Tetrahydrofuran

1	Introduction
2	Physical Properties
3	Chemical Properties
4	Production
4.1	Acetylene/Formaldehyde
4.2	Propylene
4.2.1	Via Propylene Oxide
4.2.2	Via Allyl Acetate
4.3	Butadiene
4.4	Butane/Benzene
4.4.1	Via Maleic Anhydride
4.4.2	Via Maleic Acid
4.4.3	Via Dialkyl Maleate
4.5	Bio-based Feedstocks
4.5.1	Furfural
4.5.2	Fermentation Products
5	Specifications
6	Storage and Transport
7	Uses
8	Economic Aspects
9	Toxicology and Industrial Hygiene
	List of Abbreviations
	References

References

1Kudchadker, A.P., Kudchadker, S.A. and Wilhoit, R.C. (1978) Furan, Dihydrofuran Tetrahydrofuran, Thermodynamics Research Center, Texas A&M University, College Station, TX.
Google Scholar
2 BASF, (2023) Tetrahydrofuran, Technical Report, Ludwigshafen/Rhein.
Google Scholar
3Maria, P.C. and Gal, J.F. (1985) A Lewis Basicity Scale for Nonprotogenic Solvents: Enthalpies of Complex Formation with Boron Trifluoride in Dichloromethane, J. Phys. Chem. 89, 1296.
10.1021/j100253a048
CAS Web of Science® Google Scholar
4Eigenmann, H.K., Golden, D.M. and Benson, S.W. (1973) Revised Group Additivity Parameters for the Enthalpies of Formation of Oxygen-containing Organic Compounds, J. Phys. Chem. 77, 1687.
10.1021/j100632a019
CAS Web of Science® Google Scholar
5Dudev, T. and Lim, C. (1998) Ring Strain Energies from Ab Initio Calculations, J. Am. Chem. Soc. 120, 4450.
10.1021/ja973895x
CAS Web of Science® Google Scholar
6Meerwein, H., Delfs, D. and Morschel, H. (1960) Die Polymerisation des Tetrahydrofuran, Angew. Chem. 72, 927.
10.1002/ange.19600722402
CAS Web of Science® Google Scholar
7Hargis, I.G. and Melby, E.G. (1982) Poly(tetrahydrofuran), P. Dreyfuss, Gordon and Breach, New York, 1982, 306 pp, J. Polym. Sci. Polym. Lett. Ed. 20, 602.
10.1002/pol.1982.130201112
Google Scholar
8Garlotta, D. (2001) A Literature Review of Poly(Lactic Acid), J. Polym. Environ. 9, 63.
10.1023/A:1020200822435
CAS Web of Science® Google Scholar
9Cai, C.M., Zhang, T., Kumar, R. and Wyman, C.E. (2013) THF Co-Solvent Enhances Hydrocarbon Fuel Precursor Yields from Lignocellulosic Biomass, Green Chem. 15, 3140.
10.1039/c3gc41214h
CAS Web of Science® Google Scholar
10Laarhoven, L.J.J. and Mulder, P. (1997) α-C−H Bond Strengths in Tetralin and THF: Application of Competition Experiments in Photoacoustic Calorimetry, J. Phys. Chem. B 101, 73.
10.1021/jp960982n
CAS Web of Science® Google Scholar
11Rein, H. (1950) Über das Tetrahydrofuran-peroxyd, Angew. Chem. 62, 120.
10.1002/ange.19500620505
CAS Web of Science® Google Scholar
12Copenhaver, J.W. and Bigelow, M.H. (1949) Acetylene and Carbon Monoxide Chemistry, Reinhold Publ., New York.
