697-18-7

Basic information

• Product Name: Tetrafluoroethane beta-sultone
• Synonyms: TETRAFLUORO-1,2-OXATHIETANE-2,2-DIOXIDE;3,3,4,4-TETRAFLUORO-1,2-OXATHIETANE-2,2-DIOXIDE;1,2-oxathietane,3,3,4,4-tetrafluoro-,2,2-dioxide;TETRAFLUOROETHANE SS-SULTONE;3,3,4,4-Tetrafluoro-2-oxa-1-thiacyclobutane 1,1-dioxide;Tetrafluorooxathietane 2,2-dioxide;Tetrafluoroethane beta-sultone;Perfluoro(1,2-oxathietane 2,2-dioxide)
• CAS NO: 697-18-7
• Molecular Formula: C₂F₄O₃S
• Molecular Weight: 180.08
• EINECS: 211-805-3
• Mol File: 697-18-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: -35
• Boiling Point: 41-42
• Flash Point: 68.4°C
• Appearance: /
• Density: 1.692
• Vapor Pressure: 0.789mmHg at 25°C
• Refractive Index: 1.362
• CAS DataBase Reference: Tetrafluoroethane beta-sultone(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrafluoroethane beta-sultone(697-18-7)
• EPA Substance Registry System: Tetrafluoroethane beta-sultone(697-18-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 697-18-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C2F4O3S/c3-1(4)2(5,6)10(7,8)9-1

Synthetic route

polytetrafluoroethylene (116-14-3) + 4-hexafluoroisopropylidene-1,3,2-dioxathietane 2,2-dioxide (36638-46-7) → tetrafluoroethane-β-sultone (697-18-7) + bis(trifluoromethyl)ketene (684-22-0)

Conditions	Yield
40-50°C;	A 96% B n/a
40-50°C;	A 96% B n/a

polytetrafluoroethylene (116-14-3) + sulfur trioxide (7446-11-9) → tetrafluoroethane-β-sultone (697-18-7)

Conditions	Yield
fresh distilled SO3, 2.7 atm, below 80°C, 1 h;	93%
fresh distilled SO3, 2.7 atm, below 80°C, 1 h;	93%
fresh distilled SO3, 2.7 atm, below 80°C, 1 h;	93%

polytetrafluoroethylene (116-14-3) → tetrafluoroethane-β-sultone (697-18-7)

Conditions	Yield
With sulfur trioxide for 2h; Cycloaddition;	82%
With sulfur trioxide
With sulfur trioxide

polytetrafluoroethylene (116-14-3) + α-sulfur trioxide → tetrafluoroethane-β-sultone (697-18-7)

2-fluorosulfonyl-2,2-difluoroacetyl chloride (1648-30-2) + antimony(III) fluoride (7783-56-4) → tetrafluoroethane-β-sultone (697-18-7)

polytetrafluoroethylene (116-14-3) + liquid sulfur trioxide → tetrafluoroethane-β-sultone (697-18-7)

polytetrafluoroethylene (116-14-3) + sulfur trioxide (7446-11-9) → tetrafluoroethane-β-sultone (697-18-7) + 5,5,6,6-tetrafluoro-2,2,4,4-tetroxo-1,3-dioxa-2,4-dithiane (1858-59-9)

polytetrafluoroethylene (116-14-3) + 1,1,2-Trichloro-1,2,2-trifluoroethane (76-13-1) + sulfur trioxide (7446-11-9) → tetrafluoroethane-β-sultone (697-18-7)

Conditions	Yield
with C2F4 satd. CFCl2CF2Cl adn. to SO3 under 2.4 h,standing for a night at room temp.;
with C2F4 satd. CFCl2CF2Cl adn. to SO3 under 2.4 h,standing for a night at room temp.;

polytetrafluoroethylene (116-14-3) → tetrafluoroethane-β-sultone (697-18-7) + 4,4,5,5-Tetrafluor-2-oxo-1,3,2-dioxathiolan (697-15-4)

Conditions	Yield
With O3S at 20 - 50℃; under 767.652 - 3040.2 Torr; for 6h; Large scale;

tetrafluoroethane-β-sultone (697-18-7) → 2,2-difluoro-2-(fluorosulfonyl)acetic acid (1717-59-5)

Conditions	Yield
With water	100%
With water	78%
With water
With water
With water

tetrafluoroethane-β-sultone (697-18-7) → potassium tetrafluoro(2-fluorosulfonyl)-1-ethanolate (81439-24-9)

