CN105061523A - Method for synthesizing alkyl glycoside based on microwave radiation - Google Patents
Method for synthesizing alkyl glycoside based on microwave radiation Download PDFInfo
- Publication number
- CN105061523A CN105061523A CN201510564250.2A CN201510564250A CN105061523A CN 105061523 A CN105061523 A CN 105061523A CN 201510564250 A CN201510564250 A CN 201510564250A CN 105061523 A CN105061523 A CN 105061523A
- Authority
- CN
- China
- Prior art keywords
- alkyl glycoside
- fatty alcohol
- glucose
- reaction time
- warming
- 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.)
- Pending
Links
Landscapes
- Saccharide Compounds (AREA)
Abstract
The invention relates to a method for synthesizing alkyl glycoside based on microwave radiation. According to the method, the disadvantages of long reaction time and complex synthetic process in most existing alkyl glycoside synthesis methods are solved. The method comprises the following steps: adding fatty alcohol and glucose into a polytetrafluoroethylene tube, setting intensity of pressure at 0.4MPa-0.7MPa, heating to 70-110 DEG C, and reacting at 110 DEG C by utilizing p-toluenesulfonic acid as a catalyst; after the reaction, regulating the pH of a system at 7-8, transferring reactants into a reduced pressure distillation device, heating to 110-150 DEG C, carrying out reduced pressure distillation at the absolute pressure of 1KPa so as to obtain crude alkyl glycoside, and carrying out separation and purification, so as to obtain a refined alkyl glycoside surfactant. By virtue of a microwave synthesis method, the method has the excellent characteristics of short reaction time, high yield and high efficiency; by taking p-toluenesulfonic acid as the catalyst, the reaction velocity between glucose and fatty alcohol is increased, and the reaction time is further shortened; and the synthetic route is simple, and the reaction time can be shortened to be 3-10 minutes.
Description
Technical field
The present invention relates to a kind of synthetic method of alkyl glycoside, be specifically related to a kind of method based on microwave irradiation synthesis alkyl glycoside.
Background technology
Alkyl glycoside (alkylpolyglucoside, APG for short) is by starch or its hydrolysate---glucose and fatty alcohol in acid condition condensation lose a part water and the product obtained, and are the nonionogenic tensides of a class green.Alkyl glycoside has the performances such as good emulsifying, dispersion, solubilising, decontamination, foam is fine and smooth and stable, there is not reverse cloud point, there is good high-temperature stability, interfacial tension is low, has good washing force, good with other types tensio-active agent compatibleness, gentle, nontoxic, readily biodegradable, has been widely used in multiple fields such as makeup, washing product, agricultural, industry, oil and biology.Especially the green of its raw material is renewable, the Atom economy of preparation process, and can complete biodegradable, is called " world-class " green surfactant by domestic and international expert.
Direct glycosidation method is one of the most frequently used synthetic method adopted now, and have that synthetic thread is short out, the reaction times is short, energy consumption is little, cost is low and the advantage such as convenient operation, but the product composition of synthesis is more complicated, refining comparatively difficulty.Turn the synthetic method that glycosylation method is another kind of conventional alkyl glycoside, its advantage is that reaction conditions is gentle, and building-up process is easy to control.But compared with direct method, its synthetic route is longer, also need in process to be separated the low-carbon alcohol introduced, and need carry out under explosion-proof condition, production cost is high.Direct glycosidation method and a turn glycosylation fado adopt organic acid to be catalyzer, and these acid are to equipment existence corrosion in various degree and the problem of environmental pollution.Also have report to adopt some efficient catalyzer, but these catalyzer costs are higher, and not easily obtain.
Enzyme catalyzed synthesis alkyl glycoside method has the advantage of specificity, high efficiency, utilizes this method to prepare alkyl glycoside and has very large economic benefit.But enzymatic clarification is relatively harsh to requirement for environmental conditions, be difficult to carry out industrialization promotion.Koenigs – Knorr method is simple, and product yield is higher, is easy to purification & isolation, but the catalyzer price used in its building-up process is more expensive, and synthesis cost is high, is not suitable for scale production.Tin tetrachloride method synthesizing alkyl polyglycoside has selectivity more better than additive method, generally generates β-glucosides more, and with the rising of temperature or the prolongation of time, β-glucosides can change into the more stable α-glucosides of thermodynamics.But this method need use a large amount of organic solvents, and the productive rate of product is general lower.
Add compared with thermal synthesis with traditional, it is short that microwave process for synthesizing has the reaction times, the feature that output is high and selectivity is excellent, now become investigator and improved classical organic reaction and one of prefered method promoting new synthesis.Compare and traditional add thermal synthesis method, Microwave-assisted synthesis method is a kind of environmentally friendly novel synthesis.In synthesizing alkyl polyglycoside process, have stronger controllability and high efficiency, be a kind of synthetic method of most research and extension prospect.
