CN105254686B - A kind of preparation method of APG - Google Patents
A kind of preparation method of APG Download PDFInfo
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- CN105254686B CN105254686B CN201510868872.4A CN201510868872A CN105254686B CN 105254686 B CN105254686 B CN 105254686B CN 201510868872 A CN201510868872 A CN 201510868872A CN 105254686 B CN105254686 B CN 105254686B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 24
- 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 claims abstract description 22
- 239000008103 glucose Substances 0.000 claims abstract description 22
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 11
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 claims abstract description 7
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229940029575 guanosine Drugs 0.000 claims abstract description 7
- 206010033546 Pallor Diseases 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 229930182470 glycoside Natural products 0.000 claims description 10
- 150000002338 glycosides Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 9
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical group [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 7
- 229930182478 glucoside Natural products 0.000 claims description 6
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 claims description 6
- 150000008131 glucosides Chemical class 0.000 claims description 5
- 235000011187 glycerol Nutrition 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
- 239000007844 bleaching agent Substances 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- -1 alkyl Glucosides Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 238000004061 bleaching Methods 0.000 abstract description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 abstract description 2
- 230000009965 odorless effect Effects 0.000 abstract description 2
- 238000005979 thermal decomposition reaction Methods 0.000 abstract description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 3
- 230000036632 reaction speed Effects 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000012369 In process control Methods 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005858 glycosidation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010965 in-process control Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- Saccharide Compounds (AREA)
Abstract
The invention discloses a kind of preparation method of APG, including with glucose, C8‑C20Fatty alcohol is raw material, and in the presence of binary catalyst, APG is made by reaction of guanosine, except alcohol, decolouring blanching step.This method is carrying agent except alcohol process adds so that the temperature of reaction is relatively low, reduces the thermal decomposition of glucose.Decoloring assistant is added in bleaching process, so as to reduce the usage amount of hydrogen peroxide, and remaining hydrogen peroxide is removed using reducing agent, reduces APG caused peculiar smell in placement process.This method technique is simple, and cost is low, can obtain the APG of colorless and odorless function admirable.
Description
Technical field
The invention belongs to organic synthesis field, specially a kind of preparation method of APG.
Background technology
APG (APG for short), it is in acidic catalyst by fatty alcohol and starch or the product glucose of its hydrolysis
Under effect, product obtained from a molecular water is sloughed.APG has that surface-active is high, non-stimulated, nontoxic, easily biological-degradable
Etc. feature, green surfactant is acknowledged as.One-step synthesis process be acidic catalyst catalysis under using glucose with
High-carbon fatty alcohol is directly reacted, and sloughs molecular water generation APG, also referred to as direct glycosidation method.But due to glucose with
The polarity spectrum of long-chain fatty alcohol is larger, and reaction speed is slower.Therefore excessive higher alcohols are added in process of production not only may be used
Reaction is smoothed out, the generation of oligosaccharide can also be reduced.But the alcohol that reaction terminates rear excess is stayed in the product without quilt
Remove, smell, concentration and the application effect of product can be influenceed.APG dealcoholysis at present mainly has two methods：Extraction and distillation
Method, mainly the way of distillation is used in industrial production, because grape carbohydrates and their derivative is all heat-sensitive materials, the unstable meeting in high temperature
Decompose and product colour can be deepened, so must the dealcoholysis by the way of being evaporated under reduced pressure.But can be made by adopting this method by one
Firmly absorption is divided to be difficult to remove in the higher alcohols of polyglycoside surfactant, so that product has peculiar smell it can not be applied to food and commodity
In industry.Another problem is exactly that coloured product is deeper, to expect the APG of water white transparency in addition to process control, drift
It is also a big difficult point in vain.Improve reaction speed in process control, it is the test to catalyst choice in fact to reduce the reaction time, mesh
Preceding patent is single DBSA, sulfo-succinic acid etc. mostly, and binary catalyst is from less.And routine is decolourized
When sometimes partly for decompose hydrogen peroxide can remain in APG, the smell of hydrogen peroxide is very big, causes APG putting
Peculiar smell is produced during putting, therefore its bleaching process is also crucial.
