Allyl chloride

Structural formula
General
Surname	Allyl chloride
other names	3 − chloropropene; 3-chloroprop-1-en;
Molecular formula	C 3 H 5 Cl
Brief description	Highly flammable, colorless to red liquid with a mustard oil odor
External identifiers / databases
EC number	203-457-6
ECHA InfoCard	100.003.144
PubChem	7850
Wikidata	Q420473
properties
Molar mass	76.53 g mol −1
Physical state	liquid
density	0.94 g cm −3
Melting point	−136 ° C
boiling point	46-48 ° C
Vapor pressure	398 h Pa (20 ° C)
solubility	poor in water (4 g l −1 at 25 ° C)
Refractive index	1.4157 (20 ° C)
safety instructions
H and P phrases	H: 225-301-311-331-315-319-335-372-341-351-400
	P: 210-261-273-280-301 + 310-305 + 351 + 338
MAK	repealed as probably carcinogenic ; Switzerland: 1 ml m −3 or 3 mg m −3 ;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

Allyl chloride (3-chloropropene) is a toxic, environmentally harmful and highly flammable liquid that evaporates at room temperature . The gaseous substance is heavier than air and has a pungent, mustard oil- like odor . Allyl chloride is especially dangerous for fish and has the formula CH ₂ = CH – CH ₂ Cl.

Extraction and presentation

Allyl chloride is made by reacting propene with chlorine . Since the addition of chlorine to the double bond to form 1,2-dichloropropane is preferred at low temperatures, the process is carried out industrially at high temperatures (~ 500 ° C) in order to exchange one of the hydrogen atoms in the allyl position for chlorine via a radical reaction.

properties

Allyl chloride melts at −136 ° C and boils at 45 ° C. The auto-ignition temperature is 390 ° C. The density is slightly smaller than that of water and is 0.94 g · cm ⁻³ . With Lewis acids , and base metals such as aluminum or magnesium allyl chloride is violent reactions a.

use

Allyl chloride is the raw material for paint and polymer additives, silicones , water treatment products and pharmaceuticals. More than 90% of the allyl chloride produced worldwide is converted into epichlorohydrin .

safety instructions

Allyl chloride is a contact poison and can also be absorbed through the skin . In the eyes it causes swelling, redness and a blurred vision and can lead to complete blindness . In addition, skin reddening, body aches, vomiting , coughing , sore throat and headache , dizziness can occur. Long-term contact with allyl chloride can cause death .

literature

Beilstein Volume 1 (System No. 10): H, p. 198 .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 3-chloropropene in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ B. Tollens: Haloid ethers of allyl alcohol . In: Annalen der Chemie und Pharmacie 156 , 151-159 (1870).
↑ 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. 3-112.
↑ Entry on 3-chloropropene 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 107-05-1 or allyl chloride ), accessed on November 2, 2015.
↑ Lawrence H. Keith, Mary Walker: Handbook of Air Toxics Sampling, Analysis, and Properties . CRC Press, 1995, ISBN 978-1-56670-114-3 , pp. 161 ( limited preview in Google Book search).

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

[2] B. Tollens: Haloid ethers of allyl alcohol . In: Annalen der Chemie und Pharmacie 156 , 151-159 (1870).

[CRC90_3_112-3] 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. 3-112.

[CLP_100.003.144-4] Entry on 3-chloropropene 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 107-05-1 or allyl chloride ), accessed on November 2, 2015.

[Lawrence_H._Keith,_Mary_Walker-6] Lawrence H. Keith, Mary Walker: Handbook of Air Toxics Sampling, Analysis, and Properties . CRC Press, 1995, ISBN 978-1-56670-114-3 , pp. 161 ( limited preview in Google Book search).