CN103524313A - 3,5-dimethylbenzaldehyde preparation method - Google Patents
3,5-dimethylbenzaldehyde preparation method Download PDFInfo
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- CN103524313A CN103524313A CN201310462540.7A CN201310462540A CN103524313A CN 103524313 A CN103524313 A CN 103524313A CN 201310462540 A CN201310462540 A CN 201310462540A CN 103524313 A CN103524313 A CN 103524313A
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- dimethylbenzaldehyde
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
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Abstract
The invention discloses a 3,5-dimethylbenzaldehyde preparation method. The method comprises the steps of mixing, dissolving, reacting, reduced pressure distillation and the like, and allows 3,5-dimethylbenzaldehyde to be prepared through the selective oxidation of mesitylene via the catalytic oxidation effect of a cobalt salt and the coordination effect of a brominated quaternary ammonium salt. The method realizes high raw material conversion rate, high product selectivity, environmentally-friendly reaction process because of the utilization of oxygen as an oxygen source, and high process security because of a reaction pressure being normal pressure or a low pressure. Additionally, the above synthesis method has the advantages of simplicity, simple technologic operation, high yield and low cost.
Description
Technical field
The invention belongs to catalyzed oxidation field, the cobalt salt catalyzed oxidation sym-trimethylbenzene that is specially part participation is prepared 3,5-dimethylbenzaldehyde.
Background technology
3,5-dimethylbenzaldehyde, 3,4-dimethylbenzaldehyde, 2,3-dimethylbenzaldehyde, 2,4-dimethylbenzaldehyde, 2,5-dimethylbenzaldehyde and 2,6-dimethylbenzaldehyde is all important fine-chemical intermediate, all can be applicable to synthetic transparent nucleator for polypropylene, is non-toxic plastic auxiliary agent of new generation, is widely used in packaging material for food production.The transparent nucleator for polypropylene that 3,5-dimethylbenzaldehyde is synthesized is best performance aspect fineness of grain, plastic, transparent, so 3, the synthetic exploitation of 5-dimethylbenzaldehyde comes into one's own.
To so far, at home and abroad in document and patent, report 3,5-dimethylbenzaldehyde main preparation methods has: electrolytic synthesis, organic chemical synthesis method and biological synthesis process.
Electrolytic synthesis is to adopt sym-trimethylbenzene at value Mn (Mn
4+, Mn
3+) oxidation under, by one of them methyl oxidation, be aldehyde radical (CHO), thereby obtain 3,5-dimethylbenzaldehyde, the effect of electricity is to realize manganese (Mn at a low price
2+) be oxidized to value Mn, to guarantee recycling of value Mn.
Organic chemical synthesis method is that to take alcohol, dimethylbenzene, trimethylbenzene and acid etc. be raw material, through catalyzed oxidation or synthetic 3, the 5-dimethylbenzaldehyde of reduction.More successfully wherein to take the chloromethylation process that sym-trimethylbenzene is raw material.
Biological synthesis process is that to take fungi or bacterium be catalytic oxidant, alcohol or sym-trimethylbenzene etc. is oxidized to 3,5-dimethylbenzaldehyde.
All there are certain relative merits in aforesaid method, realize suitability for industrialized production and still have any problem.
Summary of the invention
For solving the deficiencies in the prior art, the object of the present invention is to provide that a kind of preparation method is simple, economical and efficient, transformation efficiency and selectivity high 3, the preparation method of 5-dimethylbenzaldehyde.
For achieving the above object, the present invention is achieved by the following technical solutions:
A kind of 3, the preparation method of 5-dimethylbenzaldehyde, is characterized in that, comprises the following steps:
(1) mix: in reactor, add divalent cobalt and Quaternary ammonium bromide, at room temperature stir, the ratio of the amount of substance that described divalent cobalt and Quaternary ammonium bromide add is 1:0.5-10;
(2) dissolve: under the stirring velocity of turn 400/min, add sym-trimethylbenzene, the amount of substance of divalent cobalt of take is 1mol, the add-on of described sym-trimethylbenzene is 1.4-28L, then, solution is heated to 80-110 ℃, and stirs 20-60min and all dissolve to divalent cobalt and Quaternary ammonium bromide;
(3) reaction: pass into oxygen in solution step (2) Suo Shu under normal pressure, and react 8-24h under the temperature condition of 60-160 ℃; Or solution step (2) Suo Shu is transferred in the autoclave pressure that magnetic stirrer is housed,<u TranNum="77"><</u>under the pressure condition of 0.5Mpa, with after replacement of oxygen at least twice, remain under the temperature condition of 60-160 ℃ and react 8-24h;
(4) underpressure distillation: add alkali lye regulator solution pH value to be greater than 10 after the reacted solution of step (3) is cooling, then Separation of Water oil two-phase, and oil reservoir is through washing, dry, underpressure distillation, and collects 115-125
othe cut of C/20mmHg, obtains 3,5-dimethylbenzaldehyde.
