CN102250160B - Method for preparing alkyl polyglucoside (APG) through microwave-ultrasonic wave concerted catalysis - Google Patents
Method for preparing alkyl polyglucoside (APG) through microwave-ultrasonic wave concerted catalysis Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 9
- 230000002153 concerted effect Effects 0.000 title claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 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 15
- 239000008103 glucose Substances 0.000 claims abstract description 15
- 230000002378 acidificating effect Effects 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 230000005855 radiation Effects 0.000 claims abstract description 4
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- -1 alkyl glycoside Chemical class 0.000 claims description 11
- 229930182470 glycoside Natural products 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 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 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- 229930182478 glucoside Natural products 0.000 description 6
- 230000009466 transformation Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000008131 glucosides Chemical class 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000005858 glycosidation reaction Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000013019 agitation Methods 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010015946 Eye irritation Diseases 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 231100000013 eye irritation Toxicity 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing alkyl polyglucoside (APG) through microwave-ultrasonic wave concerted catalysis, and aims to provide a method having the advantages of high reaction speed, high conversion rate, small environmental influence and the like. The technical scheme comprises the following steps: a, adding glucose and fatty alcohol into a container according to a mol ratio of 1:(2-10), stirring, carrying out microwave heating for 5 minutes under ultrasonic wave radiation conditions to 110-120 DEG C, and carrying out vacuum dewatering for 15 minutes at the absolute pressure of 1.5-6.5 KPa; b, adding an acidic catalyst, and reacting for 30-90 minutes at the absolute pressure of 1.5-6.5 KPa; c, when the temperature is cooled to 50-80 DEG C after the reaction, neutralizing the acidic catalyst with a neutralizer until the pH value is 8-11; and d, raising the temperature to 120-200 DEG C, and carrying out reduced pressure distillation for dealcoholization at the absolute pressure of 1.5-6.5 KPa, thus obtaining a crude APG product.
Description
Technical field
The invention belongs to the preparation field of tensio-active agent, particularly a kind of method for preparing alkyl glycoside with the microwave-ultrasonic concerted catalysis.
Background technology
Alkyl glycoside (alkyl polyglycoside, APG for short) be a class novel surfactant of developing beginning of the nineties late 1980s, many advantages with nonionic and anion surfactant, not only low, active high, the strong detergency of surface tension, foam are abundant fine and smooth and stablize, and good with other tensio-active agent compatiblenesies,, the advantages such as biological degradation good, nontoxic, consistency good, environmentally safe little to the skin eye irritation.Be widely used in washing composition, industrial emulsion agent, makeup, food and medicine trade.Because its synthesis material and performance characteristic are described as mildness of new generation " green " tensio-active agent, it is the unique kind that really deserves to be called " world-class " tensio-active agent after LAS, AES and AEO.
The synthetic method of APG has the Betamethasone Ketal structures alcoholysis method of the glucosides method (two-step approach) that turns, direct glycosidation method (single stage method), enzyme catalysis method, former ester method and sugar.Turning the glucosides method is that glucose first reacts with butanols, and then reacts with higher alcohols, obtains the glucosides of higher alcohols.United States Patent (USP) (US 5374716), Chinese patent (CN92102625.0, CN200510096464.8, CN98813130.7) all adopt this method to prepare alkyl glycoside.Turn that the technical process of glucosides method is long and poor product quality is eliminated just gradually.Directly the glycosidation method is that glucose reacts under the effect of an acidic catalyst with higher alcohols, saved and turned two pure exchange steps in the glucosides method, technique is simplified, in product, without the low alkyl group glucosides, exist, existing batch production device adopts this kind of method more, but in direct glycosidation method technique, glycosylation reaction is two reaction systems of a solid-liquid, and the solubleness of glucose in higher alcohols is minimum, make speed of response slow, and sugar easily lump.For addressing these problems, China Daily Chemical Industry Research Institute adopts the patented technology (CN 200410064505.0) of independent research, designed the special-purpose homogenizing mill with conveying, crushing function, make the sugar of reactor bottom remain flow state, be difficult for being deposited on for a long time bottom, accelerated speed of response.Shao Baihua etc. (research of Synthesis of Dodecyl Glucoside at Normal Pressure. chemical engineer .2000.80 (5): 15-17.) adopt the technique that is pre-mixed and adds dispersion agent, increase the solubleness of glucose in higher alcohols, make the reaction times shorten 20-30min.Though above method has certain effect, larger limitation is all arranged.
