Advances in the Production of Acrylic Acid and Its Derivatives by CO2/C2H4 Coupling

doi:10.6023/cjoc202110040

Abstract

Carbon dioxide (CO₂) is not just a greenhouse gas, but also an important and effective one-carbon resource, which is abundant in nature and can be used to produce organic chemicals, materials, and sugars etc. CO₂ is thermodynamically and kinetically inert because the carbon atom in CO₂ molecule is in its highest oxidation state. In the past decades, several catalytic systems have been developed for the utilization of CO₂. The catalytic conversion of CO₂ to unsaturated carboxylic acids and their derivatives has attracted great attention. Among them, the so-called “dream reaction” of coupling CO₂/C₂H₄ is 100% atom efficient. Transition metal-based catalysts are developed for catalytic transformation of CO₂/C₂H₄ into acrylic acid and its derivatives, including Ni, Pd, Fe, and Ru etc. In addition, the additives play an important role in improving the catalyst performance. In this review, the recent advances on transition metal complex catalyzed CO₂/C₂H₄ coupling reaction are summarized on the basis of catalyst activity and reaction mechanisms, including both the experiment and theoretical calculation. Furthermore, the challenges and perspectives in the catalytic transformation of CO₂/C₂H₄ are also discussed.

Key words: carbon dioxide, acrylic acid, coupling reaction, reaction mechanism

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Youcai Zhu, Xinxin Ding, Li Sun, Zhen Liu. Advances in the Production of Acrylic Acid and Its Derivatives by CO₂/C₂H₄ Coupling[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 965-977.

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Fig. & Tab. 27

Scheme 1. Formation of five-membered nickelalactone ring via CO2/C2H4 coupling

Scheme 2. Formation mechanism of five-membered nickelalactone ring

Scheme 3. Reaction of five-membered nickelalactone ring with N- or P-containing ligands

Scheme 4. Mechanism of acrylic acid production by coupling CO2/C2H4

Scheme 5. Possible pathways for reductive elimination of acrylic acid

Scheme 6. C—C coupling barriers (kJ/mol) in the Ni-catalyzed reaction

Figure 1. Steric maps of the Ni(L)(ethylene) complex (L=dmpe, dcpe, dtbpe)

Scheme 7. Mechanism of methyl acrylate production by coupling CO2/C2H4 in the presence of methyl iodide

Figure 2. Gibbs free energy (solid line) and enthalpy (dashed line) for the preparation of methyl acrylate by coupling CO2/C2H4 in the presence of MeI (kJ/mol)

Figure 3. Application of methylation reagents for Ni—O bond cleavage and release of methyl acrylate

Figure 4. Effect of solvents on methyl acrylate formation

Scheme 8. Possible pathways for Ni—O bond cleavage (kJ/mol)

Scheme 9. Proposed mechanism of CF3I-induced ring opening of nickelalactones

Scheme 10. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of alkyl iodides

Entry	Base	Additive	Time/h	Temp./℃	Yield/%
1	NaO^tBu	—	0.25	25	90
2	NaHMDS	—	0.25	25	87
3	NaOMe	—	24	50	51 (71)^a
4	NaOH	—	24	50	0 (70)^b
5	NaOPh	—	72	70	0
6	NBu₄OMe	—	72	50	0
7	NBu₄OMe	NaOAr_F	72	50	47
8	DBU	—	72	70	0
9	DBU	NaOAr_F	72	70	0
10	P1	—	72	50	0
11	P1	NaOAr_F	72	50	40

Table 1. Base-mediated transformation of [Ni{(CH2)2CO2}- (dtbpe)] into [Ni(η2-CH2=CHCO2Na)(dtbpe)]

Scheme 11. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of base

Scheme 12. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of LiI

Scheme 13. Cleavage of nickelalactone under the action of base

Scheme 14. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of base

Scheme 15. Production of macrocyclic diphosphine ligands

Scheme 16. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of base

Figure 5. Novel bisphosphine ligands

Scheme 17. The release of acrylates in the palladium center

Scheme 18. Coupling mechanism of CO2/C2H4 under the action of palladium-based catalyst

