US 2003/0171623 A1 · Stabilization of fluorophosphite-containing catalysts

Abstract

Disclosed are novel catalyst systems comprising (1) a diorgano fluorophosphite ligand; (2) rhodium, wherein the ratio of gram moles fluorophosphite ligand (1) to gram atoms of rhodium is at least 1:1; and (3) a Group VIII metal, other than rhodium, or Group VIII metal-containing compound, in an amount effective to reduce the formation of HF during the use of the catalyst system. The presence of the other Group VIII metal decreases the amount of hydrogen fluoride produced during the use of the catalyst system. The hydrogen fluoride originates from very low level degradation of the ligand. Also disclosed are novel catalyst solutions of the aforesaid catalyst system and the use of the catalyst system in the hydroformylation of olefins to produce aldehydes.

Claims21

Dependent claims

A catalyst system comprising comprising (1) a diorgano fluorophosphite ligand;

and (2) rhodium, wherein the ratio of gram moles fluorophosphite ligand to gram atoms of rhodium is at least 1:1;
and (3) a Group VIII metal, other than rhodium, or Group VIII metal-containing compound, in an amount effective to reduce the formation of HF during the use of the catalyst system.

A catalyst system comprising (1) one or more fluorophosphite compounds having the general formula

18
wherein R1 and R2 collectively represent an arylene group having the formula
19
or a radical having the formula
20
wherein
each of A1 and A2 is an arylene radical having formula (V), (VI) or (VIII) above wherein each ester oxygen atom of fluorophosphite (I) is bonded to a ring carbon atom of A1 and A2;
X is (i) a chemical bond directly between ring carbon atoms of A1 and A2;
or (ii) an oxygen atom, a group having the formula —(CH2)y— wherein y is 2 to 4 or a group having the formula
21
wherein R5 is hydrogen, alkyl or aryl;
R6 is hydrogen or alkyl;
and the group —C(R5)(R6)— contains up to about 8 carbon atoms;
and
wherein R3 and R4 are independently selected from alkyl, alkoxy, halogen, cycloalkoxy, formyl, alkanoyl, cycloalkyl, aryl, aryloxy, aroyl, carboxyl, carboxylate salts, alkoxycarbonyl, alkanoyloxy, cyano, sulfonic acid and sulfonate salts in which the alkyl moiety of such alkyl, alkoxy, alkanoyl, alkoxycarbonyl and alkanoyloxy groups contains up to about 8 carbon atoms;
p and q each is 0, 1 or 2;
the total carbon atom content of the radical collectively represented by R1 and R2 is about 12 to 35;
(2) rhodium wherein the ratio of gram moles fluorophosphite ligand to gram atoms rhodium is about 1:1 to 500:1;
and (3) a Group VIII metal selected from platinum, cobalt, ruthenium or palladium wherein the gram atom ratio of the Group VIII metal:rhodium metal is in the range of about 1:1 to 5:1.

16 more elements

A catalyst solution comprising

(1) one or more dihydrocarbyl fluorophosphite compounds having the general formula
25
wherein R1 and R2 are aromatic hydrocarbyl radicals which contain a total of up to about 40 carbon atoms;
(2) rhodium;
(3) a Group VIII metal, other than rhodium, or Group VIII metal-containing compound, in an amount effective to reduce the formation of HF during the use of the catalyst system and
(4) a hydroformylation solvent;
wherein the ratio of gram moles fluorophosphite ligand to gram atoms rhodium is at least 1:1.

4 more elements

A process for preparing an aldehyde which comprises contacting an olefin, hydrogen and carbon monoxide with a solution of a catalyst system comprising (1) one or more dihydrocarbyl fluorophosphite compounds having the formula

30
wherein R1 and R2 are aromatic hydrocarbyl radicals which contain a total of up to about 40 carbon atoms;
(2) rhodium wherein the ratio of gram moles fluorophosphite ligand to gram atoms rhodium is at least 1:1;
(3) a Group VIII metal, other than rhodium, or Group VIII metal-containing compound, in an amount effective to reduce the formation of HF during the process;
and (4) a hydroformylation solvent.

2 more elements

Dependencies are inferred from the claim text.

Stabilization of fluorophosphite-containing catalysts

Life of this patent

Stabilization of fluorophosphite-containing catalysts

Life of this patent

Abstract

Claims21