Epoxide stabilization of fluorophosphite-metal catalyst system in a hydroformylation process
AssigneeEastman Chemical Company
InventorsThomas Allen Puckette, Ginette Struck Tolleson, Thomas James Devon, Jerome L. Stavinoha, Jr.
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Abstract
A process for stabilizing a fluorophosphite ligand in a hydroformylation reaction mixture having an α-olefin, hydrogen, carbon monoxide and a catalyst composition having a combination of a rhodium containing compound and one or more fluorophosphite compounds having the general formula: wherein R1 and R2 are hydrocarbyl radicals which contain a total of up to about 40 carbon atoms, the process includes the step of adding to the reaction mixture an epoxide in a sufficient amount to reduce the degradation of the fluorophosphite ligand.
Claims26
In a hydroformylation process having a reaction mixture which includes a catalyst composition comprising a combination of a transition metal compound selected from the Group VIII metals and one or more fluorophosphite compounds having the general formula:
- wherein R1 and R2 are hydrocarbyl radicals which contain a total of up to about 40 carbon atoms wherein the improvement comprises stabilizing said fluorophosphite compounds by adding to the reaction mixture an epoxide.
A process for stabilizing a fluorophosphite ligand in a hydroformylation reaction mixture having an α-olefin, hydrogen, carbon monoxide and a catalyst composition having a combination of a rhodium containing compound and one or more fluorophosphite compounds having the general formula:
- wherein R1 and R2 are hydrocarbyl radicals which contain a total of up to about 40 carbon atoms, said process comprising adding to the reaction mixture from about 0.001 to about 1.0 weight % of an epoxide, wherein the weight % is based on the total weight of the reaction mixture.
A process for stabilizing a,fluorophosphite ligand in a hydroformylation reaction mixture having an α-olefin, hydrogen, carbon monoxide and a catalyst composition having a combination of a rhodium containing compound and one or more fluorophosphite compounds having the general formula:
- said process comprising adding to the reaction mixture from about 0.001 to about 1.0 weight % of an epoxide wherein the weight % of the epoxide is based on the total weight of the reaction mixture and wherein:
- a) R1 and R2 are independently selected from the group consisting of ethyl, butyl, pentyl, hexyl, 2-ethylhexyl, octyl, decyl, dodecyl, octadecyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, anthracenyl and aryl group having the formula:
- wherein R3 and R4 are independently selected from the group consisting of alkyl, alkoxy, halogen, cycloalkoxy, formyl, alkanoyl, cycloalkyl, aryl, aryloxy, aroyl, carboxyl, carboxylate salts, alkoxycarbonyl, alkanoyloxy, cyano, sulfonic acid and sulfonate salts, wherein the alkyl moiety of alkyl, alkoxy, alkanoyl, alkoxycarbonyl and alkanoyloxy groups contains up to about 8 carbon atoms;
- m and n independently are 0, 1 or 2, wherein the total carbon atom content of the hydrocarbyl radicals represented by R1 and R2 is from 2 to 35 and wherein the ratio of gram moles fluorophosphite ligand to gram atoms rhodium is about 1:1 to 70:1;
- or
- b) R1 and R2 in combination is selected from the group consisting of ethylene, trimethylene, 1,3-butanediyl, 2,2-dimethyl-1,3-propanediyl, 1,1,2-tri-phenylethanediyl, 2,2,4-trimethyl-1,3-pentanediyl, and 1,2-cyclohexylene, a cyclohexylene, and an arylene group having the formula:
- or a radical having the formula:
- wherein A1 and A2 independently is an arylene radical having formula (V), (VI) or (VII) above and 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 or a group having the formula:
- wherein R5 is selected from the group consisting of hydrogen, alkyl and aryl, having formulas (II), (III) and (IV);
- R6 is selected from the group consisting of hydrogen and alkyl, and wherein —C(R5)(R6)— has from 1 to 8 carbon atoms;
- and
- wherein R3 and R4 are independently selected from the group consisting of alkyl, alkoxy, halogen, cycloalkoxy, formyl, alkanoyl, cycloalkyl, aryl, aryloxy, aroyl, carboxyl, carboxylate salts, alkoxycarbonyl, alkanoyloxy, cyano, sulfonic acid and sulfonate salts wherein the alkyl moiety of such alkyl, alkoxy, alkanoyl, alkoxycarbonyl and alkanoyloxy groups contains up to about 8 carbon atoms;
- p and q independently are 0, 1 or 2.
Dependencies are inferred from the claim text.