CN105541588A - Synthesis method of butanedione - Google Patents
Synthesis method of butanedione Download PDFInfo
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- CN105541588A CN105541588A CN201610104462.7A CN201610104462A CN105541588A CN 105541588 A CN105541588 A CN 105541588A CN 201610104462 A CN201610104462 A CN 201610104462A CN 105541588 A CN105541588 A CN 105541588A
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- 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
- B01J31/165—Polymer immobilised coordination complexes, e.g. organometallic complexes
- B01J31/1658—Polymer immobilised coordination complexes, e.g. organometallic complexes immobilised by covalent linkages, i.e. pendant complexes with optional linking groups, e.g. on Wang or Merrifield resins
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- 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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- 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
- C07C45/37—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 >C—O—functional groups to >C=O groups
- C07C45/39—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 >C—O—functional groups to >C=O groups being a secondary hydroxyl group
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- B01J2231/76—Dehydrogenation
- B01J2231/763—Dehydrogenation of -CH-XH (X= O, NH/N, S) to -C=X or -CX triple bond species
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
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Abstract
The invention discloses a synthesis method of butanedione. According to the synthesis method, a salicylaldehyde derivative reacts with compounds of diamine to generate a schiff base ligand, then coordination with a transition metal salt solution is conducted to prepare metal schiff base complexes, then an F-C acylation reaction is conducted, the metal schiff base complexes are immobilized in a polystyrene microsphere carrier containing an acyl group to be prepared into an immobilized catalyst, and finally acetoin serves as a raw material and is added to the immobilized catalyst, air is introduced for catalytic oxidation, and the butanedione is obtained. According to the synthesis method, the F-C acylation reaction is conducted, the metal schiff base complexes are immobilized in the polystyrene microsphere carrier containing the acyl group, the immobilization rate of the immobilized metal schiff base complexes is raised through chemical bonds, posttreatment of a product obtained through the immobilized catalyst is simple, and the yield of is high; besides, the adopted raw material is the acetoin, production cost is lowered for enterprises producing the acetoin, product diversity is increased, and enterprise competitiveness can be improved.
Description
Technical field
The present invention relates to catalyst preparation field, particularly a kind of synthetic method of dimethyl diketone.
Background technology
Dimethyl diketone (2,3-Butanedione), be also called two second phthalein, for yellow-green liquid, there is cream, butter fragrance, boiling point 88.0 ~ 89.0 DEG C, it is a kind of important flavoring compounds, natural goods form is present in the essential oils such as Radix Angelicae Sinensis, lily magnolia, lavandula angustifolia, cardamom, lemongrass, at cream, is also detected in milk, coffee, fruit, tomato, grape wine.It is mainly used in food spice additive, and preparation milk flavoured type essence for food, Feed Flavourings, also can be used on oleomargarine, cheese, chocolate, coffee, cocoa, cheese, sugar, XIANGJIALANDOU, honey, cocoa, Lang Mu, nut, almond etc.Also can make an addition in fresh fruit used for cosmetic perfume or novel essence by trace.
At present both at home and abroad the production line of dimethyl diketone mainly can be divided into: (1) direct extraction method: this method be contain the plant of this spices with nature Ye Hua etc. for raw material, the mode extracted by organic solvent extraction is obtained, can not extract on a large scale because occurring in nature content is limited, therefore suitability for industrialized production is restricted.(2) biological fermentation process: this method is referred in the microbe metabolite utilizing specific microorganism to take carbohydrate as raw material to be obtained by fermentation form containing a small amount of dimethyl diketone, because this method desired microorganisms cultivates inconvenience, and the dimethyl diketone content in metabolite is less than 5% very little, extract difficulty, present stage, output was not very high, also had very large development space.(3) chemical oxidization method: utilize the mode of chemosynthesis to prepare, mainly comprise and shine ozone oxidation agent by titanium dioxide, transition metal salt and hydrogen peroxide, Sodium Nitrite, in the composition catalyst of copper and air, the oxygenant such as oxygen and catalyst oxidation 2-butanone obtain dimethyl diketone, or pass through with methyl nitrite and Lewis hydrochlorate-phosphoric acid-hydrochloric acid catalyst catalysis oximation reaction, again through crystallization, hydrolysis, distillation, the treating processess such as Calcium Chloride Powder Anhydrous dehydration prepare the synthetic methods such as dimethyl diketone, it is very loaded down with trivial details that these chemical oxidation method operating process have, raw material consumption is also many, oxygenant used in addition has certain hazardness to the water and soil in environment, some productive rates are not very high, also lower by product is more causes separation difficulty for selectivity, also uneconomical economically.
