Conditions | Yield |
---|---|
With hydrogenchloride; oxygen at 199.84℃; under 750.075 Torr; for 12h; Reagent/catalyst; Flow reactor; Inert atmosphere; | 100% |
With hydrogenchloride at 180℃; Reagent/catalyst; | 99.9% |
With hydrogenchloride In water at 250℃; under 825.083 - 900.09 Torr; Temperature; Reagent/catalyst; | 68% |
Conditions | Yield |
---|---|
at 450 - 550℃; under 10501.1 - 26252.6 Torr; for 0.00416667 - 0.00833333h; | A n/a B 99.52% |
at 362 - 485℃; eine nahezu homogene Reaktion erster Ordnung, die wahrscheinlich von Chloratomen und 1.2-Dichlor-aethyl-Radikalen unterhalten wird.Thermolysis; | |
at 600℃; Conversion of starting material; | |
at 615℃; Rate constant; | |
at 650℃; Rate constant; |
Conditions | Yield |
---|---|
With triethylbenzylammonium ethanolate at -20 - 20℃; | 99% |
75% | |
With polyacrylonitrile-based active carbon fiber at 350℃; under 760 Torr; for 2h; other catalyst, var. reaction time; | 57% |
-butyl vinyl ether
Phenyltrichlorosilane
A
chloroethylene
B
dichloro(butoxy)phenylsilane
Conditions | Yield |
---|---|
at 20℃; for 24h; | A n/a B 96% |
Conditions | Yield |
---|---|
In n-heptane Quantum yield; Irradiation; | 90% |
β-chlorovinyl(methyl)dichlorosilane
A
Methyltrichlorosilane
B
1,1-dichloroethane
C
chloroethylene
Conditions | Yield |
---|---|
With hydrogenchloride; iron(III) chloride at 25 - 31℃; for 4h; Product distribution; Further Variations:; Temperatures; reaction time, reagent concentration; Addition; elimination; | A n/a B n/a C n/a D 89% |
Conditions | Yield |
---|---|
With hydrogen; Ni on pumice at 350℃; Product distribution; other temperature; | A 83.7% B 0.6% C 0.7% |
Trichloroethylene
A
cis-1,2-Dichloroethylene
B
chloroethylene
C
acetylene
Conditions | Yield |
---|---|
With iron sulfide In water for 2922h; pH=8.3; Kinetics; Product distribution; Dehydrochlorination; | A 6% B 1% C 65% |
Conditions | Yield |
---|---|
at 20℃; for 24h; | A n/a B 57% |
Methyltrichlorosilane
-butyl vinyl ether
A
chloroethylene
B
dichloro(butoxy)methylsilane
Conditions | Yield |
---|---|
at 20℃; for 24h; | A n/a B 45% |
Conditions | Yield |
---|---|
at 22℃; for 72h; Sealed tube; Inert atmosphere; | A Ca. 10 %Spectr. B Ca. 15 %Spectr. C 41% D 44% E 15% |
Conditions | Yield |
---|---|
With oxygen at 600℃; Reagent/catalyst; | 42% |
Conditions | Yield |
---|---|
With tetrachlorosilane at 20℃; for 24h; | A n/a B 37% |
-butyl vinyl ether
dichloromethylphenylsilane
A
chloroethylene
B
chloro(butoxy)(methyl)phenylsilane
Conditions | Yield |
---|---|
at 20℃; for 24h; | A n/a B 32% |
Conditions | Yield |
---|---|
With hydrogen at 500℃; under 1520.1 Torr; Reagent/catalyst; Temperature; Pressure; | 23.2% |
Conditions | Yield |
---|---|
With calcium sulfate at 260℃; under 14710.2 Torr; |
Conditions | Yield |
---|---|
With sodium ethanolate | |
With pumice stone | |
With Y-type zeolite In chloroform at 125℃; under 760.051 Torr; Temperature; | |
With aluminum oxide at 300℃; |
cis-dichloro(2-chlorovinyl) arsine
1-methyl-4-nitrosobenzene
chloroethylene
Conditions | Yield |
---|---|
at 40℃; |
Conditions | Yield |
---|---|
With aluminum oxide; chlorine at 400℃; | |
at 380℃; bei der thermischen Chlorieren; | |
bei der photochemischen Chlorierung; | |
With chlorine at 500℃; | |
With hydrogenchloride In neat (no solvent, gas phase) at 400℃; Kinetics; Catalytic behavior; Temperature; Reagent/catalyst; |
Conditions | Yield |
