1,2-Difluoroethane

Last updated
1,2-Difluoroethane
1,2-difluoroethane.svg
1,2-difluoroethane-from-xtal-view-1-Mercury-3D-balls.png
Valence structural formula of 1,2-Difluoroethane.svg
1,2-difluoroethane-from-xtal-view-1-Mercury-3D-sf.png
Names
Preferred IUPAC name
1,2-Difluoroethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.259.147 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-866-1
PubChem CID
UNII
  • InChI=1S/C2H4F2/c3-1-2-4/h1-2H2 Yes check.svgY
    Key: AHFMSNDOYCFEPH-UHFFFAOYSA-N
  • C(CF)F
Properties
C2H4F2
Molar mass 66.051 g·mol−1
Appearancecolourless liquid
Density 0.913
Melting point −104 °C; −155 °F; 169 K [2]
Boiling point 30.7 °C (87.3 °F; 303.8 K)
2.31 g/L
Solubility ether, benzene, chloroform
log P 1.21
1.28 (liquid)
Structure
monoclinic
C2/c
a = 7.775, b = 4.4973, c = 9.024
α = 90°, β = 101.73°, γ = 90°
density 1.420
308.9
4
Structure
Orthorhombic
P212121
a = 8.047, b = 4.5086, c = 8.279
α = 90°, β = 101.73°, γ = 90°
density 1.461
300.4
4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Difluoroethane is a saturated hydrofluorocarbon containing an atom of fluorine attached to each of two carbons atoms. The formula can be written CH2FCH2F. It is an isomer of 1,1-difluoroethane. It has a HFC name of HFC-152 with no letter suffix. [3] When cooled to cryogenic temperatures it can have different conformers, gauche and trans. [4] In the liquid form these are about equally abundant and easily interconvert. As a gas it is mostly the gauche form. [5]

Contents

In the HFC-152 designation, 2 means two fluorine atoms, 5 means 5-1 or four hydrogen atoms, and 1 means 1+1 or two carbon atoms. [6]

Formation

Ethylene reacts explosively with fluorine yielding a mixture of 1,2-difluoroethane and vinyl fluoride. With solid fluorine it will react when triggered by near-infrared radiation. [7]

Properties

The F-C-C-F dihedral angle in 1,2-difluoroethane is 68deg in the crystal structure. 1,2-difluoroethane-from-xtal-conformation-depth-cue-Mercury-3D-balls.png
The F-C-C-F dihedral angle in 1,2-difluoroethane is 68° in the crystal structure.

Critical temperature is 107.5 °C. [2]

If a C-H bond is over excited with too much vibration, the intramolecular vibrational relaxation takes 490 picoseconds. [9]

The F-C-C-F dihedral angle is about 72°. [10] Natural bond orbital deletion bond calculations show that 1,2-difluoroethane prefers the gauche conformation due to hyperconjugation effects. Since F is much more electronegative than the C atom, it will have greater electron density for the bonding orbital (Carbon-fluorine bond). Thus, C will have larger σ* orbital, which is stabilized through C-H hyperconjugation. This cis C-H bonds and the C-F σ* interactions are significant. The dihedral angle of about 72° is a result of decreasing hyper conjugative stability and decreasing steric destabilization. [11]

Reactions

CH2FCH2F reacts with chlorine when treated with light. Two products are formed CH2FCCl2F and CHClFCHClF. The proportions of each depends on the solvent. [3]

Uses

1,2-Difluoroethane is primarily used in Refrigerants, 39%; foam blowing agents, 17%; solvents, 14%; fluoropolymers, 14%; sterilant gas, 2%; aerosol propellants, 2%; food freezant, 1%; other, 8%; exports, 3%. [12]

Safety

1,2-Difluoroethane is toxic when inhaled or when it comes into direct contact with the skin. Fluorocarbons are 4 to 5 times heavier than air, so it tends to concentrate in low-lying areas. This increases the risk of inhalation. 1,2-difluoroethane is toxic to humans through several mechanisms. First, because it has a high density, it can displace oxygen in the lungs causing suffocation. In addition, inhaled fluorocarbons causes the myocardium to become more sensitive to catecholamines, which results in deadly cardiac arrhythmias. [13]

When inhaled by rats, 1,2-difluoroethane is converted to fluoroacetate using cytochrome P450 and then to fluorocitrate both toxic. 100 parts per million in the atmosphere was sufficient to poison rats in 30 minutes and to kill them in four hours. 1,2-Difluoroethane is likely to be similarly toxic to humans. [14]

