CN103601639A - O-chlorobenzoic acid synthesis process - Google Patents
O-chlorobenzoic acid synthesis process Download PDFInfo
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- CN103601639A CN103601639A CN201310583266.9A CN201310583266A CN103601639A CN 103601639 A CN103601639 A CN 103601639A CN 201310583266 A CN201310583266 A CN 201310583266A CN 103601639 A CN103601639 A CN 103601639A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
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- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses an o-chlorobenzoic acid synthesis process. The innovation point is that the process adopts o-chlorotoluene as a raw material and acetic acid as a solvent and comprises the following steps: heating to 134-136 DEG C under the effect of the composite catalysts cobalt acetate, manganese acetate and sodium bromide; filling oxygen for reaction, wherein the reaction temperature is 135-145 DEG C, the reaction pressure is 1.0MPa, and the reaction time is 5.5-6.5 hours; and after the reaction, cooling, discharging, cooling, filtering and washing to obtain the target product o-chlorobenzoic acid. The synthesis process disclosed by the invention gives overall consideration to the factors such as raw material cost, production flow, production cost and environmental pollution, and has the advantages of high yield, low cost, short flow, no water pollution and the like.
Description
Technical field
The present invention relates to a kind of synthesis technique of 0-chloro-benzoic acid, be specifically related to that a kind of yield is high, cost is low, flow process is short, the synthesis technique of the 0-chloro-benzoic acid of water pollution-free, belongs to compou nd synthesis technical field.
Background technology
0-chloro-benzoic acid molecular weight is 156.57, colourless needle-like or monoclinic crystal, and 142 ℃ of fusing points, heating is distillation easily, and relative density 1.544, is soluble in alcohol and ether, is dissolved in 900 parts of cold water, and the hot water that is dissolved in, is insoluble to toluene more.0-chloro-benzoic acid is a kind of important meticulous Organic chemical products, dyestuff, agricultural chemicals, important organic synthesis intermediate and the analytical reagent of medicine and other fields, can be used for preparing the medicines such as chlorpromazine, Chlofenamic Acid, Vermox, diclofenac, clotrimazole, the standard reagent of alkalimetry and iodimetry,iodometry, as sanitas, synthetic dyestuff and the color film etc. of glue paste, paint.
It is reported, 0-chloro-benzoic acid can be divided into diazotization method and light chlorinolysis, oxidation style etc. to industry preparation, and wherein oxidation style can be divided into again chemical oxidization method, vapour phase oxidation process and liquid phase oxidation; Chlorination process is divided into thermal chlorination, light chlorinolysis and tower catalysis light chlorination process.
Light chlorination process has that technical process is short, reaction is easy to control, and raw material is easy to get, reaction yield advantages of higher, but its production cost is high, and etching apparatus is serious, produces a large amount of waste liquids, waste gas, causes environmental pollution; Chemistry chlorination process reaction conditions is gentleer, easy and simple to handle, method is ripe, and chemical oxidizing agent price is higher, although the reduzate of some oxygenant can recycling, but still has the processing problem of waste water, waste residue; Liquid phase oxidation oxygenant low price, cost is low, but generally need to be with acetic acid as solvent, and solvent usage quantity is large, therefore cause plant factor low, a large amount of acetic acid needs to recycle, acetic acid corrodibility is strong, the equipment anticorrosions such as conversion unit and acetic acid recovery have been proposed to very high requirement, and in order to guarantee that acetic acid exists with liquid phase under higher temperature of reaction, needs pressurized operation; Air oxidation process oxygenant is cheap, cost is low, good reaction selectivity, but reaction is carried out at a lower temperature, a little less than oxidation capacity, low conversion rate, post-processing operation is complicated, and reaction solution has corrodibility, equipment need to be with good corrosion resistant material, generally need pressurized operation, to increase the solubleness of oxygen, thereby improve speed of response.
Summary of the invention
The object of the invention is to, for deficiency of the prior art, provides a kind of synthesis technique of 0-chloro-benzoic acid.
For solving the problems of the technologies described above, the technical solution used in the present invention is: take ortho-chlorotolu'ene as raw material, acetic acid, as solvent, is heated to 134～136 ℃ under the effect of composite catalyst cobaltous acetate, manganous acetate and Sodium Bromide; Then be filled with oxygen and react, between 135～145 ℃ of temperature of reaction, reaction pressure is 1.0Mpa, 5.5～6.5 hours reaction times; Reaction finishes rear cooling, discharging, and cooling, filters, and washing, obtains target product 0-chloro-benzoic acid.
Further, the mass ratio of described raw material ortho-chlorotolu'ene and solvent is 1:0.1～0.6.
Further, mass ratio 1:0.001～0.01 of described raw material ortho-chlorotolu'ene and composite catalyst.
Further, mass ratio 1:0.4～2:0.5～2 of cobaltous acetate, manganous acetate and Sodium Bromide in described composite catalyst.
Further, the speed that is filled with oxygen described in is 5～20L/min.
Further, the described reaction times is 6 hours.
Beneficial effect of the present invention: synthetic method of the present invention has considered the factors such as raw materials cost, Production Flow Chart, production cost, environmental pollution, has the advantages such as yield is high, cost is low, flow process is short, water pollution-free.
Embodiment
For making objects and advantages of the present invention clearer, below in conjunction with specific embodiment, technical scheme of the present invention is elaborated.
