CA1143383A - Production of chloroacetyl chloride - Google Patents
Production of chloroacetyl chlorideInfo
- Publication number
- CA1143383A CA1143383A CA000355597A CA355597A CA1143383A CA 1143383 A CA1143383 A CA 1143383A CA 000355597 A CA000355597 A CA 000355597A CA 355597 A CA355597 A CA 355597A CA 1143383 A CA1143383 A CA 1143383A
- Authority
- CA
- Canada
- Prior art keywords
- chloride
- acetyl chloride
- acid
- chloroacetyl
- monochloroacetic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
PRODUCTION OF CHLOROACETYL CHLORIDE
ABSTRACT OF THE DISCLOSURE:
The invention relates to a process for making chloroacetyl chloride by subjecting acetyl chloride to a chlorination reaction. To this end, the in-vention provides for acetyl chloride in vapor form to be reacted with liquefied monochloroacetic acid in the presence of a stream of hydrogen chloride in a reaction zone heated to 110 to 180° C with the resultant formation of chloroacetyl chloride, the acetyl chloride and monochloroacetic acid being used in stoechiometric proportions or the mono-chloroacetic acid being used in a molar excess.
Next, the reaction mixture is treated so as to expel a mixture formed of chloroacetyl chloride and unreacted acetyl chloride and the acid chloride mixture is subjected to distillative treatment so as to separate chloroacetyl chloride therefrom.
ABSTRACT OF THE DISCLOSURE:
The invention relates to a process for making chloroacetyl chloride by subjecting acetyl chloride to a chlorination reaction. To this end, the in-vention provides for acetyl chloride in vapor form to be reacted with liquefied monochloroacetic acid in the presence of a stream of hydrogen chloride in a reaction zone heated to 110 to 180° C with the resultant formation of chloroacetyl chloride, the acetyl chloride and monochloroacetic acid being used in stoechiometric proportions or the mono-chloroacetic acid being used in a molar excess.
Next, the reaction mixture is treated so as to expel a mixture formed of chloroacetyl chloride and unreacted acetyl chloride and the acid chloride mixture is subjected to distillative treatment so as to separate chloroacetyl chloride therefrom.
Description
~33~33 The present invention relates to a process for making chloroacetyl chloride free from higher chlorinated by-products, with the use of acetyl chloride as feed material.
Acetyl chloride is a by-product often obtained in industry, for example in the process wherein acetic acid is chlorinated in the presence of acetic anhydride with the resultant formation of monochloroacetic acid or in the process for making 2,5-dioxo-1-oxa-phospholane de-scribed in Genman Patent 2 531 238. It is also possible for pure acetyl chloride to be made from acetic an-hydride and hydrogen chloride.
The conversion of commercially not very attractive acetyl chloride to more attractive chloroacetyl chloride is beset with considerable dlfficulties. These are baslcally a result of the processes described hereto-fore for the production of chloroacetyl chloride, wherein acetyl chloride is subjected to a chlorination reaction with formation of by-products, especially dichloroacetyl chloride, which cannot, by distillation or other treatment, be removed from chloroacetyl chloride.
It has been deqcribed in the literature that by the use of suitable catalysts, it is possible to reduce, but impossible to avoid, by-product formation. The process :
described ln German Patent Specification "Offenlegungs-schrift" 2 263 580, for example, provides for acetyl
Acetyl chloride is a by-product often obtained in industry, for example in the process wherein acetic acid is chlorinated in the presence of acetic anhydride with the resultant formation of monochloroacetic acid or in the process for making 2,5-dioxo-1-oxa-phospholane de-scribed in Genman Patent 2 531 238. It is also possible for pure acetyl chloride to be made from acetic an-hydride and hydrogen chloride.
The conversion of commercially not very attractive acetyl chloride to more attractive chloroacetyl chloride is beset with considerable dlfficulties. These are baslcally a result of the processes described hereto-fore for the production of chloroacetyl chloride, wherein acetyl chloride is subjected to a chlorination reaction with formation of by-products, especially dichloroacetyl chloride, which cannot, by distillation or other treatment, be removed from chloroacetyl chloride.
