CN102643312A - Isomeric primary alcohol alkyl glycoside and synthesis method and application thereof - Google Patents
Isomeric primary alcohol alkyl glycoside and synthesis method and application thereof Download PDFInfo
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- CN102643312A CN102643312A CN2012101210120A CN201210121012A CN102643312A CN 102643312 A CN102643312 A CN 102643312A CN 2012101210120 A CN2012101210120 A CN 2012101210120A CN 201210121012 A CN201210121012 A CN 201210121012A CN 102643312 A CN102643312 A CN 102643312A
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Abstract
The invention belongs to the technical field of a fine chemical industry surfactant. The synthesis method of alkyl glycoside is generally a transglycosylation method, which utilizes the exchange of low-carbon alcohol and high-carbon alcohol to synthesize required alkyl glycoside, so that glucoside containing low-carbon alcohol in the final product is usually butyl glycoside, and the purity and surface activity of the product are greatly reduced and the product generates peculiar smell due to the existence of butyl glycoside. The invention aims at providing an isomeric primary alcohol alkyl glycoside, and a synthesis method and application of the isomeric primary alcohol alkyl glycoside. According to the invention, the isomeric primary alcohol alkyl glycoside is synthesized by a direct glycosidation method. The method is concise and few in subsidiary reactions, and the product is high in active matter content. The synthesized isomeric primary alcohol alkyl glycoside has the advantages of low bubble, good wetting property, strong dispersing and decontamination capability and the like.
Description
Technical field
The invention belongs to the fine chemistry industry technical field of surfactant, be specifically related to a kind of isomery primary alconol APG and compound method and application.
Background technology
APG is that the verivate glucose and the Fatty Alcohol(C12-C14 and C12-C18) of renewable resources starch is that raw material carries out synthetic; Because thorough rapidly, the nontoxic non-stimulated era development trend that meets modern society's " green ", " environmental protection " of its biological degradation; The performance of good in addition Surfactant, so it is called the tensio-active agent kind of " world-class " by industry.Domesticly begun large-scale production at present.
The compound method of APG generally is to change the glucosides method; The patent No. is CN95116215.2; Publication number is CN1128268; Denomination of invention discloses the method for changeing glucosides technology synthesizing alkyl polyglycoside for " preparation method of alkyl oligoglycosides ", the technology of changeing the glucosides synthesizing alkyl polyglycoside be utilize low-carbon alcohol and higher alcohols exchange come synthetic need APG, so the glucosides that can cause in final product, containing low-carbon alcohol fourth glycosides normally; And the existence of fourth glycosides can cause product gas purity and surfactivity to reduce greatly, can make product produce peculiar smell simultaneously.
Summary of the invention
The purpose of this invention is to provide a kind of isomery primary alconol APG, another object of the present invention provides the compound method of isomery primary alconol APG, and the 3rd purpose of the present invention provides the application of isomery primary alconol APG in the preparation tensio-active agent.
The inventor is in secular nonionogenic tenside research, and a kind of isomery primary alconol APG of imagination preparation is because its special isomery primary alconol structure as oleophilic group, has good low bubble performance and alkali resistance with making it.Compare with the straight chain primary aliphatic alcohols, because the oleophilic group structure of its isomery primary alcohol group, make it on physical and chemical performances such as surface tension, wetting, micelle-forming concentration, to be superior to the straight chain primary alcohol APG.And usually in the industrial production requirement to clean-out system be that good wettability will be arranged under the alkaline environment, low bubble property, soil removability are strong etc., these special performances will be that isomery primary alconol APG has.
Technical scheme of the present invention mainly is to come synthesising different structure primary alconol APG with direct glycosidation method; With the isomery primary alconol; Glucose is raw material, is catalyzer with Louis (lewis) acid, and glucose can lose a part water under an acidic catalyst existence condition; Form carbonium ion, and then form the isomery primary alconol APG that stable acetal promptly generates thick product with the isomery primary alconol effect of a part.
