CN1651129A - Surface active agent alcohol ether glucoside and its preparation method - Google Patents
Surface active agent alcohol ether glucoside and its preparation method Download PDFInfo
- Publication number
- CN1651129A CN1651129A CN200410064576.0A CN200410064576A CN1651129A CN 1651129 A CN1651129 A CN 1651129A CN 200410064576 A CN200410064576 A CN 200410064576A CN 1651129 A CN1651129 A CN 1651129A
- Authority
- CN
- China
- Prior art keywords
- alcohol ether
- active agent
- surface active
- ether glucoside
- glucoside
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Saccharide Compounds (AREA)
Abstract
An alcohol-ether-glucoside as surfactant is prepared through acetalization reaction between emtrol polyoxyvinylether and glucose. Its advantages are high water solubility, surface activity, and resistance to hard water and alkali, and easy biodegradation.
Description
Technical field
The invention belongs to class non-ionic surface active agent and preparation method thereof, relate in particular to the fatty alcohol polyethenoxy ether class compound (be called for short: alcohol ether) and glucose generation acetalation prepare the alcohol ether glucoside novel surfactant.
Background technology
Also not about the report of alcohol ether glucoside and synthetic technology thereof, relevant knowledge is the preparation method and the application thereof of alkyl polyglycoside up to now.Alkyl polyglycoside is to react the product that makes by fatty alcohol and glucose under catalyst action, belongs to green surfactant.But the water-soluble and anti-hard water of the many glycosides of long alkyl chain length is undesirable, and especially alkyl chain length is greater than C
12Alkyl polyglycoside water-soluble poorer, this has limited the Application of alkyl polyglucosides field.Alcohol ether glucoside is owing to embedded the EO chain of certain adduction number between the sugar ring of alkyl chain and certain degree of polymerization, its water-soluble and anti-hard water can have remarkable improvement than alkyl polyglycoside, thereby have the dual premium properties of alcohol ether and alkyl polyglycoside concurrently, have application widely.
Summary of the invention
Alcohol ether) and the alcohol ether glucoside surfactant for preparing of glucose generation acetalation and preparation method thereof the purpose of this invention is to provide a kind of fatty alcohol polyethenoxy ether class compound (is called for short:.
Alcohol ether glucoside of the present invention is a class non-ionic surface active agent, and its molecular structural formula is:
In the said structure formula, R is C
8-18Aliphatic group; N be oxirane on average add and count (hereinafter to be referred as: the EO number), can be 0.1-3, preferably 0.3-1.5; M is a sugar ring average degree of polymerization, can be 1-5, preferably 1.2-1.8.
The synthetic method of alcohol ether glucoside of the present invention is represented with following reaction equation:
The concrete preparation method of the present invention comprises the steps:
(1) be in 1: 3～6 adding reactors with glucose and fatty alcohol polyethenoxy ether class compound by glucose and fatty alcohol polyethenoxy ether class compound mol ratio, at inert gas shielding, acid catalyst existence and system pressure is under the vacuum condition of 5-30mmHg, in 100～130 ℃ of reactions 3-4 hour, be cooled to 60～90 ℃ and add nertralizer, regulate most 7-9 of pH value, obtain containing the reactant mixture of alcohol ether glucoside and fatty alcohol polyethenoxy ether class compound;
(2) reactant mixture of alcohol ether glucoside and fatty alcohol polyethenoxy ether class compound is lower than under the vacuum condition of 2mmHg in 135～180 ℃ of temperature and system pressure, and unreacted fatty alcohol polyethenoxy ether class compound is removed in distillation, obtains the alcohol ether glucoside product.
Aforesaid acid catalyst can be an organic acid, as p-methyl benzenesulfonic acid, DBSA, ethylenediamine tetra-acetic acid etc.; Also can be inorganic acid, as sulfuric acid, hydrochloric acid, phosphoric acid etc.; Or inorganic acid and organic acid mixture.
Aforesaid nertralizer is alkaline earth oxide and alkali metal hydroxide mixture or single alkaline earth oxide.
The alcohol ether glucoside of the present invention's preparation can be used for laundry detergent, dish washing detergent, liquid detergent and bubble bath agent, hard surface cleaner, cosmetics and shampoo, sterilization and desinfactant detergent, paper industry auxiliary agent and washing agent, plastics industry additive, building industry auxiliary agent, food industry used additives and cleaning agent, agricultural-chemical emulsion and plant growth regulator and fields such as pesticide, viscosity modifier and foam stabiliser, for the ease of using, its using method is to use after alcohol ether glucoside is mixed with the aqueous solution.