It has been deqcribed in the literature that by the use of suitable catalysts, it is possible to reduce, but impossible to avoid, by-product formation. The process :
described ln German Patent Specification "Offenlegungs-schrift" 2 263 580, for example, provides for acetyl
- 2 -,j ",, ,,~ .^,~~~
3~83 chloride to be chlorinated with chlorine in the presence of concentrated sulfuric acid as a catalyst, whilst the process described in German Patent Specification "Offenlegungcschrift" 2 729 911 provides for chloro-sulfonic acid to be used as the catalyst. These arssteps which indeed permit the dichloroacetyl chloride content, based on chloroacetyl chloride, to be reduced from 1.5 to 0.5 weight%, but the catalyst i9 very di~ficult to separate. While this has been fully dis-closed in German Patent Specification "Offenlegungs-schrift" 2 729 911, the fact remains that the proces~
described therein is al~o not fully sati~factory from a technical point of view. This process actually permits the diacetyl chloride content to be reduced as compared with prior art methods. On the other hand, however, it entail~ the ~ormation of higher-boiling by-products and catalyst separation continues to remain a dif~icult procedure.
The present invention now provides a process for making chloroacetyl chloride which permits the difficulties encountered heretofore in the production of this compound to be completely avoided, wherein acetyl chloride i3 reacted with monochloroacetic acid ln accordance with the following equation:
H3C-COCl + ClCH2-COOH ~ CiCH2-COCl + CH3-COOH
In order to avoid the formation of acetic anhydride during the above reaction, it is an important requirement for the latter to be carried out in the presence of hydrogen chloride. The reaction as illustrated by the above equation is based on an equilibrium position which is soon established at ele~ated temperature and which ex-periments have shown to lie at about 65 mol% acetyl chloride and 35 mol~ chloroacetyl chloride. It is possible for the equilibrium position to be acted upon in favor of chloroacetyl chloride formation. To this end, it is necessary always to provide for the presence of an excess of monochloroacetic acid, with respect to acetyl chloride, in the reaction mixture. Use can, for example, be made of a reactor provided with suitable accessory equipment, for continuous operation~
The present invention relates more particularly to a process for making chloroacetyl chloride by subJecting acetyl chloride to a chlorination reaction, which comprises:
reacting acetyl chloride in vapor form with liquefied monochloroacetic acid in the presence of a ~tream of hydrogen chloride in a reaction zone heated to 110 to 180 C with the resultant formation of chloroacetyl chloride, the acetyl chloride and monochloroacetic acid being used in stoechiometric proportions or the mono-chloroacetic acid being used in a molar excess; expell1ng, from the reaction mixture, a mixture formed of chloroacetyl chloride and unreacted acetyl chloride and subjecting the acid chloride mixture to distillative treatment so as to separate chloroacetyl chloride there~rom.
It is pre~erable in accordance with this invention to use acetyl chloride and monochloroacetic acid in a ~I .
~33~3 molar ratio w~thin the range 1 : 1 - 25. In the ~ent of the present process being carried out conti~uously, which is preferred, it is possible, by the installation of accessory equipment inside the reactor, to provide 5 for a mulffple molar excess of monochloroacetic acid in the reaction zone. In the e~nt of the process being carried out discontinuously, the feed materials should preferably be used in a molar ratio of 1 : 10 - 15.
The liquefied monochloroacetic acid which is in-10 troduced into the reaction zone generally ha~ a temperature of about 70 to 120 C, the reaction zone itself being pre-ferably maintained at a temperature of 120 to 130 C.
; A further preferred feature of the present process provides for acetyl chloride and monochloroacetic acid 15 to be reacted with one another in countercurrent fashion inside the reaction zone, the acetyl chloride flowing upwardly, and the monochloroacetic acid flowing downwardly, through the reaction zone. It is also preferable for the ace~a chloride in vapor form to be admitted together with 20 hydrogen chloride to the reaction zone, 0.5 to 3 mols of , hydrogen chloride being used per mol of acetyl chloride.
