CN104355982B - A kind of method being prepared oxyacetic acid by glycerine - Google Patents
A kind of method being prepared oxyacetic acid by glycerine Download PDFInfo
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- CN104355982B CN104355982B CN201410479145.4A CN201410479145A CN104355982B CN 104355982 B CN104355982 B CN 104355982B CN 201410479145 A CN201410479145 A CN 201410479145A CN 104355982 B CN104355982 B CN 104355982B
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- oxyacetic acid
- glycerine
- stablizer
- prepared
- oxygenant
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 239000002253 acid Substances 0.000 title claims abstract description 49
- 235000011187 glycerol Nutrition 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 28
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 150000003752 zinc compounds Chemical group 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010525 oxidative degradation reaction Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- UOURRHZRLGCVDA-UHFFFAOYSA-D pentazinc;dicarbonate;hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[O-]C([O-])=O.[O-]C([O-])=O UOURRHZRLGCVDA-UHFFFAOYSA-D 0.000 claims description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 3
- 229940007718 zinc hydroxide Drugs 0.000 claims description 3
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011667 zinc carbonate Substances 0.000 claims description 2
- 235000004416 zinc carbonate Nutrition 0.000 claims description 2
- 229910000010 zinc carbonate Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 238000006731 degradation reaction Methods 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 150000003384 small molecules Chemical class 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000003208 petroleum Substances 0.000 abstract description 2
- 150000003254 radicals Chemical class 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 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
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- -1 hydroxyl free radical Chemical class 0.000 description 1
- JYVNDCLJHKQUHE-UHFFFAOYSA-N hydroxymethyl acetate Chemical compound CC(=O)OCO JYVNDCLJHKQUHE-UHFFFAOYSA-N 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method being prepared oxyacetic acid by glycerine, take glycerine as raw material, water is solvent, under oxygenant and stablizer exist, the oxidative degradation under ultraviolet irradiation condition, obtains described oxyacetic acid; Described stablizer is zinc compounds.The present invention produces free radical by UV-light decompose hydroperoxide, coordinates simultaneously, realize the selective regulation of product with stablizer.The step that present method prepares oxyacetic acid is simple, does not need heating and pressurizing, is easy to control; Oxygenant used and stablizer cheap, degradation process is without the need to organic solvent; Namely the preparation achieving product in a mild condition transforms, and the small-molecule starting material conversion method comparing existing petroleum-based sources has clear superiority, be a kind ofly to have a high potential, environmental protection, efficient economy oxyacetic acid production method.
Description
Technical field
The present invention relates to the preparation method of oxyacetic acid, particularly relate to a kind of method being prepared oxyacetic acid by glycerine of environment-friendly high-efficiency.
Background technology
Oxyacetic acid another name oxyacetic acid or glycolic acid, be the acid of the simplest aliphatic hydroxyl, be mainly present in sugarcane beet and immature grape, but content be lower at occurring in nature.Oxyacetic acid is a kind of important organic synthesis intermediate and Chemicals, and it is of wide application: can be used as clean-out system, sterilant, fiber dyeing agent, purification agent, the batching of welding compound, varnish batching, copper erosion agent, tackiness agent, petroleum demulsifier and metal chelator etc.; Sodium salt, the sylvite of oxyacetic acid can be used as electroplate liquid additive, for the production of organic synthesis platform chemicals such as ethylene glycol; Oxyacetic acid is still for the preparation of the important source material of biological degradation novel material simultaneously.Country is one of basic chemical industry product oxyacetic acid being classified as main exploitation in 10th Five-Year Plan, is enough to illustrate its importance in chemical industry.Domestic oxyacetic acid market potential demand is about 100,000 tons, market value aspect domestic at about 20000 yuan/ton, import at about 30000 yuan/ton.
At present, the technology of preparing of domestic oxyacetic acid mainly contains two kinds of methods.First method is, take Mono Chloro Acetic Acid as raw material, under sodium hydroxide and methyl alcohol exist, be obtained by reacting hydroxy methyl acetate, and then hydrolysis obtains oxyacetic acid.This technical process is long, and yield is low, and has the defects such as the serious and environmental pollution of small scale, equipment corrosion, makes the cost of production oxyacetic acid high.The cyanide process that another kind method is is raw material with formaldehyde and prussic acid (or sodium-chlor), owing to using the prussiate of severe toxicity, in production operation, security requirement is higher.Due to above two kinds of methods be all based on small molecules between conversion prepare oxyacetic acid, technique falls behind, yield poorly, environmental pollution is serious, the second-rate demand that far can not meet market, therefore inhibits widely using of oxyacetic acid to a certain extent.
As can be seen here, based on small-molecule chemical product transform prepare oxyacetic acid also exist at present very large can room for improvement, particularly need the preparation method realizing nontoxic raw material cheap again and environmental protection.Glycerine is the raw material that a kind of wide material sources are cheap again, and it both can be raw material production with natural fats and oils also can be that raw material carrys out chemosynthesis with propylene.Industrialized glycerine price, at 3000-5000 yuan/ton, therefore has larger profit margin with the oxyacetic acid that glycerol production economic worth is at a low price high.
