Allied Colloids Limited

Ciba Specialty Chemicals Corporation

Gerald P Benn

David Farrar

Peter Flesher

Seraj A Karolia

Liliana Craciun

Bernd Siebenhaar

George William Schriver

Urs Siegrist

John Dewing

Janet Catrine Doyle

William J Peer

Peter Stuart Littlewood

The invention is directed to a process for the preparation of &#x3b1;,&#x3b2;-unsaturated acids, esters and amides from &#x3b1;- or &#x3b2;-hydroxycarboxylic acids or esters or precursors in high yields and high selectivity. The &#x3b1;,&#x3b2;-unsaturated acids or esters are optionally prepared in the presence of specific dehydration and/or esterification catalysts. The &#x3b1;,&#x3b2;-unsaturated amides or substituted amides are prepared optionally in the presence of a dehydration and/or amidation catalyst. The source of &#x3b1;- or &#x3b2;-hydroxycarboxylic acids or precusor is preferably from a renewable resource. The precursor is defined herein.

Preparation of acrylic acid derivatives from &#x3b1;-  or &#x3b2;-hydroxy carboxylic acids

Synthesis of vinyl esters

When making an amide by hydrolysis of a nitrile in an aqueous medium containing a Raney copper or other black copper catalyst, the hydrolysis reaction can be improved if the catalyst has been contacted with an aqueous solution of a water soluble vanadium compound followed by thorough rinsing before introduction into the aqueous medium.

Catalysts and their use in the hydrolysis of nitriles

When making an a amide by hydrolysis of a nitrile in an aqueous medium containing a Raney copper catalyst, the yield of amide can be increased and the yield of impurities can be decreased by including vanadium metal in the catalyst. The vanadium may be present as Raney vanadium often as an alloy in the Raney copper.

2-acrylamido 2-methyl propane sulphonic acid and other acrylamido-alkane sulphonic acids are made by reacting a compound such as t-butanol, t-butyl acetate or t-butyl methyl ester with a sulphonating agent in the absence of water, and then with a nitrile and water.

Process for producing sulphonic acid

Process for hydrolyzing nitriles

A substantially anhydrous mixture of methanol with an organic compound with which it forms an azeotrope can be separated by dissolving into the mixture lithium chloride or other suitable salt that forms a complex with methanol so as to form a homogeneous mixture, adding an organic solvent that is miscible with the organic compound but immiscible with the complex and thereby forming a heterogeneous mixture, and separating the phases. The methanol can be recovered from one phase and the organic compound from the other. The organic compound may typically be methyl acrylate or methacrylate, the blend being, for instance, obtainable during the transesterification of methyl (meth)acrylate with an alcohol to form a higher boiling ester such as dimethylaminoethyl (meth)acrylate or 2-ethylhexyl acrylate.

Separation of methanol from mixtures containing it

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Bradford, United Kingdom

Gerald P Benn