Tandem catalysis enables chlorine-containing waste as chlorination reagents.


Journal

Nature chemistry
ISSN: 1755-4349
Titre abrégé: Nat Chem
Pays: England
ID NLM: 101499734

Informations de publication

Date de publication:
23 Feb 2024
Historique:
received: 04 02 2023
accepted: 26 01 2024
medline: 24 2 2024
pubmed: 24 2 2024
entrez: 23 2 2024
Statut: aheadofprint

Résumé

Chlorinated compounds are ubiquitous. However, accumulation of chlorine-containing waste has a negative impact on human health and the environment due to the inapplicability of common disposal methods, such as landfill and incineration. Here we report a sustainable approach to valorize chlorine-containing hydrocarbon waste, including solids (chlorinated polymers) and liquids (chlorinated solvents), based on copper and palladium catalysts with a NaNO

Identifiants

pubmed: 38396160
doi: 10.1038/s41557-024-01462-8
pii: 10.1038/s41557-024-01462-8
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Informations de copyright

© 2024. The Author(s).

Références

Jiang, F. et al. N-terminal signal peptides facilitate the engineering of PVC complex as a potent protein delivery system. Sci. Adv. 8, eabm2343 (2022).
pubmed: 35486720 pmcid: 9054023 doi: 10.1126/sciadv.abm2343
Liu, D. et al. Standardized measurement of dielectric materials’ intrinsic triboelectric charge density through the suppression of air breakdown. Nat. Commun. 13, 6019 (2022).
pubmed: 36224185 pmcid: 9556570 doi: 10.1038/s41467-022-33766-z
Naclerio, N. D. et al. Controlling subterranean forces enables a fast, steerable, burrowing soft robot. Sci. Robot. 6, eabe2922 (2021).
pubmed: 34135117 doi: 10.1126/scirobotics.abe2922
Kim, J., Zhang, G., Shi, M. & Suo, Z. Fracture, fatigue, and friction of polymers in which entanglements greatly outnumber cross-links. Science 374, 212–216 (2021).
pubmed: 34618571 doi: 10.1126/science.abg6320
Frey, S. T. et al. Octopus-inspired adhesive skins for intelligent and rapidly switchable underwater adhesion. Sci. Adv. 8, eabq1905 (2022).
pubmed: 35857521 pmcid: 9278861 doi: 10.1126/sciadv.abq1905
Ferrer-Gago, F. J., Koh, L. Q. & Lane, D. P. Functionalized resins for the synthesis of peptide alcohols. Chem. Eur. J. 26, 379–383 (2020).
pubmed: 31609031 doi: 10.1002/chem.201903965
Zhang, D. et al. Identification, occurrence, and cytotoxicity of haloanilines: a new class of aromatic nitrogenous disinfection byproducts in chloraminated and chlorinated drinking water. Environ. Sci. Technol. 56, 4132–4141 (2022).
pubmed: 35302737 doi: 10.1021/acs.est.1c07375
Jordan, A., Stoy, P. & Sneddon, H. F. Chlorinated solvents: their advantages, disadvantages, and alternatives in organic and medicinal chemistry. Chem. Rev. 121, 1582–1622 (2021).
pubmed: 33351588 doi: 10.1021/acs.chemrev.0c00709
Jordan, A., Hall, C. G. J., Thorp, L. R. & Sneddon, H. F. Replacement of less-preferred dipolar aprotic and ethereal solvents in synthetic organic chemistry with more sustainable alternatives. Chem. Rev. 122, 6749–6794 (2022).
pubmed: 35201751 pmcid: 9098182 doi: 10.1021/acs.chemrev.1c00672
Dutta, P. et al. A case study in green chemistry: the reduction of hazardous solvents in an industrial R&D environment. Green Chem. 24, 3943–3956 (2022).
doi: 10.1039/D2GC00698G
Hossain, A., Bhattacharyya, A. & Reiser, O. Copper’s rapid ascent in visible-light photoredox catalysis. Science 364, eaav9713 (2019).
pubmed: 31048464 doi: 10.1126/science.aav9713
Forbes, K. C. & Jacobsen, E. N. Enantioselective hydrogen-bond-donor catalysis to access diverse stereogenic-at-P(V) compounds. Science 376, 1230–1236 (2022).
