CN102872752B - Decanol glucose dimeric surfactant and preparation method thereof - Google Patents
Decanol glucose dimeric surfactant and preparation method thereof Download PDFInfo
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- CN102872752B CN102872752B CN201210356288.7A CN201210356288A CN102872752B CN 102872752 B CN102872752 B CN 102872752B CN 201210356288 A CN201210356288 A CN 201210356288A CN 102872752 B CN102872752 B CN 102872752B
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- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 71
- 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 28
- 239000008103 glucose Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 239000003513 alkali Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 238000005859 coupling reaction Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- -1 acetyl glucosamine tribromo-acetyl imines esters Chemical class 0.000 claims description 16
- 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 12
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000004519 grease Substances 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- 238000012805 post-processing Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 229940072033 potash 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
- 230000000694 effects Effects 0.000 abstract description 4
- 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
- 239000000539 dimer Substances 0.000 abstract 1
- 231100000956 nontoxicity Toxicity 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002390 rotary evaporation Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000003147 glycosyl group Chemical group 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JDRSMPFHFNXQRB-IWQYDBTJSA-N (3r,4s,5s,6r)-2-decoxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CCCCCCCCCCOC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JDRSMPFHFNXQRB-IWQYDBTJSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 238000005065 mining Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000009941 weaving Methods 0.000 description 2
- 0 *C(CO)CON Chemical compound *C(CO)CON 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 240000007839 Kleinhovia hospita Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002131 composite material 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
- 238000005516 engineering process Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 239000000203 mixture Substances 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
- 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
- 238000007086 side reaction Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Detergent Compositions (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention discloses a decanol glucose dimeric surfactant, which has a structural formula in the specifications. The invention also provides a method for preparing the decanol glucose dimeric surfactant. The method comprises the following steps of: (1) adding a decanol dimer chain, tetracetylglucose trichloroacetimidate and a catalyst into an organic solvent I for coupled reaction, and after the reaction is finished, obtaining a product I; and (2) adding the product I obtained in the step (1) into an organic solvent II, adding alkali until acetyls are totally removed from the product I, finishing the reaction, and performing posttreatment to obtain the final target product, namely the decanol glucose dimeric surfactant. The decanol glucose dimeric surfactant has the characteristic of high activity of a dimeric surfactant, also has the characteristics of no toxicity and biological degradability, and is a novel environment-friendly dimeric surfactant taking a sugar-based dimer as a template; and moreover, the preparation method for the surfactant is simple and suitable for industrialization.
Description
Technical field
The present invention relates to surfactant field, specifically relate to a kind of decyl alcohol glucose Gemini surface active agent and preparation method thereof.
Background technology
Surfactant and synthetic detergent form one industrially must trace back to 1930's, with the derivative synthetic surfactant of petrochemical materials and washing agent, broken the situation that soap rules all the land, and the research direction of surfactant mainly contains alkyl phosphorus carboxylate (AEC) industrialization manufacture, Gemini surface active agent of new generation, AB type block macromolecular surfactant, Bola type surfactant, Dendrimer type surfactant, low bubble or bulb-less surface activity agent at present.Continuous lifting along with living standards of the people and environmental consciousness, traditional business type surfactant can not meet people's Surfactant safety, environmental protection and low-cost this requirement of 3, therefore gradually eliminated, it is instead novel green surfactant.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 near hydrophilic base, with spacer group, this amphiphilic composition is linked together to a kind of surfactant of formation.Such surfactant has anionic, nonionic, cationic, amphoteric ion type and anion-nonionic type, sun-nonionic 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 parts are connected, spacer group has chemical bond, has reduced electrostatic repulsion forces between bipolarity and the active force between hydrated sheath thereof, makes Gemini surface active agent have low CMC (critical micelle concentration) characteristic.Gemini surface active agent molecule is because it claims the self-organizing behavior that structure produces and reduces the capillary ability of the aqueous solution simultaneously, make it at washing agent, outside widely applying in cosmetics industry, also can in industry such as oil, coal, mining and metallurgy, machinery, weaving, medicine and the production such as agriculture, there be huge potentiality.
