CN105646606A - Alkyl glycoside sulfonate and synthesis method thereof - Google Patents
Alkyl glycoside sulfonate and synthesis method thereof Download PDFInfo
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- CN105646606A CN105646606A CN201610037187.1A CN201610037187A CN105646606A CN 105646606 A CN105646606 A CN 105646606A CN 201610037187 A CN201610037187 A CN 201610037187A CN 105646606 A CN105646606 A CN 105646606A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Abstract
The invention relates to the field of synthesis of surfactants, in particular to a synthesis method of alkyl glycoside sulfonate. The method includes the following steps that firstly, epoxy chloropropane and sodium hydrogen sulfite are put into a reactor, and in an aqueous phase environment, epoxy chloropropane performs ring opening for an addition reaction; after the reaction is finished, a product is subjected to recrystallization, suction filtration and drying, and a 3-chloro-2-hydroxylpropysodium sulfonate intermediate is obtained; secondly, the 3-chloro-2-hydroxylpropysodium sulfonate intermediate and long-carbon-chain alkyl glycoside are put into a reactor and are subjected to a condensation reaction in an organic solvent DMF in the presence of a base catalyst, after the reaction is finished, the solvent is removed through suction filtration and reduced-pressure distillation, and alkyl glycoside sulfonate is obtained. According to the method, the process is simple, operation is convenient, the conversion rate is high, and the product purity is high; especially, alkyl glycoside sulfonate has the related properties of a sulfonate surfactant and an alkyl glucoside surfactant, and the problem that long-carbon-chain alkyl glycoside is poor in water solubility is also solved.
Description
Technical field
The present invention relates to the synthesis technical field of glycosides derivatives surfactant, specifically, be a kind of sugar-based sulfonates and synthetic method thereof.
Background technology
Surfactant is the compound that a class has amphiphilic structure, and it is very easily enriched in interface, thus changing interfacial property, interface process is produced material impact. The anion surfactant that alkyl polyglucoside hydroxylpropyl sulfonate is is Material synthesis with alkyl polyglucoside green, environmental protection. Alkyl polyglucoside is then be the novel surfactant of Material synthesis by the glucose of natural reproducible. But due to defects such as the water-soluble difference of long-chain alkyl glucoside, low temperature easily precipitations, research emphasis is transferred to the research aspect of modified alkyl polyglycoside surfactants by Chinese scholars, for instance: alkyl glucoside quaternary ammonium, alkyl polyglucoside carboxylate salts and alkyl polyglucoside ether carboxylate etc. But the research of sugar-based sulfonates is relatively fewer, external U.S.Pat.No.7507399 has sketched and has utilized 1,3-dichloroisopropanol is even synthesized a kind of of sugar-based sulfonates and imagines with hydroxylpropyl sulfonate derivating agent as the bridge of alkyl polyglycoside molecule, but concrete technique is studied.
Sugar-based sulfonates has that nonionic surfactant alkyl polyglucoside is green, natural, nontoxic and the feature such as low irritant, has that the interfacial activity of sulfonate is strong concurrently and the advantage such as hydrophilic simultaneously. Owing to the alkyl polyglucoside of Long carbon chain has the shortcoming such as poorly water-soluble and low temperature easily precipitation, after it is modified, due to sulfonic existence so that it is water solublity increases, and has some advantages of anion surfactant concurrently simultaneously, this just greatly improves its application.
Summary of the invention
It is an object of the invention to for defects such as above-mentioned Long carbon chain alkyl polyglucoside poorly water-soluble and low temperature easily precipitations, it is provided that a kind of method preparing sugar-based sulfonates. Specifically, defect easily muddy when poorly water-soluble and other surfactant compatibilities when it is an object of the invention to use for long-chain alkyl glucoside surfactant self and a kind of synthetic method improving its water miscible sugar-based sulfonates of providing.
A first aspect of the present invention, it is provided that a kind of sugar-based sulfonates, its structural formula is as follows:
��
Wherein, R represents the alkyl chain of different carbon chain lengths, and n is any integer in 1��3.
