IP Library Granted Patent US 8,779,196
Granted Patent B2
US 8,779,196 · App. 13/048,230 · Granted Jul 15, 2014

Polyfluoroalkylsulfonamido alkyl halide intermediate

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Quick Facts
Patent No.
US 8,779,196
App. No.
13/048,230
Granted
Jul 15, 2014
Kind
B2
Abstract

The present invention relates to a polyfluoroalkylsulfonamido alkyl halide intermediate. The invention also relates to the use of the aforementioned halide intermediate to prepare a mixture of polyfluoroalkylsulfonamido alkyl amines including at least one polyfluoroalkylsulfonamido alkyl amine and its analog, a di(polyfluoroalkylsulfonamido alkyl) amine.

Claims (33)

1. A polyfluoroalkylsulfonamido alkyl halide represented by

R f —(CH 2 ) n —S(O) 2 —N(R 1 )—C(R 5 )(R 6 )—C m H 2m —X  (Formula 1)

wherein:

R f is chosen from a C 2 -C 12 polyfluoroalkyl optionally interrupted by one to four groups

chosen from: —O—, —S—, —S(O)—, and —S(O) 2 —;

n is 2; R 1 , R 5 , R 6 are independently chosen from hydrogen, C 1 to C 6 hydroxyalkyl, C 1 to C 6 halogen substituted alkyl, or a C 1 to C 6 linear or branched alkyl;

C m H 2m is linear or branched alkyl, and

m is chosen from an integer from 1 to 10; and

X is a halogen selected from the group consisting of Cl, Br, I and mixtures thereof.

2. The polyfluoroalkylsulfonamido alkyl halide of claim 1 wherein

R f is chosen from CF 3 (CF 2 ) 5 , or CF 3 (CF 2 ) 3 ;

R 1 , R 5 , and R 6 are the same and are hydrogen;

n is 2;

m is 2; and

X is chlorine.

3. A method for making the polyfluoroalkylsulfonamido alkyl halide of claim 1 comprising reacting a polyfluoroalkylsulfonic compound with a monoamino alkyl halide, or salt thereof under suitable conditions to make a polyfluoroalkylsulfonamido alkyl halide wherein:

i) the polyfluoroalkylsulfonic compound is represented by

R f —(CH 2 ) n —S(O) 2 —Y  (Formula 3)

wherein Y is chosen from aryloxy, substituted aryloxy, or a halide such as F, Cl, or Br; and

ii) the monoamino alkyl halide or salt thereof is represented by

HN(R 1 )—C(R 5 )(R 6 )—C m H 2m —X  (Formula 4A)

or

[H 2 N(R 1 )—C(R 5 )(R 6 )—C m H 2m —X] + X −   (Formula 4B)

wherein each X is a halogen independently selected from the group consisting of from Cl, Br, I and mixtures thereof.

4. A method for making the polyfluoroalkylsulfonamido alkyl halide of claim 1 comprising reacting a polyfluoroalkylsulfonamido alkyl alcohol with a halogenating agent under suitable conditions to make a polyfluoroalkylsulfonamido alkyl halide wherein the polyfluoroalkylsulfonamido alkyl alcohol is represented by

R f —(CH 2 ) n —S(O) 2 —N(R 1 )—C(R 5 )(R 6 )—C m H 2m —OH  (Formula 5).

5. The method for making the polyfluoroalkylsulfonamido alkyl halide of claim 4 wherein the halogenating agent is selected from the group consisting of HCl, HBr, HI, SOCl 2 , SOBr 2 , SOI 2 , PCl S , PBr 3 , and PI 3 .

6. A method for making the polyfluoroalkylsulfonamido alkyl halide of claim 4 wherein the polyfluoroalkylsulfonamido alkyl alcohol is made by reacting a polyfluoroalkylsulfonic compound with an amino alkyl alcohol under suitable conditions to make the polyfluoroalkylsulfonamido compound wherein:

i) the polyfluoroalkylsulfonic compound is represented by

R f —(CH 2 ) n —S(O) 2 —Y  (Formula 3)

Y is chosen from aryloxy, substituted aryloxy, or a halide such as F, Cl, or Br; and

ii) the amino alkyl alcohol is represented by

HN(R 1 )—C(R 5 )(R 6 )—C m H 2m —OH  (Formula 6).

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 →
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 May 19, 2011
From: SHTAROV, ALEXANDER BORISOVICH; PASHOVYCH, VOLODYMYR B.
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 026306/0631 →