Advantage of the present invention:
1. product has good water-solubility, resistance to hard water and alkaline-resisting stability, has the active and outstanding easily biological-degradable of surface of good simultaneously.
2. the preparation method adopts direct glucosides method, is very suitable for suitability for industrialized production.
The specific embodiment
Embodiment 1
With 0.8 mole of C
12-14AEO (the EO number is 0.5), 0.2 mole of DEXTROSE ANHYDROUS and DBSA 1.5g add in the reactor, stir and be heated to 100 ℃.At system pressure 25mmHg and 100 ℃ of following reaction 4hr, be cooled to 80 ℃, add the mixture 0.7g of MgO and NaOH, adjust pH to 8.Material is sent into the molecular clock evaporimeter, and at 140 ℃ of temperature conditions, system pressure 0.5mmHg deviates from 0.66 mole of unreacted free alcohol ether, the rate of recovery 98.5%; Obtain 0.129 mole of alcohol ether glucoside product, product yield 99.8%, sugar ring average degree of polymerization is 1.55.
Embodiment 2:
2M
3Add C in the reactor
12-163000 moles of fatty alcohol ethers (the EO number is 1), disposable adding～1000 moles of water glucose, Catalyzed by p-Toluenesulfonic Acid agent 1.8kg are stirred and the outer circulation pump in logical nitrogen, unlatching.At system pressure 15mmHg and 110 ℃ of following reaction 3.5hr, be cooled to 90 ℃, add the mixture 210g of MgO and NaOH, adjust pH to 8.5.Material is sent into film and is scraped and pull evaporimeter, and at 160～180 ℃ of temperature conditions, system pressure 1.8mmHg deviates from 2383.3 moles of unreacted free alcohol ethers, the rate of recovery 97.5%; Obtain 552.5 moles of alcohol ether glucoside products, product yield 99.5%, sugar ring average degree of polymerization is 1.8.
Embodiment 3:
2M
3Add C in the reactor
8-183000 moles of fatty alcohol ethers (the EO number is 1.5), logical nitrogen, unlatching are stirred and material outer circulation pump, add 600 moles of DEXTROSE ANHYDROUSs, p-methyl benzenesulfonic acid/phosphoric acid/ethylenediamine tetra-acetic acid mixed catalyst 1.2kg.At system pressure 10mmHg and 120 ℃ of following reaction 4hr, be cooled to 80 ℃, add MgO 270g, adjust pH to 7.Material is sent into the film scraper evaporator, and at 175～180 ℃ of temperature conditions, system pressure 0.7mmHg deviates from 2481.8 moles of unreacted free alcohol ethers, the rate of recovery 97.5%; Obtain 452.3 moles of alcohol ether glucoside products, product yield 99.5%, sugar ring average degree of polymerization is 1.32.
Embodiment 4:
With 0.9 mole of C
8-14AEO (the EO number is 2.5), 0.15 mole of DEXTROSE ANHYDROUS and catalyst concentrated sulfuric acid 0.1g.At system pressure 5mmHg and 130 ℃ of following reaction 3hr, be cooled to 80 ℃, add the mixture 0.5g of MgO and NaOH, adjust pH to 8.5.Material is sent into the molecular clock evaporimeter, and at 150 ℃ of temperature conditions, system pressure 0.3mmHg deviates from 0.778 mole of unreacted free alcohol ether, the rate of recovery 99.8%; Obtain 0.12 mole of alcohol ether glucoside product, product yield 100%, sugar ring average degree of polymerization is 1.25.
Embodiment 5:
With 0.8 mole of C
8-14AEO (the EO number is 0.3), 0.2 mole of DEXTROSE ANHYDROUS and Catalyzed by p-Toluenesulfonic Acid agent 0.36g.At system pressure 30mmHg and 120 ℃ of following reaction 4hr, be cooled to 90 ℃, add the mixture 0.6g of MgO and NaOH, adjust pH to 8.Material is sent into the molecular clock evaporimeter, and at 135 ℃ of temperature conditions, system pressure 0.6mmHg deviates from 0.66 mole of unreacted free alcohol ether, the rate of recovery 99.1%; Obtain 0.134 mole of alcohol ether glucoside product, product yield 99.8%, sugar ring average degree of polymerization is 1.49.