Entry^a	Ligand	TON^c	Pd leaching/(mg•L^–1)
1^b	none	0	n.d.^d
2	PCy₃	0	<1
3	dcpm	0	13
4	dcpe	106	1
5	dcpp	22	<1
6	dcpb	9	<1
7	dppe	0	<1
8	dmpe	0	49
9	dtbpe	17	14

Table 2. Direct production of acrylates by CO2/C2H4 in the presence of bases under different ligand conditions

Scheme 19. Coupling mechanism of CO2/C2H4 under the action of Ruthenium-based catalyst

Scheme 20. Coupling mechanism of CO2/C2H4 under the action of iron-based catalyst

References 66

[1]	Park, C.; Lee, Y. T.; Lee, S. H. Atmos. Environ. 2021, 252, 118340. doi: 10.1016/j.atmosenv.2021.118340
[2]	Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kühn, F. E. Angew. Chem., nt. Ed. 2011, 50, 8510.
[3]	Mikkelsen, M.; Jorgensen, M.; Krebs, F. C. Energy Environ. Sci. 2010, 3, 43. doi: 10.1039/B912904A
[4]	Aresta, M.; Dibenedetto, A.; Angelini, A. Chem. Rev. (Washington, DC, U. S.) 2014, 114, 1709. doi: 10.1021/cr4002758
[5]	Yi, Y. P.; Hang, W.; Xi, C. J. Chin. J. Org. Chem. 2021, 41, 80. (in Chinese) doi: 10.6023/cjoc202007013
	( 易雅平, 杭炜, 席婵娟, 有机化学, 2021, 41, 80.) doi: 10.6023/cjoc202007013
[6]	Liang, B, L.; Duan, H, M.; Hou, B, L.; Su, X.; Huang, Y, Q.; Wang, A, Q.; Wang, X, D.; Zhang, T. Chem. Ind. Eng. Prog. 2015, 34, 3746. (in Chinese)
	( 梁兵连, 段洪敏, 侯宝林, 苏雄, 黄延强, 王爱琴, 王晓东, 张涛, 化工进展, 2015, 34, 3746.)
[7]	Zhang, W. Z.; Zhang, N.; Guo, X. C.; Lu, X. B. Chin. J. Org. Chem. 2017, 37, 1309. (in Chinese) doi: 10.6023/cjoc201701031
	( 张文珍; 张宁; 郭春晓; 吕小兵, 有机化学, 2017, 37, 1309.)
[8]	Chen, K. H.; Li, H. R.; He, L. N. Chin. J. Org. Chem. 2020, 40, 2195. (in Chinese) doi: 10.6023/cjoc202004030
	( 陈凯宏, 李红茹, 何良年, 有机化学, 2020, 40, 2195.) doi: 10.6023/cjoc202004030
[9]	Zhang, Y.-G.; Riduan, S. N. Angew. Chem., Int. Ed. 2011, 50, 6210. doi: 10.1002/anie.201101341
[10]	Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. (Washington, DC, U. S.) 2007, 107, 2365. doi: 10.1021/cr068357u
[11]	Tortajada, A.; Julia-Hernandez, F.; Boerjesson, M.; Moragas, T.; Martin, R. Angew. Chem., Int. Ed. 2018, 57, 15948. doi: 10.1002/anie.201803186
[12]	Xu, P.; Wang, S. Y.; Fang, Y.; Ji, S. J. Chin. J. Org. Chem. 2018, 38, 1626. (in Chinese) doi: 10.6023/cjoc201801046
	( 徐佩, 汪顺义, 方毅, 纪顺俊, 有机化学, 2018, 38, 1626.) doi: 10.6023/cjoc201801046
[13]	Tappe, N. A.; Reich, R. M.; D'Elia, V.; Kühn, F. E. Dalton Trans. 2018, 47, 13281. doi: 10.1039/C8DT02346H