Summary of the invention
For overcoming the deficiencies in the prior art, the invention provides a kind of synthetic method of dimethyl diketone.
For achieving the above object, technical scheme of the present invention is:
A kind of synthetic method of solid-supported catalyst; salicylaldehyde derivatives and diamine compounds are reacted and generates schiff base ligand; prepare Metal Schiff _ base title complex with coordinate transition metal salts again, then on the polystyrene microsphere carrier containing acyl group, obtain solid-supported catalyst by immobilized for Metal Schiff _ base title complex by F-C acylation reaction.
The present invention by F-C acylation reaction by immobilized for Metal Schiff _ base title complex on the polystyrene microsphere carrier containing acyl group; the immobilized rate of immobilized Metal Schiff _ base title complex is improve by chemical bond; the product aftertreatment obtained by supported catalyzer is simple, and productive rate is high.
The present invention reacts with salicylaldehyde derivatives and diamine compounds and generates schiff base ligand, and preparation method is simple, and structure is easily modified, and selectivity is good, and its special construction has the katalysis of good oxygen carrier, antibacterial and simulation biological enzyme.
Preferably, step is as follows:
(1) salicylaldehyde derivatives and diamine compounds are reacted generate schiff base ligand, then prepare Metal Schiff _ base title complex with coordinate transition metal salts;
(2) the Metal Schiff _ base title complex of preparation is dissolved in a solvent, add chlorine acyl group polystyrene microsphere, after reacting by heating, obtain solid-supported catalyst;
Preferred further, the concrete steps of described step (1) are: joined by salicylaldehyde derivatives in the reaction vessel containing solvent 1, by heating in water bath, salicylaldehyde derivatives is dissolved, under the condition stirred, maintain solution temperature is 50-90 DEG C, dropwise drip diamine compounds, after dropwising back flow reaction 1.5-2.5h, prepare schiff base ligand through filtering and washing drying; Again be dissolved in by schiff base ligand in the reaction vessel containing solvent 2, start to drip transition metal salt solution, suction filtration crystallization after back flow reaction 2-3h, vacuum-drying obtains Metal Schiff _ base title complex.
Further preferred, the substituting group of described salicylaldehyde derivatives is methyl, the tertiary butyl, methoxyl group, preferred tertiary butyl; Described diamine compounds is quadrol, cyclohexanediamine or phenylenediamine, preferred phenylenediamine; Described transition metal salt is mantoquita, zinc salt, nickel salt or cobalt salt.
Further preferred, the mol ratio of described salicylaldehyde derivatives and diamine derivative is: 2.0-2.5:1, preferred molar ratio 2.2:1; The mol ratio of described transition metal and diamine compounds is 1.1-1.3:1.
Further preferred, the solvent 1 in described step (1) is methyl alcohol, ethanol or sherwood oil, preferred alcohol; Described solvent 2 is methyl alcohol or ethanol.
Further preferred, described solution temperature is 60 DEG C.
Further preferred, described vacuum drying temperature is 60-80 DEG C.
Further preferred, described vacuum drying temperature is 65 DEG C.
Preferred further, the particle diameter of described chlorine acyl group polystyrene microsphere is 3-5 μm.Particle diameter is excessive, and surface-area diminishes, supported quantity step-down; Particle diameter is too small, be then not easy filtered and recycled.
Preferred further, the temperature of reaction of described step (2) is 40 ~ 80 DEG C, and the described reaction times is 5-8h.
Further preferred, the temperature of reaction of described step (2) is 50 DEG C.The speed reacted at such a temperature and reaction by product less.
Preferred further, the addition of described chlorine acyl group polystyrene microsphere is react used 2-2.5 times.
A kind of solid-supported catalyst utilizing aforesaid method to prepare.
The application of a kind of above-mentioned solid-supported catalyst in synthesis dimethyl diketone.
A synthetic method for dimethyl diketone, is that raw material adds above-mentioned solid-supported catalyst with acetoin, passes into air catalytic oxidation and obtain dimethyl diketone.Raw material of the present invention is acetoin, for the enterprise of production acetoin, reduces production cost, adds product diversity, can improve the competitive power of enterprise.
Preferably, solvent is dimethyl formamide.
Preferably, the addition of described solid-supported catalyst is 2-5% (molar percentage).
