دورية أكاديمية
أعرض في EDS

Production of Biomass-Derived p-Hydroxybenzamide: Synthesis of p-Aminophenol and Paracetamol.

التفاصيل البيبلوغرافية
العنوان: Production of Biomass-Derived p-Hydroxybenzamide: Synthesis of p-Aminophenol and Paracetamol.
المؤلفون: Karlen SD; Wisconsin Energy Institute and the DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, 1552 University Avenue, Madison, WI 53726, USA., Timokhin VI; Wisconsin Energy Institute and the DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, 1552 University Avenue, Madison, WI 53726, USA., Sener C; Wisconsin Energy Institute and the DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, 1552 University Avenue, Madison, WI 53726, USA., Mobley JK; Wisconsin Energy Institute and the DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, 1552 University Avenue, Madison, WI 53726, USA., Runge T; Wisconsin Energy Institute and the DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, 1552 University Avenue, Madison, WI 53726, USA.; Department of Biosystems Engineering, University of Wisconsin-Madison., Ralph J; Wisconsin Energy Institute and the DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, 1552 University Avenue, Madison, WI 53726, USA.; Department of Biosystems Engineering, University of Wisconsin-Madison.; Department of Biochemistry, University of Wisconsin-Madison.
المصدر: ChemSusChem [ChemSusChem] 2024 Apr 22; Vol. 17 (8), pp. e202400234.
نوع المنشور: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101319536 Publication Model: Print Cited Medium: Internet ISSN: 1864-564X (Electronic) Linking ISSN: 18645631 NLM ISO Abbreviation: ChemSusChem Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Weinheim : Wiley-VCH
مواضيع طبية MeSH: Aminophenols*/chemistry , Acetaminophen*/chemistry , Acetaminophen*/chemical synthesis , Biomass*, Benzamides/chemistry ; Benzamides/chemical synthesis ; Chemistry Techniques, Synthetic ; Parabens/chemistry
مستخلص: As we work to transition the modern society that is based on non-renewable chemical feedstocks to a post-modern society built around renewable sources of energy, fuels, and chemicals, there is a need to identify the renewable resources and processes for converting them to platform chemicals. Herein, we explore a strategy for utilizing the p-hydroxybenzoate in biomass feedstocks (e. g., poplar and palm trees) and converting it into a portfolio of commodity chemicals. The targeted bio-derived product in the first processing stage is p-hydroxybenzamide produced from p-hydroxybenzoate esters found in the plant. In the second stage a continuous reaction process converts the p-hydroxybenzamide to p-aminophenol via the Hofmann rearrangement and recovers the unreacted p-hydroxybenzamide. In the third stage the p-aminophenol can be acetylated to form paracetamol, which is readily isolated by liquid/liquid extraction at >95 % purity and an overall p-hydroxybenzamide-to-paracetamol process yield of ~90 %. We explore how utilization of protecting groups alters the challenges in this process and expands the portfolio of possible products to include p-(methoxymethoxy)aniline and N-acetyl-p-(methoxymethoxy)aniline. These target compounds could become value-added renewably-sourced platform chemicals that could be used to produce biodegradable plastics, pigments, and pharmaceuticals.
(© 2024 The Authors. ChemSusChem published by Wiley-VCH GmbH.)
References: .
“Paracetamol Market - Growth, Trends, COVID-19 Impact, and Forecasts (2023-2028),” Research and Markets 2021;.
“Global paracetamol market insights and forecast to 2028,” Market Reports World 2022.
 .
K. G. Davenport, C. B. Hilton, Process for producing N-acyl-hydroxy aromatic amines. U. S. Patent 1985, 4 (524), 217 A;.
G. Wilbert, J. D. Angelis, N-Acetyl-p-aminophenol. U. S. Paten 1961, 2 (998), 450;.
S. Gopinathan, C. Copinayhan, J. Kuruvilla, S. A. Parody, P. Ratnasamy, Process for the preparation of N-acetylaminphenols. U. S. Patent 1999, 5 (856), 575.
 .
E. Blondiaux, J. Bomon, M. Smolen, N. Kaval, F. Lemiere, S. Sergeyev, L. Diels, B. Sels, B. U. W. Maes, ACS Sustainable Chem. Eng. 2019, 7, 6906–6916, 10.1021/acssuschemeng.8b06467;.
