2,2,4,4-tetramethyl-1,3-cyclobutanediol
Structural formula | ||||||||||||||||
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cis form (left), trans form | ||||||||||||||||
General | ||||||||||||||||
Surname | 2,2,4,4-tetramethyl-1,3-cyclobutanediol | |||||||||||||||
other names |
CBDO |
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Molecular formula | C 8 H 16 O 2 | |||||||||||||||
Brief description |
white solid |
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properties | ||||||||||||||||
Molar mass | 144.21 g mol −1 | |||||||||||||||
Physical state |
firmly |
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Melting point |
126-129 ° C |
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boiling point |
210-215 ° C |
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safety instructions | ||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
2,2,4,4-Tetramethylcyclobutane-1,3-diol is a chemical compound from the group of diols . It occurs in two isomeric forms, the cis form and the trans form.
Extraction and presentation
2,2,4,4-tetramethylcyclobutane-1,3-diol can be obtained by pyrolysis of isobutyric anhydride followed by hydrogenation of the resulting 2,2,4,4,4-tetramethylcyclobutanedione.
The compound can also be prepared by hydrogenation of 1,3-dioxo-2,2,4,4-tetramethyl-cyclobutane .
properties
2,2,4,4-tetramethylcyclobutane-1,3-diol is a white solid. The C 4 ring of the cis isomer of the compound is not planar. For simple non-planar cyclobutanes, the opening angles are between 19 and 31 °. The cis isomer of 2,2,4,4-tetramethylcyclobutane-1,3-diol crystallizes out as two conformers with an average opening angle of 17.5 °. The trans However isomer has an opening angle of 0 °.
use
2,2,4,4-tetramethylcyclobutane-1,3-diol is used as an intermediate in the production of polymers , e.g. B. from Tritan . It can replace bisphenol A here .
Individual evidence
- ↑ a b c d e f Entry on 2,2,4,4-tetramethylcyclobutane-1,3-diol in the GESTIS substance database of the IFA , accessed on October 17, 2018(JavaScript required) .
- ↑ Data sheet 2,2,4,4-Tetramethyl-1,3-cyclobutanediol, mixture of isomers, 99% from Sigma-Aldrich , accessed on October 17, 2018 ( PDF ).
- ↑ E. Wedeking, W. Weisswange: About the synthesis of a diketone of the cyclobutane series. In: Reports of the German Chemical Society. 39, 1906, p. 1631, doi : 10.1002 / cber.19060390287 .
- ↑ Houben-Weyl Methods of Organic Chemistry Vol. VI / 1b, 4th Edition Alcohols III . Georg Thieme Verlag, 2014, ISBN 3-13-180044-5 , p. 40 ( limited preview in Google Book search).
- ↑ CD Shirrell, DE Williams: The crystal and molecular structure of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol. In: Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 32, 1976, p. 1867, doi : 10.1107 / S0567740876006559 .
- ↑ TN Margulis: Planar cyclobutanes: structure of 2,2,4,4-tetramethyl-cyclobutane-trans-1,3-diol. In: Journal of the Chemical Society D: Chemical Communications. 1969, p. 215, doi : 10.1039 / C29690000215 .
- ↑ Donald R. Kelsey, Betty M. Scardino, Janusz S. Grebowicz, Hoe H. Chuah: High Impact, Amorphous Terephthalate Copolyesters of Rigid 2,2,4,4-Tetramethyl-1,3-cyclobutanediol with Flexible Diols , Macromolecules, 2000, 33 (16), pp. 5810-5818, doi: 10.1021 / ma000223 + , July 20, 2000.
- ↑ Google Patents: US5955565A - Polyesters from terephthalic acid, 2,2,4,4-tetramethyl-1,3-cyclobutanediol and ethylene glycol - Google Patents , accessed October 17, 2018.
- ↑ Wolfgang Kaiser: Kunststoffchemie für Ingenieure From synthesis to application . Carl Hanser Verlag GmbH Co KG, 2015, ISBN 978-3-446-44774-5 , pp. 345 ( limited preview in Google Book search).