598-88-9

Usage

Chemical Properties

Colorless transparent liquid

InChI:InChI=1/C2Cl2F2/c3-1(5)2(4)6/b2-1+

Synthetic route

(2,2-dichloro trifluoro ethyl) trifluoro silane (54939-02-5) → 1,1'-dichloro-2,2'-difluoroethene (79-35-6) + 1,2-dichloro-1,2-difluoroethene (598-88-9) + silicon tetrafluoride (7783-61-1)

Conditions	Yield
In neat (no solvent) pyrolysis at 140°C, 3 hours;;	A 8% B 90% C 100%
In neat (no solvent) pyrolysis at 140°C, 3 hours;;	A 8% B 90% C 100%

1,2,2-trichloro-1,2-difluoroethane (354-15-4) → 1,2-dichloro-1,2-difluoroethene (598-88-9)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In water at 30℃; for 0.666667h; Product distribution / selectivity;	98%
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In water at 30℃; for 0.666667h; Product distribution / selectivity;	98%
With tetra(n-butyl)ammonium hydroxide; sodium hydroxide In water at 30℃;	98%

CFC-112a (76-12-0) → 1,2-dichloro-1,2-difluoroethene (598-88-9)

Conditions	Yield
zinc In isopropyl alcohol at 75 - 80℃; for 1h; Product distribution / selectivity;	92%
With zinc In isopropyl alcohol at 75 - 80℃; for 1h; Product distribution / selectivity;	92%
With zinc In isopropyl alcohol at 75 - 80℃; Inert atmosphere of nitrogen;	92%

(2,2-dichloro trifluoro ethyl) trichloro silane (662-06-6) → 1,1'-dichloro-2,2'-difluoroethene (79-35-6) + 1,2-dichloro-1,2-difluoroethene (598-88-9)

Conditions	Yield
In neat (no solvent) pyrolysis at 250°C;;	A 7% B 80%
In neat (no solvent) pyrolysis at 185°C;;	A 7% B 80%
In neat (no solvent) pyrolysis at 185°C;;	A 7% B 80%
In neat (no solvent) pyrolysis at 250°C;;	A 7% B 80%
at 250℃;

Dichlorofluoromethane (75-43-4) → CFC-112a (76-12-0) + 1,2-dichloro-1,2-difluoroethene (598-88-9)

Conditions	Yield
at 675℃;

CFC-112a (76-12-0) → 1,2,2-trichloro-1,2-difluoroethane (354-15-4) + 1,2-dichloro-1,2-difluoroethene (598-88-9) + carbon dioxide (124-38-9) + carbon monoxide (201230-82-2)

Conditions	Yield
With ethanol; iron(III) chloride on activated carbon at 175℃; Product distribution; other chlorofluorocarbon; var. temp.; conversion vs. time of contact;

Chlorotrifluoroethylene (79-38-9) → 1,1,2-Trichloro-1,2,2-trifluoroethane (76-13-1) + 1,2-dichloro-1,2-difluoroethene (598-88-9) + 3-chloro-1,1,2,3,3-pentafluoro-propene (79-47-0) + octafluoro-1-butene (357-26-6) + Octafluorocyclobutane (115-25-3) + 1,2-dichloroperfluorocyclobutane (356-18-3)

Conditions	Yield
at 450 - 710℃; for 0.000333333h; Product distribution; Mechanism; pyrolysis; variation of time and temp.; effect of contact time and temp.;	A 5.2 % Chromat. B 2.5 % Chromat. C 27.0 % Chromat. D 1.7 % Chromat. E 1.6 % Chromat. F 30.1 % Chromat.