R. Joncour, N. Duguet, E. Metay, A. Ferreira, M. Lemaire, Green Chem. 2014, 16, 2997–3002, 10.1039/c4gc00166d;.
J. Park, M. A. Kelly, J. X. Kang, S. S. Seemakurti, J. L. Ramirez, M. C. Hatzell, C. Sievers, A. S. Bommarius, Green Chemistry 2021, 23, 7488–7498, 10.1039/d1gc02158c;.
H. Y. Chuang, M. Schupp, R. Meyrelles, B. Maryasin, N. Maulide, Angew. Chem. Int. Ed. Engl. 2021, 60, 13778–13782, 10.1002/anie.202100801;.
M. Guidi, S. Moon, L. Anghileri, D. Cambie, P. H. Seeberger, K. Gilmore, React. Chem. Eng. 2021, 6, 220–224, 10.1039/d0re00445f;.
J. D. Tibbetts, M. Hutchby, W. B. Cunningham, R. S. L. Chapman, G. Kociok-Kohn, M. G. Davidson, S. D. Bull, ChemSusChem. 2023, e202300670, 1–10, 10.1002/cssc.202300670;.
M. Takasaki, Y. Motoyama, K. Higashi, S. H. Yoon, I. Mochida, H. Nagashima, Org. Lett. 2008, 10, 1601–1604, 10.1021/ol800277a;.
M. Li, L. Hu, X. Cao, H. Hong, J. Lu, H. Gu, Chemistry 2011, 17, 2763–2768, 10.1002/chem.201002801.
“Global aminophenol market by type (p-aminophenol, m-aminophenol, and o-aminophenol), application (dye intermediate, synthesis precursor, fluorescent stabilizers), end-use industry, and geography - forecast to 2027,” Research and Markets 2022.
Z. Sun, B. Fridrich, A. de Santi, S. Elangovan, K. Barta, Chem. Rev. 2018, 118, 614–678, 10.1021/acs.chemrev.7b00588.
G. Fuchs, M. Boll, J. Heider, Nat. Rev. Microbiol. 2011, 9, 803–816, 10.1038/nrmicro2652.
 .
D. C. C. Smith, Journal of the Chemical Society 1955, 2347–2351, 10.1039/JR9550002347;.
C. J. Venverloo, Holzforschung 1971, 25, 18–24;.
L. L. Landucci, G. C. Deka, D. N. Roy, Holzforschung 1992, 46, 505–511, 10.1515/hfsg.1992.46.6.505.
 .
I. A. Pearl, D. L. Beyer, D. Laskowski, Tappi 1959, 42, 779–782;.
Y. Tomimura, Japan Agricultural Research Quarterly 1992, 25, 283–288;.
R. C. Sun, J. M. Fang, J. Tomkinson, J. Wood Chem. Technol. 1999, 19, 335–356, 10.1080/02773819909349616;.
J. Rencoret, J. Ralph, G. Marques, A. Gutiérrez, Á. T. Martínez, J. C. del Río, J. Agric. Food Chem. 2013, 61, 2434–2445, 10.1021/jf304686x.
T. Hibino, D. Shibata, T. Ito, D. Tsuchiya, T. Higuchi, B. Pollet, C. Lapierre, Phytochemistry 1994, 37, 445–448, 10.1016/0031-9422(94)85076-3.
J. Rencoret, G. Marques, O. Serrano, J. Kaal, A. T. Martínez, J. C. del Río, A. Gutiérrez, ACS Sustainable Chem. Eng. 2020, 8, 12521–12533, 10.1021/acssuschemeng.0c03502.
L. de Vries, H. A. MacKay, R. A. Smith, Y. Mottiar, S. D. Karlen, F. Unda, E. Muirragui, C. Bingman, K. Vander Meulen, E. T. Beebe, B. G. Fox, J. Ralph, S. D. Mansfield, Plant Physiol. 2022, 188, 1014–1027, 10.1093/plphys/kiab546.
F. Lu, S. D. Karlen, M. Regner, H. Kim, S. A. Ralph, R.-c. Sun, K.-i. Kuroda, M. A. Augustin, R. Mawson, H. Sabarez, T. Singh, G. Jimenez-Monteon, S. Hill, P. J. Harris, W. Boerjan, S. D. Mansfield, J. Ralph, BioEnergy Res. 2015, 8, 934–952, 10.1007/s12155-015-9583-4.
 .
J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen, Chem. Rev. 2010, 110, 3552–3599, 10.1021/Cr900354u;.