The content of the invention
In view of the shortcomings of the prior art, the technical problem that the present invention intends to solve is to provide a kind of preparation side of APG
Method.This method is carrying agent except alcohol process adds so that the temperature of reaction is relatively low, reduces the thermal decomposition of glucose.Bleached
Decoloring assistant is added in journey, so as to reduce the usage amount of hydrogen peroxide, and remaining hydrogen peroxide is removed using reducing agent, reduced
APG caused peculiar smell in placement process.This method technique is simple, and cost is low, can obtain colorless and odorless function admirable
APG.
The technical scheme that the present invention solves the technical problem is to provide a kind of preparation method of APG, including with
Glucose, C8-C20Fatty alcohol is raw material, in the presence of binary catalyst, by reaction of guanosine, except alcohol, decolouring blanching step
APG is made；This method specifically includes following steps：
(1) reaction of guanosine：By C8-C20Fatty alcohol and glucose 4-8 in molar ratio:1 feeds intake, and addition p-methyl benzenesulfonic acid/
The mass ratio of the binary catalyst of ortho phosphorous acid, binary catalyst and glucose sugar is 0.005~0.015:1, reaction pressure 5-
6KPa, reaction temperature are 100 DEG C -140 DEG C, reaction time 2-2.5h；60 DEG C -70 DEG C are then cooled to, regulation reaction system pH
Value obtains the slightly cloudy glycosides alcohol mixture of yellow to 8-10；The matter of p-methyl benzenesulfonic acid and ortho phosphorous acid in the binary catalyst
It is 2-4 to measure ratio:1；
(2) alcohol is removed：The glycosides alcohol mixture that step 1 obtains is warming up to 100 DEG C -120 DEG C, adds and carries agent, mol ratio is
Carry agent:Glucose=0.4-0.6:1, react under 4-5KPa pressure, until noresidue alcohol steams again, obtain flaxen
APG；
(3) decolourize to bleach：The APG that step 2 is obtained is dissolved into the aqueous solution, adds and decolourizes under 70-80 DEG C of normal pressure
Auxiliary agent and hydrogen peroxide, react 30min-70min；Then reducing agent is added, stirring removes remaining hydrogen peroxide, obtains water white transparency
The APG aqueous solution；
The quality of the decoloring assistant and hydrogen peroxide is the 0.6-1% for the APG quality that step 2 obtains；The reduction
The quality of agent is the 0.08-0.1% for the APG quality that step 2 obtains；The carrying agent is ethylene glycol or glycerine；It is described
Decoloring assistant is magnesia or tetraacetyl ethylene diamine；The reducing agent is NaBH4Or NaHSO3。
Compared with prior art, beneficial effect of the present invention is：The present invention uses binary catalyst, and reaction speed is fast, mistake
Cheng Pingwen, high conversion rate.Using carry agent so that except the reaction temperature of alcohol process is relatively low, residual alcohol content is low after dealcoholysis, product without
Taste.Optimizing APG solid content makes bleaching process reach optimal, using decoloring assistant, hydrogen peroxide usage amount is greatly reduced,
And remaining hydrogen peroxide is removed using reducing agent, well hydrogen peroxide will not produce peculiar smell to bleaching effect simultaneously.
Embodiment
Below will be by embodiment come the invention will be further described.