---|---|
With chlorine at 400℃; | |
With chlorine anschl. HCl-Abspaltung ueber Aktivkohle bei 400grad-450grad; | |
With chlorine |
Conditions | Yield |
---|---|
at 600℃; |
Conditions | Yield |
---|---|
With sodium amalgam; nickel(I)octaethylisobacteriochlorin In N,N-dimethyl-formamide at 23℃; Rate constant; | |
With water; iron at 100 - 120℃; unter Druck; | |
With water; zinc at 50 - 60℃; |
Conditions | Yield |
---|---|
Erhitzen; |
2-chloroethyl benzenesulfonate
A
chloroethylene
B
acetaldehyde
C
benzenesulfonic acid
Conditions | Yield |
---|---|
at 285 - 290℃; |
Conditions | Yield |
---|---|
With mercury(I) chloride; potassium chloride at 375℃; | |
With mercury dichloride; barium(II) chloride at 350 - 450℃; |
Conditions | Yield |
---|---|
With potassium fluoride; ethylene glycol at 150℃; | |
With potassium fluoride at 200℃; |
Conditions | Yield |
---|---|
at 450℃; |
Conditions | Yield |
---|---|
for 0.833333h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
for 120h; Ambient temperature; in vacuo; | 98% |
chloroethylene
1-chloro-1,3-bis(2,4,6-trichlorophenyl)triazene
Conditions | Yield |
---|---|
With antimonypentachloride In dichloromethane at -60 - 23℃; for 1.75h; | 98% |
3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde
chloroethylene
Conditions | Yield |
---|---|
With ammonium acetate In toluene at -2 - 5℃; Reagent/catalyst; Inert atmosphere; | 97.2% |
Conditions | Yield |
---|---|
With sodium methylate; chlorine at 25 - 27℃; for 5.5h; pH=3 - 7; Temperature; Large scale; | 97.2% |
Conditions | Yield |
---|---|
With bromine at 20℃; for 17h; Cooling; | 97% |
With bromine | |
With bromine In tetrachloromethane | |
With bromine; dinitrogen tetraoxide In chloroform | |
With bromine; Nitrogen dioxide at 325℃; |
Conditions | Yield |
---|---|
With iron; orthoformic acid triethyl ester at 130℃; under 2250.23 Torr; for 0.5h; Temperature; Pressure; Reagent/catalyst; | 96.6% |
With iron(III) chloride; phosphoric acid tributyl ester under 1125.11 Torr; for 100h; Flow reactor; Large scale; | 95.6% |
Stage #1: tetrachloromethane With N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform; iron at 140℃; for 0.5h; Autoclave; Inert atmosphere; Stage #2: chloroethylene at 140℃; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere; | 93.1% |
Conditions | Yield |
---|---|
Stage #1: chloroethylene; zinc(II) chloride In tetrahydrofuran at 20℃; for 1h; Stage #2: benzophenone In tetrahydrofuran at 0℃; for 2h; | 96% |
chloroethylene
chloro(4,4'-di-tert-butyl-2,2'-bipyridine)methylpalladium(II)
carbon monoxide
[(4,4'-di-tert-butyl-2,2'-bipyridine)Pd(CHClCH2COMe)][B(C6F5)4]
Conditions | Yield |
---|---|
In dichloromethane-d2 byproducts: LiCl, Et2O; stirring of ((t-Bu)2bipy)PdMeCl, (Li(Et2O)2.8)B(C6F5)4 (1 eqiuv.) and CH2Cl2 in Schlenk flask at -78°C for 10 min, exposure to CO (1 atm)at -78°C for 30 min, freezing to -196°C, evacuating, addn . of CH2CHCl, stirring at 23°C; filtration, drying of filtrate under vac., elem. anal.; | 96% |
Conditions | Yield |
---|---|
Stage #1: 1,8-diazabicyclo[5.4.0]undec-7-ene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: chloroethylene In tetrahydrofuran; hexane at -78 - 20℃; | 96% |
chloroethylene
4-(Methylthio)benzaldehyde
1-[4-(methylsulfanyl)phenyl]-2-propen-1-ol
Conditions | Yield |
---|---|