The prooess of the present invention can more - particularly be carried out in a tubular reactor placed in uprlght position, heated to 110 to 180 C and provided 25 with accessory equipment, e. g. in a bubble tray column.
Introduced thereinto from above is liquid monochloro-acetic acid of 100 C and continuously introduced thereinto from~below is acetyl chloride in vapor form ~" .
i ` ~l q ~3~3~3 together with a constant stream of hydrogen chloride, which is intended to avoid the formation o~ acid an-hydrides, the acetyl chloride being contacted on each of the individual trays with an excess of monochloroacetic acid. The moncchloroacetic acid and zcetyl chloride are customarily used in a molar ratio of at least 1 : 1.
It i9 also possible, however, to use a multiple excess of monochloroacetic acid.
Mounted onto the head of the reactor is a distilling column. Directly separated therein, from a higher-boiling acid mixture, is an acid chloride mixture consisting of chloroacetyl chloride and unreacted acetyl chloride, which is continuously removed. Next, the acld-free acid chloride mixture is distllled and pure chloroacetyl chloride is recovered without difficulty, resulting acetyl chloride being recycled to the reactor.
The purity of the chloroacetyl chloride so made partially depends on the purity of the monochloroacetic acid ~eed material. Despite this, it has been found that even in those cases in which use is made of commercial monochloroacetic acid containing about 0.4 to 0.6 weight%
of dichloroacetic acid, the resulting chloroacetyl chlorlde i~ unexpectedly free from dichloroacetyl chloride. Acid mixture which is obtained in the base portion of the reactor can be used for the production of monochloro-acetic acid.
Technically highly beneficial effects of the present process reside in the fact that chloro-acetyl chloride ~I
:
, .
~33133 as the reaction product is obtained in the absence of wldesirable by-products and with little expenditure of machinery.
The following Examples illustrate the invention which is naturally not limited thereto.
EXAMPLE 1:
189 g/h (2mols) o~ monochloroacetic acid which had a temperature of 100 C and contained 0.55 weight% of dichloroacetic acid was introduced into the upper portion of a bubble tray column heated to 120~ C. Introduced at the same time into the lower portion of the column was 78.5 g/h (1 mol) of acetyl chloride in vapor form to-gether with 30 - 40 l/h of hydrogen chloride gas which was intended to avoid the formation of acid anhydrides.
Mounted onto the head of the bubble tray column was a short column i~rom which a mixture of acetyl chloride and chloro-acetyl chloride was removed at a reflux ratio of about 1 :1.
Hydrogen chloride gas which also escaped overhead was de-livered to a cooling trap, in which acetyl chloride carried over was condensed. 39S g of a mixture which contained ~0 wgt%
, or 118.5 g of chloroacetyl chloride and 70 weight% or 276.S g of acetyl chloride was taken from the column and cooling trap, within 5 hours~ Chloracetyl chloride was obtained in a yield of 70.9 %, based on the acetyl chloride which underwent conversion, the chloroacetyl chloride con-taining less than 0.1 weight% of dichloroacetyl chloride.
The acid chloride mixture was sub~ected to distillation and recovered pure acetyl chloride was recycled to the reactor. A mi~ture of monochloroacetic acid and acetic ~ 3 acid obtained in the base portion of the reactor wa~
used ~or making monochloroacetic acid.
EXAMPLE 2:
The procedure was as in Example 1, but 157 g~h (2 mols) of acetyl chloride was used. 809 g of a mixture containing 12 weight% or 97 g of chloroacetyl chloride and 88 weight%
or 712 e Of ace~a chloride was taken from the column and cooling trap, within 5 hours.
Chloroacetyl chloride was obtained in a yield of 83.5 %, based on the acetyl chloride which underwent reaction, the chloroacetyl chloride containing less than 0.1 w~ight% of dichloroaotyl chloride.
EXAMPLE 3:
The procedure was as in Example 1, but 94.5 g/h (1 mol) of monochloroacetic acid and 78.5 g/h (1 mol) of acetyl chloride were used. 571.1 g of a mixture which contained 12.2 weight% of chloroacetyl chloride and 87.7 w~ght% o~ acetyl chloride was taken from the column and cooling trap, within 7 hours.
