ChemicalBook CAS DataBase List 2-(Perfluorohexyl)ethyl methacrylate

2-(Perfluorohexyl)ethyl methacrylate synthesis

8synthesis methods

Product Name:2-(Perfluorohexyl)ethyl methacrylate
CAS Number:2144-53-8
Molecular formula:C12H9F13O2
Molecular Weight:432.18

2-(Perfluorohexyl)ethyl methacrylate is an important intermediate in the production of surface protective agents, widely used in the fields of textiles, coatings and fluorosurfactants. It can be synthesized by condensation reaction of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-ol and 2-methyl-2-propenic acid.

79-41-4 Synthesis

79-41-4
501 suppliers
$14.00/5g

647-42-7 Synthesis

647-42-7
262 suppliers
$10.00/10g

2144-53-8
237 suppliers
$6.00/5g

Yield:2144-53-8 94%

Reaction Conditions:

with hydroquinone;toluene-4-sulfonic acid in toluene at 115; for 5 h;

Steps:

1 Synthesis of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane 2-methyl-2-properiic acid ester

Toluene (2 L), 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-ol (2.18 kg, 6.0 mol), 2-methyl-2-propenic acid (methacrylic acid) (567 g, 6.6 mol) and 1,4-dihydroxybenzene (hydroquinone) (6.59 g, 60 mmol) were added and then p-toluenesulfonic acid monohydrate (148.06 g, 0.78 mol) was added thereto. The obtained solution was heated and subjected to reflux dehydration at 115° C. for 5 hours. After reflux dehydration, the obtained reaction solution was cooled to around room temperature and added with triethylamine (151.5 g, 1.50 mol) was added thereto, stirred for 0.5 hours and then added with 150 g of silica gel. After stirring for 0.5 hours, the silica gel was filtered off and the obtained filtrate was added with 1,4-dihydroxybenzene (hydroquinone) (1.32 g, 12.0 mmol), and the solvent was removed in vacuum distillation and then was purified in distillation to obtain 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane 2-methyl-2-propenic acid ester (2.44 kg, 94%).

References:

US2010/324314,2010,A1 Location in patent:Page/Page column 15

2043-57-4 Synthesis