IP Library Granted Patent US 10,427,998
Granted Patent B2
US 10,427,998 · App. 15/575,980 · Granted Oct 1, 2019

Compositions based on 1,1,3,3-tetrachloropropene

Inventors: Anne Pigamo (Francheville, FR); Bertrand Collier (Saint-Genis-Laval, FR)
Assignee: ARKEMA FRANCE
C07C17/206C07C17/093C07C17/25C07C17/266C07C17/269C07C17/383C09K5/044C09K5/045C09K2205/126C09K2205/24
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Quick Facts
Patent No.
US 10,427,998
App. No.
15/575,980
Granted
Oct 1, 2019
Kind
B2
Abstract

The present invention relates to compositions based on F-1230za (1,1,3,3-tetrachloropropene), or on a mixture consisting of F-1230za and F-1230zd (1,3,3,3-tetrachloropropene), the manufacture thereof, and also the use thereof in particular for the production of F-1233zdE (trans-1-chloro-3,3,3-trifluoropropene), F-1234zeE (trans-1,3,3,3-tetrafluoropropene), and/or F-245fa (1,1,1,3,3-pentafluoropropane).

Claims (25)

1. A composition comprising:

at least 99.5% by weight of 1,1,3,3-tetrachloropropene (F-1230za), or at least 99.5% by weight of a mixture comprising 1,1,3,3-tetrachloropropene and 1,3,3,3-tetrachloropropene (F-1230zd), and

at least one additional compound selected from the group consisting of chlorobutenes and chlorobutanes, wherein the amount of said additional compound or the total amount of said compounds represents a content of less than or equal to 500 ppm, in the composition.

2. The composition as claimed in claim 1 , in which said additional compound represents a content of less than or equal to 450 ppm, in the composition.

3. The composition as claimed in claim 1 , in which said additional compound is selected from the group consisting of monochlorobutanes, dichlorobutanes, trichlorobutanes, and tetrachlorobutanes.

4. The composition as claimed in claim 3 , in which said additional compound is selected from the group consisting of 1,1,4,4-tetrachlorobutane, 1,2,3,4-tetrachlorobutane, 1,1,1,3-tetrachlorobutane, and 1,1,3,3-tetrachlorobutane.

5. The composition as claimed in claim 1 , in which said additional compound is selected from the group consisting of monochlorobutenes, dichlorobutenes, trichlorobutenes, and tetrachlorobutenes.

6. The composition as claimed in claim 5 , in which said additional compound is selected from the group consisting of 1,2,4-trichlorobut-2-ene, 1,3-dichloro-2-chloromethylpropene, 1,1,3-trichlorobut-1-ene, 4,4,4-trichlorobut-1-ene, 1,2,3-trichloro-1-butene, 3,4,4-trichloro-1-butene, 2-chloromethyl-3,3-dichloropropene, 1,1,4-trichlorobut-2-ene, 3,3,4-trichlorobut-1-ene, 1,1,3-trichlorobut-2-ene, 1,3,3-trichlorobut-1-ene, 1,1,2-trichlorobut-1-ene, 1,1,1-trichlorobut-2-ene, 1,1,4-trichlorobut-2-ene, 1,3,4-trichlorobut-1-ene, 1,1,2-trichlorobut-2-ene, 1,2,3-trichlorobut-2-ene, 2-methyl-1,1,3-trichloro-1-propene, 1,2,4-trichlorobut-2-ene, and 2,3,4-trichlorobut-1-ene.

7. A process for manufacturing the composition as claimed in claim 1 , comprising the following steps:

reaction of carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane (F-240fa);

dehydrochlorination of F-240fa to obtain 1,1,3,3-tetrachloropropene (F-1230za);

one or more steps for separating out the F-1230za.

8. The process as claimed in claim 7 , in which the separation is performed by distillation or extraction, and/or by physicochemical separation on molecular sieves, alumina or active charcoal, and/or by membrane separation, optionally in the gas phase.

9. The process as claimed in claim 8 , in which a first separation step is performed via one or more distillations and a second separation step is performed by adsorption on molecular sieves, on active charcoal or on a mixture thereof.

10. The process as claimed in claim 8 , in which the separation step is performed by adsorption on zeolite, and optionally followed by gas-phase membrane separation.

11. The process as claimed in claim 8 , in which the step of separation by adsorption is performed at a temperature of between 0 and 120° C.

12. A process for manufacturing the composition as claimed in claim 1 , comprising the following steps:

reaction of carbon tetrachloride with ethylene to produce 1,1,1,3-tetrachloropropane (F-250fb);

chlorination of F-250fb to obtain 1,1,1,3,3-pentachloropropane (F-240fa);

dehydrochlorination of F-240fa to obtain 1,1,3,3-tetrachloropropene (F-1230za);

one or more steps for separating out the F-1230za.

13. A process for manufacturing 1-chloro-3,3,3-trifluoropropene (F-1233zd), and/or 1,3,3,3-tetrafluoropropene (F-1234ze) and/or 1,1,1,3,3-pentafluoropropane (F-245fa), by fluorination performed in the liquid phase and in the absence of catalyst, comprising the steps:

introducing into a fluorination reactor a stream comprising the composition as claimed in claim 1 .

14. The process as claimed in claim 13 for forming trans-1-chloro-3,3,3-trifluoropropene (F-1233zdE) or trans-1,3,3,3-tetrafluoropropene (F-1234zeE).

15. The process as claimed in claim 13 , followed by one or more steps for separating 1-chloro-3,3,3-trifluoropropene (F-1233zd), and/or 1,3,3,3-tetrafluoropropene (F-1234ze) and/or 1,1,1,3,3-pentafluoropropane (F-245fa) from the stream of products.

Assignments (7)
SECURITY INTEREST Recorded Jan 12, 2023
From: SPOLCHEMIE ZEBRA, A.S.
To: ARKEMA FRANCE
Reel/Frame 062360/0214 →
SECURITY INTEREST Recorded Jan 4, 2023
From: SPOLCHEMIE ZEBRA, A.S.
To: CESKA SPORITELNA, A.S.
Reel/Frame 062277/0281 →
RELEASE OF SECURITY INTEREST Recorded Dec 21, 2022
From: ARKEMA FRANCE
To: SPOLCHEMIE ZEBRA, A.S.
Reel/Frame 062169/0260 →
SECURITY INTEREST Recorded Mar 4, 2022
From: SPOLCHEMIE ZEBRA, A.S.
To: ARKEMA FRANCE
Reel/Frame 059178/0251 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 17, 2022
From: SPOLEK PRO CHEMICKOU A HUTNI VYROBU, AKCIOVA SPOLECNOST
To: SPOLCHEMIE ZEBRA, A.S.
Reel/Frame 059032/0835 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2020
From: ARKEMA FRANCE
To: SPOLEK PRO CHEMICKOU A HUTNI VYROBU, AKCIOVA SPOLECNOST
Reel/Frame 054737/0220 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2017
From: PIGAMO, ANNE; COLLIER, BERTRAND
To: ARKEMA FRANCE
Reel/Frame 044190/0845 →
Priority Claims (1)
FR 15 54655 · May 22, 2015 · national
Continuity (1)
Related Publication 20180148394A1 · May 31, 2018
Cited By (1)
US 12,391,634