A novel and efficient procedure for the preparation of 4,40-bis(chloromethyl)biphenyl by chloromethylation of biphenyl catalyzed by PEG1000-DAIL under homogeneous catalysis in aqueous media

Yu Lin Hu; Ming Lu; Qiang Ge; Peng Cheng Wang; Ting Ting Lu

Journal of Industrial and Engineering Chemistry, Vol.16, No.4, 615-619, July, 2010

DOI10.1016/j.jiec.2010.03.005 Export Citation

A novel and efficient procedure for the preparation of 4,40-bis(chloromethyl)biphenyl by chloromethylation of biphenyl catalyzed by PEG1000-DAIL under homogeneous catalysis in aqueous media

Yu Lin Hu, Ming Lu^†, Qiang Ge, Peng Cheng Wang, and Ting Ting Lu

Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, PR China

E-mail:

As described in this article, 4,4'-bis(chloromethyl)biphenyl was obtained in 85% excellent yield by chloromethylation of biphenyl catalyzed by the recyclable temperature-dependant phase-separation system that comprised the dicationic acidic ionic liquid PEG1000-DAIL and methylcyclohexane under homogeneous catalysis in aqueous media. Compared to other synthetic methods, the novel method not only enhanced the yield, but also made the operating units easy workup. The mechanism of chloromethylation reaction and the process of catalysis in the thermoregulated ionic liquid bi-phase system were proposed.

Keywords:4,40-bis(Chloromethyl)biphenyl;Chloromethylation;PEG1000-DAIL;Thermoregulated ionic liquid biphasic;system

[References]

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Ohno K, Morita H, Moteki S, Akatsuka Y, US 5780571 (1998)
Randell DR, Hyde TG, GB 1551966 (1979)
Xia XW, Lu JM, Zhai JX, J. Chem. Eng. Chin. Univ., 19, 660 (2005)
Shen YJ, Fluorescent Whitening Agent, Chemical Industry Press, Beijing (1996)
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Dougherty EM, Guthrie K, Shapiro M, Biol. Control., 5, 383 (1995)
De Pierri WGJ, Eahart HW, US 2964573 (1960)
Kanakalashmi B, Mathai KP, Sethna S, J. Indian Chem. Soc., 43, 469 (1966)
Wakae M, Konishi K, Yuki Gosei Kagaku Kyoukaishi, 14, 615 (1956)
Vansheidt AA, Melnikova EP, Yu AT, Zh. Prikl. Khim., 34, 705 (1961)
Suyama S, Ishigaki H, JP 53009724 (1978)
Snow JE, US 2859253 (1958)
John TM, Theodore HF, US 3007975 (1961)
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Kuroda N, Nakamura T, JP 11130706 (1999)
Min BS, Park YC, J. Ind. Eng. Chem., 15(4), 595 (2009)
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Xi Z, Zhou N, Sun Y, Li K, Science., 292, 1139 (2001)
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[Referenced By]

[1] Fang Q, Zhu CY, Ren XL, Xue Z, Xia JZ, Shen YJ, Fine Specialty Chem., 13, 25 (2005)

[2] Ohno K, Morita H, Moteki S, Akatsuka Y, US 5780571 (1998)

[3] Randell DR, Hyde TG, GB 1551966 (1979)

[4] Xia XW, Lu JM, Zhai JX, J. Chem. Eng. Chin. Univ., 19, 660 (2005)

[5] Shen YJ, Fluorescent Whitening Agent, Chemical Industry Press, Beijing (1996)

[6] Johnen BG, Soil Biol. Biochem., 10, 495 (1978)

[7] John RA, Janet MS, Soil Biol. Biochem., 7, 205 (1975)

[8] Dougherty EM, Guthrie K, Shapiro M, Biol. Control., 5, 383 (1995)

[9] De Pierri WGJ, Eahart HW, US 2964573 (1960)

[10] Kanakalashmi B, Mathai KP, Sethna S, J. Indian Chem. Soc., 43, 469 (1966)

[11] Wakae M, Konishi K, Yuki Gosei Kagaku Kyoukaishi, 14, 615 (1956)

