CN109180751A - The preparation method of alkyl glycosides 1214 - Google Patents
The preparation method of alkyl glycosides 1214 Download PDFInfo
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- CN109180751A CN109180751A CN201811024051.2A CN201811024051A CN109180751A CN 109180751 A CN109180751 A CN 109180751A CN 201811024051 A CN201811024051 A CN 201811024051A CN 109180751 A CN109180751 A CN 109180751A
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- alkyl glycosides
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- glycosides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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Abstract
The invention discloses a kind of preparation methods of alkyl glycosides 1214, it is mainly using PTSA as catalyst, in 20-70mmHg heated under vacuum, glucose and excess fat alcohol (alcohol sugar molar ratio 4:1) reaction generate alkyl glycosides, after neutralization by dealcoholysis, drift color and etc. obtain 50%APG product；The alkyl glycosides preparation process noon three wastes of the invention generate, carbon dioxide is passed through in raw sugar glycosides reaction process, promote reaction efficiency, solve the problems, such as that glucose easily agglomerates in reaction process, using p-methyl benzenesulfonic acid as catalyst, promote catalytic efficiency, substantially reduce the reaction time, temperature control is appropriate in reaction process, and reaction speed is fast, and by-product is few, vacuum degree is high during dealcoholysis of the present invention simultaneously, the vapo(u)rizing temperature needed is low, is conducive to subsequent drift color effect, and the purity of alkyl glycosides of the invention has reached 97% or more.
Description
Technical field
The present invention relates to technical field of fine, and in particular to a kind of preparation method of alkyl glycosides 1214.
Background technique
Alkyl glycosides APG for short, with excellent ecology and toxicologic properties, excellent physicochemical properties and good
Good compatibility, surface tension is low, strong detergency, foaming abundancy and it is fine and smooth, can with any type surfactant compound,
Synergistic effect is obvious, and nontoxic, harmless, non-stimulated, and it is a kind of property that biological degradability, which is better than present any kind surfactant,
It can good new non-ionic face activating agent and internationally recognized preferred " green " functional surfactant.
Alkyl glycosides surface tension is low, without cloud point, HLB value is adjustable, wetting power is strong, strong detergency, foaming abundancy are fine and smooth, matches
Wu Xingqiang, nontoxic, harmless, non-stimulated to skin, biodegrade is thorough rapidly, can assist with any type surfactant compound
It is obvious with effect, there is stronger broad spectrum antibiotic activity, product thickening effect is significant, is easy to dilute, without gelatin phenomenon, user
Just；And resistance to highly basic, resistance to strong acid, resistance to hard water, salt-resistance are strong.It can be used as shampoo, shower cream, facial cleanser, liquid detergent, wash one's hands
The primary raw material of the daily-use chemical industries such as liquid, tableware detergent, vegetable and fruit cleaning agent is also used in soap powder, non-phosphate detergent, without phosphorus washes
In the synthetic detergents such as clothing powder.
It is existing that using glucose and fatty alcohol as raw material, the synthesis processing of alkyl polyglycosides under acid catalysed conditions is graininess Portugal
Grape sugar and fatty alcohol carry out condensation reaction, and then neutralized, distillation and decoloration bleaching etc. obtain alkyl glycosides product；There are still Portugals
Grape sugar and the reaction speed of fatty alcohol condensation reaction are slow, and the reaction time is long, and use acid catalyst in condensation reaction, therefore
The dehydration for the dehydrating condensation and glucose itself being easy to happen between glucose keeps impurity content in alkyl glycosides product high,
Color is deep, and clean difficult problem.
Summary of the invention
In order to alleviate shortcomings and deficiencies of the prior art, the purpose of the present invention is to provide a kind of systems of alkyl glycosides 1214
Preparation Method.