Conditions	Yield
With potassium fluoride In diethylene glycol dimethyl ether	100%
With potassium fluoride; diethylene glycol dimethyl ether Cooling with ice;

tetrafluoroethane-β-sultone (697-18-7) + silver fluoride → Silver 1-fluorosulfuryltetrafluoroethoxide

Conditions	Yield
for 0.5h; Autoclave; Cooling with ice;	100%
In diethylene glycol dimethyl ether Cooling with ice;

tetrafluoroethane-β-sultone (697-18-7) + aniline (62-53-3) → 1,1-difluoro-2-oxo-(phenylamino)ethanesulfonic acid fluoride (3936-10-5)

Conditions	Yield
In diethyl ether at -80°C;	98%
In diethyl ether at -80°C;	98%

tetrafluoroethane-β-sultone (697-18-7) + nitrosylchloride (2696-92-6) → chlorosulfuric acid trifluorovinyl ester (923-15-9)

Conditions	Yield
at -35°C;	97%
at -35°C;	97%

tetrafluoroethane-β-sultone (697-18-7) + urea (57-13-6) → N--harnstoff (1647-56-9)

Conditions	Yield
In petroleum ether at 25°C;	96%
In Petroleum ether at 25°C;	96%
In Petroleum ether

tetrafluoroethane-β-sultone (697-18-7) + water (7732-18-5) → 2,2-difluoro-2-(fluorosulfonyl)acetic acid (1717-59-5)

Conditions	Yield
In neat (no solvent) at 5°C, with polytetrafluoroethylene filled reactor used; distn.;	96%
In Petroleum ether at -10°C;	62%
In petroleum ether at -10°C;	62%

methanol (67-56-1) + tetrafluoroethane-β-sultone (697-18-7) → 2,2-difluoro-2-(fluorosulfonyl)acetate (680-15-9)

Conditions	Yield
at 0-5°C;	95%

tetrafluoroethane-β-sultone (697-18-7) + ethanol (64-17-5) → ethyl 2,2-difluoro-2-(fluorosulfonyl)acetate (756-21-8)

Conditions	Yield
at 0-5°C;	95%

tetrafluoroethane-β-sultone (697-18-7) + methanesulfonyl chloride (124-63-0) → methyl fluorosulfonate (558-25-8) + chlorosulfuric acid trifluorovinyl ester (923-15-9)

Conditions	Yield
at room temp.;	A 90% B 95%
at room temp.;	A 90% B 95%

methylphosphonic acid dichloroanhydride (676-97-1) + tetrafluoroethane-β-sultone (697-18-7) → chlorosulfuric acid trifluorovinyl ester (923-15-9)

Conditions	Yield
In dichloromethane at -10°C;	94%
In dichloromethane at -10°C;	94%

tetrafluoroethane-β-sultone (697-18-7) + isopropyl alcohol (67-63-0) → difluoro-fluorosulfonyl-acetic acid isopropyl ester (2927-22-2)

Conditions	Yield
at 0-5°C;	93%
In diethyl ether at 10°C;	30%

tetrafluoroethane-β-sultone (697-18-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → chlorosulfuric acid trifluorovinyl ester (923-15-9)

Conditions	Yield
at 20°C;	91%
at 20°C;	91%

tetrafluoroethane-β-sultone (697-18-7) + 2,2,2-trifluoroethanol (75-89-8) → Difluoro-fluorosulfonyl-acetic acid 2,2,2-trifluoro-ethyl ester (108344-43-0)

Conditions	Yield
With sodium fluoride at 25℃; for 24h; other sulton, various alcohols;	90%

tetrafluoroethane-β-sultone (697-18-7) + 2,2,3,3-tetrafluoropropanol (76-37-9) → Difluor(fluorsulfonyl-)essigsaeure-1,1,2,2-tetrafluorpropylester (138797-15-6)

Conditions	Yield
With sodium fluoride at 25℃; for 24h;	90%

tetrafluoroethane-β-sultone (697-18-7) → fluorosulphonic acid (7789-21-1)

Conditions	Yield
With sulfuric acid at 20°C, 100 % H2SO4 used;	90%
With H2SO4 at 20°C, 100 % H2SO4 used;	90%

tetrafluoroethane-β-sultone (697-18-7) + sodium methylate (124-41-4) → Methoxysulfonyl-difluor-essigsaeure-methylester (1869-42-7)

