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Oligomeric anion sulfonate surfactants, and preparation method and application thereof

An anionic sulfonate and surfactant technology, applied in the preparation of sulfonate, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of anhydrous protection, reduced yield, and high reaction risk.

Active Publication Date: 2018-05-01
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Although this synthetic method is feasible, there are still many deficiencies: (1) the solvent DMSO used in the first step of the reaction makes the aftertreatment difficult, and if the phase transfer catalyst is used instead, the yield will be reduced; (2) the active metal element in the second step The use of potassium makes the reaction very dangerous and requires anhydrous protection; (3) the reaction uses polyols as raw materials, and the diversity of molecular structures is limited

Method used

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  • Oligomeric anion sulfonate surfactants, and preparation method and application thereof
  • Oligomeric anion sulfonate surfactants, and preparation method and application thereof
  • Oligomeric anion sulfonate surfactants, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0072] Dipolyanion sulfonate DMEDA-(C 12 SO 3 Na) 2 Preparation of:

[0073]

[0074] (1) Synthesis steps of the intermediate product dimer alcohol: add 0.9g (10.0mmol) of N,N'-dimethylethylenediamine to 6.4g (30.0mmol) of 1,2-epoxytetradecane Ethanol (50ml) solution was reacted at 90°C for 24h. After the reaction, use a rotary evaporator to remove the absolute ethanol solvent, dissolve the crude product in chloroform, and then pass through a silica gel chromatography column with chloroform / methanol for purification and vacuum drying to obtain the intermediate dimer alcohol.

[0075] The intermediate dimer alcohol was characterized by MALDI-TOF: 513.5 (M+H).

[0076] (2) Dipolyanionic sulfonate surfactant DMEDA-(C 12 SO 3 Na) 2 The synthesis steps of the method: take 0.3g (60%, 7.5mmol) of sodium hydride, 1.0g (8.2mmol) of 1,3-propane sultone, and 0.5g (1.0mmol) of the intermediate dimer alcohol, dissolve them in THF, and reflux 48h, then add methanol to end the rea...

Embodiment 2

[0079] Tetrapolyanionic sulfonate surfactant EDA-(C 12 SO 3 Na) 4 Preparation of:

[0080]

[0081] (1) Synthetic steps of the intermediate product tetramer alcohol: ethylenediamine 0.6g (10.0mmol) is added to 1,2-epoxytetradecane 12.7g (60.0mmol) in dehydrated ethanol (50ml) solution at 90 Reaction at ℃ for 24h. After the reaction, the absolute ethanol solvent was removed with a rotary evaporator, and the crude product was dissolved in chloroform, then eluted with chloroform / methanol through a silica gel chromatography column, refined and vacuum-dried to obtain white powdery intermediate IV Polyol, 99% yield.

[0082] MALDI-TOF characterizes the intermediate tetramer: 910.1 (M+H).

[0083] (2) Tetrapolyanionic sulfonate surfactant EDA-(C 12 SO 3 Na) 4 The synthesis steps of the method: take 0.6g (60%, 15.0mmol) of sodium hydride, 2.0g (16.4mmol) of 1,3-propane sultone, and 0.9g (1.0mmol) of the intermediate tetramer alcohol, dissolve them in THF, and reflux 48h, t...

Embodiment 3

[0086] Hexameric anionic sulfonate surfactant TAEA-(C 12 SO 3 Na) 6 Preparation of:

[0087]

[0088] (1) Synthetic steps of the intermediate product hexamerol: the dehydrated alcohol ( 50ml) solution at 90°C for 24h. After the reaction, use a rotary evaporator to remove the absolute ethanol solvent, dissolve the crude product in chloroform, and then pass through a silica gel chromatography column with chloroform / methanol for purification and vacuum drying to obtain the intermediate hexamerol.

[0089] The intermediate hexamer alcohol was characterized by MALDI-TOF: 1420.6 (M+H).

[0090] (2) Hexameric anionic sulfonate surfactant TAEA-(C 12 SO 3 Na) 6 The synthesis steps of the method: take 1.0g (60%, 25mmol) of sodium hydride, 2.9g (23.7mmol) of 1,3-propane sultone, and 1.4g (1.0mmol) of the intermediate hexamerol, dissolve them in THF, and reflux for 48h , and then methanol was added to terminate the reaction. The solvent was removed by rotary evaporation, and t...

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PUM

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Abstract

The invention provides oligomeric anion sulfonate surfactants, and a preparation method and application thereof. Oligomeric anion sulfonate has a structure as shown in formulas I-V which are describedin the specification. According to the invention, 1,2-epoxyalkane and 1,3-propanesultone are used as raw materials and subjected to ring-opening reaction and sulfonation reaction so as to prepare a series of the oligomeric anion sulfonate surfactants with different oligomerization degrees, different alkyl chain lengths and different spacer group structures. The prepared oligomeric anion sulfonatesurfactants have good surface activity and aggregation behavior. The preparation method is simple in process, mild in reaction conditions, short in reaction period, simple in post-treatment and easyfor industrial production.

Description

technical field [0001] The invention belongs to the field of surfactant science and application, and in particular relates to an oligomeric anionic sulfonate surfactant, its preparation method and application. Background technique [0002] Traditional surfactants are amphiphilic molecules composed of a hydrophilic head group and a hydrophobic tail chain, and have been widely used in daily chemical, food, oil fields and other fields. On this basis, two or more amphiphilic units are connected by chemical bonds through linking groups on or near the head group to obtain dimerization (commonly known as Gemini surfactants). ), trimeric, tetrameric, and even higher oligomerized oligomeric surfactants. Gemini surfactants have many characteristics superior to traditional single-chain surfactants, such as lower critical micelle concentration (CMC), higher surface activity, lower Krafft point, excellent rheological properties, novel and diverse Aggregate structure and better wetting ...

Claims

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Application Information

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IPC IPC(8): C07C303/32C07C309/10B01F17/04C09K23/04
CPCC07C213/04C07C303/32C07C309/10C09K23/00
Inventor 王毅琳乔富林范雅珣
Owner INST OF CHEM CHINESE ACAD OF SCI
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