Chlorethanes and Chloroethylenes

Abstract

The article contains sections titled: 1. Chloroethanes 1.1. Monochloroethane 1.1.1. Physical Properties 1.1.2. Chemical Properties 1.1.3. Production 1.1.4. Uses and Economic Aspects 1.2. 1,1‐Dichloroethane 1.2.1. Physical Properties 1.2.2. Chemical Properties 1.2.3. Production 1.2.4. Uses and Economic Aspects 1.3. 1,2‐Dichloroethane 1.3.1. Physical Properties 1.3.2. Chemical Properties 1.3.3. Production 1.3.4. Uses and Economic Aspects 1.4. 1,1,1‐Trichloroethane 1.4.1. Physical Properties 1.4.2. Chemical Properties 1.4.3. Production 1.4.4. Uses and Economic Aspects 1.5. 1,1,2‐Trichloroethane 1.5.1. Physical Properties 1.5.2. Chemical Properties 1.5.3. Production 1.5.4. Uses and Economic Aspects 1.6. 1,1,1,2‐Tetrachloroethane 1.6.1. Physical Properties 1.6.2. Chemical Properties 1.6.3. Production 1.7. 1,1,2,2‐Tetrachloroethane 1.7.1. Physical Properties 1.7.2. Chemical Properties 1.7.3. Production 1.7.4. Uses and Economic Aspects 1.8. Pentachloroethane 1.8.1. Physical Properties 1.8.2. Chemical Properties 1.8.3. Production 1.8.4. Uses and Economic Aspects 1.9. Hexachloroethane 1.9.1. Physical Properties 1.9.2. Chemical Properties 1.9.3. Production 1.9.4. Uses and Economic Aspects 2. Chloroethylenes 2.1. Vinyl Chloride (VCM) 2.1.1. Physical Properties 2.1.2. Chemical Properties 2.1.3. Production 2.1.3.1. Vinyl Chloride from Acetylene 2.1.3.2. Vinyl Chloride from 1,2‐Dichloroethane 2.1.3.3. Vinyl Chloride from Ethylene by Direct Routes 2.1.3.4. Vinyl Chloride from Ethane 2.1.3.5. Vinyl Chloride by Other Routes 2.1.4. Uses and Economic Aspects 2.2. 1,1‐Dichloroethylene (Vinylidene Chloride, VDC) 2.2.1. Physical Properties 2.2.2. Chemical Properties 2.2.3. Production 2.2.4. Uses and Economic Aspects 2.3. 1,2‐Dichloroethylene 2.3.1. Physical Properties 2.3.2. Chemical Properties 2.3.3. Production 2.3.4. Uses and Economic Aspects 2.4. Trichloroethylene 2.4.1. Physical Properties 2.4.2. Chemical Properties 2.4.3. Production 2.4.4. Uses and Economic Aspects 2.5. Tetrachloroethylene 2.5.1. Physical Properties 2.5.2. Chemical Properties 2.5.3. Production 2.5.4. Uses and Economic Aspects 3. Analysis and Quality Control of Chloroethanes and Chloroethylenes 4. Storage and Transportation of Chloroethanes and Chloroethylenes 5. Environmental Aspects in the Production of Chloroethanes and Chloroethylenes 6. Toxicology

Trihaloethenes as versatile building blocks for organic synthesis

“…1 Since then, TCE (1) has gained major importance in various industrial applications. 2 The ease of preparation of large quan-tities of this non-flammable, volatile organic compound led to a staggering global consumption of 428.6 × 10 3 t in 2011. Of this, 84% of the total production volume in the USA were used as an intermediate for manufacturing the refrigerant 1,1,1,2tetrafluoroethane (HFC-134a) and 15% as a solvent for metal degreasing.…”

“…Of this, 84% of the total production volume in the USA were used as an intermediate for manufacturing the refrigerant 1,1,1,2tetrafluoroethane (HFC-134a) and 15% as a solvent for metal degreasing. 2,3 The preparation of HFC-134a from 1 occurs by addition of hydrogen fluoride to the alkene, followed by halogen-exchange reactions to afford 2-chloro-1,1,1-trifluoroethane (HCFC-133a) (eqn (1)). By further treatment with hydrogen fluoride, HCFC-133a is then converted into HFC-134a (eqn (2)).…”

“…3,5 Amongst other factors, the toxicity associated with 1 has led to continuously decreasing production rates in the industry. 2,6 CCl 2 vCHCl þ 3HF ÀÀÀÀÀÀ! In the field of synthetic organic chemistry, TCE (1) serves as a chlorinated C 2 -building block 7,8 that found very interesting applications beyond cross coupling reactions.…”

“…−51°C), respectively, have received much less attention from synthetic chemists. Although tribromoethene (2) has been known for over 150 years, its use in synthesis has been relatively limited. 10 Trifluoroethene (3), on the other hand, has found application in the synthesis of copolymers in combination with polyvinylidene fluoride (PVDF).…”

“…One such feedstock is acetylene, which is converted to 1 via a chlorination-dehydrochlorination pathway. 2 A different approach is the oxychlorination of ethene to afford 1. In this reaction, the chlorine source is hydrogen chloride, which is oxidized according to the Deacon process.…”