Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 20, Issue 5
Displaying 1-15 of 15 articles from this issue
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  • Recent Progress of Monoterpene Chemistry
    Tamon MATSUURA
    1962 Volume 20 Issue 5 Pages 415-425
    Published: May 01, 1962
    Released on J-STAGE: July 05, 2011
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.415
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  • Progress in Methane Chemistry
    Taiseki KUNUGI, Tomoya SAKAI
    1962 Volume 20 Issue 5 Pages 426-434
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.426
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  • Noticeable Patents of Recent Days
    Hiroshi NAKAMOTO
    1962 Volume 20 Issue 5 Pages 435-444
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.435
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  • Azo Dyes Containing -SO2NHCH2CH2NCH3RRGroup, CH3
    Koji MATSUI, Eizo KOBAYASHI, Kazuaki SUZUKI
    1962 Volume 20 Issue 5 Pages 445-452
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.445
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    By the reaction of p-acetaminobenzene- and 4-acetamino-1-naphthalenesulfonylethylenimide with secondary amines (diethylamine, diethanolamine, pipe ridine, and morpholine), corresponding sulfonyl-β-dialkylaminoethylamide, and by their hydrolysis (1) and (2) were obtained.(1) H2N SO2NHCH2CH2NRR and (2), H2N -SO2NHCH2CH2NRR Using (1) and (2) (quarternary base in the case of (2)), as diazo component, a series of azo dye were obtained by combination with some of aromatic tertiary amines (such as dimethylaniline, bis(β-hydroxyethyl)-aniline), and 3-methyl-1-phenylpyrazolone-5 etc. These dyes thus obtained were then converted into their quarternary salts by use of methyl sulfate. These dyes dyed Orlon type polyacrylonitrile fiber well to yellow- orange- red. The effect of R on the absorbability was not great and the dyes obtained by using those secondary amines, such as piperidine and morpholine, gave better absorbability than those of using diethylamine and diethanolamine. The absorbability of (1) type dyes were in the order of neutral > acidic >alkaline, and similar results were obtained in the case of (2) type compounds. The fastness against the light were not satisfactory and all remained to be 3-4th. grades, and the fastness against washing were about 4th. grade.
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  • Azo Dyes Containing -CH2CH(0H)CH2NRR Group. 1
    Koji MATSUI, Toshio SUNAGA, Kazuo KASAI
    1962 Volume 20 Issue 5 Pages 453-459
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.453
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    By the reaction of epichlorohydrin followed by diethylamine on aniline and α-naphthylamine, respectively, N-type C6H5NHCH2CH(0H)CH2N(C2H5)2 (1) (yield 56.65%), by 154-5°c/2 mm, and 1-C10H7NHCH2CH(OH)CH2N(C2H5)2 (2) yield 65.5%, bp 210°c/2 mm, were obtained. Also, by the reaction of epichlorohydrin on N-acetyl-m-aminophenol, followed by the reaction of diethylamine and hydrolysis of the product 0-type compound, m-H2NC6H4OCH2CH(OH)CH2N(C2H5)2 (3) (yield 49.5%, by 202-204°c/5 mm mp, 33-35deg;c) was obtained. A series of N-type azo dyes were synthesized by use of (1) and (2), respectively, as azo component, and various atom aticprimary amines having no carboxyl and sulf onyl group, such as p-nitroaniline, self anylamide and others, as diazo component. Also, O-type azo dyes were synthesized by use of (3) as diazo component, and dimethylaniline, β-naphthol, Naphthol AS, and 3-methyl-1-phenylpyrazolone-5 as azo components. A monoazo dye of 0-type was also prepared using (3) as azo component and Fast Red B base as diazo component; further diazotation of this dye and coupling it with dimethylaniline, Naphthol AS, etc. gave 0-type disazo dyes. The O- and N-type dyes thus obtained are soluble in dilute acetic acid, and have good dyeing property for Orlon type polyacrylonitrile fiber (Exlan L, Vonnel W and Cashmilon) with color ranges of yellow- orange- red- brown- purple. The quarternary ammonium salts of above dyes also showed similar characteristics.
