Toyo Soda Manufacturing Co., Ltd.

Sagami Chemical Research Center

Ajinomoto Co., Ltd.

(zaidanhojin) Sagami Chemical Research Center

Toyo Soda Mfg. Co., Ltd.

Keiichi Kihara

Yuji Nonaka

Kiyotaka Oyama

Kanzi Katsuragawa

Shigeaki Nishimura

Tatsuo Hattori

Hanzo Tamabayashi

Yoshikazu Isowa

Muneki Ohmori

Tetsuya Ichikawa

Kaoru Mori

Heijiro Satoh

Yasuhiro Oda

Teruhisa Sakamoto

Kazuhiko Sekizawa

Masashige Kubo

Toshio Hironaka

Hideo Sakka

Tetsuo Tanaka

Shigeo Nakamura

Isao Ono

Tsutomu Hashimoto

Taketoshi Nagahama

Addition compounds have the formula ##STR1## wherein R.sub.1 represents an aliphatic oxycarbonyl group, benzyloxycarbonyl group which can have nuclear substituents or benzoyl, aromatic sulfonyl or aromatic sulfinyl group; R.sub.2 represents methyl, isopropyl, isobutyl, isoamyl or benzyl group; R.sub.3 represents a lower alkoxyl, benzyloxy or benzhydryloxy group and n represents 1 or 2. The addition compounds are produced by reacting an N-substituted monoaminodicarboxylic acid having the formula ##STR2## with an amino carboxlic acid ester having the formula in an aqueous medium in the presence of a protease and reacting the resulting dipeptide ester with the amino carboxylic acid ester and separating the addition compound. The addition compounds can be decomposed into the constituent dipeptide esters and amino acid esters by the action of an acid.

Addition compound of dipeptide derivative and amino acid derivative

A method for purifying an .alpha.-L-aspartyl-L- phenylalanine lower alkyl ester containing impurities. The .alpha.-L-aspartyl-L-phenylalanine lower alkyl ester is brought into contact with a Cl-type anion exchange resin in an aqueous medium to have the impurities adsorbed by the anion exchange resin. The impurities contained in the .alpha.-L-aspartyl-L-phenylalanine lower ester, particularly diketopiperazine and .alpha.-L-aspartyl-L-phenylalanine are selectively and easily removed. The desired matter thus can be easily recovered and disposal of waste liquid, etc. can also be carried out without difficulty.

Method for purifying .alpha.- L-aspartyl-L-phenylalanine lower alkyl

A process for brominating m-phenoxytoluene with a polyhaloethane having the formula ##STR1## wherein W and Z respectively represent Cl or Br and X and Y respectively represent Cl, Br or H in a liquid phase.

Bromination of side chain of m-phenoxytoluene

An improvement in a method for manufacturing dipeptides from an N-substituted aspartic acid and a phenylalanine lower alkyl ester. The two starting materials are allowed to react with each other in the presence of an immobilized metallo-proteinase in an organic solvent immiscible with water. The enzyme can be recovered for reuse thereof. The loss of materials due to the hydrolysis of the phenylalanine lower alkyl ester is reduced, so that use of the phenylalanine lower alkyl ester in a nearly stoichiometric quantity suffices for the reaction to ensure an improved yield and reduction in cost of industrial production.

Method for manufacturing dipeptides

Addition compounds having the formula ##STR1## wherein R.sub.1 represents an aliphatic oxycarbonyl group, benzyloxycarbonyl group which can have nuclear substituents, or benzoyl, aromatic sulfonyl or aromatic sulfinyl group; R.sub.2 represents methyl, isopropyl, isobutyl, isoamyl or benzyl group; R.sub.3 represents a lower alkoxyl, benzyloxy or benzhydryloxy group and n represents 1 or 2 are produced by reacting an N-substituted monoaminodicarboxylic acid having the formula ##STR2## with an amino carboxylic acid ester having the formula ##STR3## in the presence of a protease.

Methacrolein is produced by a vapor phase oxidation of isobutylene or tertiary butanol in the presence of a complex oxide catalyst having the formula

Process for producing methacrolein

Methacrylic acid is produced by the vapor phase oxidation of methacrolein in the presence of a complex oxide catalyst having the formula:

Process for producing methacrylic acid

Addition compounds having the formula ##STR1## wherein R.sub.1 represents an aliphatic oxycarbonyl group, benzyloxycarbonyl group which can have nuclear substituents, or benzoyl, aromatic sulfonyl or aromatic sulfinyl group; R.sub.2 represents methyl, isopropyl, isobutyl, isoamyl or benzyl group; R.sub.3 represents a lower alkoxyl, benzyloxy or benzhydryloxy group and n represents 1 or 2 together with methods for preparing (I) and for decomposing (I) into the constituent dipeptide esters and amino acid esters.

Ammonium p-styrenesulfonate is produced in a process which comprises reacting an amine having more than 7 carbon atoms and a mineral acid with an alkali metal p-styrenesulfonate in an aqueous media to produce an amine salt of p-styrenesulfonic acid and then reacting ammonia with said amine salt.

Process for producing ammonium p-styrenesulfonate

An alkali metal styrenesulfonate is produced by extracting from an aqueous solution by contacting an aqueous solution containing an alkali metal halide and an alkali metal styrenesulfonate with an organic solvent containing a protonic acid salt of an amine of more than 7 carbon atoms as the extracting reagent, and then back-extracting the styrenesulfonic acid anions with an aqueous solution of an alkali metal hydroxide.

Process for producing alkali metal styrenesulfonate

A process for producing an ammonium p-styrenesulfonate or polymer thereof which comprises

Process for producing ammonium aromatic sulfonate

Conjugated dienes containing a cyano group having the formula ##EQU1## wherein R.sub.1 and R.sub.2 represent hydrogen atom, an alkyl group or a phenyl group are produced by dehydrating 2-cyano-3-hydroxy-1-olefins in the presence of an alkaline catalyst while continually removing the product being formed from the reaction system.

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Shinnanyo, Japan

Keiichi Kihara