Isomery primary alconol APG dealcoholysis under certain pressure and temperature of thick product is floated look with a certain amount of ydrogen peroxide 50 then and is promptly obtained isomery primary alconol APG.
The invention provides a kind of compound method of isomery primary alconol APG, this method is a raw material with isomery primary alconol, glucose, is catalyzer with lewis acid, and glucose forms acetal with the isomery primary alconol and promptly generates APG under the lewis acid catalysis.
Described isomery primary alconol is specially isomery uncle hexanol, isomery uncle octanol, isomery uncle decyl alcohol, isomery uncle tridecanol, isomery uncle's hexadecanol or isomery uncle stearyl alcohol etc., and described isomery primary alconol be configured as S type, R type or S, R mixed type;
The mol ratio of described isomery primary alconol and glucose is 3: 1～7: 1;
The mass ratio of described Lewis acid and glucose is 1: 200～1: 50.
Described glucose is anhydrous glucose of≤100 purposes or DEXTROSE MONOHYDRATE BP.
Described lewis acid is specially tosic acid, Witco 1298 Soft Acid etc.
Described anhydrous glucose or DEXTROSE MONOHYDRATE BP are 4.0～7.0 hours with reaction times that the isomery primary alconol forms acetal (glycosidation) under the lewis acid catalysis.
Described anhydrous glucose or DEXTROSE MONOHYDRATE BP are that residual voltage is not less than 20mmHg with reaction pressure that the isomery primary alconol forms acetal (glycosidation) under the lewis acid catalysis.
Described anhydrous glucose or DEXTROSE MONOHYDRATE BP are 112～118 ℃ with temperature of reaction that the isomery primary alconol forms acetal (glycosidation) under the lewis acid catalysis.
The isomery primary alconol APG that aforesaid method obtains is thick product; Further method of purification is following: at pressure condition is that vacuum is less than 5mmHg; Temperature condition is 150-180 ℃ of following dealcoholysis; Use ydrogen peroxide 50 to float look then, promptly obtain the isomery primary alconol APG of purifying with respect to APG solution quality 1～5%.
Reaction formula is following:
R1 wherein, R2 represents straight chain or contains the alkyl of isomery, and the C number that R1, R2 contain is 2～15.
Compound method of the present invention is compared with traditional commentaries on classics glucosides method, and have the following advantages: technical process is more succinct, and side reaction is few etc.Therefore high with direct glycosidation method synthesizing alkyl polyglycoside technical value added of the present invention, the product active matter content is high.
The invention provides according to aforesaid method synthetic isomery primary alconol APG.
Synthetic isomery primary alconol APG of the present invention is compared with traditional straight chained alkyl glucosides has outstanding advantage: compare with the APG of same carbon number, isomery primary alconol APG of the present invention has low bubble, and wettability is good, disperses advantages such as soil removability is strong.
The present invention also provides the application of isomery primary alconol APG in the preparation tensio-active agent.
Therefore isomery primary alconol synthetic APG can be widely used in weaving, printing and dyeing, leather, fiber, particularly industrial washing field; The isomery primary alconol APG that the present invention obtains is one type of novel nonionogenic tenside; Have good wettability, lyotropy, alkali resistance; Can be used as in industrial cleaning agent, in that it has demonstrated good alkali resistance, low spumescence aspect the industry cleaning, development prospect is very wide.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should understand these embodiment and only be used to explain the present invention, and be not used in restriction range of application of the present invention.
Instance 1: isomery uncle decyl alcohol APG
In reaction kettle, add 1.14 moles isomery uncle's decyl alcohol and 0.32 mole dextrose anhydrous, at the Witco 1298 Soft Acid that adds 0.58 gram, begin to heat up after having checked the stopping property of device, stir speed (S.S.) is more than 840r/min.Within 20 minutes, temperature is elevated to 115 ℃ (± 2 ℃), regulating pressure is residual voltage 30mmHg.React qualified products after 5.5 hours, obtain isomery uncle decyl alcohol APG through dealcoholation treatment.
