三硫丙酮

三硫丙酮
	IUPAC名; Hexamethyl-1,3,5-trithiane; 六甲基-1,3,5-三噻烷
别名	三硫代丙酮; 三聚硫代丙酮; trithioacetone
识别
CAS号	828-26-2
PubChem	13233
ChemSpider	12678
SMILES	C1(SC(SC(S1)(C)C)(C)C)(C)C;
Beilstein	5-19-09-00119
性质
化学式	C9H18S3
摩尔质量	222.43 g·mol−1
密度	1.0660－1.0700 g/mL[1]
熔点	21.8℃[2]
沸点	107℃（10 mmHg）[1]
折光度n; D	1.5390－1.5430[1]
危险性
	GHS危险性符号;
GHS提示词	警告
H-术语	H315, H319, H335
P-术语	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

三硫丙酮（2,2,4,4,6,6-六甲基-1,3,5-三噻烷），也称三聚硫代丙酮，是一种有机物，化学式为C
9H
18S
3，共价结构式为[–C(CH
3)
2–S–]
3。该化合物可以被看作是1,3,5-三硫雜環己烷的衍生物，即一个碳原子和硫原子交替出现的六元环，每个碳再连接两个甲基，由甲基取代所有的氢原子[3][1]。

该化合物是硫代丙酮（丙烷-2-硫酮）的稳定的环状三聚物，而硫代丙酮本身是一个不稳定的化合物[4][5]。相比之下，与之类似的化合物三丙酮（2,2,4,4,6,6-六甲基-1,3,5-三噁烷，氧原子代替硫原子）是不稳定的，而单体丙酮（2-丙酮）本身是稳定的。

制备

三硫丙酮最早由欧根·鲍曼（Eugen Baumann）和E·弗罗姆（E. Fromm）于1889年通过硫化氢与丙酮的反应而合成[5]。在25℃、酸性、有ZnCl
2催化剂的条件下，得到的产物是60%－70%的三硫丙酮，30%－40%的2,2-丙二硫醇，以及少量的两种异构体杂质3,3,5,5,6,6-六甲基-1,2,4-三硫雜環己烷和4-巯基-2,2,4,6,6-五甲基-1,3-二硫雜環己烷[5]。该产品也可以通过烯丙基异丙基硫醚（3-异丙硫基丙-1-烯）的热解来获得[6][7]。

反应

三硫丙酮在500－650℃和5－20 mmHg下热解产生硫丙酮，可通过−78℃的冷阱收集。

三硫丙酮（左）和硫丙酮（右）通过热分解/聚合可互相转化

用途

三硫丙酮存在于一些香料中。其FEMA编号为3475。[8][9][10][11]

毒性

小鼠口服LD₅₀为2.4 g/kg。[8][2]

参见

2,4,6-三甲基-1,3,5-三噻烷
六甲基环三硅氧烷，硅氧杂环之相似物
六甲基环三硅氮烷，硅氮杂环之相似物[12]
2,2,4,4,6,6-六甲基-1,3,5-三硒-2,4,6-三锡环己烷，锡-硒杂环之相似物[13][14]

参考资料

TCI America (2020): "Product H1278: 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （页面存档备份，存于）". Online catalog page, accessed on 2020-01-01.
NCBI PubChem (2010): "2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （页面存档备份，存于）". 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
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.
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". 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 （页面存档备份，存于）". 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

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[tcicat-1] TCI America (2020): "Product H1278: 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （页面存档备份，存于）". Online catalog page, accessed on 2020-01-01.

[pubchem-2] NCBI PubChem (2010): "2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （页面存档备份，存于）". 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] 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] 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". 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 （页面存档备份，存于）". 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