CN105646607B - A kind of alkyl glycosides hydroxylpropyl sulfonate and preparation method thereof - Google Patents
A kind of alkyl glycosides hydroxylpropyl sulfonate and preparation method thereof Download PDFInfo
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- CN105646607B CN105646607B CN201610037190.3A CN201610037190A CN105646607B CN 105646607 B CN105646607 B CN 105646607B CN 201610037190 A CN201610037190 A CN 201610037190A CN 105646607 B CN105646607 B CN 105646607B
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- alkyl glycosides
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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 present invention relates to the synthesis fields of surfactant, the preparation method of specifically a kind of alkyl glycosides hydroxylpropyl sulfonate, the following steps are included: A, epoxychloropropane and sodium hydrogensulfite put into reactor, in aqueous environment, addition reaction occurs for epoxychloropropane open loop；After reaction, 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution is obtained；B, 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate and alkyl glycosides aqueous solution are put into reactor, under the conditions of existing for the liquid alkaline catalyst, condensation reaction occurs, obtains sugar-based sulfonates aqueous solution.The method of the present invention simple process, it is easy to operate, the sugar-based sulfonates especially obtained not only have the relevant nature of nonionic surfactant alkyl glycosides, simultaneously because the introducing of sulfonate ion, making the water solubility of product is improved, and which solves the problems that the poorly water-soluble of the alkyl glycosides of Long carbon chain and low temperature are easily precipitated etc..
Description
Technical field
The present invention relates to the synthesis technical fields of glycosides derivatives surfactant, specifically, being a kind of alkyl glycosides
Hydroxylpropyl sulfonate and preparation method thereof.
Background technique
Surfactant is a kind of compound with amphiphilic structure, it is easily enriched in interface, to change interface characteristics
Matter has an important influence on interface process.Alkyl glycosides hydroxylpropyl sulfonate is to be closed using green, the alkyl glycosides of environmental protection as raw material
At anionic surfactant.And alkyl glycosides is lived by the novel surface that the glucose of natural reproducible is Material synthesis
Property agent.But since the water-soluble poor, low temperature of long-chain alkyl glucoside is easy the defects of being precipitated, research emphasis is transferred to by domestic and foreign scholars
In terms of the research of modified alkyl polyglycoside surfactants, such as: alkyl glucoside quaternary ammonium, alkyl glycosides carboxylate salts and alkyl sugar
Glycosides ether carboxylate etc..But it is relatively fewer to the research of sugar-based sulfonates, external U.S.Pat.No.7507399 is sketched
Bridging and hydroxylpropyl sulfonate derivating agent using 1,3- dichloroisopropanol as alkyl polyglycoside molecule react synthesizing alkyl polyglycoside
A kind of imagination of sulfonate, but there is no study specific technique.
Sugar-based sulfonates have green, natural, nontoxic and low irritant of nonionic surfactant alkyl glycosides etc.
Feature, while the interfacial activity that has both sulfonate is strong and the advantages such as hydrophily.Since the alkyl glycosides of Long carbon chain has water solubility
The disadvantages of difference and low temperature are easily precipitated after being modified to it, due to sulfonic presence, increases its water solubility, has both simultaneously
Some advantages of anionic surfactant, its application field is just greatly improved in this.
Summary of the invention
The purpose of the present invention is being easily precipitated for above-mentioned Long carbon chain alkyl glycosides poorly water-soluble and low temperature, one is provided
The method that kind prepares sugar-based sulfonates.Specifically, the purpose of the present invention is be directed to long-chain alkyl glucoside surfactant certainly
Poorly water-soluble when body use, with defect easily muddy when other surfaces active ingredient and a kind of improvement for providing its is water-soluble
The preparation method of sugar-based sulfonates.
The first aspect of the present invention provides a kind of alkyl glycosides hydroxylpropyl sulfonate, and structural formula is as follows:
Wherein, R indicates that the alkyl chain of different carbon chain lengths, n are any integer in 1~3.
