2,2,4,4-tetramethyl-1,3-cyclobutanediol

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Structural formula
Structural formula of 2,2,4,4-tetramethylcyclobutane-1,3-diol
cis form (left), trans form
General
Surname 2,2,4,4-tetramethyl-1,3-cyclobutanediol
other names

CBDO

Molecular formula C 8 H 16 O 2
Brief description

white solid

External identifiers / databases
CAS number
  • 3010-96-6
  • 3039-96-1 ( cis isomer)
  • 2694-23-7 ( trans isomer)
EC number 221-140-0
ECHA InfoCard 100.019.219
PubChem 76382
Wikidata Q3214022
properties
Molar mass 144.21 g mol −1
Physical state

firmly

Melting point

126-129 ° C

boiling point

210-215 ° C

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 07 - Warning

danger

H and P phrases H: 228-315-319-335
P: 210-261-305 + 351 + 338
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.

Synthesis of 2,2,4,4-tetramethylcyclobutane-1,3-diol

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

  1. ↑ 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) .
  2. ↑ Data sheet 2,2,4,4-Tetramethyl-1,3-cyclobutanediol, mixture of isomers, 99% from Sigma-Aldrich , accessed on October 17, 2018 ( PDF ).
  3. ↑ 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 .
  4. ↑ 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).
  5. ↑ 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 .
  6. ↑ 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 .
  7. ↑ 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.
  8. ↑ Google Patents: US5955565A - Polyesters from terephthalic acid, 2,2,4,4-tetramethyl-1,3-cyclobutanediol and ethylene glycol - Google Patents , accessed October 17, 2018.
  9. ↑ 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).