Stage #1: chloroethylene With magnesium In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 4-(Methylthio)benzaldehyde In tetrahydrofuran at 0 - 20℃; Grignard reaction; Stage #3: With water; ammonium chloride In tetrahydrofuran Grignard reaction; | 96% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100℃; for 10h; Reagent/catalyst; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at -40 - -10℃; for 0.5h; | 95% |
With iron(III) chloride unter Stickstoffdruck; | |
With aluminium trichloride at -25℃; | |
With iron(III) chloride | |
With aluminium trichloride |
chloroethylene
Conditions | Yield |
---|---|
In dichloromethane-d2 at 25℃; for 24h; Polymerization; dechlorination; methylation; | 95% |
chloroethylene
carbon monoxide
dimethyl amine
3-(dimthylamino)-N,Ndimethylpropanamide hydrochloride
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) at 100℃; Product distribution; Mechanism; other substituted vinyl chlorides, other amines and NH3, var. temp.; | 94% |
chloroethylene
bis-(3,5-dimethylphenyl)chlorophosphine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere; | 94% |
chloroethylene
N-phenylbenzohydrazonoyl chloride
1,3-diphenyl-1H-pyrazole
Conditions | Yield |
---|---|
With triethylamine; hydroquinone In benzene for 48h; Ambient temperature; | 93% |
chloroethylene
1,1,2,2,3,3-Hexafluoro-cyclopropane
A
polytetrafluoroethylene
B
Octafluorocyclobutane
C
1,1-difluoro-2-chlorocyclopropane
Conditions | Yield |
---|---|
at 294℃; for 1h; sealed tube in vacuo; | A 91% B 19% C 55% |
chloroethylene
[(4,4'-dimethyl-2,2'-bipyridine)Pd(Me)Cl]
carbon monoxide
[(4,4'-dimethyl-2,2'-bipyridine)Pd(CHClCH2COMe)][B(C6F5)4]
Conditions | Yield |
---|---|
In dichloromethane-d2 byproducts: LiCl, Et2O; stirring of (Me2bipy)PdMeCl, (Li(Et2O)2.8)(B(C6F5)4) (1 equiv.) and CH2Cl2 in Schlenk flask at -78°C for 10 min, exposure to CO (1 atm) at -78°C for 30 min, freezing to -196°C, evacuating, addn. of CH2CHCl, stirring at 23°C; filtration, drying of filtrate under vac., elem. anal.; | 91% |
chloroethylene
1-{2-[2-(2-vinyloxyethoxy)ethoxy]ethoxy}-2,3-epoxypropane
1-{2-[2-(2-vinyloxyethoxy)ethoxy]ethoxy}-2,3-epoxypropane - vinyl chloride copolymer, vinyl chloride 74.24 mol percent; monomer(s): 1-{2-[2-(2-vinyloxyethoxy)ethoxy]ethoxy}-2,3-epoxypropane; vinyl chloride
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In dimethyl sulfoxide at 70℃; | 88.9% |
chloroethylene
1-{2-[2-(2-vinyloxyethoxy)ethoxy]ethoxy}-2,3-epoxypropane
1-{2-[2-(2-vinyloxyethoxy)ethoxy]ethoxy}-2,3-epoxypropane - vinyl chloride copolymer, vinyl chloride 77.78 mol percent; monomer(s): 1-{2-[2-(2-vinyloxyethoxy)ethoxy]ethoxy}-2,3-epoxypropane; vinyl chloride
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In acetone at 70℃; | 88.6% |
[PdCl(CH3)(bis(diphenylphosphino)propane)]
chloroethylene
carbon monoxide
[(1,3-bis(diphenylphosphino)propane)Pd(CHClCH2COMe)][B(C6F5)4]
Conditions | Yield |
---|---|
In dichloromethane-d2 byproducts: LiCl, Et2O; stirring of (dppp)PdMeCl, (Li(Et2O)2.8)B(C6F5)4 (1 eqiuv.) and CH2Cl2 inSchlenk flask at -78°C for 10 min, exposure to CO (1 atm) at -78 °C for 30 min, freezing to -196°C, evacuating, addn. of CH2CHCl, stirring at 23°C; filtration, drying of filtrate under vac., elem. anal.; | 88% |
In 1835, Vinyl chloride (CAS NO.75-01-4) was first produced by Justus von Liebig and his student Henri Victor Regnault. They obtained it by treating ethylene dichloride with a solution of potassium hydroxide in ethanol.
