1,1-Difluoroethylene

Last updated
1,1-Difluoroethylene
1,1-difluoroethylene.svg
1,1-Difluoroethylene.png
Names
Preferred IUPAC name
1,1-Difluoroethene
Other names
Difluoro-1,1-ethylene; R-1132a; Halocarbon 1132 A; Freon 1132A; Vinylidene difluoride; Vinylidene fluoride [1]
Identifiers
3D model (JSmol)
AbbreviationsVDF
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.789 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-867-7
KEGG
PubChem CID
RTECS number
  • KW0560000
UNII
UN number 1959
  • InChI=1S/C2H2F2/c1-2(3)4/h1H2
    Key: BQCIDUSAKPWEOX-UHFFFAOYSA-N
  • InChI=1/C2H2F2/c1-2(3)4/h1H2
    Key: BQCIDUSAKPWEOX-UHFFFAOYAV
  • C=C(F)F
Properties
C2H2F2
Molar mass 64.035 g·mol−1
AppearanceColorless gas [2]
Odor Slightly ethereal [1]
Density 2.89 kg/m3 (vapor, 0 °C) [2]
1.122 g/mL (liquid, -84 °C) [2]
Melting point −144 °C (−227 °F; 129 K) [2]
Boiling point −84 °C (−119 °F; 189 K) [2]
0.254 g/L [3]
Vapor pressure 35.2 atm (20°C) [4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable [4]
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
380 °C (716 °F; 653 K) [1]
Explosive limits 5.5%-21.3% [4]
NIOSH (US health exposure limits):
PEL (Permissible)
none [4]
REL (Recommended)
TWA 1 ppm C 5 ppm [4]
IDLH (Immediate danger)
N.D. [4]
Related compounds
Related compounds
1,2-Difluoroethylene; Fluoroethylene; Trifluoroethylene; 2-Chloro-1,1-difluoroethylene;
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,1-Difluoroethylene, also known as vinylidene fluoride, is a hydrofluoroolefin. This colorless, flammable gas is a difluorinated derivative of ethylene. Global production in 1999 was approximately 33,000 metric tons. [3] It is primarily used in the production of fluoropolymers such as polyvinylidene fluoride and FKM.

Contents

Preparation

1,1-Difluoroethylene can be prepared by elimination reaction from a 1,1,1-trihaloethane compound, for example, loss of hydrogen chloride from 1-chloro-1,1-difluoroethane: [5]

Preparation of 1,1-difluoroethylene from 1-chloro-1,1-difluoroethane.png

or loss of hydrogen fluoride from 1,1,1-trifluoroethane: [6]

Preparation of 1,1-difluoroethylene from 1,1,1-trifluoroethane.png

See also

Related Research Articles

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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 probably formed by algae and kelp, substantial amounts are produced industrially. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm. It is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.

<span class="mw-page-title-main">Chloroethane</span> Chemical compound commonly known as ethyl chloride

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<span class="mw-page-title-main">1,1,1-Trichloroethane</span> Solvent, now banned for ozone depletion

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and its use is being rapidly phased out.

<span class="mw-page-title-main">Trichloroethylene</span> C2HCl3, widely used industrial solvent

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

Hydrogen fluoride (fluorane) is an inorganic compound with chemical formula HF. It is a very poisonous, colorless gas or liquid that dissolves in water to yield an aqueous solution termed hydrofluoric acid. It is the principal industrial source of fluorine, often in the form of hydrofluoric acid, and is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers, e.g. polytetrafluoroethylene (PTFE). HF is also widely used in the petrochemical industry as a component of superacids. Due to strong and extensive hydrogen bonding, it boils at near room temperature, much higher than other hydrogen halides.

1,2-Dichloroethylene or 1,2-DCE is the name for a pair of organochlorine compounds with the molecular formula (CH2Cl)2. The two compounds are isomers, each being colorless liquids with a sweet odor. It can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have some applications as a degreasing solvent. In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.

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References

  1. 1 2 3 "Difluoro-1,1-ethylene". Gas Encyclopaedia. Air Liquide. Archived from the original on 2016-03-03. Retrieved 2012-04-23.
  2. 1 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. 1 2 "1,1'-Difluoroethylene (VDF,VF2)" (PDF). International Programme on Chemical Safety. Archived from the original (PDF) on 2012-01-04. Retrieved 2012-04-23.
  4. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0662". National Institute for Occupational Safety and Health (NIOSH).
  5. Kirk-Othmer Encyclopedia of Chemical Technology (4 ed.). John Wiley and Sons. 1994. pp. V11. Retrieved 8 July 2017.
  6. Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_349. ISBN   978-3-527-30385-4.