[12] Vansheidt AA, Melnikova EP, Yu AT, Zh. Prikl. Khim., 34, 705 (1961)

[13] Suyama S, Ishigaki H, JP 53009724 (1978)

[14] Snow JE, US 2859253 (1958)

[15] John TM, Theodore HF, US 3007975 (1961)

[16] Kuroda N, Nakamura T, JP 11080047 (1999)

[17] Kuroda N, Nakamura T, JP 11130706 (1999)

[18] Min BS, Park YC, J. Ind. Eng. Chem., 15(4), 595 (2009)

[19] Kuroda N, Nakamura T, JP 10139699 (1998)

[20] Sakata C, Akamatsu T, JP 3188029 (1991)

[21] Taniguchi H, Nomura E, Uchida M, Nasaka N, Doi A, Kawashima S, JP 9208506 (1997)

[22] Taniguchi H, Nomura E, Uchida M, Nasaka N, Doi A, Kawashima S, JP 10077238 (1998)

[23] Motoyama R, Fujimoto T, Kakehi T, JP 38002863 (1963)

[24] Anastas PT, Williamson TCE, Green Chemistry: Frontiers in Benign Chemical Synthesis and Processes, Oxford University Press, Oxford (1998)

[25] Soeda M, Shin K, WO 9811039 (1998)

[26] Taniguchi H, Nomura E, Uchida M, Nasaka N, Doi A, Kawashima S, JP 9208510 (1997)

[27] Soeda M, Mizuuchi K, Shin K, JP 9087214 (1997)

[28] Ogwa T, Kubo M, Yoshimitsu M, JP 2240036 (1990)

[29] Kishida T, Yamauchi T, Kubota Y, Green Chem., 6, 57 (2004)

[30] Yamauchi K, Kishida T, Sugi Y, Kubota Y, JP 2004002333 (2004)

[31] Kishida T, Yamauchi T, Komura K, Kubota Y, Sugi Y, J. Mol. Catal. A: Chem., 46, 268 (2006)

[32] Shirokura H, Hirokura H, Tomiyoshi T, JP 2001348357 (2001)

[33] Wasserschein P, Welton T, Ionic Liquids in Syntheses, Wiley-VCH, Weinhein (2003)

[34] Rantwijk F, Lau RM, Sheldon RA, Trends Biotechnol., 21, 131 (2003)

[35] Reichardt C, Org. Process Res. Dev., 11, 105 (2007)

[36] Albrecht T, Moth-Poulsen K, Christensen JB, Hjelm J, Bjornholm T, Ulstrup J, J. Am. Chem. Soc., 128(20), 6574 (2006)

[37] Wang Y, Shang ZC, Wu TX, Synth. Commun., 36, 3053 (2006)

[38] Fang YX, Deng YQ, Ren QG, Huang JP, Zhang SD, Huang BH, Zhang K, Chin. J. Chem. Eng., 16(3), 357 (2008)

[39] Xi Z, Zhou N, Sun Y, Li K, Science., 292, 1139 (2001)

[40] Ooi T, Maruoka K, Angew. Chem. Int. Ed., 46, 4222 (2007)

[41] Gladysz JA, Chem. Rev., 102(10), 3215 (2002)

[42] Sunitha S, Kanjilal S, Reddy PS, Rachapudi BN, Tetrahedron Lett., 48, 6962 (2007)

[43] Leng Y, Wang J, Zhu DR, Ren XQ, Ge HQ, Shen L, Angew. Chem. Int. Ed., 48, 168 (2009)

[44] Tan B, Jiang JY, Wang YH, Wei L, Chen DJ, Jin ZL, Appl. Organomet. Chem., 22, 620 (2008)

[45] Zhi HZ, Luo J, Ma W, Lu CX, Chem. J. Chin. Univ., 29, 2007 (2008)

[46] Zhi HZ, Lu CX, Zhang Q, Luo J, Chem. Commun., 2878 (2009)

[47] Patel R, Im SJ, Ko YT, Kim JH, Min BR, J. Ind. Eng. Chem., 15(3), 299 (2009)