Summary of the invention
The object of this invention is to provide a kind of method based on microwave irradiation synthesis alkyl glycoside, overcome the shortcoming such as existing synthetic method long reaction time, building-up process complexity.
The technical solution adopted in the present invention is:
Based on the method for microwave irradiation synthesis alkyl glycoside, it is characterized in that:
Realized by following steps:
Step one: getting molfraction is that the fatty alcohol of 3 ~ 7 parts and the glucose of 1 part join in polyfluortetraethylene pipe, the tosic acid adding glucose quality 0.6 ~ 0.8% is catalyzer, arranging pressure is 0.4 ~ 0.7MPa, 1 ~ 3min is warming up to 70 DEG C, then 1 ~ 3min is warming up to 110 DEG C, at 110 DEG C, react 3 ~ 7min;
Step 2: after reaction terminates, regulation system pH to 7 ~ 8, then by reactant transfer in vacuum distillation apparatus, raised temperature to 110 ~ 150 DEG C, absolute pressure is 1KPa, and underpressure distillation obtains alkyl glycoside coarse product, the alkyl glucoside surfactant must refined after separating-purifying.
In step one, fatty alcohol is C
8~ C
16-OH.
In step 2, regulation system pH adopts volumetric molar concentration to be the NaOH solution of 1mol/L.
The present invention has the following advantages:
The present invention utilizes microwave process for synthesizing, has the reaction times short, and the excellent characteristics of the high and high efficiency of output take tosic acid as catalyzer, accelerates the speed of reaction of glucose and fatty alcohol, and then Reaction time shorten.This method can not produce pollution, is a kind of environmentally friendly novel synthesis.In synthesizing alkyl polyglycoside process, have stronger controllability and high efficiency, be a kind of synthetic method of most research and extension prospect.
The alkyl glycoside excellent property prepared according to preparation method of the present invention, and synthetic route is simple, particularly contrasting traditional method reaction times is greater than 4h, use microwave dissolver that the reaction times can be made to foreshorten to 3 ~ 10min, present invention improves existing alkyl glucoside surfactant and prepare Problems existing, long reaction time, synthesis is complicated with treating process, the situation that reaction efficiency is not high.
Embodiment
Below in conjunction with embodiment, the present invention will be described in detail.
The method based on microwave irradiation synthesis alkyl glycoside that the present invention relates to, for the problem of catalyzer in synthesis, attempt using tosic acid cheap and easy to get to be catalyzer, with microwave dissolver concerted catalysis synthesizing alkyl polyglycoside, its advantage is that microwave heating has very strong penetration, greatly can improve speed of response.Specifically realized by following steps:
Step one: getting molfraction is that the fatty alcohol of 3 ~ 7 parts and the glucose of 1 part join in polyfluortetraethylene pipe, the tosic acid adding glucose quality 0.6 ~ 0.8% is catalyzer, arranging pressure is 0.4 ~ 0.7MPa, 1 ~ 3min is warming up to 70 DEG C, then 1 ~ 3min is warming up to 110 DEG C, at 110 DEG C, react 3 ~ 7min;
Step 2: after reaction terminates, regulation system pH to 7 ~ 8, then by reactant transfer in vacuum distillation apparatus, raised temperature to 110 ~ 150 DEG C, absolute pressure is 1KPa, and underpressure distillation obtains alkyl glycoside coarse product, the alkyl glucoside surfactant must refined after separating-purifying.
In step one, fatty alcohol is C
8~ C
16-OH.
In step 2, regulation system pH adopts volumetric molar concentration to be the NaOH solution of 1mol/L.
Embodiment 1:
Get the fatty alcohol (C that molfraction is 3 parts
12-OH) and the glucose of 1 part join in polyfluortetraethylene pipe, the tosic acid adding glucose quality 0.6% is catalyzer, and arranging pressure is that 0.4MPa, 1min are warming up to 70 DEG C; 1min is warming up to 110 DEG C; 5min is reacted, after reaction terminates, with 1mol/LNaOH regulation system pH to 7 at 110 DEG C, be transferred in vacuum distillation apparatus by thick APG again, raised temperature to 120 DEG C, absolute pressure is 1KPa, underpressure distillation obtains the thick product of APG, and after separating-purifying, the productive rate of APG can reach 44.47%.
