US 7,351,870 B2 · Synthesis of carbon-labeled perfluoroalkyl compounds

Abstract

Various 13C and 14C carbon labeled compounds Rf—bCF(U)y(T)zFormula 1A or Rf—bCF2bCF(U)y(T)zFormula 1B wherein Rf is a linear or branched perfluoroalkyl radical Z(CmF2m)—, m is 1, 3 to 20, or a mixture thereof; Z is F when m is 1, and Z is F, Cl, or H when m is 3 to 20 or a mixture thereof; b is 13 or 14; y is 1, and z is 0 or 1; and when y and z are each 1, U is F, and T is selected from the group consisting of monovalent radicals —X wherein X is I or Br, —CH2—CH2—X, —CH═CH2, —CH2—CH2—OH, —CH2—COOH, —CH2OH, —bCH2OH, —COOH, —bCOOH, —O—CF(CF3)—C(O)F, —O—CF(CF3)—X, —SO2Y wherein Y is H, F or Cl, and —SO3H; and when y is 1, and z is 0, U is selected from the group consisting of divalent radicals ═CH—COOH, ═CH—CH2—OH, and ═O, are disclosed, and a process for their preparation which selectively introduces 13C and 14C carbon labels into a fluoroalkyl chain.

Claims25

Dependent claims

A compound having the formula

Rf—bCF(U)y(T)z Formula 1A or
Rf—bCF2bCF(U)y(T)z Formula 1B
wherein
Rf is a linear or branched perfluoroalkyl radical Z(CmF2m)—,
m is 1, 3 to 20, or a mixture thereof;
Z is F when m is 1, and Z is F, Cl, or H when m is 3 to 20, or a mixture thereof;
b is 13 or 14;
y is 1 and z is 0 or 1;
and
when y and z are each 1, U is F, and T is selected from the group consisting of monovalent radicals —X wherein X is I or Br, —CH2—CH2—X, —CH═CH2, —CH2—CH2—OH, —CH2—COOH, —CH2OH, —bCH2OH, —COOH, —bCOOH, —O—CF(CF3)—C(O)F, —O—CF(CF3)—X, —SO2Y wherein Y is H, F or Cl, and —SO3H;
and
when y is 1, and z is 0, U is selected from the group consisting of divalent radicals ═CH—COOH, ═CH—CH2—OH, and ═O.

9 more elements

Dependencies are inferred from the claim text.

Synthesis of carbon-labeled perfluoroalkyl compounds

Life of this patent

Synthesis of carbon-labeled perfluoroalkyl compounds

Life of this patent

Abstract

Claims25