CN107955045B - Alkyl glycoside alkyl succinic acid monoester sulfonate surfactant and preparation method thereof - Google Patents
Alkyl glycoside alkyl succinic acid monoester sulfonate surfactant and preparation method thereof Download PDFInfo
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Abstract
Description
Technical Field
The invention belongs to the field of surfactant synthesis, and particularly relates to an alkyl glycoside alkyl succinic acid monoester sulfonate surfactant and a preparation method thereof.
Background
alkyl glycosides (APG) were first synthesized by Emil Fischer of germany in 1893, and were continuously valued and developed by major companies (such as P & G, Henkel, queen, etc.) and colleges and universities up to the 80 th century. The alkyl glycoside is prepared by condensing fatty alcohol and glucose, has the characteristics of nonionic and anionic surfactants, has excellent foaming performance, detergency and compatibility, is non-toxic and easy to biodegrade, and is a more environment-friendly surfactant. However, the water solubility of the long-chain alkyl glycoside is poor, and in order to overcome the defect, alkyl succinic acid monoester sulfonate is introduced to the alkyl glycoside to prepare a novel anionic surfactant, namely alkyl glycoside alkyl succinic acid monoester sulfonate. The introduction of the alkyl succinic acid monoester sulfonate enables the surfactant to have the characteristics of alkyl glycoside and alkyl sulfonate, and the introduction of the succinate also increases the oil removal performance of the surfactant. In addition, under the strong alkaline condition, glucoside parts in molecules are deionized, so that the glucoside parts are negatively charged, the molecules repel each other, and the stability is increased, so that the alkali resistance of the alkyl sulfonate is improved to a certain extent, meanwhile, the introduction of sulfonate anions increases the water solubility of alkyl glycoside, and the introduction of long-chain alkyl can reduce the foaming property of the surfactant to a certain extent. Therefore, the surfactant can be applied to the industries of daily chemicals, textiles and the like, and is particularly suitable for the pretreatment of textiles.
According to the reports of the literature, the modification of the sulfosuccinate of the alkyl glycoside is generally to prepare the alkyl glycoside sulfosuccinate salt by esterification reaction of the alkyl glycoside and maleic anhydride and then sulfonation reaction, such as the literature, "synthesis of monosodium alkyl polyglycoside sulfosuccinate" (proceedings of the university of Guizhou, Nature science, 2006, Vol.36No.5), "synthesis and performance research of sodium starch alkyl glycoside sulfosuccinate" (chemical engineering, 2010, Vol.18No.1) and patent CN 103864863A. In addition, patent CN106459121A discloses that alkyl glycoside and itaconic acid or itaconic anhydride react in the presence of a catalyst to obtain alkyl glycoside itaconate, and then the alkyl glycoside sulfomethylsuccinate is obtained by sulfonation. Patent CN103623744A discloses that maleic anhydride reacts with 1,4 butanediol by single esterification, then reacts with alkyl glycoside to produce double esterification product, and is sulfonated to produce alkyl glycoside gemini surfactant. In the preparation process of the succinic acid sulfonate of alkyl glycoside described in the above documents, organic solvents with high toxicity (such as N-N dimethylformamide, toluene, chlorobenzene, and the like) are used as solvents, and the reaction temperature is high and is above 90 ℃. The succinic acid monoester sulfonate surfactant with alkyl prepared by using alkenyl succinic anhydride as an esterifying agent and carrying out esterification reaction with alkyl glycoside and then sulfonating has not been reported in documents. Alkenyl succinic anhydride is a nucleophilic reagent with strong activity, and has nucleophilic substitution reaction with alkyl glycoside, the reaction is irreversible, the reaction can be completed within the range of 30-60 ℃, and the reaction is simple and easy to operate.
therefore, the alkyl glycoside alkyl succinic acid monoester sulfonate surfactant and the preparation method thereof have important practical significance and application value.
disclosure of Invention
The invention aims to provide an alkyl glycoside alkyl succinic acid monoester sulfonate surfactant and a preparation method thereof.
