1,4-Butanedithiol Explained

1,4-Butanedithiol is an organosulfur compound with the formula . It is a malodorous, colorless liquid that is highly soluble in organic solvents. The compound has found applications in biodegradable polymers.[1]

Reactions

Alkylation with geminal dihalides gives 1,3-dithiepanes. Oxidation gives the cyclic disulfide 1,2-dithiane:[2]

It forms self-assembled monolayers on gold.[3]

It is also used in polyadditions along with 1,4-butanediol to form sulfur-containing polyester and polyurethanes containing diisocyanate.[4] [5] Several of these polymers are considered biodegradable and many of their components are sourced from non-petroleum oils.[6]

Related compounds

References

  1. Türünç . Oĝuz . Meier . Michael A. R. . 2011 . Thiol-ene vs. ADMET: a complementary approach to fatty acid-based biodegradable polymers . Green Chemistry . en . 13 . 2 . 314 . 10.1039/c0gc00773k . 1463-9262.
  2. 10.1021/jo200496r . Aerobic Oxidation of Thiols to Disulfides Catalyzed by Diaryl Tellurides under Photosensitized Conditions . 2011 . Oba . Makoto . Tanaka . Kazuhito . Nishiyama . Kozaburo . Ando . Wataru . The Journal of Organic Chemistry . 76 . 10 . 4173–4177 . 21480642 .
  3. 10.1021/ja4097384 . Structural Study of Citrate Layers on Gold Nanoparticles: Role of Intermolecular Interactions in Stabilizing Nanoparticles . 2014 . Park . Jong-Won . Shumaker-Parry . Jennifer S. . Journal of the American Chemical Society . 136 . 5 . 1907–1921 . 24422457 .
  4. Kojio . Ken . Nozaki . Shuhei . Takahara . Atsushi . Yamasaki . Satoshi . 2020 . Influence of chemical structure of hard segments on physical properties of polyurethane elastomers: a review . Journal of Polymer Research . en . 27 . 6 . 10.1007/s10965-020-02090-9 . 218528107 . 1022-9760.
  5. Sakhno . T. V. . Sakhno . Yu. E. . Kuchmiy . S. Ya. . 2023 . Clusteroluminescence of Unconjugated Polymers: A Review . Theoretical and Experimental Chemistry . en . 59 . 2 . 75–106 . 10.1007/s11237-023-09768-3 . 260597152 . 0040-5760.
  6. Kreye . Oliver . Tóth . Tommy . Meier . Michael A. R. . 2011-09-01 . Copolymers derived from rapeseed derivatives via ADMET and thiol-ene addition . European Polymer Journal . 47 . 9 . 1804–1816 . 10.1016/j.eurpolymj.2011.06.012 . 2011EurPJ..47.1804K . 0014-3057.

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