CN107805239A - A kind of method that chromium-based catalysts chemical recycling of carbon dioxide prepares cyclic carbonate - Google Patents
A kind of method that chromium-based catalysts chemical recycling of carbon dioxide prepares cyclic carbonate Download PDFInfo
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- CN107805239A CN107805239A CN201711274994.6A CN201711274994A CN107805239A CN 107805239 A CN107805239 A CN 107805239A CN 201711274994 A CN201711274994 A CN 201711274994A CN 107805239 A CN107805239 A CN 107805239A
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- C07—ORGANIC CHEMISTRY
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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
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
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- 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
- C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
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- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/025—Ligands with a porphyrin ring system or analogues thereof, e.g. phthalocyanines, corroles
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/62—Chromium
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Abstract
The invention discloses a kind of method that chromium-based catalysts chemical recycling of carbon dioxide prepares cyclic carbonate, raw material is used as by the use of carbon dioxide and epoxides, to be conjugated chromium porphyrin capillary copolymer material as heterogeneous catalyst, tetra-n-butyl ammonium bromide is co-catalyst, in the case where normal temperature and pressure is solvent-free, efficient green catalytically synthesizing cyclic carbonate ester is realized.The major advantage of this method is that method for preparing catalyst is simple, and cost is low, and catalytic activity is high, and structural behaviour is stable, easily recovery, repeats and utilizes;Reaction condition is gentle, speed is fast and safe operation, suitable for large-scale industrial production.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of chromium-based catalysts chemical recycling of carbon dioxide prepares ring-type
The method of carbonic ester.
Background technology
With the progress of the development human civilization of society, especially industrial great development with rapid changepl. never-ending changes and improvements, for fossil energy
The consumption requirements in source increasingly increase.With a large amount of uses of fossil fuel, the concentration of carbon dioxide quickly raises, and turns into a kind of master
Greenhouse gases are wanted, cause a series of environment and ecological problem.Meanwhile carbon dioxide is used as a kind of widely distributed, rich reserves, honest and clean
Valency is easy to get, is renewable, be nontoxic, the non-flammable preferable resource of carbon one.No matter from the angle that environmental protection or renewable resource utilize
Degree considers that the research in terms of the capture and chemical conversion of carbon dioxide is all significant.Using carbon dioxide as Material synthesis
Organic carbonate is exactly an exemplary of its recycling, has been realized in industrialized production at present.
Organic carbonate is a kind of green chemical with characteristics such as higher boiling, low-steam pressure, low toxicities, has been widely used in
The multiple fields such as solvent, detergent, lithium battery electrolytes, fuel additive.Organic carbonate can be divided into linear carbonate
And cyclic carbonate.Wherein cyclic carbonate is widely used as the electrolyte of lithium battery, with the fast development of new energy, market pair
It is increasing in the demand of high-quality cyclic carbonate.
From the perspective of Green Chemistry and sustainable development, using carbon dioxide and epoxides as Material synthesis carbonic ester
Provide a kind of safe and clean, sustainable, high atom economy new way.Current industrialized carbon dioxide and ring
The process that oxygen prepares cyclic carbonate mainly has two kinds of catalyst system and catalyzings:Polyethylene glycol/KI system and quaternary ammonium salt system.The former
Iodine can be generated during the course of the reaction, causes finished product to turn to be yellow, and product quality declines;And the pressure that the latter needs during the course of the reaction
Power is higher, and to the security of production operation, the requirement for performance that equipment is pressure-resistant is higher, and equipment cost is high.
At present, with CO2It is raw material with cyclic carbonate, in the reaction system of synthesizing annular carbonate, has developed
A series of catalyst, as quaternary ammonium salt, quaternary alkylphosphonium salts, organic base, ionic liquid, metal oxide, metal complex, feature are organic
Polymeric material and metalloporphyrin etc..2013, Deng et al. research group was using salen Al/Co and three ethynylbenzenes to be single
Body, by Sonogashira coupling reactions, microporous polymer catalyst Al-CMP and Co-CMP are prepared for, in the reaction system
In achieve preferable catalytic effect, and the just desirable good yield under normal temperature and pressure conditionses, while catalyst may be used also
Recycling [Nat.Commun., 2013,4,1-7].2016, Xiao Fengshou taught seminar with tetravinyl Cob altporphyrin
For monomer, by the method for radical polymerization, catalyst Co/POP-TPP is made, at 29 DEG C, when pressure is 0.1MPa, reaction
24h, achieves satisfied result, catalyst can circulation and stress use, and by low concentration CO2As research object, have
Certain industrial application value [J.Catal., 2016,338,202].
The content of the invention
The technical problems to be solved by the invention are deposited inefficient in a mild condition for the current reaction system
Problem, there is provided a kind of synthesis step is simple, raw material is cheap and easy to get, high catalytic efficiency, the stable heterogeneous catalyst easily reclaimed, normal
Under normal temperature and pressure, condition of no solvent, efficient catalytic is converted into cyclic carbonate, can be widely applied to field of industrial production.
