CN108855038A - A kind of method for preparing catalyst of carbonate synthesis glyceride - Google Patents
A kind of method for preparing catalyst of carbonate synthesis glyceride Download PDFInfo
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- CN108855038A CN108855038A CN201810521681.4A CN201810521681A CN108855038A CN 108855038 A CN108855038 A CN 108855038A CN 201810521681 A CN201810521681 A CN 201810521681A CN 108855038 A CN108855038 A CN 108855038A
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The present invention provides a kind of method for preparing catalyst of carbonate synthesis glyceride, using metal barium salt and cerium salt as raw material, alkali and alkali carbonate as precipitating reagent, under the conditions of existing for the template, by co-precipitation, high-temperature roasting, removing template is removed, obtains the cellular catalyst of high activity.The catalyst is used for using carbon dioxide, epoxyalkane and glycerol as in the reaction of raw material one pot process carbonic acid glyceride, and process is environmentally protective, target product carbonic acid glyceride high income.
Description
Technical field
The invention belongs to catalytic fields, are related to a kind of method for preparing catalyst of carbonate synthesis glyceride.
Background technique
With the rise of emerging energy, biodiesel industry is rapidly developed in recent years, but also along with production
A large amount of by-product glycerin is given birth to.The a large amount of surplus of glycerol has seriously affected its market price, and processing cost gradually increases, this
Greatly hinder the sound development of biodiesel industry.Therefore it needs to find new outlet for superfluous glycerol, convert glycerol into
It is a selection well for high added value derivative.
Converting glycerol into high value added product can prevent it from largely overstocking, and improve its economic value, have huge
Economic benefit, while the economy of biodiesel industry can also be improved, cost is reduced, its sustainable development is promoted.In addition sweet
Oil is a kind of ideal renewable resource, and green is sustainable, meets National Sustainable Development Strategies, therefore glycerol downstream product
Exploitation is of great significance to China's industrial expansion.
Currently, the research more as the glycerol derivatives of Material synthesis high added value aspect using glycerol, such as glycerol exist
Methacrylaldehyde is prepared under acid catalysis；Hydrogenolysis prepares 1,2-PD and 1,3-PD；Oxidation prepares glyceric acid etc..Carbonic acid glyceride
It is one of the glycerol derivatives of most attraction, it has the characteristics that many, such as low toxicity, higher boiling, biodegradable, difunctional
Deng.Based on these features, carbonic acid glyceride tool has been widely used：For example, it is molten to can be used as pigment, paint, the solvent of cosmetics
Agent is used as carrier solvent in pharmaceutical synthesis, for fuel as additive；Component as gas phase seperation film；It can be used as gathering
The novel components of urethane foam, surfactant also can be used as the component of detergent coating；In addition, it is also polycarbonate, gathers
Ester, polyureas, etc. polymer important intermediate.
Due to the extensive purposes of carbonic acid glyceride, its synthesis also becomes the research emphasis of researcher.Carbonic acid is sweet
There are mainly five types of the synthetic methods of grease, and the ester exchange reaction of (1) glycerol and dialkyl carbonate or cyclic carbonate prepares carbon
The method of acid glyceride；(2) alcoholysis reaction of the glycerol with urea；(3) oxidative carbonylation of glycerol and carbon monoxide and oxygen is anti-
It answers；(4) and the same CO of glycerol2Carbonylation；(5) glycerol and phosgene reaction the preparation method etc..Studying at present more has glycerol
With the ester exchange reaction of carbonic ester, the alcoholysis reaction of glycerol and urea.The patent applied such as Evonik rome Co., Ltd
CN101287720A, in report using dialkyl carbonate or cyclic carbonate and glycerol as raw material, exist in basic catalyst
The lower method for carrying out ester exchange reaction and preparing carbonic acid glyceride.The applied patent of Chinese Academy of Sciences's Lanzhou Chemical Physics research
In CN102250051A, it was recently reported that using cyclic carbonate and glycerol as raw material, using alkali ionic liquid as catalyst preparation carbonic acid
The method of glyceride.Chinese Academy of Sciences's Shanxi coalification patent CN103007915A in, it was recently reported that Mg-Al hydrotalcite load alkali gold
Belong to method of the oxide as catalyst dimethyl carbonate and glyceride exchange system for carbonic acid glyceride.South Korea's production technology
In the patent CN103357394A of research institute's report, it was recently reported that zinc-aluminium metal oxide is as catalyst glycerol and urea
Alcoholysis reaction.Oxidation of Carbon Monoxide carbonylation method and phosgenation reaction raw materials are more toxic, and have biggish security risk.Dioxy
It is economic and environment-friendly that change carbon and glycerol directly reaction prepare carbonic acid glyceride, and atom utilization efficiency is high, but severe reaction conditions, and
Yield is lower.