The chemical structural formula of the alkyl glycoside alkyl succinic acid monoester sulfonate is as follows:
Wherein R 1 is C 6 -C 10 straight-chain or branched-chain alkane;
R 2 is C 6 -C 18 straight chain or branched chain alkyl;
n is 1 to 5;
M is Na, K or NH 4 + or their mixture.
The molecular weight of the alkyl glycoside alkyl succinic acid monoester sulfonate is preferably 600-3000.
The preparation method of the alkyl glycoside alkyl sulfosuccinic acid monoester sulfonate comprises the following steps:
Step one, taking an alcohol water solution as a solvent, dissolving alkyl glycoside, adding an alkaline substance at the temperature of 30-40 ℃ for activation, and activating for 0.5-2 h to obtain an intermediate system A;
Step two, adding alkenyl succinic anhydride into the intermediate system A, carrying out esterification reaction at the temperature of 30-60 ℃, adjusting the pH to be 8.0-10.0 in the reaction process, reacting for 2-4 h, and adjusting the pH to 6-7 to obtain an intermediate system B;
And step three, adding a sulfonating agent aqueous solution into the intermediate system B, and reacting for 2-3 h at the temperature of 70-80 ℃ to obtain the alkyl glycoside alkyl sulfonic acid monoester succinate.
The alkyl glycoside alkyl succinic acid monoester sulfonate surfactant has the characteristics of both alkyl glycoside and alkyl sulfonate, has excellent surface activity, can solve the problems of poor water solubility of the conventional alkyl glycoside and low alkali resistance of the alkyl sulfonate, and can resist 150g/L caustic soda solution.
Drawings
FIG. 1 is an infrared spectrum of the alkyl glycoside alkyl sulfosuccinic acid monoester sulfonate obtained in example 1.
FIG. 2 is an infrared spectrum of the alkyl glycoside alkyl sulfosuccinic acid monoester sulfonate obtained in example 2.
Detailed Description
in a preferred embodiment, an alkyl glycoside alkyl sulfosuccinic acid monoester sulfonate surfactant of the present invention has the chemical formula:
Wherein R 1 is C 6 -C 10 straight-chain or branched-chain alkane, and is more preferably C 6, C 7, C 8 and C 10 straight-chain alkane;
R 2 is a straight chain or branched chain alkyl of C 6 -C 18, more preferably C 8 -C 14;
n is 1 to 5, more preferably 1 to 2;
m is Na, K or NH 4 + or their mixture.
The molecular weight of the alkyl glycoside alkyl succinic acid monoester sulfonate is preferably 600-3000, and more preferably 800-1800.
In a preferred embodiment, the preparation method of the alkyl glycoside alkyl sulfosuccinic acid monoester sulfonate surfactant comprises the following steps:
Step one, taking an alcohol water solution as a solvent, dissolving alkyl glycoside, adding an alkaline substance at the temperature of 30-40 ℃ for activation, and activating for 0.5-2 h to obtain an intermediate system A;
Step two, adding alkenyl succinic anhydride into the intermediate system A, carrying out esterification reaction at the temperature of 30-60 ℃, adjusting the pH to be 8.0-10.0 by using 4-5 wt% of alkaline substance aqueous solution in the reaction process, adjusting the pH to be 6-7 by using 4-5 wt% of hydrochloric acid solution after reacting for 2-4 hours, and obtaining an intermediate system B;
and step three, adding a sulfonating agent aqueous solution into the intermediate system B, and reacting for 2-3 h at the temperature of 70-80 ℃ to obtain the alkyl glycoside alkyl sulfonic acid monoester succinate.
And step four, recovering the solvent under reduced pressure, washing, separating and purifying to obtain a light brown pasty product.
