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75-35-4 structure

VINYLIDENE CHLORIDE

Iupac Name:1,1-dichloroethene
CAS No.:75-35-4
EINECS(EC#): 200-864-0
Molecular Weight:96.938
Molecular Formula:C2H2Cl2 (isomer)
1. Names and Identifiers
1.1 Synonyms

1,1-dichloro-ethylen 1,1-dichloroethylene (vinylidine chloride) 1,1-Dichoroethene as-dichloroethylene asym-dichloroethylene CH2=CCl2 Chlorure de vinylidene chloruredevinylidene

1.2 Inchi
InChI=1S/C2H2Cl2/c1-2(3)4/h1H2
1.3 InChkey
LGXVIGDEPROXKC-UHFFFAOYSA-N
1.4 Canonical Smiles
C=C(Cl)Cl
2. 3D Conformer
3. Properties
3.1 Appearance
colourless liquid
3.2 Density
1.218
3.3 Melting Point
-122℃
3.4 Boiling Point
-188.5° F (NTP, 1992)
3.5 Vapour
9.68 psi ( 20 °C)
3.6 Refractive Index
n20/D 1.426
3.7 Flash Point
14° F (NTP, 1992)
3.8 Solubility
moderate
3.9 Color/Form
Colorless liquid
Colorless liquid or gas (above 89 degrees F).
3.10 Other physical and chemical properties
VINYLIDENE CHLORIDE;, STABILIZED is a clear colorless liquid with a chloroform;-like odor. Flash point 0°F. Boiling point 99°F. Denser (at 10.1 lb / gal) than water; and insoluble in water;. Hence sinks in water;. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently. Vapors heavier than air.
3.11 Stability
Stable. Very flammable - note low flash point. Vapour may travel considerable distances to a source of ignition. Incompatible with strong oxidizing agents, alcohols, halides, sopper, aluminium. Rapidly absorbs oxygen from the air and forms explosive peroxides. Light and water promote self-polymerisation. May form explosive mix
3.11 Stability
3.12 Storage temp
2-8°C
3.13 Spectral properties
MAX ABSORPTION (VAPOR): LESS THAN 200 NM
Index of refraction: 1.4249 at 20 deg C/D
IR: 11632 (Sadtler Research Laboratories Prism Collection)
NMR: 6385 (Sadtler Research Laboratories Spectral Collection)
UV: HBCP
MASS: 888 (NIST/EPA/MCDC Mass Spectral Database 1990 version); 203 (Atlas of Mass Spectral Data)
4. Safety and Handling
4.1 Hazard Codes
F+; Xn
4.2 Risk Statements
R12;R20;R40
4.3 Safety Statements
S16;S29;S7
4.4 HazardClass
3
4.4 Hazard Note
H224; H301; H315; H319; H332; H351
4.5 Safety
Hazard Codes:F+,Xn,T,F
Risk Statements:12-20-40-39/23/24/25-23/24/25-11
12:Extremely Flammable
20:Harmful by inhalation
40:Limited evidence of a carcinogenic effect
39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
11:Highly Flammable
Safety Statements:7-16-29-36/37-46-45
7:Keep container tightly closed
16:Keep away from sources of ignition - No smoking
29:Do not empty into drains
36/37:Wear suitable protective clothing and gloves
46:If swallowed, seek medical advice immediately and show this container or label
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR:UN 1303 3/PG 1
WGK Germany:3
HazardClass:3
PackingGroup:I
4.6 Toxicity
Vapor can cause dizziness and drunkenness; high levels cause anesthesia. Liquid irritates eyes and skin.
4.7 PackingGroup
I
4.7 Sensitive
Light Sensitive
4.8 Skin, Eye, and Respiratory Irritations
Vapor is irritating to eyes, nose, and throat.
Skin contact with vinylidene chlorde causes irritation, which may partly be due to hydroquinone monomethyl ether inhibitor.
Inhalation may cause irritation or /CNS Depression/. Irritating to skin, eyes and respiratory system.
4.9 Cleanup Methods
Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, sawdust, or commercial sorbents. Apply appropriate foam to diminish vapor and fire hazard. /Vinylidene chloride, inhibited/
Water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Inject "universal" gelling agent to solidfy encircled spill & increase effectiveness of booms. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Vinylidene chloride, inhibited/
Air spill: Apply water spray or mist to knock down vapors. Combustion products include corrosive or toxic vapors. /Vinylidene chloride, inhibited/
Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Absorb in noncombustible material for proper disposal
4.10 Transport
UN 1303
4.11 Fire Fighting Procedures
Use dry chemical, foam, carbon dioxide, or water spray. Use water spray to keep fire-exposed containers cool. Use flooding quantities of water. Fight fire from protected location or maximum possible distance. /Vinylidene chloride, inhibited/
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Vinylidene chloride, inhibited/
Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Vinylidene chloride, inhibited/
Evacuation: If fire becomes uncontrollable, or container is exposed to direct flame--consider evacuation of one-half (1/2) mile radius. /Vinylidene chloride, inhibited/
4.12 Fire Potential
Flammable liquid
A very dangerous fire hazard when exposed to heat or flame.
4.13 Formulations/Preparations
Liquid grade
Grade: technical 95%, pure 99%, research.
4.14 DOT Emergency Guidelines
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or regular foam. Large fires: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
4.15 Exposure Standards and Regulations
Vinylidene chloride is an indirect food additive for use only as a component of adhesives.
4.16 Reactivities and Incompatibilities
At ambient temp, perchloryl fluoride is unreactive with 1,1-dichloroethylene, but reaction is explosive at 100-300 deg C, or if the mixture is ignited.
Condensation of trichlorotrifluoroethylene and 1,1-dichloroethylene at 180 deg C under pressure to give 1,1,2-trichloro-2,3,3-triflurorocyclobutane was effected smoothly several times in a 1 l autoclave. Scaling up to a 3 l preparation led to uncontrolled polymerization which distorted the larger autoclave.
Mixing vinylidene chloride & chlorosulfonic acid in a closed container caused the temp & pressure to increase.
Mixing vinylidene chloride & 70% nitric acid in a closed container caused the temp & pressure to increase.
Mixing oleum & vinylidene chloride in a closed container caused the temp & pressure to increase.
Aluminum, sunlight, air, copper, heat [Note: Polymerization may occur if exposed to oxidizers, chlorosulfonic acid, nitric acid, or oleum. Inhibitors such as the monomethyl ether of hydroquinone are added to prevent polymerization].
Reaction with ozone forms dangerous products.
Potentially explosive reaction with chlorotrifluoroethylene at 180 deg C. ... Explosive reaction with perchloryl fluoride when heated above 100 deg C.
Hazardous polymerization may occur. Usually contains inhibitors to prevent polymerization. Polymerization may be caused by elevated temperature, oxidizers, peroxide or air. Uninhibited monomer vapor may form polymer in vents and other confined spaces. May form organic peroxides following prolonged contact with air. May react with aluminum and its alloys.
4.17 Other Preventative Measures
The primary requirement for reduction of exposure to vinylidene chloride would be to limit emissions through improved housekeeping procedures in the industry.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personal hazard. Use water spray to knock down vapors. /Vinylidene chloride, inhibited/
Evacuation: If material leaking (not on fire) consider evacuation from downwind area based on amt of material spilled, location & weather conditions. /Vinylidene chloride, inhibited/
Personnel protection: ... Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Vinylidene chloride, inhibited/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet should be immediately removed due to its flammability hazard (i.e., for liquids with a flash point
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
4.18 Protective Equipment and Clothing
Goggles or face shield; rubber gloves and boots.
Wear appropriate chemical protective gloves, boots & goggles.
For 1,1-dichloroethylene some data (usually from immersion tests) suggesting break-through times greater than one hour are not likely for chlorinated polyethylene (CPE).
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Respirator Recommendations: At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentrationl: Assigned Protection Factor (APF) Respirator Recommendation APF = 10,000 Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. APF = 10,000 Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister/Any appropriate escape-type, self-contained breathing apparatus.
Wear full protective clothing and positive pressure self-contained breathing apparatus.
4.19 Specification