[14]	Anthofer, M. H.; Wilhelm, M. E.; Cokoja, M.; Markovits, I. I. E.; Poethig, A.; Mink, J.; Herrmann, W. A.; Kühn, F. E. Catal. Sci. Technol. 2014, 4, 1749. doi: 10.1039/c3cy01024d
[15]	Dutta, B.; Sofack-Kreutzer, J.; Ghani, A. A.; D'Elia, V.; Pelletier, J. D. A.; Cokoja, M.; Kühn, F. E.; Basset, J.-M. Catal. Sci. Technol. 2014, 4, 1534. doi: 10.1039/C4CY00003J
[16]	Kissling, S.; Altenbuchner, P. T.; Lehenmeier, M. W.; Herdtweck, E.; Deglmann, P.; Seemann, U. B.; Rieger, B. Chem.-Eur. J. 2015, 21, 8148. doi: 10.1002/chem.201406055 pmid: 25900151
[17]	Gao, P.; Cui, X.; Zhong, L, S.; Sun, Y, H.. Chem. Ind. Eng. Prog. 2019, 38, 183. (in Chinese)
	( 高鹏, 崔勖, 钟良枢, 孙予罕, 化工进展, 2019, 38, 183.)
[18]	Li, J.; Deng, Y, Y.; Yang, L.; Cao, X. J. Chem. Ind. Eng. Prog. 2013, 32, 340. (in Chinese)
	( 李静, 邓廷云, 杨林, 曹建新, 化工进展, 2013, 32, 340.)
[19]	Sasaki, Y.; Inoue, Y.; Hashimoto, H. J. Chem. Soc., Chem. Commun. 1976, 605.
[20]	Inoue, Y.; Sasaki, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1978, 51, 2375. doi: 10.1246/bcsj.51.2375
[21]	Lejkowski, M. L.; Lindner, R.; Kageyama, T.; Bodizs, G. E.; Plessow, P. N.; Mueller, I. B.; Schaefer, A.; Rominger, F.; Hofmann, P.; Futter, C.; Schunk, S. A.; Limbach, M. Chem.-Eur. J. 2012, 18, 14017. doi: 10.1002/chem.201201757 pmid: 22996190
[22]	Brill, M.; Lazreg, F.; Cazin, C. S. J.; Nolan, S. P. Top. Organomet. Chem. 2016, 53, 225.
[23]	Hendriksen, C.; Pidko, E. A.; Yang, G.; Schaeffner, B.; Vogt, D. Chem.-Eur. J. 2014, 20, 12037. doi: 10.1002/chem.201404082 pmid: 25116123
[24]	Zhang, Z.; Guo, F.; Kühn, F. E.; Sun, J.; Zhou, M.; Fang, X. Appl. Organomet. Chem. 2017, 31, e3567. doi: 10.1002/aoc.3567
[25]	Hollering, M.; Dutta, B.; Kühn, F. E. Coord. Chem. Rev. 2016, 309, 51. doi: 10.1016/j.ccr.2015.10.002
[26]	Wang, X.; Wang, H.; Sun, Y. Chem 2017, 3, 211. doi: 10.1016/j.chempr.2017.07.006
[27]	Schaub, T. Top. Organomet. Chem. 2019, 65, 253.
[28]	Lee, S. Y. T.; Ghani, A. A.; D'Elia, V.; Cokoja, M.; Herrmann, W. A.; Basset, J.-M.; Kühn, F. E. New J. Chem. 2013, 37, 3512. doi: 10.1039/c3nj00693j
[29]	Kunihiro, K.; Heyte, S.; Paul, S.; Roisnel, T.; Carpentier, J.-F.; Kirillov, E. Chem.-Eur. J. 2021, 27, 3997. doi: 10.1002/chem.202005083 pmid: 33378130
[30]	Kraus, S.; Rieger, B. Top. Organomet. Chem. 2016, 53, 199.
[31]	Tsuji, Y.; Fujihara, T. Chem. Commun. (Cambridge, U. K.) 2012, 48, 9956. doi: 10.1039/c2cc33848c
