Monsanto Company

Gary J Lynch

David R Dyroff

Victor D Papanu

Roger L Kidwell

Chen-Hsyong Yang

The disclosed process is employed to recover phenol from aqueous solutions produced by distillation of the product of a process for producing a phenyl ester by the reaction of a carboxylic acid and phenol. Purified phenyl ester is employed to extract phenol from the aqueous solution. The extract is combined with raw product for recovery of the phenol and phenyl ester. In a preferred embodiment the process for producing the phenyl ester is continuous and the extract containing phenol and phenyl ester are fed to the dewatered ester stream for product recovery.

Recovery of phenol from aqueous solution

The alkali metal, ammonium and alkanol amine salts of acetal carboxylate polymers are known to be stable detergent builders and chelating agents which depolymerize in acid media making the polymer fragments more readily biodegradable in waste streams. Now, according to the present invention, the hydrolytic stability of an acetal carboxylate polymer can be controlled by bringing together under polymerization conditions an ester of glyoxylic acid and a polymerization initiator and adding to the termini of the resulting polymer end groups having substituents which are selected to be more electron withdrawing as the desired hydrolytic stability increases.

Selectively controlling the hydrolytic stability of acetal carboxylate

The alkali metal, ammonium and alkanol amine salts of polymeric acetal carboxylates are stable detergent builders under laundry use conditions, but depolymerize in acid media, making the polymer fragments more readily biodegradable in waste streams. Now, in the improved process of the present invention for preparing an acetal carboxylate polymer wherein an ester of glyoxylic acid and a polymerization initiator are brought together under polymerization conditions and a chemically stable end group is added to the termini of the resulting polymer to stabilize the polymer against rapid depolymerization in alkaline solution, the improvement comprises adding to the resulting polymer a sufficient amount of an alkali metal hydride, preferably sodium hydride, and a dialkyl sulfate having 1 to about 20 carbon atoms in each alkyl group, preferably dimethyl sulfate, to add to the termini of the resulting polymer an alkyl group derived from the dialkyl sulfate.

Process for stabilizing acetal carboxylate polymers using dialkyl sulfate

The alkali metal, ammonium and alkanol amine salts of polymeric acetal carboxylates are stable detergent builders and chelating agents. Now, in the improved process of the present invention for preparing an acetal carboxylate polymer wherein a glyoxylate ester and a polymerization initiator are brought together under polymerization conditions and a chemically stable end group is added to the termini of the resulting polymer to stabilize the polymer against rapid depolymerization in alkaline solution, the improvement comprises contacting the resulting polymer in the presence of an acid catalyst with a sufficient amount of an acetal having 3 to 20 carbon atoms to stabilize the resulting polymer against rapid depolymerization in alkaline solution, and an agent to remove liberated alcohol.

Stabilization of polymeric acetal carboxylates using an acetal

A process which comprises contacting a zirconium compound having the formula ##STR1## wherein Cp is a .pi.-cyclopentadienyl radical and each Cp can be the same or different,

Preparation of acyl chlorides

Zirconium halohydrides having the formula ##STR1## WHEREIN R is a .pi.-cyclopentadienyl radical are prepared by reacting a dihalide having the formula ##STR2## WITH MOLECULAR HYDROGEN IN THE PRESENCE OF AN UNREACTED Group Ia metal in a solvent for the dihalide.

Zirconium halohydride preparation

Terminal olefin is prepared by bringing together (1) a compound having the formula ##STR1## wherein Cp is a .pi.-cyclopentadienyl radical, R is terminal alkyl and X is an essentially non-interfering monovalent entity, and (2) a mono-olefin having a carbon skeleton different from that of R under reaction conditions to displace R from (1) by (2). This process is especially useful in isomerization of internal olefins to the corresponding terminal olefins.

Growing community of inventors

St. Louis, MO, United States of America

Gary J Lynch