To achieve the goals above, the present invention adopts the following technical scheme:
The preparation method of alkyl glycosides 1214, specifically includes the following contents:
(1) by C12-C14Fatty alcohol 4-5:1 feeds intake in molar ratio with glucose, catalyst activity charcoal and to toluene is added
The mass ratio of sulfonic acid, the active carbon and glucose sugar is 0.005-0.01:1, the matter of the p-methyl benzenesulfonic acid and glucose sugar
Amount is evacuated to 28-32mmHg, is warming up to 105-108 DEG C, insulation reaction 75-85min, then rise than being 0.008-0.012:1
Temperature is to 108 DEG C -110 DEG C, microwave radiation the reaction was continued hour, then is warming up to 111-113 DEG C, reacts 1.5-2.5h, adjusts
PH value of reaction system to 8-10, solution becomes grey black by transparent, stops heating, unload vacuum after cooling；
(2) it is added into the reactant of step (1) and is equivalent to glucose quality 0.06%-0.07%MgO, 1.5%-
1.7% liquid alkaline, is stirred to react 20-30min, filters to take filtrate；
(3) above-mentioned steps (2) filtrate is heated to being completely dissolved, is evaporated under reduced pressure, control pressure is 25.0-32.5KPa, is added
Heat starts to steam fatty alcohol to 130 DEG C -132 DEG C, and to 190 DEG C -205 DEG C, control heating rate is 2.0 DEG C/min- for persistently overheating
2.5 DEG C/min, until fatty alcohol steams completely, obtain 1214 crude product of alkyl glycosides；
(4) 1214 crude product of alkyl glycosides for obtaining step (3) dissolves, and is added under 70-80 DEG C of normal pressure and is equivalent to grape
Saccharic amount 12.0%-12.5% liquid alkaline and 7%-8% hydrogen peroxide, heat preservation decoloration 40-50min；Then it adds and is equivalent to grape
Saccharic amount 4.5%-5.5% hydrogen peroxide, secondary drift colour response 20min-30min；Finally stirring removes remaining hydrogen peroxide, obtains
Alkyl glycosides 1214.
The C12-C14Fatty alcohol be n-dodecanol, tetradecanol one or two mixed alcohol.
The particle size of the active carbon is 80-100 mesh.
The mass ratio of the p-methyl benzenesulfonic acid and glucose sugar is 0.01:1；The microwave irradiation power is 250W.
The step (1) is passed through CO into solution after vacuumizing2, CO2Be passed through rate be 1-2ml/min.
The hydrogen peroxide concentration is 45%-55%.
Beneficial effects of the present invention:
Compared with prior art, the alkyl glycosides preparation process noon three wastes of the invention generate, in raw sugar glycosides reaction process
It is passed through carbon dioxide, reaction efficiency is promoted, solves the problems, such as that glucose easily agglomerates in reaction process, using micro- in reaction process
Wave radiation can not only accelerate the dissolution of glucose, but also can accelerate the rate of reaction, using p-methyl benzenesulfonic acid as catalyst,
Catalytic efficiency is promoted, the reaction time is substantially reduced, temperature control is appropriate in reaction process, and reaction speed is fast, and by-product is few, together
When dealcoholysis of the present invention during vacuum degree it is high, the vapo(u)rizing temperature needed is low, is conducive to subsequent drift color effect, alkyl of the invention
The purity of glucosides has reached 97% or more.
Specific embodiment
Embodiment 1:
8:30 feeds intake: glucose (food-grade) 120g；AlcoholC12-14516g；
Active carbon and p-methyl benzenesulfonic acid is added in 8:40 according to the ratio；30mmHg is vacuumized, CO is passed through2, being passed through rate is
1.5ml/min, heating；
106 DEG C of 9:10, reaction timing starts；
110 DEG C of 10:40, glucose moiety reaction dissolution；
112 DEG C of 11:40, microwave radiation, most of sugar reaction, solution went clear；
112 DEG C of 13:10, the graying black of solution colour；
110 DEG C of 14:00, stop heating；
Vacuum is unloaded after 14:10 cooling；
0.08gMgO, 1.9g liquid alkaline, material gross weight 620g is added in 14:15；
14:50 filtering, filtrate 608.2g；
Next day:
8:10 is dissolved by heating；
8:40 vacuum distillation；
132 DEG C of 9:05 start to steam mixed alcohol；
200 DEG C of 9:40, temperature continues to rise, and the temperature condition is maintained to continue to distill；
9:55 receives bottleneck substantially without fraction, steams mixed alcohol 416.7g (partially solidified to remain in condenser pipe)；
The thick glycosides 179.4g of 10:10 heats water 147g, stirring and dissolving；
Liquid alkaline 14.7g, hydrogen peroxide 9g, 65-70 DEG C of heat preservation decoloration is added in 13:35；
Bis- drift colors of hydrogen peroxide 6g are added in 15:50；
Product gross weight 352.2g, color are deeper.
