CN102336658B - Production method of 3,5-dimethylbenzoic acid - Google Patents
Production method of 3,5-dimethylbenzoic acid Download PDFInfo
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- CN102336658B CN102336658B CN201110214908.9A CN201110214908A CN102336658B CN 102336658 B CN102336658 B CN 102336658B CN 201110214908 A CN201110214908 A CN 201110214908A CN 102336658 B CN102336658 B CN 102336658B
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- trimethylbenzene
- acetaldehyde
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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 production method of 5-mesitylenic acid.
Background technology
3,5-mesitylenic acid is 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 discloses a kind of production 3, the method for 5-mesitylenic acid (publication CN1363546), and this method be take sym-trimethylbenzene as raw material, does not use solvent to be prepared.Owing to not having solvent to participate in oxidizing reaction, sym-trimethylbenzene low conversion rate, oxidizing temperature fluctuation is larger, troublesome poeration.
Summary of the invention
It is a kind of 3 that main purpose of the present invention is to provide, the production method of 5-mesitylenic acid, and the method oxidizing temperature is stable, and transformation efficiency is high.
In order to realize foregoing invention object, the technical solution adopted in the present invention is: a kind of 3, the production method of 5-mesitylenic acid, comprises the following steps:
A, by sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyst mix;
B, then pressurized air is passed into and in the oxidation container that contains said mixture, carries out oxidizing reaction;
C, then material after oxidizing reaction is done to crystallization, filtration treatment;
D, finally filter residue rectification and purification is obtained to 3,5-mesitylenic acid.
According to treatment process of the present invention, the reaction heat that sym-trimethylbenzene produces when oxidizing reaction relies on acetate solvate and is constantly evaporated and condensation, thereby is pulled away, thereby the good control of temperature and reaction temperature and, 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 production method of 5-mesitylenic acid, comprises the following steps:
A, by sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyst mix; B, then pressurized air is passed into and in the oxidation container that contains said mixture, carries out oxidizing reaction; C, then material after oxidizing reaction is done to crystallization, filtration treatment; D, finally filter residue rectification and purification is obtained to 3,5-mesitylenic acid.
In the method: the reaction heat that sym-trimethylbenzene produces when oxidizing reaction relies on acetate solvate and is constantly evaporated and condensation, thereby be pulled away, thus the good control of temperature and reaction temperature and, 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, through washing, enters atmosphere after activated carbon adsorption.
In described step a, also contain initiator acetaldehyde, described sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator acetaldehyde mixing temperature remain on 40～80 ℃.According to oxidation mechanisms, sym-trimethylbenzene oxidation belongs to free radical reaction principle, and the formation of free 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 acetaldehyde price is lower, has reduced production cost.Remain on 40～80 ℃, be conducive to the mixing of dissolving each other between solvent, be beneficial to the transformation efficiency that improves subsequent oxidation reaction.
Described acetic acid and sym-trimethylbenzene mass ratio are 1～5: 1, and described sym-trimethylbenzene, Cobaltous diacetate, acetaldehyde three mass ratio are 1: 0.1 * 10
-3～20 * 10
-3: 1 * 10
-2～10 * 10
-2, described 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 maximum.
In described step b, oxidizing temperature is 100～150 ℃, and pressure is 0.1～0.5MPa, and compressed air require is 100～200m
3/ h; When in oxidizing reaction tail gas, oxygen volume content reaches 19～21%, oxidation finishes.Under this oxidation reaction condition, raw material sym-trimethylbenzene is converted into the reaction of 3,5-mesitylenic acid under the acting in conjunction of solvent, catalyzer, initiator.When oxygen level reaches 19～21% in oxidizing reaction tail gas, just can judge that reaction reaches terminal, transformation efficiency reaches maximum.
Crystallization in described step c, filtration treatment are with 0.1MPa pressure, material after oxidizing reaction to be depressed in crystallization kettle and to be stirred, crystallisation by cooling, and after crystallization completely, solid-liquid separation.Wherein filter cake is crude product 3,5-mesitylenic acid, and filtrate is dilute acetic acid and a small amount of sym-trimethylbenzene, and dilute acetic acid is reuse again after concentrate, and the sym-trimethylbenzene steaming returns to oxidation container.
Filter residue in described steps d is done to drying and processing before rectification and purification.Thereby the component volatilization that affects on a small quantity rectification and purification in filter residue is gone out.
Embodiment 1
A, the industrial acetaldehyde of sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator 40% 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, then pressurized air is passed in the oxidizing tower that contains said mixture and carries out oxidizing reaction, wherein oxidizing temperature is 100 ℃, and pressure is 0.1MPa, and compressed air require is 200m
3/ h, when in oxidizing reaction tail gas, oxygen level reaches 19%, oxidation finishes.
C, then with 0.1MPa pressure, material after oxidizing reaction is depressed in crystallization kettle and is stirred, crystallisation by cooling, after crystallization completely, solid-liquid separation, wherein filter cake is crude product 3,5-mesitylenic acid, and filtrate is dilute acetic acid and a small amount of sym-trimethylbenzene, dilute acetic acid is reuse again after concentrate, and the sym-trimethylbenzene steaming returns to oxidation container.
D, finally filter residue is dried, rectification and purification obtains 3,5-mesitylenic acid.
