IP Library Granted Patent US 8,884,084
Granted Patent B2
US 8,884,084 · App. 13/078,320 · Granted Nov 11, 2014

Process for the manufacture of halocarbons and selected compounds and azeotropes with HF

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,884,084
App. No.
13/078,320
Granted
Nov 11, 2014
Kind
B2
Abstract

A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR 1 R 2 CBR 3 R 4 (where A, B, R 1 , R 2 , R 3 , and R 4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR 1 R 2 ═CR 3 R 4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. Azeotropes of CClF 2 CH 2 CF 3 with HF and azeotropes of CF 3 CH 2 CHF 2 with HF are also disclosed; as are process for producing such azeotropes.

Claims (5)

1. A method of producing an azeotropic composition comprising HF and CF3CH2CHF2,

reacting CCl4 with CH2=CHCl to produce CCl3CH2CHCl2 and

reacting said CCl3CH2CHCl2 with HF to produce an azeotropic composition comprising HF and CF3CH2CHF2, wherein the azeotropic composition is from about

44 to 84 mole percent HF; and from about 56 to 16 mole percent CF3CH2CHF2; said composition exhibiting a relative volatility of about 1 at a pressure within the range of 5.5 kPa to 3850 kPa when the temperature is adjusted within the range of −50° C. to 130 C.

2. The method of claim 1 , wherein the step of reacting CCl4 with CH2=CHCl takes place in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases, and in the presence of a catalyst system containing (i) at least one catalyst selected from the group consisting of monovalent and divalent copper and (ii) a promoter selected from aromatic and aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring, to produce CCl3CH2CHCl2.

Assignments (3)
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 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 →