Wherein, described divalent cobalt is CoCl
2.6H
2o or Co (OAc)
2, and described divalent cobalt consumption is 0.5 mol%～10 mol% of sym-trimethylbenzene amount.
Further, the general formula of described Quaternary ammonium bromide is R
1r
2r
3r
4n
+br, wherein said R is alkyl or aryl, and described Quaternary ammonium bromide consumption is 0.5 mol%～20 mol% of sym-trimethylbenzene amount.
And described Quaternary ammonium bromide is Tetrabutyl amonium bromide, four octyl group brometo de amonios, any in didecyl dimethyl brometo de amonio.
In described step (3), while starting to pass into, the speed that passes into of oxygen is 0.5L/min, and after question response causes, the speed that passes into of oxygen is 1L/min.
And the alkali lye described in step (4) is concentration, it is 1 mol/L sodium hydroxide solution.
The invention has the beneficial effects as follows: the present invention has realized the higher conversion of raw material and the highly selective of product, and owing to utilizing oxygen for oxygen source, make reaction process environmental protection, and reaction pressure is normal pressure or low pressure, so process safety is high, in addition, simple synthetic method of the present invention, technological operation is simple, and productive rate is high, and cost is low.
Embodiment
Below in conjunction with specific embodiment, the present invention is carried out to concrete introduction.
embodiment 1:
A kind of 3, the preparation method of 5-dimethylbenzaldehyde, comprises the following steps:
(1) mix: in reactor, add CoCl
2.6H
2o(1 mol%) and TBAB(Tetrabutyl amonium bromide, 1mol%), at room temperature stir;
(2) dissolve: under the stirring velocity of turn 400/min, add sym-trimethylbenzene 400ml, then, solution is heated to 110 ℃, and stir 30min and all dissolve to divalent cobalt and Quaternary ammonium bromide;
(3) reaction: pass into oxygen with 0.5L/min flow velocity under normal pressure in solution step (2) Suo Shu, after question response causes, flow velocity increases to 1L/min, and reacts 11h under the temperature condition of 110-120 ℃;
(4) underpressure distillation: adding concentration after the reacted solution of step (3) is cooling is that the sodium hydroxide solution regulator solution pH value of 1 mol/L is greater than 10, then Separation of Water oil two-phase, and oil reservoir is through washing, dry, underpressure distillation, and collects 115-125
othe cut of C/20mmHg, obtains 3,5-dimethylbenzaldehyde.
The product purity that embodiment 1 prepares is 99%, and reaction conversion ratio 40%, selectivity 72%, separation yield 25%.
Product characterizes:
1h NMR (CDCl
3)
δ9.94 (s, 1H ,-CHO), 7.43 (s, 2H, Ar-H), 7.22 (s, 1H, Ar-H), 2.49 (s, 6H ,-CH
3).
embodiment 2:
A kind of 3, the preparation method of 5-dimethylbenzaldehyde, comprises the following steps:
(1) mix: in reactor, add CoCl
2.6H
2o(1 mol%) with TBAB (Tetrabutyl amonium bromide, 1 mol%), at room temperature stir;
(2) dissolve: under the stirring velocity of turn 400/min, add sym-trimethylbenzene 20ml, then, solution is heated to 110 ℃, and stir 30min and all dissolve to divalent cobalt and Quaternary ammonium bromide;
(3) reaction: solution step (2) Suo Shu is transferred in the autoclave pressure of the 100ml that magnetic stirrer is housed, with replacement of oxygen twice, and remains under the temperature condition of 110 ℃ and react 12h under the pressure condition of 0.3 MPa.
(4) underpressure distillation: adding concentration after the reacted solution of step (3) is cooling is that the sodium hydroxide solution regulator solution pH value of 1 mol/L is greater than 10, then Separation of Water oil two-phase, and oil reservoir is through washing, dry, underpressure distillation, and collects 115-125
othe cut of C/20mmHg, obtains 3,5-dimethylbenzaldehyde.
