CN104058947A - Chloroacetic acid production method capable of reducing acetic anhydride consumption - Google Patents
Chloroacetic acid production method capable of reducing acetic anhydride consumption Download PDFInfo
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- CN104058947A CN104058947A CN201410249461.2A CN201410249461A CN104058947A CN 104058947 A CN104058947 A CN 104058947A CN 201410249461 A CN201410249461 A CN 201410249461A CN 104058947 A CN104058947 A CN 104058947A
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- acetic acid
- acetyl chloride
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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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
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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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
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Abstract
The invention discloses a chloroacetic acid production method capable of reducing acetic anhydride consumption. The method comprises the following steps: by using acetyl chloride generated by acetic anhydride and HCl as a true catalyst, reacting acetic acid and chlorine to generate chloroacetic acid and HCl, distilling, carrying out catalytic hydrogenation, and carrying out two-step distillation to obtain the high-grade chloroacetic acid. By canceling the hydrolysis reaction and increasing the one-step distillation reaction, the generated acetyl chloride is recovered and reutilized, and the HCl in the chlorination mother solution is distilled off, so that the concentration of the acetyl chloride in the reactor can be ensured without adding too much acetic anhydride, thereby reducing the acetic anhydride consumption, reducing the heavy component generation quantity, enhancing the product yield, lowering the HCl content in the chlorination mother solution and enhancing the hydrogenation reaction efficiency.
Description
Technical field
The present invention relates to a kind of chloroacetic production method, be specifically related to a kind of production of chloroacetic acid method that reduces aceticanhydride usage quantity.
Background technology
Mono Chloro Acetic Acid industrial process only has two kinds: trieline hydrolysis method and Catalytic Chlorination of acetic acid method.Trieline hydrolysis method is to take the vitriol oil as catalyzer, carries out addition and the hydrolysis reaction of water simultaneously.Trieline hydrolysis method because of technological process compared with simple, product purity compared with high and developed, Europe once adopted this technique to build industrial production device, but because raw material is expensive, superseded in recent years.Acetic acid catalytic chlorination process is under the effect of catalyzer (as the halogenide of iodine, phosphorus, sulphur or sulphur and phosphorus and aceticanhydride etc.), in the time of 95～140 ℃, acetic acid and chlorine carry out chlorination reaction and generate Monochloro Acetic Acid in one or several tandem reactor, and a small amount of dichloro acetic acid of by-product is trichoroacetic acid(TCA) even.Due to the existence of by product, reaction product is that chlorination mother solution must just can obtain highly purified Mono Chloro Acetic Acid product after the purification process such as crystallization or hydrogenation.Due to crystallizing chloroacetic acid mother liquid disposal complex procedures, various, much brought again secondary pollution, can not eradicate pollution, so be also eliminated gradually.
Many employing acetic anhydride catalysis acetic acid chlorination both at home and abroad (Acetyl Chloride 98Min. that aceticanhydride and HCL generate is catalyzer actual in reaction process) at present, adopt palladium-carbon catalyst hydrodechlorination reduction chlorination mother solution to produce chloroacetic technique, to after dichloro acetic acid, trichoroacetic acid(TCA) hydrogenation, generate Monochloro Acetic Acid and hydrogenchloride, thereby reduced to greatest extent the generation of mother liquor, reduced the pressure of factory to environment.Above-mentioned continuous processing preparation process for chloroacetic acid, chlorination reaction pressure is at 0.3～0.6MPaG, and temperature of reaction is at 95～160 ℃.Before hydrogenation reaction, need the chlorination mother solution processing that is hydrolyzed, the Acetyl Chloride 98Min. in chlorination mother solution and water generation hydration reaction, be converted into acetic acid and HCl by Acetyl Chloride 98Min., thereby avoid Acetyl Chloride 98Min. to enter hydrogenator, generates by product.Current production technique, 1) in chlorination reactor, HCl and aceticanhydride first react, and generate Acetyl Chloride 98Min. (actual catalyst of reaction), and the chlorination reaction of catalysis acetic acid and Cl2 generates Mono Chloro Acetic Acid and HCL.Also can there are some side reactions, as dichloro acetic acid etc. simultaneously.2) from chlorination reactor mother liquor out, enter water reactor.In water reactor, the Acetyl Chloride 98Min. in chlorination