29514-94-1

Basic information

• Product Name: 1,1,2,2-tetrafluoro-2-[(trifluoroethenyl)oxy]ethanesulfonyl fluoride
• CAS NO: 29514-94-1
• Molecular Formula: C₄F₈O₃S
• Molecular Weight: 280.0932
• Mol File: 29514-94-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 126.7°C at 760 mmHg
• Flash Point: 30.4°C
• Density: 1.763g/cm³
• Vapor Pressure: 14mmHg at 25°C
• Refractive Index: 1.32
• CAS DataBase Reference: 1,1,2,2-tetrafluoro-2-[(trifluoroethenyl)oxy]ethanesulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2,2-tetrafluoro-2-[(trifluoroethenyl)oxy]ethanesulfonyl fluoride(29514-94-1)
• EPA Substance Registry System: 1,1,2,2-tetrafluoro-2-[(trifluoroethenyl)oxy]ethanesulfonyl fluoride(29514-94-1)

Safety Data

• Hazardous Substances Data: 29514-94-1(Hazardous Substances Data)

Usage

General Description

1,1,2,2-tetrafluoro-2-[(trifluoroethenyl)oxy]ethanesulfonyl fluoride, also known as C4F8O3S, is a synthetic chemical compound with a molecular formula of C4F8O3S. It is a colorless, odorless gas at room temperature and is widely used as a refrigerant, fire extinguishing agent, and propellant in aerosol cans. This chemical is highly reactive and can be a potential health hazard if not handled properly. It is known to be a potent greenhouse gas and has been targeted for phaseout under the Kyoto Protocol due to its high global warming potential. Additionally, exposure to this compound can cause irritation to the respiratory tract, skin, and eyes, as well as central nervous system effects. Therefore, it is important to handle and use this chemical with caution and follow strict safety protocols to minimize the risk of exposure.

Synthetic route

5-iodooctafluoro-3-oxapentanesulfonyl fluoride (66137-74-4) → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; iron(III) chloride In tetrahydrofuran at 80℃; for 6h; Temperature; Reagent/catalyst; Solvent;	96%

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl chloride (27009-57-0) → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

Conditions	Yield
With potassium fluoride In acetonitrile at 20 - 34℃; for 24h; Product distribution / selectivity;	92.7%
With potassium fluoride In sulfolane at 60℃; for 3h; Product distribution / selectivity;	91.5%
With sodium fluoride In sulfolane at 73℃; Product distribution / selectivity;	51.4%

sodium 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonate → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

Conditions	Yield
With Tetraethylene glycol dimethyl ether; hexafluoropropene-diethylamine adduct at 20 - 80℃; for 4h; Reagent/catalyst;	86%
With sulfur tetrafluoride; hydrogen fluoride at 0 - 20℃; for 16h;	85%

2-(1,2-dichloro-1,2,2-trifluoroethoxy)perfluorethanesulfonyl fluoride (144728-59-6) → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; bromine; zinc at 35 - 85℃; for 2h; Inert atmosphere; Cooling with ice;	82%
With 1-methyl-pyrrolidin-2-one; bromine; zinc at 35 - 85℃; for 2.5h; Autoclave; Inert atmosphere;	82%

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonic acid (111173-24-1) → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

Conditions	Yield
With Tetraethylene glycol dimethyl ether; hexafluoropropene-diethylamine adduct at 20 - 80℃; for 4h;	81%

5-iodooctafluoro-3-oxapentanesulfonyl fluoride (66137-74-4) + methylmagnesium bromide (75-16-1) → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

Conditions	Yield
In tetrahydrofuran 155°C, 2 h;	60%
In tetrahydrofuran 155°C, 2 h;	60%

C7H3F7N2O3S (446312-63-6) → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

Conditions	Yield
With hydrogen fluoride at 60℃; for 0.5h;	71 % Spectr.

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl chloride (27009-57-0) + sodium fluoride → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

FSO2CF2CF2OCF(CF2Cl)COONa (1246760-89-3) → 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1)

Conditions	Yield
In diethylene glycol dimethyl ether at 140℃;

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) + potassium tetrafluoro(2-fluorosulfonyl)-1-ethanolate (81439-24-9) → C6F13IO6S2

Conditions	Yield
With iodine In diethylene glycol dimethyl ether at 20℃; for 24h;	96%

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) + Silver 1-fluorosulfuryltetrafluoroethoxide → C6HF13O6S2

Conditions	Yield
With sulfuric acid In diethylene glycol dimethyl ether at 20℃; for 120h;	73%

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) → C4Br2F8O3S

Conditions	Yield
With bromine at 0 - 20℃;	65.6%
With bromine at 0℃;

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) → perfluorovinyl perfluoroiodoethyl ether (6037-91-8)

Conditions	Yield
With sodium iodide In dimethyl sulfoxide at 20 - 110℃; for 2h; Product distribution / selectivity;	60%

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) → 1-(2-fluorosulfonylperfluoroethoxy)-1,2-bis(fluorosulfonyloxy)-1,2,2-trifluoroethane + fluorosulfuric acid 1,2,2,3,4,4-hexafluoro-4-fluorosulfonyloxy-1,3-bis-(1,1,2,2-tetrafluoro-2-fluorosulfonyl-ethoxy)-butyl ester + 2,3-bis(2-fluorosulfonylperfluoroethoxy)-1,4-bis(fluorosulfonyloxy)perfluorobutane + 1,6-bis(fluorosulfonyloxy)-2,3,5-tris(2-fluorosulfonylperfluoroethoxy)perfluorohexane