Embodiment 2
A, the industrial acetaldehyde of sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator 40% 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, then pressurized air is passed in the oxidizing tower that contains said mixture and carries out oxidizing reaction, wherein oxidizing temperature is 150 ℃, and pressure is 0.5MPa, and compressed air require is 200m
3/ h, when in oxidizing reaction tail gas, oxygen level reaches 21%, oxidation finishes.
C, then with 0.1MPa pressure, material after oxidizing reaction is depressed in crystallization kettle and is stirred, crystallisation by cooling, after crystallization completely, solid-liquid separation, wherein filter cake is crude product 3,5-mesitylenic acid, and filtrate is dilute acetic acid and a small amount of sym-trimethylbenzene, dilute acetic acid is reuse again after concentrate, and the sym-trimethylbenzene steaming returns to oxidation container.
D, finally filter residue is dried, rectification and purification obtains 3,5-mesitylenic acid.
Embodiment 3
A, the industrial acetaldehyde of sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator 40% 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, then pressurized air is passed in the oxidizing tower that contains said mixture and carries out oxidizing reaction, wherein oxidizing temperature is 120 ℃, and pressure is 0.3MPa, and compressed air require is 150m
3/ h, when in oxidizing reaction tail gas, oxygen level reaches 20%, oxidation finishes.
C, then with 0.1MPa pressure, material after oxidizing reaction is depressed in crystallization kettle and is stirred, crystallisation by cooling, after crystallization completely, solid-liquid separation, wherein filter cake is crude product 3,5-mesitylenic acid, and filtrate is dilute acetic acid and a small amount of sym-trimethylbenzene, dilute acetic acid is reuse again after concentrate, and the sym-trimethylbenzene steaming returns to oxidation container.
D, finally filter residue is dried, rectification and purification obtains 3,5-mesitylenic acid.
By above examples of implementation, in oxidizing reaction, the transformation efficiency of sym-trimethylbenzene has all reached 90%, final 3, and 5-mesitylenic acid product purity reaches more than 98%.
Claims (3)
1. one kind 3, the production method of 5-mesitylenic acid, comprises the following steps:
A, sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator acetaldehyde are mixed;
B, then pressurized air is passed into and in the oxidation container that contains said mixture, carries out oxidizing reaction;
C, then material after oxidizing reaction is done to crystallization, filtration treatment;
D, finally filter residue rectification and purification is obtained to 3,5-mesitylenic acid;
In described step a, sym-trimethylbenzene, acetate solvate, Cobaltous diacetate catalyzer, initiator acetaldehyde mixing temperature remain on 40～80 ℃;
Described acetic acid and sym-trimethylbenzene mass ratio are 1～5:1, and sym-trimethylbenzene, Cobaltous diacetate, acetaldehyde three mass ratio are 1:0.1 * 10
-3～20 * 10
-3: 1 * 10
-2～10 * 10
-2, acetaldehyde is that mass concentration is 40% industrial acetaldehyde;
In described step b, oxidizing temperature is 100～150 ℃, and pressure is 0.1～0.5MPa, and compressed air require is 100～200m
3/ h; When in oxidizing reaction tail gas, oxygen volume content reaches 19～21%, oxidation finishes.
2. according to claim 1 a kind of 3, the production method of 5-mesitylenic acid, is characterized in that: crystallization in described step c, filtration treatment are with 0.1MPa pressure, material after oxidizing reaction to be depressed in crystallization kettle and to be stirred, crystallisation by cooling, after crystallization completely, solid-liquid separation.
3. according to claim 1 a kind of 3, the production method of 5-mesitylenic acid, is characterized in that: filter residue in described steps d is done to drying and processing before rectification and purification.
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| CN201110214908.9A CN102336658B (en) | 2011-07-29 | 2011-07-29 | Production method of 3,5-dimethylbenzoic acid |
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| CN201110214908.9A CN102336658B (en) | 2011-07-29 | 2011-07-29 | Production method of 3,5-dimethylbenzoic acid |
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| CN102336658B true CN102336658B (en) | 2014-03-26 |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105085228B (en) * | 2015-07-30 | 2017-07-11 | 山东省农药科学研究院 | A kind of production method of 3,5 mesitylenic 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 |
| 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 |
| CN113248362B (en) * | 2021-05-27 | 2023-03-31 | 成家钢 | 3,5-dimethyl benzoic acid and continuous preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2011
- 2011-07-29 CN CN201110214908.9A patent/CN102336658B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (4)
| Title |
|---|
| "3’5-二甲基苯甲酸的制备";李宁 等;《化学与粘合》;20011231(第3期);第127-128，132页 * |
| "二甲基苯甲酸的制备";崔宝军 等;《化学与粘合》;20011231(第1期);第82-83页 * |
| 崔宝军 等."二甲基苯甲酸的制备".《化学与粘合》.2001,(第1期),第82-83页. |
| 李宁 等."3’5-二甲基苯甲酸的制备".《化学与粘合》.2001,(第3期),第127-128，132页. |
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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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Date of cancellation: 20210809 Granted publication date: 20140326 Pledgee: Bank of China Limited Huangshan Branch Pledgor: ANHUI TAIDA NEW MATERIALS Co.,Ltd. Registration number: Y2020980006322 |