resultant and water generation hydration reaction, Acetyl Chloride 98Min. is converted into acetic acid and HCl, thereby prevents that the Acetyl Chloride 98Min. that reaction generates from entering hydrogenator.3) from hydrolysis reactor mother liquor out, enter hydrogenation reactor, under the effect of catalyzer, by hydrogenation, 90% above dichloro acetic acid is reduced into Mono Chloro Acetic Acid, reduce dichloro acetic acid impurity concentration, have 2～5% Mono Chloro Acetic Acid to be hydrogenated simultaneously and be reduced to acetic acid; In addition in mother liquor, acetaldehyde is produced in remaining Acetyl Chloride 98Min. meeting and hydrogen generation side reaction, and acetaldehyde will generate heavy constituent complex compound with other organism under the effect of hydrogen and catalyzer.4) from hydrogenation reactor mother liquor out, first enter light constituent distillation tower, light ends (water and acetic acid) distills with gas phase form, after condenser condenses, is back to recycle in chlorination reactor.Distillation end liquid enters Mono Chloro Acetic Acid distillation tower.Most of Mono Chloro Acetic Acid in mixed solution is distilled, separates by condensation and obtain liquid chlorine acetic acid product with vapor form from top of tower; Distillation end liquid is mainly heavy constituent.The shortcoming of this complete processing is: 1) by hydrolysis, Acetyl Chloride 98Min. is processed into acetic acid and HCL causes all recycle and reuse of Acetyl Chloride 98Min., system will constantly be supplemented aceticanhydride, guarantee the concentration of Acetyl Chloride 98Min. in chlorination reactor, thereby guarantee normally carrying out of reaction, cause aceticanhydride consumption higher; 2) the hydrolysis reaction water occurring in hydrolysis reactor is excessive, and water finally returns to chlorination reactor circulating reaction with acetic acid as light constituent, generates acetic acid, so will further cause the consumption of aceticanhydride because aceticanhydride preferentially reacts with water; 3) because hydrolysis reactor working pressure is higher, should not set up agitator, hydrolysis reaction is insufficient, and more unreacted Acetyl Chloride 98Min. enters hydrogenator and finally causes hydrogenation reaction by product to increase, and product yield is low; 4) can not process the HCL dissolving in chlorination mother solution, will affect hydrogenation reaction efficiency in hydrogenator, cause catalyzer consumption to increase.
Summary of the invention
The present invention aims to provide a kind of production of chloroacetic acid method, can reduce the usage quantity of aceticanhydride, and the growing amount that simultaneously reduces heavy constituent increases Mono Chloro Acetic Acid product yield.
For realizing above technical purpose, the present invention is by the following technical solutions: a kind of production of chloroacetic acid method that reduces aceticanhydride usage quantity, and aceticanhydride reacts the Acetyl Chloride 98Min. generating with HCL, and Acetyl Chloride 98Min. impels acetic acid and the chlorine generation Mono Chloro Acetic Acid that reacts as catalyzer, it is characterized in that, comprise the steps:
1) chlorine, acetic acid and aceticanhydride add chlorination reactor, and aceticanhydride and HCL first react, and generate Acetyl Chloride 98Min.; Under the effect of Acetyl Chloride 98Min. catalysis, there is chlorination reaction and generate Mono Chloro Acetic Acid, HCL and dichloro acetic acid and other materials in acetic acid and chlorine; HCL passes into acetic acid, aceticanhydride while driving first in advance, passes on a small quantity continuously chlorine, can generate HCL and Acetyl Chloride 98Min., just passes into continuously acetic acid, aceticanhydride, chlorine after concentration reaches requirement.
2) from chlorination reactor chlorination mother solution out, enter first distillation tower, acetic acid in chlorination mother solution and most of Acetyl Chloride 98Min. and HCL steam, by being back in chlorination reactor and recycling after condenser condenses, at the bottom of tower, mother liquor enters hydrogenator, under palladium-carbon catalyst effect, by hydrogenation, more than 90% dichloro acetic acid is reduced into Mono Chloro Acetic Acid; There is 2～5% Mono Chloro Acetic Acid to be hydrogenated simultaneously and be reduced to acetic acid; At the bottom of tower, in mother liquor, acetaldehyde is produced in remaining micro-Acetyl Chloride 98Min. and hydrogen generation side reaction, and acetaldehyde generates heavy constituent complex compound with other organism under hydrogen and palladium-carbon catalyst effect; It is the part composition in chlorination mother solution that other organism generates heavy constituent complex compound.
3) from the chlorination mother solution of hydrogenator process hydrogenation reaction out, enter second distillation tower, acetic acid distills with gas phase form, after condenser condenses, is back to recycle in chlorination reactor; At the bottom of tower, mother liquor is Mono Chloro Acetic Acid.