The product purity that embodiment 2 prepares is 99%, and reaction conversion ratio 84%, selectivity 73%, separation yield 52%.
embodiment 3:
A kind of 3, the preparation method of 5-dimethylbenzaldehyde, comprises the following steps:
(1) mix: in reactor, add Co (OAc)
2(1 mol%) and TOAB (four octyl group brometo de amonios, 2 mol%), at room temperature stir;
(2) dissolve: under the stirring velocity of turn 400/min, add sym-trimethylbenzene 400ml, then, solution is heated to 80 ℃, and stir 30min and all dissolve to divalent cobalt and Quaternary ammonium bromide;
(3) reaction: pass into oxygen with 0.5L/min flow velocity under normal pressure in solution step (2) Suo Shu, after question response causes, flow velocity increases to 1L/min, and reacts 12h under the temperature condition of 80 ℃;
(4) underpressure distillation: adding concentration after the reacted solution of step (3) is cooling is that the sodium hydroxide solution regulator solution pH value of 1 mol/L is greater than 10, then Separation of Water oil two-phase, and oil reservoir is through washing, dry, underpressure distillation, and collects 115-125
othe cut of C/20mmHg, obtains 3,5-dimethylbenzaldehyde.
The product purity that embodiment 3 prepares is 99%, and reaction conversion ratio is 20%, selectivity 97%, yield 18%.
embodiment 4:
A kind of 3, the preparation method of 5-dimethylbenzaldehyde, comprises the following steps:
(1) mix: in reactor, add Co (OAc)
2(1 mol%) and DDAB (didecyl dimethyl brometo de amonio, 1.5 mol%), at room temperature stir;
(2) dissolve: under the stirring velocity of turn 400/min, add sym-trimethylbenzene 400ml, then, solution is heated to 80 ℃, and stir 30min and all dissolve to divalent cobalt and Quaternary ammonium bromide;
(3) reaction: pass into oxygen with 0.5L/min flow velocity under normal pressure in solution step (2) Suo Shu, after question response causes, flow velocity increases to 1L/min, and reacts 12h under the temperature condition of 80 ℃;
(4) underpressure distillation: adding concentration after the reacted solution of step (3) is cooling is that the sodium hydroxide solution regulator solution pH value of 1 mol/L is greater than 10, then Separation of Water oil two-phase, and oil reservoir is through washing, dry, underpressure distillation, and collects 115-125
othe cut of C/20mmHg, obtains 3,5-dimethylbenzaldehyde.
The product purity that embodiment 4 prepares is 99%, and reaction conversion ratio 78%, selectivity 81%, yield 51%.
embodiment 5
A kind of 3, the preparation method of 5-dimethylbenzaldehyde, comprises the following steps:
(1) mix: Co (OAc)
2(1 mol%) and DDAB (didecyl dimethyl brometo de amonio, 1.5 mol%), at room temperature stir;
(2) dissolve: under the stirring velocity of turn 400/min, add sym-trimethylbenzene 20ml, then, solution is heated to 110 ℃, and stir 30min and all dissolve to divalent cobalt and Quaternary ammonium bromide;
(3) reaction: solution step (2) Suo Shu is transferred in the autoclave pressure of the 100ml that magnetic stirrer is housed, with replacement of oxygen twice, and remains under the temperature condition of 110 ℃ and react 12h under the pressure condition of 0.2MPa.
(4) underpressure distillation: adding concentration after the reacted solution of step (3) is cooling is that the sodium hydroxide solution regulator solution pH value of 1 mol/L is greater than 10, then Separation of Water oil two-phase, and oil reservoir is through washing, dry, underpressure distillation, and collects 115-125
othe cut of C/20mmHg, obtains 3,5-dimethylbenzaldehyde.
The product purity that embodiment 5 prepares is 99%, and reaction conversion ratio 89%, selectivity 83%, separation yield 70%.