Under the alkaline condition, hydroxyl on alkyl glycoside molecule exposes oxygen anion active group, anhydride ring of nucleophilic reagent alkenyl succinic anhydride is opened, ester bond at one end is combined with oxygen anion, carboxylate is generated at the other end, the reaction is irreversible, sulfonate is introduced after sulfonation reaction, and the generated alkyl glycoside alkyl succinic acid monoester sulfonate is an amphiphilic molecule consisting of hydrophilic group and lipophilic group, has unique molecular structure, excellent surface activity and biodegradability.
In a preferred embodiment, the alkaline substance used in the first step and the second step is one or a mixture of sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate.
in a preferred embodiment, the alcohol used in the first and second steps is one or more of water-soluble isopropanol, n-butanol, sec-pentanol, etc.
in a preferred embodiment, the alkyl glycoside used in the first step includes C 6 -C 18 linear or branched alkyl glycoside with a molecular weight of, for example, 250-800, preferably C 8 -C 12, and a molecular weight of, for example, 300-600.
In a preferred embodiment, in the aqueous alcohol solution used in the first step, the mass ratio of the alcohol to the water is 1:0.1 to 0.5, and more preferably 1:0.2 to 0.4.
In a preferred embodiment, the alkenyl succinic anhydride used in the second step comprises alkenyl succinic anhydride of C 8 -C 12, more preferably Octenyl Succinic Anhydride (OSA), Nonenyl Succinic Anhydride (NSA), dodecenyl succinic anhydride (DDSA), etc.
In a preferred embodiment, the sulfonating agent used in the third step is sodium salt, potassium salt, ammonium salt of sulfurous acid or a mixture thereof.
in a preferred embodiment, the molar ratio of the alkyl glycoside to the alkenyl succinic anhydride is 1:1.0 to 1.5, more preferably 1:1.0 to 1.2.
In a preferred embodiment, the molar ratio of the sulfonating agent to the alkenyl succinic anhydride is 1.1-1.5: 1, more preferably 1.1-1.3: 1.
The applicant innovatively modifies alkyl glycoside, and introduces alkyl succinic acid monoester sulfonate to the alkyl glycoside to prepare the alkyl glycoside alkyl succinic acid monoester sulfonate surfactant. The surfactant has the following advantages: on one hand, water-soluble sulfonate anions are introduced to promote the water solubility of the alkyl glycoside, and simultaneously, the hard water resistance of the alkyl glycoside can be improved; on the other hand, the introduction of the succinate can increase the oil removal performance of the novel surfactant; on the other hand, the introduction of alkyl glycoside can improve the alkali resistance of alkyl sulfonate. The novel surfactant integrates the advantages of alkyl glycoside and alkyl sulfonate, overcomes the respective defects of the alkyl glycoside and the alkyl sulfonate, has the characteristics of low foam and strong emulsifying power, can be applied to the industries of daily chemicals, textiles and the like, and is particularly suitable for the pretreatment of textiles.
Examples
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
The starting materials in the following examples are all commercially available. The experimental data in the following examples were determined according to the following methods:
1) and (3) measuring the molecular weight: measured by HLC-8320GPC type gel permeation chromatography (Nippon Tosoh Co., Ltd.) with DMF as the mobile phase at 25 ℃ and polymethyl methacrylate (PMMA) as the reference.
2) foamability of surfactant: the foaming performance of a surfactant solution with the concentration of 1g/L at the temperature of 60 ℃ is measured by adopting a Roche foamer method, the foam height of the solution at the time of flow interruption is the foaming force of the surfactant, the higher the foam height is, the larger the foaming force is, the ratio of the foam height after 5min to the foam height at the time of flow interruption is the foam stability, and the higher the ratio is, so that the better the foam stability of the surfactant is.
