Synthesis of noble molybdenum and tungsten complexes for hydrocracking catalyst of heavy oil

Sunyoung Shin; Ji Hun Lee; Yun Kyong Jo; Manh Tung Nguyen; Bo Keun Park; Sunyoung Park; Chul Wee Lee; Chang Gyoun Kim; Taek-Mo Chung

Journal of Industrial and Engineering Chemistry, Vol.72, 408-413, April, 2019

DOI10.1016/j.jiec.2018.12.043 Export Citation

Synthesis of noble molybdenum and tungsten complexes for hydrocracking catalyst of heavy oil

Sunyoung Shin¹, Ji Hun Lee¹, Yun Kyong Jo¹, Manh Tung Nguyen^{2, 3}, Bo Keun Park^{1, 2}, Sunyoung Park³, Chul Wee Lee^{2, 3}, Chang Gyoun Kim^{1, 2}, and Taek-Mo Chung^{1, 2, †}

¹Thin Film Materials Research Center, Korea Research Institute of Chemical Technology, Daejeon 34114, Republic of Korea
²Department of Chemical Convergence Materials, University of Science and Technology, Daejeon, 34113, Republic of Korea
³Research Center for Convergent Chemical Process, Korea Research Institute of Chemical Technology, Daejeon, 34114, Republic of Korea

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This paper reports the synthesis of six potential catalyst precursors for hydrocracking reactions for vacuum residue refinement. New group 6 transition metal complexes, (LM(CO)3) (M = Mo or W, L1 = 3- phenyl-1-propyne, L2 = 4-phenyl-1-butyne, and L3 = 5-phenyl-1-pentyne) were prepared by simply stirring M(CO)3(RCN)3 in THF solution. New compounds were applied as a catalyst precursor for hydrocracking of vacuum residue and the catalytic activity was compared to the commercially available material, Mo-octoate. LMo(CO)3 showed similar activities to Mo-octoate. Among all, L3Mo(CO)3 which had the longest alkyl chain showed a comparable result of low yield for coke and gas products.

Keywords:Hydrocracking reaction;Molybdenum compound;Oil refinement;Phenyl alkyne compounds;Tungsten compound

[References]

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Chang J, Tsubaki N, Fujimoto K, Fuel, 80, 1639 (2001)
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Yoshida R, Yoshida T, Narita H, Maekawa Y, Fuel, 65, 425 (1986)
Groenzin H, Mullins OC, Energy Fuels, 14(3), 677 (2000)
Zhao ZG, Zhang JW, Zhao FX, Zeng X, Liu XX, Xu GW, Fuel, 133, 45 (2014)
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Song CS, Catal. Today, 86(1-4), 211 (2003)
Sahu R, Song BJ, Im JS, Jeon YP, Lee CW, J. Ind. Eng. Chem., 27, 12 (2015)
Lei Z, Wu L, Gao L, Liu M, Shui H, Wang Z, Ren S, J. Ind. Eng. Chem., 19(5), 1421 (2013)
Rana MS, Samano V, Ancheyta J, Diaz JAI, Fuel, 86(9), 1216 (2007)
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Lee J, Hwang S, Seo JG, Hong UG, Jung JC, Song IK, J. Ind. Eng. Chem., 17(2), 310 (2011)
Rad MR, Rashidi A, Vafajoo L, Rashtchi M, J. Ind. Eng. Chem., 20(6), 4298 (2014)
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Ghosh U, Kulkarni K, Kulkarni AD, Chaudhari PL, Chem. Process Eng. Res., 34, 51 (2015)
Lee DW, Yoo BR, J. Ind. Eng. Chem., 20(6), 3947 (2014)
Kouzu M, Kuriki Y, Uchida K, Energy Fuels, 19, 25 (2005)
Terai S, Fukuyama H, Uehara K, Fujimoto K, J. Jpn. Pet. Inst., 43, 17 (2000)
Miyatani Y, Yasuda S, Su Y, Kaneda K, Murata S, Nomura M, J. Jpn. Pet. Inst., 42, 246 (1999)
Lee DK, Park SK, Yoon WL, Lee IC, Woo SI, Energy Fuels, 9(1), 2 (1995)
Montanari R, Marchionna M, Rosi S, Panariti M, Delbianco A, U. S. 7691256 2010.
Lopez J, Mckinney JD, Pasek EA, U. S. 4557821 1985.
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Trasatti S, J. Electroanal. Chem., 39, 163 (1972)
Cooke WS, Schmidt E, Song CS, Schobert HH, Energy Fuels, 10(3), 591 (1996)
Serrano DP, Aguado J, Escola JM, Rodriguez JM, Peral A, Chem. Mater., 18, 2462 (2006)
Hinnemann B, Moses PG, Bonde J, Jorgensen KP, Nielsen JH, Horch S, Chorkendorff L, Norskov JK, J. Am. Chem. Soc., 127(15), 5308 (2005)
Zhang SF, Herod AA, Kandiyoti R, Fuel, 76, 39 (1997)
Nguyen TM, Jung J, Lee CW, Cho J, Fuel, 214, 174 (2018)
Sahu R, Song BJ, Jeon YP, Lee CW, J. Ind. Eng. Chem., 35, 115 (2016)
Calemma V, Peratello S, Perego C, Appl. Catal. A: Gen., 190(1-2), 207 (2000)
Guo X, Zheng Y, Zhang B, J. Chen. Biomass Bioenergy, 33, 1469 (2009)
Panariti N, Del Bianco A, Del Piero G, Marchionna M, Appl. Catal. A: Gen., 204(2), 203 (2000)
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Go KS, Lim SH, Kim YK, Kwon EH, Nho NS, Catal. Today 305, 92 (2018): author>Kim YK, Kwon EH, Nho NS, Catal. Today, 305, 92 (2018).

