1,1,1,3,3,3-Hexachloropropane

There are 29 chlorinated derivatives of propane (four of them being hexachloropropanes, with the formula {{Chem2|C3Cl6H2}}). This was the last one of them to be synthesized—by A. W. Davis and A. M. Whaley—in 1950.

1,1,1,3,3,3-Hexachloropropane is a liquid that boils at 206 °C. Its boiling point is significantly higher than expected based on estimations from various molecular parameters.

The original synthesis by Davis and Whaley obtained the compound by reacting 1,1,3,3-tetrachloropropane and/or 1,1,1,3-tetrachloropropane with chlorine at 80-100 °C, through 1,1,1,3,3-pentachloropropane as an intermediate step.

The compound can be produced quantitatively also by reacting carbon tetrachloride {{Chem2|CCl4}} and 1,1-dichloroethene {{Chem2|Cl2C\dCH2}} at 80-150 °C, with a copper-based catalyst, such as copper(I) chloride or copper(II) chloride, and possibly an amine as co-catalyst. The same process can generate higher chlorinated alkanes of the form {{Chem2|H3C\s(CH2\sCCl2)_{n}Cl}}.

The compound has been considered as an intermediate in the manufacture of 1,1,1,3,3,3-hexafluoropropane, through reaction with hydrogen fluoride.

A 2001 study found that the compound had significant effects on rat fetuses when inhaled at 25 ppm. The LD{{Sub|50}} (injection, rats) was found to be 827 mg/kg.

• 1,1,2,2,3,3-Hexachloropropane
• 1,1,1,3,3,3-Hexafluoropropane
• Octachloropropane
• 1,1,1,3,3,3-Hexachloro-2,2-difluoropropane

H. W. Davis and A. M. Whaley (1950): "Preparation of 1,1,1,3,3,3-hexachloropropane". Journal of the American Chemical Society, volume 73, issue 5, page 2361. {{doi|10.1021/ja01149a514}}

US National Institutes of Health (2020): "[https://pubchem.ncbi.nlm.nih.gov/compound/19215 1,1,1,3,3,3-Hexachloropropane]". Compound page at the PubChem online database, NCBI. Accessed on 2020-07-14.

United States Environmental Protection Agency (2020): "[https://comptox.epa.gov/dashboard/DTXSID3074600 Propane, 1,1,1,3,3,3-hexachloro-]". Compound page at the DSSTox online database. Accessed on 2020-07-14.

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Mohamed Belbachir, Bernard Boutevin, Yves Piétrasanta, and Gérard Rigal (1984): "Télomérisation du chlorure de vinylidène, 2. Réaction avec des télogènes du type R-CCL3 et préparation de composés dérivés". Makromolekulare Chemie (Macromolecular Chemistry and Physics), volume 185, issue 8, pages 1597-1606. {{doi|10.1002/macp.1984.021850809}}

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Richard Leroy Wilson, Charles Richard Cupit, and Rodney Lee Klausmeyer (1996): "[https://patentimages.storage.googleapis.com/c8/7a/de/b3d01e9282f3c0/US5792893.pdf Method for the manufacture of 1,1,1,3,3,3-hexachloropropane]". US Patent 5792893. Granted on 1998-08-11, Assigned to Vulcan Materials, then Basic Chemicals, then Occidental Chemical; expired on 2016-07-09.

韩箴贤 Hán Xhēnxián, 徐卫国 Xú Wèiguó, 尤来方 Yóu Láifāng, 吴江平 Wú Jiāngpíng (1998): "[https://patentimages.storage.googleapis.com/c1/83/b8/eb609c7c39aca2/CN1218788A.pdf 1,1,1,3,3,3-六氯丙烷制备方法]" ("1,1,1,3,3,3-hexachloropropane preparation method"). Chinese patent 1218788A. Granted on 1999-06-09.

蒋琦 Jiǎng Qí (2002): "[https://patentimages.storage.googleapis.com/d9/71/9d/9ab80dde3f7b95/CN1150145C.pdf 1,1,1,3,3,3-六氯丙烷的制备方法]" ("Preparation method of 1,1,1,3,3,3-hexachloropropane"). Chinese patent 1150145C. Granted on 2004-05-19.

J. R. Bamberger, G. S. Ladics, M. E. Hurtt, M. S. Swanson, and W. J. Brock (2001): "Subchronic inhalation toxicity of the chlorinated propane 1,1,1,3,3,3-hexachloropropane (HCC-230fa) in rats". Toxicological Sciences, volume 62, issue 1, pages 155-165. {{doi|10.1093/toxsci/62.1.155}}. {{PMID|11399803}}

W. J. Brock, S. M. Munley, M. S. Swanson, K. M. McGown, M. E. Hurtt (2003): "Developmental toxicity and genotoxicity studies of 1,1,1,3,3,3-hexachloropropane (HCC-230fa) in rats". Toxicological Sciences, volume 75, issue 2, pages 448–457. {{doi|10.1093/toxsci/kfg193}}

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Subhash C. Basak, Brian D. Gute, and Gregory D. Grunwald (1996): "A comparative study of topological and geometrical parameters in estimating normal boiling point and octanol/water partition coefficient". Journal of Chemical Information and Computer Science, volume 36, issue 6, pages 1054–1060. {{doi|10.1021/ci960024i}}

Pennetreau, Pascal (1992): "[https://data.epo.org/gpi/EP0522639A1 Process for the preparation of 1-chloro-1,1,3,3,3-pentafluoropropane and of 1,1,1,3,3,3-hexafluoropropane]". French patent EP 0522639 (A1). Granted on 1993-01-13; assigned to Solvay.

Kevin Robert Benson, David Elliott Bradley, and David Nalewajek (). "[https://patentimages.storage.googleapis.com/0c/73/82/26f23af63d628f/US5811604.pdf Continuous production of 1,1,1,3,3,3-hexafluoropropane and 1-chloro-1,1,3,3,3-pentafluoropropane]" US Patent 5811604. Granted on 1998-09-22; assigned to AlliedSignal, then Honeywell International. Expired on 2017-02-05.

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N. Mallikarjuna Rao (1994): "[https://patentimages.storage.googleapis.com/ea/b7/9a/a68bf001314e62/US5545774.pdf Process for the manufacture of 1,1,1,3,3,3-hexafluoropropane]". US Patent 5545774. Granted on 1996-08-13, assigned to DuPont; expired on 2014-12-08.

{{DEFAULTSORT:Hexachloropropane, 1, 1, 1, 3, 3, 3-}}

Category:Chloroalkanes