CN102336658A - Production method of 3,5-dimethylbenzoic acid - Google Patents
Production method of 3,5-dimethylbenzoic acid Download PDFInfo
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- CN102336658A CN102336658A CN2011102149089A CN201110214908A CN102336658A CN 102336658 A CN102336658 A CN 102336658A CN 2011102149089 A CN2011102149089 A CN 2011102149089A CN 201110214908 A CN201110214908 A CN 201110214908A CN 102336658 A CN102336658 A CN 102336658A
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- trimethylbenzene
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- acetaldehyde
- mesitylenic acid
- oxidation
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Abstract
The invention provides a production method of 3,5-dimethylbenzoic acid. The technical scheme adopted by the invention comprises the following steps: a, mixing mesitylene, an acetic acid solvent and a cobalt acetate catalyst; b, then introducing compressed air into an oxidation container containing the mixture for oxidation reaction; c, subsequently, crystallizing and filtering the material after oxidation reaction; and d, finally, rectifying and purifying filter residue to obtain 3,5-dimethylbenzoic acid. According to the treatment method in the invention, reaction heat which is generated when mesitylene is subjected to oxidation reaction is continuously evaporated and condensed by depending on the acetic acid solvent so as to be taken away, thus the temperature is well controlled, and reaction is mild; and oxygen absorption amount can be improved by acetic acid so that oxidation is more complete, thereby improving the yield of the product. Thus, by using the production method in the invention, the conversion rate of mesitylene is improved to 90%.
Description
Technical field
The present invention relates to organic chemistry filed, be specifically related to a kind of 3, the working method of 5-mesitylenic acid.
Background technology
3, the 5-mesitylenic acid is the organic synthesis main intermediate, and it can be used to produce worm hydrazides agricultural chemicals, synthesis of prostaglandins, synthetic fire retardant, softening agent etc.Domestic, on August 14th, 2002 disclosed a kind of production 3, and the method for 5-mesitylenic acid (publication CN1363546), this method are raw material with the sym-trimethylbenzene, do not use solvent to prepare.Because do not have solvent to participate in oxidizing reaction, the sym-trimethylbenzene transformation efficiency is low, the oxidizing temperature fluctuation is bigger, troublesome poeration.
Summary of the invention
It is a kind of 3 that main purpose of the present invention provides, the working method of 5-mesitylenic acid, and this method oxidizing temperature is stable, and transformation efficiency is high.
In order to realize the foregoing invention purpose, the technical scheme that the present invention adopted is: a kind of 3, the working method of 5-mesitylenic acid may further comprise the steps:
A, with sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyst mix;
B, pressurized air is passed into carries out oxidizing reaction in the oxidation container that contains said mixture then;
C, then material after the oxidizing reaction is done crystallization, filtration treatment;
D, at last the filter residue rectification and purification is obtained 3, the 5-mesitylenic acid.
According to treatment process of the present invention, the reaction heat that sym-trimethylbenzene is produced when oxidizing reaction relies on acetate solvate and constantly is evaporated and condensation, thereby is pulled away; Thereby the good control of temperature and reaction temperature with; Acetic acid can also improve oxygen absorbed, makes oxidation more complete, thereby improves product yield.Therefore sym-trimethylbenzene transformation efficiency of the present invention is enhanced, and its transformation efficiency reaches 90%.
Embodiment
A kind of 3, the working method of 5-mesitylenic acid may further comprise the steps:
A, with sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyst mix; B, pressurized air is passed into carries out oxidizing reaction in the oxidation container that contains said mixture then; C, then material after the oxidizing reaction is done crystallization, filtration treatment; D, at last the filter residue rectification and purification is obtained 3, the 5-mesitylenic acid.