Conditions	Yield
With potassium fluorosulfonate; bis(fluorosulfuryl) peroxide; fluorosulphonic acid at 28℃; Electrochemical reaction;

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) → 2,3-bis(2-fluorosulfonylperfluoroethoxy)-2,3-difluorosuccinyl difluoride + 1,1,2,2-tetrafluoro-2-[2,2,3,4-tetrafluoro-5-oxo-4-(1,1,2,2-tetrafluoro-2-fluorosulfonyl-ethoxy)-tetrahydro-furan-3-yloxy]-ethanesulfonyl fluoride

Conditions	Yield
Stage #1: 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride With potassium fluorosulfonate; bis(fluorosulfuryl) peroxide; fluorosulphonic acid at 28℃; Electrochemical reaction; Stage #2: With cesium fluoride In various solvent(s) Title compound not separated from byproducts;

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) → 2-(1,2-dichloro-1,2,2-trifluoroethoxy)perfluorethanesulfonyl fluoride (144728-59-6)

Conditions	Yield
With chlorine In HFC43-10mee at 20℃;

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) → C4F7N3O3S + C4HF7N6O3S

Conditions	Yield
With sodium azide; phosphorus pentoxide In acetonitrile at 20 - 40℃; for 51.3167h; Molecular sieve; Inert atmosphere;

1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl fluoride (29514-94-1) → C4F7O4S(1-)*K(1+) + C4HF5O6S(2-)*2K(1+)

Conditions	Yield
With potassium hydroxide In water; tert-butyl alcohol at 26 - 39℃; for 1.5h; Temperature; Solvent;

Upstream product

• 66137-74-4 5-iodooctafluoro-3-oxapentanesulfonyl fluoride 
• 75-16-1 methylmagnesium bromide 
• 111173-24-1 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonic acid 
• 144728-59-6 2-(1,2-dichloro-1,2,2-trifluoroethoxy)perfluorethanesulfonyl fluoride 
• 1246760-89-3 FSO₂CF₂CF₂OCF(CF₂Cl)COONa 
• 27009-57-0 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)ethanesulfonyl chloride 
• 7681-49-4 sodium fluoride 
• 446312-63-6 C₇H₃F₇N₂O₃S 

Downstream Products

• 6037-91-8 2-iodo-1,1,2,2-tetrafluoroethyl trifluorovinyl ether 

Relevant articles and documents

New preparation of 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)-ethanesulfonyl fluoride

A new preparation method of 1,1,2,2-tetrafluoro-2-(trifluoroethenyloxy)-ethanesulfonyl fluoride (8) has been developed utilizing the unique performance of the imidazole protective group. Namely, the electrodonating character of the imidazole protective group on the sulfonyl group enables the formation of the novel intermediate monomer, which can be easily converted to 8 by the reaction with HF.

Preparation method of resin monomer for ion exchange membrane

The invention discloses a preparation method of a resin monomer for an ion exchange membrane. The preparation method comprises the following steps: reacting fluorosulfonyl tetrafluoroethyl oxa-tetrafluoroiodoethane (ICF2CF2OCF2CF2SO2F) with a dehalogenating agent in a solvent; wherein the molar ratio of the fluorosulfonyl tetrafluoroethyl oxa-tetrafluoroiodoethane(ICF2CF2OCF2CF2SO2F) to the dehalogenating agent is (0.1-1): 1, the reacting temperature is between 20 and 200 DEG C, the reacting time is 2 to 8 hours; and cooling, discharging and distilling after the reaction is finished to obtaina resin monomer fluorosulfonyl tetrafluoroethyl oxatrifluoroethylene (CF2 is CFOCF2CF2SO2F) product for the ion exchange membrane; and the method has the advantages of simple process, readily available raw materials, low cost, environmental friendliness and easiness in industrialization.

Preparation method of direct-chain perfluoro vinyl ether by using sulfuryl fluoride group as end group

The invention belongs to the field of fine chemicals, and particularly relates to a preparation method of direct-chain perfluoro vinyl ether by using a sulfuryl fluoride group as an end group. The preparation method comprises the following steps of using the chlorinated alkyl vinyl ether as the raw material, performing the sulfonation reaction and chlorination reaction to obtain a product, and performing the addition reaction on the product with chloride gas, so as to obtain the chlorinated alkyl ether by using sulfuryl fluoride as the end group; performing the fluorination reaction on the chlorinated alkyl ether by using the sulfuryl fluoride as the end group, so as to obtain the perfluoro alkyl ether; performing the reduction reaction on the perfluoro alkyl ether, so as to obtain the direct-chain perfluoro vinyl ether by using the sulfuryl fluoride group as the end group, namely CF2=CFOCF2(CF2)nSO2F, wherein n is equal to 1 to 6. The preparation method has the advantages that by using the chlorinated alkyl vinyl ether as the raw material, the commercialized effect of the raw material is realized, the obtaining is easy, the cost is low and is lower than the cost of the fluoride-containing compound, the high-temperature cracking route and non-conventional monomer are avoided, the product is obtained via the high-yield reaction, the production of excessive fluoride-containing waste liquid is avoided, and the cost is reduced; the operation is simple and convenient, the implementing is easy, the yield rate is higher, the waste of the fluoride resource is avoided, and the production amount of the fluoride-containing waste is reduced.