REVIEWS

Recent Advances on Carbonylation of 1,3-Dienes

  • Peng Wang ,
  • Da Yang ,
  • Huan Liu
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  • a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    b Department of Chemistry, College of Science, China University of Petroleum (East China), Qingdao, Shandong 266580
* Corresponding author. E-mail:

Received date: 2021-05-21

  Revised date: 2021-06-09

  Online published: 2021-06-22

Supported by

National Natural Science Foundation of China: Youth Project(21901250); General Programs of China Postdoctoral Science Foundation(2019M651625)

Abstract

1,3-Butadiene is the main component of C4 fraction in naphtha cracking process. The products of 1,3-butadiene carbonylation (hexanedial, adipic acid and dimethyl adipate) can be used in the production of nylon, plasticizer and pharmaceutical intermediates. How to efficiently and high chemo-/regio-selectivity synthesize these high value-added products has always been a difficult problem in organic chemistry research and industrial production. In this paper, the research progress of carbonylation (hydroformylation, hydroesterification, hydrocarboxylation) of 1,3-dienes (especially 1,3-butadiene) to construct high value-added chemicals in recent years is reviewed, then the difficulties and future development of this method are prospected.

Cite this article

Peng Wang , Da Yang , Huan Liu . Recent Advances on Carbonylation of 1,3-Dienes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3379 -3389 . DOI: 10.6023/cjoc202105036