Other embodiment results are as shown in table 1:
Table 1:
under atmospheric oxygen atmosphere, cobalt salt-Quaternary ammonium bromide catalyzed oxidation sym-trimethylbenzene is prepared 3,5-dimethylbenzaldehyde:
| Sequence number | Catalyzer | Part | Temperature | Selectivity | Yield |
| 1 | CoCl 2· 6H 2O(1.0mol%) | TBAB(0.5mol%) | 120℃ | 61% | 47% |
| 2 | CoCl 2· 6H 2O(1.0mol%) | TBAB(1.0mol%) | 120℃ | 74% | 56% |
| 3 | CoCl 2· 6H 2O(1.0mol%) | TBAB(2.0mol%) | 120℃ | 82% | 59% |
| 4 | CoCl 2· 6H 2O(1.0mol%) | TBAB(3.0mol%) | 120℃ | 83% | 42% |
| 5 | CoCl 2· 6H 2O(0.5mol%) | TBAB(1.0mol%) | 120℃ | 79% | 46% |
| 6 | CoCl 2· 6H 2O(1.5mol%) | TBAB(3.0mol%) | 120℃ | 78% | 52% |
| 7 | CoCl 2· 6H 2O(2.0mol%) | TBAB(4.0mol%) | 120℃ | 84% | 63% |
| 8 | CoCl 2· 6H 2O(1.0mol%) | TBAB(2.0mol%) | 60℃ | 0 | 0 |
| 9 | CoCl 2· 6H 2O(1.0mol%) | TBAB(2.0mol%) | 80℃ | 0 | 0 |
| 10 | CoCl 2· 6H 2O(1.0mol%) | TBAB(2.0mol%) | 100℃ | 90% | 10% |
| 11 | CoCl 2· 6H 2O(1.0mol%) | TBAB(2.0mol%) | 140℃ | 55% | 49% |
| 12 | CoCl 2· 6H 2O(1.0mol%) | TBAB(2.0mol%) | 160℃ | 23% | 26% |
| 13 | CoBr 2· 6H 2O(1.0mol%) | TBAB(2.0mol%) | 120℃ | 69% | 58% |
| 14 | CoCl 2· 6H 2O(1.0mol%) | NH 4Br(2.0mol%) | 120℃ | 57% | 40% |
| 15 | CoCl 2· 6H 2O(1.0mol%) | Didodecyldimethylammbromide bromide (2.0mol%) | 120℃ | 73% | 35% |
| 16 | CoCl 2· 6H 2O(1.0mol%) | DDA (2.0mol%) | 120℃ | 64% | 46% |
| 17 | CoCl 2· 6H 2O(1.0mol%) | Four octyl group brometo de amonios | 120℃ | 75% | 48% |
| 18 | CoCl 2· 6H 2O(1.0mol%) | 4 bromide | 120℃ | 70% | 23% |
| 19 | CoCl 2· 6H 2O(1.0mol%) | Tetramethyl ammonium chloride | 120℃ | 74% | 9% |
From embodiment 1-5 and table 1: prepare 3,5-dimethylbenzaldehyde is colourless or light yellow transparent liquid, there is almond taste, purity is 99%, 221～223 ℃ of its boiling points, 9～10 ℃ of fusing points, are 1.017g/ml the relative densities of 20 ℃, and the higher conversion of raw material and the highly selective of product have been realized, and owing to utilizing oxygen for oxygen source, make reaction process environmental protection, and reaction pressure is normal pressure or low pressure, so process safety is high, in addition, simple synthetic method of the present invention, technological operation is simple, productive rate is high, and cost is low.
The present invention is illustrated according to above-described embodiment, should be appreciated that above-described embodiment does not limit the present invention in any form, and all employings are equal to replaces or technical scheme that equivalent transformation mode obtains, within all dropping on protection scope of the present invention.
Claims (6)
1. one kind 3, the preparation method of 5-dimethylbenzaldehyde, is characterized in that, comprises the following steps:
(1) mix: in reactor, add divalent cobalt and Quaternary ammonium bromide, at room temperature stir, the amount of substance of substrate sym-trimethylbenzene of take is benchmark, the consumption of divalent cobalt is 0.5 mol%～10 mol%, and the consumption of Quaternary ammonium bromide is 0.5 mol%～20 mol%, the ratio of the amount of substance that divalent cobalt and Quaternary ammonium bromide add is 1:0.5-10;
(2) dissolve: under the stirring velocity of turn 400/min, add sym-trimethylbenzene, the amount of substance of divalent cobalt of take is 1mol, the add-on of described sym-trimethylbenzene is 1.4-28L, then, solution is heated to 80-110 ℃, and stirs 20-60min and all dissolve to divalent cobalt and Quaternary ammonium bromide;
(3) reaction: pass into oxygen in solution step (2) Suo Shu under normal pressure, and react 8-24h under the temperature condition of 60-160 ℃; Or solution step (2) Suo Shu is transferred in the autoclave pressure that magnetic stirrer is housed,<u TranNum="354"><</u>under the pressure condition of 0.5Mpa, with after replacement of oxygen at least twice, remain under the temperature condition of 60-160 ℃ and react 8-24h;
(4) underpressure distillation: add alkali lye regulator solution pH value to be greater than 10 after the reacted solution of step (3) is cooling, then Separation of Water oil two-phase, and oil reservoir is through washing, dry, underpressure distillation, and collects 115-125
othe cut of C/20mmHg, obtains 3,5-dimethylbenzaldehyde.
