IP Library Granted Patent US 9,139,498
Granted Patent B2
US 9,139,498 · App. 13/988,121 · Granted Sep 22, 2015

Catalytical synthesis of hydrohalocarbons

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Quick Facts
Patent No.
US 9,139,498
App. No.
13/988,121
Granted
Sep 22, 2015
Kind
B2
Abstract

A process is disclosed for producing addition compound CF 3 CCl 2 CH 2 CClXR, wherein X═H, F, Cl or Br, and R═H or a perhalogenated alkyl group, provided that X and R are not both H. The process involves a liquid phase reaction of 1,1,1-trichlorotrifluoroethane with CH 2 ═CXR in the presence of an addition catalyst.

Claims (13)

1. A liquid phase process comprising reacting 1,1,1-trichlorotrifluoroethane with CH 2 ═CXR in the presence of an addition catalyst to produce a product mixture comprising addition compound CF 3 CCl 2 CH 2 CClXR, wherein X═H, F, Cl or Br, and R═H or a perhalogenated alkyl group, provided that X and R are not both H, wherein the catalyst is not a copper catalyst and CH 2 ═CXR is selected from the group consisting of CF 3 CH═CH 2 , CF 3 CF 2 CH═CH 2 , and CF 3 CF═CH 2

and provided that

when said CH2═CXR is CF3CH═CH2, said addition compound CF3CCl2CH2CClXR is CF3CCl2CH2CHClCF3;

when said CH2═CXR is CF3CF2CH═CH2, said addition compound CF3CCl2CH2CClXR is CF3CCl2CH2CHClCF2CF3; and

when said CH2═CXR is CF3CF═CH2 and said addition compound CF3CCl2CH2CClXR is CF3CCl2CH2CFClCF3.

2. The liquid phase process of claim 1 wherein said reaction is conducted at the temperature of from about 60° C. to about 240° C.

3. The liquid phase process of claim 1 wherein said addition catalyst is an iron catalyst comprising iron and ferric chloride.

4. The liquid phase process of claim 3 wherein said ferric chloride is anhydrous FeCl 3 .

5. The liquid phase process of claim 3 wherein a co-catalyst is used together with said iron catalyst and wherein said co-catalyst is an alkyl or aryl phosphate.

6. The liquid phase process of claim 5 wherein said co-catalyst is selected from the group consisting of triethyl phosphate, tributyl phosphate, phenyl diethyl phosphate, diethyl phosphate, dibutyl phosphate, phenyl phosphate and butyl phosphate.

7. The liquid phase process of claim 3 wherein said reaction is conducted at the temperature of from about 60° C. to about 240° C.

8. The liquid phase process of claim 1 further comprising recovering said addition compound CF 3 CCl 2 CH 2 CClXR from the product mixture.

9. The liquid phase process of claim 8 wherein said addition compound CF 3 CCl 2 CH 2 CClXR is recovered from the product mixture by distillation.

Assignments (5)
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2015
From: NAPPA, MARIO JOSEPH; SWEARINGEN, EKATERINA N.; STERLIN, SERGEI RAFAILOVICH
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 036979/0691 →
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 →