3) emulsifying power of surfactant: 40mL of 2g/L aqueous surfactant solution was sequentially added to a 100mL stoppered cylinder, followed by 40mL of oil (liquid paraffin, white oil, etc.), and the stoppered cylinder was closed. Clamping the measuring cylinder with the plug on a handle of a vertical oscillator, starting the machine, oscillating 10 times at a speed of 5 gears, standing for 1min, repeating the operation for 6 times in total, standing the measuring cylinder on a test bed after the last oscillation is finished, starting timing, observing and recording the time when 10mL of water is separated from the bottom of the measuring cylinder, wherein the longer the time, the better the emulsifying force.
4) Alkali resistance test:
formulation of
Surfactant 15g/L
NaOH xg/L
The working solution prepared by the formula is placed for 4 hours at normal temperature, and whether unstable phenomena such as floating oil, floccules, band-shaped turbidness or precipitation and the like occur in the working solution is observed.
Example 1
in the embodiment, 32g (0.05mol) of alkyl glycoside APG0810 (50% of solid content, Jiangsu Wanqi Biotech Co., Ltd.) and 32ml of isopropanol are added into a four-mouth flask, 2.4g (0.06mol) of NaOH are added at 35 ℃ to carry out activation, 12.5g (0.06mol) of octenyl succinic anhydride (Nanjing Cuita chemical industry) is added after 1h of activation, the reaction is carried out at 35 ℃, the pH value of a system is kept between 8.0 and 8.5 under the condition of 4 to 5 wt% of NaOH aqueous solution in the reaction process, the pH value is adjusted to 6 to 7 under the condition of 4 to 5 wt% of hydrochloric acid solution after 3h of reaction, then 37.5g of 20 wt% (0.072mol) of NaHSO 3 aqueous solution is added, the reaction is carried out for 2h under the condition of 80 ℃, crude product of alkyl glycoside alkyl succinate monoester sulfonate is obtained, the solvent is recovered under reduced pressure, and the light brown product S1 is obtained after washing, separation and purification.
The infrared test is carried out on the obtained product S1, as can be seen from figure 1, a double peak near 1180cm -1 is a vibration peak generated by overlapping different C-O and-SO 3, 1731cm -1 is a stretching vibration peak of C ═ O, 1039cm -1 and 1034cm -1 are stretching vibration peaks of C-O, which indicates that ester is formed, 2975cm -1, 2933cm -1, 2883cm -1 and 1478cm -1 are attached with vibration peaks of-CH 3 and-CH 2, 724cm -1 is attached with a deformation vibration peak of C-H in CH 2 long chain, which indicates that C-H long chain 3403400 cm -1 is attached with O-H stretching vibration peak, which confirms that the product is alkyl glycoside alkyl succinic acid monoester sulfonate, HLC-8320GPC type gel permeation chromatograph tests that the molecular weight of the product is 974.
Example 2
In the embodiment, 64g (0.10mol) of alkyl glycoside APG0810 (Jiangsu Wanqi Biotechnology limited, 50% of solid content) and 64ml of isopropanol are added into a four-mouth flask, NaOH 4.8g (0.12mol) is added at 35 ℃ for activation, dodecenyl succinic anhydride (Nanjing Cuita chemical) 32g (0.12mol) is added after 1H of activation, the reaction is carried out at 45 ℃, the pH value of a 4-5 wt% NaOH aqueous solution condition system is kept between 8.0-8.5 in the reaction process, 4-5 wt% hydrochloric acid solution is used for adjusting the pH to 6-7 after 3H of reaction, 75.0g of 20 wt% (0.144mol) NaHSO 3 aqueous solution is added, the reaction is carried out at 85 ℃ for 2H, a crude product of alkyl glycoside alkyl monosuccinate sulfonate is obtained, a solvent is recovered under reduced pressure, a light brown product S8652 is obtained after washing, separation and purification, the obtained product S2 is tested, the obtained product S2 has a molecular weight as well as a penetrating peak of a TLC-75 cm, a CH 27-75 cm elastic gel, a CH 27-75 cm elastic C elastic peak, a CH-27-75 cm elastic peak is shown in a CH-27-8C elastic vibration-typed long-27-C elastic gel, and a CH-27-C elastic peak which is formed by an infrared vibration-27-C elastic vibration-typed vibration absorption peak of a CH-typed vibration-27-C elastic vibration-typed long-typed vibration absorption peak of an additive.
example 3
in this example, the alkyl glycoside alkyl succinic acid monoester sulfonate surfactants prepared in examples 1 and 2 were tested for foaming property, emulsifying power, and alkali resistance, and the test results are shown in tables 1 and 2.