The second aspect of the present invention provides the preparation method of abovementioned alkyl glucosides hydroxylpropyl sulfonate, comprising the following steps:
A, epoxychloropropane and sodium hydrogensulfite are put into reactor, in aqueous environment, epoxychloropropane open loop occurs
Addition reaction；After reaction, 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution is obtained；
B, 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate and alkyl glycosides aqueous solution are put into reactor, is catalyzed in liquid alkaline
Under the conditions of agent is existing, condensation reaction occurs, obtains sugar-based sulfonates aqueous solution.
The molar ratio of epoxychloropropane and sodium hydrogensulfite is 1:(1~2 in the step A), preferred 1:(1~1.5).
The reaction temperature of the step A is 30 DEG C~90 DEG C, preferably 50 DEG C~70 DEG C；Reaction time is 2~8 hours.
Alkyl glycosides aqueous solution in the step B is that the Long carbon chain alkyl glycosides that solid content is 30%~70% is water-soluble
The Long carbon chain alkyl glycosides aqueous solution that liquid, preferably solid content are 50%~70%, the APG that more preferable solid content is 50%1214。
The molar ratio of alkyl glycosides aqueous solution and 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate is in the step B
(1.0~1.8): 1, preferably (1.1~1.4): 1.
The NaOH aqueous solution that liquid alkaline catalyst in the step B is 32wt%.
The quality of NaOH aqueous solution is pure alkyl glycosides quality of material in alkyl glycosides aqueous solution in liquid alkaline catalyst
4.0%~31.5%, preferably 11.5%~25.5%.
The reaction temperature of the step B is 40 DEG C~90 DEG C, preferably 65 DEG C~85 DEG C；Reaction time is 4~10 hours.
Specifically, the method for abovementioned alkyl glucosides hydroxylpropyl sulfonate is synthesized are as follows: put into sodium hydrogensulfite a certain amount of
In deionized water, epoxychloropropane is added under stirring conditions, epoxychloropropane and sodium hydrogensulfite are by 1:(1~2) rub
You react 2~8 hours, cooling obtains in 3- chlorine-2-hydroxyl propyl sulfonic acid sodium than reactor is added under the conditions of 30 DEG C~90 DEG C
Mesosome aqueous solution；Then by 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution and certain density alkyl glycosides aqueous solution
In molar ratio it is 1:(1.0~1.8) investment reactor, under stirring conditions, addition liquid alkaline is as catalyst, in 40 DEG C~90
Under the conditions of DEG C, reacts 4~10 hours, obtain transparent or flaxen alkyl glycosides hydroxypropyl sulfonic acid saline solution.Pass through decompression
The method of distillation, which removes water, can be obtained alkyl glycosides hydroxylpropyl sulfonate.
Advantage of the invention is that two-step reaction process is disposably to feed intake, react, and reacts in aqueous environment
Simple process, reaction condition is mild, low temperature, normal pressure, operating aspect, and intermediate high conversion rate reaches as high as 96.24%, obtains
Sugar-based sulfonates due to sulfonic introducing, product clear solves Long carbon chain alkyl glycosides poorly water-soluble, from
Body aqueous solution compounds the shortcomings that muddy with other surfaces activating agent, and one with sulfonate anionic surfactant
A little properties.
Reaction product is through infrared detection, as shown in Figure 1, wherein 3300cm-1~3600cm-1For the stretching vibration of O-H key
Peak, 2850cm-1~2950cm-1For the stretching vibration peak of c h bond in methyl and methylene, 1620cm-1For-SO3The absorption of Na
Peak, 1148cm-1For the stretching vibration peak of C-O-C key, 1000cm-1~1100cm-1For the stretching vibration peak of C-O key in hydroxyl, card
Real product is alkyl glycosides sodium sulfonate.