Summary of the invention
Technical problem：During preparing carbonic acid glyceride as raw material using glycerol and carbon dioxide for solution is existing, catalysis
Agent can not be catalyzed simultaneously carbon dioxide and epoxyalkane cycloaddition reaction and subsequent cyclic carbonate ester and glycerol transesterification it is anti-
It answers, reaction needs the technical issues of carrying out step by step, and the present invention provides a kind of method for preparing catalyst of carbonate synthesis glyceride.
The catalyst can catalyzing glycerol, epoxyalkane and carbon dioxide one pot process carbonic acid glyceride, and have it is higher activity and
Good stabilization.
Technical solution：The method for preparing catalyst of carbonate synthesis glyceride of the invention, steps are as follows：
(1) be 1 according to molar ratio by metal barium salt and metal cerium salt: (0.2~5) is dissolved in deionized water respectively, respectively
Obtain the barium salt aqueous solution and cerium salt solution that concentration of metal ions is 0.01~1mol/L；By alkali and alkali carbonate with 1:
The molar ratio of (0.1~10) is dissolved in deionized water, and the concentration for being prepared into the sum of hydroxyl and carbonate is 0.01~1mol/L
Alkaline solution；
(2) template is added in the alkaline solution, template dosage is with metal barium salt and metal cerium salt substance
On the basis of the sum of amount, it is every mM of metal salt of 0.01~0.5g template, is stirred well to whole dissolutions；By barium salt aqueous solution
It is added dropwise in the alkaline solution containing template with the speed of 0.5~10mL/min with cerium salt solution；
(3) continue in 10~60 DEG C stirring after being added dropwise to complete for 24 hours, gained sediment centrifuge separation, during deionized water is washed till
Property, obtained solid in 80 DEG C of drying 12h, then with the heating rate of 1~20 DEG C/min in 200~900 DEG C roast 5 hours, institute
Obtaining solid is catalyst.
Further, in the method for the present invention, the metal barium salt of step (1) is one of barium nitrate, barium chloride, the gold
Category cerium salt is one of cerous nitrate, cerium chloride, cerous sulfate, ammonium ceric nitrate.
Further, in the method for the present invention, the alkali of step (1) is ammonium hydroxide, in lithium hydroxide, sodium hydroxide, potassium hydroxide
One kind, alkali carbonate be one of sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate.
Further, in the method for the present invention, the template of step (2) is polyvinylpyrrolidone, polyethylene glycol, polyethylene
Alcohol, polystyrene, polyethylene oxide-polypropylene oxide-polyethylene oxide triblock copolymer P123, polyoxyethylene polyoxypropylene
One of ether block copolymers F127.
Further, in the method for the present invention, the relationship of each solutes content is shown below in the solution of step (2)：
Wherein n (Ce3+) it is Ce3+The amount of the substance of ion, n (Ba2+) it is Ba2+The amount of the substance of ion, n (OH-) are OH-
The amount of the substance of ion, n (CO3 2-) it is CO3 2-The amount of the substance of ion.
The catalyst of the method for the present invention synthesis is used for using carbon dioxide, epoxyalkane and glycerol as raw material one pot process carbon
In the reaction of acid glyceride.Wherein epoxyalkane include ethylene oxide, propylene oxide, epoxy butane, allyl glycidyl ether,
Glycidol, styrene oxide, oxidizing ethyle alkyl, epoxychloropropane etc..
The method that catalyst of the invention prepares carbonic acid glyceride is reacted with glycerol, epoxyalkane and carbon dioxide
For raw material, one kettle way prepares carbonic acid glyceride in the presence of freshly prepd catalyst.During the reaction, epoxyalkane first and
Carbon dioxide carries out cycloaddition reaction and forms cyclic carbonate ester, and glycerol is remarkably improved reaction speed as co-catalyst in this process
The yield of rate and cyclic carbonate ester；Then cyclic carbonate ester and glycerol carry out ester exchange reaction and prepare fluid under the action of catalyst
Ester.Reaction directly prepares high added value glycerol derivatives, economic ring by raw material of two kinds of industrial by-products of glycerol and carbon dioxide
It protects；Intermediate cyclic carbonate ester does not need to be separated, and shortens process flow, reduces production cost；In addition, raw materials glycerine itself can be made
The efficiency of reaction is significantly improved for co-catalyst.