pubmed: 35679409 pmcid: 9427129 doi: 10.1126/science.abp8488
Bhutani, P. et al. U.S. FDA approved drugs from 2015–June 2020: a perspective. J. Med. Chem. 64, 2339–2381 (2021).
pubmed: 33617716 doi: 10.1021/acs.jmedchem.0c01786
Cao, H., Cheng, Q. & Studer, A. Radical and ionic meta-C–H functionalization of pyridines, quinolines, and isoquinolines. Science 378, 779–785 (2022).
pubmed: 36395213 doi: 10.1126/science.ade6029
Fink, E. A. et al. Structure-based discovery of nonopioid analgesics acting through the α2A-adrenergic receptor. Science 377, eabn7065 (2022).
pubmed: 36173843 pmcid: 10360211 doi: 10.1126/science.abn7065
Song, S. et al. DMSO-catalysed late-stage chlorination of (hetero)arenes. Nat. Catal. 3, 107–115 (2020).
doi: 10.1038/s41929-019-0398-0
Liew, Z. & Guo, P. Human health effects of chemical mixtures. Science 375, 720–721 (2022).
pubmed: 35175805 pmcid: 9805352 doi: 10.1126/science.abn9080
Atashgahi, S. et al. Prospects for harnessing biocide resistance for bioremediation and detoxification. Science 360, 743–746 (2018).
pubmed: 29773745 doi: 10.1126/science.aar3778
Cowell, A. N. et al. Mapping the malaria parasite druggable genome by using in vitro evolution and chemogenomics. Science. 359, 191–199 (2018).
pubmed: 29326268 pmcid: 5925756 doi: 10.1126/science.aan4472
Martín, A. J., Mondelli, C., Jaydev, S. D. & Pérez-Ramírez, J. Catalytic processing of plastic waste on the rise. Chem 7, 1487–1533 (2021).
doi: 10.1016/j.chempr.2020.12.006
Zhang, M.-Q. et al. Catalytic strategies for upvaluing plastic wastes. Chem 8, 2912–2923 (2022).
doi: 10.1016/j.chempr.2022.08.004
Ellis, L. D. et al. Chemical and biological catalysis for plastics recycling and upcycling. Nat. Catal. 4, 539–556 (2021).
doi: 10.1038/s41929-021-00648-4
Jehanno, C. et al. Critical advances and future opportunities in upcycling commodity polymers. Nature 603, 803–814 (2022).
pubmed: 35354997 doi: 10.1038/s41586-021-04350-0
Lee, K., Jing, Y., Wang, Y. & Yan, N. A unified view on catalytic conversion of biomass and waste plastics. Nat. Rev. Chem. 6, 635–652 (2022).
pubmed: 37117711 pmcid: 9366821 doi: 10.1038/s41570-022-00411-8
Chu, M., Liu, Y., Lou, X., Zhang, Q. & Chen, J. Rational design of chemical catalysis for plastic recycling. ACS Catal. 12, 4659–4679 (2022).
doi: 10.1021/acscatal.2c01286
Lee, W.-T. et al. Mechanistic classification and benchmarking of polyolefin depolymerization over silica-alumina-based catalysts. Nat. Commun. 13, 4850 (2022).
pubmed: 35977921 pmcid: 9385622 doi: 10.1038/s41467-022-32563-y
Zhang, F. et al. Polyethylene upcycling to long-chain alkylaromatics by tandem hydrogenolysis/aromatization. Science 370, 437–441 (2020).
pubmed: 33093105 doi: 10.1126/science.abc5441
Conk, R. J. et al. Catalytic deconstruction of waste polyethylene with ethylene to form propylene. Science 377, 1561–1566 (2022).
pubmed: 36173865 doi: 10.1126/science.add1088
Hou, Q. et al. Upcycling and catalytic degradation of plastic wastes. Cell Rep. Phys. Sci. 2, 100514 (2021).
doi: 10.1016/j.xcrp.2021.100514
Glas, D., Hulsbosch, J., Dubois, P., Binnemans, K. & De Vos, D. E. End-of-life treatment of poly(vinyl chloride) and chlorinated polyethylene by dehydrochlorination in ionic liquids. ChemSusChem 7, 610–617 (2014).
pubmed: 24420642 doi: 10.1002/cssc.201300970
Zhao, T. et al. A highly efficient approach for dehydrochlorinating polyvinyl chloride: catalysis by 1-butyl-3-methylimidazolium chloride. Green Chem. 12, 1062–1065 (2010).
doi: 10.1039/b927106f