Chlorotrifluoroethylene (79-38-9) → polytetrafluoroethylene (116-14-3) + 1,2-difluoroethene (1691-13-0) + 1-chloro-1,2-difluoroethene (359-04-6) + 1,2-dichloro-1,2-difluoroethene (598-88-9) + 1,1,2-trifluoroethylene (359-11-5)

Conditions	Yield
With monosilane under 0.7 Torr; Mechanism; Product distribution; Irradiation;

trichlorofluoromethane (75-69-4) + acetone (67-64-1) → 1,1-dichloro-1-fluoro-2-methyl-propan-2-ol (421-71-6) + 1,2-dichloro-1,2-difluoroethene (598-88-9)

Conditions	Yield
With magnesium In tetrahydrofuran at -20 - -15℃; Product distribution; other substrates, other products; also promoted by the Mg/LiCl-system;

1,2,2-trichloro-1,2-difluoroethane (354-15-4) + alcoholic KOH-solution → 1,2-dichloro-1,2-difluoroethene (598-88-9)

trichlorofluoromethane (75-69-4) → 1,2-dichloro-1,2-difluoroethene (598-88-9) + trichlorofluoroethene (359-29-5) + chlorine (7782-50-5)

Conditions	Yield
In neat (no solvent) pyrolysis in an graphite furnace at 850°C; determination by MS;;

Dichlorofluoromethane (75-43-4) → 1,2-dichloro-1,2-difluoroethene (598-88-9)

Conditions	Yield
at 600℃; under 750.075 Torr; Flow reactor; Green chemistry;

hypofluorous acid trifluoromethyl ester (373-91-1) + 1,2-dichloro-1,2-difluoroethene (598-88-9) → 1-trifluoromethoxy-1,2-dichlorotrifluoroethane (2356-53-8)

Conditions	Yield
In trichlorofluoromethane at -70℃; for 0.166667 - 4h; Product distribution / selectivity;	98.4%
In CFCl3 at -70℃; for 0.166667 - 4h; Product distribution / selectivity;	98.4%
at -70℃; Inert atmosphere; Flow reactor;	97%
at 140 - 170℃; under 5250.53 Torr; for 190h;	87.23%

1,2-dichloro-1,2-difluoroethene (598-88-9) + 4-trifluoromethylperfluoro-2-pentenoic acid fluoride (88022-48-4) → 1,2-dichloro-6-trifluoromethylperfluoro-4-hepten-3-one (134330-90-8, 134330-94-2)

Conditions	Yield
With antimony pentafluoride at 30℃;	94%

1,2-dichloro-1,2-difluoroethene (598-88-9) → 1,2-dichloro-1,2-difluoro-2-nitroethyl fluosulfate

Conditions	Yield
With NO2SOF3 for 1h;	92%

1,2-dichloro-1,2-difluoroethene (598-88-9) + nonafluoro-tert-butyl hypofluorite (2203-56-7) → C6Cl2F12O (1223032-50-5)

Conditions	Yield
at -55℃; Cooling with liquid nitrogen;	91%

1,2-dichloro-1,2-difluoroethene (598-88-9) + 1-benzyl-3-hydroxy-1H-indazole (2215-63-6) → 1-benzyl-3-(1,2-difluoro-2-chlorovinyloxy)-1H-indazole (1300727-57-4)

Conditions	Yield
Stage #1: 1-benzyl-3-hydroxy-1H-indazole With sodium hydride In vaseline oil; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 1,2-dichloro-1,2-difluoroethene In vaseline oil; N,N-dimethyl-formamide at 95℃; for 8h;	89%

1,2-dichloro-1,2-difluoroethene (598-88-9) → 1,2-Dibromo-1,2-dichloro-1,2-difluoroethane (421-69-2)

Conditions	Yield
With bromine In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃; for 3h; Bromination;	87%
With bromine
With bromine
With bromine at 60℃; for 0.166667h;	945 g

1,2-dichloro-1,2-difluoroethene (598-88-9) + N,N-bis(trifluoromethyl)amino difluoromethyl hypofluorite (1338082-65-7) → C5Cl2F11NO (1338082-68-0)

Conditions	Yield
at 20℃; Cooling with liquid nitrogen;	86.2%

1,2-dichloro-1,2-difluoroethene (598-88-9) → C2Cl2F8OS (116385-67-2)