Environmental fate

1,2-Difluoroethane can enter the environment various ways. One way is through volatilization from rivers and lakes. Henry's law estimates that the volatilization half life from a model river is about 2.4 hours and 3.2 days from a model lake. [12] When 1,2-difluoroethane is released to the environment, it will end up in the atmosphere. Here it is degraded by reaction with hydroxyl radicals and oxygen. [15]

CH2FCH2F + OH → CH2FCHF + H2O

CH2FCHF + O2 → CH2FCHFO2 peroxy radical

CH2FCHFO2 + NO → CH2FCHFO alkoxy radical

When catalysed by chlorine atoms and oxidised by nitrogen oxides the end product is HCOF which can decompose further to HF and CO. [15]

The halflife in air is between 140 and 180 days. [12]

Control

1,2-Difluoroethane is a greenhouse gas when released to the atmosphere. It has a warming equivalent to 140 times that of carbon dioxide. As such it may be controlled by government regulation. The Australian government classifies 1,2-difluoroethane as an exotic synthetic greenhouse gas. [16]

Related Research Articles

Chlorofluorocarbon Class of organic compounds commonly used as refrigerants

Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and propane. They are also commonly known by the DuPont brand name Freon.

Thiol Any organic compound having a sulfanyl group

A thiol or thiol derivative is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The –SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol", where the first word deriving from Greek θεῖον (theion) meaning "sulfur".

Halomethane compounds are derivatives of methane (CH4) with one or more of the hydrogen atoms replaced with halogen atoms (F, Cl, Br, or I). Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably as refrigerants, solvents, propellants, and fumigants. Many, including the chlorofluorocarbons, have attracted wide attention because they become active when exposed to ultraviolet light found at high altitudes and destroy the Earth's protective ozone layer.

Fluoromethane Chemical compound

Fluoromethane, also known as methyl fluoride, Freon 41, Halocarbon-41 and HFC-41, is a non-toxic, liquefiable, and flammable gas at standard temperature and pressure. It is made of carbon, hydrogen, and fluorine. The name stems from the fact that it is methane (CH4) with a fluorine atom substituted for one of the hydrogen atoms. It is used in semiconductor manufacturing processes as an etching gas in plasma etch reactors.

In chemistry, orbital hybridisation is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the pairing of electrons to form chemical bonds in valence bond theory. For example, in a carbon atom which forms four single bonds the valence-shell s orbital combines with three valence-shell p orbitals to form four equivalent sp3 mixtures in a tetrahedral arrangement around the carbon to bond to four different atoms. Hybrid orbitals are useful in the explanation of molecular geometry and atomic bonding properties and are symmetrically disposed in space. Usually hybrid orbitals are formed by mixing atomic orbitals of comparable energies.

Alkane stereochemistry concerns the stereochemistry of alkanes. Alkane conformers are one of the subjects of alkane stereochemistry.

A three-center two-electron (3c–2e) bond is an electron-deficient chemical bond where three atoms share two electrons. The combination of three atomic orbitals form three molecular orbitals: one bonding, one non-bonding, and one anti-bonding. The two electrons go into the bonding orbital, resulting in a net bonding effect and constituting a chemical bond among all three atoms. In many common bonds of this type, the bonding orbital is shifted towards two of the three atoms instead of being spread equally among all three. Example molecules with 3c–2e bonds are the trihydrogen cation H+
3
) and diborane. In these two structures, the three atoms in each 3c-2e bond form an angular geometry, leading to a bent bond.

1,1-Difluoroethane Chemical compound

1,1-Difluoroethane, or DFE, is an organofluorine compound with the chemical formula C2H4F2. This colorless gas is used as a refrigerant, where it is often listed as R-152a (refrigerant-152a) or HFC-152a (hydrofluorocarbon-152a). It is also used as a propellant for aerosol sprays and in gas duster products. As an alternative to chlorofluorocarbons, it has an ozone depletion potential of zero, a lower global warming potential (124) and a shorter atmospheric lifetime (1.4 years).