Although be at present that the technology that material oxidation prepares oxyacetic acid has report with glycerine, also depend on expensive precious metal as catalyzer.
Summary of the invention
The invention provides the novel method that oxyacetic acid is prepared in a kind of degraded based on glycerine, raw material sources are extensive, cheap, method environmental protection, and mild condition is simple to operate, be easy to regulating and controlling, and the productive rate of product is very high, has wide industrial prospect.
Prepared a method for oxyacetic acid by glycerine, take glycerine as raw material, water is solvent, under oxygenant and stablizer exist, the oxidative degradation under ultraviolet irradiation condition, obtains described oxyacetic acid; Described stablizer is zinc compounds.
The photochemical reaction of being decomposed with hydrogen peroxide the superoxide being representative by UV-light is the effective ways of the hydroxyl free radical generating strong oxidizing property, in preparation method of the present invention, be produce free radical to glycerine of degrading by ultraviolet catalytic peroxide breakdown, and employ zinc compounds and make stablizer to regulate and control reaction and carry out to generating the direction of oxyacetic acid.
As preferably, described zinc compounds be can in and the zinc oxide of acidic substance, zinc hydroxide, zinc carbonate or zinc subcarbonate.Zinc compounds as stablizer has the effect that selective regulation product generates, preferred several zinc compounds, all can suppress the generation of byproduct formic acid, simultaneously and acidic substance oxyacetic acid thus impel DeR to carry out to the direction generating oxyacetic acid.
As preferably, described oxygenant and the mass ratio of glycerine are 0.5 ~ 10:1; Described stablizer and the mass ratio of glycerine are 0.2 ~ 2:1.Oxygenant is crossed and is decomposed not exclusively at least, and crossing by-products content at most increases; It is poor that selectivity of product at least crossed by zinc class stablizer, and too high then speed of reaction is on the low side.Only under above-mentioned optimum condition, rate of decomposition can reach best with selectivity of product.
As preferably, the superoxide of described oxygenant to be general formula be R-O-O-R', wherein, R and R' is independently selected from H, C
1~ C
5alkyl or metal ion.Carbon number is selected to be less than the alkyl of 5 to guarantee the solubleness of oxygenant in water.
Carry out in ultraviolet lighting degradation process, illumination condition is: the power of light source is 100 ~ 1000W, and light application time is 1 ~ 10h.
According to above-mentioned reason, more preferably:
Described oxygenant is hydrogen peroxide or sodium peroxide;
Described oxygenant and the mass ratio of glycerine are 1 ~ 5:1; Described stablizer and the mass ratio of glycerine are 0.5 ~ 1:1;
Described ultraviolet lamp wavelength is 365nm, and power is 500W, and light application time is 3 ~ 5h.
The productive rate of the oxyacetic acid prepared under above-mentioned optimum condition can up to 77%.
The product that oxidative degradation under ultraviolet irradiation condition obtains also needs to carry out separation and purification.After testing, degraded product of the present invention mainly oxyacetic acid and byproduct formic acid.Because oxyacetic acid fusing point is 75 ~ 80 DEG C and difficult volatilization, and formic acid boiling point is lower and volatile.Therefore formic acid can be separated by the method for distillation or underpressure distillation at about 80 DEG C.And metal salt catalyst remaining in solution can be removed by adding the method precipitation of basic cpd as soda ash; Also according to metal-salt and oxyacetic acid solvability difference in organic solvent, repeatedly can extract by adding ethyl acetate and purify.
Compared with prior art, tool of the present invention has the following advantages:
The present invention is with wide material sources, and cheap glycerine is raw material, and using water as solvent, reaction belongs to homogeneous reaction, is therefore swift in response and thoroughly.
The present invention select can in and the zinc compounds of acidic substance be stablizer, on the one hand and acidic substance oxyacetic acid thus impel DeR to carry out to the direction generating oxyacetic acid, suppress the generation of byproduct formic acid simultaneously, therefore can obtain the oxyacetic acid of high yield.
The step of present method is simple, is easy to control, and not with an organic solvent, and without the need to heating and pressurizing, achieve the condition gentleer than the precious metal catalyst method of existing production technique and bibliographical information, be a kind of oxyacetic acid production method of efficient economy to degradation process.
Embodiment
For a better understanding of the present invention, set forth technical scheme of the present invention further below in conjunction with embodiment, but content of the present invention is not only confined to the following examples.
The present embodiment glycerine used is business-like product and not purified direct use.
The photodegradation reaction of glycerine is carry out in the disc open glass container of 10cm at a diameter.The underlying magnetic agitation of container, whole reactor is placed in immediately below ultraviolet lamp source, and ultraviolet lamp wavelength is 365nm, and power is 500W, and the distance bottom Glass Containers and between ultraviolet lamp source is 15cm.
Embodiment 1
First 3g glycerine is placed in the disc Glass Containers filling 30ml water, then container is placed in water-bath.Adding 15mL mass concentration is again the hydrogen peroxide of 30% and the zinc oxide of 1.5g, starts magnetic agitation, and rotating speed is 200rpm, after container is placed in irradiation under UV-light, the irradiation-induced degradation time is 3 hours.