Chloroacetyl chloride was obtained in a yield of 100 %, based on the acetyl chloride which underwent reaction, the chloroacetyl chloride containing less than 0.1 weight% of dichloroacetyl chloride.
/1 .
described therein is al~o not fully sati~factory from a technical point of view. This process actually permits the diacetyl chloride content to be reduced as compared with prior art methods. On the other hand, however, it entail~ the ~ormation of higher-boiling by-products and catalyst separation continues to remain a dif~icult procedure.
The present invention now provides a process for making chloroacetyl chloride which permits the difficulties encountered heretofore in the production of this compound to be completely avoided, wherein acetyl chloride i3 reacted with monochloroacetic acid ln accordance with the following equation:
H3C-COCl + ClCH2-COOH ~ CiCH2-COCl + CH3-COOH
In order to avoid the formation of acetic anhydride during the above reaction, it is an important requirement for the latter to be carried out in the presence of hydrogen chloride. The reaction as illustrated by the above equation is based on an equilibrium position which is soon established at ele~ated temperature and which ex-periments have shown to lie at about 65 mol% acetyl chloride and 35 mol~ chloroacetyl chloride. It is possible for the equilibrium position to be acted upon in favor of chloroacetyl chloride formation. To this end, it is necessary always to provide for the presence of an excess of monochloroacetic acid, with respect to acetyl chloride, in the reaction mixture. Use can, for example, be made of a reactor provided with suitable accessory equipment, for continuous operation~
The present invention relates more particularly to a process for making chloroacetyl chloride by subJecting acetyl chloride to a chlorination reaction, which comprises:
reacting acetyl chloride in vapor form with liquefied monochloroacetic acid in the presence of a ~tream of hydrogen chloride in a reaction zone heated to 110 to 180 C with the resultant formation of chloroacetyl chloride, the acetyl chloride and monochloroacetic acid being used in stoechiometric proportions or the mono-chloroacetic acid being used in a molar excess; expell1ng, from the reaction mixture, a mixture formed of chloroacetyl chloride and unreacted acetyl chloride and subjecting the acid chloride mixture to distillative treatment so as to separate chloroacetyl chloride there~rom.
It is pre~erable in accordance with this invention to use acetyl chloride and monochloroacetic acid in a ~I .
~33~3 molar ratio w~thin the range 1 : 1 - 25. In the ~ent of the present process being carried out conti~uously, which is preferred, it is possible, by the installation of accessory equipment inside the reactor, to provide 5 for a mulffple molar excess of monochloroacetic acid in the reaction zone. In the e~nt of the process being carried out discontinuously, the feed materials should preferably be used in a molar ratio of 1 : 10 - 15.
The liquefied monochloroacetic acid which is in-10 troduced into the reaction zone generally ha~ a temperature of about 70 to 120 C, the reaction zone itself being pre-ferably maintained at a temperature of 120 to 130 C.
; A further preferred feature of the present process provides for acetyl chloride and monochloroacetic acid 15 to be reacted with one another in countercurrent fashion inside the reaction zone, the acetyl chloride flowing upwardly, and the monochloroacetic acid flowing downwardly, through the reaction zone. It is also preferable for the ace~a chloride in vapor form to be admitted together with 20 hydrogen chloride to the reaction zone, 0.5 to 3 mols of , hydrogen chloride being used per mol of acetyl chloride.
The prooess of the present invention can more - particularly be carried out in a tubular reactor placed in uprlght position, heated to 110 to 180 C and provided 25 with accessory equipment, e. g. in a bubble tray column.
Introduced thereinto from above is liquid monochloro-acetic acid of 100 C and continuously introduced thereinto from~below is acetyl chloride in vapor form ~" .
i ` ~l q ~3~3~3 together with a constant stream of hydrogen chloride, which is intended to avoid the formation o~ acid an-hydrides, the acetyl chloride being contacted on each of the individual trays with an excess of monochloroacetic acid. The moncchloroacetic acid and zcetyl chloride are customarily used in a molar ratio of at least 1 : 1.