Google Scholar
13 BASF, (1979) DE1043342 (J. Schneiders).
Google Scholar
14 BASF, (1979) DE2930144 (H. Mueller, H. Hoffmann, S. Winderl, and O.H. Huchler).
Google Scholar
15 I.G. Farbenindustrie, (1939) DE713565 (W. Reppe and H.-G. Trieschmann).
Google Scholar
16 Linde, (1991) DE4120446 (F. Wiessner).
Google Scholar
17 Sinopec, (2014) CN105642302 (Y. Zhang et al.)
Google Scholar
18 BASF, (1984) DE3432575 (H. Mueller and C. Palm).
Google Scholar
19 Du Pont, (1957) CA546591 (L.E. Baun Jr. and H.O. Wolf).
Google Scholar
20 Kuraray, Daicel Chemical Industries, (1983) JP60006630 (M. Matsumoto et al.).
Google Scholar
21Tamura, M. and Kumano, S. (1980) Chem. Econ. Eng. Rev. 12, 32.
CAS Google Scholar
22 Bayer, (1969) DE1911178 (W. Swodenk and G. Scharfe).
Google Scholar
23 Dairen Chemical, (1999) SG101929 (S.-C. Chen, L.-A. Hsu, F.-S. Lin, and P.-F. Jang).
Google Scholar
24 Dairen Chemical, (1994) US5426250 (S.-C. Chen, C.C. Chu, F.S. Lin, and J.Y. Chou).
Google Scholar
25 Mitsubishi Kasei, (1973) JPS504011 (T. Onoda et al.).
Google Scholar
26 Mitsubishi Kasei, (1974) JPS5129426 (J.U.N. Toriya and K.E.N. Shiraga).
Google Scholar
27 Mitsubishi Kasei, (1977) JP54032409 (I. Kasahara, K.E.N. Shiraga, Y. Tanabe, and J.U.N. Toriya).
Google Scholar
28 Princeton Chemical Research, (1964) US3293268 (R.I. Bergman and N.W. Frisch).
Google Scholar
29 Chevron Research, (1972) US3864280 (R.A. Schneider).
Google Scholar
30Arnold, S.C., Suciu, G.D., Verde, L. and Neri, A. (1985) Use Fluid Bed Reactor for Maleic Anhydride from Butane, Hydrocarb. Process. 64, 123.
CAS Google Scholar
31 Du Pont, (1985) US4668802 (R.M. Contractor).
Google Scholar
32 Huntsman, (1992) US5185455 (J.R. Ebner).
Google Scholar
33 BASF, (2000) DE10011309 (J. Weiguny, S. Storck, A. Tenten, and W. Ruppel).
Google Scholar
34 BASF, (2002) DE10235355 (J. Weiguny, W. Ruppel, and M. Duda).
Google Scholar
35 Technobell d.o.o. Koper, (2017) EP3360611 (G. Toth).
Google Scholar
36 Clariant, (2019) DE10201927788 (S. Boecklein, G. Mestl, and A. Adler).
Google Scholar
37Petts, R.W. and Waugh, K.C. (1982) Analysis of the Factors Affecting Selectivity in the Partial Oxidation of Benzene to Maleic Anhydride. Part 3.—Mechanism of Benzene Surface Oxidation on a Vanadium Pentoxide–Molybdenum Trioxide Catalyst, J. Chem. Soc. Faraday Trans. 1 Phys. Chem. Condens. Phases 78, 803.
CAS Google Scholar
38Chen, B. and Munson, E.J. (2002) Investigation of the Mechanism of n-Butane Oxidation on Vanadium Phosphorus Oxide Catalysts: Evidence from Isotopic Labeling Studies, J. Am. Chem. Soc. 124, 1638.