In 1912, Frans, a German chemist working for Griesheim-Elektron, patented a means to produce vinyl chloride from acetylene and hydrogen chloride using mercuric chloride as a catalyst. Whereas this method was widely used during the 1930s and 1940s, it has since been superseded by more economical processes, at least in the West.
NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 373.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 19 ,1979,p. 377.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1974,p. 291.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1974,p. 291.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 19 ,1979,p. 377.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
OSHA PEL: Cancer Suspect Agent
ACGIH TLV: TWA 1 ppm; Confirmed Human Carcinogen
DFG MAK: DFG TRK: Confirmed Human Carcinogen
NIOSH REL: (Vinyl Chloride) Lowest Detectable Level
DOT Classification: 2.1; Label: Flammable Gas
For occupational chemical analysis use OSHA: #04 or NIOSH: Vinyl Chloride, 1007.
The Vinyl chloride, with the CAS registry number 75-01-4 and EINECS registry number 200-831-0, has the systematic name of chloroethene. And the molecular formula of this chemical is C2H3Cl. It is a kind of colourless gas with a sickly sweet odor, and also called VCM which is shourt for vinyl chloride monomer.
The physical properties of Vinyl chloride are as following: (1)ACD/LogP: 1.69; (2)ACD/LogD (pH 5.5): 1.69; (3)ACD/LogD (pH 7.4): 1.69; (4)ACD/BCF (pH 5.5): 11.33; (5)ACD/BCF (pH 7.4): 11.33; (6)ACD/KOC (pH 5.5): 197.82; (7)ACD/KOC (pH 7.4): 197.82; (8)Index of Refraction: 1.384; (9)Molar Refractivity: 15.889 cm3; (10)Molar Volume: 68.027 cm3; (11)Polarizability: 6.299 10-24cm3; (12)Surface Tension: 17.5160007476807 dyne/cm; (13)Density: 0.919 g/cm3; (14)Flash Point: -55.958 °C; (15)Enthalpy of Vaporization: 23.039 kJ/mol; (16)Boiling Point: -10.545 °C at 760 mmHg; (17)Vapour Pressure: 2579.74291992188 mmHg at 25°C
Preparation of Vinyl chloride: It mainly prepared by two methods, the hydrochlorination of acetylene and the dehydrochlorination of ethylene dichloride (1,2-dichloroethane). And the production of vinyl chloride from 1,2-dichloroethane (EDC) consists of a series of well-defined steps. EDC is prepared by reacting ethylene and chlorine. In the presence of iron(III) chloride as a catalyst, these compounds react exothermically: CH2=CH2 + Cl2→ ClCH2CH2Cl
Uses of Vinyl chloride: It is a chemical intermediate, and often used to produce polyvinyl chloride. And it is used as an inhalational anaesthetic, in a similar vein to ethyl chloride, though its toxicity forced this practice to be abandoned. In addition, it is also used as an aerosol propellant and is the starting material for polyvinyl resins.
You should be cautious while dealing with this chemical. It is a kind of extremely flammable chemical, and has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. What's more, it may also cause cancer. Therefore, you had better take the following instructions: Wear suitable protective clothing and gloves; Avoid exposure - obtain special instruction before use; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: Cl\C=C
(2)InChI: InChI=1/C2H3Cl/c1-2-3/h2H,1H2
(3)InChIKey: BZHJMEDXRYGGRV-UHFFFAOYAW
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LCLo | inhalation | 30pph/30M (300000ppm) | BEHAVIORAL: GENERAL ANESTHETIC | American Industrial Hygiene Association Journal. Vol. 21, Pg. 394, 1960. |
mammal (species unspecified) | LCLo | inhalation | 200ppm/18M (200ppm) | International Polymer Science and Technology. Vol. 3, Pg. 93, 1976. | |
mouse | LCLo | inhalation | 20pph/30M (200000ppm) | BEHAVIORAL: GENERAL ANESTHETIC | American Industrial Hygiene Association Journal. Vol. 21, Pg. 394, 1960. |
rat | LC50 | inhalation | 18pph/15M (180000ppm) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Human Toxicology. Vol. 1, Pg. 239, 1982. |
rat | LD50 | oral | 500mg/kg (500mg/kg) | Dow Chemical Company Reports. |
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