It i9 also possible, however, to use a multiple excess of monochloroacetic acid.
Mounted onto the head of the reactor is a distilling column. Directly separated therein, from a higher-boiling acid mixture, is an acid chloride mixture consisting of chloroacetyl chloride and unreacted acetyl chloride, which is continuously removed. Next, the acld-free acid chloride mixture is distllled and pure chloroacetyl chloride is recovered without difficulty, resulting acetyl chloride being recycled to the reactor.
The purity of the chloroacetyl chloride so made partially depends on the purity of the monochloroacetic acid ~eed material. Despite this, it has been found that even in those cases in which use is made of commercial monochloroacetic acid containing about 0.4 to 0.6 weight%
of dichloroacetic acid, the resulting chloroacetyl chlorlde i~ unexpectedly free from dichloroacetyl chloride. Acid mixture which is obtained in the base portion of the reactor can be used for the production of monochloro-acetic acid.
Technically highly beneficial effects of the present process reside in the fact that chloro-acetyl chloride ~I
:
, .
~33133 as the reaction product is obtained in the absence of wldesirable by-products and with little expenditure of machinery.
The following Examples illustrate the invention which is naturally not limited thereto.
EXAMPLE 1:
189 g/h (2mols) o~ monochloroacetic acid which had a temperature of 100 C and contained 0.55 weight% of dichloroacetic acid was introduced into the upper portion of a bubble tray column heated to 120~ C. Introduced at the same time into the lower portion of the column was 78.5 g/h (1 mol) of acetyl chloride in vapor form to-gether with 30 - 40 l/h of hydrogen chloride gas which was intended to avoid the formation of acid anhydrides.
Mounted onto the head of the bubble tray column was a short column i~rom which a mixture of acetyl chloride and chloro-acetyl chloride was removed at a reflux ratio of about 1 :1.
Hydrogen chloride gas which also escaped overhead was de-livered to a cooling trap, in which acetyl chloride carried over was condensed. 39S g of a mixture which contained ~0 wgt%
, or 118.5 g of chloroacetyl chloride and 70 weight% or 276.S g of acetyl chloride was taken from the column and cooling trap, within 5 hours~ Chloracetyl chloride was obtained in a yield of 70.9 %, based on the acetyl chloride which underwent conversion, the chloroacetyl chloride con-taining less than 0.1 weight% of dichloroacetyl chloride.
The acid chloride mixture was sub~ected to distillation and recovered pure acetyl chloride was recycled to the reactor. A mi~ture of monochloroacetic acid and acetic ~ 3 acid obtained in the base portion of the reactor wa~
used ~or making monochloroacetic acid.
EXAMPLE 2:
The procedure was as in Example 1, but 157 g~h (2 mols) of acetyl chloride was used. 809 g of a mixture containing 12 weight% or 97 g of chloroacetyl chloride and 88 weight%
or 712 e Of ace~a chloride was taken from the column and cooling trap, within 5 hours.
Chloroacetyl chloride was obtained in a yield of 83.5 %, based on the acetyl chloride which underwent reaction, the chloroacetyl chloride containing less than 0.1 w~ight% of dichloroaotyl chloride.
EXAMPLE 3:
The procedure was as in Example 1, but 94.5 g/h (1 mol) of monochloroacetic acid and 78.5 g/h (1 mol) of acetyl chloride were used. 571.1 g of a mixture which contained 12.2 weight% of chloroacetyl chloride and 87.7 w~ght% o~ acetyl chloride was taken from the column and cooling trap, within 7 hours.
Chloroacetyl chloride was obtained in a yield of 100 %, based on the acetyl chloride which underwent reaction, the chloroacetyl chloride containing less than 0.1 weight% of dichloroacetyl chloride.
/1 .