Glycosyl Gemini surface active agent is a kind of novel Gemini surface active agent, has the surface-active that is better than traditional commerce surfactant.And, carbohydrate is as a kind of compound of food stage, numerous at occurring in nature content, not only can greatly reduce the cost of producing surfactant, effectively utilize the materials such as some trade waste, also have microbe killing properties, antistatic behaviour and the less advantages such as excitant, and can carry out compositely with other conventional surfactants, have synergistic function.The report of at present relevant Gemini surface active agent is more, but the report of relevant glycosyl Gemini surface active agent is less, the patent documentation that mainly contains application number and be CN 201010538350.5 discloses a kind of sugar-based quaternary ammonium salt Gemini surface active agent, and its general structure is as follows:
In above formula: glycosyl is glucosyl group, R is C
8～C
18chain alkyl, X is chlorine, bromine or iodine, m=1～2, n=1～2.The method is simple, and step consists of direct synthesis dihalo glucosides and quaterisation, and synthesis technique is simple, and equipment requirement is low, is applicable to industrialization.Sugar-based quaternary ammonium salt structurally not only has the glucose hydrophilic group of nonionic, and has cationic bi-quaternary ammonium salt hydrophilic group; Product has outside bactericidal properties, antistatic behaviour and the anti-hard water of cationic surfactant, and excitant is lower; Product can be composite with anion surfactant, has synergistic function simultaneously; As Gemini surface active agent, possessed again the excellent properties of Gemini surface active agent, be a kind of Mobyneb surfactant simultaneously, may be widely used in the industries such as weaving, papermaking, cosmetics and mining, has potential application foreground.Yet only one or more glycosyl Gemini surface active agents are difficult to meet the demand in market.Existing market is badly in need of the new glycosyl Gemini surface active agent of exploitation and new synthetic method.
Summary of the invention
The invention provides a kind of decyl alcohol glucose Gemini surface active agent, this surfactant has higher surface-active, during as solubilizer, solubilizing effect is better, and this Gemini surface active agent has nontoxic, biodegradable characteristic, is the Gemini surface active agent of a class new green environment protection.
The present invention also provides a kind of preparation method who prepares above-mentioned decyl alcohol glucose Gemini surface active agent, and the method step is simple, easy to operate, and overall process avoids adopting toxic solvent, can conveniently realize suitability for industrialized production.
A decyl alcohol glucose Gemini surface active agent, its structure is shown below:
The present invention also provides a kind of method of preparing above-mentioned decyl alcohol glucose Gemini surface active agent, comprising:
(1) decyl alcohol Shuangzi chain, four acetyl glucosamine tribromo-acetyl imines esters, catalyst are joined in organic solvent I, carry out coupled reaction, reacted post processing and obtained product I;
(2) product I step (1) being obtained joins in organic solvent II, adds alkali, until the acetyl group in product I all removes, reaction finishes, and post processing obtains final goal product decyl alcohol glucose Gemini surface active agent;
The structure of described decyl alcohol Shuangzi chain is shown below:
The structure of four described acetyl glucosamine tribromo-acetyl imines esters is shown below:
The course of reaction of above-mentioned reaction is shown below:
In above-mentioned preparation method, the mole adding of four described acetyl glucosamine tribromo-acetyl imines esters need to be more than or equal to the twice of the mole adding of decyl alcohol Shuangzi chain, as preferably, the ratio of the amount of substance of described decyl alcohol Shuangzi chain and four acetyl glucosamine tribromo-acetyl imines esters is 1: 2-10.
In above-mentioned preparation method, described catalyst 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 BFEE, TFMS trimethyl silicone grease.
Described organic solvent I is to decyl alcohol Shuangzi chain, the good non-proton organic solvent of four acetyl glucosamine tribromo-acetyl imines ester dissolubilities, generally selects carrene, chloroform, toluene etc.Described organic solvent II is to the good solvent of decyl alcohol glucose Gemini surface active agent dissolubility, and the general solvent of selecting to have certain polarity, comprises methyl alcohol, ethanol, isopropyl alcohol etc. such as conventional polar solvent.
In step (2), described alkali is for common are machine alkali or inorganic base, and for example described alkali comprises at least one in potash, sodium carbonate, sodium methoxide, caustic alcohol, NaOH, potassium hydroxide, sodium hydride.In this step, the addition of alkali is not strict with, and the acetyl group of take removes completely as object.
Decyl alcohol 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.
Decyl alcohol glucose Gemini surface active agent of the present invention, the high activity feature both with Gemini surface active agent, being suitable for using as solubilizer, having nontoxic, biodegradable characteristic simultaneously, is that a class be take the Gemini surface active agent of the new green environment protection that glycosyl Shuangzi thing is model; And the preparation method of this surfactant is simple, be easy to realize industrialization.