References

[1]
Nienburg, H. J.; Kummer, R.DE 2317625, 1974.
[2]
Mirbach, M. Transition Met. Chem. 1984, 9, 465.
[3]
Herrmann, N.; Vogelsang, D.; Behr, A.; Seidensticker, T. ChemCatChem 2018, 10, 5342.
[4]
Börner, A.; Franke, R. Hydroformylation: Fundamentals, Processes, and Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2016.
[5]
Klosin, J.; Landin, C. R. Acc. Chem. Res. 2007, 40, 1251.
[6]
Fell, B.; Hermanns, P.US 5434312, 1995.
[7]
Briggs, J.; Packett, D.; Bryant, D.; Phillips, A.; Schreck, D.; Olson, K.; Tjaden, E.; Guram, A.; Eisenschmid, T.; Bragham, E.WO 9740001, 1997.
[8]
Packett, D. L. (to Union Carbide Coatings Service Technology Corp.) US 5312996, 1994.
[9]
Fell, B.; Rupilius, W. Tetrahedron Lett. 1969, 10, 2721.
[10]
van Leeuwen, P.; Roobeek, C. F. J. Mol. Catal. 1985, 31, 345.
[11]
Fell, B.; Hermanns, P.; Bahrmann, H. J. Prakt. Chem. 1998, 340, 459.
[12]
Packett, D. L.; Briggs, J. R.; Bryant, D. R.; Phillips, A. G. WO 1997040003, 1997.
[13]
Fell, B.; Bahrmann, H. J. Mol. Catal. 1980, 8, 329.
[14]
Fell, B.; Rupilius, W. Tetrahedron Lett. 1969, 32, 2721.
[15]
van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Mol. Catal. 1985, 31, 345.
[16]
Fyhr, C.; Garland, M. Organometallics 1993, 12, 1753.
[17]
Liu, G.; Garland, M. J. Organomet. Chem. 2000, 608, 76.
[18]
Kummer, R.; Schneider, W.; Weiss, F. J. (to BASF AG).DE 2741511, 1979.
[19]
Kummer, R.(to BASF AG) DE 2414253, 1976.
[20]
Roobeek, C. F. (to Shell Internationale Research Maatschappij B. V.) EP 0033554, 1981.
[21]
van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Mol. Catal. 1985, 31, 345.
[22]
Packett, D. L. (to Union Carbide Coatings Service Technology Corp. ) EP 577042, 1993.
[23]
Kummer, R.; Weiss, F. J. Proc.-Symp. Rhodium Homogeneous Catal. 1978, 87.
[24]
Kummer, R.(to BASF AG) DE 2414253, 1975.
[25]
Packett, D. L. (to Union Carbide Chemicals & Plastics)US 5312966, 1994.
[26]
Smits, H. A.; Spronken, J. M. H.; Wolters, H. F. W.; Boogers, J. A. F. (to DSMN. V.) EP 1223155, 2001.
[27]
Bertozzi, S.; Campigli, N.; Vitulli, G.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1995, 487, 41.
[28]
Ohgomori, Y.; Suzuki, N.; Sumitani, N. J. Mol. Catal. A: Chem. 1998, 133, 289.
[29]
Briggs, J. R.; Packett, D. L.; Bryant, D. R.; Phillips, A. G.; Schreck, D. J.; Guram, A. S.; Olson, K. D.; Eisenschmid, T. C.; Tjaden, E. B. (to Union Carbide Chemicals & Plastics Technology Corporation) US 6187970, 2001.
[30]
Huo, C. F.; Li, Y. W.; Beller, M.; Jiao, H. J. Organometallics 2005, 24, 3634.
[31]
Smith, S. E.; Rosendahl, T.; Hofmann, P. Organometallics 2011, 30, 3643.
[32]
Schmidt, S.; Barath, E.; Prommnitz, T.; Rosendahl, T.; Rominger, F.; Hofmann, P. Organometallics 2014, 33, 6018.
[33]
Schmidt, S.; Deglmann, P.; Hofmann, P. ACS Catal. 2014, 4, 3593.
[34]
Schmidt, S.; Barath, E.; Larcher, C.; Rosendahl, T.; Hofmann, P. Organometallics 2015, 34, 841.
[35]
Maji, T.; Mendis, C. H.; Thompson, W. H.; Tunge, J. A. J. Mol. Catal. A: Chem. 2016, 424, 145.
[36]
Mormul, J.; Breitenfeld, J.; Trapp, O.; Paciello, R.; Schaub, T.; Hofmann, P. ACS Catal. 2016, 6, 2802.
[37]
Yua, S. M.; Snavelya, W. K.; Chaudharia, R. V.; Subramaniam, B. Mol. Catal. 2020, 484, 110721.
[38]
Tenorio, M. J.; Chaudhari, R. V.; Subramaniam, B. Ind. Eng. Chem. Res. 2019, 58, 22526.
[39]
Musser, M. T. Ullmanns Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000.
[40]
Alini, S.;Babini P. Handbook of Advanced Methods and Processes in Oxidation Catalysis, Imperial College Press, London, 2014.
[41]
