1623-05-8

Basic information

• Product Name: Heptafluoropropyl trifluorovinyl ether
• Synonyms: 1,1,1,2,2,3,3-heptafluoro-3-[(trifluoroethenyl)oxy]-propan;1,1,1,2,2,3,3-Heptafluoro-3-[(trifluoroethenyl)-oxy]propane;1,1,1,2,2,3,3-heptafluoro-3-[(trifluoroethenyl)oxy]-Propane;1,1,1,2,2,3,3-Heptafluoro-3-[trifluoroethenyl-oxy]propane;1,1,1,2,2,3,3-Heptafluoro-3-trifluorovinyloxy-propane;Propane,1,1,1,2,2,3,3-heptafluoro-3-[(trifluoroethenyl)oxy]-;HEPTAFLUOROPROPYL TRIFLUOROVINYL ETHER;PERFLUORO(PROPYL VINYL ETHER)
• CAS NO: 1623-05-8
• Molecular Formula: C₅F₁₀O
• Molecular Weight: 266.04
• EINECS: 216-600-2
• Product Categories: Fluoromonomer
• Mol File: 1623-05-8.mol

Chemical Properties

• Melting Point: -70 °C
• Boiling Point: 35 °C
• Flash Point: -20°C
• Appearance: Colorless
• Density: 1,53 g/cm3
• Vapor Pressure: 289mmHg at 25°C
• Refractive Index: 1.272
• Water Solubility: Insoluble in water
• CAS DataBase Reference: Heptafluoropropyl trifluorovinyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Heptafluoropropyl trifluorovinyl ether(1623-05-8)
• EPA Substance Registry System: Heptafluoropropyl trifluorovinyl ether(1623-05-8)

Safety Data

• Hazard Codes: F
• Statements: 12
• Safety Statements: 9-16-33
• RIDADR: 3271
• HazardClass: FLAMMABLE
• Hazardous Substances Data: 1623-05-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 4332, 1994 DOI: 10.1021/jo00094a058

InChI:InChI=1/C5F10O/c6-1(7)2(8)16-5(14,15)3(9,10)4(11,12)13

Upstream product

• 2062-98-8 perfluoro(2-propoxypropionyl) fluoride 
• 591-51-5 phenyllithium 
• 79630-80-1 Sodium; 2,2,3,3-tetrafluoro-3-heptafluoropropyloxy-propionate 
• 106372-30-9 perfluoropropyl 1,2-Dichlorotrifluoroethyl Ether 
• 428-59-1 Hexafluoropropene oxide 
• 111-96-6 diethylene glycol dimethyl ether 
• 67963-75-1 sodium 2,3,3,3-tetrafluoro-2-(perfluoropropoxy)propanoate 
• 156731-86-1 1,1-Dihydropentafluoropropyl 1,2-dichlorotrifluoroethyl ether 
• 1682-32-2 1,1-Dihydropentafluoropropyl trifluorovinyl ether 
• 871504-55-1 C₇O₃F₁₂ 
• 296758-59-3 CF₃CF₂CF₂OCF(CF₃)CF₂OCOCF(CF₃)OCF₂CF₂CF₃ 
• 116-15-4 perfluoropropylene 
• 1479-49-8 bis(trifluoromethyl) ether 
• 1187-93-5 trifluoromethyl trifluorovinyl ether 

