Process for the production of chlorinated propanes

Patent metadata

Field	Value
Publication number	US-2016002127-A1
Application number	US-201414771215-A
Country	US
Kind code	A1
Filing date	Feb 28, 2014
Priority date	Feb 28, 2013
Publication date	Jan 7, 2016
Grant date	—

Abstract

Processes for the production of chlorinated propanes are provided. The processes comprise catalyzing the chlorination of 1,1,1,3-tetrachloropropane with aluminum chloride, either alone or in combination with ferric chloride. Low intensity conditions are appropriate for the process, e.g., temperatures of from ambient to 100° C. and pressures of from ambient to 200 psig may be used. Even though low intensity conditions are used, the aluminum chloride provides at least 1.5 times greater the conversion rate and/or productivity of 1,1,1,3-tetrachloropropane as compared to ferric chloride when used as a single catalyst under similar processing conditions.

First claim

1 . A process for the production of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane comprising catalyzing the chlorination of 1,1,1,3-tetrachloropropane with aluminum chloride, either alone or in combination with ferric chloride.

2 . The process of claim 1 , wherein aluminum chloride is used alone.

3 . The process of claim for 1 , wherein the process is carried out in the presence of a solvent.

4 . The process of claim 3 , wherein the solvent comprises carbon tetrachloride, sulfuryl chloride, one or more tetrachloropropanes, one or more pentachloropropanes, one or more hexachloropropanes, or a combination of any number of these.

5 . The process of claim 1 , wherein the process is carried out at a temperature of from ambient to 100° C.

6 . The process of claim 1 , carried out at a pressure of from ambient to 200 psig.

7 . The process of claim 1 , wherein at least a 80% conversion of the 1,1,1,3-tetrachloropropane is provided with productivity of greater than 360 gr/L/min.

8 . The process of claim 1 , wherein a yield of 1,1,1,2,3-pentachloropropane of at least 75% with productivity of greater than 360 gr/L/min.

9 . The process of claim 1 , wherein the 1,1,1,3-tetrachloropropane is prepared in situ.

10 . The process of claim 9 , wherein the 1,1,1,3-tetrachloropropane is prepared by the reaction of ethylene and carbon tetrachloride in the presence of one or more Lewis acid catalysts and optionally, a trialkylphosphate or alkylamine.

11 . The process of claim 10 , wherein the Lewis acid comprises ferric chloride, couprous chloride, aluminum chloride, titanium chloride, antimony pentachloride, boron trichloride, one or more lanthanum halides, one or more metal triflates, or a combination of these.

12 . The process of claim 1 , wherein the product stream comprising 1,1,1,2,3-pentachloropropane is dehydrochlorinated to produce 1,1,2,3-tetrachloropropene.

13 . The process of claim 12 , wherein the dehydrochlorination is conducted using caustic.

14 . The process of claim 12 , wherein the dehydrochlorination is conducted catalytically using a Lewis acid catalyst.

15 . The process of claim 14 , wherein the Lewis acid catalyst comprises ferric chloride, aluminum chloride, titanium chloride, antimony pentachloride, boron trichloride, one or more lanthanum halides, one or more metal triflates, or a combination of these.

Assignees

• Blue Cube Ip Llc

Inventors

• Tirtowidjojo Max M
• Laitar David S

Classifications

• C07C17/25

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title

• C07C17/10 Primary

  of hydrogen atoms (combined with addition of halogens to unsaturated hydrocarbons C07C17/06) · CPC title

• C07C17/275

  of hydrocarbons and halogenated hydrocarbons · CPC title