The invention provides a kind of preparation method of APG, including with glucose, C8-C20Fatty alcohol is raw material,
In the presence of binary catalyst, APG is made by reaction of guanosine, except alcohol, decolouring blanching step；This method specifically includes
Following steps：
(1) reaction of guanosine：By C8-C20Fatty alcohol and glucose 4-8 in molar ratio:1 feeds intake, and addition p-methyl benzenesulfonic acid/
The mass ratio of the binary catalyst of ortho phosphorous acid, binary catalyst and glucose sugar is 0.005~0.015:1, reaction pressure 5-
6KPa, reaction temperature are 100 DEG C -140 DEG C, reaction time 2-2.5h；60 DEG C -70 DEG C are then cooled to, regulation reaction system pH
Value obtains the slightly cloudy glycosides alcohol mixture of yellow to 8-10；The matter of p-methyl benzenesulfonic acid and ortho phosphorous acid in the binary catalyst
It is 2-4 to measure ratio:1；
(2) alcohol is removed：The glycosides alcohol mixture that step 1 obtains is warming up to 100 DEG C -120 DEG C, adds and carries agent, mol ratio is
Carry agent:Glucose=0.4-0.6:1, react under 4-5KPa pressure, until noresidue alcohol steams again, obtain flaxen
APG；
(3) decolourize to bleach：The APG that step 2 is obtained is dissolved into the aqueous solution, adds and decolourizes under 70-80 DEG C of normal pressure
Auxiliary agent and hydrogen peroxide, react 30min-70min；Then reducing agent is added, stirring removes remaining hydrogen peroxide, obtains water white transparency
The APG aqueous solution.
The 0.6-1% for the APG quality that the quality of the decoloring assistant and hydrogen peroxide obtains for step 2, decoloring assistant
Can be any mass ratio with hydrogen peroxide, preferably 1:1；The quality of the reducing agent is the APG quality that step 2 obtains
0.08-0.1%；
The carrying agent is ethylene glycol or glycerine；The decoloring assistant is magnesia (MgO) or tetraacetyl ethylene diamine
(TAED)；The reducing agent is NaBH4Or NaHSO3。
The mass fraction of the APG aqueous solution in the step 3 is 45-55%.
Embodiment 1
N-octyl alcohol 1290kg is added in synthesis reactor, opens stirring, adds glucose 310kg, binary catalyst 4kg, two
First catalyst is p-methyl benzenesulfonic acid and ortho phosphorous acid by weight 4:1 is made；It is 4.8KPa to control reaction pressure, by reaction temperature
120 DEG C are risen to, reaction 2h is kept, opens condensed water, be cooled to 70 DEG C, add potassium hydroxide 480g, stir 15 minutes, be neutralized to pH
For 8.5, the slightly cloudy glycosides alcohol mixture 1529kg of yellow is obtained；Temperature is risen to 120 DEG C again, adds glycerine 80kg,
Under 4KPa pressure, excessive n-octyl alcohol is distilled, obtains flaxen APG；It is redissolved into the alkyl that mass fraction is 45%
The glucosides aqueous solution, 80 DEG C are maintained the temperature at, add tetraacetyl ethylene diamine 5kg and add hydrogen peroxide 5kg, stir 30min, add
1.6kgNaBH4, 10min is stirred, residual hydrogen peroxide is removed, obtains the APG aqueous solution of water white transparency.
Embodiment 2
N-octyl alcohol 1250kg is added in synthesis reactor, opens stirring, adds glucose 350kg, binary catalyst 3.5kg,
Binary catalyst is p-methyl benzenesulfonic acid and ortho phosphorous acid by weight 2:1 is made；It is 6KPa to control reaction pressure, by reaction temperature
125 DEG C are risen to, reaction 2.5h is kept, opens condensed water, be cooled to 65 DEG C, add potassium hydroxide 500g, stir 15 minutes, be neutralized to
PH is 9, obtains the slightly cloudy glycosides alcohol mixture 1520kg of yellow；Temperature is risen to 100 DEG C again, adds glycerine 90kg,
Under 5KPa pressure, excessive n-octyl alcohol is distilled, obtains flaxen APG；It is redissolved into the alkyl that mass fraction is 48%
The glucosides aqueous solution, 70 DEG C are maintained the temperature at, add MgO5.5kg and add hydrogen peroxide 5.5kg, stir 50min, add
1.7kgNaBH4, 10min is stirred, residual hydrogen peroxide is removed, obtains the APG aqueous solution of water white transparency.
