Process for the production of 4-chloroacetoacetyl chloride, 4-chloroacetoacetic acid esters, amides and imides

Patent metadata

Field	Value
Publication number	US-9227905-B2
Application number	US-201214112468-A
Country	US
Kind code	B2
Filing date	Apr 25, 2012
Priority date	Apr 29, 2011
Publication date	Jan 5, 2016
Grant date	Jan 5, 2016

Abstract

The invention relates to process for the continuous production of 4-chloroacetoacetyl chloride, comprising the steps of (a) feeding diketene and chlorine into a thin film reactor and (b) reacting the diketene and chlorine to obtain 4-chloroacetoacetyl chloride. The invention also relates to a process for the production of 4-chloroacetoaceticacid ester, 4-chloroacetoaceticacid amide or 4-chloroacetoaceticacid imide from 4-chloroacetoacetyl chloride obtained according to the inventive process.

First claim

The invention claimed is:

1. A process for the production of 4-chloroacetoacetyl chloride, comprising the steps of
(a) feeding diketene and chlorine into a wiped film reactor and
(b) reacting the diketene and chlorine to obtain 4-chloroacetoacetyl chloride,

wherein in step (a) the diketene is fed into the reactor in the form of a mixture with an organic solvent, wherein the concentration of the diketene in the mixture is higher than 15% (w/w),
wherein in step (a) the chlorine is fed into the reactor in the form of gaseous chlorine, wherein the chlorine is not diluted with an inert gas, and wherein the process is a continuous process, wherein the diketene is fed into the reactor at a rate of at least 10 kg/h.

2. The process of claim 1 , wherein the solvent is a halogenated alkane.

3. The process of claim 1 , wherein the diketene is fed into the reactor at a rate of at least 75 kg/h.

4. The process of claim 1 , wherein the reaction temperature is between −15° C. and 60° C.

5. The process of claim 1 , wherein the solvent is recycled and reused in the process.

6. The process of claim 1 , wherein the solvent has a purity of at least 98 weight %.

7. A process for the production of a 4-chloroacetoaceticacid ester, a 4-chloroacetoaceticacid amide or a 4-chloroacetoaceticacid imide, comprising the steps
(c) producing 4-chloroacetoacetyl chloride according to a process of any of the preceding claims, transferring it into a second reactor, and
(d) reacting the 4-chloroacetoacetyl chloride with an alcohol or amine to obtain the 4-chloroacetoaceticacid ester, 4-chloroacetoaceticacid amide or a 4-chloroacetoaceticacid imide.

8. The process of claim 7 , wherein the alcohol is an alkanol.

9. The process of claim 7 , wherein the reaction temperature in step (d) is between 0° C. and 80° C.

10. The process of claim 8 , wherein the reaction temperature in step (d) is between 0° C. and 80° C.

11. The process of claim 7 , wherein the yield of the 4-chloroacetoaceticacid ester, 4-chloroacetoaceticacid amide or 4-chloroacetoaceticacid imide is at least 90%, based on the total amount of ketene provided in step (a).

12. The process of claim 8 , wherein the yield of the 4-chloroacetoaceticacid ester, 4-chloroacetoaceticacid amide or 4-chloroacetoaceticacid imide is at least 90%, based on the total amount of ketene provided in step (a).

13. The process of claim 2 wherein said halogenated alkane is selected from chloromethane, dichloromethane, trichloromethane (chloroform), tetrachloromethane, chloroethane, 1,2-dichlorethane, trichloroethane, tetrachloroethane, dichloropropane, 1-chloro-2-fluoroethane, 1,1-dichloroethane, 1,2-dichloroethane, methylchloroform, 1-chlorobutane, 2-chlorobutane, 1-bromobutane, ethyl bromide, 1-bromo-2-chloroethane, 1-bromo-2-fluoroethane, 1-iodobutane, bromochloromethane, dibromomethane, 1,1-dibromomethane, difluoroiodomethane, 1-bromopropane, bromochlorofluoromethane, 2-bromopropane, bromodichloromethane, bromofluoromethane, bromotrichloromethane, dibromodifluoromethane, pentachloromethane, 1,1,1,2-tetrachloroethane, fluoroiodomethane, iodomethane, diiodofluoromethane, 1,1,2,2-tetrachloromethane, 1,1,2-trichloroethane, 1-chloropropane, 1,2-dibromopropane, 1,2,3-trichloropropane, 1,1,1,2-tetrachloropropane and mixtures thereof or mixtures comprising at least one thereof.

14. The process of claim 8 , wherein said alkanol is selected from the group of methanol, ethanol, isopropanol, tert-butanol or phenol.

Assignees

• Klegraf Ellen
• Caraucan Davila Miguel Angel
• Lonza Ag

Inventors

• Klegraf Ellen
• Caraucan Davila Miguel Angel

Classifications

• C07C59/21

  containing halogen · CPC title

• C07C69/716

  Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} · CPC title

• C07C51/58 Primary

  Preparation of carboxylic acid halides · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title

• C07C235/88

  having the nitrogen atom of at least one of the carboxamide groups further acylated · CPC title