10.1021/ja010285v
CAS PubMed Web of Science® Google Scholar
39 BASF, (2000) DE10011307 (J. Weiguny, S. Storck, and A. Tenten).
Google Scholar
40 BASF, (2002) DE10211447 (J. Weiguny, S. Storck, M. Duda, and C. Dobner).
Google Scholar
41 BASF, (2005) DE102005031314 (G. Windecker et al.).
Google Scholar
42 BASF, (2000) DE10061556 (R.-H. Fischer et al.).
Google Scholar
43 BASF, (2000) DE10061553 (H. Borchert et al.).
Google Scholar
44 Standard Oil, (1989) US5055599 (J.R. Budge).
Google Scholar
45 BASF, (1998) BE1012274 (A. Bertola, T. Constantinescu, P. Raucq, and S. Cassarino).
Google Scholar
46 BASF, (2000) DE10061555 (H. Borchert et al.).
Google Scholar
47 Du Pont, (1983) US4550185 (M.A. Mabry, W.W. Prichard, and S.B. Ziemecki).
Google Scholar
48 American Lurgi, (1936) US2127716 (O. Brucke).
Google Scholar
49 Mitsubishi Petrochemical, (1968) JPS4830271 (T. Asano et al.).
Google Scholar
50 Standard Oil, (1987) US4827001 (T.G. Attig and A.M. Graham).
Google Scholar
51 BP America, (2004) US20060004212 (A. Bhattacharyya and M.D. Manila).
Google Scholar
52 Davy McKee, (1984) US4584419 (M. Sharif and K. Turner).
Google Scholar
53 Davy McKee, (1985) US4751334 (K. Turner et al.).
Google Scholar
54 Davy McKee, (1987) EP0277168 (K. Turner et al.).
Google Scholar
55 Bayer, (1987) DE3711155 (B. Makowka and H.-D. Block).
Google Scholar
56Schlander, J.H. and Turek, T. (1999) Gas-Phase Hydrogenolysis of Dimethyl Maleate to 1,4-Butanediol and γ-Butyrolactone Over Copper/Zinc Oxide Catalysts, Ind. Eng. Chem. Res. 38, 1264.
10.1021/ie980606k
CAS Web of Science® Google Scholar
57 JM Davy, (2004) EP1678117 (D.M. Sutton, G. Reed, and A.G. Hiles).
Google Scholar
58 Quaker Oats, (1928) US1906873 (F.N. Peters Jr.).
Google Scholar
59 Du Pont, (1959) US3007941 (H.B. Copelin and D.I. Garnett).
Google Scholar
60 Du Pont, (1956) US2846449 (W.H. Banford and M.M. Manes).
Google Scholar
61 CSIR, (2013) EP2951165 (C.V. Rode, N.S. Biradar, and A.M. Hengne).
Google Scholar
62Lange, J.-P. and Wadman, S.H. (2020) Furfural to 1,4-Butanediol/Tetrahydrofuran – A Detailed Catalyst and Process Design, ChemSusChem 13, 5329.
10.1002/cssc.202001376
CAS PubMed Web of Science® Google Scholar
63 BASF, (2008) EP2051972 (T. Wabnitz et al.).
Google Scholar
64 Dalian University of Technology, (2013) CN103113325 (Z. Liang, Z. Shao, C. Li, and Z. Xiao).
Google Scholar
65 BASF, (2016) WO2016/110556 (A. Duefert, R. Pinkos, and W.-S. Weissker).
Google Scholar
66 Genomatica, (2008) WO2008/115840 (M.J. Burk, S.J. Van Dien, A.P. Burgard, and W.E.I. Niu).
Google Scholar
67 Genomatica, (2010) WO2010/141780 (W. Clark, M. Japs, and M.J. Burk).
Google Scholar
68 U.S. Department of Labor, Occupational Safety and Health Administration, OSHA Occupational Chemical Database (2021) Tetrahydrofuran, Washington, DC.
Google Scholar
69Fowles, J., Boatman, R., Bootman, J., et al. (2013) A Review of the Toxicological and Environmental Hazards and Risks of Tetrahydrofuran, Crit. Rev. Toxicol. 43, 811.
10.3109/10408444.2013.836155
CAS PubMed Web of Science® Google Scholar
70 National Center for Biotechnology Information, NCBI Hazardous Substance Data Bank (2023) Tetrahydrofuran, Bethesda, MD.
Google Scholar

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