In this method: the reaction heat that sym-trimethylbenzene is produced when oxidizing reaction relies on acetate solvate and constantly is evaporated and condensation; Thereby be pulled away, thus the good control of temperature and reaction temperature with, acetic acid can also improve oxygen absorbed; Make oxidation more complete, thereby improve product yield.Therefore sym-trimethylbenzene transformation efficiency of the present invention is enhanced, and its transformation efficiency reaches 90%.Oxidizing reaction tail gas enters atmosphere through washing after the activated carbon adsorption.
Also contain initiator acetaldehyde among the said step a, described sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator acetaldehyde mixing temperature remain on 40～80 ℃.According to the oxidation principle, the sym-trimethylbenzene oxidation belongs to the free radical reaction principle, and the formation of radical depends on initiator.Initiator can be accelerated oxidation rate and shorten oxidization time, and general oxidization time can foreshorten to 2.5～3h.While acetaldehyde becomes acetic acid and can not cause detrimentally affect to tail gas and product in oxidation, and the acetaldehyde price is lower, has reduced production cost.Remain on 40～80 ℃, help the mixing of dissolving each other between the solvent, be beneficial to the transformation efficiency that improves the subsequent oxidation reaction.
Said acetic acid and sym-trimethylbenzene mass ratio are 1～5: 1, and said sym-trimethylbenzene, Cobaltous diacetate, acetaldehyde three mass ratio are 1: 0.1 * 10
-3～20 * 10
-3: 1 * 10
-2～10 * 10
-2, said acetaldehyde is that mass concentration is 40% industrial acetaldehyde.40% industrial acetaldehyde low price has reduced production cost.Under this material ratio, the transformation efficiency of sym-trimethylbenzene oxidizing reaction reaches mxm..
Oxidizing temperature is 100～150 ℃ among the said step b, and pressure is 0.1～0.5MPa, and compressed air require is 100～200m
3/ h; The long-pending content of oxysome reaches oxidation in 19～21% o'clock end in the oxidizing reaction tail gas.Under this oxidation reaction condition, the raw material sym-trimethylbenzene is converted into 3 under the acting in conjunction of solvent, catalyzer, initiator, the reaction of 5-mesitylenic acid.When oxygen level reaches 19～21% in the oxidizing reaction tail gas, just can judge that reaction reaches terminal point, transformation efficiency reaches mxm..
Crystallization among the said step c, filtration treatment be with 0.1MPa pressure with oxidizing reaction after material be depressed in the crystallization kettle and stir, crystallisation by cooling, after the crystallization fully, solid-liquid separation.Wherein filter cake is a bullion 3, the 5-mesitylenic acid, filtrating is dilute acetic acid and a small amount of sym-trimethylbenzene, dilute acetic acid through carry dense after reuse again, the sym-trimethylbenzene that steams returns oxidation container.
Filter residue in the said steps d is done oven dry before rectification and purification handle.Thereby the component volatilization that influences rectification and purification in the filter residue is on a small quantity gone out.
Embodiment 1
A, sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator 40% industrial acetaldehyde is mixed, maintain the temperature at 40 ℃, wherein acetic acid and sym-trimethylbenzene mass ratio are 1: 1, and sym-trimethylbenzene, Cobaltous diacetate, acetaldehyde three mass ratio are 1: 0.1 * 10
-3: 1 * 10
-2
B, pressurized air is passed into carries out oxidizing reaction in the oxidizing tower that contains said mixture then, wherein oxidizing temperature is 100 ℃, and pressure is 0.1MPa, and compressed air require is 200m
3/ h, oxidation finishes when oxygen level reaches 19% in the oxidizing reaction tail gas.
C, then with 0.1MPa pressure with oxidizing reaction after material be depressed in the crystallization kettle and stir, crystallisation by cooling is after crystallization is complete; Solid-liquid separation; Wherein filter cake is a bullion 3, the 5-mesitylenic acid, and filtrating is dilute acetic acid and a small amount of sym-trimethylbenzene; Dilute acetic acid through carry dense after reuse again, the sym-trimethylbenzene that steams returns oxidation container.
D, at last with filter residue oven dry, rectification and purification obtains 3, the 5-mesitylenic acid.
