CN102259024A - Nano Au catalyst for glucose oxidation and preparation and use method thereof - Google Patents
Nano Au catalyst for glucose oxidation and preparation and use method thereof Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 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 title claims abstract description 9
- 239000008103 glucose Substances 0.000 title claims abstract description 9
- 230000003647 oxidation Effects 0.000 title abstract description 7
- 238000007254 oxidation reaction Methods 0.000 title abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000008367 deionised water Substances 0.000 claims abstract description 9
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 108010015776 Glucose oxidase Proteins 0.000 claims description 16
- 239000004366 Glucose oxidase Substances 0.000 claims description 16
- 229940116332 glucose oxidase Drugs 0.000 claims description 16
- 235000019420 glucose oxidase Nutrition 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 239000010931 gold Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 241000370738 Chlorion Species 0.000 claims description 7
- SJUCACGNNJFHLB-UHFFFAOYSA-N O=C1N[ClH](=O)NC2=C1NC(=O)N2 Chemical compound O=C1N[ClH](=O)NC2=C1NC(=O)N2 SJUCACGNNJFHLB-UHFFFAOYSA-N 0.000 claims description 7
- 238000000967 suction filtration Methods 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 7
- 238000010792 warming Methods 0.000 claims description 7
- 229910052737 gold Inorganic materials 0.000 claims description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 2
- 238000005303 weighing Methods 0.000 abstract description 2
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- 229940005574 sodium gluconate Drugs 0.000 abstract 2
- 235000012207 sodium gluconate Nutrition 0.000 abstract 2
- 239000000176 sodium gluconate Substances 0.000 abstract 2
- 238000005406 washing Methods 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 238000004061 bleaching Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002808 molecular sieve Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 230000000630 rising effect Effects 0.000 abstract 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 5
- 239000000174 gluconic acid Substances 0.000 description 5
- 235000012208 gluconic acid Nutrition 0.000 description 5
- 229960001031 glucose Drugs 0.000 description 4
- 239000011943 nanocatalyst Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- MSXHSNHNTORCAW-GGLLEASOSA-M sodium;(2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate Chemical compound [Na+].O[C@H]1O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]1O MSXHSNHNTORCAW-GGLLEASOSA-M 0.000 description 2
- SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 206010021037 Hyponatraemic syndrome Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229960000673 dextrose monohydrate Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000002905 metal composite material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Abstract
The invention discloses a nano Au catalyst for glucose oxidation and a preparation and use method thereof. The method disclosed by the invention comprises the following steps: weighing 1.0g titanium-silicon molecular sieve vector, 2.1-16.8mL chloroauric acid solution with 10g/L; adding deionized water to be uniformly mixed; adding to a water bath; rising the temperature to 60 DEG C; adjusting the pH value to 11-12 by utilizing ammonia water; refluxing for 1 hour at 100-110 DEG C; after completing, filtering; bleaching for 5-10 minutes by utilizing 4.0M ammonia water; washing for 2-4 times by utilizing 10-20mL hot water at 70-90 DEG C; washing off chloride ions; drying for 2 hours at 100-110 DEG C; and finally, roasting for 3 hours in the air at 250-350 DEG C to obtain the catalyst for glucose oxidation. The reaction uses water as a solvent and oxygen as an oxidizer to prepare sodium gluconate through glucose oxidation under the action of the catalyst in alkali conditions. The invention is used for preparing sodium gluconate and has the characteristics of high production efficiency, simplicity and convenience in process procedures and the like, and the products are easy to separate.
Description
Technical field
The present invention relates to a kind of nano catalyst and preparation and using method that is used for glucose oxidase.
