Abstract：
:Scission of sulfide linkages in vulcanized rubber has been a major concern since the early 20th century, because devulcanization is a key process for recycling waste rubber products as polymer materials that pose low environmental risks. We herein demonstrate that lipid peroxidation (LPO) of linoleic acid by manganese peroxidase (MnP), a proposed lignin-degradation system in the early stage of selective white rot fungi, cleaves sulfide bond in a model rubber compound, di(2-methylpent-2-enyl) sulfide, to 2,4-dimethylthiophene and 2-methyl-2-pentenal. The major intermediate of the LPO process, 2,4-decadienal was directly oxidized by MnP to cleave the sulfur-carbon bond. We propose that electrophilic radicals from 2,4-decadienal abstract one electron from a sulfur atom of the model compound to produce the sulfur radical cation intermediate, which in turn reacts with molecular oxygen to cleave the sulfur-carbon bond. The discovery of free radical-mediated scission of sulfide bond coupled with Mn oxidation provides a novel strategy for recycling vulcanized rubber wastes.
journal_name
Chemospherejournal_title
Chemosphereauthors
Sato S,Ohashi Y,Kojima M,Watanabe T,Honda Y,Watanabe Tdoi
10.1016/j.chemosphere.2009.08.014subject
Has Abstractpub_date
2009-10-01 00:00:00pages
798-804issue
6eissn
0045-6535issn
1879-1298pii
S0045-6535(09)00941-2journal_volume
77pub_type
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