2-Chloroethanol

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2-Chloroethanol
2-Chloroethanol-2D-by-AHRLS-2012.png
Ball and stick model of 2-chloroethanol 2-chloroethanol-3D-balls.png
Ball and stick model of 2-chloroethanol
Spacefill model of 2-chloroethanol 2-chloroethanol-3D-vdW.png
Spacefill model of 2-chloroethanol
Names
Preferred IUPAC name
2-Chloroethan-1-ol [1]
Other names
  • 2-Chloroethanol [1]
  • beta-Chloroethanol [2]
  • 2-Chloro-1-ethanol [2]
  • β-Chloroethanol [2]
  • δ-Chloroethanol [2]
  • 2-Chloroethyl alcohol [2]
  • Ethyl chlorhydrin [2]
  • Ethylene chlorohydrin [2]
  • Glycol chlorohydrin [2]
  • Glycol monochlorohydrin [2]
  • 2-Hydroxyethyl chloride [2]
  • β-Hydroxyethyl chloride [2]
  • 2-Monochloroethanol [2]
Identifiers
3D model (JSmol)
3DMet
878139
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.146 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-459-7
25389
KEGG
MeSH Ethylene+Chlorohydrin
PubChem CID
RTECS number
  • KK0875000
UNII
UN number 1135
  • InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 Yes check.svgY
    Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N Yes check.svgY
  • OCCCl
Properties
C2H5ClO
Molar mass 80.51 g·mol−1
AppearanceColourless liquid
Odor ether-like
Density 1.201 g/mL
Melting point −62.60 °C; −80.68 °F; 210.55 K
Boiling point 127–131 °C; 260–268 °F; 400–404 K
Miscible [3]
log P −0.107
Vapor pressure 700 Pa (at 20 °C)
1.441
Thermochemistry
−1.1914 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic and flammable
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg
Danger
H226, H300+H310+H330
P260, P280, P284, P301+P310, P302+P350
NFPA 704 (fire diamond)
4
2
0
Flash point 55 °C (131 °F; 328 K)
425 °C (797 °F; 698 K)
Explosive limits 5–16%
Lethal dose or concentration (LD, LC):
  • 67 mg/kg (dermal, rabbit)[ citation needed ]
  • 72 mg/kg (rat, oral)
  • 81 mg/kg (mouse, oral)
  • 71 mg/kg (rat, oral)
  • 110 mg/kg (guinea pig, oral) [4]
  • 7.5 ppm (rat, 1  h)
  • 32 ppm (rat, 4 h)
  • 260 ppm (guinea pig)
  • 33 ppm (rat, 4 h)
  • 87 ppm (rat)
  • 115 ppm (mouse) [4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5 ppm (16 mg/m3) [skin] [3]
REL (Recommended)
C 1 ppm (3 mg/m3) [skin] [3]
IDLH (Immediate danger)
7 ppm [3]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). [6] This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group. [7]

Contents

Synthesis and applications

2-Chloroethanol is produced by treating ethylene with hypochlorous acid: [7]

Synthesis Chloroethanol B.svg

2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide:

Synthesis Ethylene oxide.svg
HOCH2CH2Cl + NaOH → C2H4O + NaCl + H2O

This application has been supplanted by the more economic direct oxidation of ethylene. Otherwise chloroethanol is still used in the production of pharmaceuticals, biocides, and plasticizers. [7] Many of these applications entail its use in installing 2-hydroxyethyl groups. [8] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol. [9] It is also used for manufacture of thiodiglycol.

It is a solvent for cellulose acetate and ethyl cellulose, textile printing dyes, in dewaxing, refining of rosin, extraction of pine lignin, and the cleaning of machines.

Environmental aspects

Chloroethanol is a metabolite in the degradation of 1,2-dichloroethane. The alcohol is then further oxidized via chloroacetaldehyde to chloroacetate. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane are processed annually as a precursor to vinyl chloride. [10]

Safety

2-Chloroethanol is toxic with an LD50 of 89 mg/kg in rats. Like most organochlorine compounds, chloroethanol releases hydrochloric acid and phosgene when burned.

