CN102875613B - Hexadecanol glucose dimeric surfactant and preparation method thereof - Google Patents
Hexadecanol glucose dimeric surfactant and preparation method thereof Download PDFInfo
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 46
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 title claims abstract description 37
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims abstract description 23
- 239000008103 glucose Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 239000003513 alkali Substances 0.000 claims abstract description 9
- -1 acetyl glucosamine tribromo-acetyl imines esters Chemical class 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 claims description 11
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 239000004519 grease Substances 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- MNESLHFFAVMPAT-UHFFFAOYSA-N trifluoromethanesulfonate;trimethylazanium Chemical compound C[NH+](C)C.[O-]S(=O)(=O)C(F)(F)F MNESLHFFAVMPAT-UHFFFAOYSA-N 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 125000003147 glycosyl group Chemical group 0.000 abstract description 2
- HNBQBBSUFYSBJH-GDYHQRTNSA-N (18R,19S,20R)-20-[(1R)-1,2-dihydroxyethyl]-18,19-dihexadecyl-18,19,20-trihydroxyhexatriacontan-17-one Chemical compound CCCCCCCCCCCCCCCCC(=O)[C@@](O)(CCCCCCCCCCCCCCCC)[C@](O)(CCCCCCCCCCCCCCCC)[C@@](O)(CCCCCCCCCCCCCCCC)[C@H](O)CO HNBQBBSUFYSBJH-GDYHQRTNSA-N 0.000 abstract 1
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000012805 post-processing Methods 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 13
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 240000007839 Kleinhovia hospita Species 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical group OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention discloses a hexadecanol glucose dimeric surfactant, which has the structural formula shown as follows. The invention also provides a method for preparing hexadecanol glucose dimeric surfactant. The method comprises the steps as follows: (1) adding hexadecanol glucose dimeric chain, tetracetylglucose trichloroacetimidate and catalyst to an organic solvent I to carry out coupled reaction; then processin to obtain a product I; and (2) adding the product obtained in step (1) to organic solvent II; adding alkali until the acetyl in the product I is completely removed; and carrying out post-processing to obtain the final target product hexadecanol glucose dimeric surfactant after the reaction. The hexadecanol glucose dimeric surfactant disclosed by the invention has the characteristic of the dimeric surfactant of being high in activity, and the feature of being nontoxic and biodegradable, and is the novel green and environment-friendly dimeric surfactant utilizing glycosyl dimeric matter as a model; and moreover, the preparation method of the surfactant is simple, and industrialization is easy to carry out.
Description
Technical field
The present invention relates to tensio-active agent preparation field, be specifically related to a kind of hexadecanol glucose Gemini surface active agent and preparation method thereof.
Background technology
Tensio-active agent and synthetic detergent form one industrially must trace back to 1930's, with the derivative synthetic surfactant of petrochemical materials and washing composition, broken the situation that soap rules all the land, and the research direction of tensio-active agent mainly contains alkyl phosphorus carboxylate salt (AEC) industrialization manufacture, Gemini surface active agent of new generation, AB type block macromolecular tensio-active agent, Bola type tensio-active agent, Dendrimer type tensio-active agent, low bubble or bulb-less surface activity agent at present.Along with the continuous lifting of living standards of the people and environmental consciousness, traditional business type tensio-active agent can not meet this 3 the requirement of people's Surfactant safety, environmental protection and low cost, therefore gradually eliminated, it is instead novel green tensio-active agent.Therefore such as the such green surfactant of Gemini surface active agent, be subject to countries in the world scientist's favor, and started one new research boom.