Embodiment 2
A, sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator 40% industrial acetaldehyde is mixed, maintain the temperature at 80 ℃, wherein acetic acid and sym-trimethylbenzene mass ratio are 5: 1, and sym-trimethylbenzene, Cobaltous diacetate, acetaldehyde three mass ratio are 1: 20 * 10
-3: 10 * 10
-2
B, pressurized air is passed into carries out oxidizing reaction in the oxidizing tower that contains said mixture then, wherein oxidizing temperature is 150 ℃, and pressure is 0.5MPa, and compressed air require is 200m
3/ h, oxidation finishes when oxygen level reaches 21% in the oxidizing reaction tail gas.
C, then with 0.1MPa pressure with oxidizing reaction after material be depressed in the crystallization kettle and stir, crystallisation by cooling is after crystallization is complete; Solid-liquid separation; Wherein filter cake is a bullion 3, the 5-mesitylenic acid, and filtrating is dilute acetic acid and a small amount of sym-trimethylbenzene; Dilute acetic acid through carry dense after reuse again, the sym-trimethylbenzene that steams returns oxidation container.
D, at last with filter residue oven dry, rectification and purification obtains 3, the 5-mesitylenic acid.
Embodiment 3
A, sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator 40% industrial acetaldehyde is mixed, maintain the temperature at 60 ℃, wherein acetic acid and sym-trimethylbenzene mass ratio are 3: 1, and sym-trimethylbenzene, Cobaltous diacetate, acetaldehyde three mass ratio are 1: 10 * 10
-3: 6 * 10
-2
B, pressurized air is passed into carries out oxidizing reaction in the oxidizing tower that contains said mixture then, wherein oxidizing temperature is 120 ℃, and pressure is 0.3MPa, and compressed air require is 150m
3/ h, oxidation finishes when oxygen level reaches 20% in the oxidizing reaction tail gas.
C, then with 0.1MPa pressure with oxidizing reaction after material be depressed in the crystallization kettle and stir, crystallisation by cooling is after crystallization is complete; Solid-liquid separation; Wherein filter cake is a bullion 3, the 5-mesitylenic acid, and filtrating is dilute acetic acid and a small amount of sym-trimethylbenzene; Dilute acetic acid through carry dense after reuse again, the sym-trimethylbenzene that steams returns oxidation container.
D, at last with filter residue oven dry, rectification and purification obtains 3, the 5-mesitylenic acid.
Through above examples of implementation, the transformation efficiency of sym-trimethylbenzene has all reached 90% in the oxidizing reaction, and is final 3, and 5-mesitylenic acid product purity reaches more than 98%.
Claims (6)
1. one kind 3, the working method of 5-mesitylenic acid may further comprise the steps:
A, with sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyst mix;
B, pressurized air is passed into carries out oxidizing reaction in the oxidation container that contains said mixture then;
C, then material after the oxidizing reaction is done crystallization, filtration treatment;
D, at last the filter residue rectification and purification is obtained 3, the 5-mesitylenic acid.
2. according to claim 1 a kind of 3; The working method of 5-mesitylenic acid; It is characterized in that: also contain initiator acetaldehyde among the said step a, described sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator acetaldehyde mixing temperature remain on 40～80 ℃.
3. according to claim 1 and 2 a kind of 3, the working method of 5-mesitylenic acid is characterized in that: said acetic acid and sym-trimethylbenzene mass ratio are 1～5: 1, and said sym-trimethylbenzene, Cobaltous diacetate, acetaldehyde three mass ratio are 1: 0.1 * 10
-3～20 * 10
-3: 1 * 10
-2～10 * 10
-2, said acetaldehyde is that mass concentration is 40% industrial acetaldehyde.
4. according to claim 1 a kind of 3, the working method of 5-mesitylenic acid is characterized in that: oxidizing temperature is 100～150 ℃ among the said step b, and pressure is 0.1～0.5MPa, and compressed air require is 100～200m
3/ h; The long-pending content of oxysome reaches oxidation in 19～21% o'clock end in the oxidizing reaction tail gas.