Conditions	Yield
With pentafluorosulfur hypofluorite at -196 - 22℃;	86%

1,2-dichloro-1,2-difluoroethene (598-88-9) + 1-fluoroxy heptafluoropropane (2203-57-8) → perfluoropropyl 1,2-Dichlorotrifluoroethyl Ether (106372-30-9)

Conditions	Yield
In Chloropentafluoroethane at -90℃; for 4h;	84.3%
at -90℃; Inert atmosphere; Flow reactor;	45%
In CF2Cl-CF3 at -90℃; for 4h; Product distribution / selectivity;
In CF2Cl-CF3 (CFC 115) at -90℃; for 4h;

1,2-dichloro-1,2-difluoroethene (598-88-9) + pentafluoroethyl oxyfluoride (3848-94-0) → 1,2-dichlorotrifluoroethyl pentafluoroethyl ether

Conditions	Yield
at -90℃; Inert atmosphere; Flow reactor;	80%
In CF2Cl-CF3 at -90℃; for 3h; Product distribution / selectivity;
In CF2Cl-CF3 (CFC 115) at -90℃; for 3h;

methanol (67-56-1) + 1,2-dichloro-1,2-difluoroethene (598-88-9) → 2,3-dichloro-2,3-difluoropropan-1-ol (1647-61-6)

Conditions	Yield
With 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane at 134℃; under 5250.53 - 9000.9 Torr; Inert atmosphere;	78%
With 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane at 133.85℃; for 7h; Product distribution; Further Variations:; initial molar conc. ratio /; initial molar conc. ratio / C0 = 0.1;	65%
With di-tert-butyl peroxide at 150℃; for 5h;	10%
for 327h; Irradiation;

Upstream product

• 75-43-4 Dichlorofluoromethane 
• 662-06-6 (2,2-dichloro trifluoro ethyl) trichloro silane 
• 76-12-0 CFC-112a 
• 79-38-9 Chlorotrifluoroethylene 
• 354-15-4 1,2,2-trichloro-1,2-difluoroethane 
• 75-69-4 trichlorofluoromethane 
• 54939-02-5 (2,2-dichloro trifluoro ethyl) trifluoro silane 
• 67-64-1 acetone 

Downstream Products

• 354-23-4 1,2-dichloro-1,2,2-trifluoroethane 
• 677-47-4 1-iodo-1,2-difluoro-1,2,2-trichloroethane 
• 76-12-0 CFC-112a 
• 421-69-2 1,2-Dibrom-1,2-dichlor-1,2-difluor-ethan 
• 76-15-3 Chloropentafluoroethane 
• 76-14-2 1,2-dichloro-1,1,2,2-tetrafluoroethane 
• 76-13-1 1,1,2-Trichloro-1,2,2-trifluoroethane 
• 376-79-4 1,3,4,5,6,6-hexachloro-1,2,3,4,5,6-hexafluoro-hex-1-ene 
• 375-45-1 perfluoro-1,2,3,4-tetrachlorobutane 
• 392-41-6 methyl trifluoropropenoate 
• 422-41-3 1,2,3,3-tetrachloro-1,1,2-trifluoro-propane 
• 355-25-9 perfluorobutane 
• 1998-80-7 1,2-dichloro-1,1,2,3,4,4,5,5,5-nonafluoro-3-trifluoromethyl-pentane 
• 1735-48-4 perfluoro-3,4-dimethylhexane 

Relevant academic research and scientific papers

At the same time, preparation of trifluoro-vinyl chloride and tetrafluoroethylene, and method

The invention discloses a method for simultaneously preparing trifluorochloroethylene and tetrafluoroethylene. The method comprises the following steps: mixing monochlorodifluoromethane, dichlorofluoromethane and a diluent, performing copyrolysis reaction to generate pyrolysis gas, quickly cooling, washing by water and alkali in sequence, drying, compressing, rectifying and purifying to obtain trifluorochloroethylene and tetrafluoroethylene, wherein the molar ratio of monochlorodifluoromethane to dichlorofluoromethane is 1 to (1-4), the molar ratio of the diluent to the total amount of monochlorodifluoromethane and dichlorofluoromethane is 1 to (1-20), the reaction temperature is 500-1,200 DEG C, the reaction pressure is 0.1-1MPa, and the reaction retention time is 0.01-10 seconds. The method has the advantages of being simple in process, easy for industrialization and environment-friendly, and raw materials are easily available.