Gemini surface active agent be by chemical bond by two or more same or same surfactant monomers almost, at hydrophilic base or near with spacer group, this amphiphilic composition being linked together near hydrophilic base, a kind of tensio-active agent of formation.Such tensio-active agent has anionic, non-ionic type, cationic, amphoteric ion type and anion-nonionic type, sun-non-ionic type etc.It has better performance than conventional surfactant the special structures shape of Gemini surface active agent.It has two hydrophilic groups and hydrophobic group, by spacer group, two portions are connected, spacer group has chemical bond, has reduced the reactive force between electrostatic repulsion forces and the hydration layer thereof between bipolarity, makes Gemini surface active agent have low cmc (micelle-forming concentration) characteristic.Gemini surface active agent molecule is because it claims the self-organization behavior that structure produces and reduces the capillary ability of the aqueous solution simultaneously, make it at washing composition, outside widely applying in cosmetic industry, also can in the industry such as such as oil, coal, mining and metallurgy, machinery, weaving, medicine and the production such as agriculture, there be huge potentiality.
Application number is that the patent documentation of CN 201010532886.6 discloses a kind of Gemini surface active agent and preparation method thereof, and the structure of this Gemini surface active agent is suc as formula shown in (I):
Wherein: R is selected from C
8-C
16alkyl; N is the natural number of 1-3, and shown in the formula (I) also providing in the document, the preparation method of cation Gemini surfactant, comprises the steps: 1) C
8-C
16fatty alcohol and epoxy chloropropane react compound shown in production (II) under the condition of basic cpd and phase-transfer catalyst existence, wherein, and the definition cotype (I) of R; 2) under the condition that compound and polyoxyethylene glycol shown in described formula (II) exist at basic metal, react and obtain compound shown in formula (III) through acidifying, the polymerization degree of described polyoxyethylene glycol is 1-3; 3) compound shown in described formula (III) reacts with chlorsulfonic acid and obtains Gemini surface active agent shown in formula (I) through alkalization.The temperature tolerance of the tensio-active agent that above-mentioned document provides, salt resistance, whipability, emulsifying property are stronger, and other type list surface-active agent has good synergy ability.But prepare in above-mentioned Gemini surface active agent process, because epoxy chloropropane is unstable, and volatility is stronger, and has potential carcinogenic toxicity, causes the preparation cost of above-mentioned Gemini surface active agent higher, has also limited its further suitability for industrialized production.
Summary of the invention
The invention provides a kind of hexadecanol glucose Gemini surface active agent, this tensio-active agent surfactivity is high, the chain length characteristic of this Gemini surface active is applicable to use as emulsifying agent and wetting agent, and having nontoxic, biodegradable characteristic, is the Gemini surface active agent of a class new green environment protection.
A kind of hexadecanol glucose Gemini surface active agent, its structure is shown below:
The present invention also provides a kind of method of preparing above-mentioned hexadecanol glucose Gemini surface active agent, comprising:
(1) hexadecanol Shuangzi chain, four acetyl glucosamine tribromo-acetyl imines esters, catalyzer are joined in organic solvent I, carry out ligation, reacted aftertreatment and obtained product I;
(2) product I step (1) being obtained joins in organic solvent II, adds alkali, until the ethanoyl in product I all removes, reaction finishes, and aftertreatment obtains ultimate aim product hexadecanol glucose Gemini surface active agent;
The structure of described hexadecanol Shuangzi chain is shown below:
The structure of four described acetyl glucosamine tribromo-acetyl imines esters is shown below:
The reaction process of above-mentioned reaction is shown below:
In above-mentioned preparation method, the molar weight adding of four described acetyl glucosamine tribromo-acetyl imines esters need to be more than or equal to the twice of the molar weight adding of hexadecanol Shuangzi chain, as preferably, the ratio of the amount of substance of described hexadecanol Shuangzi chain and four acetyl glucosamine tribromo-acetyl imines esters is 1: 2-10.
In above-mentioned preparation method, described catalyzer is conventional organic acid, and the amount adding is catalytic amount, and experiment shows, the good organic acid of catalytic effect is one or both in boron trifluoride diethyl etherate, trifluoromethanesulfonic acid trimethylammonium silicone grease.