Preferably, described air passes into speed is 2-5L/min.Pass into the more difficult control of amount of air, after adding immobilized Metal Schiff _ base title complex, the air passing into 2-5L/min can meet the amount of oxygen of oxidising process completely, thus both reduces cost, in turn saves resource.
Preferably, described temperature of reaction is 60-90 DEG C.
Compared with prior art, Advantageous Effects of the present invention is:
1, the present invention adopts and first prepares solid-carried catalyst, and the preparation flow of catalyzer is simple, and catalytic efficiency is high, and reaction after product is easy to be separated with catalyzer, alleviates aftertreatment burden.
2, catalyzer can be reused the oxidation of catalysis acetoin and prepares dimethyl diketone, effectively reduces the production cost that catalyzer brings.
3, the oxygenant in reaction is the oxygen in air, is reached the object of oxidation by the speed controlling to pass into, and while reducing production cost, anaerobic agent remains in the reaction is the more green mode of production.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described.
Embodiment 1
1) preparation of catalyzer
200ml alcohol solvent is added in three mouthfuls of round-bottomed flasks of 500ml, add 30g3-cresotinic acid aldehyde, heating in water bath makes cresotinic acid aldehyde dissolve gradually, under the condition stirred, solution temperature maintains 60 DEG C and starts to drip quadrol 6g, solution colour gradually becomes reddish-brown, dropwise, through crystallisation by cooling suction filtration after maintenance stirring 2h, washing with alcohol 2 times, obtain the part crystal of reddish-brown, this crystal is dissolved in 100ml methyl alcohol, start under agitation condition to drip copper nitrate solution 60ml (concentration 2mol/L), dropwise solid to separate out, backflow 2h, through suction filtration, methanol wash, at 65 DEG C, vacuum-drying obtains catalyzer, productive rate is 89.9%.
2) catalyzer is immobilized
The catalyzer 0.05mol prepared is dissolved in 150ml tetrahydrofuran (THF), and adds the chlorine acyl group polystyrene microsphere that 50g particle diameter is 3-5 μm, under 50 DEG C of conditions, stirring reaction 8h, filters, washing, dries 5h prepare supported catalyzer at 90 DEG C.
3) preparation of dimethyl diketone
0.15mol acetoin is joined in the 250ml there-necked flask containing 150mlDMF, and add the supported catalyzer of 20g, by air compression plant, start to pass into air, the speed of air is 5L/min, 5h is reacted under the condition of 50 DEG C, react complete, after filtration, washing catalyst is reused in reaction next time and goes, remaining reaction solution removes unnecessary solvent through decompression, and yield is 92.1%.Object product is obtained again through rectifying.
Embodiment 2
1) preparation of catalyzer
200ml alcohol solvent is added in three mouthfuls of round-bottomed flasks of 500ml, add 39.2g3-tertiary butyl salicylic aldehyde, heating in water bath makes 3-tertiary butyl salicylic aldehyde dissolve gradually, under the condition stirred, solution temperature maintains 60 DEG C and starts to drip cyclohexyl diamine 11.4g, dropwise, through crystallisation by cooling suction filtration after continuation stirring 2h, washing with alcohol 2 times, this crystal is dissolved in 100ml methyl alcohol, start under agitation condition to drip copper nitrate solution 60ml (concentration 2mol/L), dropwise solid to separate out, backflow 2h, through suction filtration, methanol wash, at 65 DEG C, vacuum-drying obtains catalyzer, productive rate is 90.5%.
2) catalyzer is immobilized
The catalyzer 0.05mol prepared is dissolved in 150ml petroleum ether solution, and adds the chlorine acyl group polystyrene microsphere that 50g particle diameter is 3-5 μm, under 50 DEG C of conditions, stirring reaction 8h, filters, washing, dries 5h prepare supported catalyzer at 90 DEG C.
3) preparation of dimethyl diketone
0.15mol acetoin is joined in the 250ml there-necked flask containing 150mlDMF, and add the supported catalyzer of 20g, by air compression plant, start to pass into air, the speed of air is 4L/min, 3h is reacted under the condition of 60 DEG C, react complete, after filtration, washing catalyst is reused in reaction next time and goes, remaining reaction solution removes unnecessary solvent through decompression, and yield is 93.2%.Rectifying obtains object product again.
