The Dow Chemical Company

Peter W Owen

Donald A Tomalia

Mark E Kaiser

William Dowd

James W Lalk

Gerald C Kolb

James W Sanner

Thomas T Chiu

Harold H Roth

Zita K Harmon

Method for preparing 2-alkenyl-2-oxazolines

Residual amounts of water and color-causing impurities can be removed from a 2-oxazoline compound by introducing from 0.01 to 25 weight percent of a dialkyl hydrogen phosphite or a halosilane compound to the 2-oxazoline and then distilling the oxazoline. For example, 0.5 weight percent of bis(2-ethylhexyl)hydrogen phosphite was introduced into 100 grams of 2-ethyl-2-oxazoline containing 1000 parts per million (ppm) of water and the mixture was then distilled to yield 2-ethyl-2-oxazoline containing less than 10 ppm of water.

Purification of 2-oxazolines

N-(haloalkyl)sulfonamides represented by the formula ##STR1## wherein R.sub.1 is a C.sub.1 -C.sub.20 aryl, alkaryl, aralkyl or alkyl group; R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen or methyl groups; n is the integer 0 or 1 and X is a chloro, bromo or iodo group, are prepared by reacting an N-(haloalkyl)sulfonyl imide with a C.sub.1 -C.sub.6 alkanol.

Process for the preparation of N-(haloalkyl)sulfonamide

An imidazoline modified styrene-acrylonitrile polymer composition which is substantially insoluble in aqueous media at about pH 6 or more but swellable or soluble at pH 3 or less is employed as a coating for nutrient or therapeutic substances for administration to ruminants. The substances thus are rendered resistant to attack and breakdown in the rumen yet remain susceptible to release and digestion within the abomasum or small intestine of the animal.

Coated nutrients and medicaments for veterinary use

N-(2-mercaptoethyl)alkanamides are produced by reacting hydrogen sulfide with 2-H-2-oxazolines or 2-alkyl-2-oxazolines. For example, N-(2-mercaptoethyl)acetamide was prepared in excellent yields by incrementally adding 2-methyl-2-oxazoline to a stirred solution of hydrogen sulfide in methanol under autogeneous pressure at about 100.degree. C.

N-(2-mercapto-ethyl)alkanamides from H.sub.2 S and 2-H-2-oxazolines or

N-(2-alkoxyethyl)alkanamides, such as N-(2-ethoxyethyl)ethanamide and N-(2-methoxyethyl)propanamide, are prepared by reacting a 2-oxazoline with methanol or ethanol in the presence of a strong base, such as sodium methoxide. Subsequent hydrolysis of such amides provides a convenient means for obtaining 2-alkoxyethyl amines.

Preparation of N-(2-alkoxyethyl)alkanamides and 2-alkoxyethyl amines

The reaction of 2-oxazolines with 1,2- or 1,3-alkylenediamines to form 2-imidazolines or 1,4,5,6-tetrahydropyrimidines is catalyzed by Lewis acids.

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Peter W Owen