Abstract: Hydroformylation catalysts which can tolerate high levels of alkyne impurities in an olefin feed stream. The catalysts are composed of rhodium in combination with fluorophosphite ligands or rhodium in combination with certain bidentate ligands. Propionaldehyde has been produced by the hydroformylation of ethylene streams containing up to 1000 parts per million of acetylene without any loss of activity due to the presence of the acetylene. Ethylene contaminated with acetylene at 10,000 ppm can also be converted to propionaldehyde but some loss of activity occurs.

Abstract: Disclosed is a process for the preparation of 2,5-dihydrofuran compounds by contacting an olefinically-substituted ethylene carbonate compound with a catalyst comprising an acidic component and a halogen component. The process is especially useful for the preparation of 2,5-dihydrofuran from vinyl ethylene carbonate (4-ethenyl-1,3-dioxolane-2-one) which is readily available from 3,4-epoxy-1-butene.

Abstract: Disclosed in a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycyclo-alkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and epoxycycloalkenes, to the corresponding epoxyalkanes and epoxycycloalkanes using a solution of a complex rhodium catalyst whereby the olefinic unsaturation is hydrogenated without significant hydrogenolysis of the conjugated epoxy group.

Abstract: Disclosed is a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycycloalkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and .gamma.,.delta.-epoxycycloalkenes, to the corresponding epoxyalkanes and epoxycycloalkanes using a solution of a complex rhodium catalyst whereby the olefinic unsaturation is hydrogenated without significant hydrogenolysis of the conjugated epoxy group.

Abstract: Disclosed are bis-phosphine compounds having the general formula ##STR1## wherein: each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is an arylene radical 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 ##STR2## constitutes a 5-membered ring; each of A.sup.5 and A.sup.6 is an arylene radical 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; andR.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.

Abstract: Disclosed are bis-phosphine compounds having the general formula ##STR1## wherein: each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is an arylene radical 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 ##STR2## constitutes a 5-membered ring; each of A.sup.5 and A.sup.6 is an arylene radical 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; andR.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.

Abstract: A method for the preparation of biaryl compounds is disclosed which comprises contacting an aromatic halide in the presence of a catalyst comprising zerovalent nickel, a bidentate phosphorus-containing coordinating ligand and a reducing metal in a polar, aprotic solvent system for a time and under conditions suitable for the formation of biaryl compound.

Abstract: A process is disclosed for preparing biaryl, bidentate ligands comprising:(1) contacting a biaryl compound having the structural formula: ##STR1## with a proton abstracting agent under conditions suitable to form a biaryl dianion, which is then(2) contacted with a Group V compound of the formula: ##STR2## where X' is halogen or a suitable leaving group.

Abstract: A method for the preparation of biaryl compounds is disclosed which comprises contacting an aryl halide with a tertiary-alkyl organometallic reagent (or the precursor components thereof) in the presence of a catalyst comprising a nickel compound and a coordinating ligand under conditions suitable for the formation of biaryl compound.In an alternate embodiment of the present invention, nickel(O) compounds are prepared from nickel(II) compounds by contacting a nickel(II) compound with a combination of an organophosphine and a bidentate nitrogen-containing coordinating ligand, and a tertiary-alkyl organometallic reagent (or the precursor components thereof) in an aprotic, non-polar, ether-containing solvent system for a time and under conditions suitable for the formation of nickel(0) compound.

Abstract: The hydroformylation of olefins with rhodium complex catalysts is described. The catalysts employed comprise a rhodium complex with at least one bidentate ligand having a specified structure, ##STR1## Hydroformylation reactions at relatively low temperatures and pressure and yet with high rates of reaction and high selectivity to aldehyde product are obtained by the practice of the present invention.

Abstract: The hydroformylation of olefins with rhodium complex catalysts is described. The catalysts employed comprise a rhodium complex with at least one bidentate ligand having a specified structure, ##STR1## Hydroformylation reactions at relatively low temperatures and pressure and yet with high rates of reaction and high selectivity to aldehyde product are obtained by the practice of the present invention.

Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each Ar is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and the y bonds are attached to adjacent carbon atoms on the ring structures;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralyky, alkaryl, alkoxyalky, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 where Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatieves thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.

Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each AR is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and the y bonds are attached to adjacent carbon atoms on the ring structures;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 were Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatives thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.

Abstract: A method for the preparation of biaryl compounds is disclosed which comprises contacting an aryl halide with a tertiary-alkyl organometallic reagent (or the precursor components thereof) in the presence of a catalyst comprising a nickel compound and a coordinating ligand under conditions suitable for the formation of biaryl compound.In an alternative embodiment of the present invention, nickel(0) compounds are prepared from nickel(II) compounds by contacting a nickel(II) compound with a combination of an organophosphine and a bidentate nitrogen-containing coordinating ligand, and a tertiary-alkyl organometallic reagent (or the precursor components thereof) in an aprotic, non-polar, ether-containing solvent system for a time and under conditions suitable for the formation of nickel(0) compound.

Abstract: A method for the preparation of biaryl compounds is disclosed which comprises contacting an aromatic halide in the presence of a catalyst comprising zerovalent nickel, a bidentate phosphorus-containing coordinating ligand and a reducing metal in a polar, aprotic solvent system for a time and under conditions suitable for the formation of biaryl compound.

Abstract: A method for the preparation of biaryl compounds is disclosed which comprises contacting an aryl halide under conditions suitable to form a Grignard reagent and thereafter contacting the Grignard reagent with an aryl chloride in the presence of a catalyst comprising a nickel compound and a coordinating ligand under conditions suitable for the formation of biaryl compound. In an alternate embodiment of the present invention, biaryl compounds are prepared directly from aryl halides in a single reaction vessel by contacting aryl halide with elemental magnesium and a nickel catalyst comprising a nickel compound and a coordinating ligand in an aprotic, non-polar, ether-containing solvent system for a time and under conditions suitable for the formation of biaryl compound.

Abstract: A novel ligand for use in hydroformylation reactions wherein at least one olefin having from 2 to 20 carbon atoms is contacted in a reaction zone at a temperature of from about 20.degree. C. to about 250.degree. C. and a pressure of from about 50 psig to about 800 psig with hydrogen, carbon monoxide, and a catalyst containing rhodium, the ligand having the formula ##STR1## wherein: n is 1-4;each R is independently selected from hydrogen, alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl or cyano;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.1 substituents; andeach Y is independently selected from the elements N, P, As, Sb and Bi.

Abstract: The process for preparing a bidentate ligand comprising the steps,(1) contacting with ozone under ozonolysis conditions a suspension in a hydroxylic reaction medium of phenanthrene or a phenanthrene derivative to form an ozonated intermediate,(2) contacting said ozonated intermediate with a reducing agent under conditions appropriate to form the corresponding diol,(3) contacting said diol with a latent displaceable functional group under conditions appropriate to convert the diol to the corresponding difunctional biaryl compound, and(4) contacting said difunctional biaryl compound, with an anion of N, P, As, Sb or Bi under conditions appropriate to form the desired bidentate ligand.

Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each Ar is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and y bonds are attached to adjacent carbon atoms on the ring structure;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 were Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatives thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.

Abstract: The hydroformylation of olefins with rhodium complex catalysts is described. The catalysts employed comprises a rhodium complex with at least one phosphine having a specified structure, e.g., tris(benzyl)phosphine. Preferred phosphines have a pKa in the range of about 3.5 up to 5.3 and a cone angle in the range of about 160.degree. up to 195.degree.. Hydroformylation reactions at relatively low temperatures and pressure and yet with high rates of reaction and high selectivity to aldehyde product are obtained by the practice of the present invention.