The method of the present invention simple process, easy to operate, the sugar-based sulfonates especially obtained not only have nonionic
The relevant nature of Surfactants Alkyl, simultaneously because the introducing of sulfonate ion, improves the water solubility of product,
Which solves the problems that the poorly water-soluble of the alkyl glycosides of Long carbon chain and low temperature are easily precipitated etc..
Detailed description of the invention
The infrared detection figure of Fig. 1 reaction product.
Specific embodiment
It elaborates below with reference to embodiment to specific embodiment provided by the invention.
Embodiment 1
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to feed intake sodium hydrogensulfite and
The molar ratio of epoxychloropropane is the sodium hydrogensulfite and 5.56mol 100g than 0.24mol 25.00g for 1.1:1, is added
Deionized water, stirring are warming up to it and are completely dissolved, and under conditions of 60 DEG C, the epoxychloropropane of 0.22mol 21.00g slowly drips
Add as in reaction system, after reaction 4 hours, solution becomes colourless transparent liquid by faint yellow, and it is chloro- that stopping reaction cooling obtains 3-
2- hydroxypropyl sulfonate intermediate water solution is 1.81% with the residual that gas phase measures epoxychloropropane.
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to alkyl glycosides and the chloro- 2- of 3-
The molar ratio of hydroxypropyl sulfonate intermediate is the molar ratio of 1.1:1, and the APG of solid content 50% is added12140.0530mol
50.00g is warming up to 65 DEG C, the 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution fast drop of 31.94g 0.0482mol
Enter in reaction system, while the liquid alkaline (32wt%) of the NaOH of 3.90g is slowly added dropwise in reaction system, it is molten after reaction 6 hours
Liquid becomes clear by muddiness, obtains sugar-based sulfonates aqueous solution.
Embodiment 2
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to feed intake sodium hydrogensulfite and
The molar ratio of epoxychloropropane is the sodium hydrogensulfite and 5.56mol 100g than 0.24mol 25.00g for 1.5:1, is added
Deionized water, stirring are warming up to it and are completely dissolved, and under conditions of 30 DEG C, the epoxychloropropane of 0.16mol 14.08g slowly drips
Add as in reaction system, after reaction 8 hours, solution becomes colourless transparent liquid by faint yellow, and it is chloro- that stopping reaction cooling obtains 3-
2- hydroxypropyl sulfonate intermediate water solution is 5.81% with the residual that gas phase measures epoxychloropropane.
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to alkyl glycosides and the chloro- 2- of 3-
The molar ratio of hydroxypropyl sulfonate intermediate is that the APG of solid content 50% is added in the molar ratio of 1.8:112140.0530mol
50.00g is warming up to the 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution fast drop of 40 DEG C of 20.56g 0.0294mol
Enter in reaction system, while the liquid alkaline (32wt%) of the NaOH of 3.90g is slowly added dropwise in reaction system, it is molten after reaction 8 hours
Liquid becomes clear by muddiness, obtains sugar-based sulfonates aqueous solution.
Embodiment 3
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to feed intake sodium hydrogensulfite and
The molar ratio of epoxychloropropane is than the sodium hydrogensulfite of 0.24mol 25.00g and going for 5.56mol 100g is added for 2:1
Ionized water, stirring is warming up to it and is completely dissolved, and under conditions of 60 DEG C, the epoxychloropropane of 0.12mol 11.10g is added dropwise as anti-
It answers in system, after reaction 4 hours, solution becomes colourless transparent liquid by faint yellow, stops reaction cooling and obtains 3- chlorine-2-hydroxyl
Propyl sulfonic acid sodium intermediate water solution is 4.51% with the residual that gas phase measures epoxychloropropane.
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to alkyl glycosides and the chloro- 2- of 3-
The molar ratio of hydroxypropyl sulfonate intermediate is the molar ratio of 1.1:1, and the APG of solid content 50% is added12140.0530mol
50.00g is warming up to 70 DEG C, the 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution fast drop of 31.94g 0.0481mol
Enter in reaction system, while the liquid alkaline (32wt%) of the NaOH of 6.34g is slowly added dropwise in reaction system, it is molten after reaction 4 hours
Liquid becomes clear by muddiness, obtains sugar-based sulfonates aqueous solution.