[32]	Hoberg, H.; Schaefer, D. J. Organomet. Chem. 1983, 251, C51. doi: 10.1016/S0022-328X(00)98789-8
[33]	Papai, I.; Schubert, G.; Mayer, I.; Besenyei, G.; Aresta, M. Organometallics 2004, 23, 5252. doi: 10.1021/om049496+
[34]	Dreissig, W.; Dietrich, H. Acta Crystallogr., Sect. B: Struct. Sci., Cryst. Eng. Mater. 1981, B37, 931.
[35]	Fischer, R.; Langer, J.; Malassa, A.; Walther, D.; Goerls, H.; Vaughan, G. Chem. Commun. (Cambridge, U. K.) 2006, 2510.
[36]	Graham, D. C.; Mitchell, C.; Bruce, M. I.; Metha, G. F.; Bowie, J. H.; Buntine, M. A. Organometallics 2007, 26, 6784. doi: 10.1021/om700592w
[37]	Li, Y.; Liu, Z.; Cheng, R.; Liu, B. ChemCatChem 2018, 10, 1420. doi: 10.1002/cctc.201701763
[38]	Al-Ghamdi, M.; Vummaleti, S. V. C.; Falivene, L.; Pasha, F. A.; Beetstra, D. J.; Cavallo, L. Organometallics 2017, 36, 1107. doi: 10.1021/acs.organomet.6b00905
[39]	Aresta, M.; Pastore, C.; Giannoccaro, P.; Kovacs, G.; Dibenedetto, A.; Papai, I. Chem.-Eur. J. 2007, 13, 9028. doi: 10.1002/chem.200700532
[40]	Bruckmeier, C.; Lehenmeier, M. W.; Reichardt, R.; Vagin, S.; Rieger, B. Organometallics 2010, 29, 2199. doi: 10.1021/om100060y
[41]	Lee, S. Y. T.; Cokoja, M.; Drees, M.; Li, Y.; Mink, J.; Herrmann, W. A.; Kühn, F. E. ChemSusChem 2011, 4, 1275. doi: 10.1002/cssc.201000445
[42]	Liang, L.-C.; Chien, P.-S.; Lee, P.-Y. Organometallics 2008, 27, 3082. doi: 10.1021/om701294a
[43]	Guo, W.; Michel, C.; Schwiedernoch, R.; Wischert, R.; Xu, X.; Sautet, P. Organometallics 2014, 33, 6369. doi: 10.1021/om5006808
[44]	Plessow, P. N.; Weigel, L.; Lindner, R.; Schaefer, A.; Rominger, F.; Limbach, M.; Hofmann, P. Organometallics 2013, 32, 3327. doi: 10.1021/om400262b
[45]	Jin, D.; Williard, P. G.; Hazari, N.; Bernskoetter, W. H. Chem.-Eur. J. 2014, 20, 3205. doi: 10.1002/chem.201304196
[46]	Huguet, N.; Jevtovikj, I.; Gordillo, A.; Lejkowski, M. L.; Lindner, R.; Bru, M.; Khalimon, A. Y.; Rominger, F.; Schunk, S. A.; Hofmann, P.; Limbach, M. Chem.-Eur. J. 2014, 20, 16858. doi: 10.1002/chem.201405528 pmid: 25359188
[47]	Knopf, I.; Tofan, D.; Beetstra, D.; Al-Nezari, A.; Al-Bahily, K.; Cummins, C. C. Chem. Sci. 2017, 8, 1463. doi: 10.1039/C6SC03614G
[48]	Li, Y.; Liu, Z.; Zhang, J.; Cheng, R.; Liu, B. ChemCatChem 2018, 10, 5669. doi: 10.1002/cctc.201801305
[49]	Hopkins, M. N.; Shimmei, K.; Uttley, K. B.; Bernskoetter, W. H. Organometallics 2018, 37, 3573. doi: 10.1021/acs.organomet.8b00260
[50]	Uttley, K. B.; Shimmei, K.; Bernskoetter, W. H. Organometallics 2020, 39, 1573. doi: 10.1021/acs.organomet.9b00708
[51]	Musco, A.; Perego, C.; Tartiari, V. Inorg. Chim. Acta 1978, 28, L147. doi: 10.1016/S0020-1693(00)87385-5
[52]	Langer, J.; Fischer, R.; Goerls, H.; Walther, D. Eur. J. Inorg. Chem. 2007, 2257.
[53]	Stieber, S. C. E.; Huguet, N.; Kageyama, T.; Jevtovikj, I.; Ariyananda, P.; Gordillo, A.; Schunk, S. A.; Rominger, F.; Hofmann, P.; Limbach, M. Chem. Commun. (Cambridge, U. K.) 2015, 51, 10907. doi: 10.1039/C5CC01932J
[54]	Manzini, S.; Huguet, N.; Trapp, O.; Schaub, T. Eur. J. Org. Chem. 2015, 2015, 7122. doi: 10.1002/ejoc.201501113
[55]	Manzini, S.; Cadu, A.; Schmidt, A.-C.; Huguet, N.; Trapp, O.; Paciello, R.; Schaub, T. ChemCatChem 2017, 9, 2269. doi: 10.1002/cctc.201601150
[56]	Li, B.; Kyran, S. J.; Yeung, A. D.; Bengali, A. A.; Darensbourg, D. J. Inorg. Chem. 2013, 52, 5438. doi: 10.1021/ic4003737
[57]	Ito, T.; Takahashi, K.; Iwasawa, N. Organometallics 2019, 38, 205. doi: 10.1021/acs.organomet.8b00789
[58]	Takahashi, K.; Hirataka, Y.; Ito, T.; Iwasawa, N. Organometallics 2020, 39, 1561. doi: 10.1021/acs.organomet.9b00659
[59]	Hoberg, H.; Jenni, K.; Angermund, K.; Krüger, C. Angew. Chem., Int. Ed. 1987, 26, 153.
[60]	Hanna, B. S.; MacIntosh, A. D.; Ahn, S.; Tyler, B. T.; Palmore, G. T. R.; Williard, P. G.; Bernskoetter, W. H. Organometallics 2014, 33, 3425. doi: 10.1021/om500324h
[61]	Alvarez, R.; Carmona, E.; Galindo, A.; Gutierrez, E.; Marin, J. M.; Monge, A.; Poveda, M. L.; Ruiz, C.; Savariault, J. M. Organometallics 1989, 8, 2430. doi: 10.1021/om00112a026
[62]	Alvarez, R.; Carmona, E.; Cole-Hamilton, D. J.; Galindo, A.; Gutierrez-Puebla, E.; Monge, A.; Poveda, M. L.; Ruiz, C. J. Am. Chem. Soc. 1985, 107, 5529. doi: 10.1021/ja00305a037
[63]	Bernskoetter, W. H.; Tyler, B. T. Organometallics 2011, 30, 520. doi: 10.1021/om100891m
[64]	Knopf, I.; Courtemanche, M.-A.; Cummins, C. C. Organometallics 2017, 36, 4834. doi: 10.1021/acs.organomet.7b00734
[65]	Yamashita, K.; Chatani, N. Synlett 2005, 919.
[66]	Aresta, M.; Quaranta, E. J. Organomet. Chem. 1993, 463, 215. doi: 10.1016/0022-328X(93)83420-Z

CO₂/C₂H₄耦合制备丙烯酸及其衍生物的研究进展

Advances in the Production of Acrylic Acid and Its Derivatives by CO₂/C₂H₄ Coupling

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CO2/C2H4耦合制备丙烯酸及其衍生物的研究进展