US 7,321,062 B2 | ||
Process for the preparation of (per) fluorinated mono-functional carbonyl compounds | ||
Giovanni Fontana, Verona (Italy); and Walter Navarrini, Milan (Italy) | ||
Assigned to Solvay Solexis S.p.A., Milan (Italy) | ||
Filed on Jan. 09, 2004, as Appl. No. 10/753,548. | ||
Claims priority of application No. MI2003A0018 (IT), filed on Jan. 09, 2003. | ||
Prior Publication US 2004/0147780 A1, Jul. 29, 2004 | ||
This patent is subject to a terminal disclaimer. | ||
Int. Cl. C07C 45/00 (2006.01); C07C 53/38 (2006.01); C07C 51/58 (2006.01) |
U.S. Cl. 562—864 [562/849; 568/407] | 18 Claims |
1. A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula:
F—A—(RF)t—B—C(O)X1 (I)
wherein:
X1=F, CF3;
t=0, 1;
A, B equal to or different from each other, are independently C1-C5 (per)fluoroalkylene groups or linear or branched C1-C5 (per)fluorooxyalkylene groups, optionally containing one or more Cl and/or H atoms;
RF is selected from the following groups:
—Rf1—, —ORf1O— wherein Rf1=C1-C20 perfluoroalkylene;
—ORf2—, wherein Rf2 is a perfluorooxyalkylene chain containing one or more of the following units statistically distributed along the backbone:
(C3F6O), selected between (CF2CF(CF3)O) or (CF(CF3)CF2O);
(CFX1O) wherein X1 is F or CF3;
(C2F4O);
(CF2(CF2)x′CF2O) wherein x′ is an integer equal to 1 or 2;
(CR4R5CF2CF2O) wherein R4, and R5 are equal to or different from each other and selected between H, Cl, and wherein one fluorine atom of the perfluoromethylene
unit is optionally substitued with H, Cl or (per)fluoroalkyl;
wherein the carbonyl groups of a (per)fluorinated di-functional carbonyl compound of formula:
X2(O)C—A—(RF)t—B—C(O)X1 (III)
wherein:
X1, RF, t, A and B have the above meanings;
X2, equal to or different from X1, has the same meanings as X1;
are fluorinated with elemental fluorine in the presence of a catalyst based on metal fluorides having formula MeFy.zHF, Me
being an alkaline or alkaline-earth metal or Ag, y=1 or 2, z being an integer equal to 0,
carrying out said reaction at a temperature in the range of 40° C. to 300° C. such that it leads to the formation of C(O)FX2 wherein X2 is as above, said fluorination being carried out by using a fluorine amount which at most is the necessary amount to obtain
the total conversion of the starting compound (III).
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