CN104725254A - Preparation method of glycosylated surfactant - Google Patents
Preparation method of glycosylated surfactant Download PDFInfo
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- CN104725254A CN104725254A CN201510079918.4A CN201510079918A CN104725254A CN 104725254 A CN104725254 A CN 104725254A CN 201510079918 A CN201510079918 A CN 201510079918A CN 104725254 A CN104725254 A CN 104725254A
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Abstract
The invention relates to a preparation method of a glycosylated surfactant. The preparation method comprises the following steps: firstly weighing glucose, dissolving the glucose in a methanol solution, then adding long-chain n-alkylamine according to the molar ratio of long-chain n-alkylamine to glucose of (1:1)-(1:6) to react with glucose to prepare alkyl glucosimine, then adding an excessive amount of NaBH4 to perform reaction to prepare an alkyl glycosamine crude product; sequentially washing the crude product with iced anhydrous ethanol and methanol solutions, and performing suction filtration to obtain alkyl glycosamine; further dissolving prepared alkyl glycosamine in the methanol solution, then adding glyoxylic acid according to the molar ratio of glyoxylic acid to alkyl glycosamine of (2:1)-(6:1) to react with alkyl glycosamine so as to prepare a glycosylated surfactant crude product; removing a reaction solvent and unreacted glyoxylic acid in the crude product by a rotating evaporation instrument to obtain the glycosylated surfactant. According to the preparation method provided by the invention, the novel glycosylated surfactant is prepared by reaction of glyoxylic acid and self-made alkyl glycosamine.
Description
Technical field
The present invention relates to technical field of fine, be specifically related to a kind of preparation method of glycosyl type surfactant.
Background technology
Glycosyl type tensio-active agent not only has good surfactivity, and it selects natural glucose to be raw material, has readily biodegradable, to human temperature and, the characteristic of environmentally safe, therefore the synthesis and property research of glycosyl type tensio-active agent receives in recent years and pays close attention to widely.
At present, the kind of glycosyl type tensio-active agent is varied, but can't meet the demand of every profession and trade, therefore, is badly in need of a kind of reaction conditions gentleness of synthesis and has a high surface-active class tensio-active agent.
Summary of the invention
In order to enrich the kind of tensio-active agent, the object of the present invention is to provide
a kind of preparation method of glycosyl type tensio-active agent, to realize adopting gentle condition to synthesize a kind of glycosyl type tensio-active agent of excellent property.
To achieve these goals, the technical solution used in the present invention is:
a kind of preparation method of glycosyl type tensio-active agent, comprise the following steps:
The preparation of step one, alkyl glucose crude product: long chain primary amines and glucose are reacted in methyl alcohol obtained alkyl glucose imines, and then add excessive NaBH
4reaction, obtained alkyl glucose amine crude product;
The purification of step 2, crude product: obtain alkyl glucose amine through the dehydrated alcohol of ice and methanol wash, suction filtration after obtained alkyl glucose amine crude product is first;
The preparation of step 3, glycosyl type tensio-active agent: be dissolved in methyl alcohol by obtained alkyl glucose amine, adds oxoethanoic acid and makes it react, obtained glycosyl type tensio-active agent crude product;
The purification of step 4, glycosyl type tensio-active agent: obtained glycosyl type tensio-active agent crude product is removed impurity through Rotary Evaporators, obtains glycosyl type Surfactant.
In described step one, long chain primary amines and glucose mol ratio are 1:(1 ~ 6), the temperature of reaction of reacting in methyl alcohol is 30 ~ 70 DEG C, the effect of methyl alcohol is herein that reactant is better dissolved, improve the degree of reaction, therefore its consumption need not specifically limit, and meets and dissolves.
Described long chain primary amines is stearylamine, cetylamine, tetradecy lamine, amino dodecane or n-octyl amine.
Described alkyl glucose imines and excessive NaBH
4stir until do not have bubble to produce under normal temperature or ice-water bath, obtain alkyl glucose amine crude product.
In described step 2, adopt absolute ethanol washing to remove glucose and the long chain primary amines of non-complete reaction, then remove dehydrated alcohol by methanol wash, repeated multiple timesly obtain glycosyl type tensio-active agent.