Further, the chlorine adding step 1) is liquid chlorine or chlorine.
Further, step 3) from mother liquor at the bottom of second distillation tower tower out, be that mother liquor continues to enter the 3rd distillation tower at the bottom of Mono Chloro Acetic Acid product or tower, by Mono Chloro Acetic Acid from top of tower with vapor form distillation, separate, by condensation, obtain liquid chlorine acetic acid product.
Chlorination mother solution refers to the reaction product that in chlorination reactor, reaction obtains after finishing, and comprises Mono Chloro Acetic Acid, HCL and dichloro acetic acid and other materials.
At the bottom of tower, mother liquor refers to acetic acid and most of Acetyl Chloride 98Min. and HCL in chlorination mother solution and steams rear remaining heavy constituent material, is mainly Mono Chloro Acetic Acid and dichloro acetic acid.
Advantage of the present invention is: the present invention has cancelled hydrolysis reactor, has increased by the first distillation tower, has played following effect:
(1) most Acetyl Chloride 98Min. is distilled out of and loops reaction, and after producing continuously, the add-on of aceticanhydride is few, is mainly used in balance acetic acid and liquid chlorine raw material is brought the moisture of system into.The present invention can drop to 0.01～0.03t/t left and right by 0.06～0.12t/t by Mono Chloro Acetic Acid product aceticanhydride ton consumption.
(2) most Acetyl Chloride 98Min. is distilled out of and loops reaction, so it is less that hydrogenation generates heavy constituent, second base product output object can be used as qualified Mono Chloro Acetic Acid product and sell, thereby Mono Chloro Acetic Acid product has been avoided becoming gaseous state from liquid state and has been become liquid process again, therefore the present invention can reduce by 30～50% by Mono Chloro Acetic Acid product steam ton consumption, and simultaneously chloroacetic yield increases by 1～2%.
(3) most HCL is distilled out of, and has reduced the content of HCL in chlorination mother solution, has improved hydrogenation reaction efficiency.
(4) the present invention still retains the 3rd distillation tower, when producing high-quality Mono Chloro Acetic Acid product (Mono Chloro Acetic Acid >=99.9%wt), can enable this tower, thereby guarantees the handiness of production operation.
Accompanying drawing explanation
Fig. 1 is process flow sheet of the present invention
Fig. 2 is former process flow sheet
1, chlorination reactor 2, first distillation tower 3, hydrogenator
4, second distillation tower 5, the 3rd distillation tower 6, pump
7, condenser 8, reboiler 9, hydrolysis reactor
Embodiment
Below by example, technology of the present invention is given to illustrate further.
Embodiment 1
1) chlorine, acetic acid and aceticanhydride add chlorination reactor, and aceticanhydride and HCL first react, and generate Acetyl Chloride 98Min.; Under the effect of Acetyl Chloride 98Min. catalysis, there is chlorination reaction and generate Mono Chloro Acetic Acid, HCL and dichloro acetic acid and other materials in acetic acid and chlorine;
2) from chlorination reactor chlorination mother solution out, enter first distillation tower, acetic acid in chlorination mother solution and most of Acetyl Chloride 98Min. and HCL steam, by being back in chlorination reactor and recycling after condenser condenses, at the bottom of tower, mother liquor enters hydrogenator, under palladium-carbon catalyst effect, by hydrogenation, more than 90% dichloro acetic acid is reduced into Mono Chloro Acetic Acid; There is 2～5% Mono Chloro Acetic Acid to be hydrogenated simultaneously and be reduced to acetic acid; At the bottom of tower, in mother liquor, acetaldehyde is produced in remaining micro-Acetyl Chloride 98Min. and hydrogen generation side reaction, and acetaldehyde generates heavy constituent complex compound with other organism under hydrogen and palladium-carbon catalyst effect;
3) from the chlorination mother solution of hydrogenator process hydrogenation reaction out, enter second distillation tower, acetic acid distills with gas phase form, after condenser condenses, is back to recycle in chlorination reactor; At the bottom of tower, mother liquor is Mono Chloro Acetic Acid.
Mono Chloro Acetic Acid product aceticanhydride ton consumption is 0.01～0.03t/t left and right.