Chen, Y. et al. Catalytic dechlorination and charring reaction of polyvinyl chloride by CuAl layered double hydroxide. Energy Fuels 32, 2407–2413 (2018).
doi: 10.1021/acs.energyfuels.7b03271
Kots, P. A., Vance, B. C., Quinn, C. M., Wang, C. & Vlachos, D. G. A two-stage strategy for upcycling chlorine-contaminated plastic waste. Nat. Sustain. 6, 1258–1267 (2023).
doi: 10.1038/s41893-023-01147-z
Fagnani, D. E., Kim, D., Camarero, S. I., Alfaro, J. F. & McNeil, A. J. Using waste poly(vinyl chloride) to synthesize chloroarenes by plasticizer-mediated electro(de)chlorination. Nat. Chem. 15, 222–229 (2022).
pubmed: 36376389 doi: 10.1038/s41557-022-01078-w
Alberini, A. & Bartholomew, J. The determinants of hazardous waste disposal choice: an empirical analysis of halogenated solvent waste shipments. Contemp. Econ. Policy 17, 309–320 (1999).
doi: 10.1111/j.1465-7287.1999.tb00684.x
Pekelney, D. Hazardous waste generation, transportation, reclamation, and disposal: California’s manifest system and the case of halogenated solvients. J. Hazard. Mater. 23, 293–315 (1990).
doi: 10.1016/0304-3894(90)85047-7
Gan, G. et al. Nature of intrinsic defects in carbon materials for electrochemical dechlorination of 1,2-dichloroethane to ethylene. ACS Catal. 11, 14284–14292 (2021).
doi: 10.1021/acscatal.1c03701
Choi, C. et al. Efficient electrocatalytic valorization of chlorinated organic water pollutant to ethylene. Nat. Nanotechnol. 18, 160–167 (2022).
pubmed: 36536043 doi: 10.1038/s41565-022-01277-z
Whitfield, S. R. & Sanford, M. S. Reactivity of Pd(II) complexes with electrophilic chlorinating reagents: isolation of Pd(IV) products and observation of C−Cl bond-forming reductive elimination. J. Am. Chem. Soc. 129, 15142–15143 (2007).
pubmed: 18004863 doi: 10.1021/ja077866q
Kakiuchi, F. et al. Palladium-catalyzed aromatic C−H halogenation with hydrogen halides by means of electrochemical oxidation. J. Am. Chem. Soc. 131, 11310–11311 (2009).
pubmed: 19637871 doi: 10.1021/ja9049228
Powers, D. C., Benitez, D., Tkatchouk, E., Goddard, W. A. III & Ritter, T. Bimetallic reductive elimination from dinuclear Pd(III) complexes. J. Am. Chem. Soc. 132, 14092–14103 (2010).
pubmed: 20858006 pmcid: 2954233 doi: 10.1021/ja1036644
Petrone, D. A., Ye, J. & Lautens, M. Modern transition-metal-catalyzed carbon–halogen bond formation. Chem. Rev. 116, 8003–8104 (2016).
pubmed: 27341176 doi: 10.1021/acs.chemrev.6b00089
Liu, M. et al. Nitrogen dioxide catalyzed aerobic oxidative cleavage of C(OH)–C bonds of secondary alcohols to produce acids. Angew. Chem. Int. Ed. Engl. 58, 17393–17398 (2019).
pubmed: 31507019 doi: 10.1002/anie.201908788
Liu, M. et al. Aerobic oxidative cleavage and esterification of C(OH)–C bonds. Chem 6, 3288–3296 (2020).
doi: 10.1016/j.chempr.2020.09.006
Liu, M., Han, B. & Dyson, P. J. Simultaneous generation of methyl esters and CO in lignin transformation. Angew. Chem. Int. Ed. Engl. 61, e202209093 (2022).
pubmed: 35979750 pmcid: 9826404 doi: 10.1002/anie.202209093
Liu, M. & Dyson, P. J. Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling. Nat. Commun. 14, 2830 (2023).
pubmed: 37217549 pmcid: 10203214 doi: 10.1038/s41467-023-38534-1
McGivern, W. S., Derecskei-Kovacs, A., North, S. W. & Francisco, J. S. Computationally efficient methodology to calculate C−H and C−X (X = F, Cl, and Br) bond dissociation energies in haloalkanes. J. Phys. Chem. A 104, 436–442 (2000).
doi: 10.1021/jp993275d
Jaworski, J. S., Cembor, M. & Koliński, M. Electrostatic model of bond dissociation energies in polyhalogen methanes. J. Phys. Org. Chem. 19, 276–280 (2006).
doi: 10.1002/poc.1058