In described step 3, the mol ratio of alkyl glucose amine and oxoethanoic acid is 1:(2 ~ 6), stirring reaction 5 ~ 10h at 40 ~ 80 DEG C.The effect of methyl alcohol herein the poly-hydroxy chain of alkyl glucose is unfolded more easily dissolve, and therefore its consumption need not specifically limit, and meets and dissolve.
In described step 4, adopt underpressure distillation, utilize Rotary Evaporators to remove methyl alcohol and unreacted oxoethanoic acid, obtain glycosyl type tensio-active agent.
Compared with prior art, the present invention has the following advantages:
The present invention can synthesize a series of tensio-active agent according to the difference of long chain primary amines, and the tensio-active agent of synthesis all has high surfactivity and environment friendly.Therefore, these series product have a good application prospect.And the aldehydic acid compounds with the similar different lengths of oxoethanoic acid can be selected to carry out the synthesis of tensio-active agent and the mensuration of performance thereof.
Accompanying drawing explanation
figure1 is product synthetic route of the present invention
figure.
Embodiment
Below in conjunction with embodiment, the present invention is described in further details.
Embodiment one
a kind of preparation method of glycosyl type tensio-active agent, comprise the steps:
Step one: take 6g glucose, be dissolved in 100mL methyl alcohol at 60 DEG C, then according to the ratio of stearylamine and glucose mol ratio 1:1, add stearylamine and make itself and glucose stirring reaction 8h at 60 DEG C, obtained alkyl glucose imines, and then add excessive NaBH
4and stir until do not have bubble to produce under normal temperature or ice-water bath, obtained alkyl glucose amine crude product;
Step 2: obtain alkyl glucose amine through the dehydrated alcohol of ice and methanol wash, suction filtration after obtained alkyl glucose amine crude product is first;
Step 3: obtained alkyl glucose amine being dissolved in temperature is again in the 100mL methyl alcohol of 70 DEG C, then according to the ratio of oxoethanoic acid and alkyl glucose amine mol ratio 2:1, add oxoethanoic acid and make itself and alkyl glucose amine stirring reaction 10h at 70 DEG C, obtained glycosyl type tensio-active agent crude product;
Step 4: obtained glycosyl type tensio-active agent crude product is removed reaction solvent and unreacted oxoethanoic acid through Rotary Evaporators at 85 DEG C, obtains glycosyl type Surfactant.
The synthetic route of product
figureas
figureshown in 1.
Embodiment two
a kind of preparation method of glycosyl type tensio-active agent, comprise the steps:
Step one: take 6g glucose, be dissolved in 100mL methyl alcohol at 55 DEG C, then according to the ratio of cetylamine and glucose mol ratio 1:1, add cetylamine and make itself and glucose stirring reaction 8h at 55 DEG C, obtained alkyl glucose imines, and then add excessive NaBH
4and stir until do not have bubble to produce under normal temperature or ice-water bath, obtained alkyl glucose amine crude product;
Step 2: obtain alkyl glucose amine through the dehydrated alcohol of ice and methanol wash, suction filtration after obtained alkyl glucose amine crude product is first;
Step 3: obtained alkyl glucose amine being dissolved in temperature is again in the 100mL methyl alcohol of 60 DEG C, then according to the ratio of oxoethanoic acid and alkyl glucose amine mol ratio 2:1, add oxoethanoic acid and make itself and alkyl glucose amine stirring reaction 10h at 60 DEG C, obtained glycosyl type tensio-active agent crude product;
Step 4: obtained glycosyl type tensio-active agent crude product is removed reaction solvent and unreacted oxoethanoic acid through Rotary Evaporators at 85 DEG C, obtains glycosyl type Surfactant.
