4,4'-Biphenol
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| Names | |
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| Preferred IUPAC name
[1,1′-Biphenyl]-4,4′-diol | |
| Other names
4,4′-Dihydroxybiphenyl 4,4′-Diphenol 4,4′-Biphenyldiol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.001 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H10O2 | |
| Molar mass | 186.210 g·mol−1 |
| Appearance | colorless or white solid |
| Melting point | 283 °C (541 °F; 556 K)[1] |
| Boiling point | Sublimes |
| Insoluble in water Soluble in ethanol and ether | |
| Hazards | |
| Flash point | > 93.3 °C (199.9 °F; 366.4 K) |
| Safety data sheet (SDS) | MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4,4′-Biphenol is an organic compound with the formula (C6H4OH)2/ It is one of three symmetrical isomers of biphenol. It is a colourless crystalline solid with a high melting point. It is primarily used in the production of polymers, particularly liquid crystals where it imparts high thermal stability, and PPSU-type polysulfone (also called polyphenylenesulfone, or Radel R).[2]
Synthesis
[edit]The industrial synthesis of 4,4′-biphenol was developed in the 1960s by Allan Hay, while working at the historic General Electric Research Laboratory.[3][4] As the direct oxidative coupling of phenol gives a mixture of isomers,[5][6] 4,4′-biphenol is instead prepared from 2,6-di-tert-butylphenol, where para-coupling is the only possibility.[4] A reaction with oxygen produces phenol-radicals which undergo rapid dimerisation, ultimately forming a diphenoquinone.
This intermediate is reduced to the tetra-butyl-biphenyl derivative by a reaction with two equivalents of 2,6-di-tert-butylphenol, in an oxygen-free environment (with the radicals generated dimerising to form additional tetra-butyl-biphenyl).[3] In the final step, high temperature dealkylation is performed to remove the butyl groups, producing the desired 4,4′-biphenol product.[4] If groups less bulky that t-butyl are used then polyphenylene ethers such as poly(p-phenylene oxide) can be produced.[7]
Safety
[edit]4,4'-Biphenol exhibits estrogenic SAR.[8]
See also
[edit]References
[edit]- ↑ Chen, Guoliang; Du, Fangyu; Zhou, Qifan; Liu, Dongdong; Fang, Ting; Shi, Yajie; Du, Yang (2018-01-31). "Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis (Supporting Information)". Synlett. 29 (6): 779–784. doi:10.1055/s-0036-1591892. ISSN 0936-5214. S2CID 104289422.
- ↑ Parker, David; Bussink, Jan; Van De Grampel, Hendrik T.; Wheatley, Gary W.; Dorf, Ernst-Ulrich; Ostlinning, Edgar; Reinking, Klaus; Schubert, Frank; Jünger, Oliver; Wagener, Reinhard (2012). "Polymers, High-Temperature". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a21_449.pub4. ISBN 978-3-527-30673-2.
- 1 2 Hay, A.S. (January 1965). "Dehydrogenation reactions with diphenoquinones". Tetrahedron Letters. 6 (47): 4241–4243. doi:10.1016/S0040-4039(01)89114-0.
- 1 2 3 Hay, Allan S. (April 1969). "p,p'-Biphenols". The Journal of Organic Chemistry. 34 (4): 1160–1161. doi:10.1021/jo01256a098.
- ↑ Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; et al. (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 3527306730.
- ↑ O’Brien, M. K.; Vanasse, B. (2004). "Vanadium(IV) Chloride". In Paquette, L. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York, NY: J. Wiley & Sons. doi:10.1002/047084289X.rv001. ISBN 0471936235.
- ↑ Hay, Allan S. (April 1962). "Polymerization by oxidative coupling. II. Oxidation of 2,6-disubstituted phenols". Journal of Polymer Science. 58 (166): 581–591. Bibcode:1962JPoSc..58..581H. doi:10.1002/pol.1962.1205816634.
- ↑ Kuiper, George G. J. M.; Lemmen, Josephine G.; Carlsson, Bo; Corton, J. Christopher; Safe, Stephen H.; Van Der Saag, Paul T.; Van Der Burg, Bart; Gustafsson, Jan-Åke (1998). "Interaction of Estrogenic Chemicals and Phytoestrogens with Estrogen Receptor β". Endocrinology. 139 (10): 4252–4263. doi:10.1210/endo.139.10.6216. PMID 9751507.