三硫丙酮

三硫丙酮
	IUPAC名; Hexamethyl-1,3,5-trithiane; 六甲基-1,3,5-三噻烷
別名	三硫代丙酮; 三聚硫代丙酮; trithioacetone
識別
CAS號	828-26-2
PubChem	13233
ChemSpider	12678
SMILES	C1(SC(SC(S1)(C)C)(C)C)(C)C;
Beilstein	5-19-09-00119
性質
化學式	C9H18S3
摩爾質量	222.43 g·mol−1
密度	1.0660－1.0700 g/mL
熔點	21.8℃
沸點	107℃（10 mmHg）
折光度n; D	1.5390－1.5430
危險性
	GHS危險性符號;
GHS提示詞	警告
H-術語	H315, H319, H335
P-術語	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

三硫丙酮（2,2,4,4,6,6-六甲基-1,3,5-三噻烷），也稱三聚硫代丙酮，是一種有機物，化學式為C
9H
18S
3，共價結構式為[–C(CH
3)
2–S–]
3。該化合物可以被看作是1,3,5-三硫雜環己烷的衍生物，即一個碳原子和硫原子交替出現的六元環，每個碳再連接兩個甲基，由甲基取代所有的氫原子^[3]^[1]。

該化合物是硫代丙酮（丙烷-2-硫酮）的穩定的環狀三聚物，而硫代丙酮本身是一個不穩定的化合物^[4]^[5]。相比之下，與之類似的化合物三丙酮（2,2,4,4,6,6-六甲基-1,3,5-三噁烷，氧原子代替硫原子）是不穩定的，而單體丙酮（2-丙酮）本身是穩定的。

製備

三硫丙酮最早由歐根·鮑曼（英語：Eugen Baumann）（Eugen Baumann）和E·弗羅姆（E. Fromm）於1889年通過硫化氫與丙酮的反應而合成^[5]。在25℃、酸性、有ZnCl
2催化劑的條件下，得到的產物是60%－70%的三硫丙酮，30%－40%的2,2-丙二硫醇，以及少量的兩種異構體雜質3,3,5,5,6,6-六甲基-1,2,4-三硫雜環己烷和4-巰基-2,2,4,6,6-五甲基-1,3-二硫雜環己烷^[5]。該產品也可以通過烯丙基異丙基硫醚（3-異丙硫基丙-1-烯）的熱解來獲得^[6]^[7]。

反應

三硫丙酮在500－650℃和5－20 mmHg下熱解產生硫丙酮，可通過−78℃的冷阱收集。

用途

三硫丙酮存在於一些香料中。其FEMA編號為3475。^[8]^[9]^[10]^[11]

毒性

小鼠口服LD₅₀為2.4 g/kg。^[8]^[2]

參見

2,4,6-三甲基-1,3,5-三噻烷
六甲基環三硅氧烷（英語：Hexamethylcyclotrisiloxane），硅氧雜環之相似物
六甲基環三硅氮烷，硅氮雜環之相似物^[12]
2,2,4,4,6,6-六甲基-1,3,5-三硒-2,4,6-三錫環己烷，錫-硒雜環之相似物^[13]^[14]

參考資料

^ ^1.0 ^1.1 ^1.2 ^1.3 TCI America (2020): "Product H1278: 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （頁面存檔備份，存於網際網路檔案館）". Online catalog page, accessed on 2020-01-01.
^ ^2.0 ^2.1 NCBI PubChem (2010): "2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （頁面存檔備份，存於網際網路檔案館）". Online chemical data sheet, accessed on 2020-01-01.
^ David S. Breslow, Herman Skolnik (2009): Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2; page 712. Volume 68 of Chemistry of Heterocyclic Compounds. ISBN 9780470188330
^ R. D. Lipscomb and W. H. Sharkey (1970): "Characterization and polymerization of thioacetone". Journal of Polymer Science - Part A: Polymer Chemistry, volume 8, issue 8, pages 2187–2196. doi:10.1002/pol.1970.150080826
^ ^5.0 ^5.1 ^5.2 William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". Polymerization, series Advances in Polymer Science, volume 17, pages 73-103. doi:10.1007/3-540-07111-3_2
^ William J. Bailey and Hilda Chu (1965): "Synthesis of polythioacetone". ACS Polymer Preprints, volume 6, pages=145–155
^ Horst Bohme, Hans Pfeifer, and Erich Schneider (1942): "Dimeric thioketones". Berichte der Deutschen Chemischen Gesellschaft, volume 75B, issue 7, pages 900–909. doi:10.1002/cber.19420750722 Note: This early report mistakes the trimer for the monomer.
^ ^8.0 ^8.1 E. J. Moran, O. D. Easterday, and B. L. Oser (1980): "Acute oral toxicity of selected flavor chemicals". Drug and Chemical Toxicology, volume 3,issue 3, pages 249-258.PMID 7449655 doi:10.3109/01480548009002221
^ World Health Organization (1999): "Trithioacetone^{[失效連結]}". Online data sheet in the Evaluation of the Joint FAO/WHO Expert Committee on Food Additives (JECFA). Accessedd on 2020-01-02.
^ G. Ohloff and I. Flament (1979): "The Role of Heteroatomic Substances in the Aroma Compounds of Foodstuffs". In Fortschritte der Chemie Organischer Naturstoffe (Progress in the Chemistry of Organic Natural Products), volume 36, pages 231-283. doi:10.1007/978-3-7091-3265-4_2
^ EUR-Lex (2012): "Table entry 15.009: Trithioacetone （頁面存檔備份，存於網際網路檔案館）". In EU Regulation No. 872/2012, Document 32012R0872, Official Journal of the EU - Series L, volume 267, pages 1–161.
^ Stuart D. Brewer and Charles P. Haber (1948): "Alkylsilazanes and Some Related Compounds". Journal of the American Chemical Society, volume 70, issue 11, pages 3888-3891. doi:10.1021/ja01191a106
^ B. M. Mikhova (2008), "NMR Data for Carbon-13 - C6H18Se3Sn3" in Landolt-Börnstein - Group III Condensed Matter, volume 35 Nuclear Magnetic Resonance Data, subvolume D5, Organometallic Compounds. doi:10.1007/978-3-540-74189-3_1362
^ Martin Dräger, Axel Blecher, Hans-Jürgen Jacobsen, Bernt Krebs (1978): "Molekül- und kristallstruktur von hexamethylcyclo-tristannaselenan [(CH
3)
2SnSe]
3". Journal of Organometallic Chemistry, volume 161, issue 3, pages 319-325. doi:10.1016/S0022-328X(00)92243-5