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  • Synthesis of Arylmelamines. II.
    Synthesis of Diarylmelamines
    Itaru HONDA
    1962 Volume 20 Issue 5 Pages 460-465
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.460
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    Reaction of 2-amino-4, 6-dichloro-s-triazine and aromatic amines by a general method of refluxing for 2hrs, in water while neutralizing reaction solution yielded over 90% of diaryl-melamines in case of 4 kinds of liquid aromatic amines at room temperature. However, this method was unsuitable for reacton of 5 kinds of solid aromatic amines at room temperature. On the other hand, keeping of reacting solution weakly acidic and changing the time of reaction gave an improvement in yield over 90% in case of using of solid amines. Also it was found that an addition of neutralizing agent was not always necessary. Among 10 kinds of synthesized diarylmelamines, di-o-, -m-, and -p-toluylmelamines, mp 194-5°C, 139-40°C and 289-90°C, respectively, di-p-biphenylylmelamine, mp 278-9°C, di-β-naphthylmelamine, mp 217°C (8 hrs reaction), bis-p-acetylaminophenylmelamine, mp 300-1°C (10 min, reaction), and bis-p-aminophenylmelamine, mp 243-4°C (prepared by hydrolysis of the acetyl compound), are new compounds.
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  • Synthesis of Arylmelamines. III.
    Synthesis of Triarylmelamines,
    Itaru HONDA
    1962 Volume 20 Issue 5 Pages 466-472
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.466
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    Heating of a mixture of cyanuric chloride and aromatic amines in the molar ratio of 1 : 3 in benzene or acetone, removing of the solvent and heating of the residue for 15 min at 160-250°c yielded over 90% of triarylmelamines. Reaction by heating of aromatic amines other than aniline for long period of time at high temperature of 290-310°c induced the side reaction and good result could not be obtained. Of 10 kinds of synthesized triarylmelamines, the following 7 kinds of them are new compounds (triaryl group and mp given) : tri-o-toluyl, 219-20°c; tri-m-toluyl, 174-5°c; tris-p-ethoxyphenyl, 189-90°c; tris-p-chlorophenyl, 251-2°c; tri-p-biphenylyl, 282-3°c; tris-p-acetaminophenyl, 300-2°c (molar ratio 1: 5, heated 5min at 160°c with 74% yield), and tris-p-aminophenyl, 288-9°c (prepared by hydrolysis of its acetyl derivatives).
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  • The Studies on the Anthraquinone-azole Vat Dyes. IV
    The Syntheses and the Properties of the Blue Anthraquinone-mole Vat Dyes
    Mitsuhiko HIDA
    1962 Volume 20 Issue 5 Pages 473-477
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.473
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    Anthraquinone azole type vat dyes hawing anthraquinone(2:3)oxazole 1a, anthraquinone(1:2)oxazole 1b, anthraquinone(2:3)thiazole 1d, andanthraquinone (2:1)thiazole 1f in 2-position of 1, 4-diaminoanthraquinone were synthesized The dyes having anthraquinone(2:1)oxazole and anthraquinone (1:2) thiazole could not be obtained in pure form. As described in the preceeding report1, the order of λmax having absorpton in longer wave length side than 1, 4-diaminoanthra, uinone by the deep coloring action of nthraquinone-azole ring was in order of (1f)>(1d)>(1b)>(1a) and each of them had the same double head as in 1, 4-diaminoanthraquine. In these dyes, the amino group in 1-position is protected by the hydrogen bonding but the fasthess against chlorine is extremely weak due to the presence of amino group in 4-position. However, thedye having good fastness againstchlorine is obtained by benzoylation of amino group in 4-position.