[Referenced By]

[1] Thompson KFM, Geochim. Cosmochim. Acta, 47, 303 (1983)

[2] Newman PWG, Kenworthy JR, J. Am. Plan. Assoc., 55, 24 (1989)

[3] Chang J, Tsubaki N, Fujimoto K, Fuel, 80, 1639 (2001)

[4] Yoshida R, Miyazawa M, Ishiguro H, Itoh S, Haraguchi K, Nagaishi H, Narita H, Yoshida T, Maekawa Y, Mitarai Y, Fuel Process. Technol., 51(3), 195 (1997)

[5] Yoshida R, Miyazawa M, Yoshida T, Narita H, Maekawa Y, Fuel, 75, 99 (1996)

[6] Yoshida R, Yoshida T, Narita H, Maekawa Y, Fuel, 65, 425 (1986)

[7] Groenzin H, Mullins OC, Energy Fuels, 14(3), 677 (2000)

[8] Zhao ZG, Zhang JW, Zhao FX, Zeng X, Liu XX, Xu GW, Fuel, 133, 45 (2014)

[9] Ali MF, Abbas S, Fuel Process. Technol., 87(7), 573 (2006)

[10] Song CS, Catal. Today, 86(1-4), 211 (2003)

[11] Sahu R, Song BJ, Im JS, Jeon YP, Lee CW, J. Ind. Eng. Chem., 27, 12 (2015)

[12] Lei Z, Wu L, Gao L, Liu M, Shui H, Wang Z, Ren S, J. Ind. Eng. Chem., 19(5), 1421 (2013)

[13] Rana MS, Samano V, Ancheyta J, Diaz JAI, Fuel, 86(9), 1216 (2007)

[14] Olah GA, Molnar A, Hydrocarbon Chemistry, John Wiley & Sons, Inc., New York, 1995.

[15] Lee J, Hwang S, Seo JG, Hong UG, Jung JC, Song IK, J. Ind. Eng. Chem., 17(2), 310 (2011)

[16] Rad MR, Rashidi A, Vafajoo L, Rashtchi M, J. Ind. Eng. Chem., 20(6), 4298 (2014)

[17] Zhang S, Liu D, Deng W, Que G, Energy Fuels, 21(6), 3057 (2007)

[18] Ghosh U, Kulkarni K, Kulkarni AD, Chaudhari PL, Chem. Process Eng. Res., 34, 51 (2015)

[19] Lee DW, Yoo BR, J. Ind. Eng. Chem., 20(6), 3947 (2014)

[20] Kouzu M, Kuriki Y, Uchida K, Energy Fuels, 19, 25 (2005)

[21] Terai S, Fukuyama H, Uehara K, Fujimoto K, J. Jpn. Pet. Inst., 43, 17 (2000)

[22] Miyatani Y, Yasuda S, Su Y, Kaneda K, Murata S, Nomura M, J. Jpn. Pet. Inst., 42, 246 (1999)

[23] Lee DK, Park SK, Yoon WL, Lee IC, Woo SI, Energy Fuels, 9(1), 2 (1995)

[24] Montanari R, Marchionna M, Rosi S, Panariti M, Delbianco A, U. S. 7691256 2010.

[25] Lopez J, Mckinney JD, Pasek EA, U. S. 4557821 1985.

[26] Lopez J, Pasek EA, U.S. 4824821 1989.

[27] Trasatti S, J. Electroanal. Chem., 39, 163 (1972)

[28] Cooke WS, Schmidt E, Song CS, Schobert HH, Energy Fuels, 10(3), 591 (1996)

[29] Serrano DP, Aguado J, Escola JM, Rodriguez JM, Peral A, Chem. Mater., 18, 2462 (2006)

[30] Hinnemann B, Moses PG, Bonde J, Jorgensen KP, Nielsen JH, Horch S, Chorkendorff L, Norskov JK, J. Am. Chem. Soc., 127(15), 5308 (2005)

[31] Zhang SF, Herod AA, Kandiyoti R, Fuel, 76, 39 (1997)

[32] Nguyen TM, Jung J, Lee CW, Cho J, Fuel, 214, 174 (2018)

[33] Sahu R, Song BJ, Jeon YP, Lee CW, J. Ind. Eng. Chem., 35, 115 (2016)

[34] Calemma V, Peratello S, Perego C, Appl. Catal. A: Gen., 190(1-2), 207 (2000)

[35] Guo X, Zheng Y, Zhang B, J. Chen. Biomass Bioenergy, 33, 1469 (2009)

[36] Panariti N, Del Bianco A, Del Piero G, Marchionna M, Appl. Catal. A: Gen., 204(2), 203 (2000)

[37] Kim SH, Kim KD, Lee YK, J. Catal., 347, 127 (2017)

[38] Go KS, Lim SH, Kim YK, Kwon EH, Nho NS, Catal. Today 305, 92 (2018): author>Kim YK, Kwon EH, Nho NS, Catal. Today, 305, 92 (2018).