A second aspect of the present invention, it is provided that the synthetic method of abovementioned alkyl glucosides sulfonate, comprises the following steps:
A, epoxychloropropane and sodium sulfite are put into reactor, in aqueous environment, epoxychloropropane open loop generation additive reaction; After reaction terminates, product through recrystallization, sucking filtration, dry obtain 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate;
B, 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate and Long carbon chain alkyl polyglucoside are put into reactor, under base catalyst existent condition, organic solvent DMF occurs condensation reaction, after reaction terminates, solvent is distilled off through sucking filtration, decompression, obtains sugar-based sulfonates.
In described step A, the mol ratio of epoxychloropropane and sodium sulfite is 1:(1��2), it is preferable that 1:(1.1��1.5), more preferably 1:(1.1��1.3).
The reaction temperature of described step A is 30 DEG C��90 DEG C, it is preferable that 50 DEG C��80 DEG C; Response time is 2��8 hours.
Long carbon chain alkyl polyglucoside in described step B is solid content is the alkyl polyglucoside of 100%, and described alkyl polyglucoside is carbon chain lengths is the alkyl polyglucoside of 12��14, and more preferably solid content is the APG of 100%1214��
In described step B, the mol ratio of Long carbon chain alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate is (1.0��1.8): 1, it is preferable that (1.1��1.4): 1.
The described base catalyst in step B is K2CO3; K2CO3Quality is pure alkyl polyglucoside quality of material 1.0%��42.5%, it is preferable that 3.5%��24.0%.
The reaction temperature of described step B is 40 DEG C��120 DEG C, it is preferable that 60 DEG C��90 DEG C; Response time is 4��10 hours.
Specifically, the method of synthesis abovementioned alkyl glucosides sulfonate is: put into by sodium sulfite in a certain amount of deionized water, epoxychloropropane is added when stirring, epoxychloropropane and sodium sulfite press 1:(1��2) mol ratio add reactor, react 2��8 hours under 30 DEG C��90 DEG C conditions, cooling obtains 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution, its aqueous solution adds a certain amount of methanol, it is placed under 0 DEG C of environment and carries out recrystallization, product is through water and 3 washings of methanol solution, sucking filtration, 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate is obtained after dried, then by 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate and Long carbon chain alkyl polyglucoside be in molar ratio 1:1��1.8 put into reactors, under organic solvent DMF existent condition, continuous stirring, add alkali as catalyst, under 40 DEG C��120 DEG C conditions, reacting 4��10 hours, reaction is lowered the temperature after terminating, through sucking filtration and decompression distillation, obtain transparent or flaxen sugar-based sulfonates.
Advantage of the invention is that two-step reaction process is all disposable feeding intake, intermediate conversion ratio is high, reaction process is simple, the product sugar-based sulfonates conversion ratio obtained is high, reach as high as 88.05%, reaction condition is gentle, the alkyl polyglucoside hydroxylpropyl sulfonate obtained solves Long carbon chain alkyl polyglucoside poorly water-soluble, self aqueous solution or the shortcoming muddy with other surfactant compounds, and the problem such as low temperature easily precipitation, sulfonic introducing simultaneously adds the properties of anion surfactant.
Product is through infrared detection, as it is shown in figure 1, wherein 3300cm-1��3600cm-1For the stretching vibration peak of O-H key, 2850cm-1��2950cm-1For the stretching vibration peak of c h bond, 1633cm in methyl and methylene-1For-SO3The absworption peak of Na, 1152cm-1For the stretching vibration peak of C-O-C key, 1000cm-1��1100cm-1For the stretching vibration peak of C-O key in hydroxyl, it was demonstrated that product is alkyl polyglucoside sodium sulfonate.
The inventive method technique is simple, easy to operate, conversion ratio is high, product purity is high, and particularly sugar-based sulfonates not only has the relevant nature of sulfosalt surfactant and alkyl glucoside surfactant, the problem simultaneously also solving the poorly water-soluble of the alkyl polyglucoside of Long carbon chain.
Accompanying drawing explanation
Fig. 1. the infrared detection figure of product.
Detailed description of the invention
Below in conjunction with embodiment, detailed description of the invention provided by the invention is elaborated.
