Hexachlorocyclopentadiene

Structural formula
General
Surname	Hexachlorocyclopentadiene
other names	1,2,3,4,5,5-hexachloro-cyclopenta-1,3-diene; Perchlorocyclopentadiene; HCCPD; Hex;
Molecular formula	C 5 Cl 6
Brief description	non-flammable, pale yellow liquid with a sharp odor
External identifiers / databases
EC number	201-029-3
ECHA InfoCard	100,000,937
PubChem	6478
Wikidata	Q408998
properties
Molar mass	272.77 g mol −1
Physical state	liquid
density	1.71 g cm −3 at 20 ° C
Melting point	11.34 ° C
boiling point	239 ° C
Vapor pressure	0.12 h Pa (25 ° C)
solubility	almost insoluble in water (0.8–2.1 mg l −1 at 20 ° C)
Refractive index	1.5658 (20 ° C)
safety instructions
H and P phrases	H: 302-311-330-314-410
	P: ?
MAK	Switzerland: 0.01 ml m −3 or 0.1 mg m −3
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Hexachlorocyclopentadiene ( HCCPD ) is a chemical compound from the group of chlorinated hydrocarbons, which is a lemon-yellow liquid that is toxic to humans. It was previously used to make several now-banned insecticides and was produced in large quantities until 1970, but is still an important intermediate.

properties

HCCPD has a pungent odor and a flash point of 109 ° C. It is difficult to dissolve in water with slow elimination of hydrogen chloride . It is miscible with acetone , carbon tetrachloride , methanol and hexane .

Hexachlorocyclopentadiene is highly reactive in addition, substitution and Diels-Alder reactions .

Extraction

Perchlorocyclopentadiene industrially by chlorination of cyclopentadiene prepared and then heating the partially chlorinated product in the presence of catalysts.

use

Hexachlorocyclopentadiene is the precursor for the synthesis of insecticides aldrin , chlordane , dieldrin , endrin , endosulfan , heptachlor , isodrin , Mirex and dienochlor (so-called. Chlorinated cyclodienes ), largely from the Stockholm Convention were banned.

The substance can also be used for the production of flame retardants , non-flammable resins , break-proof plastics, acids , esters , ketones , fluorocarbons and dyes .

Physiological data

According to the latest version (November 2004), hexachlorocyclopentadiene is not to be classified as mutagenic, carcinogenic or teratogenic; the occupational exposure limit is 0.02 ml · m ⁻³ or 0.2 mg · m ⁻³ .

Individual evidence

↑ ^a ^b Entry on Hexachlorocyclopentadiene in ChemicalBook , accessed April 18, 2012.
↑ ^a ^b ^c ^d ^e ^f Entry on hexachlorocyclopentadiene in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-276.
↑ Entry on hexachlorocyclopentadiene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 77-47-4 or hexachlorocyclopentadiene ), accessed on November 2, 2015.
↑ Åke Bergman , Andreas Rydén, Robin J. Law, Jacob de Boer, Adrian Covaci, Mehran Alaee, Linda Birnbaum, Myrto Petreas, Martin Rose, Shinichi Sakai, Nele Van den Eede, Ike van der Veen: A novel abbreviation standard for organobromine , organochlorine and organophosphorus flame retardants and some characteristics of the chemicals . In: Environment International . tape 49 , 2012, p. 57–82 , doi : 10.1016 / j.envint.2012.08.003 , PMC 3483428 (free full text).
↑ Agency for Toxic Substances and Disease Registry: Toxicological Profile for Hexachlorocyclopentadiene (HCCPD) (PDF; 4.6 MB), July 1999, accessed June 4, 2016.
↑ Patent US4255597 : Process for preparing hexachlorocyclopentadiene. Applied on April 18, 1980 , published March 10, 1981 , Applicant: Velsicol Chemical Corporation, Inventor: Kalidas Paul, Glendon D. Kyker. ‌
↑ Justification on hexachlorocyclopentadiene in TRGS 900 (pdf, 55 kB)
↑ TRGS 900, January 2006 (pdf, 2 MB)

[Chemical_Book-1] Entry on Hexachlorocyclopentadiene in ChemicalBook , accessed April 18, 2012.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f Entry on hexachlorocyclopentadiene in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CRC90_3_276-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-276.

[CLP_100.000.937-4] Entry on hexachlorocyclopentadiene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 77-47-4 or hexachlorocyclopentadiene ), accessed on November 2, 2015.

[6] Åke Bergman , Andreas Rydén, Robin J. Law, Jacob de Boer, Adrian Covaci, Mehran Alaee, Linda Birnbaum, Myrto Petreas, Martin Rose, Shinichi Sakai, Nele Van den Eede, Ike van der Veen: A novel abbreviation standard for organobromine , organochlorine and organophosphorus flame retardants and some characteristics of the chemicals . In: Environment International . tape 49 , 2012, p. 57–82 , doi : 10.1016 / j.envint.2012.08.003 , PMC 3483428 (free full text).

[7] Agency for Toxic Substances and Disease Registry: Toxicological Profile for Hexachlorocyclopentadiene (HCCPD) (PDF; 4.6 MB), July 1999, accessed June 4, 2016.

[8] Patent US4255597 : Process for preparing hexachlorocyclopentadiene. Applied on April 18, 1980 , published March 10, 1981 , Applicant: Velsicol Chemical Corporation, Inventor: Kalidas Paul, Glendon D. Kyker. ‌

[9] Justification on hexachlorocyclopentadiene in TRGS 900 (pdf, 55 kB)

[10] TRGS 900, January 2006 (pdf, 2 MB)