Hoechst Celanese Corporation

Celanese Gmbh

Celanese International Corporation

Jerry D Unruh

Gabriel R Chapa

Brigitte E Segmuller

Kent E Pryor

Debra A Ryan

James L Paul

Adin L Stautzenberger

William J Wells, Iii

Shannon L Dugan

Jerry A Broussard

Ioan Nicolau

Leslie E Wade

Milo C Pass

Wendell L Pieper

Robert J Koprowski

Disclosed is the use of a Raney cobalt catalyst in the hydrogenation process for the production of n-butanol. A process for the production of purified n-butanol comprising contacting in a hydrogenation zone n-butyraldehyde and hydrogen with an active porous cobalt catalyst under hydrogenation conditions of temperature and pressure for the production of alcohols from aldehydes, either in the substantial absence of water, or in the presence of water in an amount up to about 6 wt % based on the weight of the liquid hydrogenation reaction product to produce said reaction product comprising n-butanol, and purifying said reaction product by fractional distillation in the presence of about 0.01 to about 6 wt % of water, based on the total weight of feed to the fractionating column.

Process for the production of n-butanol

A process for the production of purified n-propanol comprising contacting in a hydrogenation zone propionaldehyde and hydrogen with an active porous cobalt catalyst under hydrogenation conditions of temperature and pressure for the production of alcohols from aldehydes, either in the substantial absence of water, or in the presence of water in an amount up to about 3 wt % based on the weight of the liquid hydrogenation reaction product, to produce said reaction product comprising n-propanol, and purifying said reaction product by fractional distillation in the substantial absence of water, or in the presence of water in an amount up to about 3 wt % based on the total weight of feed to the fractionating column.

Process for the production of n-propanol

Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbomane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.

Synthesis of and hydroformylation with fluoro-substituted bidentate

Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.

Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1.sup.' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.

In a primary process for hydroformylating olefins in the presence of a rhodium-containing catalyst solution to produce aldehydes and a gaseous effluent comprising unreacted olefin is vented, the improvement which comprises employing the effluent as a reactant feed for a coupled secondary hydroformylation process conducted jointly therewith in which the catalyst solution is cycled back and forth between the primary and secondary hydroformylation processes.

Coupled secondary oxo reaction system

1,3-Propanediol is manufactured by the hydration of acrolein in an aqueous solution over a fully hydrated, alumina-bound zeolite with a pore size &gt;5 angstroms to form 3-hydroxypropanal and hydrogenation of the 3-hydroxypropanal typically in an aqueous solution in the presence of a nickel catalyst.

Method for the manufacture of 1,3-propanediol

This invention pertains to the addition of an alkyl alcohol to an alkyl acrylate to form alkyl 3-alkoxy propanoate catalyzed by a strong acid catalyst. The process has sepcific application in the addition of ethanol to ethyl acrylate to form ethyl 3-ethoxy propanoate.

Production of ethyl 3-ethoxypropanoate by acid catalyzed addition of

Aqueous formaldehyde is hydroformylated to glycol aldehyde in the presence of a rhodium-phosphine ligand complex catalyst in which the phosphine ligand is a trialkyl- or tricycloalkylphosphine and has a specified cone angle. A preferred phosphine ligand is tricyclohexylphosphine.

Hydroformylation of aqueous formaldehyde using a

An improved process for hydroformylating an ethylenically-unsaturated compound to form an aldehyde derivative thereof in the presence of rhodium hydridocarbonyl in complex combination with an organic ligand, characterized by employing as said organic ligand a compound having two phosphino moieties, one being of the formula: ##STR1## and the other being of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.1 ', and R.sub.2 ' are organic radicals at least one of which contains an electronegative substituent moiety. The presence of the electronegative substituent in the ligand leads to an increased ratio of linear aldehyde to branched-chain aldehyde in the hydroformylation reaction product.

Hydroformylation process employing rhodium-based catalysts comprising

An organo metallic complex catalyst, useful in the hydroformylation of an olefin, e.g., an alkene, to yield an aldehyde product in which the normal aldehyde isomer predominates over branch-chain isomers, which has the structure: ##STR1## wherein capital M is a Group VIII metal (preferably rhodium); Q is phosphorus, arsenic, or antimony (preferably phosphorus); and R is phenyl or a lower alkyl group. In the process employing the new catalytic complex is not necessary to employ an excess of any ligand, and moderate reaction conditions are adequate. The catalyst can be prepared ex situ or in situ from a suitable source of rhodium or the Group VIII metal and a suitable derivative of ferrocene.

Hydroformylation catalysts

Olefins are converted to aldehydes and/or alcohols having one more carbon atom than the olefin by reacting the olefin with carbon monoxide and hydrogen in the presence of an in situ formed catalytic complex of a Group VIII metal, carbon monoxide and a trivalent ligand, the metal being introduced into the reaction zone in the form of a solution of a water-soluble inorganic salt dissolved in a solvent comprised of at least 40% by volume of a polyalkylene glycol, the polyalkylene glycol acting as a coupling agent preventing precipitation of the metal prior to formation of the catalyst complex.

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Corpus Christi, TX, United States of America

Jerry D Unruh