Embodiment 1
Equipped with motor stirrer, thermometer, in the four-hole bottle of the 250mL of condensing tube, according to the mol ratio of feed intake sodium sulfite and epoxychloropropane for ratio for 1.1:1, add the sodium sulfite of 0.24mol25.00g and the deionized water of 5.56mol100g, stirring is warming up to it and is completely dissolved, when 60 DEG C, the epoxychloropropane of 0.22mol21.00g is slowly added dropwise in reaction system, after reacting 4 hours, solution is become colourless transparent liquid by faint yellow, stopped reaction cooling obtains 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution, the residual recording epoxychloropropane by gas phase is 3.31%.
Equipped with motor stirrer, thermometer, condensing tube 250mL four-hole bottle in, according to the mol ratio that mol ratio is 1.1:1 of alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate, add the APG of solid content 100%12140.0530mol25.00g, and the organic solvent DMF of 50.00g is warmed up to 95 DEG C, the 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate of 10.68g0.0484mol adds in reaction system, simultaneously the K of 3.36g2CO3Adding in reaction system, after reacting 6 hours, solution is become clear by muddiness, and reaction is lowered the temperature after terminating, and obtains sugar-based sulfonates 22.45g after sucking filtration and decompression distillation.
Embodiment 2
Equipped with motor stirrer, thermometer, in the four-hole bottle of the 250mL of condensing tube, according to the mol ratio of feed intake sodium sulfite and epoxychloropropane for ratio for 2:1, add the sodium sulfite of 0.44mol45.82g and the deionized water of 5.56mol100g, stirring is warming up to it and is completely dissolved, when 90 DEG C, the epoxychloropropane of 0.22mol21.00g is slowly added dropwise in reaction system, after reacting 2 hours, solution is become colourless transparent liquid by faint yellow, stopped reaction cooling obtains 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution, the residual recording epoxychloropropane by gas phase is 5.81%.
Equipped with motor stirrer, thermometer, condensing tube 250mL four-hole bottle in, according to the mol ratio that mol ratio is 1:1 of alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate, add the APG of solid content 100%1214The organic solvent DMF of 0.0484mol22.74g, 50.02g is warmed up to the 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate of 80 DEG C of 10.67g0.0484mol and adds in reaction system, 3.35gK simultaneously2CO3Adding in reaction system, after reacting 6 hours, solution is become clear by muddiness, and reaction is lowered the temperature after terminating, and obtains sugar-based sulfonates 20.98g after sucking filtration and decompression distillation.
Embodiment 3
Equipped with motor stirrer, thermometer, in the four-hole bottle of the 250mL of condensing tube, according to the mol ratio of feed intake sodium sulfite and epoxychloropropane for ratio for 1.3:1, add the sodium sulfite of 0.28mol29.54g and the deionized water of 5.56mol100g, stirring is warming up to it and is completely dissolved, when 60 DEG C, the epoxychloropropane of 0.22mol21.00g is slowly added dropwise in reaction system, after reacting 4 hours, solution is become colourless transparent liquid by faint yellow, stopped reaction cooling obtains 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution, the residual recording epoxychloropropane by gas phase is 4.01%.
Equipped with motor stirrer, thermometer, condensing tube 250mL four-hole bottle in, according to the mol ratio that mol ratio is 1.8:1 of alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate, add the APG of 100%1214The organic solvent DMF of 0.0871mol41.09g, 50.00g is warmed up to 60 DEG C, and the 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate of 10.68g0.0484mol adds in reaction system, simultaneously 3.35gK2CO3Adding in reaction system, after reacting 8 hours, solution is become clear by muddiness, and reaction is lowered the temperature after terminating, and obtains sugar-based sulfonates 18.11g after sucking filtration and decompression distillation.
Embodiment 4
Equipped with motor stirrer, thermometer, in the four-hole bottle of the 250mL of condensing tube, according to the mol ratio of feed intake sodium sulfite and epoxychloropropane for ratio for 1.3:1, add the sodium sulfite of 0.28mol29.54g and the deionized water of 5.56mol100g, stirring is warming up to it and is completely dissolved, when 50 DEG C, the epoxychloropropane of 0.22mol21.00g is slowly added dropwise in reaction system, after reacting 4 hours, solution is become colourless transparent liquid by faint yellow, stopped reaction cooling obtains 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution, the residual recording epoxychloropropane by gas phase is 5.01%.