Embodiment 3
1) preparation of catalyzer
200ml alcohol solvent is added in three mouthfuls of round-bottomed flasks of 500ml, add 51.9g3, 5-di-tert-butyl salicylaldehyde, heating in water bath makes 3 gradually, 5-di-tert-butyl salicylaldehyde dissolves, under the condition stirred, solution temperature maintains 60 DEG C and starts to drip O-Phenylene Diamine 10.8g, dropwise, through crystallisation by cooling suction filtration after maintenance stirring 2h, washing with alcohol 3 times, this crystal is dissolved in 100ml methyl alcohol, start under agitation condition to drip cobalt nitrate solution 100ml (concentration 1mol/L), dropwise solid to separate out, backflow 2h, through suction filtration, methanol wash, at 65 DEG C, vacuum-drying obtains catalyzer, productive rate is 90.5%.
2) catalyzer is immobilized
The catalyzer 0.25mol prepared is dissolved in 150ml diethyl ether solution, and adds the Chloromethyl polystyrene that 50g particle diameter is 3-5 μm, under 30 DEG C of conditions, stirring reaction 8h, filters, and washs and prepares supported catalyzer at 90 DEG C of oven dry 5h.
3) preparation of dimethyl diketone
0.05mol acetoin is joined in the 250ml there-necked flask of 150mlDMF, and add the supported catalyzer of 20g, by air compression plant, start to pass into air, the speed of air is 3L/min, 3h is reacted under the condition of 50 DEG C, react complete, after filtration, washing catalyst is reused in reaction next time and goes, remaining reaction solution removes unnecessary solvent through decompression, and yield is 94.8%.Object product is obtained again through rectifying.
Embodiment 4
1) preparation of catalyzer
200ml petroleum ether solvent is added in three mouthfuls of round-bottomed flasks of 500ml, add 30g3-cresotinic acid aldehyde, heating in water bath makes it dissolve gradually, quadrol is dripped under the condition stirred, solution colour gradually becomes reddish-brown, through crystallisation by cooling filtering and washing, obtain the part crystal of reddish-brown, this crystal is dissolved in 100ml methyl alcohol, starts under agitation condition to drip nickel nitrate solution 110ml (concentration 1mol/L), dropwise backflow 2h, through suction filtration, methanol wash, at 65 DEG C, vacuum-drying obtains catalyzer, and productive rate is 69.9%.
2) catalyzer is immobilized
The catalyzer 0.25mol prepared is dissolved in 150ml ethanolic soln, and adds the Chloromethyl polystyrene that 50g particle diameter is 3-5 μm, under 50 DEG C of conditions, stirring reaction 8h, filters, and washs and prepares supported catalyzer at 90 DEG C of oven dry 5h.
3) preparation of dimethyl diketone
0.15mol acetoin is joined in the 250ml there-necked flask of 150mlDMF, and add the supported catalyzer of 20g, by air compression plant, start to pass into air, the speed of air is 5L/min, 3h is reacted under the condition of 50 DEG C, react complete, after filtration, washing catalyst is reused in reaction next time and goes, remaining reaction solution removes unnecessary solvent through decompression, and yield is 88.5%.Object product is obtained again through rectifying.
Although above-described embodiment is described the specific embodiment of the present invention; but the restriction not to invention protection domain; one of ordinary skill in the art should be understood that; on the basis of the technical scheme of invention, those skilled in the art do not need to pay various amendment or distortion that creative work can make still in protection scope of the present invention.
Claims (10)
1. the synthetic method of a solid-supported catalyst; it is characterized in that; salicylaldehyde derivatives and diamine compounds are reacted and generates schiff base ligand; prepare Metal Schiff _ base title complex with transition metal salt solution coordination again, then on the polystyrene microsphere carrier containing acyl group, be prepared into solid-supported catalyst by immobilized for Metal Schiff _ base title complex by F-C acylation reaction.
2. the synthetic method of a kind of solid-supported catalyst as claimed in claim 1, it is characterized in that, step is as follows:
(1) salicylaldehyde derivatives and diamine compounds are reacted generate schiff base ligand, then prepare Metal Schiff _ base title complex with transition metal salt solution coordination;
(2) the Metal Schiff _ base title complex of preparation is dissolved in a solvent, add chlorine acyl group polystyrene microsphere, after reacting by heating, obtain solid-supported catalyst.
3. the synthetic method of a kind of solid-supported catalyst as claimed in claim 2, it is characterized in that, the concrete steps of described step (1) are: joined by salicylaldehyde derivatives in the reaction vessel containing solvent 1, by heating in water bath, salicylaldehyde derivatives is dissolved, under the condition stirred, maintain solution temperature is 50-90 DEG C, dropwise drip diamine compounds, after dropwising back flow reaction 1.5-2.5h, prepare schiff base ligand through filtering and washing drying; Again be dissolved in by schiff base ligand in the reaction vessel containing solvent 2, start to drip transition metal salt solution, suction filtration crystallization after back flow reaction 2-3h, vacuum-drying obtains Metal Schiff _ base title complex.