2. according to claim 1 a kind of 3, the preparation method of 5-dimethylbenzaldehyde, is characterized in that, described divalent cobalt is CoCl
2.6H
2o or Co (OAc)
2, and the consumption of described divalent cobalt is 0.5 mol%～10 mol% of sym-trimethylbenzene amount.
3. according to claim 1 a kind of 3, the preparation method of 5-dimethylbenzaldehyde, is characterized in that, the general formula of described Quaternary ammonium bromide is R
1r
2r
3r
4n
+br, wherein said R is alkyl or aryl, and described Quaternary ammonium bromide consumption is 0.5 mol%～20 mol% of sym-trimethylbenzene amount.
4. according to a kind of 3 described in claim 1 or 3, the preparation method of 5-dimethylbenzaldehyde, it is characterized in that, described Quaternary ammonium bromide is Tetrabutyl amonium bromide, four octyl group brometo de amonios, any in didecyl dimethyl brometo de amonio, brometo de amonio, 4 bromide, didodecyldimethylammbromide bromide.
5. according to claim 1 a kind of 3, the preparation method of 5-dimethylbenzaldehyde, is characterized in that, in described step (3), while starting to pass into, the speed that passes into of oxygen is 0.5L/min, and after question response causes, the speed that passes into of oxygen is 1L/min.
6. according to claim 1 a kind of 3, the preparation method of 5-dimethylbenzaldehyde, is characterized in that, described alkali lye is that concentration is 1 mol/L sodium hydroxide solution.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105753672A (en) * | 2016-03-31 | 2016-07-13 | 常州大学 | Synthesis method for 3,5-dimethyl benzaldehyde |
| CN113717037A (en) * | 2021-07-22 | 2021-11-30 | 镇江中智化学科技有限公司 | Green synthesis method of 2, 5-dimethoxybenzaldehyde |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732314A (en) * | 1970-12-07 | 1973-05-08 | Universal Oil Prod Co | Preparation of aromatic aldehydes |
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2013
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732314A (en) * | 1970-12-07 | 1973-05-08 | Universal Oil Prod Co | Preparation of aromatic aldehydes |
Non-Patent Citations (4)
| Title |
|---|
| GABRIELA VALEHRACHOVA ET AL.: "liquid phase oxidation of mesitylene to 3,5-dimethyl-benzaldehyde", 《COLLECTION CZECHOSLOVAK CHERN. COMMUN.》, vol. 51, 31 December 1986 (1986-12-31), pages 2574 - 2581 * |
| MILAN HRONEC ET AL.,: "THE EFFECT OF ACETATES ON THE ACTIVITY OF COBALT BROMIDE CATALYSTS*", 《COLLECTION CZECHOSLOV. CHEM. COMMUN》, vol. 44, 31 December 1979 (1979-12-31), pages 3362 - 3372 * |
| NIMER TAHA ET AL.,: "Co(II) Catalyzed Solvent Free Auto-Oxidation of Methylbenzenes to Substituted Benzoic Acids Under Phase Transfer Conditions", 《CATAL LETT》, vol. 129, 14 February 2009 (2009-02-14), pages 358 - 362, XP019672136 * |
| 刘生丽等: "3，5-二甲基苯甲醛的国内外研究进展", 《甘肃石油和化工》, no. 3, 30 September 2012 (2012-09-30), pages 18 - 22 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105753672A (en) * | 2016-03-31 | 2016-07-13 | 常州大学 | Synthesis method for 3,5-dimethyl benzaldehyde |
| CN113717037A (en) * | 2021-07-22 | 2021-11-30 | 镇江中智化学科技有限公司 | Green synthesis method of 2, 5-dimethoxybenzaldehyde |
| CN113717037B (en) * | 2021-07-22 | 2023-09-12 | 镇江中智化学科技有限公司 | Green synthesis method of 2, 5-dimethoxy benzaldehyde |
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