[tcicat-1] 1.0 ^1.1 ^1.2 ^1.3 TCI America (2020): "Product H1278: 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （頁面存檔備份，存於網際網路檔案館）". Online catalog page, accessed on 2020-01-01.

[pubchem-2] 2.0 ^2.1 NCBI PubChem (2010): "2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （頁面存檔備份，存於網際網路檔案館）". Online chemical data sheet, accessed on 2020-01-01.

[bres2009-3] David S. Breslow, Herman Skolnik (2009): Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2; page 712. Volume 68 of Chemistry of Heterocyclic Compounds. ISBN 9780470188330

[lips1970-4] R. D. Lipscomb and W. H. Sharkey (1970): "Characterization and polymerization of thioacetone". Journal of Polymer Science - Part A: Polymer Chemistry, volume 8, issue 8, pages 2187–2196. doi:10.1002/pol.1970.150080826

[shar1979-5] 5.0 ^5.1 ^5.2 William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". Polymerization, series Advances in Polymer Science, volume 17, pages 73-103. doi:10.1007/3-540-07111-3_2

[bail1965-6] William J. Bailey and Hilda Chu (1965): "Synthesis of polythioacetone". ACS Polymer Preprints, volume 6, pages=145–155

[bohme1942-7] Horst Bohme, Hans Pfeifer, and Erich Schneider (1942): "Dimeric thioketones". Berichte der Deutschen Chemischen Gesellschaft, volume 75B, issue 7, pages 900–909. doi:10.1002/cber.19420750722 Note: This early report mistakes the trimer for the monomer.

[mora1980-8] 8.0 ^8.1 E. J. Moran, O. D. Easterday, and B. L. Oser (1980): "Acute oral toxicity of selected flavor chemicals". Drug and Chemical Toxicology, volume 3,issue 3, pages 249-258.PMID 7449655 doi:10.3109/01480548009002221

[who-9] World Health Organization (1999): "Trithioacetone^{[失效連結]}". Online data sheet in the Evaluation of the Joint FAO/WHO Expert Committee on Food Additives (JECFA). Accessedd on 2020-01-02.

[ohlo1979-10] G. Ohloff and I. Flament (1979): "The Role of Heteroatomic Substances in the Aroma Compounds of Foodstuffs". In Fortschritte der Chemie Organischer Naturstoffe (Progress in the Chemistry of Organic Natural Products), volume 36, pages 231-283. doi:10.1007/978-3-7091-3265-4_2

[euro2012-11] EUR-Lex (2012): "Table entry 15.009: Trithioacetone （頁面存檔備份，存於網際網路檔案館）". In EU Regulation No. 872/2012, Document 32012R0872, Official Journal of the EU - Series L, volume 267, pages 1–161.

[brew1948-12] Stuart D. Brewer and Charles P. Haber (1948): "Alkylsilazanes and Some Related Compounds". Journal of the American Chemical Society, volume 70, issue 11, pages 3888-3891. doi:10.1021/ja01191a106

[mikh2008-13] B. M. Mikhova (2008), "NMR Data for Carbon-13 - C6H18Se3Sn3" in Landolt-Börnstein - Group III Condensed Matter, volume 35 Nuclear Magnetic Resonance Data, subvolume D5, Organometallic Compounds. doi:10.1007/978-3-540-74189-3_1362

[draeg1978-14] Martin Dräger, Axel Blecher, Hans-Jürgen Jacobsen, Bernt Krebs (1978): "Molekül- und kristallstruktur von hexamethylcyclo-tristannaselenan [(CH
3)
2SnSe]
3". Journal of Organometallic Chemistry, volume 161, issue 3, pages 319-325. doi:10.1016/S0022-328X(00)92243-5

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]