Embodiment three
a kind of preparation method of glycosyl type tensio-active agent, comprise the steps:
Step one: take 6g glucose, be dissolved in 100mL methyl alcohol at 50 DEG C, then according to the ratio of amino dodecane and glucose mol ratio 1:1, add amino dodecane and make itself and glucose stirring reaction 8h at 50 DEG C, obtained alkyl glucose imines, and then add excessive NaBH
4and stir until do not have bubble to produce under normal temperature or ice-water bath, obtained alkyl glucose amine crude product;
Step 2: obtain alkyl glucose amine through the dehydrated alcohol of ice and methanol wash, suction filtration after obtained alkyl glucose amine crude product is first;
Step 3: obtained alkyl glucose amine being dissolved in temperature is again in the 100mL methyl alcohol of 60 DEG C, then according to the ratio of oxoethanoic acid and alkyl glucose amine mol ratio 2:1, add oxoethanoic acid and make itself and alkyl glucose amine stirring reaction 10h at 60 DEG C, obtained glycosyl type tensio-active agent crude product;
Step 4: obtained glycosyl type tensio-active agent crude product is removed reaction solvent and unreacted oxoethanoic acid through Rotary Evaporators at 85 DEG C, obtains glycosyl type Surfactant.
Embodiment four
a kind of preparation method of glycosyl type tensio-active agent, comprise the steps:
Step one: take 6g glucose, be dissolved in 100mL methyl alcohol at 45 DEG C, then according to the ratio of n-octyl amine and glucose mol ratio 1:1, add n-octyl amine and make itself and glucose stirring reaction 8h at 45 DEG C, obtained alkyl glucose imines, and then add excessive NaBH
4and stir until do not have bubble to produce under normal temperature or ice-water bath, obtained alkyl glucose amine crude product;
Step 2: obtain alkyl glucose amine through the dehydrated alcohol of ice and methanol wash, suction filtration after obtained alkyl glucose amine crude product is first;
Step 3: obtained alkyl glucose amine being dissolved in temperature is again in the 100mL methyl alcohol of 55 DEG C, then according to the ratio of oxoethanoic acid and alkyl glucose amine mol ratio 2:1, add oxoethanoic acid and make itself and alkyl glucose amine stirring reaction 10h at 55 DEG C, obtained glycosyl type tensio-active agent crude product;
Step 4: obtained glycosyl type tensio-active agent crude product is removed reaction solvent and unreacted oxoethanoic acid through Rotary Evaporators at 85 DEG C, obtains glycosyl type Surfactant.
For amino dodecane, checking is carried out to the foaminess of gained promoting agent of the present invention and foam stability as follows:
Configuration quality concentration is the surfactant soln of 2.5g/L, getting 10ml surfactant soln adds in 50ml test tube, concuss, characterizes latherability, with the stability of foam height ratio characterization of foam when foam height during 5min and 30s with foam height during 30s.Experimental data following (carrying out 3 parallel tests):
Data processing:
Visible, this kind of Surfactants exhibit goes out good foam performance, the foam stability energy simultaneously had.
Claims (7)
1. a preparation method for glycosyl type tensio-active agent, is characterized in that, comprises the following steps:
The preparation of step one, alkyl glucose crude product: long chain primary amines and glucose are reacted in methyl alcohol obtained alkyl glucose imines, and then add excessive NaBH
4reaction, obtained alkyl glucose amine crude product;
The purification of step 2, crude product: obtain alkyl glucose amine through the dehydrated alcohol of ice and methanol wash, suction filtration after obtained alkyl glucose amine crude product is first;
The preparation of step 3, glycosyl type tensio-active agent: be dissolved in methyl alcohol by obtained alkyl glucose amine, adds oxoethanoic acid and makes it react, obtained glycosyl type tensio-active agent crude product;
The purification of step 4, glycosyl type tensio-active agent: obtained glycosyl type tensio-active agent crude product is removed impurity through Rotary Evaporators, obtains glycosyl type Surfactant.
2. the preparation method of a kind of glycosyl type tensio-active agent according to claim 1, is characterized in that, in described step one, long chain primary amines and glucose mol ratio are 1:(1 ~ 6), the temperature of reaction of reacting in methyl alcohol is 30 ~ 70 DEG C.
3. the preparation method of a kind of glycosyl type tensio-active agent according to claim 1, it is characterized in that, described long chain primary amines is stearylamine, cetylamine, tetradecy lamine, amino dodecane or n-octyl amine.
4. the preparation method of a kind of glycosyl type tensio-active agent according to claim 1, is characterized in that, described alkyl glucose imines and excessive NaBH
4stir until do not have bubble to produce under normal temperature or ice-water bath, obtain alkyl glucose amine crude product.