Embodiment 2
1) liquid chlorine, acetic acid and aceticanhydride add chlorination reactor, and aceticanhydride and HCL first react, and generate Acetyl Chloride 98Min.; Under the effect of Acetyl Chloride 98Min. catalysis, there is chlorination reaction and generate Mono Chloro Acetic Acid, HCL and dichloro acetic acid and other materials in acetic acid and liquid chlorine;
2) from chlorination reactor chlorination mother solution out, enter first distillation tower, acetic acid in chlorination mother solution and most of Acetyl Chloride 98Min. and HCL steam, by being back in chlorination reactor and recycling after condenser condenses, at the bottom of tower, mother liquor enters hydrogenator, under palladium-carbon catalyst effect, by hydrogenation, more than 90% dichloro acetic acid is reduced into Mono Chloro Acetic Acid; There is 2～5% Mono Chloro Acetic Acid to be hydrogenated simultaneously and be reduced to acetic acid; At the bottom of tower, in mother liquor, acetaldehyde is produced in remaining micro-Acetyl Chloride 98Min. and hydrogen generation side reaction, and acetaldehyde generates heavy constituent complex compound with other organism under hydrogen and palladium-carbon catalyst effect;
3) from the chlorination mother solution of hydrogenator process hydrogenation reaction out, enter second distillation tower, acetic acid distills with gas phase form, after condenser condenses, is back to recycle in chlorination reactor; Step 3) from mother liquor at the bottom of second distillation tower tower out, continue to enter the 3rd distillation tower, Mono Chloro Acetic Acid is distilled, separated with vapor form from top of tower, by condensation, obtain liquid chlorine acetic acid product, Mono Chloro Acetic Acid >=99.9%wt), Mono Chloro Acetic Acid product aceticanhydride ton consumption 0.01～0.03t/t left and right.
Claims (3)
1. reduce a production of chloroacetic acid method for aceticanhydride usage quantity, aceticanhydride reacts the Acetyl Chloride 98Min. generating with HCL, and Acetyl Chloride 98Min. impels acetic acid and the chlorine generation Mono Chloro Acetic Acid that reacts as catalyzer, it is characterized in that, comprises the steps:
1) chlorine, acetic acid and aceticanhydride add chlorination reactor, and aceticanhydride and HCL first react, and generate Acetyl Chloride 98Min.; Under the effect of Acetyl Chloride 98Min. catalysis, there is chlorination reaction and generate Mono Chloro Acetic Acid, HCL and dichloro acetic acid and other materials in acetic acid and chlorine;
2) from chlorination reactor chlorination mother solution out, enter first distillation tower, acetic acid in chlorination mother solution and most of Acetyl Chloride 98Min. and HCL steam, by being back in chlorination reactor and recycling after condenser condenses, at the bottom of tower, mother liquor enters hydrogenator, under palladium-carbon catalyst effect, by hydrogenation, more than 90% dichloro acetic acid is reduced into Mono Chloro Acetic Acid; There is 2～5% Mono Chloro Acetic Acid to be hydrogenated simultaneously and be reduced to acetic acid; At the bottom of tower, in mother liquor, acetaldehyde is produced in remaining micro-Acetyl Chloride 98Min. and hydrogen generation side reaction, and acetaldehyde generates heavy constituent complex compound with other organism under hydrogen and palladium-carbon catalyst effect;
3) from the chlorination mother solution of hydrogenator process hydrogenation reaction out, enter second distillation tower, acetic acid distills with gas phase form, after condenser condenses, is back to recycle in chlorination reactor; At the bottom of tower, mother liquor is Mono Chloro Acetic Acid.
2. a kind of production of chloroacetic acid method that reduces aceticanhydride usage quantity according to claim 1, is characterized in that step 1) in the chlorine that adds be liquid chlorine or chlorine.
3. a kind of production of chloroacetic acid method that reduces aceticanhydride usage quantity according to claim 1, it is characterized in that, step 3) from mother liquor at the bottom of second distillation tower tower out, be that mother liquor continues to enter the 3rd distillation tower at the bottom of Mono Chloro Acetic Acid product or tower, Mono Chloro Acetic Acid is distilled, separated with vapor form from top of tower, by condensation, obtain liquid chlorine acetic acid product.