Claims (8)
1, a kind of surface active agent alcohol ether glucoside is characterized in that alcohol ether glucoside is a class non-ionic surface active agent, and its molecular structural formula is:
Wherein R is C
8-18Aliphatic group; N is that oxirane on average adds and counts, and is 0.1-3, and m is a sugar ring average degree of polymerization, is 1-5.
2, a kind of surface active agent alcohol ether glucoside as claimed in claim 1 is characterized in that described n is 0.3-1.5.
3, a kind of surface active agent alcohol ether glucoside as claimed in claim 1 is characterized in that described m is 1.2-1.8.
4,, it is characterized in that comprising the steps: as the preparation method of each described a kind of surface active agent alcohol ether glucoside of claim 1-3
(1) be in 1: 3～6 adding reactors with glucose and fatty alcohol polyethenoxy ether class compound by glucose and fatty alcohol polyethenoxy ether class compound mol ratio, at inert gas shielding, acid catalyst existence and system pressure is under the vacuum condition of 5-30mmHg, in 100～130 ℃ of reactions 3-4 hour, be cooled to 60～90 ℃ and add nertralizer, regulate most 8-9 of pH value, obtain containing the reactant mixture of alcohol ether glucoside and fatty alcohol polyethenoxy ether class compound;
(2) reactant mixture of alcohol ether glucoside and fatty alcohol polyethenoxy ether class compound is lower than under the vacuum condition of 2mmHg in 135～180 ℃ of temperature and system pressure, and unreacted fatty alcohol polyethenoxy ether class compound is removed in distillation, obtains the alcohol ether glucoside product.
5, the preparation method of a kind of surface active agent alcohol ether glucoside as claimed in claim 4 is characterized in that described acid catalyst is organic acid and/or inorganic acid.
6, the preparation method of a kind of surface active agent alcohol ether glucoside as claimed in claim 5 is characterized in that described organic acid is p-methyl benzenesulfonic acid, DBSA or ethylenediamine tetra-acetic acid.
7, the preparation method of a kind of surface active agent alcohol ether glucoside as claimed in claim 5 is characterized in that described inorganic acid is sulfuric acid, hydrochloric acid or phosphoric acid;
8, the preparation method of a kind of surface active agent alcohol ether glucoside as claimed in claim 4 is characterized in that described nertralizer is alkaline earth oxide and alkali metal hydroxide mixture or single alkaline earth oxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100645760A CN100341612C (en) | 2004-11-30 | 2004-11-30 | Surface active agent alcohol ether glucoside and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100645760A CN100341612C (en) | 2004-11-30 | 2004-11-30 | Surface active agent alcohol ether glucoside and its preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1651129A true CN1651129A (en) | 2005-08-10 |
| CN100341612C CN100341612C (en) | 2007-10-10 |
Family
ID=34868855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100645760A Expired - Fee Related CN100341612C (en) | 2004-11-30 | 2004-11-30 | Surface active agent alcohol ether glucoside and its preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100341612C (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100451027C (en) * | 2006-10-24 | 2009-01-14 | 中国日用化学工业研究院 | Process for preparing modified fatty alcohol polyethenoxy ether |
| CN100455618C (en) * | 2006-07-19 | 2009-01-28 | 大连理工大学 | Polyether glucoside ester large molecule compound and its preparation method |
| CN104017034A (en) * | 2014-06-03 | 2014-09-03 | 中国科学院过程工程研究所 | Method for separating and purifying alkylethoxyglucoside |
| CN104194968A (en) * | 2014-09-19 | 2014-12-10 | 江苏万淇生物科技有限公司 | Washing product containing AEG (Alkyl Ethoxy Polyglycosides) for hand washing dishes |
| CN104194963A (en) * | 2014-09-19 | 2014-12-10 | 江苏万淇生物科技有限公司 | Highly-concentrated enzyme-containing liquid detergent free of enzyme stabilizer |