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  • Studies on Anyl and Acyl derivatives of Sulf anilamides. II
    Synthesis of N4-(2-carboxybenzyliden) derivatives of Sulf anilamides
    Yuji KAWASHIMA
    1962 Volume 20 Issue 5 Pages 478-481
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.478
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    Sulfisoxazole condensed easily with benzaldehyde and gave N4-benzylidene derivative but N4-benzylidende derivatives of sulfadimethoxine, sulfadimetine and sulfamethazine could not be obtained. For synthetic and pharmaceutical point of view, 10 kinds of representative sulfa drugs in sulfanilamides, such as sulfanilamide, N1-acetylsulfanilamide, sulf athiazole, self isoxazole, sulfadiazine, sulf amerazine, sulfamethazine, self adimetine, sulfadimethoxine, and N1-acetylsulf isoxazole, were chosen. These were condensed with o-phthalaldehydic acid and corresponding N4-(2-carboxybenzylidene) derivatives were obtained in crystalline form. Since N4-(2-carboxybenzylidene) sulfisoxazole is tasteless, it is advantageous for oral administration to infants. Its decomposition in the body is confirmed from estimation of its concentration in blood and maintains sufficient concentration of therapeutic value.
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  • On the Production of Perchloroethylene and Carbon tetrachloride by Chlorinolysis of Propylene.
    Ryoma TANAKA
    1962 Volume 20 Issue 5 Pages 482-494
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.482
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    Conditions for reaction of formation of carbon tetrachloride and perchloroethylene by the thermal chlorinolysis of propylene have been clarified. A reaction vessel which forms no carbon is made at first, then the effects of molar ratios of chlorine and propylene, the temperature and the time for staying in vessel have been investigated. The mechanism of formation of by-product hexachlorobenzene and the catalyst for chlorinolysis of high boiling fractions of partially chlorinated hydrocarbon has been investigated and its effect was confirmed.
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  • On the Dispersed Naphthoquinone-imine Dyes
    Akira INOUE, Yasuo YOSHIOKA., Nobuhiko KUROKI, Kenzo KONISHI
    1962 Volume 20 Issue 5 Pages 495-500
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.495
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    Syntheses of 22 kinds of Celliton Fast Green 3 BS and its homologs, and 2 kinds of bromine derivatives of naphthazarin intermediate have been made and their dyeing properties, especially that of gas fading, have been investigated. The dye-ability of these compounds was better for Tetlon than for acetate but the gas fading was not satisfactory except for bromine derivatives of naphthazarin intermediate. Sublimation tests on Tetlon were generally good.
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  • Studies on Aromatic Carboxylic Acids. II
    Synthesis of 2, 6-naphthalenedicarboxylic acid by Henkel process.
    Junzo YAMASHITA, Keisuke ENOMOTO, Hiroshi EBISAWA, Shimpachiro KATO
    1962 Volume 20 Issue 5 Pages 501-506
    Published: May 01, 1962
    Released on J-STAGE: March 01, 2011
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.501
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    Synthesis of 2, 6-naphthalenedicarboxylic acid (1) by Henkel process was studied. Thermal isomerization of potassium naphthalate with 2-16 mo1% Cd catalyst was carried out in the temperature range 300-420°c in CO2 atmosphere. With 5 mol % CdI2 under 50 atm CO2 pressure, the yield of (1) reached maximum 65% at 340°c. The yield of (1) was increased with the increasing amount of catalyst, but the difference of catalytic activities of CdI2, CdCI2, and CdBr2 was not observed. The yield of (1) was increased under high CO2 pressure enormously, sugesting the close interaction of CO2 with the reactant. In the thermal disproportionation of potassium naphthoates, better yield of (1) was obtained in the case of α-naphthoate than in the case of β-naphthoate. Mixed naphthoates gave intermediate yield of (1).
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  • The Chemical Structure of Synthetic Lubricating Oils
    Sumio MATSUDA
    1962 Volume 20 Issue 5 Pages 507-511
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.507
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  • [title in Japanese]
    Hideo YAGUCHI
    1962 Volume 20 Issue 5 Pages 512-513
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.512
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  • [title in Japanese]
    Tunemasa OYAMA
    1962 Volume 20 Issue 5 Pages 514-516
    Published: May 01, 1962
    Released on J-STAGE: June 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.20.514
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