Downstream Products

• 144373-65-9 3-(Perfluoro-2-hydro-3-oxahexyloxy)nitrobenzene 
• 144373-66-0 C₂₂H₁₀F₂₀O₆S 
• 144373-62-6 (2-Chloro-1,1,2-trifluoro-2-heptafluoropropyloxy-ethoxy)-benzene 
• 95472-47-2 1-phenoxy-2-bromo-3-oxaperfluorohexane 
• 144385-03-5 3-(perfluoro-2-chloro-3-oxahexyloxy)nitrobenzene 
• 375-62-2 Perfluoro pentanoyl fluoride 
• 107432-46-2 Perfluoro(1-propoxyethyl) iodide 
• 20488-54-4 trans-1,2-difluoro-1,2-diphenylethylene 
• 337-33-7 1,1-diphenyl-2,2,3,3,3-pentafluoropropan-1-ol 
• 854992-65-7 C₁₇H₁₀F₈O 
• 95454-42-5 1-phenoxy-2-monohydro-3-oxaperfluorohexane 
• 1691-13-0 1,2-difluoroethene 
• 754-34-7 1,1,1,2,2,3,3-heptafluoro-3-iodo-propane 
• 91095-98-6 2,2,3,3-Tetrafluoro-3-iodo-propionyl fluoride 

Relevant articles and documents

The unusual reactivity of C F OCF CF with PBu and the complex hydrides M[EH] (M: Li, Na; E: B, Al); preparation of potassium perfluoro-2-propoxyeth-1-enyltrifluoroborate K[C F OCF CFBF]

The nucleophilic hydrodefluorination of C3F7 OCF=CF2 with the complex hydrides Li[AlH4], Li[BH4] or Na[BH4] proceeded non-stereoselectively and was accompanied by the formation of either cis- and trans-C3F7OCH=CFH and/or C3F7 OCHFCF2H. The reaction of C3F7 OCF=CF2 with PBu3 followed by treatment with BF3·OMe2 or BF3· OEt2 yielded [C3F7OCF=CFPBu3] [BF4] (cis and trans) and, probably, [trans -Bu3 PCF=CFPBu3] [BF4]2. The hydrolysis of the latter with pure water proceeded quickly while the former isomeric mixture formed the isomeric olefins C3F7OCF=CFH slowly. The usage of aqueous NaOH instead of water produced mainly trans -HF=CHF. The metallation of C3F7OCF=CFH (cis:trans=45:55) to C3F7OCF=CFLi and its subsequent reaction with B(OMe)3 and K[HF2] gave the salt K[C3F7OCF=CFBF3] in a different cis to trans ratio (25:75) with satisfactory yield.

Application of perfluoro(2-propoxypropyl vinyl ether) (PPVE-2) in the synthesis of perfluoro(propyl vinyl ether) (PPVE-1)

A novel preparative method for the conversion of n-C3F7OCF(CF3)CF2OCF = CF2 (PPVE-2) into n-C3F7OCF = CF2 (PPVE-1) is reported. It includes the catalytic oxidation of PPVE-2 with molecular oxygen to furnish a mixture of carbonyl fluorides which are subjected to alkaline hydrolysis resulting in a mixture of salts. Subsequent thermolysis of those salts give rise to an inseparable mixture of PPVE-1 and perfluoro-2-propoxypropanoyl fluoride. Treatment of this mixture with sodium carbonate allowed to obtain sodium perfluoro-2-propoxypropionate and to isolate PPVE-1. Thermolysis of this sodium salt produced an additional amount of PPVE-1, so that the total conversion of PPVE-2 into PPVE-1 is accomplished in good yields. The reaction conditions, the choice of reagent as well as the course of competitive reactions are discussed.

A fluorinated alkyl vinyl ether of preparation method

The invention discloses a fluoroalkylvinyl ether preparation method. The method comprises the following steps: carrying out a film forming reaction on perfluoroalkyloxypropionyl fluoride by a salt forming agent under the action of an aprotic alcohol ether catalyst at 20-80DEG C, and carrying out a decarboxylation reaction at 110-150DEG C to prepare corresponding fluoroalkylvinyl ether. The preparation method has the advantages of high raw material conversion rate, simple process, no need of a solvent, and the like.