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104649887A (en) * | 2015-02-05 | 2015-05-27 | 中国天辰工程有限公司 | Production method of chloroacetic acid and method for recovering catalysts in production process of chloroacetic acid |
| CN105367410A (en) * | 2015-12-02 | 2016-03-02 | 中国天辰工程有限公司 | Hydrogenation refining system for producing chloroacetic acid |
| WO2017064015A1 (en) | 2015-10-13 | 2017-04-20 | Akzo Nobel Chemicals International B.V. | Process for the preparation of monochloroacetic acid |
| CN108484386A (en) * | 2018-06-28 | 2018-09-04 | 南通山剑石墨设备有限公司 | Continuous production device for chloroacetic acid and its production technology |
| CN108602746A (en) * | 2016-02-04 | 2018-09-28 | Pcc慕卡有限公司 | The method of industrial production chloroacetic acid |
| CN109851490A (en) * | 2019-03-01 | 2019-06-07 | 湖北泰盛化工有限公司 | The chloroacetic technique of acetic anhydride catalyst method continuous production |
| WO2019241998A1 (en) * | 2018-06-22 | 2019-12-26 | 南通山剑石墨设备有限公司 | Chloroacetic acid purification processing device |
| WO2019241997A1 (en) * | 2018-06-22 | 2019-12-26 | 南通山剑石墨设备有限公司 | Chloroacetic acid continuous production device and production process therefor |
| CN112250559A (en) * | 2020-10-28 | 2021-01-22 | 刘光辉 | Process for recycling chloro pivaloyl chloride residual liquid |
| CN112409164A (en) * | 2021-01-19 | 2021-02-26 | 潍坊滨海石油化工有限公司 | Treatment method of mother liquor produced by chloroacetic acid preparation through hydrogenation method |
| CN112592285A (en) * | 2021-01-13 | 2021-04-02 | 河南红东方化工股份有限公司 | Continuous ammoniation production method of aminoacetic acid |
| CN112592266A (en) * | 2021-01-13 | 2021-04-02 | 河南红东方化工股份有限公司 | Continuous production process of chloroacetic acid |
| CN115215741A (en) * | 2021-04-21 | 2022-10-21 | 湖北泰盛化工有限公司 | Quick crystallization and purification process for chloroacetic acid |
| CN115245792A (en) * | 2022-09-22 | 2022-10-28 | 山东民基新材料科技有限公司 | Chloroacetic acid synthesis system and synthesis method |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104649887A (en) * | 2015-02-05 | 2015-05-27 | 中国天辰工程有限公司 | Production method of chloroacetic acid and method for recovering catalysts in production process of chloroacetic acid |
| WO2017064015A1 (en) | 2015-10-13 | 2017-04-20 | Akzo Nobel Chemicals International B.V. | Process for the preparation of monochloroacetic acid |
| CN105367410A (en) * | 2015-12-02 | 2016-03-02 | 中国天辰工程有限公司 | Hydrogenation refining system for producing chloroacetic acid |
| CN108602746B (en) * | 2016-02-04 | 2022-02-22 | Pcc Mcaa 有限公司 | Method for industrial production of monochloroacetic acid |
| CN108602746A (en) * | 2016-02-04 | 2018-09-28 | Pcc慕卡有限公司 | The method of industrial production chloroacetic acid |
| WO2019241998A1 (en) * | 2018-06-22 | 2019-12-26 | 南通山剑石墨设备有限公司 | Chloroacetic acid purification processing device |
| WO2019241997A1 (en) * | 2018-06-22 | 2019-12-26 | 南通山剑石墨设备有限公司 | Chloroacetic acid continuous production device and production process therefor |
| CN108484386A (en) * | 2018-06-28 | 2018-09-04 | 南通山剑石墨设备有限公司 | Continuous production device for chloroacetic acid and its production technology |
| CN109851490A (en) * | 2019-03-01 | 2019-06-07 | 湖北泰盛化工有限公司 | The chloroacetic technique of acetic anhydride catalyst method continuous production |
| CN112250559A (en) * | 2020-10-28 | 2021-01-22 | 刘光辉 | Process for recycling chloro pivaloyl chloride residual liquid |
| CN112250559B (en) * | 2020-10-28 | 2024-05-03 | 王泽萱 | Recycling process of chloro pivaloyl chloride raffinate |
| CN112592285A (en) * | 2021-01-13 | 2021-04-02 | 河南红东方化工股份有限公司 | Continuous ammoniation production method of aminoacetic acid |
| CN112592266A (en) * | 2021-01-13 | 2021-04-02 | 河南红东方化工股份有限公司 | Continuous production process of chloroacetic acid |
| CN112409164A (en) * | 2021-01-19 | 2021-02-26 | 潍坊滨海石油化工有限公司 | Treatment method of mother liquor produced by chloroacetic acid preparation through hydrogenation method |
| CN115215741A (en) * | 2021-04-21 | 2022-10-21 | 湖北泰盛化工有限公司 | Quick crystallization and purification process for chloroacetic acid |
| CN115245792A (en) * | 2022-09-22 | 2022-10-28 | 山东民基新材料科技有限公司 | Chloroacetic acid synthesis system and synthesis method |
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Application publication date: 20140924 |