4. the synthetic method of a kind of solid-supported catalyst as claimed in claim 3, is characterized in that, the substituting group of described salicylaldehyde derivatives is methyl, the tertiary butyl, methoxyl group, preferred tertiary butyl; Described diamine compounds is quadrol, cyclohexanediamine or phenylenediamine, preferred phenylenediamine; Described transition metal salt is mantoquita, zinc salt, nickel salt or cobalt salt.
5. the synthetic method of a kind of solid-supported catalyst as claimed in claim 3, is characterized in that, the mol ratio of described salicylaldehyde derivatives and diamine derivative is: 2.0-2.5:1, preferred molar ratio 2.2:1; The mol ratio of described transition metal and diamine compounds is 1.1-1.3:1.
6. the synthetic method of a kind of solid-supported catalyst as claimed in claim 2, is characterized in that, the addition of described chlorine acyl group polystyrene microsphere is react used 2-2.5 times.
7. one kind utilize as arbitrary in claim 1-6 as described in the solid-supported catalyst prepared of method.
8. the application of solid-supported catalyst as claimed in claim 7 in synthesis dimethyl diketone.
9. a synthetic method for dimethyl diketone, is characterized in that, is that raw material adds solid-supported catalyst as claimed in claim 7, passes into air catalytic oxidation and obtain dimethyl diketone with acetoin.
10. the synthetic method of a kind of dimethyl diketone as claimed in claim 9, is characterized in that, it is 2-5L/min that described air passes into speed.
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| CN108722485A (en) * | 2017-04-21 | 2018-11-02 | 中国石油化工股份有限公司 | A kind of complex catalyst of Phenol by Hydrogen Peroxide hydroxylating synthesizing benzene diphenol |
| CN110156139A (en) * | 2019-06-13 | 2019-08-23 | 河南师范大学 | Cu (II)-schiff bases complex catalyzing hydrogen peroxide oxidative degradation Phenol for Waste Water pollutant method |
| CN114054092A (en) * | 2021-11-29 | 2022-02-18 | 万华化学集团股份有限公司 | Catalyst for preparing beta-carotene and preparation method and application thereof |
| CN116375566A (en) * | 2023-04-04 | 2023-07-04 | 济南悟通生物科技有限公司 | Catalytic synthesis method of 2, 3-butanedione, catalyst and preparation method |
| CN117924056A (en) * | 2024-03-25 | 2024-04-26 | 山东新和成药业有限公司 | Synthesis method of conjugated diketone compound |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108722485A (en) * | 2017-04-21 | 2018-11-02 | 中国石油化工股份有限公司 | A kind of complex catalyst of Phenol by Hydrogen Peroxide hydroxylating synthesizing benzene diphenol |
| CN108722485B (en) * | 2017-04-21 | 2021-07-23 | 中国石油化工股份有限公司 | Complex catalyst for synthesizing benzenediol by hydroxylation of phenol and hydrogen peroxide |
| CN110156139A (en) * | 2019-06-13 | 2019-08-23 | 河南师范大学 | Cu (II)-schiff bases complex catalyzing hydrogen peroxide oxidative degradation Phenol for Waste Water pollutant method |
| CN114054092A (en) * | 2021-11-29 | 2022-02-18 | 万华化学集团股份有限公司 | Catalyst for preparing beta-carotene and preparation method and application thereof |
| CN114054092B (en) * | 2021-11-29 | 2023-10-13 | 万华化学集团股份有限公司 | Catalyst for preparing beta-carotene and preparation method and application thereof |
| CN116375566A (en) * | 2023-04-04 | 2023-07-04 | 济南悟通生物科技有限公司 | Catalytic synthesis method of 2, 3-butanedione, catalyst and preparation method |
| CN116375566B (en) * | 2023-04-04 | 2023-08-29 | 济南悟通生物科技有限公司 | Catalytic synthesis method of 2, 3-butanedione, catalyst and preparation method |
| CN117924056A (en) * | 2024-03-25 | 2024-04-26 | 山东新和成药业有限公司 | Synthesis method of conjugated diketone compound |
| CN117924056B (en) * | 2024-03-25 | 2024-06-11 | 山东新和成药业有限公司 | Synthesis method of conjugated diketone compound |
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