1,3-dichloropropene

Structural formula
	;
	bottom: cis isomer, top: trans isomer
General
Surname	1,3-dichloropropene
other names	Chlorallyl chloride; 1,3-dichloro-1-propene; 1,3-DCP;
Molecular formula	C 3 H 4 Cl 2
Brief description	volatile, flammable, colorless to yellowish liquid with a pungent, sweetish, chloroform-like odor
External identifiers / databases
EC number	208-826-5
ECHA InfoCard	100.008.024
PubChem	24883
Wikidata	Q61854433
properties
Molar mass	110.97 g mol −1
Physical state	liquid
density	1.23 g cm −3 ; 1.22 g cm −3 (cis);
Melting point	−84 ° C
boiling point	108 ° C; 104 ° C ( cis );
Vapor pressure	37 h Pa (20 ° C); 53–69 hPa (20 ° C) ( cis );
solubility	poor in water (1 g l −1 at 20 ° C)
Refractive index	1.4682 ( cis , 20 ° C); 1.4730 ( trans , 20 ° C);
safety instructions
H and P phrases	H: 226-301-304-311-315-317-319-332-335-410
	P: 261-273-280-301 + 310-305 + 351 + 338-312
MAK	Switzerland: 0.11 ml m −3 or 0.5 mg m −3
Toxicological data	470 mg kg −1 ( LD 50 , rat , oral ) ; 640 mg kg −1 ( LD 50 , mouse , oral ) ;
	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

1,3-dichloropropene is a chemical compound from the group of unsaturated chlorinated hydrocarbons and alkenes .

Isomerism

The double bond of 1,3-dichloropropene can have an ( E ) or ( Z ) configuration. Without special production methods or purification technicians, 1,3-dichloropropene is usually in the form of an equilibrium mixture of the isomeric cis- and trans - 1,3-dichloropropene .

Isomers of 1,3-dichloropropene
Surname	( E ) -1,3-dichloropropene	( Z ) -1,3-dichloropropene
other names	trans -1,3-dichloropropene	cis -1,3-dichloropropene
Structural formula
CAS number	10061-02-6	10061-01-5
	542-75-6 (mixture of isomers)
EC number	626-466-0	233-195-8
	208-826-5 (mixture of isomers)
ECHA info card	100.154.864	100.030.165
	100.008.024 (mixture of isomers)
PubChem	24726	5280970
	24883 (mixture of isomers)
Wikidata	Q161507	Q27109091
	Q61854433 (mixture of isomers)

history

1,3-dichloropropene was introduced in 1945 as an artificial soil fumigant. From 1956 it was used extensively due to restrictions on the use of ethylene dibromide , dibromochloropropene and methyl bromide .

Extraction and presentation

1,3-Dichloropropene is a by-product of the production of allyl chloride by chlorination of propene at high temperatures. Alternatively, it can be obtained from 1,3-dichloropropanol by dehydration with POCl ₃ or with P ₄ O ₁₀ in benzene . The technical product often contains 1,2-dichloropropane and 2,3-dichloropropene as impurities.

use

1,3-Dichloropropene was mainly used as a pesticide and nematicide in agriculture as a soil fumigant and as a disinfectant (e.g. in container fumigation ), with cis -1,3-dichloropropene being more effective. In Germany, dichloropropene was frequently detected in groundwater, although its use has been completely prohibited in Germany since 2003 ( Federal Law Gazette I p. 1533 ), but is still common in Africa and the USA (e.g. for tobacco, carrots, potatoes and strawberries) .

safety instructions

The vapors of 1,3-dichloropropene can form an explosive mixture with air ( flash point 27 ° C). The compound decomposes at high temperatures, producing hydrogen chloride . It is still classified as carcinogenic category 2 and mutagenic category 3. 1,3-dichloropropene has a strong irritant effect on the skin, eyes and respiratory tract and has a narcotic effect.

proof

1,3-dichloropropene can be detected by gas chromatography after desorption .

Web links

Patent.de: Patent rotary flow reactor for the production of allyl chloride and dichloropropene
Patent DE2540336 : Process for the separation of 1,3-dichloropropene from allyl chloride distillation bottom products. Published September 10, 1975 , Applicant: Dow Chemical Co, Inventor: John Bruce Ivy, Gordon Grady Willis, Jackson Lake, David Charles Kelsoe. ‌

Individual evidence

↑ ^a ^b ^c ^d Entry on cis-1,3-dichloropropene in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 1,3-dichloropropene, mixture of isomers in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ ^a ^b 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. 3-160.
↑ Entry on 1,3-dichloropropene 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 542-75-6 or 1,3-dichloropropene (cis and trans) ), accessed on October 5, 2019.
↑ ^a ^b ^c ^d Poisons Information Monograph (PIM) for dichloropropenes, 1,3- , accessed December 9, 2014.
↑ Frequently detected pesticide active ingredients and metabolites (1996–2000) ( Memento of April 18, 2007 in the Internet Archive )
↑ Transparent plant protection (PDF; 305 kB)
↑ Main association of commercial trade associations: Procedure for the determination of cis- and trans-1,3-dichloropropene - no longer available, not even via web archive.

[GESTIS_CIS-1] Entry on cis-1,3-dichloropropene in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 1,3-dichloropropene, mixture of isomers in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[CRC90_3_160-3] 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. 3-160.

[CLP_100.008.024-4] Entry on 1,3-dichloropropene 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 542-75-6 or 1,3-dichloropropene (cis and trans) ), accessed on October 5, 2019.

[inchem-6] Poisons Information Monograph (PIM) for dichloropropenes, 1,3- , accessed December 9, 2014.

[7] Frequently detected pesticide active ingredients and metabolites (1996–2000) ( Memento of April 18, 2007 in the Internet Archive )

[8] Transparent plant protection (PDF; 305 kB)

[9] Main association of commercial trade associations: Procedure for the determination of cis- and trans-1,3-dichloropropene - no longer available, not even via web archive.