CN104892390A - Methoxyactic acid preparation method - Google Patents
Methoxyactic acid preparation method Download PDFInfo
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- CN104892390A CN104892390A CN201510182906.4A CN201510182906A CN104892390A CN 104892390 A CN104892390 A CN 104892390A CN 201510182906 A CN201510182906 A CN 201510182906A CN 104892390 A CN104892390 A CN 104892390A
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- preparation
- methoxyactic
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- methoxyacetic acid
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- 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
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a methoxyactic acid preparation method, wherein Pt/C is adopted as a catalyst, oxygen is adopted as an oxidant, water is adopted as a solvent, and 2-methoxyethanol oxidation is performed to prepare the methoxyactic acid in a one-step manner. Compared with the method in the prior art, the method of the present invention has the following advantages that (1) the used solvent is the water with characteristics of low price, easy obtaining and green environmental protection, such that environment pollution can not generated; (2) the used catalyst Pt/C has the high catalysis efficiency, and can be reused only through the simple filtration after completing the reaction; (3) the reaction conditions are mild, and the operation is operate; and (4) the used oxidant is the O2 with characteristics of safety, environmental protection, low price and easy obtaining, such that waste gas and waste liquid can not be generated.
Description
Technical field
The present invention relates to a kind of preparation method of methoxyacetic acid, particularly relate to Pt/C as catalyzer, oxygen is as oxygenant, and water is as the method preparing methoxyacetic acid of solvent.
Background technology
Methoxyacetic acid is a kind of important Organic Chemicals, and it and methyl alcohol synthesize the intermediate methoxy menthyl acetate with important value by esterification, this intermediate both can be used for the kinetic resolution of Chiral Amine compounds, can be used for vitamins B again
6, sulfanilamide (SN)-5-pyrimidine etc. synthesis; In addition, methoxyacetic acid can also for the preparation of methoxyacetyl chloride, and this material has important use in plant protection and medicine industry.The preparation of current methoxyacetic acid is mainly through substitution reaction and oxidizing reaction two kinds of approach.
Patent US4968840 discloses a kind of method being prepared methoxyacetic acid by substitution reaction, the method take methyl alcohol as solvent, Mono Chloro Acetic Acid and sodium methylate react in a heated condition, react complete removing methyl alcohol, add methoxy menthyl acetate, pass into dry hydrogen chloride gas and carry out acidifying, this preparation method's technical process is loaded down with trivial details, and acidization is consuming time longer, hydrogen chloride gas heavy corrosion production unit, bring enormous pressure to maintenance of the equipment, produce comprehensive cost higher.
Patent CN101979372 discloses a kind of method being prepared methoxyacetic acid by oxidizing reaction, the method take ethylene glycol monomethyl ether as raw material, industrial nitric acid is oxygenant, oxidizing reaction is carried out under cupric chloride catalysis, the amount of nitric acid needed for this reaction is 1.2-3 times of ethylene glycol monomethyl ether, excessive nitric acid is difficult to reclaim, and the oxides of nitrogen gas that reaction produces is difficult to purification, contaminate environment.
For the deficiency of above-mentioned two class synthetic methods, especially on the grievous injury of equipment and the pollution problem of environment, need design one badly more easy, the methoxyacetic acid production technique of safety and environmental protection, to adapt to the requirement that modern industrialization is produced.
Summary of the invention
The object of the invention is the synthesis theory according to Green Chemistry, provides a kind of high-level efficiency, easily realizes the synthetic method of the high purity methoxyacetic acid (>=99%) of suitability for industrialized production.
Technical scheme provided by the invention is: a kind of preparation method of methoxyacetic acid, take Pt/C as catalyzer, and oxygen is oxygenant, and water, as solvent, obtains methoxyacetic acid by ethylene glycol monomethyl ether being oxidized a step.
Described catalyzer is the Pt/C of mass percent 5%.
The volume ratio of described water and ethylene glycol monomethyl ether is 1.0-2.0:1.0.
Mass ratio between described Pt/C and ethylene glycol monomethyl ether is 0.005-0.015:1.0.
Described oxygen pressure is 0.5-1.0 MPa.
Described temperature of reaction is 60-80 DEG C.
Described reaction times 6-10 h.
Reaction formula of the present invention is as follows:
Compared with prior art, of the present invention and preparation method's tool have the following advantages:
(1) solvent for use is water that is cheap and easy to get, environmental protection, non-environmental-pollution.
(2) used catalyst Pt/C catalytic efficiency is high, by simple filtration and reusable after having reacted.
(3) reaction conditions is gentle, easy and simple to handle.
(4) oxygenant used is safety and environmental protection O cheap and easy to get
2, without the generation of waste gas and waste liquid.
Embodiment
To contribute to understanding the present invention by following embodiment, but content of the present invention can not be limited.
Embodiment 1
By ethylene glycol monomethyl ether 30 mL(28.8 g), deionized water 40 mL and Pt (5wt%)/C catalyst 0.25 g adds in autoclave, regulates O
2pressure makes the pressure of reactor maintain 0.6 MPa, and 70 DEG C of reactions 7 hours, question response still was cooled to room temperature, filtration, washing and recycling catalyzer, filtrate decompression is distilled, and collects 92-94 DEG C/10 mmHg cuts, obtain methoxyacetic acid 30.35g, yield 91%, purity 99%.
