IP Library Granted Patent US 8,889,928
Granted Patent B2
US 8,889,928 · App. 13/796,558 · Granted Nov 18, 2014

Method to improve 1,1,3-trichloropropene and/or 3,3,3-trichloropropene selectivity during the dehydrochlorination of 1,1,1,3-tetrachloropropane

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Quick Facts
Patent No.
US 8,889,928
App. No.
13/796,558
Granted
Nov 18, 2014
Kind
B2
Abstract

This invention relates to a method to improve 1,1,3-trichloropropene (HCC-1240za) and/or 3,3,3-trichloropropene (HCC-1240zf) selectivity in the dehydrochlorination of 1,1,1,3-tetrachloropropane (HCC-250fb). In normal practice, FeCl 3 is used as the catalyst for the dehydrochlorination of HCC-250fb to produce 1,1,3-trichloropropene and/or 3,3,3-trichloropropene. The present invention demonstrates that when using FeCl 3 as the catalyst for 1,1,1,3-tetrachloropropane dehydrochlorination, the reaction product contains significant amounts of high boiling compounds, such as pentachlorocyclohexene and/or hexachlorocyclohexane species. The addition of one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system, inhibits the formation of these high boiling compounds and improves selectivity to the desired product.

Claims (26)

1. In the process of the catalytic dehydrochlorination of 1,1,1,3-tetrachloro-propane (HCC-250fb) to produce 1,1,3-trichloropropene and/or 3,3,3-trichloropropene, the improvement comprising the addition of one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system to inhibit the formation of high boiling compounds, and wherein the product selectivity to 1,1,3-trichloropropene and/or 3,3,3-trichloropropene is at least about 50% or higher.

2. The process of claim 1 , wherein the dehydrochlorination catalyst comprises one or more metal halides or mixtures thereof.

3. The process of claim 1 , wherein the dehydrochlorination catalyst comprises FeCl 3 .

4. The process of claim 3 , wherein the dehydrochlorination reaction temperature is from 50° to 140° C.

5. The process of claim 3 , wherein the dehydrochlorination reaction temperature is from 80° to 120° C.

6. The process of claim 3 , wherein the dehydrochlorination reaction time is from 0.5 to 10 hours.

7. The process of claim 3 , wherein the dehydrochlorination reaction time is from 1 to 4 hours.

8. The process of claim 3 , wherein the weight ratio of the catalyst to the reactant 1,1,1,3-tetrachloropropane is from above 0 to about 5% by weight.

9. The process of claim 3 , wherein the weight ratio of the catalyst to the reactant 1,1,1,3-tetrachloropropane is from 0.01% to 0.5% by weight.

10. In the process of the catalytic dehydrochlorination of 1,1,1,3-tetrachloro-propane (HCC-250fb) to produce 1,1,3-trichloropropene and/or 3,3,3-trichloropropene, the improvement comprising the addition of one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system to inhibit the formation of high boiling compounds;

wherein the dehydrochlorination catalyst comprises FeCl 3 ; and

wherein the weight ratio of UV-stabilizer and/or anti-oxidant and/or their mixtures to the reactant 1,1,1,3-tetrachloropropane ranges from above 0 to about 2% by weight.

11. In the process of the catalytic dehydrochlorination of 1,1,1,3-tetrachloro-propane (HCC-250fb) to produce 1,1,3-trichloropropene and/or 3,3,3-trichloropropene, the improvement comprising the addition of one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system to inhibit the formation of high boiling compounds;

wherein the dehydrochlorination catalyst comprises FeCl 3 ; and

wherein the weight ratio of UV-Stabilizer and/or anti-oxidant and/or their mixtures to the reactant 1,1,1,3-tetrachloropropane ranges from about 0.0001% to about 0.5%.

12. In the process of the catalytic dehydrochlorination of chlorinated alkanes to produce chlorinated alkenes, the improvement comprising the addition of one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system to inhibit the formation of high boiling compounds, and

wherein the UV-Stabilizer and/or anti-oxidant and/or their mixtures is selected from the group consisting of benzophenones, polyphenols, amines, hydroquinones, butylated hydroxy anisoles (BHA), thymols, and mixtures thereof; and wherein the weight ratio of UV-Stabilizer and/or anti-oxidant and/or their mixtures to the reactant 1,1,1,3-tetrachloropropane ranges from about 0 to about 2% by weight.

13. The process of claim 12 , wherein the dehydrochlorination reaction system comprises the dehydrochlorination of 1,1,1,3-tetrachloropropane to produce 1,1,3-trichloropropene and/or 3,3,3-trichloropropene.

14. The process of claim 12 , wherein the UV-Stabilizer and/or anti-oxidant and/or their mixtures is selected from the group consisting of methoxy-hydroquinones, triethylamines, di-isopropyl amines, and mixtures thereof.

15. A process for the catalytic dehydrochlorination of chlorinated alkanes to produce chlorinated alkenes using one or more metal halides or mixtures as the catalyst, comprising adding one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system to improve the selectivity to the product chlorinated alkenes, wherein the UV-stabilizer and/or anti-oxidant compounds are selected from the group consisting of benzophenones, polyphenols, amines, hydroquinones, butylated hydroxy anisoles (BHA), thymols, and mixtures thereof; and wherein the weight ratio of UV-Stabilizer and/or anti-oxidant and/or their mixtures to the reactant 1,1,1,3-tetrachloropropane ranges from about 0 to about 2% by weight.

16. A process for the catalytic dehydrochlorination of chlorinated alkanes to produce chlorinated alkenes using one or more metal halides or mixtures as the catalyst, comprising adding one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system to improve the selectivity to the product chlorinated alkenes, wherein the UV-stabilizer and/or anti-oxidant compounds are selected from the group consisting of benzophenones, polyphenols, amines, hydroquinones, butylated hydroxy anisoles (BHA), thymols, and mixtures thereof; and

wherein the product selectivity is at least about 50% or higher.

17. The process of claim 16 , wherein the product selectivity is at least about 70% or higher.

18. The process of claim 16 , wherein the product selectivity is at least about 95% or higher.

19. The process of claim 15 , wherein the UV-stabilizer and/or anti-oxidant compounds are selected from the group consisting of methoxy-hydroquinones, triethylamines, di-isopropyl amines, and mixtures thereof.

20. The process of claim 16 , wherein the UV-stabilizer and/or anti-oxidant compounds are selected from the group consisting of methoxy-hydroquinones, triethylamines, di-isopropyl amines, and mixtures thereof.

Assignments (2)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2013
From: YANG, TERRIS; TUNG, HSUEH SUNG
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 029974/0991 →