IP Library Granted Patent US 8,586,804
Granted Patent B2
US 8,586,804 · App. 13/278,511 · Granted Nov 19, 2013

Synthesis of 1,1,3-trichloro-1-propene

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Quick Facts
Patent No.
US 8,586,804
App. No.
13/278,511
Granted
Nov 19, 2013
Kind
B2
Abstract

Disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising contacting 1,1,1,3,tetrachloropropane in the vapor phase in a reaction zone with a catalyst comprising iron, to produce a product mixture comprising 1,1,3-trichloro-1-propene; and recovering said 1,1,3-trichloro-1-propene from the product mixture produced. Also disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising heating 1,1,1,3-tetrachloropropane in the liquid phase to produce a mixture comprising 1,1,3-trichloro-1-propene, cooling said mixture, separating hydrogen chloride from said mixture and recovering 1,1,3-trichloro-1-propene.

Claims (9)

1. A process for the manufacture of 1,1,3-trichloro-1-propene comprising: (a) contacting 1,1,1,3-tetrachloropropane in the vapor phase in a reaction zone with a catalyst to produce a product mixture comprising 1,1,3-trichloro-1-propene; and (b) recovering said 1,1,3-trichloro-1-propene from the product mixture produced in (a), wherein said catalyst is iron.

2. The process of claim 1 , wherein the contacting step is conducted under a flow of an inert carrier gas.

3. The process of claim 2 , wherein said inert carrier gas is nitrogen.

4. The process of claim 1 , wherein the temperature set point for said reaction zone is at least 300° C.

5. The process of claim 1 , wherein the temperature set point for said reaction zone is at least 350° C.

6. A process for the manufacture of 1,1,3-trichloro-1-propene comprising: (a) heating 1,1,1,3-tetrachloropropane in the liquid phase to a temperature of at least 175° C. for at least one hour to produce a product mixture comprising 1,1,3-trichloro-1-propene, (b) cooling said mixture, (c) separating HCl from said product mixture, and (d) recovering 1,1,3-trichloropropene.

7. The process of claim 6 , wherein the selectivity for producing 1,1,3-trichloro-1-propene is at least 90%.

8. The process of claim 6 , wherein the selectivity for producing 1,1,3-trichloro-1-propene is at least 95%.

9. The process of claim 1 wherein the catalyst is iron wool.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2012
From: NAPPA, MARIO JOSEPH; LOUSENBERG, ROBERT D.; JACKSON, ANDREW
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 027922/0080 →