Summary of the invention
The present invention seeks to for the existing problem of prior art, a kind of synthesizing alkyl polyglycoside catalyzed method of microwave-ultrasonic of utilizing is provided.It is fast that the method has speed of response, and transformation efficiency is high, to advantages such as environmental influence are little.
Technical scheme provided by the invention is:
A kind of method for preparing alkyl glycoside with the microwave-ultrasonic concerted catalysis follows these steps to carry out:
A, by mol ratio, be 1: the glucose of 2-10 and fatty alcohol add in container and stir, and under microwave heating, Ultrasonic Radiation condition, 5min is warmed up to 110-120 ℃, absolute pressure 1.5-6.5KPa, vacuum hydro-extraction 15min;
B, add an acidic catalyst, under absolute pressure 1.5-6.5KPa, reaction 30-90min;
After c, reaction finish, when temperature is reduced to 50-80 ℃, with in neutralizing agent and an acidic catalyst to pH=8-11;
D, increase the temperature to 120-200 ℃, absolute pressure 1.5-6.5KPa, carry out the underpressure distillation dealcoholysis, obtains the thick product of APG.
Described an acidic catalyst is one or more in sulfuric acid, hydrochloric acid, phosphoric acid, sodium pyrosulfate, alkyl benzene sulphonate (ABS), tosic acid, phospho-wolframic acid, citric acid, storng-acid cation exchange resin.
The 0.5-5% that the consumption of described an acidic catalyst is glucose weight.
Described fatty alcohol carbon chain lengths is 8-18.
Described neutralizing agent is sodium bicarbonate, sodium hydroxide, sodium carbonate and one or both mixture thereof.
Described ultrasonic power 200W-700W; Microwave heating power is 100-600W.
The invention has the beneficial effects as follows, utilize microwave-ultrasonic synthesizing alkyl polyglycoside catalyzed, compared with prior art have following characteristics: (1) speed of response is fast, and the reaction times is short.Under the conventional heating condition, synthesizing alkyl polyglycoside needs 5-6h, and adopting microwave heating to prepare alkyl glycoside needs 30-60min.(2) inversion rate of glucose is high, can reach 99%.
Embodiment
The technology of alkyl glycoside for preparing with the microwave-ultrasonic concerted catalysis of the present invention is by microwave heating, the effective combination of Ultrasonic Radiation.Microwave heating is compared with traditional type of heating, and its advantage is that microwave heating has very strong penetration, can greatly improve speed of response, reduces reaction activity, is a kind of eco-friendly novel synthetic technology.Ultrasonic wave is the very wide a kind of high frequency mechanical wave of range of frequency, is the mechanical energy of concentrating, and utilizes hyperacoustic mechanical effect can reduce the caking of glucose, improves the dispersiveness in alcohol, can make inhomogeneous reaction carry out smoothly.Fully utilize the two plurality of advantages, compared with the prior art obvious technical progress and difference are arranged: speed of response is fast, and Reaction time shorten, energy-efficient greatly, and transformation efficiency is high.In synthetic, reaction equation is as follows:
Embodiment 1
Add 54gC in the 100mL three-necked bottle
12/14fatty alcohol, 10g glucose, be placed in the microwave reactor central position, installs the electric stirring bar, design temperature 5min is warmed up to 115 ℃, and then vacuum hydro-extraction 15min adds the 0.1g alkyl benzene sulphonate (ABS), set the microwave irradiation power of 150W, under the condition of absolute pressure 6.0KPa, reaction 30min.Reaction treats that temperature is reduced to 80 ℃ after finishing, and with sodium bicarbonate, is neutralized to pH=8, increases the temperature to 140 ℃, and absolute pressure 6.5KPa, carry out the underpressure distillation dealcoholysis, obtains the thick product of APG, transformation efficiency 69%.