colourless liquid
Safety Statements:7-16-29-36/37-46-45
7:Keep container tightly closed
16:Keep away from sources of ignition - No smoking
29:Do not empty into drains
36/37:Wear suitable protective clothing and gloves
46:If swallowed, seek medical advice immediately and show this container or label
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
4.20 Octanol/Water Partition Coefficient
log Kow = 2.13
4.21 Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers U078 and U029, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids. Also a potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. Also a potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds.
This compound should be susceptible to removal from waste water by air stripping.
The following wastewater treatment technologies have been investigated for 1,1-dichloroethylene: Concentration Process: Solvent extraction.
The following wastewater treatment technologies have been investigated for 1,1-dichloroethylene: Concentration Process: Stripping.
Environment Canada's Wastewater Technology Center operated a pilot plant at a landfill site to treat groundwater contaminated with volatile organic chemicals during the summer of 1986. The treatment system consisted of a packed air stripping column to treat the wastewater and two sequential granular activated carbon adsorbers to treat the off-gases. Among volatile organic chemicals in the wastewater were 1,1-dichloroethane, 1,2-dichloroethane, chloroform, 1,1-dichloroethylene, 1,1,1-trichloroethane, benzene, toluene, and trichloroethylene. Removal efficiencies varied from 27 to 99.9%. Optimal conditions, resulting in 94% removal of all volatile organic chemicals, were met with a 70:1 air-to-water ratio, a liquid flow rate of 4 l/min, and 1.3 cm Intalox saddles. Concentration of all compounds were below the lower detection limit of 2 ug/l in the effluent of the second granular activated carbon absorber.
An air stripping and incineration process is being used to clean a contaminated aquifer at McClellan Air Force Base. Groundwater is extracted and volatile organics are removed via a high-temperature air stripping system. Water soluble organics and some non-volatile organics are destroyed in a biological treatment unit. Volatile organics removed during air stripping are incinerated. Waste heat is recycled to preheat the air stripper water. Organic chemical concentrations are reduced from as high as 50 ppm to below detection limits.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 1

Acute toxicity - Inhalation, Category 4

Carcinogenicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H224 Extremely flammable liquid and vapour

H332 Harmful if inhaled

H351 Suspected of causing cancer

Precautionary statement(s)
Prevention

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.

P233 Keep container tightly closed.

P240 Ground and bond container and receiving equipment.

P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment.

P242 Use non-sparking tools.

P243 Take action to prevent static discharges.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

Response

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P370+P378 In case of fire: Use ... to extinguish.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P403+P235 Store in a well-ventilated place. Keep cool.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum
9. Computational chemical data
  • Molecular Weight:96.938g/mol
  • Molecular Formula:C2H2Cl2
  • Compound Is Canonicalized:True
  • Exact Mass:95.953
  • Monoisotopic Mass:95.953
  • Complexity:27
  • Rotatable Bond Count:0
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:0
  • Topological Polar Surface Area:0A^2
  • Heavy Atom Count:4
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
  • CACTVS Substructure Key Fingerprint: AAADcQBAAAAGAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGAIAAAAAAAKAAIAAAAAAAACA AAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA AA==
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