678-39-7

Usage

Uses

Used in Coatings Industry:
1H,1H,2H,2H-Perfluoro-1-decanol is used as a component in the formation of a barrier and self-healing coating on zinc metal materials. This application takes advantage of its chemical properties to provide protection and self-repair capabilities to the coated surfaces.
Used in Pharmaceutical Research:
1H,1H,2H,2H-Perfluoro-1-decanol has been observed to induce cell death and the formation of oxidative or reactive oxygen species in cerebellar granule cells. This property may be utilized in the study of various pharmaceutical applications, particularly those related to cellular response and oxidative stress.
Used in Chemical Synthesis:

InChI:InChI=1/C8H2F12O4/c9-3(10,1(21)22)5(13,14)7(17,18)8(19,20)6(15,16)4(11,12)2(23)24/h(H,21,22)(H,23,24)

Upstream product

• 74-85-1 ethene 
• 77758-89-5 phenyl(perfluorooctyl)iodonium triflate 
• 2043-53-0 2-(n-perfluorooctyl)ethyl iodide 
• 117068-31-2 (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-n-decyl)trifluoroacetate 
• 65510-55-6 1-iodo-1H,1H,2H,2H-perfluorohexadecane 
• 2043-55-2 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide 
• 2043-57-4 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane 
• 2043-54-1 1-iodo-1H,1H,2H,2H-perfluorododecane 
• 30046-31-2 1-iodo-1H,1H,2H,2H-perfluorotetradecane 
• 10192-85-5 potassium acrylate 
• 79-10-7 acrylic acid 
• 5651-26-3 acrylic acid silver salt 
• 79-41-4 poly(methacrylic acid) 
• 64-19-7 acetic acid 

Downstream Products

• 1996-88-9 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl methacrylate 
• 27854-31-5 acide 2-perfluorooctylethanoieque 
• 201593-46-6 ethyl 4-<2-(perfluorooctyl)ethoxy>benzoate 
• 1829-26-1 1-acetoxy-1,2-benziodoxol-3-one 
• 135984-68-8 1H,1H,2H,2H-perfluoro-1-nonanal 
• 142502-68-9 (Z)-3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Hexadecafluoro-dec-2-enal 
• 145476-54-6 4-Butyl-benzoic acid 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl ester 
• 145476-56-8 3-Cyano-benzoic acid 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl ester 
• 145476-55-7 3-Nitro-benzoic acid 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl ester 
• 243645-12-7 tert-butyldiphenylsilyl 1H,1H,2H,2H-perfluorodecyl ether 
• 113823-56-6 toluene-4-sulfonic acid 1,1,2,2-tetrahydroperfluorodecyl ester 
• 171182-85-7 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Electrochemical Oxidation of Polyfluoroalkyl Iodides: Direct Anodic Transformation of C8F17CH2CH2I to Amides, Esters, and Ethers

The cyclic voltammetry of polyfluoroalkyl iodides of the type RfCH2CH2I (Rf = n-C6F13, n-C8F17, n-C10F21) and RfI (Rf = n-C4F9, n-C6F13,n-C8F17, n-C10F21) was investigated in nonaqueous media.All the iodides exhibited one distinctive oxidation peak, but only C8F17CH2CH2I was suitable for surveying preparative-scale electrosynthetic reactions because the other iodides either had poor solubility or caused severe filming of the anode.The direct anodic transformations of the iodide to the corresponding amides (C8F17CH2CH2NHCOR; R = CH3, CH=CH2, C(Me)=CH2), esters (C8F17CH2CH2OCOR; R = CH3, CF3, CH=CH2, C(Me)=CH2, C6H5), ethers (mainly C8F17CH2CH2OCH2CF3), and alcohol (C8F17CH2CH2OH) were observed and a general mechanistic scheme involving a hypervalent iodanyl radical intermediate is proposed.

Method for preparing perfluoroalkyl ethanol

The invention discloses a method for preparing perfluoroalkyl ethanol. The method comprises the following steps: enabling perfluoroalkyl ethyl iodide, a mixed solvent and water to react, and separating and purifying the obtained mixture containing perfluoroalkyl ethanol, by-product olefins, solvent salt and water, thereby obtaining the perfluoroalkyl ethanol product, wherein the separation and purification comprise the following steps: (1) adding a mixture containing perfluoroalkyl ethanol, by-product olefins, solvent salt and water into a rectifying tower for performing reduced pressure distillation, controlling the vacuum degree to be -0.91 to -0.96MPa so as to obtain distillate containing perfluoroalkyl ethanol, by-product olefins and water and bottom liquid, performing strong base treatment on the bottom liquid, and filtering to obtain the recycled mixed solvent; and (2) performing azeotropic distillation on the distillate, thereby obtaining the mixed solution of the by-product olefins and water and the product perfluoroalkyl ethanol. The method disclosed by the invention has the advantages of simplicity in process, greening, environment friendliness, convenience, high efficiency and low cost.

Method for preparing perfluoroalkyl alcohol from perfluoroalkyl ethylene

The invention discloses a method for preparing perfluoroalkyl alcohol from perfluoroalkyl ethylene.The method comprises the main steps that 1, a borane tetrahydrofuran solution is dropwise added into a dry three-opening bottle containing a perfluoroalkyl vinyl ether solution under the protection of nitrogen atmosphere; the mixture is stirred at the temperature of -20-25 DEG C, the reaction time is 8-24 h, after the reaction is finished, deionized water is added to decompose unreacted borane, and a reaction intermediate product is obtained; 2, inorganic strong base and a hydrogen peroxide aqueous solution are added into the reaction intermediate product, a reaction is performed for 0.5-3 h at the temperature of 0-50 DEG C, a solvent is removed after the reaction is finished, deionized water is used for washing, liquid separation is carried out, anhydrous magnesium sulfate is used for drying, and the perfluoroalkyl alcohol is prepared.The technological method is easy, the reaction can be performed under the normal pressure, the raw materials are rich and easy to obtain, the reaction efficiency is 100%, the yield is larger than 75%, and the method is suitable for industrial production.