Described organic solvent I is to hexadecanol Shuangzi chain, the good non-proton organic solvent of four acetyl glucosamine tribromo-acetyl imines ester solvabilities, generally selects methylene dichloride, trichloromethane, toluene etc.Described organic solvent II is to the good solvent of hexadecanol glucose Gemini surface active agent solvability, the general solvent of selecting to have certain polarity, and such as conventional polar solvent comprises methyl alcohol, ethanol, Virahol etc.
In step (2), described alkali is for common are machine alkali or mineral alkali, and for example described alkali comprises at least one in salt of wormwood, sodium carbonate, sodium methylate, sodium ethylate, sodium hydroxide, potassium hydroxide, sodium hydride.In this step, the add-on of alkali is not strict with, and take ethanoyl, removes completely as object.
Hexadecanol Shuangzi chain, four acetyl glucosamine tribromo-acetyl imines esters that the present invention uses are existing compound, can adopt commercial product, also can adopt existing method to prepare.The present invention is not in the situation that there is no specified otherwise, and reaction is all carried out at normal temperatures.
Hexadecanol glucose Gemini surface active agent of the present invention, both there is the high reactivity feature of Gemini surface active agent, be applicable to use as emulsifying agent and wetting agent, also having nontoxic or low toxicity, biodegradable characteristic, is the Gemini surface active agent of a class take glycosyl Shuangzi thing as the new green environment protection of model; And the preparation method of this tensio-active agent is simple, be easy to realize industrialization.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
Embodiment 1
Take four acetyl glucosamine tribromo-acetyl imines ester 299.6mg (0.61mmol), using 5ml anhydrous methylene chloride as solvent, add hexadecanol Shuangzi chain 134.4mg (0.204mmol), after cooling stirring 15min, add the boron trifluoride diethyl etherate (molar weight be hexadecanol Shuangzi chain molar weight 5%) of catalytic amount, thin-layer chromatography monitoring reaction process, after reaction finishes, through extraction, dry and rotary evaporation, take column chromatography, (eluent is as sherwood oil: ethyl acetate=3: after mode 1) is collected into round-bottomed flask after purifying, rotary evaporation obtains white solid.
Get 199.2mg (0.15mmol) previous step reaction products therefrom using 20ml anhydrous methanol as solvent, add 16.3mg sodium methylate (0.3mmol), reaction finishes rotary evaporation after rear filtration, obtain colourless paste liquid 125.5mg (0.128mmol), productive rate 63%.
White solid is carried out to Structural Identification, and appraising datum is as follows:
Mass spectral characteristi: ESI-MS:m/z981.51[M-H+]-;
Nuclear-magnetism characterizes:
1H?NMR(500MHz，CD
3OD)：δ4.50(m，2H)，4.07(m，2H)，3.85(dt，J＝18.2，5.0Hz，2H)，3.79(dt，J＝7.1，2.4Hz，2H)，3.73to?3.56(m，12H)，3.47(dd，J＝12.0，5.4Hz，4H)，3.41(dd，J＝7.9，2.1Hz，2H)，3.33(s，2H)，3.26-3.21(m，2H)，3.16-3.12(m，2H)，1.61-1.54(m，4H)，1.38-1.27(m，52H)，0.90(t，J＝6.9Hz，6H).
Surfactivity test:
The micelle-forming concentration (cmc) that adopts adopting platinum plate method to measure target product at 20 ℃ is 0.22mmol/L, than corresponding hexadecyl glucopyranoside (cmc=5.32mmol/L) is active, improve 24 times, be suitable for using as emulsifying agent and wetting agent wherein hexadecyl glucopyranoside.
Embodiment 2
Take four acetyl glucosamine tribromo-acetyl imines ester 299.6mg (0.61mmol), using 5ml anhydrous methylene chloride as solvent, add hexadecanol Shuangzi chain 134.4mg (0.204mmol), after cooling stirring 15min, add the trifluoromethanesulfonic acid trimethylammonium silicone grease (molar weight be hexadecanol Shuangzi chain molar weight 5%) of catalytic amount, after reaction finishes, through extraction, dry and rotary evaporation, after purifying in the mode of column chromatography, be collected into rotary evaporation after round-bottomed flask and obtain white solid.
