Diòxid de tiourea

Infotaula de compost químicDiòxid de tiourea
Substància químicatipus d'entitat química Modifica el valor a Wikidata
Massa molecular107,999 Da Modifica el valor a Wikidata
Estructura química
Fórmula químicaCH₄N₂O₂S Modifica el valor a Wikidata
SMILES canònic
Model 2D
C(=N)(N)S(=O)O Modifica el valor a Wikidata
Identificador InChIModel 3D Modifica el valor a Wikidata

Diòxid de tiourea (en anglès:Thiourea dioxide o thiox) és un compost d'organosofre que s'utilitza en la indústria tèxtil.[1] Funciona com agent reductor.[2] El diòxid de tiourea no és un diòxid, sinó un derivat de l'acid sulfínic (RS(O)(OH), per tant té el nom alternatiu de formamidina de l'àcid sulfínic.[3]

Síntesi

El diòxid de tiourea va ser preparat primer l'any 1910 pel químic Edward de Barry Barnett (1886–1961).[4]

El diòxid de tiourea es prepara per l'oxidació de tiourea amb peròxid d'hidrogen.[5]

(NH₂)₂CS + 2H₂O₂ → (NH)(NH₂)CSO₂H + 2H₂O

Usos

El diòxid de tiourea es fa servir com lleixiu blanquejant reductor en els tèxtils.[6] El diòxid de tiourea també s'ha usat per la reducció de nitroaldehids i nitrocetones aromàtiques a nitroalcohols.[7]

Referències

  1. ↑ Klaus Fischer et al. "Textile Auxiliaries" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a26_227
  2. ↑ Milne, G. W. A. Dictionary, in Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties, John Wiley & Sons, Inc. 2005, Hoboken, NJ, USA. doi:10.1002/0471736627.ch1
  3. ↑ «The Crystal and Molecular Structure of Thiourea Dioxide». Acta Crystallographica, 15, 7, 1962, pàg. 675–682. DOI: 10.1107/S0365110X62001851.
  4. ↑ Barnett first prepared thiourea dioxide ("aminoiminomethanesulphinic acid") by oxidizing thiourea ("thiocarbamide") with hydrogen peroxide ("hydrogen dioxide"). Vegeu: Barnett, Edward de Barry (1910) "The action of hydrogen dioxide on thiocarbamides," Journal of the Chemical Society, Transactions, 97 : 63–65.
  5. ↑ D. Schubart "Sulfinic Acids and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.a25_461
  6. ↑ Hebeish, A., El-Rafie, M. H., Waly, A. and Moursi, A. Z. «Graft copolymerization of vinyl monomers onto modified cotton. IX. Hydrogen peroxide–thiourea dioxide redox system induced grafting of 2-methyl-5-vinylpyridine onto oxidized celluloses». Journal of Applied Polymer Science, 22, 7, 1978, pàg. 1853–1866. DOI: 10.1002/app.1978.070220709.
  7. ↑ Sambher, S., Baskar, C., & Dhillon, R. S. «Chemoselective reduction of carbonyl groups of aromatic nitro carbonyl compounds to the corresponding nitroalcohols using thiourea dioxide». Arkivoc, 10, 2009, pàg. 141–145. ISSN: 1551-7012.

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