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Polyfluoroalkyl alcohol or (meth)acrylic acid derivative thereof, and their production methods

The technology of a polyfluoroalkanol and a manufacturing method is applied in the preparation of hydroxyl compounds, the preparation of organic compounds, the preparation of carboxylic acid esters, etc., and can solve the problems of difficulty in manufacture or use, low bioaccumulation of compounds, and high bioaccumulation, Achieve the effect of less hindering the environment and easy decomposition

Active Publication Date: 2009-04-01
UNIMATEC CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Moreover, it has been reported in recent years that compounds having a polyfluoroalkyl group having an internal carbon number of about 8 in these compounds have high bioaccumulation and are environmentally problematic, and there is a concern that their production or use will become difficult in the future.
However, it is said that compounds with a polyfluoroalkyl group having 6 or less carbon atoms have low bioaccumulation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0041] Perfluorobutyl iodide C 4 f 9 I (purity 82.9%) 500g is packed in the autoclave of capacity 1200ml, when raising its internal temperature to reach about 50 ℃, add and dissolve in C 4 f 9 160g of two (4-tert-butylcyclohexyl) peroxycarbonate initiator (chemical medicine Aku ゾ product バ-カドツツッツクス 16) 0.75g, when the internal temperature reaches 55 ℃, while maintaining the pressure of 0.5~0.7MPa, add in batches After the vinylidene fluoride reaches 214 g, it is aged at a temperature of 55-65° C. for 1 hour to end the reaction. After the reaction was finished, it was cooled, and 583 g of the product was recovered.

[0042] In addition, the resulting product was separated by distillation under the conditions of a tower top temperature of 58°C and a pressure of 7.4kPa (56mmHg) to obtain CF 3 (CF 2 ) 3 (CH 2 CF 2 ) I (purity 99.5%) 203g. This was used as the reaction raw material of Reference Examples 2 and 3. It should be noted that for the reaction product CF 3 (CF ...

reference example 2

[0044] Will CF 3 (CF 2 ) 3 (CH 2 CF 2 )I (purity 99.5%) 600g is packed in the autoclave of capacity 1200ml, when raising its internal temperature to reach about 50 ℃, add and dissolve in CF 3 (CF 2 ) 3 (CH 2 CF 2 ) 1.35g of the peroxide initiator (ba-kadux 16) of I300g, when the internal temperature reaches 55°C, while maintaining the pressure of 0.2~0.3MPa, add tetrafluoroethylene in batches, after adding 150g in batches, Aging at 55-74°C for 1 hour to end the reaction. After the reaction was finished, it was cooled, and 1010 g of the product was recovered.

[0045] In addition, the resulting product was separated by distillation under the conditions of a tower top temperature of 71°C and a pressure of 2.6kPa (20mmHg), to obtain CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) I (purity 99.8%) 347g. This was used as the reaction raw material of Reference Example 3.

reference example 3

[0047] Will CF 3 (CF 2 ) 3 (CH 2 CF 2 )I (purity 99.5%) and CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) I (purity 99.8%) mixture (weight ratio 35.4:64.0) 830g was put into an autoclave with a capacity of 1200ml, and when the internal temperature was raised to about 50°C, 300g of a peroxide system dissolved in the mixture of the mixed composition was added. Initiator (Vacadox 16) 1.68g, when the internal temperature reaches 55°C, while maintaining a pressure of 0.2-0.3MPa, add tetrafluoroethylene in batches, add 150g in batches, and age at 55-78°C for 1 hours to end the reaction. Cooling was carried out after completion of the reaction, and 1257 g of mixed products were recovered.

[0048] In addition, for the obtained product, separation was carried out by distillation to obtain CF 3 (CF 2 ) 3 (CH 2 CF 2 ) I (purity 99.7%) 184g, CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) I (purity 99.4%) 575g and CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) 2 I (purity 99.3...

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Abstract

Disclosed is a polyfluoroalkyl alcohol represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOR (R: H, a (meth)acrylic acid group; n:1-6; a:1-4; b:1-3; c:1-3), or a (meth)acrylic acid derivative thereof. A polyfluoroalkyl alcohol (R: a hydrogen atom) can be produced by reacting a fluoroalkyl iodide represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cI with N-methylformamide, and then hydrolyzing the resulting in the presence of an acid catalyst. A (meth)acrylic acid derivative of such a polyfluoroalkyl alcohol (R: a (meth)acrylic acid group) can be produced by reacting a (meth)acrylic acid with the polyfluoroalkyl alcohol.

Description

technical field [0001] The present invention relates to polyfluoroalkanol or its (meth)acrylic acid derivative and their production method. More specifically, it relates to a polyfluoroalkanol or a (meth)acrylic acid derivative thereof which is effectively used as a surfactant, a hydrophobic and oleophobic agent raw material monomer, and a method for producing the same. Background technique [0002] Acrylic acid derivatives of polyfluoroalkanols, such as CF 3 (CF 2 ) 7 CH 2 CH 2 OCOCH=CH 2 It is widely used as a synthetic monomer for hydrophobic and oil-repellent agents for fibers. In addition, polyfluoroalkanol, which is an acrylated precursor thereof, is widely used as a surfactant and the like. [0003] Patent Document 1: Japanese Patent Publication No. 63-22237 [0004] Furthermore, it has been reported in recent years that compounds having a polyfluoroalkyl group having an internal carbon number of about 8 in these compounds have high bioaccumulation and are env...

Claims

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Application Information

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IPC IPC(8): C07C31/38C07C29/124C07C67/08C07C69/653C07B61/00
CPCC07C31/38C07C29/09C07C29/124C07C67/08C07C19/16C07C69/653C07C17/275
Inventor 村田清一郎堀内雅可佐藤胜之阿部秀辉达春美
Owner UNIMATEC CO LTD
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