W. Schutyser, T. Renders, S. Van den Bosch, S.-F. Koelewijn, G. T. Beckham, B. F. Sels, Chem. Soc. Rev. 2018, 427, 852–908, 10.1039/c7cs00566k.
“Global 4-hydroxybenzoic acid market 2023 by manufacturers, regions, type and application, forecast to 2029,” Market Research Reports 2023.
 .
D. M. Alonso, S. H. Hakim, S. Zhou, W. Won, O. Hosseinaei, J. Tao, V. Garcia-Negron, A. H. Motagamwala, M. A. Mellmer, K. Huang, C. J. Houtman, N. Labbe, D. P. Harper, C. Maravelias, T. Runge, J. A. Dumesic, Sci. Adv. 2017, 3 (e1603301), 1–7, 10.1126/sciadv.1603301;.
J. M. Perez, C. Sener, S. Misra, G. E. Umana, J. Coplien, D. Haak, Y. Li, C. T. Maravelias, S. D. Karlen, J. Ralph, T. J. Donohue, D. R. Noguera, Green Chem. 2022, 24, 2795–2811, 10.1039/d1gc03592d.
A. W. Hofmann, Ber. Dtsch. Chem. Ges. 1881, 14, 2725–2736, 10.1002/cber.188101402242.
M. S. Kharasch, J. Am. Chem. Soc. 1921, 43, 1888–1894, 10.1021/ja01441a016.
 .
A. Yoshimura, M. W. Luedtke, V. V. Zhdankin, J. Org. Chem. 2012, 77, 2087–2091, 10.1021/jo300007c;.
R. M. Moriarty, C. J. Chany, R. K. Vaid, O. Prakash, S. M. Tuladhar, J. Org. Chem. 1993, 58, 2478–2482, 10.1021/jo00061a022.
H. E. Baumgarten, H. L. Smith, A. Staklis, J. Org. Chem. 1975, 40, 3554–3561, 10.1021/jo00912a019.
P. Radlick, L. R. Brown, Synthesis-Stuttgart 1974, 23, 290–292.
S. Kajigaeshi, K. Asano, S. Fujisaki, T. Kakinami, T. Okamoto, Chemistry Letters 1989, 18, 463-4-64, 10.1246/cl.1989.463.
 .
F. Lengfeld, J. Stieglitz, Ammerican Chemistry Journal 1893, 15, 504;.
C. H. Senanayake, L. E. Fredenburgh, R. A. Reamer, R. D. Larsen, T. R. Verhoeven, P. J. Reider, J. Am. Chem. Soc. 1994, 116, 7947–7948, 10.1021/ja00096a082;.
S.-s. Jew, H. G. Park, H.-J. Park, M.-s. Park, Y.-s. Cho, Tetrahedron Lett. 1990, 31, 1559–1562, 10.1016/0040-4039(90)80016-F.
 .
Z. Hodnik, L. P. Masic, T. Tomasic, D. Smodis, C. D'Amore, S. Fiorucci, D. Kikelj, J. Med. Chem. 2014, 57, 4819–4833, 10.1021/jm500351m;.
J. Park, C. H. Heo, H. M. Kim, J. I. Hong, Tetrahedron Lett. 2016, 57, 715–718, 10.1016/j.tetlet.2016.01.025;.
T. Peng, N. K. Wong, X. M. Chen, Y. K. Chan, D. H. H. Ho, Z. N. Sun, J. J. Hu, J. G. Shen, H. El-Nezami, D. Yang, J. Am. Chem. Soc. 2014, 136, 11728–11734, 10.1021/ja504624q;.
K. E. Knewtson, D. Rane, B. R. Peterson, ACS Chem. Biol. 2018, 13, 2595–2602, 10.1021/acschembio.8b00535.
معلومات مُعتمدة: DE-SC0018409 DE
فهرسة مساهمة: Keywords: Biomass; amination; green chemistry; rearrangement; renewable resources
المشرفين على المادة: 0 (Aminophenols)
362O9ITL9D (Acetaminophen)
R7P8FRP05V (4-aminophenol)
0 (Benzamides)
0 (Parabens)
تواريخ الأحداث: Date Created: 20240305 Date Completed: 20240426 Latest Revision: 20240426
رمز التحديث: 20240426
DOI: 10.1002/cssc.202400234
PMID: 38441462
قاعدة البيانات: MEDLINE
الوصف
تدمد:1864-564X
DOI:10.1002/cssc.202400234