The specific 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 295.6mg (0.6mmol), using 5ml anhydrous methylene chloride as solvent, add decyl alcohol Shuangzi chain 98.08mg (0.2mmol), the BFEE (mole be decyl alcohol Shuangzi chain mole 5%) that adds catalytic amount after cooling stirring 15min, thin-layer chromatography monitoring reaction process, reaction finishes by extraction, dry and rotary evaporation, and (eluant, eluent is benzinum: ethyl acetate=3: after mode 1) is collected into round-bottomed flask after purifying, rotary evaporation obtains light yellow liquid to take column chromatography.
(methyl alcohol adding is excessive with 20ml absolute methanol to get 115.1mg (0.1mmol) previous step reaction products therefrom, during object in order to cushion the pH value that adds alkali process, avoid that local pH value is excessive causes occurring side reaction) as solvent, add 10.8mg sodium methoxide (0.2mmol), after reaction finishes, filter rotary evaporation, obtaining colourless paste liquid is decyl alcohol glucose Gemini surface active agent 70.5mg (0.0864mmol), productive rate 43%.
Colourless paste liquid is carried out to Structural Identification, and appraising datum is as follows:
Mass spectral characteristi: ESI-MS:m/z 813.36[M-H+]-;
Nuclear-magnetism characterizes:
1H?NMR(500MHz，CD
3OD)δ?4.52(m，2H)，4.07(m，2H)，3.86(m，2H)，3.79(m，2H)，3.74-3.60(ddd，J＝14.9，10.3，4.9Hz，12H)，3.47(m，4H)，3.41(dd，J＝9.3，3.1Hz，2H)，3.35(s，2H)，3.26-3.12(dd，J＝14.5，7.2Hz，4H)，1.60-1.53(m，4H)，1.40?to?1.25(m，28H)，0.89(t，J＝6.9Hz，6H).
Surface-active test:
The critical micelle concentration (cmc) that adopts adopting platinum plate method to measure target product at 20 ℃ is 0.11mmol/L, than corresponding list surfactant decyl glucopyranoside (cmc=2.04mmol/L) is active, improve 19 times, activity is higher, be suitable for using as the solubilizer of biological field, wherein, the structure of decyl glucopyranoside is as follows:
Embodiment 2
Take four acetyl glucosamine tribromo-acetyl imines ester 295.6mg (0.6mmol), using 5ml anhydrous methylene chloride as solvent, add decyl alcohol Shuangzi chain 98.08mg (0.2mmol), the TFMS trimethyl silicone grease (mole be decyl alcohol Shuangzi chain mole 5%) that adds catalytic amount after cooling stirring 15min, reaction finishes by extraction, dry and rotary evaporation, take after the mode of column chromatography is purified, be collected into round-bottomed flask after rotary evaporation obtain light yellow liquid as decyl alcohol glucose Gemini surface active agent.
Get 115.1 (0.1mmol) previous step reaction products therefrom and using 20ml absolute methanol as solvent, add 10.8mg sodium methoxide (0.2mmol), reaction finishes rotary evaporation after rear filtration, obtains colourless paste liquid 78.9mg (0.0967mmol), productive rate 48%.
The Structural Identification of the decyl alcohol glucose Gemini surface active agent that this embodiment prepares and surface-active test data are with embodiment 1.
Embodiment 3
Take four acetyl glucosamine tribromo-acetyl imines ester 589.2mg (1.2mmol), using 5ml anhydrous methylene chloride as solvent, add decyl alcohol Shuangzi chain 98.08mg (0.2mmol), the TFMS trimethyl silicone grease (mole be decyl alcohol Shuangzi chain mole 5%) that adds catalytic amount after cooling stirring 15min, reaction finishes by extraction, dry and rotary evaporation, after purifying in the mode of column chromatography, be collected into round-bottomed flask after rotary evaporation obtain light yellow liquid.
Get 117.0mg (0.1mmol) previous step reaction products therefrom and using 20ml absolute methanol as solvent, add 5.0mg sodium hydride (0.2mmol), reaction finishes rotary evaporation after rear filtration, obtaining colourless paste liquid is decyl alcohol glucose Gemini surface active agent 75.3mg (0.0923mmol), productive rate 46%.
