二氧化硫脲

二氧化硫脲
	IUPAC名; Amino(imino)methanesulfinic acid
別名	甲脒亞磺酸; 氨基亞氨基甲亞磺酸
識別
CAS號	1758-73-2
PubChem	61274
ChemSpider	55213
SMILES	C(=N)(N)S(=O)O;
性質
化學式	CH4N2O2S
摩爾質量	108.12 g·mol−1
外觀	白色粉末
熔點	126 °C（399 K）
溶解性（水）	3.0 g/100 mL
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二氧化硫脲是一種有機硫化合物，可用於布料工業。^[1]它是一種還原劑，^[2]它是白色固體，有互變異構體。

結構

二氧化硫脲的結構依周圍環境而定。晶體和氣態的二氧化硫脲有C_2v對稱性。這個分子的鍵長（單位：皮米）為S-C = 186、C-N = 130 和S-O = 149。硫中心是三角錐形的。C-S鍵的鍵長更像一個單鍵。作為比較，硫脲的C=S雙鍵為171 pm。^[3]^[4]在水中或二甲基亞碸里，二氧化硫脲會轉化成另一種互變異構體，為一種亞磺酸，結構式(H₂N)HN=CS(O)(OH)。^[5]

製備

二氧化硫脲於1910年由英國化學家Edward de Barry Barnett首次合成。^[6]

二氧化硫脲是由過氧化氫氧化硫脲而成。^[7]

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

這個反應的機制已被研究。^[8]

它也可以由二氧化氯氧化硫脲而成。^[9]二氧化硫脲產品的質量可以通過用靛藍滴定評估。^[7]

用處

二氧化硫脲可用來漂白布料。^[10]它也可以把硝化芳香醛和硝化芳香酮還原成硝化芳香醇。^[11]

參考資料

^ Fischer, Klaus; Marquardt, Kurt; Schlüter, Kaspar; Gebert, Karlheinz; Borschel, Eva-Marie; Heimann, Sigismund; Kromm, Erich; Giesen, Volker; Schneider, Reinhard; Lee Wayland, Rosser, Textile Auxiliaries, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2000-06-15, doi:10.1002/14356007.a26_227
^ Dictionary. Gardner's Commercially Important Chemicals. Hoboken, NJ, USA: John Wiley & Sons, Inc. 2005-08-23. doi:10.1002/0471736627.ch1.
^ Sullivan, R. A. L.; Hargreaves, A. The Crystal and Molecular Structure of Thiourea Dioxide. Acta Crystallographica. 1962, 15 (7): 675–682. doi:10.1107/S0365110X62001851.
^ Chen, I-C.; Wang, Y. Reinvestigation of the Structure of Thiourea S,S‐Dioxide, CH₄N₂O₂S. Acta Crystallographica. 1984, 40: 1937–1938. doi:10.1107/S010827018401012X.
^ Makarov, S. V. Recent Trends in the Chemistry of Sulfur-Containing Reducing Agents. Russian Chemical Reviews. 2001, 70: 885–895. doi:10.1070/RC2001v070n10ABEH000659.
^ Barnett first prepared thiourea dioxide ("aminoiminomethanesulphinic acid") by oxidizing thiourea ("thiocarbamide") with hydrogen peroxide ("hydrogen dioxide"). See: Barnett, Edward de Barry (1910) "The action of hydrogen dioxide on thiocarbamides," （頁面存檔備份，存於網際網路檔案館） Journal of the Chemical Society, Transactions, 97 : 63–65.
^ ^7.0 ^7.1 Schubart, Rüdiger, Sulfinic Acids and Derivatives, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2000-06-15, doi:10.1002/14356007.a25_461
^ Hoffmann, Michael; Edwards, John O. Kinetics and Mechanism of the Oxidation of Thiourea and N,N'-dialkylthioureas by Hydrogen Peroxide. Inorganic Chemistry. 1977, 16: 3333–3338. doi:10.1021/ic50178a069.
^ Rábai, Gyula; Wang, Robert T.; Kustin, Kenneth. Kinetics and mechanism of the oxidation of thiourea by chlorine dioxide. International Journal of Chemical Kinetics (Wiley). 1993, 25 (1): 53–62. ISSN 0538-8066. doi:10.1002/kin.550250106.
^ Hebeish, A.; El-Rafie, M. H.; Waly, A.; 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. 1978, 22 (7): 1853–1866. doi:10.1002/app.1978.070220709.
^ Sambher, Shikha; Baskar, Chinnappan; Dhillon, Ranjit S. Chemoselective reduction of carbonyl groups of aromatic nitro carbonyl compounds to the corresponding nitroalcohols using thiourea dioxide. Arkivoc. 22 May 2009, 2009 (10): 141–145. doi:10.3998/ark.5550190.0010.a14 .