Background technology
Gluconic acid and derivative thereof as gluconate, glucolactone etc., are the important multiduty organic chemical industry's products of a class.Gluconic acid can be used for dairy processing industry, prevents the mammary calculus precipitation; Be used for food industry, in food formula, make acid; In addition, also can be used as the antisettling agent etc. of auxiliary agent, the agent of leather aluming, the metal-derusting agent of processing of cleaning agent additive, fabric and metal processing, biodegradable chelating agent, secondary oil recovery.The zinc of gluconic acid and derivative thereof such as gluconic acid, sodium, calcium, ferrous plasma salt have a wide range of applications equally in industries such as chemical industry, food, medicine, light industry.For example, the gluconic acid sodium salt of technical grade is widely used as cement retarder in building industry, can effectively prevent solidifying in the commercial concrete transportation, caking phenomenon; Also can be used as steel surface cleaning agent, vial scavenger specially, anti-incrustation corrosion inhibitor.The gluconic acid sodium salt of food-grade and pharmaceutical grade can be regulated the human acid-base balance, guarantees neural normal effect, effectively prevents the generation of low sodium syndrome, also can be used as food additives and medicine intermediate etc.
The industrial production of gluconic acid mainly is a biological fermentation process both at home and abroad at present.The shortcoming of the method is that the cycle is long to the temperature requirement height, and accessory substance is many, and product purity is low etc.Advantages such as and the heterogeneous catalytic oxidation method is with its productive rate height, and the few and product of accessory substance is easily separated just cause people's attention gradually from twentieth century beginning in 70 years.
The more catalyst of research has (GB 1208101, and JP 8007230) such as Pt/C, Pd/C, catalytic efficiency height at present, but inactivation is very fast, often adds Bi, Ru, Cd, Se, metals such as Co, form bimetallic or many metal composites catalyst (US Patent 5132452, US 4834173, and DE-OS 2936652), make catalyst performance be greatly improved, but still have the phenomenon of metal loss, its cycle efficieny is reduced.
Nano catalyst has more and more caused people's attention with its good selectivity and good low temperature active.In China, nm of gold has had certain research basis (CN 1594265, and CN 101249443, and CN 101805256) for the catalytic oxidation of glucose, simply introduces its composition and preparation method, to the selecting property of glucose more than 99%.The selective oxidation of nano gold catalysis glucose has favorable industrial application prospect.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, a kind of nano catalyst and preparation and using method that is used for glucose oxidase is provided.
The catalyst that is used for glucose oxidase is made up of Au and HTS, and wherein Au is as the main active component of catalyst, and its quality percentage composition is 1.0～8.0%; HTS is as the carrier of catalyst, its quality percentage composition 92.0～99.0%.
The Preparation of catalysts method that is used for glucose oxidase is: get 1.0g HTS carrier, 10g/L chlorauric acid solution 2.1 ~ 16.8mL, adding deionized water mixes, place water-bath, be warming up to 60 ℃, transfer pH to 11 ~ 12 with ammoniacal liquor, 100 ~ 110 ℃ were refluxed 1 hour, finish the back suction filtration, 4.0M ammoniacal liquor rinsing 5 ~ 10 minutes, 70 ~ 90 ℃ of hot water of 10 ~ 20mL are taken out and are washed 2 ~ 4 times, the flush away chlorion, and 100 ~ 110 ℃ are following dry 2 hours, 250 ~ 350 ℃ of following roastings 3 hours in air at last obtain being used for the catalyst of glucose oxidase.
The using method that is used for the catalyst of glucose oxidase is: with mass percent concentration is that 5% D/W and the catalyst that is used for glucose oxidase react, the consumption of glucose is 1000:1～1000:8 with the mol ratio that is used for the catalyst nm of gold of glucose oxidase, reaction temperature is 60 ℃, reaction pressure is a normal pressure, speed aerating oxygen with 39mL/min, add 0.5mol/L NaOH, make the pH value constant 9.5.
The present invention intends supported nanometer gold catalyst on HTS, to improve catalytic activity, keeps good selectivity simultaneously.
Description of drawings
Fig. 1 is a 1wt.% Au/ HTS transmission electron microscope picture.
The specific embodiment
Below be embodiments of the invention.