Unprecedented iron-catalyzed ester hydrogenation. Mild, selective, and efficient hydrogenation of trifluoroacetic esters to alcohols catalyzed by an iron pincer complex

The synthetically important, environmentally benign hydrogenation of esters to alcohols has been accomplished in recent years only with precious-metal-based catalysts. Here we present the first iron-catalyzed hydrogenation of esters to the corresponding alcohols, proceeding selectively and efficiently in the presence of an iron pincer catalyst under remarkably mild conditions. The replacement of precious-metal catalysts by an iron complex was accomplished for the synthetically important, environmentally benign hydrogenation of esters to alcohols under mild conditions. The iron pincer complex (see scheme) selectively and efficiently catalyzes the hydrogenation of trifluoroacetates under remarkably mild conditions (5-25 bar and 40 °C).

Synthesis of 2-(perfluoroalkyl)ethyl potassium sulfates based on perfluorinated Grignard reagents

The first example of nucleophilic substitution with perfluoroalkyl Grignard reagents on the sp3 carbon centre is described. Thus, a series of organometals RF-MgBr, prepared from perfluorinated alkyl iodides RF-I with RF = C4F9, C 6F13, C8F17, C10F 21 and C12F25, reacted with 1,3,2-dioxathiolane-2,2-dioxide to afford the corresponding 2-(perfluoroalkyl) ethyl magnesium sulfates, which were isolated after metathesis to the corresponding potassium salts. In the model reaction, perfluorohexylmagnesium iodide was reacted with methyl triflate yielding polyfluorinated alkane. The attempts to extend the reaction to 1,3,2-dioxathiane-2,2-dioxide were unsuccessful due to its inferior reactivity and only reduced polyfluoroalkane and the product of coupling were detected in the reaction mixture. Polyfluorinated sulfates are easily hydrolyzed with hydrochloric or triflic acid to the corresponding alcohols, which is an alternative to standard transformation of perfluoroalkyl iodides to 2-(perfluoroalkyl)ethanols. Quantum-chemical calculations of the PES of the reaction with both sulfur-containing heterocycles found that the failure of the reaction with 1,3,2-dioxathiane-2,2-dioxide is caused by higher activation energy of the process.

PROCESS FOR PRODUCING FLUORINATED (METH)ACRYLIC ESTER

A mixture of fluoroalkyl iodides of the formula C2F5(CF2CF2)nI ( n is an integer of ≥0) wherein the sum of such fluoroalkyl iodides of n=3 and n=4 contained is ≥85 mol% is provided. This mixture is subjected to an ethylene addition step and an esterification step, and C2F5(CF2CF2)nCH=CH2 and C2F5(CF2CF2)nCH2CH2OH are removed. Thus, there can be obtained a mixture of fluorine-containing (meth)acrylic esters of the formula C2F5(CF2CF2)nCH2CH2OCOCR1=CH2 (wherein R1 represents a hydrogen atom or a methyl group, and n is an integer of ≥0) wherein the content of impurities (namely, olefins of the formula C2F5(CF2CF2)nCH=CH2 and alcohols of the formula C2F5(CF2CF2)nCH2CH2OH) is low.

PROCESS FOR PRODUCING FLUORINATED ACRYLIC ESTER

A mixture of fluorine-containing acrylic esters represented by CF3(CF2)nCH2CH2OCOCR1=CH2 wherein R1 is a hydrogen atom, a methyl group or a halogen atom and "n" is an integer of at least zero is subjected to distillation under such conditions that the esters are not polymerized, so as to give a mixture of the esters with a less content of impurities (that is, olefins represented by CF3(CF2)nCH=CH2 and alcohols represented by CF3(CF2)nCH2CH2OH) at a high yield.

PROCESS FOR PRODUCING FLUORINATED ACRYLIC ESTER

A mixture of fluoroalkyl alcohols represented by C 2 F 5 (CF 2 CF 2 ) n CH 2 CH 2 OH wherein "n" is an integer equal to or more than 0 wherein the sum of the fluoroalkyl alcohols of n=3 and n=4 contained is 85 mol% or more is prepared and reacted with an acrylic acid compound followed by removing unreacted C 2 F 5 (CF 2 CF 2 ) n CH 2 CH 2 OH, to give a mixture of fluorine-containing acrylic esters wherein the content of impurities (that is, olefins represented by C 2 F 5 (CF 2 CF 2 ) n CH=CH 2 and the alcohols represented by C 2 F 5 (CF 2 CF 2 ) n CH 2 CH 2 OH) is low.

Process for preparing fluorinated alkyl carboxylate esters

A process for preparing fluorinated alkyl carboxylate esters comprises reaction of a silver carboxylate or silver carboxylate precursor, such as silver (I) iodide with a fluorinated alkyl iodide and a carboxylic acid. Preferably the fluorinated alkyl iodide has the general formula CF3(CF2)nCH2CH2I, wherein n is an integer in the range of from 1 to 29 and the carboxylic acid is acetic acid, acrylic acid or methacrylic acid.

Purification of fluorinated alcohols

A process for reducing the level of perfluoroalkanoic acids, perfluoroalkanoic esters, and perfluoroalkyliodides in fluorinated alcohols comprising heating a fluorinated alcohol, or mixtures thereof, containing said acids, esters, or iodides to a temperature of at least 175° C. in the presence of water and a base additive is disclosed.