Embodiment 2
By ethylene glycol monomethyl ether 30 mL(28.8 g), deionized water 30 mL and Pt (5wt%)/C catalyst 0.15 g is incorporated in autoclave, regulates O
2pressure makes the pressure of reactor maintain 0.5 MPa, and 60 DEG C of reactions 6 hours, question response still was cooled to room temperature, filtration, washing and recycling catalyzer, filtrate decompression is distilled, and collects 92-94 DEG C/10 mmHg cuts, obtain methoxyacetic acid 30.69 g, yield 90%, purity 99%.
Embodiment 3
By ethylene glycol monomethyl ether 30 mL(28.8 g), deionized water 45 mL and Pt (5wt%)/C catalyst 0.32 g, in autoclave, regulates O
2pressure makes the pressure of reactor maintain 0.8 MPa, and 80 DEG C of reactions 6 hours, question response still was cooled to room temperature, filtration, washing and recycling catalyzer, filtrate decompression is distilled, and collects 92-94 DEG C/10 mmHg cuts, obtain methoxyacetic acid 31.37 g, yield 92%, purity 99%.
Embodiment 4
By ethylene glycol monomethyl ether 30 mL(28.8 g), deionized water 60 mL and Pt (5wt%)/C catalyst 0.43 g, in autoclave, regulates O
2pressure makes the pressure of reactor maintain 1.0 MPa, and 80 DEG C of reactions 10 hours, question response still was cooled to room temperature, filtration, washing and recycling catalyzer, filtrate decompression is distilled, and collects 92-94 DEG C/10 mmHg cuts, obtain methoxyacetic acid 32.74 g, yield 96%, purity 99%.
Embodiment 5
By ethylene glycol monomethyl ether 30 mL(28.8 g), deionized water 50 mL and Pt (5wt%)/C catalyst 0.38 g, in autoclave, regulates O
2pressure makes the pressure of reactor maintain 0.7 MPa, and 70 DEG C of reactions 8 hours, question response still was cooled to room temperature, filtration, washing and recycling catalyzer, filtrate decompression is distilled, and collects 92-94 DEG C/10 mmHg cuts, obtain methoxyacetic acid 31.71 g, yield 93%, purity 99%.
Embodiment 6
According to embodiment 4 condition, after completion of the reaction, the catalyzer of recovery is carried out drying, then repeat embodiment 4 condition as catalyzer and test, multiplicity 10 times, methoxyacetic acid yield is between 93%-96%, and purity reaches 99%.
Claims (6)
1. a preparation method for methoxyacetic acid, with the Pt/C of mass percent 5% for catalyzer, oxygen is oxygenant, and water, as solvent, obtains methoxyacetic acid by ethylene glycol monomethyl ether being oxidized a step.
2. preparation method according to claim 1, is characterized in that: the volume ratio of water and ethylene glycol monomethyl ether is 1.0-2.0:1.0.
3. preparation method according to claim 1 and 2, is characterized in that: the mass ratio between P/C and ethylene glycol monomethyl ether is 0.005-0.015:1.0.
4. preparation method according to claim 1 and 2, is characterized in that: oxygen pressure is 0.5-1.0 MPa.
5. preparation method according to claim 1 and 2, is characterized in that: temperature of reaction is 60-80
oc.
6. preparation method according to claim 1 and 2, is characterized in that: reaction times 6-10 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510182906.4A CN104892390A (en) | 2015-04-17 | 2015-04-17 | Methoxyactic acid preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510182906.4A CN104892390A (en) | 2015-04-17 | 2015-04-17 | Methoxyactic acid preparation method |
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| Publication Number | Publication Date |
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| CN104892390A true CN104892390A (en) | 2015-09-09 |
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| CN201510182906.4A Pending CN104892390A (en) | 2015-04-17 | 2015-04-17 | Methoxyactic acid preparation method |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018001861A1 (en) | 2016-06-28 | 2018-01-04 | Basf Se | Method for producing 2-methoxyacetic acid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2936123A1 (en) * | 1979-09-07 | 1981-04-02 | Hoechst Ag, 6000 Frankfurt | METHOD FOR PRODUCING ALKOXY ACETIC ACIDS |
| DE3135946A1 (en) * | 1981-09-10 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Process for preparing alkoxyacetic acids |
| CN101979372A (en) * | 2010-10-31 | 2011-02-23 | 江苏省原子医学研究所 | Preparation method of methoxyacetic acid |
-
2015
- 2015-04-17 CN CN201510182906.4A patent/CN104892390A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2936123A1 (en) * | 1979-09-07 | 1981-04-02 | Hoechst Ag, 6000 Frankfurt | METHOD FOR PRODUCING ALKOXY ACETIC ACIDS |
| DE3135946A1 (en) * | 1981-09-10 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Process for preparing alkoxyacetic acids |
| CN101979372A (en) * | 2010-10-31 | 2011-02-23 | 江苏省原子医学研究所 | Preparation method of methoxyacetic acid |
Non-Patent Citations (1)
| Title |
|---|
| EKAMBARAM BALARAMAN,ET AL.,: "Catalytic transformation of alcohols to carboxylic acid salts and H2 using water as the oxygen atom source", 《NATURE CHEMISTRY》, vol. 5, 28 February 2013 (2013-02-28), pages 122 - 125 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018001861A1 (en) | 2016-06-28 | 2018-01-04 | Basf Se | Method for producing 2-methoxyacetic acid |
| US11104634B2 (en) | 2016-06-28 | 2021-08-31 | Basf Se | Method for producing 2-methoxyacetic acid |
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Application publication date: 20150909 |
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