Liu, M., Yang, X. & Dyson, P. J. Chlorination of arenes via the degradation of toxic chlorophenols. Proc. Natl Acad. Sci. USA. 119, e2122425119 (2022).
pubmed: 35588450 pmcid: 9173806 doi: 10.1073/pnas.2122425119
Wang, D., Weinstein, A. B., White, P. B. & Stahl, S. S. Ligand-promoted palladium-catalyzed aerobic oxidation reactions. Chem. Rev. 118, 2636–2679 (2018).
pubmed: 28975795 doi: 10.1021/acs.chemrev.7b00334
Liu, F. et al. Transesterification catalyzed by ionic liquids on superhydrophobic mesoporous polymers: heterogeneous catalysts that are faster than homogeneous catalysts. J. Am. Chem. Soc. 134, 16948–16950 (2012).
pubmed: 23009896 doi: 10.1021/ja307455w
van Spronsen, M. A., Frenken, J. W. M. & Groot, I. M. N. Surface science under reaction conditions: CO oxidation on Pt and Pd model catalysts. Chem. Soc. Rev. 46, 4347–4374 (2017).
pubmed: 28589194 doi: 10.1039/C7CS00045F
Pearson, D. M., Conley, N. R. & Waymouth, R. M. Palladium-catalyzed carbonylation of diols to cyclic carbonates. Adv. Synth. Catal. 353, 3007–3013 (2011).
doi: 10.1002/adsc.201100240
Varga, M. et al. Adsorbed eutectic GaIn structures on a neoprene foam for stretchable MRI coils. Adv. Mater. 29, 1703744 (2017).
doi: 10.1002/adma.201703744
Zhang, W., Zhang, T., Jiang, N. & Zhang, T. Chemical modification of neoprene rubber by grafting cardanol, a versatile renewable materials from cashew industry. J. Polym. Res. 27, 163 (2020).
doi: 10.1007/s10965-020-02122-4
Genuino, H. C., Pilar Ruiz, M., Heeres, H. J. & Kersten, S. R. A. Pyrolysis of mixed plastic waste: predicting the product yields. Waste Manag. 156, 208–215 (2023).
pubmed: 36493664 doi: 10.1016/j.wasman.2022.11.040
Yusuf, A. A. et al. Investigating the influence of plastic waste oils and acetone blends on diesel engine combustion, pollutants, morphological and size particles: dehalogenation and catalytic pyrolysis of plastic waste. Energy Convers. Manag. 291, 117312 (2023).
doi: 10.1016/j.enconman.2023.117312
Ceballos, D. M. et al. Perchloroethylene and dry cleaning: it’s time to move the industry to safer alternatives. Front. Public Health 9, 638082 (2021).
pubmed: 33748070 pmcid: 7973082 doi: 10.3389/fpubh.2021.638082
Davenport, E., Negru, D. E., Badman, G., Lindsay, D. M. & Kerr, W. J. Robust and general late-stage methylation of aryl chlorides: application to isotopic labeling of drug-like scaffolds. ACS Catal. 13, 11541–11547 (2023).
pubmed: 37671180 pmcid: 10476154 doi: 10.1021/acscatal.3c02761
Alder, C. M. et al. Updating and further expanding GSK’s solvent sustainability guide. Green Chem. 18, 3879–3890 (2016).
doi: 10.1039/C6GC00611F
Vyas, P. V., Bhatt, A. K., Ramachandraiah, G. & Bedekar, A. V. Environmentally benign chlorination and bromination of aromatic amines, hydrocarbons and naphthols. Tetrahedron Lett. 44, 4085–4088 (2003).
doi: 10.1016/S0040-4039(03)00834-7
Firouzabadi, H., Iranpoor, N. & Shiri, M. Direct and regioselective iodination and bromination of benzene, naphthalene and other activated aromatic compounds using iodine and bromine or their sodium salts in the presence of the Fe(NO
doi: 10.1016/j.tetlet.2003.09.189
Kalyani, D., Dick, A. R., Anani, W. Q. & Sanford, M. S. A simple catalytic method for the regioselective halogenation of arenes. Org. Lett. 8, 2523–2526 (2006).
pubmed: 16737304 doi: 10.1021/ol060747f
Misal, B., Palav, A., Ganwir, P. & Chaturbhuj, G. Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI). Tetrahedron Lett. 63, 152689 (2021).
doi: 10.1016/j.tetlet.2020.152689
Sekulic, A. et al. Efficacy and safety of vismodegib in advanced basal-cell carcinoma. N. Engl. J. Med. 366, 2171–2179 (2012).