| CN104257524A (en) * | 2014-09-19 | 2015-01-07 | 江苏万淇生物科技有限公司 | Shampoo containing alkyl ethoxy polyglycosides |
| CN104323925A (en) * | 2014-09-29 | 2015-02-04 | 江苏万淇生物科技有限公司 | Bath lotion being green, environmental-protective and gentle and containing glucoside derivative |
| CN104434556A (en) * | 2014-11-11 | 2015-03-25 | 上海万淇生物科技有限公司 | Hand sanitizer containing glucoside and derivatives of glucoside |
| CN105669786A (en) * | 2015-12-29 | 2016-06-15 | 河北合佳医药科技集团有限公司 | Method and production apparatus for continuously producing alkyl ethoxy polyglycoside |
| CN105713052A (en) * | 2016-01-19 | 2016-06-29 | 威尔（福建）生物有限公司 | Polyether glucoside sulfonate, preparation method and application thereof and herbicide |
| CN106359445A (en) * | 2016-08-04 | 2017-02-01 | 四川利尔作物科学有限公司 | Weeding composition and application thereof |
| CN106422965A (en) * | 2016-09-14 | 2017-02-22 | 中国海洋大学 | Synthetic method of chitosan surface active agent for improving morphology and dispersibility of ferroferric oxide |
| CN107648061A (en) * | 2017-10-17 | 2018-02-02 | 中国日用化学工业研究院 | A kind of shampoo with anti-dandruff nourishing pearly-lustre and preparation method thereof |
| CN107722143A (en) * | 2017-11-02 | 2018-02-23 | 山东广浦生物科技有限公司 | A kind of preparation method and fracturing fluid system of alcohol ether modified guar |
| CN107789898A (en) * | 2017-11-06 | 2018-03-13 | 偃师然合生物材料有限公司 | A kind of water reducer of molecular screen primary powder |
| CN108610478A (en) * | 2018-04-04 | 2018-10-02 | 广州顺润新材料科技有限公司 | A kind of fluorine-containing alkyl glycosides and its preparation method and application |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146649A (en) * | 1976-10-14 | 1979-03-27 | Faberge, Incorporated | Skin moisturizing composition containing a polyethoxy fatty alcohol and a polyethoxy glycoside |
| US4528106A (en) * | 1983-11-14 | 1985-07-09 | Olin Corporation | Glucoside surfactants |
| DE3723826A1 (en) * | 1987-07-18 | 1989-01-26 | Henkel Kgaa | METHOD FOR PRODUCING ALKYL GLYCOSIDES |
| CN1045261C (en) * | 1992-04-12 | 1999-09-29 | 轻工业部日用化学工业科学研究所 | Prepn. method of alkyl glucoside surfactant |
| DE19859911A1 (en) * | 1998-12-23 | 2000-06-29 | Basf Ag | Process for the preparation of surfactant alcohols and surfactant alcohol ethers, the products produced and their use |
-
2004
- 2004-11-30 CN CNB2004100645760A patent/CN100341612C/en not_active Expired - Fee Related
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100455618C (en) * | 2006-07-19 | 2009-01-28 | 大连理工大学 | Polyether glucoside ester large molecule compound and its preparation method |
| CN100451027C (en) * | 2006-10-24 | 2009-01-14 | 中国日用化学工业研究院 | Process for preparing modified fatty alcohol polyethenoxy ether |
| CN104017034A (en) * | 2014-06-03 | 2014-09-03 | 中国科学院过程工程研究所 | Method for separating and purifying alkylethoxyglucoside |
| CN104017034B (en) * | 2014-06-03 | 2016-08-24 | 中国科学院过程工程研究所 | A kind of method that alcohol ether glucoside is isolated and purified |
| CN104257524A (en) * | 2014-09-19 | 2015-01-07 | 江苏万淇生物科技有限公司 | Shampoo containing alkyl ethoxy polyglycosides |
| CN104194963B (en) * | 2014-09-19 | 2017-07-07 | 江苏万淇生物科技有限公司 | Highly enriched liquid detergent containing enzyme without enzyme stabilizers |
| CN104194963A (en) * | 2014-09-19 | 2014-12-10 | 江苏万淇生物科技有限公司 | Highly-concentrated enzyme-containing liquid detergent free of enzyme stabilizer |
| CN104194968A (en) * | 2014-09-19 | 2014-12-10 | 江苏万淇生物科技有限公司 | Washing product containing AEG (Alkyl Ethoxy Polyglycosides) for hand washing dishes |
| CN104323925A (en) * | 2014-09-29 | 2015-02-04 | 江苏万淇生物科技有限公司 | Bath lotion being green, environmental-protective and gentle and containing glucoside derivative |
| CN104434556A (en) * | 2014-11-11 | 2015-03-25 | 上海万淇生物科技有限公司 | Hand sanitizer containing glucoside and derivatives of glucoside |
| CN104434556B (en) * | 2014-11-11 | 2017-10-03 | 江苏万淇生物科技有限公司 | A kind of hand cleanser containing glucosides and its derivative |
