Manganese(III) acetate-catalyzed synthesis of polyguaiacol

Sangpill Hwang, Yong Woo Lee, Chang-Ha Lee, Ik Sung Ahn

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Polyguaiacol was synthesized in the mixtures of water and various organic solvents using manganese(III) acetate as a new catalyst for radical polymerization and a biomimetic model for manganese peroxidase. Aqueous solutions of 30-70% (v/v) acetonitrile, 1,4-dioxane, and methanol were used as model solvent mixtures. The polymer yield in the methanol (<30%) solution was lower than that in the acetonitrile or 1,4-dioxane solution (60-90%). The average molecular weight of the polymer was also lowest in the methanol solution. Difference UV absorption spectroscopy analysis revealed that nonhydrated guaiacol clusters were found to be dominant in acetonitrile and 1,4-dioxane solutions, especially when the content of 1,4-dioxane was 50% (v/v) or higher. In the methanol solution, only the hydrated guaiacol clusters were observed. From the comparison of 1H NMR data for polyguaiacol and products of guaiacol oxidation by manganese(III) acetate, 3-(4-hydroxy-3- methoxy-phenyl)-5,3′-dimethoxy-4,4′-biphenol and a mixture of 5-(4-hydroxy-3-methoxyphenyl)-3,3′-dimethoxy-4,4′-biphenoquinone and 3-(4-hydroxy-3-methoxyphenyl)-5,3′-dimethoxy-4,4′-biphenoquinone were found to be the major structural units of polyguaiacol. Water molecule is not involved in the formation of these compounds. Therefore, the polymerization should take place readily not in methanol but in acetonitrile and 1,4-dioxane solutions.

Original languageEnglish
Pages (from-to)6009-6015
Number of pages7
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume46
Issue number18
DOIs
Publication statusPublished - 2008 Sep 15

Fingerprint

Manganese
Methanol
Guaiacol
Acetonitrile
manganese peroxidase
Polymers
Water
Biomimetics
Free radical polymerization
manganese(III) acetate dihydrate
Ultraviolet spectroscopy
Absorption spectroscopy
Organic solvents
Molecular weight
Polymerization
Nuclear magnetic resonance
1,4-dioxane
Oxidation
Catalysts
Molecules

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

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title = "Manganese(III) acetate-catalyzed synthesis of polyguaiacol",
abstract = "Polyguaiacol was synthesized in the mixtures of water and various organic solvents using manganese(III) acetate as a new catalyst for radical polymerization and a biomimetic model for manganese peroxidase. Aqueous solutions of 30-70{\%} (v/v) acetonitrile, 1,4-dioxane, and methanol were used as model solvent mixtures. The polymer yield in the methanol (<30{\%}) solution was lower than that in the acetonitrile or 1,4-dioxane solution (60-90{\%}). The average molecular weight of the polymer was also lowest in the methanol solution. Difference UV absorption spectroscopy analysis revealed that nonhydrated guaiacol clusters were found to be dominant in acetonitrile and 1,4-dioxane solutions, especially when the content of 1,4-dioxane was 50{\%} (v/v) or higher. In the methanol solution, only the hydrated guaiacol clusters were observed. From the comparison of 1H NMR data for polyguaiacol and products of guaiacol oxidation by manganese(III) acetate, 3-(4-hydroxy-3- methoxy-phenyl)-5,3′-dimethoxy-4,4′-biphenol and a mixture of 5-(4-hydroxy-3-methoxyphenyl)-3,3′-dimethoxy-4,4′-biphenoquinone and 3-(4-hydroxy-3-methoxyphenyl)-5,3′-dimethoxy-4,4′-biphenoquinone were found to be the major structural units of polyguaiacol. Water molecule is not involved in the formation of these compounds. Therefore, the polymerization should take place readily not in methanol but in acetonitrile and 1,4-dioxane solutions.",
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Manganese(III) acetate-catalyzed synthesis of polyguaiacol. / Hwang, Sangpill; Lee, Yong Woo; Lee, Chang-Ha; Ahn, Ik Sung.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 46, No. 18, 15.09.2008, p. 6009-6015.

Research output: Contribution to journalArticle

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AB - Polyguaiacol was synthesized in the mixtures of water and various organic solvents using manganese(III) acetate as a new catalyst for radical polymerization and a biomimetic model for manganese peroxidase. Aqueous solutions of 30-70% (v/v) acetonitrile, 1,4-dioxane, and methanol were used as model solvent mixtures. The polymer yield in the methanol (<30%) solution was lower than that in the acetonitrile or 1,4-dioxane solution (60-90%). The average molecular weight of the polymer was also lowest in the methanol solution. Difference UV absorption spectroscopy analysis revealed that nonhydrated guaiacol clusters were found to be dominant in acetonitrile and 1,4-dioxane solutions, especially when the content of 1,4-dioxane was 50% (v/v) or higher. In the methanol solution, only the hydrated guaiacol clusters were observed. From the comparison of 1H NMR data for polyguaiacol and products of guaiacol oxidation by manganese(III) acetate, 3-(4-hydroxy-3- methoxy-phenyl)-5,3′-dimethoxy-4,4′-biphenol and a mixture of 5-(4-hydroxy-3-methoxyphenyl)-3,3′-dimethoxy-4,4′-biphenoquinone and 3-(4-hydroxy-3-methoxyphenyl)-5,3′-dimethoxy-4,4′-biphenoquinone were found to be the major structural units of polyguaiacol. Water molecule is not involved in the formation of these compounds. Therefore, the polymerization should take place readily not in methanol but in acetonitrile and 1,4-dioxane solutions.

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