Zachry, J. B.; Aldridge, C. L. US 3161672, 1964.
[42]
Von, K. N. US 3876695, 1975.
[43]
Isogai, Y.; Hosokawa, M.; Ookawa, T.; Wakui, N.; Watanabe, T.JP 5788147, 1982.
[44]
Hsu, C. K.; Dobinson, F.US 4575562, 1986.
[45]
Maerkl, R.US 4777284, 1988.
[46]
Drent, E.; Van, G. J. US 4861912, 1989.
[47]
Omatsu, T.; Tokito, Y.JP 04208247, 1992.
[48]
Atadan, E. M.; Bruner, H. S. US 5292944, 1994.
[49]
Matsuda, A.; Fujii, T.JP 06192175, 1994.
[50]
Denis, P.; Patois, C.; Perron, R.EP 0648731, 1995.
[51]
Sielcken, O. E.; Hovenkamp, H.WO 9506027, 1995.
[52]
Poole, A. D.; Sunley, J. G. UK 2327420, 1999.
[53]
Drent, E.; Jager, W. W. WO 00056695, 2000.
[54]
Sielcken, O. E. WO 0121569, 2001.
[55]
Yang, J.; Liu, J. W.; Neumann, H.; Franke, R.; Jackstell, R.; Beller, M. Science 2019, 366, 1514.
[56]
Yang, J.; Liu, J. W.; Ge, Y.; Huang, W. H.; Ferretti, F.; Neumann, H.; Jiao, H. J.; Franke, R.; Jackstell, R.; Beller, M. Angew. Chem. Int. Ed. 2021, 60, 2.
[57]
Skoog, E.; Shin, J. H.; Saez-Jimenez, V.; Mapelli, V.; Olsson, L. Biotechnol. Adv. 2018, 36, 2248.
[58]
Gunukula, S.; Anex, R. P. Biofuels, Bioprod. Biorefin. 2017, 11, 897.
[59]
Bart, J. C. J.; Cavallaro, S. Ind. Eng. Chem. Res. 2015, 54, 1.
[60]
Eia, US.Annual Energy Outlook 2015: with Projections to 2040 2017.
[61]
Eggleston, S.; Buendia, L.; Miwa, K.; Ngara, T.; Tanabe, K. Institute for Global Environmental Strategies (Japó). 2006 IPCC Guidelines for National Greenhouse Gas Inventories, IGES, Japan, 2006.
[62]
Agency USEP Inventory of US Greenhouse Gas Emissions and Sinks: 1990-2015, US Environmental Protection Agency, Washington, DC, 2017.
[63]
Lewis, Sr. R. L. Carcinogenically Active Chemicals, Van Nostrand Reinhold Company, New York, 1990.
[64]
Smith, M. T.; Jones, R. M.; Smith, A. H. Cancer Epidemiol. Biomarkers Prev. 2007, 16. 385.
[65]
Rios, J.; Lebeau, J.; Yang, T.; Li, S.; Lynch, M. D. Green Chem. 2021, 23, 3172.
[66]
Tortajada, A.; Ninokata, R.; Martin, R. J. Am. Chem. Soc. 2018, 140, 2050.
[67]
Trzeciak, A. M.; Ziółkowski, J. J. J. Organomet. Chem. 1994, 479, 213.
[68]
Adkins, H.; Williams, J. L. R.; J. Org. Chem. 1952, 17, 980.
[69]
Barros, H. J. V.; Guimãraes, C. C.; dos Santos, E. N.; Gusevskaya, E. V. Catal. Commun. 2007, 8, 747.
[70]
Barros, H. J. V.; Guimãraes, C. C.; dos Santos, E. N.; Gusevskaya, E. V. Organometallics 2007, 26, 2211.
[71]
Behr, A.; Reyer, S.; Tenhumberg, N. Dalton Trans. 2011, 40, 11742.
[72]
Yu, S.; Chie, Y. M.; Zhang, X.; Dai, L.; Zhang, X. Tetrahedron Lett. 2009, 50, 5575.
[73]
Morikawa, M. Bull. Chem. Soc. Jpn. 1964, 37, 379.
[74]
Watkins, A. L.; Landis, C. R. Org. Lett. 2011, 13, 164.
[75]
Horiuchi, T.; Ohta, T.; Shirakawa, E.; Nozaki, K.; Takaya, H. Tetrahedron 1997, 53, 7795.
[76]
Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 2, 155.
[77]
Adint, T. T.; Wong, G. W.; Landis, C. R. J. Org. Chem. 2013, 78, 4231.
[78]
Adkins, H.; Williams, J. L. R. J. Org. Chem. 1952, 17, 980.
[79]
Meyer, W. Hydrocarbon Process., nt. Ed. 1976, 194, 235.
[80]
Morgan, M. Chem. Ind. (London) 1999, 645.
[81]
Cheung, T. T. P. Cyclopentadiene and Dicyclopentadiene, in Kirk-Othmer Encyclopedia of Chemical Technology, Wiley-VCH Verlag GmbH, Weinheim, 2004.
[82]
Hönicke, D.; Födisch, R.; Claus, P.; Olson, M. Ullmann's Encyclopedia of Industrial Chemistry, 7th ed., Wiley-VCH, Weinheim, 2005, p. 1-14.
[83]
Behr, A.; Levikov, D.; Vogelsang, D. J. Mol. Catal. A: Chem. 2015, 406, 114.
[84]
Neubert, P.; Fuchs, S.; Behr, A. Green Chem. 2015, 17, 4045.
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