Seitetsu Kagaku Co., Ltd.

Sumitomo Metal Industries, Inc.

Kunioki Kato

Masao Kawamura

Hiroshi Goda

Makoto Sato

Akira Onoe

Tsuyoshi Morishita

Tadaaki Nishi

Hiroshi Mizokami

Kazuhiro Hamatani

Tadashi Kanazawa

Kiyoshi Sawada

Tomiharu Amitani

Michio Suzuki

Tetsuzo Arai

Masato Yoshikawa

Koichi Fujiki

Hirokazu Kagano

Masahide Takahashi

Kazuyuki Nakayama

Yasuhiko Okamoto

Akio Nakatsuka

Kohji Noji

Miyoshi Koyama

In a process of producing high purity bis(4-hydroxyphenyl)sulfides which comprises reacting phenols with sulfur dichloride in an organic solvent, the improvement comprising: reacting the phenols with sulfur dichloride in a nonpolar organic solvent; removing partly or wholly the nonpolar organic solvent after the reaction; adding a polar organic solvent to the reaction mixture to dissolve the reaction mixture therein at elevated temperatures; and crystallizing out the high purity bis(4-hydroxyphenyl)sulfides. There is further provided a high performance heat-sensitive recording material which comprises high purity bis(4-hydroxy-3-methylphenyl)sulfide thus prepared and having a melting point in the range of from 123.9.degree. C. to 124.9.degree. C. as a developer and a fluoran compound as a color former.

Process of producing high purity bis(4-hydroxyphenyl)sulfides and

In a process of producing high purity bis(4-hydroxyphenyl) sulfides which comprises reacting phenols with sulfur dichloride in organic solvents, the improvement comprising: reacting the phenols with sulfur dichloride in nonpolar organic solvents; removing partly or wholly the nonpolar organic solvents after the reaction; adding polar organic solvents to the reaction mixture to dissolve the reaction mixture therein at elevated temperatures; and crystallizing out the high purity bis(4-hydroxyphenyl)sulfides. There is further provided a high performance heat-sensitive recording material which comprises high purity bis(4-hydroxy-3-methylphenyl)sulfide thus prepared and having a melting point in the range of from 123.9.degree. C. to 124.9.degree. C. as a developer and a fluoran compound as a color former.

Heat-sensitive recording materials containing high purity

Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are susceptible to electrophilic substitution reactions, and the acetylation, nitration, sulfonation and halogenation of the compounds provide 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-nitro-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acid and 5-halo-2-(.alpha.-alkoxyimino)ethylthiophenes, respectively. The hydrolysis of 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes readily provides a known compound, 2,5-diacetylthiophene which is an important intermediate for the production of medicines, whereas the haloform reaction provides novel compounds, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenecarboxylic acids, the hydrolysis of which compounds readily provides a known compound, 5-acetyl-2-thiophenecarboxylic acids, an important intermediate for the production of medicines. The hydrolysis of 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acids and their salts provide novel 5-acetyl-2-thiophenesulfonic acid and its salts, respectively. Novel compounds, 2-(.alpha.-alkoxyimino)ethylithiophenes are obtained either by 0-alkylation of 2-acetylthiophene oxime or by directly reacting 2-acetylthiophene with an 0-alkylhydroxylamine.

Novel thiophene derivatives and methods for producing the same

Process for preparing 2-alkyl-5-haloacetylbenzenesulfonamide represented by the general formula (1), ##STR1## (wherein R.sup.1 is an alkyl group having 1 to 5 carbon atoms; and X is a chlorine atom, bromine atom or iodine atom), characterized by halogenating a 5-acetyl-2-alkylbenzenesulfonamide represented by the general formula (2), ##STR2## (wherein R.sup.1 is the same as defined above) in a lower alcohol represented by the general formula (3),

Salt of 5-acetyl-2-alkylbenzenesulfonic acid

Process for preparing N,N-dialkylaniline salt of 5-acetyl-2-alkylbenzene

A method of producing alkali metal benzenesulfinates having the general formula of ##STR1## wherein M represents Na or K, which comprises: reacting nitrophenylphenyl sulfones having the general formula of ##STR2## wherein n is an integer of 1 or 2, with alkali metal thiophenolates having the general formula of ##STR3## in solvents. The reaction produces also nitrophenylphenyl sulfides as by-products in equimolar amounts to the alkali metal benzenesulfinates, and the oxidation of the sulfides provides the starting nitrophenylphenyl sulfones. A method of producing the nitrophenylphenyl sulfones is also provided wherein the sulfides are oxidized with hydrogen peroxide in the presence both of water-soluble tungstates or molybdates and of phase transfer catalysts in a two-phase heterogeneous solvent.

Method of producing alkali metal benzenesulfinates

Novel compounds, 4-tert.-butyl-1,2-benzenedithiol and bis(4-tert.-butyl-1,2-dithiophenolate) metal complexes having the general formula of ##STR1## wherein M represents a trivalent transition metal, and A represents a quarternary ammonium are provided. The novel benzenedithiol is produced by reacting 4-tert.-butylbenzenethiol or di(4-tert.-butylphenyl)disulfide with sulfur monochloride in the presence of iodine or a Lewis acid in a solvent, and then reducing the resultant product with a metal selected from the group consisting of zinc, tin, iron and aluminum in the presence of an acid. The novel Cu, Co and Ni complexes are produced by reacting the benzenedithiol with a salt of the corresponding divalent transition metal in the presence of an alkoxide metal or a hydride metal and a quarternary ammonium salt in a solvent under an oxidative atmosphere. The complexes strongly absorb rays in the region of ultraviolet, visible or near infrared, and are useful intermediates for the production of optical information recording media.

4-tert.-butyl-1,2-benzenedithiol, complex compounds derived therefrom,

Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are susceptible to electrophilic substitution reactions, and the acetylation, nitration, sulfonation and halogenation of the compounds provide 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-nitro-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acid and 5-halo-2-(.alpha.-alkoxyimino)ethylthiophenes, respectively. The hydrolysis of 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes readily provides a known compound, 2,5-diacetylthiophene which is an important intermediate for the production of medicines, whereas the haloform reaction provides novel compounds, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenecarboxylic acids, the hydrolysis of which compounds readily provides a known compound, 5-acetyl-2-thiophenecarboxylic acids, an important intermediate for the production of medicines. The hydrolysis of 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acids and their salts provide novel 5-acetyl-2-thiophenesulfonic acid and its salts, respectively. Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are obtained either by 0-alkylation of 2-acetylthiophene oxime or by directly reacting 2-acetylthiophene with an 0-alkylhydroxylamine.

Thiophene derivatives and methods for producing the same

A process for producing p-hydroxybenzaldehyde through p-aminobenzaldehyde from p-nitrotoluene, comprising reacting p-nitrotoluene with sodium polysulphide in an alcohol-alkali aqueous solution mixed solvent in the presence or absence of an aprotic polar compound to produce p-aminobenzaldehyde, diazotizing the p-aminobenzaldehyde and then hydrolyzing the diazotized p-aminobenzaldehyde to produce p-hydroxybenzaldehyde.

Process for producing p-hydroxybenzaldehyde

A coating composite containing sulfochlorinated polyolefin having a sulfur content ranging from 0.2 to 2.5% by weight and a chlorine content ranging from 18 to 37% by weight is applied directly as an adhesive layer or is applied on one surface of a thermoplastic resin base to be contacted with a metal surface, which resin base is coated on the metal surface. When the coating composite is pressed thereafter under a pressure, a coating on the metal surface with excellent adhesion, water and impact resistances is provided.

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Hyogo, Japan

Kunioki Kato