Claims (7)
THE CLAIMS:
1) A process for making chloroacetyl chloride by sub-jecting acetyl chloride to a chlorination raction, which comprises: reacting acetyl chloride in vapor form with liquefied monochloroacetic acid in the presence of a stream of hydrogen chloride in a reaction zone heated to 110 to 180° C with the resultant formation of chloroacetyl chloride, the acetyl chloride and monochloroacetic acid being used in stoechiometric proportions or the mono-chloroacetic acid being used in a molar excess;
expelling, from the reaction mixture, a mixture formed of chloroacetyl chloride and unreacted acetyl chloride and subjecting said acid chloride mixture to distillative treatment so as to separate chloroacetyl chloride therefrom.
expelling, from the reaction mixture, a mixture formed of chloroacetyl chloride and unreacted acetyl chloride and subjecting said acid chloride mixture to distillative treatment so as to separate chloroacetyl chloride therefrom.
2) A process as claimed in claim 1, wherein the liquefied monochloroacetic acid is used at a temperature of about 70 to 120° C.
3) A process as claimed in claim 1, wherein the acetyl chloride and monochloroacetic acid are used in a molar ratio of 1 : 1 - 25.
4) A process as claimed in claim 1, wherein the reaction zone is heated to a temperature of 120 to 130° C.
5) A process as claimed in claim 1, wherein 0.5 to 3 mols of hydrogen chloride is used per mol of acetyl chloride.
6) A process as claimed in claim 1, wherein the acetyl chloride and monochloroacetic acid are reacted with one another in countercurrent fashion inside the heated reaction zone, the acetyl chloride flowing upwardly, and the monochloroacetic acid flowing downwardly, through the reaction zone.
7) A process as claimed in claim 1, wherein the hydrogen chloride is admitted together with the acetyl chloride in vapor form to the reaction zone.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2927353.8 | 1979-07-06 | ||
| DE19792927353 DE2927353A1 (en) | 1979-07-06 | 1979-07-06 | METHOD FOR PRODUCING CHLORACETYL CHLORIDE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1143383A true CA1143383A (en) | 1983-03-22 |
Family
ID=6075082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000355597A Expired CA1143383A (en) | 1979-07-06 | 1980-07-07 | Production of chloroacetyl chloride |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0022185B1 (en) |
| JP (1) | JPS5610133A (en) |
| BR (1) | BR8004173A (en) |
| CA (1) | CA1143383A (en) |
| DE (2) | DE2927353A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037137A (en) * | 2015-08-27 | 2015-11-11 | 广西田东新特化工有限公司 | Method for producing chloroacetic acid |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104058947A (en) * | 2014-06-06 | 2014-09-24 | 中国天辰工程有限公司 | Chloroacetic acid production method capable of reducing acetic anhydride consumption |
| CN113979858A (en) * | 2021-10-15 | 2022-01-28 | 河北中化滏鼎化工科技有限公司 | Method for preparing chloroisobutyryl chloride by continuous chlorination |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1804436A1 (en) * | 1968-10-22 | 1970-05-21 | Knapsack Ag | Process for the production of monochloroacetyl chloride |
| DE2263580C2 (en) * | 1972-12-27 | 1982-06-03 | Basf Ag, 6700 Ludwigshafen | Process for the production of chloroacetyl chloride |
-
1979
- 1979-07-06 DE DE19792927353 patent/DE2927353A1/en not_active Withdrawn
-
1980
- 1980-06-12 EP EP80103270A patent/EP0022185B1/en not_active Expired
- 1980-06-12 DE DE8080103270T patent/DE3061418D1/en not_active Expired
- 1980-07-04 BR BR8004173A patent/BR8004173A/en unknown
- 1980-07-07 CA CA000355597A patent/CA1143383A/en not_active Expired
- 1980-07-07 JP JP9181580A patent/JPS5610133A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037137A (en) * | 2015-08-27 | 2015-11-11 | 广西田东新特化工有限公司 | Method for producing chloroacetic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0022185A1 (en) | 1981-01-14 |
| BR8004173A (en) | 1981-01-21 |
| JPS6316371B2 (en) | 1988-04-08 |
| EP0022185B1 (en) | 1982-12-22 |
| JPS5610133A (en) | 1981-02-02 |
| DE3061418D1 (en) | 1983-01-27 |
| DE2927353A1 (en) | 1981-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |