Abstract
The literature on the existing processes for the preparation of an important organic product, methacrylic acid and its ester, methyl methacrylate is analyzed. It is shown that the main method of their industrial production are synthesis from acetone and hydrocyanic acid (acetonecyanohydrin) and catalytic syntheses from petrochemical feedstocks (ethylene, propylene and isobutylene).
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REFERENCES
Global Market Analysts. Methyl Methacrylate Market Trends. http://www.strategyr.com/MarketResearch/ MethylMethacrylateMMAMarketTrends.asp. Cited April 8, 2021.
Stepanenko, P., Chem. J., 2002, no. 4, pp. 50–51.
Darabi Mahboub, M.J., Patience, G.S., Dubois, J.L., Cavani, F., and Rostamizadeh, M., Chem. Soc. Rev., 2018, vol. 47, no. 20, pp. 7703–7738.
Lebeau, J., Efromson, J. P., and Lynch, M.D., Front. Bioeng. Biotechnol., 2020, vol. 8, p. 207. https://doi.org/10.3389/fbioe.2020.00207
Kirk-Othmer Encyclopedia of Chemical Technology, New York: Wiley, 2000, vol. 16, p. 242.
EP Patent 0433611, 1994.
EP Patent 0941984, 1999.
EVONIK Official Webcite. http://corporate.evonik.com/ en/investor-relations/news-reports/investor-relations-news/Pages/news-details.aspx?newsid=30165%. Cited April 8, 2021.
Kozhevnikov, I.V., Catalysis by Polyoxometalates, Chichester, UK: Wiley, 2002.
US Patent 4408079, 1983.
US Patent 4496770, 1985.
US Patent 4433174, 1984.
Cao, Y.-L., Wang, L., Zhou, L.-L., Xu, B.H., Diao, Y.-Y., and Zhang, S.-J., J. Ind. Eng. Chem., 2018, vol. 65, pp. 254–263.
Cao, Y.-L., Wang, L., Xu, B.H., and Zhang, S.-J., Chem. Eng. J., 2018, vol. 334, pp. 1657–1667.
Yasuda, S., Hirata, J., Kanno, M., Ninomiya, W., Otomo, R., and Kamiya, Y., Appl. Catal., A, 2019, vol. 570, pp. 164–172.
US Patent 3835185, 1974.
US Patent 4801571, 1989.
US Patent 4599144, 1986.
US Patent 474810, 1988.
US Patent 4410729, 1983.
Drent, E., Amoldy, P., and Budzelaar, P.H.M., J. Organomet. Chem., 1993, vol. 455, pp. 247–253.
US Patent 5158921, 1992.
US Patent 5099062, 1992.
US Patent 4739109, 1988.
EP Patent 279477, 1988.
EP Patent 271144, 1988.
US Patent 3812175, 1974.
US Patent 4354044, 1982.
US Patent 5166119, 1992.
EP Patent 450596, 1991.
EP Patent 58046, 1982.
EP Patent 361372, 1990.
US Patent 4532083, 1985.
US Patent 4473506, 1984.
Zhiznevskii, V.M., Gumenetskii, V.V., Bazhan, L.V., and Maikova, S.V., Katal. Neftekhim., 2001, no. 8, pp. 41–46.
Dalin, M.A., Mekhtiev, S.I., and Rasulbekova, T.I., Dokl. Akad. Nauk SSSR, 1964, vol. 154, no. 4, pp. 854–856.
Cavani, F., Catal. Today, 2010, vol. 157, pp. 8–15.
Cavani, F., Mezzogori, R., Pigamo, A., and Trifiró, F., Chemistry, 2000, vol. 3, pp. 523–531.
Sun, M., Zhang, J., Putaj, P., Caps, V., Lefebvre, F., Pelletier, J., and Basset, J-M., Chem. Rev., 2014, vol. 114, no. 2, pp. 981–1019.
Mizuno, N. and Yahiro, H., J. Phys. Chem. B, 1998, vol. 102, pp. 437–443.
Knapp, C., Ui, T., Nagai, K., and Mizuno, N., Catal. Today, 2001, vol. 71, nos. 1–2, pp. 111–119.
Pyo, S.-H., Dishisha, T., Dayankac, S., Gerelsaikhan, J., Lundmark, S., Rehnberg, N., and Hatti-Kaul, R., Green Chem., 2012, vol. 14, no. 7, pp. 1942–1948.
Mahboub, M.J.D., Wright, J., Boffito, D.C., Dubois, J.-L., and Patience, G.S., Appl. Catal., A, 2018, vol. 554, pp. 105–116.
US Patent 8241877, 2009.
Yu, A.-Q., Juwono, N.K.P., Foo, J.L., Leong, S.S.J., and Chang, M.W., Metab. Eng., 2016, vol. 34, pp. 36–43.
Xiong, M., Yu, P., Wang, J., and Zhang, K., AIMS Bioeng., 2015, vol. 2, no. 2, pp. 60–74.
Macho, V., Králik, M., Chromá, V., Cingelová, J., and Mikulec, J., Pet. Coal, 2004, vol. 46, no. 3, pp. 69–80.
Hevekerl, A., Kuenz, A., and Vorlop, K.-D., Appl. Microbiol. Biotechnol., 2014, vol. 98, no. 24, pp. 10005–10012.
Kuenz, A. and Krull, S., Appl. Microbiol. Biotechnol., 2018, vol. 102, no. 9, pp. 3901–3914.
Tehrani, H.H., Becker, J., Bator, I., Saur, K., Meyer, S., Lóia, A.C.R., Blank, L.M., and Wierckx, N., Biotechnol. Biofuels, 2019, vol. 12. https://doi.org/10.1186/s13068-019-1605-6
Thakur, N., Pandey, M.D., and Pandey, R., J. Solid State Chem., 2019, vol. 280, pp. 120987–12099.
Bohre, A., Novak, U., Grilc, M., and Likozar, B., Mol. Catal., 2019, vol. 476, pp. 110520–110526.
Bohre, A., Hočevar, B., Grilc, M., and Likozar, B., Appl. Catal., B, 2019, vol. 256, pp. 117889–117899.
US Patent 0094438, 2015.
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This work was performed as a part of the state task for the Boreskov Institute of Catalysis, project no. AAAA-A21-121011390007-7.
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Gogin, L.L., Zhizhina, E.G. & Pai, Z.P. Production of Methacrylic Acid and Metacrylates. Catal. Ind. 13, 125–131 (2021). https://doi.org/10.1134/S2070050421020057
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DOI: https://doi.org/10.1134/S2070050421020057