1,3-二烯烃的羰基化反应研究进展

doi:10.6023/cjoc202105036

摘要/Abstract

1,3-丁二烯是石脑油裂解过程C₄馏分中最主要的组分, 通过羰基化反应合成的下游产品己二醛、己二酸、己二酸二甲酯在尼龙、增塑剂、医药中间体等的生产上有重要应用. 但是如何高效高化学/区域选择性合成这类高附加值产品一直是有机化学研究以及工业化生产的难题. 综述了近年来1,3-二烯类化合物(特别是1,3-丁二烯)发生羰基化反应(氢甲酰化反应、氢酯化反应、氢羧基化反应)构建高附加值化学品的研究进展, 并对该方法存在的难点以及未来发展方向进行了阐述和展望.

关键词: 1,3-丁二烯, 氢甲酰化反应, 氢酯化反应, 合成气, 均相催化

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.

Key words: 1,3-butadiene, hydroformylation, hydroesterification, syngas, homogeneous catalysis

引用此文

王鹏, 杨妲, 刘欢. 1,3-二烯烃的羰基化反应研究进展[J]. 有机化学, 2021, 41(9): 3379-3389.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 26

图1. 均相催化剂参与1,3-丁二烯的官能团化反应

Figure 1. Homogeneously catalyzed 1,3-diene functionalization

图式1. 1,3-丁二烯的氢甲酰化及其下游转化

Scheme 1. Hydroformylation of 1,3-butadiene and subsequent transformations

图式2. 缩醛保护的1,3-丁二烯的氢甲酰化反应

Scheme 2. Hydroformylation of 1,3-butadiene with transient protection of the first incorporated carbonyl group as acetal

图式3. 均三甲苯溶剂化铑原子促进直链的共轭二烯烃选择性氢甲酰化制备β,γ-不饱和单醛类化合物

Scheme 3. Selective hydroformylation of open-chain conjugated dienes promoted by mesitylene-solvated rhodium atoms to give β,γ-unsaturated monoaldehydes

图式4. 不同膦配体调控1,3-丁二烯作为原料制备乙二醛

Scheme 4. Formation of 1,6-hexanedial via hydroformylation of 1,3-butadiene by using different ligands

图式5. 铑催化1,3-丁二烯的“氢甲酰化-氢化”串联反应

Scheme 5. Rh-catalyzed reductive hydroformylation of 1,3- butadiene

图式6. 丁二烯氢甲酰化反应区域选择性的密度泛函数研究

Scheme 6. Regioselective hydroformylation of butadiene: density functional studies

图式7. 低压条件下的铑催化1,3-丁二烯双氢甲酰化反应

Scheme 7. Rhodium-catalyzed bis-hydroformylation of 1,3-butadiene to adipic aldehyde at low pressure

图式8. 铑催化1,3-丁二烯氢甲酰化反应中的巴豆基中间体

Scheme 8. Crotyl intermediates in Rh-catalyzed hydroformylation of 1,3-butadiene

图式9. 双膦配体调控铑催化1,3-丁二烯氢甲酰化反应的密度泛函研究

Scheme 9. Density functional investigations of the Rh-catalyzed hydroformylation of 1,3-butadiene with bisphosphite ligands

图式10. 铑催化 1,3-丁二烯氢甲酰化制备己二醛

Scheme 10. Rhodium-catalyzed hydroformylation of 1,3-buta- diene to adipic aldehyde

图式11. 1,3-丁二烯氢甲酰化过程中的异构化反应

Scheme 11. Isomerizing hydroformylation of pent-3-enal

图式12. 1,3-丁二烯选择性双氢甲酰化合成己二酸、1,6-己二醇以及1,6-己二胺

Scheme 12. Synthesis of adipic acid, 1,6-hexanediol and 1,6-hexanediamine via double?n?selective hydroformylation of 1,3-butadiene

图式13. 1,3-丁二烯氢甲酰化制备己二醛

Scheme 13. Hydroformylation of 1,3-diene

图式14. 二氧化碳膨胀介质中铑催化1,3-丁二烯和4-戊烯醛的氢甲酰化反应制备己二醛

Scheme 14. Rh-catalyzed hydroformylation of 1,3-butadiene and pent-4-enal to adipaldehyde in CO2?expanded media

图式15. 吡啶取代的双齿膦配体调控钯催化1,3-丁二烯的双氢酯化反应合成己二酸二酯类化合物

Scheme 15. Direct synthesis of adipic acid esters via palladium- catalyzed carbonylation of 1,3-dienes

图式16. 钯催化1,3-二烯烃的高效羰基化反应

Scheme 16. Efficient palladium-catalyzed carbonylation of 1,3- dienes

图式17. 镍催化1,3-二烯烃与CO2的区域选择性二羧基化反应

Scheme 17. Ni-catalyzed site-selective dicarboxylation of 1,3- dienes with CO2

图式18. 钴催化共轭二烯的氢甲酰化反应

Scheme 18. Hydroformylation of conjugated dienes catalyzed by cobalt

图式19. 异戊二烯的氢甲酰化反应

Scheme 19. Hydroformylation of isoprene

图式20. 1,5-己二烯氢甲酰化合成糠醛

Scheme 20. Hydroformylation of 1,5-hexadiene to pimelaldehyde

图式21. 铑催化1,3-二烯烃氢甲酰化制备高对映选择性β,γ-不饱和醛类化合物

Scheme 21. Regioselective rhodium-catalyzed hydroformylation of 1,3-dienes to highly enantioenriched β,γ-unsaturated aldehydes