Finished product is handled: at pressure condition is that residual voltage is less than 5mmHg; Temperature condition is 180 ℃ of following dealcoholysis; With product with deionized water dissolving after the preparation 51.0% solution, use ydrogen peroxide 50 to float look then with respect to APG solution quality 2%, promptly obtain the isomery primary alconol APG of purifying.
Instance 2: isomery uncle octanol APG
In reaction kettle, add 1.47 moles isomery uncle's octanol and 0.28 mole dextrose anhydrous, at the Witco 1298 Soft Acid that adds 0.5 gram, begin to heat up after having checked the stopping property of device, stir speed (S.S.) is more than 840r/min.Within 20 minutes, temperature is elevated to 113 ℃ (± 2 ℃).Regulating pressure is residual voltage 40mmHg.React qualified products after 5 hours, obtain isomery uncle octanol APG through dealcoholation treatment.
Finished product is handled: at pressure condition is that residual voltage is less than 5mmHg; Temperature condition is 150 ℃ of following dealcoholysis; With product with deionized water dissolving after the preparation 51.0% solution, use ydrogen peroxide 50 to float look then with respect to APG solution quality 1.5%, promptly obtain the isomery primary alconol APG of purifying.
The performance test of instance 3: embodiment 1 and 2 synthetic isomery primary alconol APGs
The straight chained alkyl glucosides of preparation and embodiment 1 and 2 same carbon number, reaction process is following:
R representes the C6-18 alkyl in the following formula, and G represents the sugar unit number, and n representes is bonded sugar unit number or be called mean polymerisation degree on each alkyl.
LAS is a Witco 1298 Soft Acid.
Surface tension (mN/m), experimental technique is referring to GB/T 22237-2008
Wettability (s), experimental technique is referring to GB/11983-2008
Viscosity (mPa.s), experimental technique is referring to GB/15357-94 (measuring temperature usually is 20 ℃, when viscosity during greater than 10000mPa.s, measures temperature and should rise to 40 ℃)
Foam power (mm) 30s, 3min, 5min, experimental technique is referring to GB/T 7462-94
Isomery uncle's decyl alcohol APG and straight chain decyl alcohol APG performance comparison result see table 1 for details, and isomery uncle's octanol APG and straight chain octanol APG performance comparison result see table 2 for details.
Table 1: isomery uncle's decyl alcohol APG and straight chain decyl alcohol APG performance comparison
Table 2: isomery uncle's octanol APG and straight chain octanol APG performance comparison
Visible by table 1 and table 2, to compare with the straight chained alkyl glucosides of same carbon number, it is low that isomery primary alconol APG of the present invention has surface tension, low bubble, wettability is good, advantages such as good fluidity.
Claims (10)
1. an isomery primary alconol APG is characterized in that, this isomery primary alconol APG is according to following method synthetic:
With isomery primary alconol, glucose is raw material, is catalyzer with the Lewis acid, and glucose forms acetal with the isomery primary alconol under Louis acid catalysis, promptly generate isomery primary alconol APG;
Described isomery primary alconol is isomery uncle hexanol, isomery uncle octanol, isomery uncle decyl alcohol, isomery uncle tridecanol, isomery uncle's hexadecanol or isomery uncle stearyl alcohol, and described isomery primary alconol be configured as S type, R type or S, R mixed type;
The mol ratio of described isomery primary alconol and glucose is 3: 1～7: 1;
The mass ratio of described Lewis acid and glucose is 1: 200～1: 50.
2. the compound method of an isomery primary alconol APG as claimed in claim 1; It is characterized in that this method is to be raw material with isomery primary alconol, glucose, is catalyzer with the Lewis acid; Glucose forms acetal with the isomery primary alconol under Louis acid catalysis, promptly generate isomery primary alconol APG;
Described isomery primary alconol is isomery uncle hexanol, isomery uncle octanol, isomery uncle decyl alcohol, isomery uncle tridecanol, isomery uncle's hexadecanol or isomery uncle stearyl alcohol, and described isomery primary alconol be configured as S type, R type or S, R mixed type;
The mol ratio of described isomery primary alconol and glucose is 3: 1～7: 1;
The mass ratio of described Lewis acid and glucose is 1: 200～1: 50.