In regards to dermal exposure to 2-chloroethanol, the Occupational Safety and Health Administration has set a permissible exposure limit of 5 ppm (16 mg/m3) over an eight-hour time-weighted average, while the National Institute for Occupational Safety and Health has a more protective recommended exposure limit of a 1 ppm (3 mg/m3) exposure ceiling. [11]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. [12] [ failed verification ]

Related Research Articles

Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and many other names (and abbreviations such as "perc" or "PERC", and "PCE"), is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a sweet odor detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about 1 million metric tons (980,000 long tons; 1,100,000 short tons) in 1985.

<span class="mw-page-title-main">1,2-Dibromoethane</span> Chemical compound

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C
2
H
4
Br
2
. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm, and is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.

Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC). About 13 million metric tonne are produced annually. VCM is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States currently remains the largest VCM manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of VCM. Vinyl chloride is a gas with a sweet odor. It is highly toxic, flammable, and carcinogenic. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills. In the past VCM was used as a refrigerant.

<i>p</i>-Phenylenediamine Chemical compound

p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.

<span class="mw-page-title-main">Allyl chloride</span> Chemical compound

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Chlorobenzene</span> Aromatic organochlorine compound

Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water and other chlorocarbons.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

<span class="mw-page-title-main">Propan-1-ol</span> Primary alcohol compound

Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

1,1-Dichloroethene, commonly called 1,1-dichloroethylene or vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a colorless liquid with a sharp odor. Like most chlorocarbons, it is poorly soluble in water, but soluble in organic solvents. 1,1-DCE was the precursor to the original clingwrap, Saran, for food, but this application has been phased out.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

Antimony trifluoride is the inorganic compound with the formula SbF3. Sometimes called Swarts' reagent, is one of two principal fluorides of antimony, the other being SbF5. It appears as a white solid. As well as some industrial applications, it is used as a reagent in inorganic and organofluorine chemistry.

<span class="mw-page-title-main">Glycidol</span> Chemical compound

Glycidol is an organic compound that contains both epoxide and alcohol functional groups. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

1,2,4-Trichlorobenzene is an organochlorine compound, one of three isomers of trichlorobenzene. It is a derivative of benzene with three chloride substituents. It is a colorless liquid used as a solvent for a variety of compounds and materials.

<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

<span class="mw-page-title-main">Methyl cyanoacrylate</span> Chemical compound

Methyl cyanoacrylate (MCA) is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues. It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate.

<span class="mw-page-title-main">Clopidol</span>

Clopidol is an organic compound that is used as in veterinary medicine as a coccidiostat. It is prepared industrially by a multistep process from dehydroacetic acid.

<span class="mw-page-title-main">Chloroacetaldehyde</span> Chemical compound

Chloroacetaldehyde is an organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hemiacetal (ClCH2CH(OH))2O.

References

  1. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 29. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4. For example, the omission of the locant '1' in 2-chloroethanol, while permissible in general usage, is not allowed in preferred IUPAC names, thus the name 2-chloroethan-1-ol is the PIN.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 Depositor-supplied synonyms for CID 34.
  3. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0268". National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 "Ethylene chlorohydrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. "NFPA Chemicals". New Environment Inc.
  6. Ethylene chlorohydrin: properties
  7. 1 2 3 Liu, Gordon Y. T.; Richey, W. Frank; Betso, Joanne E.; et al. (2014). "Chlorohydrins". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_565.pub2.
  8. Butler J; Kellogg R (1987). "Synthesis of Macrocyclic Sulfides Using Cesium Thiolates: 1,4,8,11-Tetrathiacyclotetradecane". Organic Syntheses. 65 (150): 150. doi:10.15227/orgsyn.065.0150.
  9. Raue, Roderich; Corbett, John F. (2002). "Nitro and Nitroso Dyes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_383.
  10. Janssen, D. B.; van der Ploeg, J. R.; Pries, F. (1994). "Genetics and Biochemistry of 1,2-Dichloroethane Degradation" (PDF). Biodegradation. 5 (3–4): 249–57. doi:10.1007/BF00696463. PMID   7765836. S2CID   475768.
  11. CDC - NIOSH Pocket Guide to Chemical Hazards
  12. "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF). Code of Federal Regulations (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.