pubmed: 22670903 pmcid: 5278761 doi: 10.1056/NEJMoa1113713
Yu, Q., Hu, L. A., Wang, Y., Zheng, S. & Huang, J. Directed meta-selective bromination of arenes with ruthenium catalysts. Angew. Chem. Int. Ed. Engl. 54, 15284–15288 (2015).
pubmed: 26517831 doi: 10.1002/anie.201507100
Umei, K. et al. Identification of novel 1,2,3,6-tetrahydropyridyl-substituted benzo[d]thiazoles: lead generation and optimization toward potent and orally active EP
pubmed: 28483455 doi: 10.1016/j.bmc.2017.04.028
Dhanya, R.-P. et al. Design and synthesis of an orally active metabotropic glutamate receptor subtype-2 (mGluR2) positive allosteric modulator (PAM) that decreases cocaine self-administration in rats. J. Med. Chem. 54, 342–353 (2011).
pubmed: 21155570 doi: 10.1021/jm1012165
Eytel, L. M., Fargher, H. A., Haley, M. M. & Johnson, D. W. The road to aryl CH⋯anion binding was paved with good intentions: fundamental studies, host design, and historical perspectives in CH hydrogen bonding. Chem. Commun. 55, 5195–5206 (2019).
doi: 10.1039/C9CC01460H
Wang, L., Zhang, R.-Z., Deng, R. & Luo, Y.-H. Oxygen-induced enhancement in low-temperature dechlorination of PVC: an experimental and DFT study on the oxidative pyrolysis process. ACS Sustain. Chem. Eng. 9, 2835–2843 (2021).
doi: 10.1021/acssuschemeng.0c08667
Zhang, R.-Z., Wang, L.-Z., Deng, R.-Q. & Luo, Y.-H. Inhibition on chloroaromatics during thermal conversion processes of municipal solid waste by oxygen-induced low-temperature pre-dechlorination and hydrogen-assisted in-situ Cl capture. Fuel Process. Technol. 237, 107445 (2022).
doi: 10.1016/j.fuproc.2022.107445
Song, B., Zheng, X., Mo, J. & Xu, B. Palladium-catalyzed monoselective halogenation of C–H bonds: efficient access to halogenated arylpyrimidines using calcium halides. Adv. Synth. Catal. 352, 329–335 (2010).
doi: 10.1002/adsc.200900778
Piera, J. & Bäckvall, J.-E. Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer—a biomimetic approach. Angew. Chem. Int. Ed. Engl. 47, 3506–3523 (2008).
pubmed: 18383499 doi: 10.1002/anie.200700604
Pye, D. R. & Mankad, N. P. Bimetallic catalysis for C–C and C–X coupling reactions. Chem. Sci. 8, 1705–1718 (2017).
pubmed: 29780450 pmcid: 5933431 doi: 10.1039/C6SC05556G
Kim, U. B., Jung, D. J., Jeon, H. J., Rathwell, K. & Lee, S.-G. Synergistic dual transition metal catalysis. Chem. Rev. 120, 13382–13433 (2020).
pubmed: 33251788 doi: 10.1021/acs.chemrev.0c00245
Dyson, P. J. & Jessop, P. G. Solvent effects in catalysis: rational improvements of catalysts via manipulation of solvent interactions. Catal. Sci. Technol. 6, 3302–3316 (2016).
doi: 10.1039/C5CY02197A
Chen, X., Hao, X.-S., Goodhue, C. E. & Yu, J.-Q. Cu(II)-catalyzed functionalizations of aryl C−H bonds using O
pubmed: 16719450 doi: 10.1021/ja061715q
Yang, L., Lu, Z. & Stahl, S. S. Regioselective copper-catalyzed chlorination and bromination of arenes with O
doi: 10.1039/b915487f
Chiodi, D. & Ishihara, Y. ‘Magic chloro’: profound effects of the chlorine atom in drug discovery. J. Med. Chem. 66, 5305–5331 (2023).
pubmed: 37014977 doi: 10.1021/acs.jmedchem.2c02015
Worrell, E., Phylipsen, D., Einstein, D. & Martin, N. Energy Use and Energy Intensity of the U.S. Chemical Industry Technical Report LBNL-44314 (US EPA, 2000).

Auteurs

Mingyang Liu (M)

Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland.

Xinbang Wu (X)

Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland.

Paul J Dyson (PJ)

Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland. paul.dyson@epfl.ch.

Classifications MeSH