Embodiment 4
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to feed intake sodium hydrogensulfite and
The molar ratio of epoxychloropropane is the sodium hydrogensulfite and 5.56mol 100g than 0.24mol 25.00g for 1.1:1, is added
Deionized water, stirring are warming up to it and are completely dissolved, and under conditions of 50 DEG C, the epoxychloropropane of 0.22mol 21.00g slowly drips
Add as in reaction system, after reaction 8 hours, solution becomes colourless transparent liquid by faint yellow, and it is chloro- that stopping reaction cooling obtains 3-
2- hydroxypropyl sulfonate intermediate water solution is 5.64% with the residual that gas phase measures epoxychloropropane.
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to alkyl glycosides and the chloro- 2- of 3-
The molar ratio of hydroxypropyl sulfonate intermediate is that the APG of solid content 50% is added in the molar ratio of 1:112140.0530mol
50.00g is warming up to 65 DEG C, the 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution fast drop of 35.20g 0.0530mol
Enter in reaction system, while the liquid alkaline (32wt%) of the NaOH of 2.93g is slowly added dropwise in reaction system, reacts 10 hours
Afterwards, solution becomes clear by muddiness, obtains sugar-based sulfonates aqueous solution.
Embodiment 5
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to feed intake sodium hydrogensulfite and
The molar ratio of epoxychloropropane is than the sodium hydrogensulfite of 0.24mol 25.00g and going for 5.56mol 100g is added for 1:1
Ionized water, stirring are warming up to it and are completely dissolved, and under conditions of 90 DEG C, the sodium hydrogensulfite of 0.24mol 22.90g is slowly added dropwise
In reaction system, after reaction 2 hours, solution becomes colourless transparent liquid by faint yellow, stops reaction cooling and obtains the chloro- 2- of 3-
Hydroxypropyl sulfonate intermediate water solution is 3.21% with the residual that gas phase measures epoxychloropropane.
Equipped with electric mixer, thermometer, condenser pipe 250mL four-hole bottle in, according to alkyl glycosides and the chloro- 2- of 3-
The molar ratio of hydroxypropyl sulfonate intermediate is the molar ratio of 1.1:1, and the APG of solid content 50% is added12140.0530mol
50.00g is warming up to 90 DEG C, the 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution fast drop of 31.94g 0.0481mol
Enter in reaction system, while the liquid alkaline (32wt%) of the NaOH of 3.90g is slowly added dropwise in reaction system, it is molten after reaction 4 hours
Liquid becomes clear by muddiness, obtains sugar-based sulfonates aqueous solution.
The preferred embodiment of the present invention has been described in detail above, but the invention be not limited to it is described
Embodiment, those skilled in the art can also make various equivalent on the premise of not violating the inventive spirit of the present invention
Variation or replacement, these equivalent variation or replacement are all included in the scope defined by the claims of the present application.
Claims (3)
1. a kind of preparation method of alkyl glycosides hydroxylpropyl sulfonate, which comprises the following steps:
A, epoxychloropropane and sodium hydrogensulfite are put into reactor, in aqueous environment, addition occurs for epoxychloropropane open loop
Reaction；After reaction, 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate water solution is obtained；The epoxychloropropane and sulfurous
The molar ratio of sour hydrogen sodium is 1:(1~1.5), reaction temperature is 50 DEG C~70 DEG C；
B, 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate and alkyl glycosides aqueous solution are put into reactor, is deposited in liquid alkaline catalyst
Under the conditions, condensation reaction occurs, obtains sugar-based sulfonates aqueous solution；The alkyl glycosides aqueous solution is solid content
For 50% APG1214；The molar ratio of the alkyl glycosides aqueous solution and 3- chlorine-2-hydroxyl propyl sulfonic acid sodium intermediate is
(1.0~1.8): 1.