Embodiment 2
In the 100mL three-necked bottle, add 54gC
16/18fatty alcohol, 12g glucose, be placed in the microwave reactor central position, installs the electric stirring bar, 5min is warmed up to 118 ℃, and then vacuum hydro-extraction add the 0.1g sodium pyrosulfate, set the microwave irradiation power of 400W, under the condition of absolute pressure 6.5KPa, reaction 60min.Reaction treats that temperature is reduced to 70 ℃ after finishing, and with sodium carbonate, is neutralized to pH=8.5, increases the temperature to 130 ℃, and absolute pressure 6.5KPa, carry out the underpressure distillation dealcoholysis, obtains the thick product of APG, transformation efficiency 95%.
Embodiment 3
In the 100mL three-necked bottle, add 60gC
8/10fatty alcohol, 10g glucose, be placed in the microwave reactor central position, installs ultrasonic unit, 5min is warmed up to 120 ℃, vacuum hydro-extraction, then add the 0.5g tosic acid, sets ultrasonic power 600W, magnetic agitation, the microwave irradiation power of 500W, under the condition of absolute pressure 6.0KPa, reaction 30min.Reaction treats that temperature is reduced to 60 ℃ after finishing, and with sodium hydroxide, is neutralized to pH=9, increases the temperature to 135 ℃, and absolute pressure 4.5KPa, carry out the underpressure distillation dealcoholysis, obtains the thick product of APG, transformation efficiency 99%.
Embodiment 4
In the 100mL three-necked bottle, add 60gC
12/14fatty alcohol, 10g glucose, be placed in the microwave reactor central position, installs ultrasonic unit, 5min is warmed up to 115 ℃, vacuum hydro-extraction, then add the 0.1g tosic acid, sets ultrasonic power 200W, magnetic agitation, the microwave irradiation power of 400W, under the condition of absolute pressure 6.2KPa, reaction 90min.Reaction treats that temperature is reduced to 70 ℃ after finishing, and with sodium hydroxide, is neutralized to pH=9, increases the temperature to 135 ℃, and absolute pressure 3.5KPa, carry out the underpressure distillation dealcoholysis, obtains the thick product of APG, transformation efficiency 97%.
Claims (2)
1. a method for preparing alkyl glycoside with the microwave-ultrasonic concerted catalysis follows these steps to carry out:
A, the glucose and the fatty alcohol that by mol ratio, are 1:2-10 add in container and stir, and under microwave heating, Ultrasonic Radiation condition, 5min is warmed up to 110-120 ℃, absolute pressure 1.5-6.5KPa, vacuum hydro-extraction 15min;
B, add an acidic catalyst, under absolute pressure 1.5-6.5KPa, reaction 30-90min;
After c, reaction finish, when temperature is reduced to 50-80 ℃, with in neutralizing agent and an acidic catalyst to pH=8-11;
D, increase the temperature to 120-200 ℃, absolute pressure 1.5-6.5KPa, carry out the underpressure distillation dealcoholysis, obtains alkyl glycoside coarse product;
Described an acidic catalyst is one or more in sulfuric acid, hydrochloric acid, phosphoric acid, sodium pyrosulfate, tosic acid, phospho-wolframic acid, citric acid;
The 0.5-5% that the consumption of described an acidic catalyst is glucose weight;
Described fatty alcohol carbon chain lengths is 8-18;
Described neutralizing agent is one or both the mixture in sodium bicarbonate, sodium hydroxide, sodium carbonate.