Embodiment 1: the preparation of catalyst A.
Get 1.0g HTS, 10g/L chlorauric acid solution 2.1mL, add deionized water and mix, place water-bath, be warming up to 60 ℃, transfer pH to 12 with ammoniacal liquor, 100 ℃ were refluxed 1 hour, finish the back suction filtration, 4.0M ammoniacal liquor rinsing 5 minutes, 70 ℃ of hot water of 20mL are taken out and are washed 4 times, the flush away chlorion, 100 ℃ dry 2 hours down, 250 ℃ of following roastings 3 hours in air at last obtain catalyst A, its composition sees Table 1, and transmission electron microscope picture is seen Fig. 1.
Embodiment 2: the preparation of catalyst B.
Get 1.0g HTS, 10g/L chlorauric acid solution 4.2mL, add deionized water and mix, place water-bath, be warming up to 60 ℃, transfer pH to 12 with ammoniacal liquor, 110 ℃ were refluxed 1 hour, finish the back suction filtration, 4.0M ammoniacal liquor rinsing 8 minutes, 90 ℃ of hot water of 20mL are taken out and are washed 4 times, the flush away chlorion, drying is 2 hours under 106 ℃, 300 ℃ of following roastings 3 hours in air at last obtain catalyst B, and its composition sees Table 1.
Embodiment 3: the preparation of catalyst C.
Get 1.0g HTS, 10g/L chlorauric acid solution 8.4mL, add deionized water and mix, place water-bath, be warming up to 60 ℃, transfer pH to 11 with ammoniacal liquor, 105 ℃ were refluxed 1 hour, finish the back suction filtration, 4.0M ammoniacal liquor rinsing 10 minutes, 70 ℃ of hot water of 20mL are taken out and are washed 4 times, the flush away chlorion, drying is 2 hours under 110 ℃, 350 ℃ of following roastings 3 hours in air at last obtain catalyst C, and its composition sees Table 1.
Embodiment 4: the preparation of catalyst D.
Get 1.0g HTS, 10g/L chlorauric acid solution 12.6mL, add deionized water and mix, place water-bath, be warming up to 60 ℃, transfer pH to 12 with ammoniacal liquor, 110 ℃ were refluxed 1 hour, finish the back suction filtration, 4.0M ammoniacal liquor rinsing 10 minutes, 90 ℃ of hot water of 10mL are taken out and are washed 2 times, the flush away chlorion, drying is 2 hours under 110 ℃, 300 ℃ of following roastings 3 hours in air at last obtain catalyst D, and its composition sees Table 1.
Embodiment 5: the preparation of catalyst E.
Get 1.0g HTS, 10g/L chlorauric acid solution 16.8mL, add deionized water and mix, place water-bath, be warming up to 60 ℃, transfer pH to 12 with ammoniacal liquor, 1008 ℃ were refluxed 1 hour, finish the back suction filtration, 4.0M ammoniacal liquor rinsing 9 minutes, 80 ℃ of hot water of 20mL are taken out and are washed 3 times, the flush away chlorion, drying is 2 hours under 110 ℃, 350 ℃ of following roastings 3 hours in air at last obtain catalyst E, and its composition sees Table 1.
The composition of table 1 catalyst A ~ E
Embodiment 6: the catalytic performance test of catalyst A ~ E.
Take by weighing the 1.76g Dextrose Monohydrate, add the 25mL deionized water, being made into mass percent concentration is 5% D/W, the catalyst that adding 0.18g is used for glucose oxidase reacts, reaction temperature is 60 ℃, and reaction pressure is a normal pressure, with the speed aerating oxygen of 39mL/min, add 0.5mol/L NaOH, make the pH value constant 9.5.Reaction result sees Table 2.