Conditions	Yield
In diethyl ether in mixture of ice-NaCl;	86%
In diethyl ether in mixture of ice-NaCl;	86%
In methanol

tetrafluoroethane-β-sultone (697-18-7) + butan-1-ol (71-36-3) → n-C4H9OCOCF2SO2F (648-86-2)

Conditions	Yield
at 0-5°C;	86%
With sodium fluoride for 7h; Ambient temperature;	76.6%

tetrafluoroethane-β-sultone (697-18-7) + sodium ethanolate (141-52-6) → Ethoxysulfonyl-difluor-essigsaeure-ethylester (648-24-8)

Conditions	Yield
In diethyl ether in mixture of ice-NaCl;	85%
In diethyl ether in mixture of ice-NaCl;	85%
In ethanol

Hexafluoropropene oxide (428-59-1) + tetrafluoroethane-β-sultone (697-18-7) → perfluoro(4-methyl-3,6-dioxaoct-7-ene)sulfonyl fluoride (16090-14-5)

Conditions	Yield
Stage #1: Hexafluoropropene oxide; tetrafluoroethane-β-sultone With potassium fluoride In N,N-dimethyl acetamide at 20℃; under 3000.3 Torr; for 1h; Stage #2: With potassium carbonate at 150 - 360℃; for 0.583333h; Pressure; Temperature; Solvent; Reagent/catalyst;	85%

tetrafluoroethane-β-sultone (697-18-7) + aniline (62-53-3) → difluoro-phenylcarbamoyl-methanesulfonic acid ; compound with aniline (3801-86-3)

Conditions	Yield
In diethyl ether at 10°C;	84%
In diethyl ether at 10°C;	84%

tetrafluoroethane-β-sultone (697-18-7) + 1-butanethiol (109-79-5) → n-C4H9SCOCF2SO2F (648-87-3)

Conditions	Yield
at 0°C;	82%

tetrafluoroethane-β-sultone (697-18-7) + dipropyl sulfite (623-98-3) → CF2CFOSO2O-n-C3H7 (13040-35-2)

Conditions	Yield
at -20°C;	82%

tetrafluoroethane-β-sultone (697-18-7) + chlorosulfuric acid pentyl ester (860736-28-3) → fluorosulfuric acid pentyl ester (13001-91-7) + chlorosulfuric acid trifluorovinyl ester (923-15-9)

Conditions	Yield
warming on water bath under reflux, at 30-40°C, 1 h;	A 68% B 80%
warming on water bath under reflux, at 30-40°C, 1 h;	A 68% B 80%

tetrafluoroethane-β-sultone (697-18-7) + sulfurous acid dibutyl ester (626-85-7) → CF2CFOSO2C4H9 + 1-butyl fluorosulfate (13001-90-6) + sulfuric acid butyl ester trifluorovinyl ester (13001-98-4)

Conditions	Yield
at -20°C; the products can not separeted by distn.;	A n/a B n/a C 80%

tetrafluoroethane-β-sultone (697-18-7) + chlorosulfuric acid hexyl ester (857795-45-0) → n-hexyl fluorosulfonate (13001-92-8) + chlorosulfuric acid trifluorovinyl ester (923-15-9)

Conditions	Yield
warming on water bath under reflux, at 30-40°C, 1 h;	A 76% B 80%
warming on water bath under reflux, at 30-40°C, 1 h;	A 76% B 80%

tetrafluoroethane-β-sultone (697-18-7) + sulfuric acid dibutyl ester (625-22-9) → CF2CFOSO2C4H9 + 1-butyl fluorosulfate (13001-90-6) + sulfuric acid butyl ester trifluorovinyl ester (13001-98-4)

Conditions	Yield
at 0°C;	A n/a B n/a C 80%

Upstream product

• 116-14-3 polytetrafluoroethylene 
• 7446-11-9 sulfur trioxide 
• 76-13-1 1,1,2-Trichloro-1,2,2-trifluoroethane 
• 36638-46-7 4-hexafluoroisopropylidene-1,3,2-dioxathietane 2,2-dioxide 
• 1648-30-2 2-fluorosulfonyl-2,2-difluoroacetyl chloride 
• 7783-56-4 antimony(III) fluoride 