Get 199.2mg (0.15mmol) previous step reaction products therefrom using 20ml anhydrous methanol as solvent, add 16.3mg sodium methylate (0.3mmol), reaction finishes rotary evaporation after rear filtration, obtain colourless paste liquid 141.4mg (0.144mmol), productive rate 71%.
The Structural Identification of the hexadecanol alcohol glucose Gemini surface active agent that this embodiment prepares and surfactivity test data are with embodiment 1.
The reaction reagent using in embodiment 1-2 all can adopt commercial product, or adopt existing method to prepare, wherein, the preparation method of hexadecanol Shuangzi chain can be referring to existing document (Reactions of oligoethylene glycol diglycidyl ethers with hydroxy compounds, Yohji Nakatsuji, Yuichi Tsuji, Isao Ikeda, Mitsuo Okahara, J.Org.Chem.1986,51,78-81).
Claims (6)
1. a hexadecanol glucose Gemini surface active agent, is characterized in that, its structure is shown below:
2. a method of preparing hexadecanol glucose Gemini surface active agent, comprising:
(1) hexadecanol Shuangzi chain, four acetyl glucosamine tribromo-acetyl imines esters, catalyzer are joined in organic solvent I, carry out ligation, reacted aftertreatment and obtained product I; Described catalyzer is one or both in boron trifluoride diethyl etherate, trifluoromethanesulfonic acid trimethylammonium silicone grease;
(2) product I step (1) being obtained joins in organic solvent II, adds alkali, until the ethanoyl in product I all removes, reaction finishes, and aftertreatment obtains ultimate aim product hexadecanol glucose Gemini surface active agent;
The structure of described hexadecanol Shuangzi chain is shown below:
The structure of four described acetyl glucosamine tribromo-acetyl imines esters is shown below:
The structure of described product I is shown below:
The structure of described target product hexadecanol glucose Gemini surface active agent is shown below:
3. the method for preparing hexadecanol glucose Gemini surface active agent according to claim 2, is characterized in that, the ratio of the amount of substance of described hexadecanol Shuangzi chain and four acetyl glucosamine tribromo-acetyl imines esters is 1:2-10.
4. the method for preparing hexadecanol glucose Gemini surface active agent according to claim 2, is characterized in that, described organic solvent I is methylene dichloride, trichloromethane or toluene.
5. the method for preparing hexadecanol glucose Gemini surface active agent according to claim 2, is characterized in that, described organic solvent II is methyl alcohol, ethanol or Virahol.
6. the method for preparing hexadecanol glucose Gemini surface active agent according to claim 2, is characterized in that, described alkali is at least one in salt of wormwood, sodium carbonate, sodium methylate, sodium ethylate, sodium hydroxide, potassium hydroxide, sodium hydride.
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| CN104307430B (en) * | 2014-09-30 | 2016-08-24 | 浙江大学 | A kind of Tetradecanol glucose gemini surfactant compound and preparation method thereof |
| CN107673987B (en) * | 2017-10-10 | 2019-05-03 | 合肥工业大学 | Glucosyl group Shuangzi nonionic surfactant and its synthetic method |
| CN107670583B (en) * | 2017-10-10 | 2019-04-30 | 合肥工业大学 | A kind of glucosyl group Shuangzi nonionic surfactant, amphoteric surfactant and its synthetic method |
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2012
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| CN1128267A (en) * | 1994-09-07 | 1996-08-07 | 希尔斯股份公司 | Process for preparing alkyglycosides |
| WO1998019783A2 (en) * | 1996-11-02 | 1998-05-14 | Henkel Kommanditgesellschaft Auf Aktien | Twin surfactants |
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| Title |
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