692-50-2

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 
• 685-63-2 hexafluoro-1,3-butadiene 
• 78647-46-8 1,3,5,6,7-pentakis(trifluoromethyl)-2,4-diazabicyclo<3.2.0.>hepta-2,6-diene 
• 17157-69-6 (Z)-1,1,1,2,4,4,4-heptafluoro-but-2-ene 
• 87-68-3 Hexachlorobutadiene 
• 384-50-9 2,3-dibromo-1,1,1,4,4,4-hexafluoro-butane 
• 64-17-5 ethanol 
• 303-04-8 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene 
• 16005-62-2 bis-4,5-(trifluoromethyl)-1,3-dithiole-2-thione 
• 434-41-3 2-chloro-heptafluoro-2-butene 
• 680-17-1 1,1,1-trifluoro-2-fluoro-3,3-difluoro-4,4,4-trifluorobutane 
• 384-54-3 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane 
• 2418-22-6 cis-2,3-dichloro-1,1,1,4,4,4-hexafluorobutene-2 
• 7736-43-8 trans-2-chloro-1,1,1,4,4,4-hexafluorobutene-2 

Downstream Products

• 421-50-1 1,1,1-trifluoro-2-propanone 
• 368-51-4 acetic acid-(3,3,3-trifluoro-1-trifluoromethyl-propenyl ester) 
• 52649-59-9 5,6-Bis-trifluoromethyl-benzene-1,2,3,4-tetracarboxylic acid tetramethyl ester 
• 55523-20-1 10-phenyl-2,3-bis-trifluoromethyl-4H-1,4-etheno-benzo[b]phosphinine 
• 38308-65-5 Phenyl-(4,4,4-trifluoro-3-methoxy-2-trifluoromethyl-but-1-enylidene)-amine 
• 38308-69-9 p-Tolyl-(4,4,4-trifluoro-3-methoxy-2-trifluoromethyl-but-1-enylidene)-amine 
• 38308-67-7 (4-Methoxy-phenyl)-(4,4,4-trifluoro-3-methoxy-2-trifluoromethyl-but-1-enylidene)-amine 
• 38308-66-6 (E)-4,4,4-Trifluoro-N-(4-methoxy-phenyl)-2-trifluoromethyl-but-2-enimidic acid methyl ester 
• 38308-71-3 (E)-4,4,4-Trifluoro-N-(4-nitro-phenyl)-2-trifluoromethyl-but-2-enimidic acid methyl ester 
• 25575-38-6 (Z)-N-Cyclohexyl-4,4,4-trifluoro-2-trifluoromethyl-but-2-enimidic acid ethyl ester 
• 25575-39-7 Cyclohexyl-(3-ethoxy-4,4,4-trifluoro-2-trifluoromethyl-but-1-enylidene)-amine 
• 25611-87-4 N-Cyclohexyl-3-perfluormethyl-3-(1,2,3-tris-(perfluormethylcyclopropenyl)-ketenimin 
• 51088-97-2 2-((E)-3,3,3-Trifluoro-1-trifluoromethyl-propenyl)-cyclohexanone 
• 4648-63-9 trans-2-Dimethylarsino-1,1,1,4,4,4-hexafluor-but-2-en 

Relevant academic research and scientific papers

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.

MANUFACTURING METHOD OF PERFLUOROCYCLOALKENE COMPOUND

PROBLEM TO BE SOLVED: To obtain a perfluorocycloalkene compound high in conversion ratio of a reaction at high yield and high selectivity. SOLUTION: A perfluorocycloalkene compound represented by (1), where R1 to R4 are same or different, and represent a fluorine atom or a perfluoroalkadiene compound, is obtained by conducting a cyclization reaction of a perfluoroalkanediene compound represented by CR12=CR2-CR3=CR42, where R1 to R4 are same or different and represent a fluorine atom or a perfluoroalkyl group. The cyclization reaction can be conducted in presence of a catalyst, by a gas phase continuous flow type, or by the gas phase continuous flow type in presence of the catalyst. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

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.