Hyperconjugation

In organic chemistry, hyperconjugation refers to the delocalization of electrons with the participation of bonds of primarily σ-character. Usually, hyperconjugation involves the interaction of the electrons in a sigma (σ) orbital with an adjacent unpopulated non-bonding p or antibonding σ* or π* orbitals to give a pair of extended molecular orbitals. However, sometimes, low-lying antibonding σ* orbitals may also interact with filled orbitals of lone pair character (n) in what is termed negative hyperconjugation. Increased electron delocalization associated with hyperconjugation increases the stability of the system. In particular, the new orbital with bonding character is stabilized, resulting in an overall stabilization of the molecule. Only electrons in bonds that are in the β position can have this sort of direct stabilizing effect — donating from a sigma bond on an atom to an orbital in another atom directly attached to it. However, extended versions of hyperconjugation can be important as well. The Baker–Nathan effect, sometimes used synonymously for hyperconjugation, is a specific application of it to certain chemical reactions or types of structures.

Metal carbonyl Coordination complexes of transition metals with carbon monoxide ligands

Metal carbonyls are coordination complexes of transition metals with carbon monoxide ligands. Metal carbonyls are useful in organic synthesis and as catalysts or catalyst precursors in homogeneous catalysis, such as hydroformylation and Reppe chemistry. In the Mond process, nickel tetracarbonyl is used to produce pure nickel. In organometallic chemistry, metal carbonyls serve as precursors for the preparation of other organometallic complexes.

Hydrogen fluoride Chemical compound

Hydrogen fluoride is a chemical compound with the chemical formula HF. This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers, e.g. polytetrafluoroethylene (PTFE). HF is widely used in the petrochemical industry as a component of superacids. Hydrogen fluoride boils at near room temperature, much higher than other hydrogen halides.

Gauche effect

In the study of conformational isomerism, the Gauche effect is an atypical situation where a gauche conformation is more stable than the anti conformation (180°).

Xenon difluoride Chemical compound

Xenon difluoride is a powerful fluorinating agent with the chemical formula XeF
2
, and one of the most stable xenon compounds. Like most covalent inorganic fluorides it is moisture-sensitive. It decomposes on contact with water vapor, but is otherwise stable in storage. Xenon difluoride is a dense, colourless crystalline solid.

Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents.

Carbon–fluorine bond Covalent bond between carbon and fluorine atoms

The carbon–fluorine bond is a polar covalent bond between carbon and fluorine that is a component of all organofluorine compounds. It is one of the strongest single bonds in chemistry—behind the B-F single bond, Si-F single bond and the H-F single bond, and relatively short—due to its partial ionic character. The bond also strengthens and shortens as more fluorines are added to the same carbon on a chemical compound. As such, fluoroalkanes like tetrafluoromethane are some of the most unreactive organic compounds.

Fluorine Chemical element, symbol F and atomic number 9

Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative element, it is extremely reactive, as it reacts with all other elements, except for argon, neon, and helium.

2-Fluoroethanol Chemical compound

2-Fluoroethanol is the organic compound with the formula CH2FCH2OH. This colorless liquid is one of the simplest stable fluorinated alcohols. It was once used as a pesticide. The related difluoro- and trifluoroethanols are far less dangerous.

Fluorine forms a great variety of chemical compounds, within which it always adopts an oxidation state of −1. With other atoms, fluorine forms either polar covalent bonds or ionic bonds. Most frequently, covalent bonds involving fluorine atoms are single bonds, although at least two examples of a higher order bond exist. Fluoride may act as a bridging ligand between two metals in some complex molecules. Molecules containing fluorine may also exhibit hydrogen bonding. Fluorine's chemistry includes inorganic compounds formed with hydrogen, metals, nonmetals, and even noble gases; as well as a diverse set of organic compounds. For many elements the highest known oxidation state can be achieved in a fluoride. For some elements this is achieved exclusively in a fluoride, for others exclusively in an oxide; and for still others the highest oxidation states of oxides and fluorides are always equal.

Stereoelectronic effect

In chemistry, primarily organic and computational chemistry, a stereoelectronic effect is an effect on molecular geometry, reactivity, or physical properties due to spatial relationships in the molecules' electronic structure, in particular the interaction between atomic and/or molecular orbitals. Phrased differently, stereoelectronic effects can also be defined as the geometric constraints placed on the ground and/or transition states of molecules that arise from considerations of orbital overlap. Thus, a stereoelectronic effect explains a particular molecular property or reactivity by invoking stabilizing or destabilizing interactions that depend on the relative orientations of electrons in space.

Pentafluorosulfur hypofluorite is an oxyfluoride of sulfur in the +6 oxidation state, with a fluorine atom attached to oxygen. The formula is SOF6. In standard conditions it is a gas.

References

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