| CN105669786A (en) * | 2015-12-29 | 2016-06-15 | 河北合佳医药科技集团有限公司 | Method and production apparatus for continuously producing alkyl ethoxy polyglycoside |
| CN105669786B (en) * | 2015-12-29 | 2018-12-18 | 河北合佳医药科技集团有限公司 | The method of continuous production alcohol ether glucoside |
| CN105713052A (en) * | 2016-01-19 | 2016-06-29 | 威尔（福建）生物有限公司 | Polyether glucoside sulfonate, preparation method and application thereof and herbicide |
| CN105713052B (en) * | 2016-01-19 | 2019-01-04 | 威尔（福建）生物有限公司 | A kind of polyether glucoside sulfonate and preparation method thereof, using and a kind of herbicide |
| CN106359445B (en) * | 2016-08-04 | 2018-07-24 | 四川利尔作物科学有限公司 | Herbicidal combinations and its application |
| CN106359445A (en) * | 2016-08-04 | 2017-02-01 | 四川利尔作物科学有限公司 | Weeding composition and application thereof |
| CN106422965A (en) * | 2016-09-14 | 2017-02-22 | 中国海洋大学 | Synthetic method of chitosan surface active agent for improving morphology and dispersibility of ferroferric oxide |
| CN107648061A (en) * | 2017-10-17 | 2018-02-02 | 中国日用化学工业研究院 | A kind of shampoo with anti-dandruff nourishing pearly-lustre and preparation method thereof |
| CN107648061B (en) * | 2017-10-17 | 2020-09-22 | 中国日用化学工业研究院 | Shampoo with dandruff removing, nourishing and pearly luster and preparation method thereof |
| CN107722143A (en) * | 2017-11-02 | 2018-02-23 | 山东广浦生物科技有限公司 | A kind of preparation method and fracturing fluid system of alcohol ether modified guar |
| CN107789898A (en) * | 2017-11-06 | 2018-03-13 | 偃师然合生物材料有限公司 | A kind of water reducer of molecular screen primary powder |
| CN108610478A (en) * | 2018-04-04 | 2018-10-02 | 广州顺润新材料科技有限公司 | A kind of fluorine-containing alkyl glycosides and its preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100341612C (en) | 2007-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100341612C (en) | Surface active agent alcohol ether glucoside and its preparation method | |
| EP2308881B1 (en) | Isosorbide-derivatives | |
| EP1519907B1 (en) | An alkoxylate mixture and its use as a cleaning agent for hard surfaces | |
| CZ289126B6 (en) | Process for preparing alkyl polyglucosides | |
| US20110288322A1 (en) | Derivatives of tris(2-hydroxyphenyl)methane, their preparation and use | |
| US5166337A (en) | Process for the preparation of carbohydrate surfactants | |
| CN104769091A (en) | Nonionic surfactant and method for producing nonionic surfactant | |
| US7241875B2 (en) | Method for the production of surface active agent mixtures | |
| CN105130798A (en) | Novel synthetic method for F-acrylic acid and derivative thereof | |
| AU2004281952B2 (en) | C10 alkanolalkoxylate mixtures and use thereof as novel low-foaming wetting agents | |
| US4894485A (en) | Alkaline earth metal salts of ether carboxylic acids as alkoxylation catalysts | |
| CA2797286C (en) | Derivatives of tris(2-hydroxyphenyl)methane, their preparation and use | |
| KR20000010805A (en) | Alkyl polyglycoside ether carboxylates | |
| CN100451027C (en) | Process for preparing modified fatty alcohol polyethenoxy ether | |
| CN1634949A (en) | Process for preparing light color transparent alkyl glycoside | |
| CA1338277C (en) | Process for the production of terminally blocked polyglycol ethers | |
| US6156885A (en) | Process for the synthesis of alkylpolyglucosides | |
| CN100455618C (en) | Polyether glucoside ester large molecule compound and its preparation method | |
| US5502175A (en) | Fatty acid esters of methylglucoside derivatives | |
| CN1030700C (en) | Process for making alkyl ethoxy carboxylates | |
| DE69830486T2 (en) | ALUMINUM COMPOUNDS AND THEIR USE | |
| US6028229A (en) | Process for producing end-group-locked non-ionic tensides | |
| US20240059973A1 (en) | Capped alkoxylated alcohols | |
| US5898070A (en) | Process for the production of alkyl and/or alkenyl oligoglycosides | |
| US5545731A (en) | Alkyl and/or alkenyl oligoglycoside carbonates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20071010 Termination date: 20191130 |