Equipped with motor stirrer, thermometer, condensing tube 250mL four-hole bottle in, according to the mol ratio that mol ratio is 1.3:1 of alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate, add the APG of solid content 100%1214The organic solvent DMF of 0.0629mol29.67g, 50.00g is warmed up to 80 DEG C, and the 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate of 10.68g0.0484mol adds in reaction system, simultaneously 7.12gK2CO3Adding in reaction system, after reacting 6 hours, solution is become clear by muddiness, and reaction is lowered the temperature after terminating, and obtains sugar-based sulfonates 20.42g after sucking filtration and decompression distillation.
Embodiment 5
Equipped with motor stirrer, thermometer, in the four-hole bottle of the 250mL of condensing tube, according to the mol ratio of feed intake sodium sulfite and epoxychloropropane for ratio for 1.1:1, add the sodium sulfite of 0.24mol25.00g and the deionized water of 5.56mol100g, stirring is warming up to it and is completely dissolved, when 30 DEG C, the epoxychloropropane of 0.22mol21.00g is slowly added dropwise in reaction system, after reacting 8 hours, solution is become colourless transparent liquid by faint yellow, stopped reaction cooling obtains 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution, the residual recording epoxychloropropane by gas phase is 7.21%.
Equipped with motor stirrer, thermometer, condensing tube 250mL four-hole bottle in, according to alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate the mol ratio that mol ratio is 1.1:1 add solid content 100% APG1214The organic solvent DMF of 0.0530mol25.00g, 50.00g is warmed up to 120 DEG C, and the 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate of 10.68g0.0442mol adds in reaction system, simultaneously 3.35gK2CO3Adding in reaction system, after reacting 6 hours, solution is become clear by muddiness, and reaction is lowered the temperature after terminating, and obtains sugar-based sulfonates 19.42g after sucking filtration and decompression distillation.
Embodiment 6
Equipped with motor stirrer, thermometer, in the four-hole bottle of the 250mL of condensing tube, according to the mol ratio of feed intake sodium sulfite and epoxychloropropane for ratio for 1:1, add the sodium sulfite of 0.22mol22.72g and the deionized water of 5.56mol100g, stirring is warming up to it and is completely dissolved, when 60 DEG C, the epoxychloropropane of 0.22mol21.00g is slowly added dropwise in reaction system, after reacting 8 hours, solution is become colourless transparent liquid by faint yellow, stopped reaction cooling obtains 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution, the residual recording epoxychloropropane by gas phase is 4.21%.
Equipped with motor stirrer, thermometer, condensing tube 250mL four-hole bottle in, according to the mol ratio that mol ratio is 1.1:1 of alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate, add the APG of solid content 100%12140.0530mol25.00g, and the organic solvent DMF of 50.00g is warmed up to 40 DEG C, the 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate of 10.68g0.0484mol adds in reaction system, simultaneously the K of 0.84g2CO3Adding in reaction system, after reacting 6 hours, solution is become clear by muddiness, and reaction is lowered the temperature after terminating, and obtains sugar-based sulfonates 20.45g after sucking filtration and decompression distillation.
Below the preferred embodiment of the invention has been illustrated, but the invention is not limited to described embodiment, those of ordinary skill in the art it may also be made that under the premise without prejudice to the invention spirit all equivalent modification or replacement, these equivalent modification or replacement are all contained in the application claim limited range.
Claims (10)
1. the synthetic method of a sugar-based sulfonates, it is characterised in that comprise the following steps:
A, epoxychloropropane and sodium sulfite are put into reactor, in aqueous environment, epoxychloropropane open loop generation additive reaction; After reaction terminates, product through recrystallization, sucking filtration, dry obtain 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate;
B, 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate and alkyl polyglucoside are put into reactor, under base catalyst existent condition, organic solvent DMF occurs condensation reaction, after reaction terminates, solvent is distilled off through sucking filtration, decompression, obtains sugar-based sulfonates.
2. the synthetic method of sugar-based sulfonates according to claim 1, it is characterised in that in described step A, the mol ratio of epoxychloropropane and sodium sulfite is 1:(1��2), reaction temperature is 30 DEG C��90 DEG C.
3. the synthetic method of sugar-based sulfonates according to claim 2, it is characterised in that in described step A, the mol ratio of epoxychloropropane and sodium sulfite is 1:(1��1.5), reaction temperature is 50 DEG C��80 DEG C.
