Hydroformylation process using novel phosphine-rhodium catalyst system

A phosphine compound having the formula ##STR14## wherein:

• each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein (i) each phosphorus atom P is bonded to a ring carbon atom of A.sup.1 and A.sup.2 and to a ring carbon atom of A.sup.3 and A.sup.4, (ii) A.sup.1 and A.sup.2, and A.sup.3 and A.sup.4 are bonded to each other by ring carbon atoms and (iii) each of the residues ##STR15## constitutes a 5-membered ring;
• each of A.sup.5 and A.sup.6 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein A.sup.5 and A.sup.6 are bonded to each other and to each of methylene groups CH.sub.2 by ring carbon atoms and methylene groups CH.sub.2 are connected to each other through a chain of 4 carbon atoms;
• and
• the arylene groups which each of A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and A.sup.6 represent are selected from the groups having the formulas ##STR16## wherein R.sup.5 and R.sup.6 are independently selected from alkyl of up to about 4 carbon atoms;
• and m and n independently are 0, 1 or 2.

A catalyst system comprising

• (1) a phosphine compound having the formula ##STR21## wherein:
• each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein (i) each phosphorus atom P is bonded to a rind carbon atom of A.sup.1 and A.sup.2 and to a ring carbon atom of A.sup.3 and A.sup.4, (ii) A.sup.1 and A.sup.2, and A.sup.3 and A.sup.4 are bonded to each other by ring carbon atoms and (iii) each of the residues ##STR22## constitutes a 5-membered ring;
• each of A.sup.5 and A.sup.6 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein A.sup.5 and A.sup.6 are bonded to each other and to residues R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 by ring carbon atoms and R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 are connected to each other through a chain of 4 carbon atoms;
• and
• R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents hydrogen or a hydrocarbyl radical containing up to about 8 carbon atoms;
• and
• (2) rhodium.

A catalyst system comprising

• (1) a phosphine compound having the formula ##STR24## wherein:
• each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein (i) each phosphorus atom P is bonded to a ring carbon atom of A.sup.1 and A.sup.2 and to a ring carbon atom of A.sup.3 and A.sup.4, (ii) A.sup.1 and A.sup.2, and A.sup.3 and A.sup.4 are bonded to each other by ring carbon atoms and (iii) each of the residues ##STR25## constitutes a 5-membered ring;
• each of A.sup.5 and A.sup.6 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein A.sup.5 and A.sup.6 are bonded to each other and to each of methylene groups CH.sub.2 by ring carbon atoms and methylene groups CH.sub.2 are connected to each other through a chain of 4 carbon atoms;
• and the arylene groups which each of A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and A.sup.6 represent are selected from the groups having the formulas ##STR26## wherein R.sup.5 and R.sup.6 are independently selected from alkyl of up to about 4 carbon atoms;
• and m and n independently are 0, 1 or 2;
• and
• (2) rhodium;
• wherein the mole ratio of (1):(2) is in the range of about 100:1 to 1:1.

A catalyst solution comprising

• (1) a phosphine compound having the formula ##STR30## wherein:
• each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein (i) each phosphorus atom P is bonded to a ring carbon atom of A.sup.1 and A.sup.2 and to a ring carbon atom of A.sup.3 and A.sup.4, (ii) A.sup.1 and A.sup.2, and A.sup.3 and A.sup.4 are bonded to each other by ring carbon atoms and (iii) each of the residues ##STR31## constitutes a 5-membered ring;
• each of A.sup.5 and A.sup.6 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein A.sup.5 and A.sup.6 are bonded to each other and to residues R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 by ring carbon atoms and R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 are connected to each other through a chain of 4 carbon atoms;
• and
• R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents hydrogen or a hydrocarbyl radical containing up to about 8 carbon atoms;
• (2) rhodium;
• and
• (3) a hydroformylation solvent.

A catalyst solution comprising

• (1) a phosphine compound having the formula ##STR33## wherein:
• each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein (i) each phosphorus atom P is bonded to a ring carbon atom of A.sup.1 and A.sup.2 and to a ring carbon atom of A.sup.3 and A.sup.4, (ii) A.sup.1 and A.sup.2, and A.sup.3 and A.sup.4 are bonded to each other by ring carbon atoms and (iii) each of the residues ##STR34## constitutes a 5-membered ring;
• each of A.sup.5 and A.sup.6 is a carbocyclic arylene radical containing 6 to 10 ring carbon atoms wherein A.sup.5 and A.sup.6 are bonded to each other and to each of methylene groups CH.sub.2 by ring carbon atoms and methylene groups CH.sub.2 are connected to each other through a chain of 4 carbon atoms;
• and the arylene groups which each of A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5 and A.sup.6 represent are selected from the groups having the formulas ##STR35## wherein R.sup.5 and R.sup.6 are independently selected from alkyl of up to about 4 carbon atoms;
• and m and n independently are 0, 1 or 2;
• (2) rhodium;
• and
• (3) a hydroformylation solvent
• wherein the mole ratio of (1):(2) is in the range of about 100:1 to 1:1.