The process of synthesis of 1, 7-dichloroheptene-3 and 1, 9-dichlorononene-4 by the selective dehydrochlorination reaction of secondary chlorine of 1, 4, 7-trichloroheptane and 1, 4, 9-trichlorononane was investigated. As the fixed catalyst for vapor phase dehydrochlorination reaction of these trichlorides, pumice, granulated activated carbon and those containing various metal chlorides were investigated. The result indicated that the catalyst of granulated activated carbon containing 10% barium chloride was found to be best. Studies on reaction temperatures, flow rate of carrier gas and rate of feeding of raw material indicated that the best condition was found to be 3.44 l of caltalyst, the feeding rate of raw material at 1 kg/hr, the flow rate of nitrogen gas at 120 l/hr at 200°C with space velocity of 0.24 l/hr, and this gave 1, 7-dichloroheptene-3 with 87% yield at 93-95% conversion (93% yield from converted raw material). However, there was a small amount of 1-chloroheptadiene-4, 6 (4-5%) and 1, 4-dichloroheptene-6 (0.7%) as the by-products due to excessive dehydrochlorination. There was no formation of 1, 7-dichloroheptene-3 by the reaction of hydrated lime or sodium hydroxide with 1, 4, 7-trichloroheptane. However, heating of 1, 4, 7-trichloroheptane and 1, 4, 9-trichlorononane in liquid phase without catalyst at 220-260°C or heating in vacuo at 115-120°C in the presence of zinc chloride gave 1, 7-dichloroheptene-3 and1, 9-dichlorononene-4, respectively, but the velocity of dehydrochlorination reaction was much slower than that of using vapor phase reaction under fixed catalyst. Therefore this method is not practical. Dehydrochlorination reaction of 1, 4, 7-trichloroheptane and 1, 4, 9-trichlorononane in liquid phase without catalyst proceeded the first order reactiion. Apparent activation energy of the former was 22.7 kcal/mol and that of latter was 31.4 kcal/mol.

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Ethyl acetate, ethyl n-butyrate, n-butyl acetate and n-butyl n-butyrate were synthesized by the crossed Tischtschenko reaction between acetaldehyde and n-butyraldehyde with metal alkoxide as the catalyst. An increase in the ratio of acetaldehyde in the raw material showed a tendency to retard the formation of n-butyrate. It was found that the formation of n-butyl acetate was increased by the addition of a small amount of mercuric chloride as an accelerator for the reaction. The formation of ethyl acetate was larger in carbon tetrachloride as a solvent. In this catalytic reaction, aldehyde coordinated with aluminium showed a tendency to turn into acid side of the esters formed. The yield of ester was 70-80% and the conversion was 60-70%.

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Wyler's wet method for synthesis of copper phthalocyanine was applied for synthesis of copper-Bz-aza (3, 4) phthalocyanine from cinchomeronic acid and phthalic anhydride, The ratios of raw materials were changed and the properties of products were investigated. This product in concentrated sulfuric acid was diluted with water and the pigments precipitated in various concentration of sulfuric acid were separated by filtration. The relation between ratios of raw materials, and the amount of separated pigments and its properties was investigated. A comparative test on a mixture of copper phthalocyanine and copper tetra (3, 4)-pyridinoporphyrazine indicated that the higher the numbers of pyridine ring in a phthalocyanine molecule the lower was the concentration of sulfuric acid required for precipitation.

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Allylic chlorides such as allylchloride, 3-chlorobutene-1 and 1-chlorobutene-2 have been shown to react with tert-butyl hypochlorite by a radical chlorination . Allylchloride and 3-chlorobutene-1 give 1, 3-dichloropropene and 1, 3-dichlorobutene-2 respectively as the major. On the other hand, 1-chlorobutene-2 gives various dichlorobutenes. Preparation of chloroprene starting from butadiene has been investigated in connection to this chlorination.

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Reactive dyes of halobenzene type containing two active halogen atoms were synthesized. Acid dyes of azo-, anthraquinone-and phthalocyanine type having amino group capable of acylation, were acylated with dihalonitrobenzenesulfonyl chloride (1) or (2), and reactive dyes of general formula (3) or (4) were obtained. (D=color component) These dyes combined with cellulose in the presence of alkali; and it was found that dyes of type (4) were more reactive than dyes of type (3), and dyes of type (3) and (4) were more reactive than corresponding dyes which contain only one active halogen atom. Accordingly, with these dyes dyeing could be carried out under mild condition, and it was considered that, by usual dyeing method these dyes react with cellulose by only one halogenatom.

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Reaction of maleic anhydride with monoethanolamine, monopropanolamine, or monoisopropanolamine yielded N-β-oxyethylmaleamic acid, N-γ-oxypropylmaleamic acid, or N-β-oxyisopropylmaleamic acid, respectively. Dehydration of these maleamic acids with acetic anhydride and sodium acetate, followed by esterification gave N-acetoxyethylmaleimide, N-acetoxypropylmaleimide, or Nacetoxyisopropylisomaleimide, respectively. Dehydration and cyclization of N-β-oxyethylmaleamic acid with a small amount of sulfuric acid gave N-β-oxyethylmaleimide. Similar dehydration and esterification of N, O-dimaleoylaminoethanol gave N-(methylmaleoyl)ethylmaleimide. All of the above products are new compounds. Maleimide derivative was synthesized as a monomer in order to obtain its polymer.

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