Embodiment 1
Ortho-chlorotolu'ene 280g, acetic acid 150g are dropped in 500ml autoclave pressure, then add composite catalyst cobaltous acetate 0.5g, manganous acetate 0.2g, Sodium Bromide 1.0g, cover autoclave pressure, heating, when temperature rises to 135 ℃, is filled with oxygen, speed 10L/min, is controlled between 135～145 ℃, and pressure reacts 6 hours under 1.0Mpa, cooling, discharging, cooling, filter, washing, obtains product 0-chloro-benzoic acid 340g, content 99.5%(HPLC), fusing point: 139.5～141.2 ℃, yield 98.2%.
Embodiment 2
Ortho-chlorotolu'ene 280g, acetic acid 120g are dropped in 500ml autoclave pressure, then add composite catalyst cobaltous acetate 0.8g, manganous acetate 0.3g, Sodium Bromide 1.2g, cover autoclave pressure, heating, when temperature rises to 135 ℃, is filled with oxygen, speed 15L/min, is controlled between 135～145 ℃, and pressure reacts 6 hours under 1.0Mpa, cooling, discharging, cooling, filter, washing, obtains product 0-chloro-benzoic acid 338g, content 99.4%(HPLC), fusing point: 139.5～141.2 ℃, yield 98.1%.
Above-described embodiment is only in order to illustrate technical scheme of the present invention; but not design of the present invention and protection domain are limited; those of ordinary skill in the art modifies or is equal to replacement technical scheme of the present invention; and not departing from aim and the scope of technical scheme, it all should be encompassed in claim scope of the present invention.
Claims (6)
1. a synthesis technique for 0-chloro-benzoic acid, is characterized in that: take ortho-chlorotolu'ene as raw material, acetic acid, as solvent, is heated to 134～136 ℃ under the effect of composite catalyst cobaltous acetate, manganous acetate and Sodium Bromide; Then be filled with oxygen and react, temperature of reaction is controlled between 135～145 ℃, and reaction pressure is 1.0Mpa, 5.5～6.5 hours reaction times; Reaction finishes rear cooling, discharging, and cooling, filters, and washing, obtains target product 0-chloro-benzoic acid.
2. the synthesis technique of a kind of 0-chloro-benzoic acid according to claim 1, is characterized in that: the mass ratio of described raw material ortho-chlorotolu'ene and solvent is 1:0.1～0.6.
3. the synthesis technique of a kind of 0-chloro-benzoic acid according to claim 1, is characterized in that: described raw material ortho-chlorotolu'ene and mass ratio 1:0.001～0.01 of composite catalyst.
4. the synthesis technique of a kind of 0-chloro-benzoic acid according to claim 1, is characterized in that: mass ratio 1:0.4～2:0.5～2 of cobaltous acetate, manganous acetate and Sodium Bromide in described composite catalyst.
5. the synthesis technique of a kind of 0-chloro-benzoic acid according to claim 1, is characterized in that: described in be filled with oxygen speed be 5～20L/min.
6. the synthesis technique of a kind of 0-chloro-benzoic acid according to claim 1, is characterized in that: the described reaction times is 6 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310583266.9A CN103601639A (en) | 2013-11-20 | 2013-11-20 | O-chlorobenzoic acid synthesis process |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310583266.9A CN103601639A (en) | 2013-11-20 | 2013-11-20 | O-chlorobenzoic acid synthesis process |
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| CN103601639A true CN103601639A (en) | 2014-02-26 |
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| CN201310583266.9A Pending CN103601639A (en) | 2013-11-20 | 2013-11-20 | O-chlorobenzoic acid synthesis process |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107032951A (en) * | 2017-05-12 | 2017-08-11 | 江苏科菲特生化技术股份有限公司 | A kind of method of air catalytic oxidation separation bromobenzene and ortho-chlorotolu'ene mixture |
| CN109772466A (en) * | 2019-01-23 | 2019-05-21 | 厦门中坤化学有限公司 | Cobalt acetate/bromination sodium catalyst recovery method in a kind of catalytic oxidation |
| CN113563174A (en) * | 2018-05-11 | 2021-10-29 | 浙江阿尔法化工科技有限公司 | o-Chlorobenzoic acid production equipment and synthesis method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605757A (en) * | 1983-03-10 | 1986-08-12 | Dynamit Nobel Ag | Method of preparing halogen benzoic acids from toluenes halogenated in the nucleus |
| CN1279128A (en) * | 1999-06-30 | 2001-01-10 | 武汉大学 | Process of preparing halobenzoic acid and its special composite catalyst |
-
2013
- 2013-11-20 CN CN201310583266.9A patent/CN103601639A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605757A (en) * | 1983-03-10 | 1986-08-12 | Dynamit Nobel Ag | Method of preparing halogen benzoic acids from toluenes halogenated in the nucleus |
| CN1279128A (en) * | 1999-06-30 | 2001-01-10 | 武汉大学 | Process of preparing halobenzoic acid and its special composite catalyst |
Non-Patent Citations (1)
| Title |
|---|
| 胡云等: "氯代苯甲酸的合成研究进展", 《广东化工》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107032951A (en) * | 2017-05-12 | 2017-08-11 | 江苏科菲特生化技术股份有限公司 | A kind of method of air catalytic oxidation separation bromobenzene and ortho-chlorotolu'ene mixture |
| CN113563174A (en) * | 2018-05-11 | 2021-10-29 | 浙江阿尔法化工科技有限公司 | o-Chlorobenzoic acid production equipment and synthesis method |
| CN109772466A (en) * | 2019-01-23 | 2019-05-21 | 厦门中坤化学有限公司 | Cobalt acetate/bromination sodium catalyst recovery method in a kind of catalytic oxidation |
| CN109772466B (en) * | 2019-01-23 | 2021-12-24 | 厦门中坤化学有限公司 | Method for recovering cobalt acetate/sodium bromide catalyst in catalytic oxidation reaction |
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Application publication date: 20140226 |