Thermal Dimerization of Alkali Acrylate/3-Methyl-3-butenoate and Alkali Methacrylate/3-Methyl-3-butenoate Binary Systems in the Solid State

• Fumihiko Akutsu

  Department of Applied Chemistry, Faculty of Engineering, Chiba UniversityYayoi-cho 1-33, Inage-ku, Chiba 263

• Mari Inoki

  Department of Applied Chemistry, Faculty of Engineering, Chiba UniversityYayoi-cho 1-33, Inage-ku, Chiba 263

• Nozomu Nishimura

  Department of Applied Chemistry, Faculty of Engineering, Chiba UniversityYayoi-cho 1-33, Inage-ku, Chiba 263

• Yoshio Kasashima

  Department of Applied Chemistry, Faculty of Engineering, Chiba UniversityYayoi-cho 1-33, Inage-ku, Chiba 263

• Kiyoshi Naruchi

  Department of Applied Chemistry, Faculty of Engineering, Chiba UniversityYayoi-cho 1-33, Inage-ku, Chiba 263

抄録

The thermal reaction in the solid state of binary salts, obtained from an equimolar mixture solution, of lithium 3-methyl-3-butenoate/methacrylate (3-MBA/MA) or potassium 3-MBA/MA, after esterification, produced mainly dimethyl (Z)-3,6-dimethyl-2-heptenedioate as a novel cross-coupled dimer. The cross-coupled dimer was obtained from the potassium salts in 35.5% yield upon heating at 230 °C for 2 h. Similary, a methyl ester of the cross-coupled dimer, dimethyl (Z)-3-methyl-2-heptenedioate, was given from sodium 3-methyl-3-butenoate/acrylate (3-MBA/AA) or potassium 3-MBA/AA after esterification. The cross-coupled dimer was obtained from potassium 3-MBA/AA in 57.5% yield upon heating at 230 °C for 2 h. The X-ray diffraction pattern of potassium 3-MBA/MA or potassium 3-MBA/AA indicates the formation of a new phase, that is different from that of the individual salts. The crystal system of K–(3-MBA/AA) was transformed to a more stable state by initial heating for 20 min. The selective cross-coupled dimerization was caused by the new phase of binary salts and maintaining the crystal state of the reaction system by the formation of solid-solution crystals.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 69 (4), 1087-1091, 1996-04-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360565169057664640
• NII論文ID: 130004149522
• DOI: 10.1246/bcsj.69.1087
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/69/4/1087/56245230/bcsj.69.1087.pdf
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