Embodiment 2:
Get the fatty alcohol (C that molfraction is 4 parts
8-OH) and the glucose of 1 part join in polyfluortetraethylene pipe, the tosic acid adding glucose quality 0.7% is catalyzer, and arranging pressure is that 0.4MPa, 2min are warming up to 70 DEG C; 1min is warming up to 110 DEG C; 3min is reacted, after reaction terminates, with 1mol/LNaOH regulation system pH to 7 at 110 DEG C, be transferred in vacuum distillation apparatus by thick APG again, raised temperature to 110 DEG C, absolute pressure is 1KPa, underpressure distillation obtains the thick product of APG, and after separating-purifying, the productive rate of APG can reach 53%.
Embodiment 3:
Get the fatty alcohol (C that molfraction is 6 parts
14-OH) and the glucose of 1 part join in polyfluortetraethylene pipe, the tosic acid adding glucose quality 0.8% is catalyzer, and arranging pressure is that 0.7MPa, 3min are warming up to 70 DEG C; 2min is warming up to 110 DEG C; 7min is reacted, after reaction terminates, with 1mol/LNaOH regulation system pH to 8 at 110 DEG C, be transferred in vacuum distillation apparatus by thick APG again, raised temperature to 140 DEG C, absolute pressure is 1KPa, underpressure distillation obtains the thick product of APG, and after separating-purifying, the productive rate of APG can reach 61%.
Embodiment 4:
Get the fatty alcohol (C that molfraction is 7 parts
16-OH) and the glucose of 1 part join in polyfluortetraethylene pipe, the tosic acid adding glucose quality 0.7% is catalyzer, and arranging pressure is that 0.5MPa, 2min are warming up to 70 DEG C; 3min is warming up to 110 DEG C; 6min is reacted, after reaction terminates, with 1mol/LNaOH regulation system pH to 8 at 110 DEG C, be transferred in vacuum distillation apparatus by thick APG again, raised temperature to 150 DEG C, absolute pressure is 1KPa, underpressure distillation obtains the thick product of APG, and after separating-purifying, the productive rate of APG can reach 75%.
Content of the present invention is not limited to cited by embodiment, and the conversion of those of ordinary skill in the art by reading specification sheets of the present invention to any equivalence that technical solution of the present invention is taked, is claim of the present invention and contains.
Claims (3)
1., based on the method for microwave irradiation synthesis alkyl glycoside, it is characterized in that:
Realized by following steps:
Step one: getting molfraction is that the fatty alcohol of 3 ~ 7 parts and the glucose of 1 part join in polyfluortetraethylene pipe, the tosic acid adding glucose quality 0.6 ~ 0.8% is catalyzer, arranging pressure is 0.4 ~ 0.7MPa, 1 ~ 3min is warming up to 70 DEG C, then 1 ~ 3min is warming up to 110 DEG C, at 110 DEG C, react 3 ~ 7min;
Step 2: after reaction terminates, regulation system pH to 7 ~ 8, then by reactant transfer in vacuum distillation apparatus, raised temperature to 110 ~ 150 DEG C, absolute pressure is 1KPa, and underpressure distillation obtains alkyl glycoside coarse product, the alkyl glucoside surfactant must refined after separating-purifying.
2. the method based on microwave irradiation synthesis alkyl glycoside according to strong request 1, is characterized in that:
In step one, fatty alcohol is C
8~ C
16-OH.
3. the method based on microwave irradiation synthesis alkyl glycoside according to strong request 2, is characterized in that:
In step 2, regulation system pH adopts volumetric molar concentration to be the NaOH solution of 1mol/L.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510564250.2A CN105061523A (en) | 2015-09-08 | 2015-09-08 | Method for synthesizing alkyl glycoside based on microwave radiation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510564250.2A CN105061523A (en) | 2015-09-08 | 2015-09-08 | Method for synthesizing alkyl glycoside based on microwave radiation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105061523A true CN105061523A (en) | 2015-11-18 |
Family
ID=54491080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510564250.2A Pending CN105061523A (en) | 2015-09-08 | 2015-09-08 | Method for synthesizing alkyl glycoside based on microwave radiation |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105061523A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105646606A (en) * | 2016-01-20 | 2016-06-08 | 上海发凯化工有限公司 | Alkyl glycoside sulfonate and synthesis method thereof |
| CN109180751A (en) * | 2018-09-04 | 2019-01-11 | 安徽红太阳新材料有限公司 | The preparation method of alkyl glycosides 1214 |
