27905-45-9

Basic information

• Product Name: 1H,1H,2H,2H-Heptadecafluorodecyl acrylate
• Synonyms: TETRAHYDROPERFLUORODECYL ACRYLATE;1,1,2,2-Tetrahydroperfluorodecylacrylate;2-propenoicacid,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylest;2-Propenoicacid,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylester;ACRYLIC ACID 1H,1H,2H,2H-HEPTADECAFLUORO-N-DECYL ESTER;ACRYLIC ACID 1H,1H,2H,2H-PERFLUORODECYL ESTER;1H,1H,2H,2H-PERFLUORODECYL ACRYLATE;1H,1H,2H,2H-HEPTADECAFLUORO-N-DECYL ACRYLATE
• CAS NO: 27905-45-9
• Molecular Formula: C₁₃H₇F₁₇O₂
• Molecular Weight: 518.17
• EINECS: 248-722-7
• Product Categories: monomer;Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry
• Mol File: 27905-45-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: -3°C
• Boiling Point: 90 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid
• Density: 1.637 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.337(lit.)
• Storage Temp.: 0-6°C
• Solubility: Chloroform, Methanol (Slightly), Water (Sparingly)
• Stability: Light Sensitive
• BRN: 5173337
• CAS DataBase Reference: 1H,1H,2H,2H-Heptadecafluorodecyl acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H,2H,2H-Heptadecafluorodecyl acrylate(27905-45-9)
• EPA Substance Registry System: 1H,1H,2H,2H-Heptadecafluorodecyl acrylate(27905-45-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• WGK Germany: 3
• F: 10-23
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 27905-45-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

(Perfluorooctyl)ethyl Acrylate is a reagent used in the synthesis of parahydrophobic polymer coatings, as well as polymer brushes for controlling surface lubrication.

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

• 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 
• 2043-53-0 2-(n-perfluorooctyl)ethyl iodide 
• 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 
• 5651-26-3 acrylic acid silver salt 
• 116-14-3 polytetrafluoroethylene 
• 74-85-1 ethene 

Relevant articles and documents

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 (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 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.