Method for Preparing Fluorine-Containing Vinyl Ether

Provided is a method for preparing fluorine-containing vinyl ether. The method comprises: carrying out hydrolytic neutralization on a small molecular weight byproduct which is produced in the process of preparing perfluoropolyether or a perfluorinated surfactant by photooxidation of fluorine-containing olefin; and obtaining fluorine-containing vinyl ether by drying and cracking. The byproduct produced in the process of preparing perfluoropolyether or the perfluorinated surfactant is utilized, thereby solving the emission problem of industrial wastes, reducing environment pollution, and generating available fluorine-containing vinyl ether.

COMPOUND HAVING PERFLUORO(4-METHYLENE-1,3-DIOXOLANE) STRUCTURE AND NOVEL POLYMER

Disclosed are a compound having a perfluoro(4-methylene-1,3-dioxolane) structure which has not been known yet, and a novel polymer. Specifically disclosed are a compound represented by the formula (a) below which has a perfluoro(4-methylene-1,3-dioxolane) structure, a method for producing such a compound, a novel compound useful for producing such a compound, and a novel polymer containing a repeating unit represented by the formula (A) below. (In the formulae, RF1-RF4 independently represent a fluorine atom, a chlorine atom or a monovalent perfluorinated saturated organic group having 1-20 carbon atoms.)

PROCESSES FOR PRODUCING FLUORINATED ESTER, FLUORINATED ACYL FLUORIDE, AND FLUORINATED VINYL ETHER

A process for producing a fluorinated ester through a small number of steps, is presented. The process for producing a fluorinated ester, comprises a transesterification step in which RAF-COOCF2-RAF and RA-CH2OH are subjected to a transesterification reaction to obtain RAF-COOCH2-RA, and a fluorination step in which the obtained compound is fluorinated to obtain a reaction product containing RAF-COOCF2-RAF. Here, in the formulae, RA is a monovalent organic group, and RAF is the same group as RA or a monovalent organic group obtained by fluorination of RA.

Polyfluorinated ethers: IV.* By-products in the synthesis of polyfluorinated alkyl vinyl ethers in a solvating solvent

By-products formed in the synthesis of perfluoro(propyl vinyl ether), perfluoro(2-propoxypropyl vinyl ether), and methyl perfluoro(4-vinyloxybutanoate) in a solvating solvent have been studied. 1998 MAHK "Hayka/Interperiodica".

Radical additions to fluoro-olefins. Photochemical mono-fluoroalkylation and sequential bis-fluoroalkylation of oxolane

Oxolane was fluoroalkylated by its photoadditions under atmospheric pressure. Monofluoro-alkylations were carried out with hexafluoropropene (1) and perfluorovinyl ethers C3F7O-[CF(CF3)CF2O]n-CF=CF2 (2-4, n=0-2) by direct photoexcitation of the oleflns to give high yields of addition products 9-12 (81-94%). The reactions were completely regioselective at the oxolane molecule and almost completely regioselective (93-99%) at the double bond of fluoro-olefins; no bis-fluoroalkylated oxolanes were detected. The completely selective introduction of a second fluoroalkyl into position 5 of the oxolane molecule was accomplished by acetone-sensitised photoaddition of 2-fluoroalkylated oxolanes 9, 10 to fluoro-olefins 1 and 2. Byproducts from reactions of the dimethylketyl radical which is formed in the initiation step were isolated and have given some evidence about the reaction mechanism that is discussed.

Polyfluoroalkyl Polyfluorovinyl Ethers. I. Kinetics and Mechanism of Formation of Perfluoropropyl Perfluorovinyl Ether from Sodium Perfluoro-2-methyl-2-oxahexanoate

The kinetics and mechanism of decarboxylation of sodium perfluoro-2-methyl-3-oxahexanoate have been studied in aprotic (diethylene glycol dimethyl ether) and protic (ethylene glycol) solvents.In the synthesis of perfluoropropyl perfluorovinyl ether, the concurrent formation of 1,3,3,3-tetrafluoroethyl perfluoropropyl ether is thermodynamically more favorable.