[1] Fischer, Klaus; Marquardt, Kurt; Schlüter, Kaspar; Gebert, Karlheinz; Borschel, Eva-Marie; Heimann, Sigismund; Kromm, Erich; Giesen, Volker; Schneider, Reinhard; Lee Wayland, Rosser, Textile Auxiliaries, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2000-06-15, doi:10.1002/14356007.a26_227

[2] Dictionary. Gardner's Commercially Important Chemicals. Hoboken, NJ, USA: John Wiley & Sons, Inc. 2005-08-23. doi:10.1002/0471736627.ch1.

[structure-3] Sullivan, R. A. L.; Hargreaves, A. The Crystal and Molecular Structure of Thiourea Dioxide. Acta Crystallographica. 1962, 15 (7): 675–682. doi:10.1107/S0365110X62001851.

[4] Chen, I-C.; Wang, Y. Reinvestigation of the Structure of Thiourea S,S‐Dioxide, CH₄N₂O₂S. Acta Crystallographica. 1984, 40: 1937–1938. doi:10.1107/S010827018401012X.

[Makarov-5] Makarov, S. V. Recent Trends in the Chemistry of Sulfur-Containing Reducing Agents. Russian Chemical Reviews. 2001, 70: 885–895. doi:10.1070/RC2001v070n10ABEH000659.

[6] Barnett first prepared thiourea dioxide ("aminoiminomethanesulphinic acid") by oxidizing thiourea ("thiocarbamide") with hydrogen peroxide ("hydrogen dioxide"). See: Barnett, Edward de Barry (1910) "The action of hydrogen dioxide on thiocarbamides," （頁面存檔備份，存於網際網路檔案館） Journal of the Chemical Society, Transactions, 97 : 63–65.

[Ull-7] 7.0 ^7.1 Schubart, Rüdiger, Sulfinic Acids and Derivatives, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2000-06-15, doi:10.1002/14356007.a25_461

[8] Hoffmann, Michael; Edwards, John O. Kinetics and Mechanism of the Oxidation of Thiourea and N,N'-dialkylthioureas by Hydrogen Peroxide. Inorganic Chemistry. 1977, 16: 3333–3338. doi:10.1021/ic50178a069.

[Kinetics-9] Rábai, Gyula; Wang, Robert T.; Kustin, Kenneth. Kinetics and mechanism of the oxidation of thiourea by chlorine dioxide. International Journal of Chemical Kinetics (Wiley). 1993, 25 (1): 53–62. ISSN 0538-8066. doi:10.1002/kin.550250106.

[10] Hebeish, A.; El-Rafie, M. H.; Waly, A.; 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. 1978, 22 (7): 1853–1866. doi:10.1002/app.1978.070220709.

[11] Sambher, Shikha; Baskar, Chinnappan; Dhillon, Ranjit S. Chemoselective reduction of carbonyl groups of aromatic nitro carbonyl compounds to the corresponding nitroalcohols using thiourea dioxide. Arkivoc. 22 May 2009, 2009 (10): 141–145. doi:10.3998/ark.5550190.0010.a14 .

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