692-50-2

Basic information

• Product Name: HEXAFLUORO-2-BUTYNE
• Synonyms: butyne06;CF3CequivCCF3;hexafluoro-2-butyn;Hexafluorobutyne-2;Perfluoro-2-butyne;1,1,1,4,4,4-hexafluorobut-2-yne;Hexafluorobut-2-yne99%;1,2-Bis(trifluoromethyl)ethyne
• CAS NO: 692-50-2
• Molecular Formula: C₄F₆
• Molecular Weight: 162.03
• EINECS: 211-732-7
• Product Categories: Chemical Synthesis;Compressed and Liquefied Gases;Synthetic Reagents
• Mol File: 692-50-2.mol

Chemical Properties

• Melting Point: −117 °C(lit.)
• Boiling Point: −25 °C(lit.)
• Flash Point: -36℃
• Appearance: colorless gas
• Density: 1,602 g/cm3
• Vapor Pressure: 105 psi ( 20 °C)
• Refractive Index: 1.2810 (estimate)
• CAS DataBase Reference: HEXAFLUORO-2-BUTYNE(CAS DataBase Reference)
• NIST Chemistry Reference: HEXAFLUORO-2-BUTYNE(692-50-2)
• EPA Substance Registry System: HEXAFLUORO-2-BUTYNE(692-50-2)

Safety Data

• Hazard Codes: F+,T,F
• Statements: 12-23
• Safety Statements: 16-33-45
• RIDADR: UN 3160 2.3
• WGK Germany: 3
• RTECS: ES0702500
• TSCA: T
• HazardClass: 2.3
• Hazardous Substances Data: 692-50-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 83, p. 391, 1961 DOI: 10.1021/ja01463a033

InChI:InChI=1/C4F6/c5-3(6,7)1-2-4(8,9)10

Upstream product

• 400-44-2 2?chloro?1,1,1,4,4,4?hexafluoro?2?butene 
• 2418-21-5 trans-2,3-dichlorohexafluoro-2-butene 
• 162462-08-0 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane 
• 2418-22-6 cis-2,3-dichloro-1,1,1,4,4,4-hexafluorobutene-2 
• 3414-09-3 1,1,1,4,4,4-hexafluoro-2-chloro-2-butene 
• 7736-43-8 trans-2-chloro-1,1,1,4,4,4-hexafluorobutene-2 
• 407-59-0 1,1,1,4,4,4-hexafluorobutane 
• 354-58-5 1,1,1-Trichloro-2,2,2-trifluoroethane 
• 697-11-0 hexafluorocyclobut-1-ene 
• 685-63-2 hexafluoro-1,3-butadiene 
• 375-34-8 1,1,1,4,4,4-hexa-fluoro-2,2,3,3-tetrachlorobutane 
• 384-54-3 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane 
• 680-17-1 1,1,1-trifluoro-2-fluoro-3,3-difluoro-4,4,4-trifluorobutane 
• 303-04-8 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene 

Downstream Products

• 38860-29-6 2,3,7-triphenyl-5,6-bis-trifluoromethyl-1-arsa-bicyclo[2.2.2]octa-2,5,7-triene 
• 83248-91-3 N-benzoyl-2,3-bis(trifluoromethyl)-7-azabicyclo<2.2.1>-2.5-heptadiene 
• 217-59-4 triphenylene 
• 384-51-0 1,2-dibromo-1,2-bis(trifluoromethyl)ethylene 
• 684-22-0 bis(trifluoromethyl)ketene 
• 685-24-5 1,1,1,4,4,4-hexafluoro-2,3-butanedione 
• 78844-51-6 perfluoroacetylmethylmethylene 
• 2375-86-2 1,2,3,4-Tetrakis-(trifluormethyl)-3,4-diphospha-cyclobuten 
• 122172-00-3 {Ir2(CO)(η2-F3CCCCF3)(μ-S)(μ-CO)(DPM)2} 

Relevant articles and documents

Vicinal dichlorine elimination at dichloroalkenes promoted by a well-defined iron(0) complex

Dechlorination reactions at sp2 C-Cl bonds by a pentaphosphino zero-valent iron (ZVI) complex are proposed to follow an oxidative addition, β-Cl-elimination pathway en route to iron-chloride, iron-hydride and iron-acetylide products, the distribution being dependent on the nature of alkyne produced.

Unusual photocyclization of perfluoro cis-1,2-dimethyl-1,3-butadienyl benzenes as a means to synthesize partially fluorinated naphthalenes

Photoirradiation of the titled compounds perfluoro-cis-1,2-dimethyl-butadienyl benzenes (1), which were prepared in several steps from perfluorovinyl bromide, results in the formation of the corresponding novel naphthalene derivatives and 1,4-dihydronaphthalenes. Isolated 1,1,2-trifluoro-3,4-bis(trifluoromethyl)-1,4-dihydronaphthalene (3a) could be converted into 1,2-bistrifluoromethyl-3,4-difluoronaphthalene (2a) by base treatment (DABCO); however, 3a did not lead to 2a by photoreaction, suggesting 3a was not a possible photochemical precursor. Competitive photoreaction studies suggest that varying the substituent on benzene ring (e.g. methyl or trifluoromethyl) does not significantly affect the reaction rate. Presently, this reaction mechanism is not yet clearly understood.