The present invention prepares catalyst by coprecipitation, increases the cellular structure of catalyst using template as pore creating material
And specific surface area, so that the more active sites of catalyst are able to haptoreaction substrate, to improve reaction efficiency.The catalyst
The cycloaddition reaction of carbon dioxide and epoxyalkane and the ester exchange reaction of carbonic ester and glycerol can be used to be catalyzed simultaneously.Reaction
Using carbon dioxide, epoxyalkane, glycerol as raw material, one pot process carbonic acid glyceride under the action of catalyst.
Beneficial effect：Compared with prior art, the present invention having the following advantages that：
The metal cerium salt and barium salt that the present invention uses specific proportion is raw materials, using alkali and alkali carbonate as precipitating
Agent prepares catalyst by coprecipitation, prepared catalyst can efficient catalytic epoxyalkane, two in the presence of template
Carbonoxide and one-step glycerol carbonate synthesis glyceride.The method of existing carbonate synthesis glyceride generallys use method of fractional steps progress：It is first
First, epoxyalkane and carbon dioxide cycloaddition synthesizing cyclic carbonate ester；Then, cyclic carbonate ester and methanol carry out transesterification carbonate synthesis
Dimethyl ester；Finally, dimethyl carbonate and glycerol carry out transesterification carbonate synthesis glyceride.Each step requires point in reaction process
From purification, production cost is higher.Using catalyst prepared by the present invention, can be closed by epoxyalkane, carbon dioxide and one-step glycerol
At carbonic acid glyceride, intermediate does not need to be separated purification, enormously simplifies the process of production.Meanwhile urging using this method preparation
Agent catalytic activity with higher and stability.While the conversion ratio of epoxyalkane reaches 99.8%, the conversion ratio of glycerol
Reachable 99.2%, in addition, the yield of product carbonic acid glyceride reachable 98.9%.
Specific embodiment
Below by embodiment, the present invention is further elaborated, it should be noted that following instance is merely to illustrate this hair
It is bright rather than limit the scope of the invention.
Metal ion molar ratio is 1 by the present invention: the metal barium salt and metallic cerium salt of (0.2~5) are dissolved in deionization respectively
In water, the aqueous solution that concentration is 0.01~1mol/L is obtained；Alkali and alkali carbonate are with 1: the ratio of (0.1~10) is dissolved in
In ionized water, it is prepared into the alkaline solution that concentration is 0.01~1mol/L；Template is added in alkaline solution, template is used
Amount is every mM of metal salt of 0.01~0.5g template, is stirred well to whole dissolutions；By barium salt and the aqueous solution of cerium salt with
The speed of 0.5~10mL/min is added dropwise in the alkaline aqueous solution containing template.Continue to stir in 10~60 DEG C after being added dropwise to complete
12h.Separation, deionized water are washed till neutrality.Obtained solid in 80 DEG C of drying 12h, then with the heating rate of 1~20 DEG C/min in
200~900 DEG C roast 5 hours, and obtained solid is catalyst.
Salt as described above is one of barium nitrate, barium chloride, cerous nitrate, cerium chloride, cerous sulfate, ammonium ceric nitrate,
Concentration is 0.01~1mol/L, and the molar ratio of barium salt and cerium salt is 1: (0.2~5).
Alkali as described above is one of ammonium hydroxide, lithium hydroxide, sodium hydroxide, potassium hydroxide aqueous solution, alkali metal carbon
Hydrochlorate is one of sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate.The molar ratio of alkali and alkali carbonate is 1: (0.1~
10), concentration is 0.01~1mol/L.
The relationship of metal salt and alkali and alkali carbonate is as described above：The mole of metal ion is the same as its valence state
The sum of product and hydroxyl mole add carbonate mole with the product of its valence state and ratio be 1: (1~2).
Template as described above is polyvinylpyrrolidone, polyethylene glycol, polyvinyl alcohol, polystyrene, P123, F127
One of, the effect of template is to prepare cellular catalyst.
Embodiment 1：Prepare the catalyst of carbonate synthesis glyceride：
Six nitric hydrate ceriums (1mmol) and barium nitrate (1mmol) are dissolved in respectively in 20mL deionized water, barium nitrate is made
The molar ratio of the aqueous solution of (0.05mol/L) and cerous nitrate (0.05mol/L), barium nitrate and cerous nitrate is 1: 1；Sodium hydroxide and
Sodium carbonate is dissolved in deionized water with 3: 1 molar ratio, is prepared into the alkaline solution of 40mL (0.1mol/L), mole of metal salt
Amount and the sum of its valence state product and the mole of alkali and alkali carbonate and the product of its valence state and ratio be 1: 1；By mould
Plate agent PVP is added in alkaline solution with every mM of metal salt of 0.25g template and is stirred well to whole dissolutions；By barium nitrate
It is added dropwise in the alkaline aqueous solution containing template simultaneously with the aqueous solution of cerous nitrate with the speed of 1mL/min.After being added dropwise to complete in
60 DEG C are continued stirring 24 hours.Centrifuge separation, deionized water are washed till neutrality.Gained catalyst precursor is small in 80 DEG C of drying 12
When, 500 DEG C then, which are risen to, with 10 DEG C/min roasts 5 hours.