TABLE 1
| Name of surfactant | Foamability/cm | foam stability |
| S1 | 6.2 | 0.83 |
| S2 | 4.8 | 0.88 |
| SAS60 | 15.5 | 0.30 |
| APG0810 | 13.8 | 0.94 |
TABLE 2
Note: SAS60 (secondary alkyl sodium sulfonate, Clariant), APG0810 (alkyl glycoside, Jiangsu Wanqi Biotech Co., Ltd., 50% solid content) in tables 1 and 2.
TABLE 3
It is seen from table 1 that the alkyl glycoside alkyl succinic acid monoester sulfonate prepared by the present invention has lower foaming property compared with SAS60 and APG0810, and good foam stability. The longer the grafted alkyl carbon chain, the lower the foamability and the higher the foam stability. From Table 2, it is known that their emulsifying power is superior to those of SAS60 and APG 0810. Table 3 also shows that the alkyl glycoside alkyl succinic acid monoester sulfonate surfactant is stable in 150g/L caustic soda solution.
Claims (8)
1. An alkyl glycoside alkyl succinic acid monoester sulfonate surfactant has a chemical structural formula as follows:
Wherein R 1 is C 6 -C 10 straight-chain or branched-chain alkane;
R 2 is C 6 -C 18 straight chain or branched chain alkyl;
n is 1 to 5;
M is Na +, K + or NH 4 + or a mixture thereof.
2. The method for preparing alkyl glycoside alkyl succinic monoester sulfonate surfactant according to claim 1, wherein the preparation method comprises the following steps:
step one, taking an alcohol water solution as a solvent, dissolving alkyl glycoside, and adding an alkaline substance at 30-40 ℃ for activation to obtain an intermediate system A;
Step two, adding alkenyl succinic anhydride into the intermediate system A, carrying out esterification reaction at the temperature of 30-60 ℃, adjusting the pH to be 8.0-10.0 in the reaction process, reacting for 2-4 h, and adjusting the pH to 6-7 to obtain an intermediate system B;
step three, adding a sulfonating agent MHSO 3 aqueous solution into the intermediate system B, reacting for 2-3 h at the temperature of 70-80 ℃ to obtain alkyl glycoside alkyl succinic monoester sulfonate,
Wherein R 1 is C 6 -C 10 straight-chain or branched-chain alkane;
R 2 is C 6 -C 18 straight chain or branched chain alkyl;
n is 1 to 5;
M is Na +, K + or NH 4 + or a mixture thereof.
3. The preparation method according to claim 2, wherein the alkaline substance in the first step is one or a mixture of sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate.
4. The method of claim 2, wherein the alcohol in the first step is water-soluble isopropanol, n-butanol, sec-pentanol or a mixture thereof.
5. The method according to claim 2, wherein the alcohol-water solution in the first step has a mass ratio of alcohol to water of 1:0.1 to 0.5.
6. The method of claim 2, wherein the alkenyl succinic anhydride of step two comprises alkenyl succinic anhydrides of C 8 -C 12.
7. The method according to claim 2, wherein the molar ratio of the alkyl glycoside to the alkenyl succinic anhydride is 1:1.0 to 1.4.
8. The preparation method according to claim 2, wherein the molar ratio of the sulfonating agent to the alkenyl succinic anhydride is 1.1-1.5: 1.
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| CN109999717A (en) * | 2019-04-11 | 2019-07-12 | 中国日用化学研究院有限公司 | A kind of fatty alcohol ether succinate surfactant and preparation method thereof |
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