2. a kind of method for preparing alkyl glycoside with the microwave-ultrasonic concerted catalysis according to claim 1, is characterized in that described ultrasonic power 200W-700W; Microwave heating power is 100W-600W.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103613620B (en) * | 2013-11-13 | 2016-06-08 | 广州大学 | The method of Dodecyl Glucoside prepared by tapioca |
| CN103641747B (en) * | 2013-12-10 | 2015-11-25 | 江南大学 | A kind of stearyl alcohol polyoxyethylene (5) ether sodium sulfosuccinic diester ultrasonic-microwave synthesis method |
| CN104258905B (en) * | 2014-08-20 | 2016-09-21 | 广西新晶科技有限公司 | A kind of glycosylation reaction composite catalyst and glycosylation reaction |
| CN105061523A (en) * | 2015-09-08 | 2015-11-18 | 陕西科技大学 | Method for synthesizing alkyl glycoside based on microwave radiation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003869A2 (en) * | 1997-07-18 | 1999-01-28 | Henkel Kommanditgesellschaft Auf Aktien | Method for producing alkyl glycosides |
| CN1775790A (en) * | 2005-12-02 | 2006-05-24 | 西北大学 | Method for preparing alkyl glycoside |
| CN101723991A (en) * | 2008-10-15 | 2010-06-09 | 扬州晨化科技集团有限公司 | Method for preparing alkyl polyglycoside |
| CN101775046A (en) * | 2010-01-18 | 2010-07-14 | 华东师范大学 | Preparation method for nonyl glucoside |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5091508B2 (en) * | 2007-03-09 | 2012-12-05 | 公益財団法人野口研究所 | Glycoside derivatives and non-reducing disaccharides and their production |
-
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003869A2 (en) * | 1997-07-18 | 1999-01-28 | Henkel Kommanditgesellschaft Auf Aktien | Method for producing alkyl glycosides |
| CN1775790A (en) * | 2005-12-02 | 2006-05-24 | 西北大学 | Method for preparing alkyl glycoside |
| CN101723991A (en) * | 2008-10-15 | 2010-06-09 | 扬州晨化科技集团有限公司 | Method for preparing alkyl polyglycoside |
| CN101775046A (en) * | 2010-01-18 | 2010-07-14 | 华东师范大学 | Preparation method for nonyl glucoside |
Non-Patent Citations (10)
| Title |
|---|
| C. Limousin，等.Solvent-Free Synthesis of Decyl D-Glycopyranosides Under Focused Microwave Irradiation.《Journal of Carbohydrate Chemistry》.2006,第16卷(第3期),第327-342页. * |
| JP特开2008-222618A 2008.09.25 |
| Laurent F. Bornaghi，等.Microwave-accelerated Fischer glycosylation.《Tetrahedron Letters》.2005,第46卷(第20期),第3485-3488页. * |
| Matthias Nüchter,等.Microwave-assisted synthesis of alkyl glycosides.《Synthetic Communications》.2006,第31卷(第9期),第1279-1281页. * |
| Nadège Ferlin，等.Microwave-assisted synthesis of long-chain alkyl glucopyranosides.《Carbohydrate Research》.2008,第343卷(第16期),第2819-2821页. * |
| Sandrine Brochette-Lemoine,等.Ultrasound in carbohydrate chemistry: sonophysical glucose oligomerisation and sonocatalysed sucrose oxidation.《Ultrasonics Sonochemistry》.2000,第7卷(第4期),第157-159页,参考文献[2]. * |
| 以淀粉为原料合成烷基糖苷工艺的研究;闫兴富;《中国石油大学硕士学位论文》;20100315;第7-9页 * |
| 淀粉基表面活性剂烷基糖苷的研究;袁浩;《贵州大学硕士学位论文》;20071015;第22-23页 * |
| 袁浩.淀粉基表面活性剂烷基糖苷的研究.《贵州大学硕士学位论文》.2007,第22-23页. |
| 闫兴富.以淀粉为原料合成烷基糖苷工艺的研究.《中国石油大学硕士学位论文》.2010,第7-9页. |
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Effective date of registration: 20240202 Address after: No. 128 city head lane, Hangzhou, Zhejiang Province Patentee after: ZANYU TECHNOLOGY GROUP CO.,LTD. Country or region after: China Patentee after: Hangzhou Zanyu Chemical Co.,Ltd. Address before: Hangzhou City, Zhejiang province 310009 City Shangcheng District No. 128 Lane Patentee before: ZANYU TECHNOLOGY GROUP CO.,LTD. Country or region before: China |
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