5. the preparation method of a kind of glycosyl type tensio-active agent according to claim 1, it is characterized in that, in described step 2, absolute ethanol washing is adopted to remove glucose and the long chain primary amines of non-complete reaction, remove dehydrated alcohol by methanol wash again, repeated multiple timesly obtain glycosyl type tensio-active agent.
6. the preparation method of a kind of glycosyl type tensio-active agent according to claim 1, is characterized in that, in described step 3, the mol ratio of alkyl glucose amine and oxoethanoic acid is 1:(2 ~ 6), stirring reaction 5 ~ 10h at 40 ~ 80 DEG C.
7. the preparation method of a kind of glycosyl type tensio-active agent according to claim 1, is characterized in that, in described step 4, adopts underpressure distillation, utilizes Rotary Evaporators to remove methyl alcohol and unreacted oxoethanoic acid, obtains glycosyl type tensio-active agent.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105419765A (en) * | 2015-11-06 | 2016-03-23 | 西南石油大学 | Glycosyl anionic-nonionic surfactant and method for preparing same |
| CN105482126A (en) * | 2015-12-31 | 2016-04-13 | 陕西科技大学 | Aldehyde group-terminated hyperbranched polymer leather retanning agent and preparation method thereof |
| CN106986900A (en) * | 2017-05-11 | 2017-07-28 | 盐城通海生物科技有限公司 | A kind of preparation method of N alkyl glucoses imines |
| CN111620916A (en) * | 2020-06-29 | 2020-09-04 | 天津科技大学 | Synthesis method of alkyl amino glucoside |
| CN112441933A (en) * | 2020-12-11 | 2021-03-05 | 山东德仕化工有限公司 | High-temperature acidification corrosion inhibition synergist, preparation method thereof and corrosion inhibition composition |
| CN112500300A (en) * | 2020-12-11 | 2021-03-16 | 山东德仕化工有限公司 | Polyoxyethylene alkylphenol ether water-based wax inhibitor and preparation method and application thereof |
| CN113912506A (en) * | 2021-11-10 | 2022-01-11 | 盐城通海生物科技有限公司 | N-alkylglucosamine fixed bed continuous synthesis process |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105419765A (en) * | 2015-11-06 | 2016-03-23 | 西南石油大学 | Glycosyl anionic-nonionic surfactant and method for preparing same |
| CN105419765B (en) * | 2015-11-06 | 2017-12-05 | 西南石油大学 | A kind of glycosyl the moon nand-type surfactant and preparation method thereof |
| CN105482126A (en) * | 2015-12-31 | 2016-04-13 | 陕西科技大学 | Aldehyde group-terminated hyperbranched polymer leather retanning agent and preparation method thereof |
| CN105482126B (en) * | 2015-12-31 | 2018-04-20 | 陕西科技大学 | A kind of terminal aldehyde hyper branched polymer leather retanning agent and preparation method thereof |
| CN106986900A (en) * | 2017-05-11 | 2017-07-28 | 盐城通海生物科技有限公司 | A kind of preparation method of N alkyl glucoses imines |
| CN106986900B (en) * | 2017-05-11 | 2019-11-05 | 盐城通海生物科技有限公司 | A kind of preparation method of N- alkyl glucose imines |
| CN111620916A (en) * | 2020-06-29 | 2020-09-04 | 天津科技大学 | Synthesis method of alkyl amino glucoside |
| CN112441933A (en) * | 2020-12-11 | 2021-03-05 | 山东德仕化工有限公司 | High-temperature acidification corrosion inhibition synergist, preparation method thereof and corrosion inhibition composition |
| CN112500300A (en) * | 2020-12-11 | 2021-03-16 | 山东德仕化工有限公司 | Polyoxyethylene alkylphenol ether water-based wax inhibitor and preparation method and application thereof |
| CN113912506A (en) * | 2021-11-10 | 2022-01-11 | 盐城通海生物科技有限公司 | N-alkylglucosamine fixed bed continuous synthesis process |
| CN113912506B (en) * | 2021-11-10 | 2023-10-24 | 盐城通海生物科技有限公司 | Fixed bed continuous synthesis process of N-alkyl glucosamine |
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