The Structural Identification of the decyl alcohol glucose Gemini surface active agent that this embodiment prepares and surface-active test data are with embodiment 1.
The reaction reagent using in embodiment 1-3 all can adopt commercial product, or adopt existing method to prepare, wherein, the preparation method of decyl alcohol Shuangzi chain can be referring to existing document (Reactions ofoligoethylene glycol diglycidyl ethers with hydroxy compounds, YohjiNakatsuji, Yuichi Tsuji, Isao Ikeda, Mitsuo Okahara, J.Org.Chem.1986,51,78-81).
Claims (6)
1. a decyl alcohol glucose Gemini surface active agent, is characterized in that, its structure is shown below:
2. a method of preparing decyl alcohol glucose Gemini surface active agent described in claim 1, comprising:
(1) decyl alcohol Shuangzi chain, four acetyl glucosamine tribromo-acetyl imines esters, catalyst are joined in organic solvent I, carry out coupled reaction, reacted post processing and obtained product I;
Described catalyst is one or both in BFEE, TFMS trimethyl silicone grease;
(2) product I step (1) being obtained joins in organic solvent II, adds alkali, until the acetyl group in product I all removes, reaction finishes, and post processing obtains final goal product decyl alcohol glucose Gemini surface active agent;
The structure of described decyl alcohol 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 decyl alcohol glucose Gemini surface active agent is shown below:
3. the method for preparing decyl alcohol glucose Gemini surface active agent according to claim 2, is characterized in that, the ratio of the amount of substance of described decyl alcohol Shuangzi chain and four acetyl glucosamine tribromo-acetyl imines esters is 1:2-10.
4. the method for preparing decyl alcohol glucose Gemini surface active agent according to claim 2, is characterized in that, described organic solvent I is carrene, chloroform or toluene.
5. the method for preparing decyl alcohol glucose Gemini surface active agent according to claim 2, is characterized in that, described organic solvent II is methyl alcohol, ethanol or isopropyl alcohol.
6. the method for preparing decyl alcohol glucose Gemini surface active agent according to claim 2, is characterized in that, described alkali is at least one in potash, sodium carbonate, sodium methoxide, caustic alcohol, NaOH, 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 |
| CN111992134B (en) * | 2020-09-22 | 2022-04-26 | 陕西科技大学 | Polycarboxyl amphoteric Bola type surfactant and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1128267A (en) * | 1994-09-07 | 1996-08-07 | 希尔斯股份公司 | Process for preparing alkyglycosides |
| DE19645189A1 (en) * | 1996-11-02 | 1998-05-07 | Henkel Kgaa | Gemini surfactants |
| WO2006100091A1 (en) * | 2005-03-24 | 2006-09-28 | Beiersdorf Ag | Novel surfactants and novel emulsifiers made from disaccharides |
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2012
- 2012-09-21 CN CN201210356288.7A patent/CN102872752B/en not_active Expired - Fee Related
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| CN1128267A (en) * | 1994-09-07 | 1996-08-07 | 希尔斯股份公司 | Process for preparing alkyglycosides |
| DE19645189A1 (en) * | 1996-11-02 | 1998-05-07 | Henkel Kgaa | Gemini surfactants |
| WO2006100091A1 (en) * | 2005-03-24 | 2006-09-28 | Beiersdorf Ag | Novel surfactants and novel emulsifiers made from disaccharides |
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| Reactions of Oligoethylene Glycol Diglycidyl Ethers with Hydroxy Compounds;Yohji Nakatsuji等;《The Journal of Organic Chemistry》;19860131;第51卷(第1期);第81-87页 * |
| Yohji Nakatsuji等.Reactions of Oligoethylene Glycol Diglycidyl Ethers with Hydroxy Compounds.《The Journal of Organic Chemistry》.1986,第51卷(第1期),第81-87页. |
| 一些新型非离子表面活性剂的制备和应用;梁梦兰;《表面活性剂工业》;20001231(第04期);第1-7页 * |
| 张培成,程凯,吴宏宇,燕方龙.正辛基葡萄糖苷的合成及其性能.《沈阳化工学院学报》.1995,第9卷(第02期),第139-145页. * |
| 梁梦兰.一些新型非离子表面活性剂的制备和应用.《表面活性剂工业》.2000,(第04期),第1-7页. |
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| CN102872752A (en) | 2013-01-16 |
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