The properties of product of manufactured alkyl glycosides 1214 are as follows:
Claims (7)
1. the preparation method of alkyl glycosides 1214, which is characterized in that specifically include the following contents:
(1) by C12-C14Fatty alcohol 4-5:1 feeds intake in molar ratio with glucose, catalyst activity charcoal and p-methyl benzenesulfonic acid is added,
The mass ratio of the active carbon and glucose sugar is 0.005-0.01:1, and the mass ratio of the p-methyl benzenesulfonic acid and glucose sugar is
0.008-0.012:1 is evacuated to 28-32mmHg, is warming up to 105-108 DEG C, and insulation reaction 75-85min is then heated to
108 DEG C -110 DEG C, microwave radiation the reaction was continued hour, then it is warming up to 111-113 DEG C, 1.5-2.5h is reacted, reaction is adjusted
System pH to 8-10, solution becomes grey black by transparent, stops heating, unload vacuum after cooling；
(2) it is added into the reactant of step (1) and is equivalent to glucose quality 0.06%-0.07%MgO, 1.5%-1.7% liquid
Alkali is stirred to react 20-30min, filters to take filtrate；
(3) above-mentioned steps (2) filtrate is heated to being completely dissolved, is evaporated under reduced pressure, control pressure is 25.0-32.5KPa, is heated to
130 DEG C -132 DEG C start to steam fatty alcohol, and to 190 DEG C -205 DEG C, control heating rate is 2.0 DEG C/min-2.5 for persistently overheating
DEG C/min until fatty alcohol steams completely obtains 1214 crude product of alkyl glycosides；
(4) 1214 crude product of alkyl glycosides for obtaining step (3) dissolves, and is added under 70-80 DEG C of normal pressure and is equivalent to grape saccharic
Measure 12.0%-12.5% liquid alkaline and 7%-8% hydrogen peroxide, heat preservation decoloration 40-50min；Then it adds and is equivalent to grape saccharic
Measure 4.5%-5.5% hydrogen peroxide, secondary drift colour response 20min-30min；Finally stirring removes remaining hydrogen peroxide, obtains alkyl
Glucosides 1214.
2. the preparation method of alkyl glycosides 1214 according to claim 1, which is characterized in that the C12-C14Fat
Alcohol is n-dodecanol, tetradecanol one or two mixed alcohol.
3. the preparation method of alkyl glycosides 1214 according to claim 1, which is characterized in that the partial size of the active carbon is big
Small is 80-100 mesh.
4. the preparation method of alkyl glycosides 1214 according to claim 1, which is characterized in that the p-methyl benzenesulfonic acid with
The mass ratio of glucose sugar is 0.01:1.
5. the preparation method of alkyl glycosides 1214 according to claim 1, which is characterized in that the microwave irradiation power
For 200W-300W.
6. the preparation method of alkyl glycosides 1214 according to claim 1, which is characterized in that the step (1) is taken out true
CO is passed through in empty backward solution2, CO2Be passed through rate be 1-2ml/min.
7. the preparation method of alkyl glycosides 1214 according to claim 1, which is characterized in that the hydrogen peroxide concentration is
45%-55%.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1285840A (en) * | 1997-11-22 | 2001-02-28 | Lg化学株式会社 | Process for preparing pale-colored and transparent alkyl glycosides |
| CN1634949A (en) * | 2004-10-18 | 2005-07-06 | 中国日用化学工业研究院 | Process for preparing light color transparent alkyl glycoside |
| CN104138769A (en) * | 2013-10-29 | 2014-11-12 | 中国石油化工股份有限公司 | Preparation method of loaded catalyst for synthesis of alkyl glucoside |
| CN105061523A (en) * | 2015-09-08 | 2015-11-18 | 陕西科技大学 | Method for synthesizing alkyl glycoside based on microwave radiation |
-
2018
- 2018-09-04 CN CN201811024051.2A patent/CN109180751A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1285840A (en) * | 1997-11-22 | 2001-02-28 | Lg化学株式会社 | Process for preparing pale-colored and transparent alkyl glycosides |
| CN1634949A (en) * | 2004-10-18 | 2005-07-06 | 中国日用化学工业研究院 | Process for preparing light color transparent alkyl glycoside |
| CN104138769A (en) * | 2013-10-29 | 2014-11-12 | 中国石油化工股份有限公司 | Preparation method of loaded catalyst for synthesis of alkyl glucoside |
| CN105061523A (en) * | 2015-09-08 | 2015-11-18 | 陕西科技大学 | Method for synthesizing alkyl glycoside based on microwave radiation |
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Application publication date: 20190111 |