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Easy-to-separate degradable carboxylic acid sodium salt surfactant and its preparation and properties

A technology of surfactant and sodium carboxylate, applied in the field of easily separable degradable surfactants, can solve problems such as unreported degradation performance, achieve small surface tension and critical micelle concentration, high yield, eliminate foam and emulsification effect

Inactive Publication Date: 2015-11-25
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] At present, there are few literature reports on cyclic acetal-type surfactants, and most of them are five-membered ring acetal-type surfactants formed by condensation of aldehydes and 1,2-diols. The six-membered ring acetal type surfactant except that this research group has done part of the work, only finds very few literature reports, such as people such as SawomirKarczewski (see Sawomir, K.; Andrzej, P.; Irena, M.; J.SurfactDeterg,, 2008,201) use 2,2-dimethylol malonate diethyl ester and three kinds of aldehydes (octyl aldehyde, capric acid and dodecanal) to condense, then with 3-(N ’ ,N ’ -Dimethyl)-propylenediamine reacts to synthesize bisamides, and then oxidizes with hydrogen peroxide to obtain double-headed (hydrophilic) surfactants. This document only studies their synthesis, surface tension, cmc and foaming properties , but its degradation performance has not been reported

Method used

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  • Easy-to-separate degradable carboxylic acid sodium salt surfactant and its preparation and properties
  • Easy-to-separate degradable carboxylic acid sodium salt surfactant and its preparation and properties
  • Easy-to-separate degradable carboxylic acid sodium salt surfactant and its preparation and properties

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preparation example Construction

[0022] The preparation method of tensio-active agent provided by the present invention may further comprise the steps:

[0023] ①Using p-toluenesulfonic acid as a catalyst, cyclohexane as a water-carrying agent, adding a certain amount of N,N-dimethylformamide, 2,2-dimethylolpropionic acid and aliphatic aldehyde to react to prepare 5 -Methyl-2-alkyl-1,3-dioxane-5-carboxylic acid ( 2 ).

[0024] ② take 5-methyl-2-alkyl-1,3-dioxane-5-carboxylic acid ( 2 ) and sodium hydroxide were dissolved in anhydrous methanol and stirred, heated to reflux for eight hours, the solvent was distilled off, the residual solid was recrystallized with isopropanol, filtered with suction, washed with acetone and a small amount of water to obtain the pure product (3). Among them, 5-methyl-2-alkyl-1,3-dioxane-5-carboxylic acid ( 2 ) to sodium hydroxide in a molar ratio of 1:1.01.

[0025] The present invention will be further described below in conjunction with example:

Embodiment 1

[0026] Example 1: Preparation of 5-methyl-2-butyl-1,3-dioxane-5-carboxylic acid sodium salt ( 3a )

[0027] (1) Preparation of 5-methyl-2-butyl-1,3-dioxane-5-carboxylic acid ( 2a ):

[0028] Add 5.1034g (38.0766mmol) 2,2-dimethylol propionic acid, 3.6083g (41.8936mmol) n-valeraldehyde (distilled under reduced pressure before use), 0.1162g (0.6748mmol) p-formaldehyde in a 50ml round bottom flask successively Base benzenesulfonic acid, 10ml N,N-dimethylformamide, 10ml cyclohexane, install a magnetic stirrer, a water separator and a reflux condenser, heat the oil bath to reflux, and wait until no obvious water drops are formed in the water separator , stop heating, cooling; Add slightly excess sodium bicarbonate 0.0575g (0.6844mmol) (n 对甲基苯磺酸 :n 碳酸氢钠 =1:1.01) Stir at room temperature for half an hour (the purpose is to neutralize the catalyst p-toluenesulfonic acid), then distill off the solvent and water-carrying agent under reduced pressure, cool to obtain a solid, add cycl...

Embodiment 2

[0037] Example two: Preparation of 5-methyl-2-pentyl-1,3-dioxane-5-carboxylic acid sodium salt ( 3b ):

[0038] (1) Preparation of 5-methyl-2-pentyl-1,3-dioxane-5-carboxylic acid ( 2b ):

[0039] according to 2a prepared in the same way as 2b , to obtain the product 5.7g (26.4mmol), the yield was 64.0%.

[0040] Melting point: 135.3°C. Elemental analysis: C, 61.03; H, 9.24.

[0041] 1 HNMR (CDCl 3 ,400MHz)δ(ppm):4.514-4.539(1H,t,J=4.8,J=10.0,O- CH -O);4.444-4.472(2H,d,J=11.2,O- CH 2 -C);3.493-3.521(2H,d,J=11.2,O- CH 2 -C);1.639-1.690(2H,m,CH- CH 2 -CH 2 );1.378-1.430(2H,m,CH 2 - CH 2 -CH 3 ;1.309-1.316[4H,s,CH 2 - (CH 2 ) 2 -CH 2 ];1.055(3H,s,C- CH 3 ) ;0.890-0.923 (3H,t, CH 3 -CH 2 ).

[0042]IR(KBr)ν: 2950.7, 2924.0, 2858.8, 2653.2, 1691.8, 1461.2, 1406.5, 1327.0, 1256.7, 1161.8, 1127.5, 1070.4, 1020.4, 946.8, 915.0, 805.1, 722.9, 678.0 cm -1 . The above data prove that the target compound was successfully prepared.

[0043] (2) Prep...

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Abstract

The invention discloses an easily separated degradable sodium carboxylate surfactant and preparation and performance thereof. The invention discloses an easily separated degradable sodium carboxylate surfactant containing 1,3-dioxane. The surfactant is specifically 5-methyl-2-alkyl-1,3-dioxane-5-carboxylate and has the structural formula shown in the description, wherein a, R=C4H9; b, R=C5H11; c, R=C6H13; d, R=C7H15; e, R=C9H19; f, R=C10H21; and g, R=C11H23. The surfactant is convenient in synthesis, high in yield, small in surface tension and critical micelle concentration and wide in application temperature, serves as an emulsifying agent in an emulsion polymerization solution and is better than the traditional surfactant; and the surfactant is stable under neutral and alkaline conditions, can become sold to be separated out under the alkaline conditions, the separated solid is treated to become the original material which can be recycled, the unexpected foam and emulsification phenomena can be eliminated after the product action is exerted, and the surfactant is a novel environment-friendly product.

Description

technical field [0001] The invention relates to easily separated and degradable surfactants, in particular to 5-methyl-2-alkyl-1,3-dioxane-5-carboxylic acid sodium salt surfactants and their preparation and properties. Background technique [0002] Surfactants are widely used in many fields such as daily chemicals, food, textiles, medicine and petroleum. In 2011, the global consumption of surfactants reached 16 million tons. It is estimated that by 2015, the demand for global surfactants (excluding soap class) will reach 20 million tons. These surfactants are discharged into the water and ground environment after use, which not only directly leads to serious soil and water pollution, but also inhibits the degradation of other toxic substances, and even brings harm to the human body. Therefore, the separation or degradation performance of surfactants has attracted more and more attention. [0003] On the basis of its own structure, the surfactant introduces functional group...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01F17/32C07D319/06C09K23/32
Inventor 袁先友贾国凯袁霖张敏
Owner HUNAN UNIV OF SCI & ENG