3. the compound method of a kind of isomery primary alconol APG according to claim 2 is characterized in that, described glucose is≤100 purpose dextrose anhydrous or DEXTROSE MONOHYDRATE BPs.
4. the compound method of a kind of isomery primary alconol APG according to claim 2 is characterized in that, described Lewis acid is tosic acid or Witco 1298 Soft Acid.
5. the compound method of a kind of isomery primary alconol APG according to claim 2 is characterized in that, described dextrose anhydrous or DEXTROSE MONOHYDRATE BP are 4.0～7.0 hours with reaction times that the isomery primary alconol forms acetal under Louis acid catalysis.
6. the compound method of a kind of isomery primary alconol APG according to claim 2 is characterized in that, described dextrose anhydrous or DEXTROSE MONOHYDRATE BP are that residual voltage is not less than 20mmHg with reaction pressure that the isomery primary alconol forms acetal under Louis acid catalysis.
7. the compound method of a kind of isomery primary alconol APG according to claim 2 is characterized in that, described dextrose anhydrous or DEXTROSE MONOHYDRATE BP are 112～118 ℃ with temperature of reaction that the isomery primary alconol forms acetal under Louis acid catalysis.
8. the compound method of a kind of isomery primary alconol APG according to claim 2; It is characterized in that; Described dextrose anhydrous or DEXTROSE MONOHYDRATE BP form after the acetal with the isomery primary alconol under Louis acid catalysis, further purify: pressure condition be residual voltage less than 5mmHg, temperature condition is 150-180 ℃ of following dealcoholysis; Use ydrogen peroxide 50 to float look then, promptly obtain the isomery primary alconol APG of purifying with respect to APG solution quality 1～5%.
9. the compound method of a kind of isomery primary alconol APG according to claim 8 is characterized in that, during purification, pressure condition is that residual voltage is less than 5mmHg.
10. the application of isomery primary alconol APG as claimed in claim 1 in the preparation tensio-active agent.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105218603A (en) * | 2015-10-14 | 2016-01-06 | 上海大学 | The subcritical alcoholysis starch of isooctyl alcohol is adopted to prepare the method for alkyl glucoside surfactant |
| CN109939612A (en) * | 2019-03-11 | 2019-06-28 | 上海发凯化工有限公司 | Guerbet alcohol alkyl glucoside surfactant and preparation method thereof |
| CN111304017A (en) * | 2020-03-24 | 2020-06-19 | 万华化学集团股份有限公司 | Mild low-foam washing gel bead and preparation method thereof |
| CN113683652A (en) * | 2021-09-16 | 2021-11-23 | 上海发凯化工有限公司 | Preparation method and application of aromatic alcohol alkyl glycoside |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105218603A (en) * | 2015-10-14 | 2016-01-06 | 上海大学 | The subcritical alcoholysis starch of isooctyl alcohol is adopted to prepare the method for alkyl glucoside surfactant |
| CN105218603B (en) * | 2015-10-14 | 2018-05-01 | 上海大学 | The method that alkyl glucoside surfactant is prepared using the subcritical alcoholysis starch of isooctanol |
| CN109939612A (en) * | 2019-03-11 | 2019-06-28 | 上海发凯化工有限公司 | Guerbet alcohol alkyl glucoside surfactant and preparation method thereof |
| CN111304017A (en) * | 2020-03-24 | 2020-06-19 | 万华化学集团股份有限公司 | Mild low-foam washing gel bead and preparation method thereof |
| CN113683652A (en) * | 2021-09-16 | 2021-11-23 | 上海发凯化工有限公司 | Preparation method and application of aromatic alcohol alkyl glycoside |
| CN113683652B (en) * | 2021-09-16 | 2023-12-01 | 上海发凯化工有限公司 | Preparation method and application of aromatic alcohol alkyl glycoside |
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Application publication date: 20120822 |