Evaluation of Organic Sulfonic Acids as Catalyst during Cellulose Liquefaction Using Ethylene Carbonate

Sung Phil Mun; El-Barbary M. Hassa; Tae ho Yoon

Journal of Industrial and Engineering Chemistry, Vol.7, No.6, 430-434, November, 2001

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Evaluation of Organic Sulfonic Acids as Catalyst during Cellulose Liquefaction Using Ethylene Carbonate

Sung Phil Mun^†, El-Barbary M. Hassa¹, and Tae ho Yoon²

Institute of Agricultural Science & Technology (Division of Forest Science, College of Agriculture), Chonbuk National University, Chonju 561-756, Korea
¹Cellulose & Paper Department, National Research Center, Tahrir Street-Dokki 12311-Cairo, Egypt
²Department of Material Science and Engineering, Kwangju Institute of Science and Technology, 1 Oryong-dong, Kwangju 500-712, Korea

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Cellulose liquefaction was successfully conducted using ethylene carbonate (EC) as a liquefying agent and organic sulfonic acids, such as methanesulfonic acid (MSA) or p-toluenesulfonic acid (PTSA), as a catalyst. Due to the higher crystallinity of cellulose, organic sulfonic acids were more effective at higher temperatures (170 ~ 180 ℃). Consequently, at 180 ℃ with 3.58 mmol of organic sulfonic acid catalysts, liquefaction yield was about 99% compared to 80% at 150 ℃ and with 8.95 mmol. In addition, at 180 ℃, the rate of reaction using MSA was approximately 5 times faster than at 150 ℃. Sulfuric acid (SA) was more effective than the organic sulfonic acids at lower acid concentrations and temperatures. FTIR spectroscopy of the residue revealed a strong carbonyl band when SA was used as the catalyst, indicating more decomposition of the cellulose. An X-ray analysis showed similar crystallinity results for the cellulose and the residue that remained after liquefaction, indicating that most of the residue was derived from the crystalline area of cellulose.

Keywords:cellulose;ethylene carbonate;methanesulfonic acid;p-toluenesulfonic acid;crystallinity

[References]

Yamada T, Ono H, Bioresour. Technol., 70(1), 61 (1999)
Ono H, Sudo K, Japan Patent Appl., 217070 (1989)
Ono H, Yamada T, Hatano Y, Motohashi K, J. Adhes., 59, 135 (1996)
Shiraishi N, Shirakawa K, Kurimoto Y, Japan Patent Appl., 106128 (1992)
Alma MH, Yoshioka M, Yao Y, Shiraishi N, Wood Sci. Technol., 32, 297 (1998)
Yao Y, Yoshioka M, Shiraishi N, Mokuzai Gakkaishi, 41, 659 (1995)
Yamada T, Ono H, 2nd Annual Partnership for Environmental Improvement and Economic-Development Conference, Syracuse, New York, U.S.A. (2000)
Pu S, Shiraishi N, Mokuzai Gakkaishi, 39, 453 (1993)
Alma MH, Yoshioka M, Yao Y, Shiraishi N, Wood Sci. Technol., 30, 39 (1995)
Lin LZ, Yoshioka M, Yao YG, Shiraishi N, J. Appl. Polym. Sci., 52(11), 1629 (1994)
Maldas D, Shiraishi N, Biomass Bioenerg., 12(4), 273 (1997)
Mun SP, Lu JL, Rhee JM, Proc. Korea TAPPI, p. 164 (1999)
Mun SP, Lu JL, Rhee JM, Proc. Korea TAPPI, p. 169 (1999)
Yao Y, Yoshioka M, Shiraishi N, Mokuzai Gakkaishi, 39, 930 (1993)
Shiraishi N, Wood and Cellulosic Chemistry, David N.-S. Hon and N. Shiraishi Eds., p. 863, New York, Marcel Dekker Inc. (1991)
Pouchert CJ, Aldrich Library of FT-IR Spectra, Ed. 1, Vol. 3, p. 188, p. 635 (1989)
Jaing ZH, Ph.D. Thesis, Kangwon National University, Republic of Korea. (2000)
Segal L, Creely JJAE, Conrad MCM, Text. Res. J., 29, 786 (1959)

[Referenced By]

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[1] Yamada T, Ono H, Bioresour. Technol., 70(1), 61 (1999)

[2] Ono H, Sudo K, Japan Patent Appl., 217070 (1989)

[3] Ono H, Yamada T, Hatano Y, Motohashi K, J. Adhes., 59, 135 (1996)

[4] Shiraishi N, Shirakawa K, Kurimoto Y, Japan Patent Appl., 106128 (1992)

[5] Alma MH, Yoshioka M, Yao Y, Shiraishi N, Wood Sci. Technol., 32, 297 (1998)

[6] Yao Y, Yoshioka M, Shiraishi N, Mokuzai Gakkaishi, 41, 659 (1995)

[7] Yamada T, Ono H, 2nd Annual Partnership for Environmental Improvement and Economic-Development Conference, Syracuse, New York, U.S.A. (2000)

[8] Pu S, Shiraishi N, Mokuzai Gakkaishi, 39, 453 (1993)

[9] Alma MH, Yoshioka M, Yao Y, Shiraishi N, Wood Sci. Technol., 30, 39 (1995)

[10] Lin LZ, Yoshioka M, Yao YG, Shiraishi N, J. Appl. Polym. Sci., 52(11), 1629 (1994)

[11] Maldas D, Shiraishi N, Biomass Bioenerg., 12(4), 273 (1997)

[12] Mun SP, Lu JL, Rhee JM, Proc. Korea TAPPI, p. 164 (1999)

[13] Mun SP, Lu JL, Rhee JM, Proc. Korea TAPPI, p. 169 (1999)

[14] Yao Y, Yoshioka M, Shiraishi N, Mokuzai Gakkaishi, 39, 930 (1993)

[15] Shiraishi N, Wood and Cellulosic Chemistry, David N.-S. Hon and N. Shiraishi Eds., p. 863, New York, Marcel Dekker Inc. (1991)

[16] Pouchert CJ, Aldrich Library of FT-IR Spectra, Ed. 1, Vol. 3, p. 188, p. 635 (1989)

[17] Jaing ZH, Ph.D. Thesis, Kangwon National University, Republic of Korea. (2000)

[18] Segal L, Creely JJAE, Conrad MCM, Text. Res. J., 29, 786 (1959)