Embodiment 3
N-octyl alcohol 1200kg is added in synthesis reactor, opens stirring, adds glucose 400kg, binary catalyst 3kg, two
First catalyst is p-methyl benzenesulfonic acid and ortho phosphorous acid by weight 3:1 is made；It is 5.4KPa to control reaction pressure, by reaction temperature
120 DEG C are risen to, reaction 2h is kept, opens condensed water, be cooled to 70 DEG C, add potassium hydroxide 550g, stir 15 minutes, be neutralized to pH
For 9.5, the slightly cloudy glycosides alcohol mixture 1520kg of yellow is obtained；Temperature is risen to 110 DEG C again, adds ethylene glycol 80kg,
Under 4.5KPa pressure, excessive n-octyl alcohol is distilled, obtains flaxen APG；It is redissolved into the alkane that mass fraction is 50%
The base glucosides aqueous solution, 75 DEG C are maintained the temperature at, add 6kg MgO and add hydrogen peroxide 6kg, stir 60min, add
1.6kgNaHSO3, 10min is stirred, residual hydrogen peroxide is removed, obtains the APG aqueous solution of water white transparency.
Embodiment 4
N-octyl alcohol 1130kg is added in synthesis reactor, opens stirring, adds glucose 470kg, binary catalyst 4000g,
Binary catalyst is p-methyl benzenesulfonic acid and ortho phosphorous acid by weight 4:1 is made；It is 5.5KPa to control reaction pressure, by reaction temperature
Degree rises to 120 DEG C, keeps reaction 2.3h, opens condensed water, be cooled to 65 DEG C, add potassium hydroxide 600g, stir 15 minutes, neutralizes
It is 9 to PH, obtains the slightly cloudy glycosides alcohol mixture 1500kg of yellow；Temperature is risen to 100 DEG C again, adds ethylene glycol 100kg,
Under 4KPa pressure, excessive n-octyl alcohol is distilled, obtains flaxen APG；It is redissolved into the alkane that mass fraction is 55%
The base glucosides aqueous solution, 80 DEG C are maintained the temperature at, add tetraacetyl ethylene diamine 5.8kg and add hydrogen peroxide 5.8kg, stir 70min,
Add 1.5kgNaHSO3, 10min is stirred, residual hydrogen peroxide is removed, obtains the APG aqueous solution of water white transparency.
Claims (3)
1. a kind of preparation method of APG, including with glucose, C8-C20Fatty alcohol is raw material, in the work of binary catalyst
Under, APG is made by reaction of guanosine, except alcohol, decolouring blanching step；This method specifically includes following steps：
（1）Reaction of guanosine：By C8-C20Fatty alcohol and glucose 4-8 in molar ratio:1 feeds intake, and adds p-methyl benzenesulfonic acid/time Asia
The mass ratio of the binary catalyst of phosphoric acid, binary catalyst and glucose sugar is 0.005 ~ 0.015:1, reaction pressure 5-6KPa,
Reaction temperature is 100 DEG C -140 DEG C, reaction time 2-2.5h；60 DEG C -70 DEG C are then cooled to, regulation pH value of reaction system to 8-
10, obtain the slightly cloudy glycosides alcohol mixture of yellow；The mass ratio of p-methyl benzenesulfonic acid and ortho phosphorous acid is in the binary catalyst
2-4:1；
（2）Except alcohol：The glycosides alcohol mixture that step 1 obtains is warming up to 100 DEG C -120 DEG C, adds and carries agent, mol ratio is carrying
Agent:Glucose=0.4-0.6:1, reacted under 4-5KPa pressure, until noresidue alcohol steams again, obtain flaxen alkyl
Glucosides；
（3）Decolourize to bleach：The APG that step 2 is obtained is dissolved into the aqueous solution, and decoloring assistant is added under 70-80 DEG C of normal pressure
And hydrogen peroxide, react 30min-70min；Then reducing agent is added, stirring removes remaining hydrogen peroxide, obtains the alkane of water white transparency
The base glucosides aqueous solution；
The quality of the decoloring assistant and hydrogen peroxide is the 0.6-1% for the APG quality that step 2 obtains；The reducing agent
Quality is the 0.08-0.1% for the APG quality that step 2 obtains；The carrying agent is ethylene glycol or glycerine；The decolouring
Auxiliary agent is magnesia or tetraacetyl ethylene diamine；The reducing agent is NaBH4Or NaHSO3。
2. the preparation method of APG according to claim 1, it is characterised in that the APG water in the step 3
The mass fraction of solution is 45-55%.