4. the synthetic method of sugar-based sulfonates according to claim 1, it is characterised in that the described alkyl polyglucoside in described step B is solid content is 100%, and carbon chain lengths is the alkyl polyglucoside of 12��14.
5. the synthetic method of sugar-based sulfonates according to claim 1, it is characterised in that in described step B, the mol ratio of alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate is (1.0��1.8): 1.
6. the synthetic method of sugar-based sulfonates according to claim 1, it is characterised in that in described step B, the mol ratio of alkyl polyglucoside and 3-chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate is (1.1��1.4): 1.
7. the synthetic method of sugar-based sulfonates according to claim 1, it is characterised in that the described base catalyst in step B is K2CO3��
8. the synthetic method of sugar-based sulfonates according to claim 7, it is characterised in that in described step B, the quality of base catalyst is the 1.0%��42.5% of alkyl polyglucoside quality.
9. the synthetic method of sugar-based sulfonates according to claim 1, it is characterised in that the reaction temperature of described step B is 40 DEG C��120 DEG C.
10. a sugar-based sulfonates, it is characterised in that described sugar-based sulfonates is prepared by the arbitrary described synthetic method of claim 1-9, and the structural formula of described sugar-based sulfonates is as follows:
Wherein, R represents the alkyl chain of different carbon chain lengths, and n is any integer in 1��3.
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Cited By (6)
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| CN108148103A (en) * | 2017-12-30 | 2018-06-12 | 江南大学 | A kind of synthesis technology of alkyl poly glucoside hydroxypropyl azochlorosulfonate acid sodium |
| CN109535042A (en) * | 2018-11-23 | 2019-03-29 | 如皋市万利化工有限责任公司 | A kind of production technology of 3- chlorine-2-hydroxyl propyl- sodium sulfonate |
| CN110305532A (en) * | 2019-07-22 | 2019-10-08 | 浙江海印数码科技有限公司 | A kind of digit printing high-concentration acidic wastewater ink and preparation method thereof |
| CN110947338A (en) * | 2019-12-09 | 2020-04-03 | 南京科技职业学院 | Alkyl glycoside sulfobetaine type amphoteric surfactant and preparation method thereof |
| CN111013484A (en) * | 2019-11-25 | 2020-04-17 | 南京科技职业学院 | Alkyl glycoside carboxyl betaine type zwitterionic surfactant and preparation method thereof |
| CN113201417A (en) * | 2021-04-30 | 2021-08-03 | 厦门普诺尔新材料科技有限公司 | Ultrasonic cleaning agent and preparation method thereof |
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| CN108148103A (en) * | 2017-12-30 | 2018-06-12 | 江南大学 | A kind of synthesis technology of alkyl poly glucoside hydroxypropyl azochlorosulfonate acid sodium |
| CN108148103B (en) * | 2017-12-30 | 2021-02-09 | 江南大学 | Synthesis process of alkyl polyglycoside hydroxypropyl sodium sulfonate |
| CN109535042A (en) * | 2018-11-23 | 2019-03-29 | 如皋市万利化工有限责任公司 | A kind of production technology of 3- chlorine-2-hydroxyl propyl- sodium sulfonate |
| CN110305532A (en) * | 2019-07-22 | 2019-10-08 | 浙江海印数码科技有限公司 | A kind of digit printing high-concentration acidic wastewater ink and preparation method thereof |
| CN111013484A (en) * | 2019-11-25 | 2020-04-17 | 南京科技职业学院 | Alkyl glycoside carboxyl betaine type zwitterionic surfactant and preparation method thereof |
| CN110947338A (en) * | 2019-12-09 | 2020-04-03 | 南京科技职业学院 | Alkyl glycoside sulfobetaine type amphoteric surfactant and preparation method thereof |
| CN110947338B (en) * | 2019-12-09 | 2021-10-12 | 南京科技职业学院 | Alkyl glycoside sulfobetaine type amphoteric surfactant and preparation method thereof |
| CN113201417A (en) * | 2021-04-30 | 2021-08-03 | 厦门普诺尔新材料科技有限公司 | Ultrasonic cleaning agent and preparation method thereof |
| CN113201417B (en) * | 2021-04-30 | 2022-09-02 | 厦门普诺尔新材料科技有限公司 | Ultrasonic cleaning agent and preparation method thereof |
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