27905-45-9

Usage

Uses

Used in Parahydrophobic Polymer Coatings:
1H,1H,2H,2H-Heptadecafluorodecyl acrylate is used as a reagent for the synthesis of parahydrophobic polymer coatings. Its application is due to its ability to provide water-repellent properties to the coatings, making them suitable for various surfaces that require protection against water and moisture.
Used in Polymer Brushes for Surface Lubrication:
1H,1H,2H,2H-Heptadecafluorodecyl acrylate is also used as a reagent in the synthesis of polymer brushes designed for controlling surface lubrication. The compound's perfluorinated nature contributes to the low friction and reduced wear properties of the brushes, making them ideal for applications where reduced friction and enhanced lubrication are desired.

InChI:InChI=1/C13H7F17O2/c1-2-6(15,16)8(19,20)10(23,24)12(27,28)13(29,30)11(25,26)9(21,22)7(17,18)4(14)3-5(31)32/h3H,2H2,1H3,(H,31,32)/b4-3-

Synthetic route

Conditions	Yield
With 4-methoxy-phenol; hydroquinone In tert-butyl alcohol at 180℃; for 6h; Conversion of starting material;	99%

Conditions	Yield
With 4-methoxy-phenol; hydroquinone In tert-butyl alcohol at 180℃; for 6h;	12%

2-(perfluorodecyl)ethanol + 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol (678-39-7) + acrylic acid (79-10-7) → 1H,1H,2H,2H-heptadecafluorodecyl acrylate (27905-45-9)

Conditions	Yield
With hydroquinone; toluene-4-sulfonic acid In toluene for 4h; Product distribution / selectivity;

Upstream product

• 2043-53-0 2-(n-perfluorooctyl)ethyl iodide 
• 10192-85-5 potassium acrylate 
• 133299-39-5 C₁₀H₄F₁₇Cl 
• 865-86-1 2-(perfluorodecyl)ethanol 
• 678-39-7 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol 
• 79-10-7 acrylic acid 
• 60699-51-6 1H,1H,2H,2H-perfluorohexadecan-1-ol 
• 65104-67-8 1H,1H,2H,2H-perfluorooctadecan-1-ol 
• 39239-77-5 1H,1H,2H,2H-perfluorobutadecan-1-ol 
• 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 
• 5651-26-3 acrylic acid silver salt 
• 116-14-3 polytetrafluoroethylene 

Relevant academic research and scientific papers

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 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.

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 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 FLUOROALKYL IODIDE

The present invention provides a process for producing a fluoroalkyl iodide represented by the general formula (II):Rf-CH2CH2I wherein Rf is a perfluoroalkyl or polyfluoroalkyl group comprising 1 to 20 carbons, the process comprising reacting hydrogen iodide gas with a fluoroalkene in the presence of a catalyst. The present invention also provides a process for producing a fluoroester by reacting the fluoroalkyl iodide with a carboxylate.