PROCESS FOR THE SYNTHESIS OF PERFLUOROBUTADIENE

Process for preparing perfluoro-1,3-butadiene, comprising the following steps : A) preparation of fluoro-halo-butanes of formula : CF2 YI-CFYIICFYIICF2 YI (V) in which YI and YII which may be identical or different, may be H, C1 or Br, with the condition that YI and YII are not simultaneously hydrogen; starting with a chloroolefin having the formula : CY'Y = CY'C1 (II) in which Y, Y', Y', which may be identical or different, are H, C1 or Br, with the condition that Y, Y', Y' are not simultaneously hydrogen; and performing the following steps : - a fluorodimerization, and - a fluorination with elemental fluorine, the order of the two steps also possibly being inverted, - a dehalogenation or dehydrohalogenation step being performed between the two steps, B) dehalogenation or dehydrohalogenation of the fluoro-halo compounds of formula (V) to give the compound perfluoro-1,3-butadiene.

Process for preparing fluorohalogenethers

A process for preparing perfluorovinylethers having general formula: ???????? RfO-CF=CF2?????(IA) wherein Rf is a C1-C3 alkyl perfluorinated substituent; comprising the following steps: 1a) fluorination with fluorine of olefins of formula: ???????? CY"Y=CY'Cl?????(II) wherein Y, Y' and Y", equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y' and Y" are not contemporaneously hydrogen; and obtainment of fluorohalogencarbons of formula: ???????? FCY"Y-CY'ClF?????(III) wherein Y, Y' and Y" are as above; 2a) dehalogenation or dehydrohalogenation of the fluorohalogencarbons (III) and obtainment of fluorohalogen olefins of formula: ???????? FCYI=CYIIF?????(IV) wherein YI and YII, equal to or different from each other, have the meaning of H, Cl, Br with the proviso that YI and YII are not both H; 3a) reaction between a hypofluorite of formula RfOF and a fluorohalogenolefin (IV), obtaining the fluorohalogenethers of formula: ???????? RfO-CFYI-CF2YII?????(I) wherein YI, YII, equal to or different from each other, are Cl, Br, H with the proviso that YI and YII cannot be contemporaneously equal to H; 4a) dehalogenation or dehydrohalogenation of the compounds (I) and obtainment of the perfluorovinylethers (IA).

Process for preparing fluorohalogenethers

A process for preparing perfluorovinylethers having general formula: [in-line-formulae]RfO—CF═CF2 ??(IA)[/in-line-formulae] wherein Rf is a C1-C3 alkyl perfluorinated substituent; comprising the following steps: 1a) fluorination with fluorine of olefins of formula: [in-line-formulae]CY″Y═CY′Cl ??(II)[/in-line-formulae]wherein Y, Y′ and Y″, equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y′ and Y″ are not contemporaneously hydrogen; and obtainment of fluorohalogencarbons of formula: [in-line-formulae]FCY″Y—CY′ClF ??(III)[/in-line-formulae]wherein Y, Y′ and Y″ are as above; 2a) dehalogenation or dehydrohalogenation of the fluorohalogencarbons (III) and obtainment of fluorohalogen olefins of formula: [in-line-formulae]FCYI═CYIIF ??(IV)[/in-line-formulae]wherein YI and YII, equal to or different from each other, have the meaning of H, Cl, Br with the proviso that YI and YII are not both H; 3a) reaction between a hypofluorite of formula RfOF and a fluorohalogenolefin (IV), obtaining the fluorohalogenethers of formula: [in-line-formulae]RfO—CFYI—CF2YII ??(I)[/in-line-formulae]wherein YI, YII, equal to or different from each other, are Cl, Br, H with the proviso that YI and YII cannot be contemporaneously equal to H; 4a) dehalogenation or dehydrohalogenation of the compounds (I) and obtainment of the perfluorovinylethers (IA).