Embodiment 2：
Preparation step and method are same as Example 1, and the molar ratio of barium nitrate and cerous nitrate in embodiment 1 is adjusted to 1:
0.2。
Embodiment 3：
Preparation step and method are same as Example 1, and the molar ratio of barium nitrate and cerous nitrate in embodiment 1 is adjusted to 1: 5.
Embodiment 4：
Preparation step and method are same as Example 1, by barium nitrate in embodiment 1 and cerous nitrate cerium chloride and barium chloride
Instead of.
Embodiment 5：
Preparation step and method are same as Example 4, by cerium chloride in embodiment 4 and barium chloride cerous sulfate and barium chloride
Instead of.
Embodiment 6：
Preparation step and method are same as Example 4, by cerium chloride in embodiment 4 and barium chloride ammonium ceric nitrate and nitric acid
Barium replaces.
Embodiment 7：
Preparation step and method are same as Example 4, and the molar ratio of 4 sodium hydroxide of embodiment and sodium carbonate is adjusted to 1:
0.1。
Embodiment 8：
Preparation step and method are same as Example 4, and the molar ratio of 4 sodium hydroxide of embodiment and sodium carbonate is adjusted to 1:
10。
Embodiment 9：
Preparation step and method are same as Example 1, by the mole of metal salt in embodiment 1 and its valence state product and
With the mole of alkali and alkali carbonate and its valence state product and ratio be adjusted to 1.5: 1.
Embodiment 10：
Preparation step and method are same as Example 1, by the mole of metal salt in embodiment 1 and its valence state product and
With the mole of alkali and alkali carbonate and its valence state product and ratio be adjusted to 1: 2.
Embodiment 11：
Preparation step and method are same as Example 9, sodium hydroxide in embodiment 9 are replaced with potassium hydroxide, sodium carbonate
It is replaced with cesium carbonate.
Embodiment 12：
Preparation step and method are identical as embodiment 11, and potassium hydroxide in embodiment 11 is replaced with ammonium hydroxide, and cesium carbonate is used
Potassium carbonate replaces.
Embodiment 13：
Preparation step and method are identical as embodiment 11, potassium hydroxide in embodiment 11 are replaced with lithium hydroxide, carbonic acid
Caesium is replaced with rubidium carbonate.
Embodiment 14：
Preparation step and method are identical as embodiment 11, and template PVP in embodiment 11 is replaced with P123.
Embodiment 15：
Preparation step and method are identical as embodiment 11, and template PVP in embodiment 11 is replaced with F127.
Embodiment 16：
Preparation step and method are identical as embodiment 11, and the dosage of template in embodiment 11 is adjusted to 0.01g template
Every mM of metal salt.
Embodiment 17：
Preparation step and method are identical as embodiment 11, and it is every that the dosage of template in embodiment 11 is adjusted to 0.5g template
MM metal salt.
Embodiment 18：
Preparation step and method are same as Example 9, and the reaction temperature after alkali is added dropwise to complete in embodiment 9 is adjusted to 10
Degree.
Embodiment 19：
Preparation step and method are same as Example 9, and the reaction temperature after alkali is added dropwise to complete in embodiment 9 is adjusted to 30
Degree.
Embodiment 20：
Preparation step and method are same as Example 9, by the heating rate in embodiment 9 in roasting process be adjusted to 1 DEG C/
min。
Embodiment 21：
Preparation step and method are same as Example 9, by the heating rate in embodiment 9 in roasting process be adjusted to 20 DEG C/
min。
Embodiment 22：
Preparation step and method are same as Example 8, and the maturing temperature of catalyst in embodiment 8 is adjusted to 200 DEG C.
Embodiment 23：
Preparation step and method are same as Example 8, and the maturing temperature of catalyst in embodiment 8 is adjusted to 900 DEG C.
Embodiment 24：
The catalyst recycled in embodiment 10 is roasted 5 hours in 600 DEG C after ethanol washing 3 times, is used for this secondary response.
