzer is reclaimed in the water distillation, and the oil phase crystallization obtains the mesitylene carboxylic acid product.
Claims (3)
1. the preparation method of a mesitylene carboxylic acid is characterized in that: may further comprise the steps:
(1) sym-trimethylbenzene and catalyzer are dropped in the reaction kettle by a certain percentage, reactor temperature is at 10-25 ℃;
(2) under the whipped state, in reaction kettle, feed dioxide gas, keep temperature of reaction, still internal pressure 0.18-0.4Mpa, maintenance system reaction 6-12 hour at 10-25 ℃;
(3) in above-mentioned reaction system, add a certain amount of hydrochloric acid and water, be warming up to 65-75 ℃ and keep phase-splitting after 1-2 hour, water reclaims catalyzer, and the oil phase crystallisation by cooling obtains mesitylene carboxylic acid product, mother liquid recycle.
2. the preparation method of mesitylene carboxylic acid according to claim 1, it is characterized in that: said sym-trimethylbenzene and catalyzer are by weight percentage: sym-trimethylbenzene accounts for 96-99.5 %, and catalyzer accounts for 0.5-4%.
3. the preparation method of mesitylene carboxylic acid according to claim 1, it is characterized in that: said catalyzer and carbonic acid gas weight ratio are 1:8-20.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103883807A CN102491894A (en) | 2011-11-30 | 2011-11-30 | Preparation method of 2,4,6-trimethylbenzoic acid |
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| CN2011103883807A CN102491894A (en) | 2011-11-30 | 2011-11-30 | Preparation method of 2,4,6-trimethylbenzoic acid |
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| CN102491894A true CN102491894A (en) | 2012-06-13 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9018153B1 (en) | 2013-11-13 | 2015-04-28 | The Clorox Company | Mesitylene sulfonate compositions and methods thereof |
| CN104710298A (en) * | 2015-03-10 | 2015-06-17 | 华东理工大学 | Strong polar mixed solvent and application thereof |
| US9074166B1 (en) | 2013-11-13 | 2015-07-07 | The Clorox Company | Method for bleaching a surface with a mesitylene sulfonate composition |
| CN109320412A (en) * | 2018-12-04 | 2019-02-12 | 贵州新天鑫化工有限公司 | A kind of preparation method of 2,4,6- trimethylbenzoic acid |
| CN110386868A (en) * | 2018-04-23 | 2019-10-29 | 天津墨森科技有限公司 | The preparation method of one kind 2,4,6- trimethylbenzoic acid |
| CN111269108A (en) * | 2020-01-20 | 2020-06-12 | 泰安渤洋化工科技有限公司 | Continuous hydrolysis device and method for 2,4,6 trimethyl benzoic acid acylation liquid |
| CN115108902A (en) * | 2022-03-29 | 2022-09-27 | 泰安渤洋化工科技有限公司 | Preparation method of 2,4, 6-trimethyl benzoic acid |
-
2011
- 2011-11-30 CN CN2011103883807A patent/CN102491894A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 韩庆荣等: "傅-克反应合成2,4,6-三甲基苯甲酸工艺的改进", 《化学与生物工程》 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9018153B1 (en) | 2013-11-13 | 2015-04-28 | The Clorox Company | Mesitylene sulfonate compositions and methods thereof |
| US9074166B1 (en) | 2013-11-13 | 2015-07-07 | The Clorox Company | Method for bleaching a surface with a mesitylene sulfonate composition |
| US9074165B1 (en) | 2013-11-13 | 2015-07-07 | The Clorox Company | Liquid mesitylene sulfonate compositions and methods thereof |
| US9120999B2 (en) | 2013-11-13 | 2015-09-01 | The Clorox Company | Mesitylene sulfonate compositions and methods for cleaning a surface |
| CN104710298A (en) * | 2015-03-10 | 2015-06-17 | 华东理工大学 | Strong polar mixed solvent and application thereof |
| CN104710298B (en) * | 2015-03-10 | 2016-08-24 | 华东理工大学 | A kind of highly polar mixed solvent and application thereof |
| CN110386868A (en) * | 2018-04-23 | 2019-10-29 | 天津墨森科技有限公司 | The preparation method of one kind 2,4,6- trimethylbenzoic acid |
| CN109320412A (en) * | 2018-12-04 | 2019-02-12 | 贵州新天鑫化工有限公司 | A kind of preparation method of 2,4,6- trimethylbenzoic acid |
| CN109320412B (en) * | 2018-12-04 | 2021-05-25 | 贵州新天鑫化工有限公司 | Preparation method of 2,4, 6-trimethyl benzoic acid |
| CN111269108A (en) * | 2020-01-20 | 2020-06-12 | 泰安渤洋化工科技有限公司 | Continuous hydrolysis device and method for 2,4,6 trimethyl benzoic acid acylation liquid |
| CN111269108B (en) * | 2020-01-20 | 2023-08-22 | 泰安渤洋化工科技有限公司 | Continuous hydrolysis device and method for 2,4,6 trimethyl benzoic acid acylation liquid |
| CN115108902A (en) * | 2022-03-29 | 2022-09-27 | 泰安渤洋化工科技有限公司 | Preparation method of 2,4, 6-trimethyl benzoic acid |
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Application publication date: 20120613 |