Removed by undissolved solid filtering after having reacted, filtrate oxyacetic acid productive rate is by analysis 77%.
Embodiment 2
First 3g glycerine is placed in the disc Glass Containers filling 30ml water, then container is placed in water-bath.Adding 20mL mass concentration is again the hydrogen peroxide of 30% and the zinc hydroxide of 2g, starts magnetic agitation, and rotating speed is 200rpm, after container is placed in irradiation under UV-light, the irradiation-induced degradation time is 5 hours.
Removed by undissolved solid filtering after having reacted, filtrate oxyacetic acid productive rate is by analysis 71%.
Embodiment 3
First 3g glycerine is placed in the disc Glass Containers filling 30ml water, then container is placed in water-bath.Adding 15mL mass concentration is again the hydrogen peroxide of 30% and the zinc subcarbonate of 3g, starts magnetic agitation, and rotating speed is 200rpm, after container is placed in irradiation under UV-light, the irradiation-induced degradation time is 5 hours.
Removed by undissolved solid filtering after having reacted, filtrate oxyacetic acid productive rate is by analysis 68%.
Claims (7)
1. prepared a method for oxyacetic acid by glycerine, it is characterized in that, take glycerine as raw material, water is solvent, under oxygenant and stablizer exist, the oxidative degradation under ultraviolet irradiation condition, obtains described oxyacetic acid; Described stablizer is zinc compounds;
Described zinc compounds is zinc oxide, zinc hydroxide, zinc carbonate or zinc subcarbonate.
2. the method being prepared oxyacetic acid by glycerine according to claim 1, is characterized in that, described oxygenant and the mass ratio of glycerine are 0.5 ~ 10:1;
Described stablizer and the mass ratio of glycerine are 0.2 ~ 2:1.
3. the method being prepared oxyacetic acid by glycerine according to claim 2, is characterized in that, the superoxide of described oxygenant to be general formula be R-O-O-R', wherein, R and R' is independently selected from H, C
1~ C
5alkyl or metal ion.
4. the method being prepared oxyacetic acid by glycerine according to claim 3, is characterized in that, described oxygenant is hydrogen peroxide or sodium peroxide.
5. the method being prepared oxyacetic acid by glycerine according to claim 4, is characterized in that, the mass ratio of described oxygenant and glycerine is 1 ~ 5:1.
6. the method being prepared oxyacetic acid by glycerine according to claim 5, is characterized in that, described stablizer and the mass ratio of glycerine are 0.5 ~ 1:1.
7. the method being prepared oxyacetic acid by glycerine according to claim 1, is characterized in that, described illumination condition is: the power of light source is 100 ~ 1000W, and light application time is 1 ~ 10h.
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| CN201410479145.4A CN104355982B (en) | 2014-09-18 | 2014-09-18 | A kind of method being prepared oxyacetic acid by glycerine |
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| CN201410479145.4A CN104355982B (en) | 2014-09-18 | 2014-09-18 | A kind of method being prepared oxyacetic acid by glycerine |
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| CN104355982B true CN104355982B (en) | 2016-03-30 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2610257C1 (en) * | 2015-11-19 | 2017-02-08 | Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский Томский государственный университет" (ТГУ, НИ ТГУ) | Method for separating glycolic acid from mixed glyoxal disproportionation products |
| CN106977391B (en) * | 2017-04-25 | 2019-12-24 | 中国科学院宁波材料技术与工程研究所 | Method for preparing glycolic acid from glycerol |
| CN115246770B (en) * | 2021-04-26 | 2023-11-17 | 四川大学 | Method for preparing glycolic acid by catalytic conversion of glycerol |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101184717A (en) * | 2005-05-27 | 2008-05-21 | 旭化成化学株式会社 | Method for producing glycolic acid |
| JP2009137891A (en) * | 2007-12-06 | 2009-06-25 | Lion Corp | Method for producing dihydroxyacetone or glycolic acid |
| JP2011016782A (en) * | 2009-07-10 | 2011-01-27 | Lion Corp | Method for producing glycolic acid, and glycolic acid-containing composition |
| CN103025698A (en) * | 2010-06-25 | 2013-04-03 | 卡迪夫大学学院顾问有限公司 | Selective oxidation of hydrocarbons using heterogeneous catalysts |
-
2014
- 2014-09-18 CN CN201410479145.4A patent/CN104355982B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101184717A (en) * | 2005-05-27 | 2008-05-21 | 旭化成化学株式会社 | Method for producing glycolic acid |
| JP2009137891A (en) * | 2007-12-06 | 2009-06-25 | Lion Corp | Method for producing dihydroxyacetone or glycolic acid |
| JP2011016782A (en) * | 2009-07-10 | 2011-01-27 | Lion Corp | Method for producing glycolic acid, and glycolic acid-containing composition |
| CN103025698A (en) * | 2010-06-25 | 2013-04-03 | 卡迪夫大学学院顾问有限公司 | Selective oxidation of hydrocarbons using heterogeneous catalysts |
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