Preparation of cis-1,1,1,4,4,4-hexafluorobut-2-ene by cis-selective semi-hydrogenation of perfluoro-2-butyne

Cis-1,1,1,4,4,4-hexafluorobut-2-ene has a zero ozone depletion potential (ODP), low global warming potential (GWP) and non-flammable properties, so it is believed to be a potential foam expansion agent. For the synthetic process of cis-1,1,1,4,4,4-hexafluorobut-2-ene, the process catalysts are the key factors for its yield and cost. In this paper, the catalysts of palladium attached to porous aluminum fluoride, to active carbon, to Al2O3, and the blends of palladium and bismuth to AlF3 used to prepare cis-1,1,1,4,4,4-hexafluorobut-2-ene by cis-selective semi-hydrogenation of perfluoro-2-butyne were investigated. The performance of above-mentioned catalysts was compared in reaction process. The experimental results indicate that the additive of bismuth to palladium catalyst is useful for improving the activity and selectivity compared to Pd/C and Pd/Al2O3. The role of bismuth in the synthetic process is discussed based on the experimental results and theory analysis.

PHOTOREACTIONS OF TETRAFLUORODIPHOSPHINE WITH ALKYNES

The reaction of tetrafluorodiphosphine with several alkynes in the gas phase and under UV irradiation were studied.Simple addition products were obtained in substantial yield from CF3CCH, CF3CCCH3 and CF3CCCF3.Methyl substituted alkynes gave little volatile product while ethyne and diphenyl ethyne gave no volatile addition products.Non-volatile byproducts were obtained, probably polymers, in substantial quantity in the latter instances.Volatile products were characterized by IR and NMR spectra and by mass spectrometry.

Preparation method of 1, 1, 1, 4, 4, 4-hexafluoro-2-butyne

The invention discloses a preparation method of 1, 1, 1, 4, 4, 4-hexafluoro-2-butyne, which comprises the following steps: reacting hexachlorobutadiene with fluoride salt in a solvent, condensing, andcollecting the gas-phase reaction product to obtain the 1, 1, 1, 4, 4, 4-hexafluoro-2-butyne. The method has the advantages of being simple in process, high in yield, economical, environmentally friendly and easy to industrialize.

PROCESS TO PRODUCE (Z)-1,1,1,4,4,4-HEXAFLUORO-2-BUTENE AND INTERMEDIATES

A method of producing (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Z-1336mzz) is described. The method utilizes readily available halogenated starting materials, including 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) and carbon tetrachloride.

PROCESSES FOR PRODUCING Z-1,1,1,4,4,4-HEXAFLUOROBUT-2-ENE AND INTERMEDIATES FOR PRODUCING SAME

A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with hydrogen fluoride in the vapor phase in the presence of a fluorination catalyst comprising a metal halide to produce E- and Z-1,1,1,4,4,4-hexafluoro-2-chloro-2-butene. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene further comprises contacting E- and Z-1,1,1,4,4,4-hexafluoro-2-chloro-2-butene with base to produce 1,1,1,4,4,4-hexafluoro-2-butyne, and subsequently hydrogenating hexafluoro-2-butyne to produce Z-1,1,1,4,4,4-hexafluoro-2-butene.

Method for preparing 1,1,1,4,4,4-hexafluoro-2-butyne through gas phase method

The invention discloses a method for preparing 1,1,1,4,4,4-hexafluoro-2-butyne through a gas phase method, wherein hexafluoro-2-chloro-2-butene as a raw material is subjected to a gas phase dehydrochlorination reaction under the catalytic action of a dechlorination catalyst to obtain 1,1,1,4,4,4-hexafluoro-2-butyne. The method has the advantages of simple process, economy, environmental protectionand easy industrialization.

PROCESS FOR PRODUCING 1,1,1,4,4,4-HEXAFLUOROBUT-2-ENE

A process for producing E-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with hydrogen fluoride in the vapor phase in the presence of a fluorination catalyst. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene further comprises contacting E-1,1,1,4,4,4-hexafluoro-2-butene with chlorine in the presence of a catalyst to produce 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane, followed by reaction with base to produce 1,1,1,4,4,4-hexafluoro-2-butyne, and subsequently hydrogenating hexafluoro-2-butyne to produce Z-1,1,1,4,4,4-hexafluoro-2-butene.

Preparation method of trans-1, 1, 1, 4, 4, 4-hexafluoro-2-butene

The invention belongs to the field of organic fluorine chemical synthesis, and particularly relates to a preparation method of trans-1, 1, 1, 4, 4, 4-hexafluoro-2-butene. The invention discloses a preparation method of trans-1, 1, 1, 4, 4, 4-hexafluoro-2-butene, which comprises the following steps: by using trifluorotrichloroethane as a starting raw material, respectively carrying out reduction dimerization reaction and dechlorination reaction under the actions of hydrogen and metal zinc powder to obtain 2-hexafluorobutyne; and enabling 2-hexafluorobutyne to react with potassium ethyl xanthateor sodium ethyl xanthate, formic acid or water to obtain trans-1, 1, 1, 4, 4, 4-hexafluoro-2-butene. The invention discloses a preparation method of trans-1, 1, 1, 4, 4, 4-hexafluoro-2-butene, and can effectively solve the technical problem that an existing method for synthesizing trans-1, 1, 1, 4, 4, 4-hexafluoro-2-butene is harsh in condition and complex in reaction and needs severe high-temperature conditions, highly toxic reagents and expensive metal catalysts is solved.