Hexachlorobuta-1,3-diene

Structural formula
General
Surname	Hexachlorobuta-1,3-diene
other names	Hexachloro-1,3-butadiene Perchlorobutadiene Hexachlorobutate Triping HCBD
Molecular formula	C 4 Cl 6
Brief description	colorless liquid with a turpentine odor
External identifiers / databases
CAS number 87-68-3 EC number 201-765-5 ECHA InfoCard 100.001.605 PubChem 6901 Wikidata Q416393
properties
Molar mass	260.76 g mol −1
Physical state	liquid
density	1.67 g cm −3
Melting point	−21 ° C
boiling point	215 ° C
Vapor pressure	29 Pa (25 ° C)
solubility	poor in water (0.5 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 301-310-315-318-351 P: 280-301 + 310-302 + 350-305 + 351 + 338-310
MAK	Switzerland: 0.02 ml m −3 or 0.24 mg m −3
Thermodynamic properties
ΔH f 0	−24.5 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexachlorbuta-1,3-diene is a chemical compound from the group of aliphatic unsaturated halogenated hydrocarbons and organic chlorine compounds .

properties

Hexachlorobutadiene is a toxic, bioaccumulating organic compound that is a colorless liquid with a mild odor. It is no longer manufactured in the EU and is not used in Germany. However, it can arise as a by-product or waste product in some chemical production and combustion processes (e.g. in the synthesis of organic halogen compounds such as tetrachloroethene , trichloroethene or carbon tetrachloride by chlorolysis ) and is detectable in the environment due to its relatively high vapor pressure. Classified as dangerous as a priority under the Water Framework Directive, as it can also be detected in groundwater (e.g. in the vicinity of industrial plants). According to the results of the European emissions inventory, the majority of the reported emissions come from the area of ​​organic basic chemistry.

use

Hexachlorbuta-1,3-diene was used as a hydraulic fluid , solvent for elastomers , heat-transferring fluid, coolant in transformers, fluid for gyroscopes, adsorbent for gas contamination, biocide to prevent algae formation (industrial water reservoirs and cooling water systems) and in some EU countries as a plant protection agent in viticulture used. It was also used as an intermediate in the manufacture of fluorine-containing lubricants and rubber compounds.

An exemplary example of the use of hexachlorobutadiene as a solvent is the FeCl ₃ -catalyzed chlorination of toluene for the production of pentachlorotoluene .

safety instructions

Hexachlorbuta-1,3-diene as is carcinogenic category 2 (substances that owing to possible carcinogenic effects in humans cause for concern) classified. During the pyrolysis of hexachlorbuta-1,3-diene, poisonous combustion products such as dioxins are formed . Hexachlorbuta-1,3-diene has been included in Appendices A and C to the Stockholm Convention .

proof

The detection takes place according to the liquid / liquid extraction process in the original sample by means of purge & trap enrichment and subsequent GC / MS analysis.

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on hexachlorbuta-1,3-diene in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
2. ↑ Schweizerische Unfallversicherungsanstalt (Suva): Limit values ​​- current MAK and BAT values (search for 87-68-3 or hexachlorbuta-1,3-diene ), accessed on November 2, 2015.
3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-25.
4. ↑ Cross-media environmental control in selected areas ( Memento of the original from September 1, 2006 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 608 kB) 
5. ↑ ^{a b c} Emission reduction for priority and priority hazardous substances of the Water Framework Directive - material data sheets - data sheet hexachlorobutadiene , texts 29/07, environmental research plan of the Federal Minister for the Environment, Nature Conservation and Nuclear Safety, p. 230ff.
6. ↑ Pravin Khandare and Ron Spohn, “Toluenes, Ring-Chlorinated,” Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons Inc, 2001, doi : 10.1002 / 0471238961.18091407120914.a01.pub2 .
7. ↑ Michael T. Holbrook, “Carbon Tetrachloride,” Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons Inc, 1993, doi : 10.1002 / 0471238961.0301180208151202.a01 .
8. ↑ SC-8/12: Listing of hexachlorobutadiene , p. 66, Stockholm Convention , May 2017.