Downstream Products

• 46918-91-6 4-Methoxy-phenylaminocarbonyl-difluormethansulfonsaeure 
• 337-30-4 Phenylaminocarbonyl-difluormethansulfonsaeure 
• 422-67-3 2,2-difluoro-2-sulfoacetic acid 
• 677-67-8 fluorosulfonyldifluoroacetyl fluoride 
• 132130-89-3 2-Benzyloxy-1,1,2,2-tetrafluoro-ethanesulfonyl fluoride 
• 73606-13-0 2-Allyloxy-1,1,2,2-tetrafluoro-ethanesulfonyl fluoride 
• 73606-10-7 methyl fluorosulfonyl tetrafluoroethyl ether 
• 127197-16-4 1,1,2,2-Tetrafluoro-2-prop-2-ynyloxy-ethanesulfonyl fluoride 
• 132130-93-9 1,1,2,2-Tetrafluoro-2-pentafluorophenylmethoxy-ethanesulfonyl fluoride 
• 132130-91-7 2-(3,5-Bis-trifluoromethyl-benzyloxy)-1,1,2,2-tetrafluoro-ethanesulfonyl fluoride 
• 127197-13-1 1,1,2,2-Tetrafluoro-2-oxiranylmethoxy-ethanesulfonyl fluoride 
• 116-14-3 polytetrafluoroethylene 
• 1717-59-5 2,2-difluoro-2-(fluorosulfonyl)acetic acid 
• 73605-98-8 5-chlorooctafluoro-3-oxapentanesulfonyl fluoride 

Relevant articles and documents

Reaction system for preparing tetrafluoroethane-β-sultone and preparation method using the same

The present invention relates to a reaction system for preparing tetrafluoroethane-andbeta;-sultone and to a preparation method using the same. By using the reaction system for preparing tetrafluoroethane-andbeta;-sultone and the preparation method using the same, tetrafluoroethane-andbeta;-sultone can be prepared safely and easily at a high yield and a high purity at normal temperature and normal pressure, rapid heat generation can be avoided and the risk of explosion in processes due to pressurization is reduced, so that the reaction system and the preparation method are usefully used to prepare energy-related materials such as fuel cell electrolytes and the like derived from tetrafluoroethane-andbeta;-sultone, and in particular, are usefully used to prepare fluorine-based ionomers.COPYRIGHT KIPO 2017

Improvement of procedures for preparing Tetrafluoroethane-β-sultone and fluorocarbonyldifluoromethanesulfonyl fluoride

Synthesis of tetrafluoroethane-β-sultone by the reaction of tetrafluoroethylene with sulfuric anhydride and of fluorocarbonyldifluoromethanesulfonyl fluoride by catalytic reaction of tetrafluoroethylene with sulfuric anhydride using BAU-2, SKT-6, or AG-3 activated carbon as catalyst was studied. The possibility of replacing sulfuric anhydride prepared by distillation from oleum by sulfuric anhydride prepared by sulfur dioxide oxidation was demonstrated.

Synthesis, characterization, and ion-conductive behavior in an organic solvent and in a polyether of a novel lithium salt of a perfluorinated polyimide anion

To achieve highly conductive polymer electrolytes with a controllable ionic transference number, a novel polymeric lithium salt was synthesized and characterized. The novel lithium salt of a perfluorinated polyimide anion, poly(5-oxo-3-oxy-4-trifluoromethyl-1,2,4-pentafluoropentylene sulfonylimide lithium) (LiPPI), has a polyanionic backbone with a repeating unit resembling highly dissociable, thermally and electrochemically stable imide salts, such as lithium bis(trifluoromethylsulfonyl)imide (LiTFSI). The ion-conductive behavior of LiPPI in an organic solvent and in a polyether was extensively studied by using pulse-gradient spin-echo NMR, in addition to differential scanning calorimetry, complex impedance measurement, and dynamic mechanical analysis. Solutions of LiPPI in ethylene carbonate (EC) exhibited a high degree of dissociation and high ionic conductivity, and the self-diffusion coefficient of the anion was lower than that of the cation. Solvent-free polymer electrolytes were prepared by dissolving LiPPI in a matrix polyether to afford a compatible polymer alloy, and the ionic conductivity of the new polymer alloy electrolytes reached ca. 10-5S cm-1 at 30°C. Although the lithium ionic transference number in the organic electrolyte solution was approximately the same as that of LiTFSI in EC, the polymer alloy electrolyte gave an apparent transference number higher than 0.7, which was considerably higher than that of LiTFSI in the same polyether.