The catalytic performance test of table 2 catalyst A ~ E
| Catalyst | Reaction time/h | Conversion ratio/% |
| A | 0.50 | 33.9 |
| B | 0.50 | 74.0 |
| C | 0.38 | 100.0 |
| D | 0.50 | 79.0 |
| E | 0.50 | 32.6 |
Claims (3)
1. a catalyst that is used for glucose oxidase is characterized in that, it is made up of Au and HTS, and wherein Au is as the main active component of catalyst, and its quality percentage composition is 1.0～8.0%; HTS is as the carrier of catalyst, its quality percentage composition 92.0～99.0%.
2. Preparation of catalysts method that is used for glucose oxidase as claimed in claim 1, it is characterized in that: get 1.0g HTS carrier, 10g/L chlorauric acid solution 2.1 ~ 16.8mL, adding deionized water mixes, place water-bath, be warming up to 60 ℃, transfer pH to 11 ~ 12 with ammoniacal liquor, 100 ~ 110 ℃ were refluxed 1 hour, finish the back suction filtration, 4.0M ammoniacal liquor rinsing 5 ~ 10 minutes, 70 ~ 90 ℃ of hot water of 10 ~ 20mL are taken out and are washed 2 ~ 4 times, the flush away chlorion, 100 ~ 110 ℃ dry 2 hours down, 250 ~ 350 ℃ of following roastings 3 hours in air at last obtain being used for the catalyst of glucose oxidase.
3. using method that is used for the catalyst of glucose oxidase as claimed in claim 1, it is characterized in that: with mass percent concentration is that 5% D/W and the catalyst that is used for glucose oxidase react, the consumption of glucose is 1000:1～1000:8 with the mol ratio that is used for the catalyst nm of gold of glucose oxidase, reaction temperature is 60 ℃, reaction pressure is a normal pressure, with the speed aerating oxygen of 39mL/min, add 0.5mol/L NaOH, make the pH value constant 9.5.
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| CN 201110145833 CN102259024A (en) | 2011-06-01 | 2011-06-01 | Nano Au catalyst for glucose oxidation and preparation and use method thereof |
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| CN 201110145833 CN102259024A (en) | 2011-06-01 | 2011-06-01 | Nano Au catalyst for glucose oxidation and preparation and use method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108218684A (en) * | 2016-12-09 | 2018-06-29 | 中国科学院大连化学物理研究所 | A kind of method of palladium catalyst catalytic oxidation of glucose preparation of gluconic acid and salt |
| CN108383717A (en) * | 2018-04-18 | 2018-08-10 | 中国石油大学(华东) | A kind of preparation method of biomass-based malonic acid |
| CN110790359A (en) * | 2019-10-28 | 2020-02-14 | 井冈山大学 | Method for treating alkaline papermaking wastewater by adopting nanogold catalyst |
-
2011
- 2011-06-01 CN CN 201110145833 patent/CN102259024A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 《American Chemical Society》 19990204 T. Alexander Nijhuis et al. Direct Epoxidation of Propene Using Gold Dispersed on TS-1 and Other Titanium-Containing Supports 第884页右栏第1段至第3段 1-3 第38卷, * |
| 《Catalysis Today》 20070326 Nadine Thielecke et al. Long-term stability of an Au/Al2O3 catalyst prepared by incipient wetness in continuous-flow glucose oxidation 第266页右栏第1段至第267页左栏第3段 3 第122卷, * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108218684A (en) * | 2016-12-09 | 2018-06-29 | 中国科学院大连化学物理研究所 | A kind of method of palladium catalyst catalytic oxidation of glucose preparation of gluconic acid and salt |
| CN108383717A (en) * | 2018-04-18 | 2018-08-10 | 中国石油大学(华东) | A kind of preparation method of biomass-based malonic acid |
| CN108383717B (en) * | 2018-04-18 | 2021-05-11 | 中国石油大学(华东) | Preparation method of biomass-based malonic acid |
| CN110790359A (en) * | 2019-10-28 | 2020-02-14 | 井冈山大学 | Method for treating alkaline papermaking wastewater by adopting nanogold catalyst |
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Application publication date: 20111130 |