Embodiment 25：Catalytic performance test.
It is carried out with catalyst of the reaction of glycerol, carbon dioxide and propylene oxide carbonate synthesis glyceride to embodiment 1-8
Evaluation.Reaction condition is as follows：Glycerol 4.62g (50mmol) and propylene oxide 5.83g (100mmol) are added to 100mL reaction
In kettle, it is filled with carbon dioxide 2.0MPa, is warming up to 120 DEG C, reacts 6h.It is cooling, catalyst centrifuge separation, ethanol washing, in 600
DEG C roasting 2h, be subsequently used for lower secondary response.
The catalytic effect of catalyst performance prepared by 1 embodiment 1-11 of table
From 1 data of table it is found that on the catalyst prepared in embodiment 1-8, epoxyalkane and glycerol are all with higher
Conversion ratio, product carbonic acid glyceride have higher yield.In addition, catalyst has good stability, during reuse
Effect is without being decreased obviously.
Claims (5)
1. a kind of method for preparing catalyst of carbonate synthesis glyceride, which is characterized in that this approach includes the following steps：
(1) be 1 according to molar ratio by metal barium salt and metal cerium salt: (0.2~5) is dissolved in deionized water respectively, is respectively obtained
Concentration of metal ions is the barium salt aqueous solution and cerium salt solution of 0.01~1mol/L；By alkali and alkali carbonate with 1: (0.1
~10) molar ratio is dissolved in deionized water, and the concentration for being prepared into the sum of hydroxyl and carbonate is the alkali of 0.01~1mol/L
Property solution；
(2) template is added in the alkaline solution, template dosage with the amount of metal barium salt and metal cerium salt substance it
With on the basis of, it is every mM of metal salt of 0.01~0.5g template, is stirred well to whole dissolutions；By barium salt aqueous solution and cerium
Saline solution is added dropwise in the alkaline solution containing template with the speed of 0.5~10mL/min；
(3) continue stirring for 24 hours in 10~60 DEG C after being added dropwise to complete, gained sediment centrifuge separation, deionized water is washed till neutrality, institute
Solid is obtained in 80 DEG C of drying 12h, is then roasted 5 hours with the heating rate of 1~20 DEG C/min in 200~900 DEG C, obtained solid
As catalyst.
2. the method for preparing catalyst of carbonate synthesis glyceride described in accordance with the claim 1, which is characterized in that the step
(1) metal barium salt is one of barium nitrate, barium chloride, and the metal cerium salt is cerous nitrate, cerium chloride, cerous sulfate, nitric acid
One of cerium ammonium.
3. the method for preparing catalyst of carbonate synthesis glyceride described in accordance with the claim 1, which is characterized in that the step
(1) alkali be one of ammonium hydroxide, lithium hydroxide, sodium hydroxide, potassium hydroxide, alkali carbonate be sodium carbonate, potassium carbonate,
One of rubidium carbonate, cesium carbonate.
4. according to the method for preparing catalyst of carbonate synthesis glyceride described in claim 1,2 or 3, which is characterized in that described
The template of step (2) is polyvinylpyrrolidone, polyethylene glycol, polyvinyl alcohol, polystyrene, polyethylene oxide-polycyclic oxygen
One of propane-polyethylene oxide triblock copolymer P123, polyoxyethylene poly-oxygen propylene aether block copolymer F127.
5. according to the method for preparing catalyst of carbonate synthesis glyceride described in claim 1,2 or 3, which is characterized in that described
The relationship of each solutes content is shown below in the solution of step (2)：
Wherein n (Ce3+) it is Ce3+The amount of the substance of ion, n (Ba2+) it is Ba2+The amount of the substance of ion, n (OH-) it is OH-ion
Substance amount, n (CO3 2-) it is CO3 2-The amount of the substance of ion.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115594657A (en) * | 2022-12-07 | 2023-01-13 | 中国科学院过程工程研究所（Cn） | Cyclic carbonate and preparation method and application thereof |
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| CN103357394B (en) * | 2012-04-10 | 2016-01-06 | 韩国生产技术研究院 | For being manufactured the catalyst of carbonic acid glyceride, its manufacture method by glycerine and utilizing this method being manufactured carbonic acid glyceride by glycerine |
| CN103007915A (en) * | 2012-12-07 | 2013-04-03 | 中国科学院山西煤炭化学研究所 | Solid base catalyst for synthesis of glycerol carbonate and its preparation method and application |
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| CN115594657A (en) * | 2022-12-07 | 2023-01-13 | 中国科学院过程工程研究所（Cn） | Cyclic carbonate and preparation method and application thereof |
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