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Propylene chlorohydrin

Propylene chlorohydrin usually refers to the organic compound with the formula CH3CH(OH)CH2Cl. A related compound, an isomer, is CH3CH(Cl)CH2OH. Both isomers are colorless liquids that are soluble in organic solvents. They are classified as chlorohydrins. Both are generated on a large scale as intermediates in the production of propylene oxide.[1]

Propylene chlorohydrin
Names
Preferred IUPAC name
1-Chloropropan-2-ol
Other names
1-Chloro-2-hydroxypropane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.382 Edit this at Wikidata
EC Number
  • 204-819-6

    2.3.5UN Number New Window

    2611 CHEBI:76260

    CHEMBL1361129
UNII
  • InChI=1S/C3H7ClO/c1-3(5)2-4/h3,5H,2H2,1H3
    Key: YYTSGNJTASLUOY-UHFFFAOYSA-N
  • CC(CCl)O
Properties
C3H7ClO
Molar mass 94.54
Appearance colorless liquid
Density 1.1154 g/mL
Boiling point 127°C
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226, H302, H315, H319, H332, H335
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

The reaction of aqueous solution of chlorine with propene gives a 10:1 ratio of CH3CH(OH)CH2Cl and CH3CH(Cl)CH2OH. These compounds are treated with lime to give propylene oxide, which is useful in the production of plastics and other polymers.

References

edit
  1. ^ Gordon Y. T. Liu, W. Frank Richey, Joanne E. Betso, Brian Hughes, Joanna Klapacz, and Joerg Lindner "Chlorohydrins" in Ullmann's Encyclopedia of Industrial Chemistry, 2014, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_565.pub2