Abstract:
:1,2-Dibromo-4-(1,2-dibromoethyl)cyclohexane (TBECH) is used primarily as an additive flame retardant. 1H NMR spectroscopy and an X-ray structure determination have revealed that a technical mixture consists largely of two (of the four possible) diastereomers, rac-(1R,2R)-1,2-dibromo-(4S)-4-((1S)-1,2-dibromoethyl)cyclohexane (alpha-TBECH) and rac-(1R,2R)-1,2-dibromo-(4S)-4-((1R)-1,2-dibromoethyl)cyclohexane (beta-TBECH), in a mole ratio of approximately 1:1. The two other possible isomers, gamma- and delta-TBECH, were not detected in a technical mixture. The TBECH isomers are thermally sensitive and can easily interconvert at temperatures of 125 degrees C. A thermal equilibrium mixture of alpha-, beta-, gamma- and delta-TBECH consists of approximately 33%, 33%, 17% and 17% of these isomers, respectively. Separation of all four TBECH diastereomers, with minimal thermal interconversion of the isomers, was achieved by careful selection of GC-capillary column length and injector temperature. Although technical TBECH does not contain the gamma- and delta-isomers, they may still be relevant environmental contaminants since manufacturing processes utilize thermal processes which may induce their formation.
journal_name
Chemospherejournal_title
Chemosphereauthors
Arsenault G,Lough A,Marvin C,McAlees A,McCrindle R,MacInnis G,Pleskach K,Potter D,Riddell N,Sverko E,Tittlemier S,Tomy Gdoi
10.1016/j.chemosphere.2008.03.044subject
Has Abstractpub_date
2008-07-01 00:00:00pages
1163-70issue
8eissn
0045-6535issn
1879-1298pii
S0045-6535(08)00387-1journal_volume
72pub_type
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