2. the preparation method of alkyl glycosides hydroxylpropyl sulfonate according to claim 1, which is characterized in that the step
The NaOH aqueous solution that liquid alkaline catalyst in B is 32wt%；The aqueous solution quality of NaOH is alkyl glycosides water in liquid alkaline catalyst
The 4.0%~31.5% of pure alkyl glycosides quality of material in solution.
3. the preparation method of alkyl glycosides hydroxylpropyl sulfonate according to claim 1, which is characterized in that the step
The reaction temperature of B is 40 DEG C~90 DEG C.
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| CN108148103B (en) * | 2017-12-30 | 2021-02-09 | 江南大学 | Synthesis process of alkyl polyglycoside hydroxypropyl sodium sulfonate |
| 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 |
| CN113832744B (en) * | 2021-10-12 | 2023-09-19 | 开平市信迪染整厂有限公司 | Environment-friendly clothing dye and application thereof in clothing printing and dyeing |
| CN113832710B (en) * | 2021-11-12 | 2023-12-01 | 浙江金丝狐服饰有限公司 | Crease-resistant fabric and preparation method thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4609478A (en) * | 1984-02-21 | 1986-09-02 | Olin Corporation | Sulfonated alkyl glucosides and use thereof in oil recovery |
| US4977253A (en) * | 1988-10-13 | 1990-12-11 | Huels Aktiengesellschaft | Process for the sulfation of alkyloligoglycosides |
| US7087571B1 (en) * | 2005-01-25 | 2006-08-08 | Colonial Chemical | Alkyl polyglycoside derived sulfosuccinates |
| US7507399B1 (en) * | 2004-08-05 | 2009-03-24 | Surfatech Corporation | Functionalized polymeric surfactants based upon alkyl polyglycosides |
| CN103360436A (en) * | 2012-04-06 | 2013-10-23 | 李庆晨 | Preparation method of alkyl polyglycoside phosphates |
| CN103623744A (en) * | 2013-09-30 | 2014-03-12 | 江苏理工学院 | Alkyl glycoside dimeric surfactant and preparation method thereof |
| CN104607094A (en) * | 2015-02-03 | 2015-05-13 | 上海发凯化工有限公司 | Dissymmetric cationic Gemini surfactant and preparation method thereof |
-
2016
- 2016-01-20 CN CN201610037190.3A patent/CN105646607B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4609478A (en) * | 1984-02-21 | 1986-09-02 | Olin Corporation | Sulfonated alkyl glucosides and use thereof in oil recovery |
| US4977253A (en) * | 1988-10-13 | 1990-12-11 | Huels Aktiengesellschaft | Process for the sulfation of alkyloligoglycosides |
| US7507399B1 (en) * | 2004-08-05 | 2009-03-24 | Surfatech Corporation | Functionalized polymeric surfactants based upon alkyl polyglycosides |
| US7087571B1 (en) * | 2005-01-25 | 2006-08-08 | Colonial Chemical | Alkyl polyglycoside derived sulfosuccinates |
| CN103360436A (en) * | 2012-04-06 | 2013-10-23 | 李庆晨 | Preparation method of alkyl polyglycoside phosphates |
| CN103623744A (en) * | 2013-09-30 | 2014-03-12 | 江苏理工学院 | Alkyl glycoside dimeric surfactant and preparation method thereof |
| CN104607094A (en) * | 2015-02-03 | 2015-05-13 | 上海发凯化工有限公司 | Dissymmetric cationic Gemini surfactant and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| 3-氯-2-羟基丙磺酸钠的合成研究;石莹莹;《山东化工》;20141231;第43卷(第4期);第20-21页 |
| 烷基多苷乙基磺酸钠的合成及其复配性能;刘永如等;《日用化学工业》;20110228;第41卷(第1期);第15-18页 |
| 烷基糖苷衍生物的合成及其应用进展;邹新源等;《应用化工》;20151031;第44卷(第10期);第1916-1920页 |
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