Fluorinated butanolides and butenolides. Part 5. Synthesis and nucleophilic reactions of 3-chloro-2-fluoro-2-buten-4-olide as tetronic acid analogue. Conjugate addition of hard nucleophiles and vinylic halogen displacement with soft phosphorus nucleophiles

3-Chloro-2-fluorobut-2-en-4-olide (13) and 2-fluorobut-2-en-4-olide (14) were prepared by a six step synthesis starting from 1,2-dibromo-1,2-dichloro-1,2-difluoroethane (5). UV-initiated addition of 5 to ethylene afforded 1,4-dibromo-1,2-dichloro-1,2-difluorobutane (6a) that was easily dehydrochlorinated to 4-bromo-3,4-dichloro-3,4-difluorobut-1-ene (7) and subsequently by chlorine addition to 1-bromo-1,2,3,4-tetrachloro-1,2-difluorobutane (10). Fuming sulfuric acid affected CH2-Br bond in 6a to afford 4-bromo-3,4-dichloro-3,4-difluorobutan-1-ol (8), while with 10 bearing stable terminal CH2-Cl group the reaction took place at the trihalomethyl group to give 2,3,4-trichloro-2-fluorobutanoic acid (11a). Its sodium salt (11b) cyclized in solution or thermally in the solid state to 2,3-dichloro-2-fluorobutan-4-olide (12) that by dehydrochlorination with tertiary amine gave new butenolide 13 or by didechlorination with zinc 2-fluorobut-2-en-4-olide (14). Hard nucleophiles as methanol and piperidine afforded products of conjugate addition, while soft phosphorus nucleophiles, triethyl phosphite or tributylphosphane, affected vinylic C-Cl and C-F bonds to give products of nucleophilic vinylic substitution.

Reductive addition of trichlorofluoromethane to ketones initiated by the Mg/LiCl system

Reductive addition of trichlorofluoromethane to ketones initiated by the Mg/LiCl system at -20 deg C to -15 deg C gave dichlorofluoromethyl carbinols in moderate yield.

Catalytic Decomposition of CFC-112 and CFC-113 in the Presence of Ethanol

Iron (III) chloride supported on activated charcoal was extremely effective for decomposition of CFC-112 and CFC-113 into CO and CO2 in the presence of ethanol at the low temperature.

IR Laser-induced Chemistry of some Perhaloethene-Silane Mixtures at Different Single Irradiating Wavelengths

TEA CO2 laser-induced reactions in chlorotrifluoroethene-silane, 1,2-dichlorodifluoroethene-silane, 1,1-dichlorodifluoroethene-silane, and 1,2-dichlorodifluoroethene-trimethylsilane mixtures at medium (4-19 Torr) and in chlorotrifluoroethene-silane and 1,2-dichlorodifluoroethene-silane mixtures at low (1 Torr) pressures can be initiated by irradiation tuned to either perhaloethene or silane.The reaction progress at medium pressure and reaction products at low pressure depend on the particular wavelength employed.The former reactions are assumed to occur through reactive collision of both energized components in the mixture and have been shown to yield mostly tetrafluorosilane, trifluorosilane, hydrogen chloride, and other hydrocarbons.The latter are explained by multiphoton dissociation of the alkene into carbenes, subsequent reactions of these carbenes, and by 1,2-rearrangement of halogen in the transient CFCl=CF* radical produced upon C-Cl bond cleavage of the parent CFCl=CFCl compound.This reaction mechanism is in line with IR multiphoton decomposition of 1,2-dichlorodifluoroethene both in the absence and presence of chlorine and carbon monoxide.