3. the preparation method of APG according to claim 1, it is characterised in that the decoloring assistant and hydrogen peroxide
Mass ratio is 1:1.
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| CN107188913B (en) * | 2017-06-12 | 2019-09-20 | 江苏万淇生物科技股份有限公司 | A kind of sorbitan fatty acid ester glucosides and the preparation method and application thereof |
| FR3080384B1 (en) * | 2018-04-20 | 2020-10-09 | Arkema France | USE OF HYPOPHOSPHOROUS ACID FOR THE ESTERIFICATION OF FREE FATTY ACIDS |
| CN111690021B (en) * | 2020-06-24 | 2023-03-14 | 江苏万淇生物科技股份有限公司 | Method for removing fatty alcohol in alkyl glycoside |
| CN111763569B (en) * | 2020-07-10 | 2023-08-25 | 湖北中烟工业有限责任公司 | Fragrance-changeable essence and spice and synthesis method thereof |
| CN112979720B (en) * | 2021-03-06 | 2022-10-04 | 浙江正泰工程设计有限公司 | Preparation method of alkyl glycoside |
| CN114685570B (en) * | 2022-03-28 | 2024-04-02 | 浙江皇马科技股份有限公司 | Preparation method of green surfactant alkyl glycoside |
| CN114853830A (en) * | 2022-05-26 | 2022-08-05 | 苏州聚棕生物科技有限公司 | Safe and environment-friendly alkyl glycoside preparation method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0077167B1 (en) * | 1981-10-08 | 1985-09-11 | Rohm And Haas France, S.A. | A process for preparing surface-active glycosides and the use of the glycosides in cosmetic, pharmaceutical and household products |
| CN1285840A (en) * | 1997-11-22 | 2001-02-28 | Lg化学株式会社 | Process for preparing pale-colored and transparent alkyl glycosides |
| CN1456567A (en) * | 2002-05-10 | 2003-11-19 | 中国石油天然气股份有限公司 | Method for synthesizing oxo-alcohol alkyl glucoside from oxo-alcohol and glucose by one-step method |
| CN101696226A (en) * | 2009-11-06 | 2010-04-21 | 石家庄金莫尔化学品有限公司 | Synthetic method for preparing colorless transparent alkyl polyglucoside |
-
2015
- 2015-12-01 CN CN201510868872.4A patent/CN105254686B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0077167B1 (en) * | 1981-10-08 | 1985-09-11 | Rohm And Haas France, S.A. | A process for preparing surface-active glycosides and the use of the glycosides in cosmetic, pharmaceutical and household products |
| CN1285840A (en) * | 1997-11-22 | 2001-02-28 | Lg化学株式会社 | Process for preparing pale-colored and transparent alkyl glycosides |
| CN1456567A (en) * | 2002-05-10 | 2003-11-19 | 中国石油天然气股份有限公司 | Method for synthesizing oxo-alcohol alkyl glucoside from oxo-alcohol and glucose by one-step method |
| CN101696226A (en) * | 2009-11-06 | 2010-04-21 | 石家庄金莫尔化学品有限公司 | Synthetic method for preparing colorless transparent alkyl polyglucoside |
Non-Patent Citations (4)
| Title |
|---|
| 制备浅色烷基糖苷的研究;杨春光，等;《日用化学品科学》;20090930;第32卷(第9期);第21-25,29页 * |
| 烷基糖苷的市场状况及合成工艺进展;金玉芹，等;《精细化工》;19980531;第15卷(第5期);第5-8页 * |
| 烷基糖苷研究现状及展望;尚会建，等;《现代化工》;20131130;第33卷(第11期);第28-31页 * |
| 马铃薯淀粉基烷基糖苷的合成;章平，等;《化工进展》;20061231;第25卷(第7期);第807-810页 * |
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