| CN109180750A (en) * | 2018-09-04 | 2019-01-11 | 安徽红太阳新材料有限公司 | The method of Dextrose Monohydrate synthesizing alkyl polyglycoside 0810 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005014518A1 (en) * | 2003-08-07 | 2005-02-17 | Aldivia S.A. | Estoliding method using dielectric heating |
| CN102250160A (en) * | 2011-05-30 | 2011-11-23 | 浙江赞宇科技股份有限公司 | Method for preparing alkyl polyglucoside (APG) through microwave-ultrasonic wave concerted catalysis |
| WO2012170841A1 (en) * | 2011-06-10 | 2012-12-13 | Isp Investments Inc. | An aqueous volatile organic compound free disinfectant and/or cleaning composition and method of preparation |
-
2015
- 2015-09-08 CN CN201510564250.2A patent/CN105061523A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005014518A1 (en) * | 2003-08-07 | 2005-02-17 | Aldivia S.A. | Estoliding method using dielectric heating |
| CN102250160A (en) * | 2011-05-30 | 2011-11-23 | 浙江赞宇科技股份有限公司 | Method for preparing alkyl polyglucoside (APG) through microwave-ultrasonic wave concerted catalysis |
| WO2012170841A1 (en) * | 2011-06-10 | 2012-12-13 | Isp Investments Inc. | An aqueous volatile organic compound free disinfectant and/or cleaning composition and method of preparation |
Non-Patent Citations (2)
| Title |
|---|
| MATTHIAS NÜCHTER，等: "Microwave-assisted synthesis of alkyl glycosides", 《SYNTHETIC COMMUNICATIONS》 * |
| 周大鹏，等: "微波辐射下NaHSO4·H2O催化合成烷基糖苷", 《日用化学品科学》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105646606A (en) * | 2016-01-20 | 2016-06-08 | 上海发凯化工有限公司 | Alkyl glycoside sulfonate and synthesis method thereof |
| CN105646606B (en) * | 2016-01-20 | 2019-01-18 | 上海发凯化工有限公司 | Sugar-based sulfonates and its synthetic method |
| CN109180751A (en) * | 2018-09-04 | 2019-01-11 | 安徽红太阳新材料有限公司 | The preparation method of alkyl glycosides 1214 |
| CN109180750A (en) * | 2018-09-04 | 2019-01-11 | 安徽红太阳新材料有限公司 | The method of Dextrose Monohydrate synthesizing alkyl polyglycoside 0810 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101225045A (en) | Micro-wave synthetic method for preparing methyl salicylate | |
| CN105061523A (en) | Method for synthesizing alkyl glycoside based on microwave radiation | |
| CN101773840B (en) | Method for hydrothermal synthesis of carbon-silicon composite solid acid catalyst | |
| CN103394370A (en) | Silica gel-supported sulfonic acid dual-core ionic liquid catalyst, and preparation method and application thereof | |
| CN103212437A (en) | Method for preparing titanium-based catalyst and synthesizing epoxypropane and dicumyl peroxide | |
| CN110003203A (en) | A kind of method of synthesis 2- acetyl group -1,10- ferrosin (3) | |
| CN102050752A (en) | Method for synthesizing p-hydroxyphenylglycine | |
| CN103896703A (en) | Method of preparing C5 and C6 alkanes by catalytically converting lignocelluloses by virtue of one-step method | |
| CN103626810A (en) | Method for catalyzing glucose by using magnetic solid acid to produce methyl glucoside | |
| CN103113245A (en) | Method for synthesizing 1-aminoanthraquinone | |
| CN109761916A (en) | A kind of improvement synthetic method of orotic acid | |
| CN102250160A (en) | Method for preparing alkyl polyglucoside (APG) through microwave-ultrasonic wave concerted catalysis | |
| CN106434771B (en) | A method of utilizing aqueous enzymatic method hydrolyzate, residue fermenting and producing alcohol | |
| CN103623744A (en) | Alkyl glycoside gemini surfactant and preparation method thereof | |
| CN102260170B (en) | Method for microwave pipeline production of butyl acetate | |
| CN102212047A (en) | Method for preparing 5-hydroxymethyl furfural by jerusalem artichoke serving as raw material | |
| CN102399191B (en) | Method for synthesizing analgin | |
| CN111620778A (en) | Preparation method of 5-bromo-2-chlorobenzoic acid | |
| CN106478402A (en) | The method that ethanol acid crystal is prepared by methyl glycollate | |
| CN110684060A (en) | Preparation method of alkyl glycoside by using sulfonated graphene catalyst | |
| CN102553490A (en) | Synthetic method of furfural surfactant | |
| CN103804137A (en) | Method used for preparing higher alkanols via rice bran wax normal pressure reduction | |
| CN102718663A (en) | Synthesis method of 5-chloro-1-indene amine | |
| CN102659680B (en) | Method for palladium-carbon catalytic hydrogenation synthesis of analgin | |
| CN103506140B (en) | Lactic acid catalyst for synthesizing and synthetic method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20151118 |