5. according to claim 1 a kind of 3; The working method of 5-mesitylenic acid is characterized in that: crystallization among the said step c, filtration treatment be with 0.1MPa pressure with oxidizing reaction after material be depressed in the crystallization kettle and stir crystallisation by cooling; After the crystallization fully, solid-liquid separation.
6. according to claim 1 a kind of 3, the working method of 5-mesitylenic acid is characterized in that: filter residue in the said steps d is done oven dry handle before rectification and purification.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105085228A (en) * | 2015-07-30 | 2015-11-25 | 山东省农药科学研究院 | Production method for 3, 5-dimethylbenzoic acid |
| CN105152906A (en) * | 2015-09-29 | 2015-12-16 | 衢州群颖化学科技有限公司 | Method for co-producing 3,5-dimethylbenzoic acid and trimesic acid |
| CN108530297A (en) * | 2017-03-03 | 2018-09-14 | 联化科技股份有限公司 | The preparation method of the chloro- 3- methyl benzoic acids of 2- and its intermediate |
| CN111960941A (en) * | 2020-07-31 | 2020-11-20 | 贵州永润天泽化工有限公司 | Purification method of 3, 5-dimethylbenzoic acid |
| CN113248362A (en) * | 2021-05-27 | 2021-08-13 | 成家钢 | 3, 5-dimethyl benzoic acid and continuous preparation method thereof |
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| CN1363546A (en) * | 2002-01-16 | 2002-08-14 | 泰兴市化工七厂 | Homogeneous oxidizing process for preparing 3,5-dimethylbenzoic acid from sym-tritoluene |
| CN101184718A (en) * | 2005-03-08 | 2008-05-21 | 伊士曼化学公司 | Processes for producing aromatic dicarboxylic acids |
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2011
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| CN1363546A (en) * | 2002-01-16 | 2002-08-14 | 泰兴市化工七厂 | Homogeneous oxidizing process for preparing 3,5-dimethylbenzoic acid from sym-tritoluene |
| CN101184718A (en) * | 2005-03-08 | 2008-05-21 | 伊士曼化学公司 | Processes for producing aromatic dicarboxylic acids |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105085228A (en) * | 2015-07-30 | 2015-11-25 | 山东省农药科学研究院 | Production method for 3, 5-dimethylbenzoic acid |
| CN105152906A (en) * | 2015-09-29 | 2015-12-16 | 衢州群颖化学科技有限公司 | Method for co-producing 3,5-dimethylbenzoic acid and trimesic acid |
| CN105152906B (en) * | 2015-09-29 | 2017-07-28 | 江西科苑生物药业有限公司 | A kind of method of the mesitylenic acid of coproduction 3,5 and trimesic acid |
| CN108530297A (en) * | 2017-03-03 | 2018-09-14 | 联化科技股份有限公司 | The preparation method of the chloro- 3- methyl benzoic acids of 2- and its intermediate |
| CN108530297B (en) * | 2017-03-03 | 2021-09-24 | 联化科技股份有限公司 | Preparation method of 2-chloro-3-methylbenzoic acid and intermediate thereof |
| CN111960941A (en) * | 2020-07-31 | 2020-11-20 | 贵州永润天泽化工有限公司 | Purification method of 3, 5-dimethylbenzoic acid |
| CN113248362A (en) * | 2021-05-27 | 2021-08-13 | 成家钢 | 3, 5-dimethyl benzoic acid and continuous preparation method thereof |
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|---|---|
| CN102336658B (en) | 2014-03-26 |
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Denomination of invention: A production method of 3,5-dimethylbenzoic acid Effective date of registration: 20200922 Granted publication date: 20140326 Pledgee: Bank of China Limited Huangshan Branch Pledgor: ANHUI TAIDA NEW MATERIALS Co.,Ltd. Registration number: Y2020980006322 |
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