图式22. 不同反应时间对1-苯基-1,3-丁二烯的不对称氢甲酰化反应的影响

Scheme 22. Influence of the reaction time on chemo- and enantioselectivity in the hydroformylation of 1-phenyl-1,3-butadiene

图式23. 1,3-戊二烯和1,3-丁二烯氢甲酰化反应的不同

Scheme 23. Differences in the hydroformylation of 1,3-butadiene and 1,3-pentadiene

图式24. 环戊二烯的氢甲酰化反应

Scheme 24. Hydroformylation of cyclopentadiene

图式25. 1,3-戊二烯的氢甲酰化反应

Scheme 25. Hydroformylation of piperylene

参考文献 84

[1]	Nienburg, H. J.; Kummer, R.DE 2317625, 1974.
[2]	Mirbach, M. Transition Met. Chem. 1984, 9, 465. doi: 10.1007/BF00620679
[3]	Herrmann, N.; Vogelsang, D.; Behr, A.; Seidensticker, T. ChemCatChem 2018, 10, 5342. doi: 10.1002/cctc.v10.23
[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. doi: 10.1021/ar7001039
[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. doi: 10.1016/S0040-4039(01)88252-6
[10]	van Leeuwen, P.; Roobeek, C. F. J. Mol. Catal. 1985, 31, 345. doi: 10.1016/0304-5102(85)85117-8
[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. doi: 10.1016/0304-5102(80)80074-5
[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. doi: 10.1016/0304-5102(85)85117-8
[16]	Fyhr, C.; Garland, M. Organometallics 1993, 12, 1753. doi: 10.1021/om00029a036
[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. doi: 10.1016/0304-5102(85)85117-8
[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. doi: 10.1016/S1381-1169(98)00129-0
[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. doi: 10.1021/om0500422
[31]	Smith, S. E.; Rosendahl, T.; Hofmann, P. Organometallics 2011, 30, 3643. doi: 10.1021/om200334g
[32]	Schmidt, S.; Barath, E.; Prommnitz, T.; Rosendahl, T.; Rominger, F.; Hofmann, P. Organometallics 2014, 33, 6018. doi: 10.1021/om500643t
[33]	Schmidt, S.; Deglmann, P.; Hofmann, P. ACS Catal. 2014, 4, 3593. doi: 10.1021/cs500718v
[34]	Schmidt, S.; Barath, E.; Larcher, C.; Rosendahl, T.; Hofmann, P. Organometallics 2015, 34, 841. doi: 10.1021/om501015z
[35]	Maji, T.; Mendis, C. H.; Thompson, W. H.; Tunge, J. A. J. Mol. Catal. A: Chem. 2016, 424, 145. doi: 10.1016/j.molcata.2016.08.021
[36]	Mormul, J.; Breitenfeld, J.; Trapp, O.; Paciello, R.; Schaub, T.; Hofmann, P. ACS Catal. 2016, 6, 2802. doi: 10.1021/acscatal.6b00189
[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. doi: 10.1021/acs.iecr.9b05184
[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. doi: 10.1126/science.aaz1293 pmid: 31857484
[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. doi: 10.1002/anie.v60.1
[57]	Skoog, E.; Shin, J. H.; Saez-Jimenez, V.; Mapelli, V.; Olsson, L. Biotechnol. Adv. 2018, 36, 2248. doi: S0734-9750(18)30175-7 pmid: 30389426
[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. doi: 10.1021/ie5020734
[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. doi: 10.1158/1055-9965.EPI-06-1057
[65]	Rios, J.; Lebeau, J.; Yang, T.; Li, S.; Lynch, M. D. Green Chem. 2021, 23, 3172. doi: 10.1039/D1GC00638J
[66]	Tortajada, A.; Ninokata, R.; Martin, R. J. Am. Chem. Soc. 2018, 140, 2050. doi: 10.1021/jacs.7b13220 pmid: 29376353
[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. doi: 10.1021/jo50007a012
[69]	Barros, H. J. V.; Guimãraes, C. C.; dos Santos, E. N.; Gusevskaya, E. V. Catal. Commun. 2007, 8, 747. doi: 10.1016/j.catcom.2006.09.015
[70]	Barros, H. J. V.; Guimãraes, C. C.; dos Santos, E. N.; Gusevskaya, E. V. Organometallics 2007, 26, 2211. doi: 10.1021/om060994n
[71]	Behr, A.; Reyer, S.; Tenhumberg, N. Dalton Trans. 2011, 40, 11742. doi: 10.1039/c1dt11292a
[72]	Yu, S.; Chie, Y. M.; Zhang, X.; Dai, L.; Zhang, X. Tetrahedron Lett. 2009, 50, 5575. doi: 10.1016/j.tetlet.2009.07.066
[73]	Morikawa, M. Bull. Chem. Soc. Jpn. 1964, 37, 379. doi: 10.1246/bcsj.37.379
[74]	Watkins, A. L.; Landis, C. R. Org. Lett. 2011, 13, 164. doi: 10.1021/ol102797t pmid: 21133397
[75]	Horiuchi, T.; Ohta, T.; Shirakawa, E.; Nozaki, K.; Takaya, H. Tetrahedron 1997, 53, 7795. doi: 10.1016/S0040-4020(97)00471-7
[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. doi: 10.1021/jo400525w
[78]	Adkins, H.; Williams, J. L. R. J. Org. Chem. 1952, 17, 980. doi: 10.1021/jo50007a012
[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. doi: 10.1016/j.molcata.2015.06.003
[84]	Neubert, P.; Fuchs, S.; Behr, A. Green Chem. 2015, 17, 4045. doi: 10.1039/C5GC00020C