Green Polymerization of Phenol in Ionic Liquids

被引：43

作者：

Ogoshi, Tomoki ^{[1
]}

Onodera, Takeshi ^{[1
]}

Yamagishi, Tada-aki ^{[1
]}

Nakamoto, Yoshiaki ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan

来源：

MACROMOLECULES | 2008年 / 41卷 / 22期

关键词：

D O I：

10.1021/ma801921e

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Polymerization of phenol with paraformaldehyde and catalytic sulfuric acid was carried out in room temperature ionic liquids based on imidazolium salts. The properties of ionic liquids were systematically varied by employing six different anions such as chloride, bromide, iodide, tetrafluoroborate, trifluoromethanesulfonate and hexafluorophosphate. In case of hydrophilic ionic liquids having chloride or bromide anion, phenol polymers with low molecular weight and narrow polydispersity were obtained. In contrast, using hydrophobic ionic liquids such as tetrafluoroborate and trifluoromethanesulforate anions, high molecular weight phenol polymers were prepared. It is because interaction of the hydrophilic ionic liquids with phenol is stronger than that of the hydrophobic ionic liquids. The interaction between phenol and ionic liquids was investigated by H-1 NMR measurements. Moreover, by using Bronsted acid ionic liquid carrying sulfuric acid moiety as a solvent, catalytic acid-free green polymerization of phenol with paraformaldehyde was accomplished. The ionic liquid was efficiently recovered and reused in new polymerization process of phenol.

引用

页码：8533 / 8536

页数：4

共 33 条

[11] Ionic liquids in heterocyclic synthesis [J].

Martins, Marcos A. P. ;

Frizzo, Clarissa P. ;

Moreira, Dayse N. ;

Zanatta, Nilo ;

Bonacorso, Helio G. .

CHEMICAL REVIEWS, 2008, 108 (06) :2015-2050

[12] Solvatochromic studies of ionic liquid/organic mixtures [J].

Mellein, Berlyn R. ;

Aki, Sudhir N. V. K. ;

Ladewski, Rebecca L. ;

Brennecke, Joan F. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2007, 111 (01) :131-138

[13] New aspects on polarity of 1-alkyl-3-methylimidazolium salts as measured by solvatochromic probes [J].

Oehlke, A ;

Hofmann, K ;

Spange, S .

NEW JOURNAL OF CHEMISTRY, 2006, 30 (04) :533-536

[14] Separated organized polymerization of an amphiphilic monomer and acrylamide in one-pot reaction [J].

Ozawa, Jun ;

Matsuo, Goh ;

Kamo, Naoki ;

Tsujii, Kaoru .

MACROMOLECULES, 2006, 39 (23) :7998-8002

[15] Catalysis in ionic liquids [J].

Parvulescu, Vasile I. ;

Hardacre, Christopher .

CHEMICAL REVIEWS, 2007, 107 (06) :2615-2665

[16] Ultrafast synthesis of ultrahigh molar mass polymers by metal-catalyzed living radical polymerization of acrylates, methacrylates, and vinyl chloride mediated by SET at 25 °C [J].

Percec, Virgil ;

Guliashvili, Tamaz ;

Ladislaw, Janine S. ;

Wistrand, Anna ;

Stjerndahl, Anna ;

Sienkowska, Monika J. ;

Monteiro, Michael J. ;

Sahoo, Sangrama .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) :14156-14165

[17]

SANCHEZ CG, 2006, CHEM COMMUN, P3797

[18] Amino-acid-functionalized solvatochromic probes [J].

Schreiter, Katja ;

Spange, Stefan .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2008, 21 (03) :242-250

[19] An in-depth look at the effect of Lewis acid catalysts on Diels-Alder cycloadditions in ionic liquids [J].

Silvero, G ;

Arévalo, MJ ;

Bravo, JL ;

Avalos, M ;

Jiménez, JL ;

López, I .

TETRAHEDRON, 2005, 61 (30) :7105-7111

[20] Free radical polymerization of n-butyl methacrylate in ionic liquids [J].

Strehmel, V ;

Laschewsky, A ;

Wetzel, H ;

Görnitz, E .

MACROMOLECULES, 2006, 39 (03) :923-930

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