In order to solve the above technical problems, the present invention uses following technical scheme:
A kind of method that chromium-based catalysts chemical recycling of carbon dioxide prepares cyclic carbonate, original is used as using carbon dioxide and epoxides
Material, to be conjugated chromium porphyrin capillary copolymer material as heterogeneous catalyst, tetra-n-butyl ammonium bromide is co-catalyst, in normal temperature and pressure
Under solvent-free, 12-48h to be reacted, has synthesized cyclic carbonate in high yield, heterogeneous catalyst separation is simple, washable recovery, and
It can realize and repeatedly use.
The conjugation chromium porphyrin capillary copolymer material uses Scholl coupling reactions, using chromium tetraphenylporphyrin to be single
Body, use anhydrous AlCl3Catalyst preparation obtains, and its structural formula is as follows:
。
The epoxide is expoxy propane, epoxy butane, epoxychloropropane, epoxy bromopropane, styrene oxide, benzene
Base glycidol ether or cyclohexene oxide.
The dosage of the active component of the heterogeneous catalyst is 0.2~0.5mol% of epoxide dosage.
The dosage of the co-catalyst is 3.6~7.2mol% of epoxide.
The conjugation chromium porphyrin capillary copolymer material can be replaced with conjugation chromium porphyrin bibenzyl amine capillary copolymer material,
The conjugation chromium porphyrin bibenzyl amine capillary copolymer material uses Scholl coupling reactions, using chromium tetraphenylporphyrin and benzylamine as
Monomer, use anhydrous AlCl3Catalyst preparation obtains, and its structural formula is as follows:
。
Beneficial effects of the present invention:1) present invention utilizes and is conjugated chromium porphyrin/conjugation vanadium porphyrin bibenzyl amine microporous polymer material
Material and tetra-n-butyl ammonium bromide are realized under normal temperature and pressure conditionses, efficient catalytic CO as bicomponent catalyst2And epoxides
Synthesizing annular carbonate, mass energy is saved, reduce the requirement to press device in production, substantially increase the peace of operation
Quan Xing;2) catalyst amount is low, high catalytic efficiency, reaction time are short, product is easily isolated purifying, is easy to actual industrial to operate;
3) any organic solvent need not be added, it is green;4) catalyst raw material used in is easy to get, cost is low, the quick letter of synthesis
It is single.Heterogeneous catalyst separation is simple, washable recovery, and can realize and repeatedly use(More than 20 times).
Specific implementation method
The present invention is further described in the examples below, but the merely illustrative purposes of discussion of these embodiments, should not be solved
It is interpreted as the implementation limitation of the present invention.
Embodiment 1
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.4mol%)Catalyst conjugation chromium
Porphyrin capillary copolymer material, 12.5mmol expoxy propane and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, are passed through titanium dioxide
Carbon and to keep pressure be 0.1MPa, under the conditions of temperature is 25 DEG C, after stirring 48h, room temperature cooling, slowly discharges remaining dioxy
After changing carbon, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 87%.
Embodiment 2
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.3mol%)Catalyst conjugation chromium
Porphyrin capillary copolymer material, 12.5mmol epoxy butanes and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, are passed through titanium dioxide
Carbon and to keep pressure be 0.1MPa, under the conditions of temperature is 25 DEG C, after stirring 48h, room temperature cooling, slowly discharges remaining dioxy
After changing carbon, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 86%.
Embodiment 3
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.5mol%)Catalyst conjugation chromium
Porphyrin capillary copolymer material, 12.5mmol epoxychloropropane and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, are passed through dioxy
It is 0.1MPa to change carbon and keep pressure, under the conditions of temperature is 25 DEG C, after stirring 48h, room temperature cooling, slowly discharges remaining two
After carbonoxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 88%.
Embodiment 4
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.45mol%)Catalyst conjugation chromium
Porphyrin capillary copolymer material, 12.5mmol epoxy bromopropanes and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, are passed through dioxy
It is 0.1MPa to change carbon and keep pressure, under the conditions of temperature is 25 DEG C, after stirring 36h, room temperature cooling, slowly discharges remaining two
After carbonoxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 87%.
Embodiment 5
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.2mol%)Catalyst conjugation chromium
Porphyrin capillary copolymer material, 12.5mmol styrene oxides and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, are passed through dioxy
It is 0.1MPa to change carbon and keep pressure, under the conditions of temperature is 25 DEG C, after stirring 48h, room temperature cooling, slowly discharges remaining two
After carbonoxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 80%.
Embodiment 6
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.2mol%)Catalyst conjugation chromium
Porphyrin capillary copolymer material, 12.5mmol phenyl glycidyl ethers and 0.675mmol co-catalyst tetra-n-butyl ammonium bromides, lead to
It is 0.1MPa to enter carbon dioxide and keep pressure, and under the conditions of temperature is 25 DEG C, after stirring 24h, room temperature cooling, slowly release is surplus
After remaining carbon dioxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 78%.
Embodiment 7
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.3mol%)Catalyst conjugation chromium
Porphyrin capillary copolymer material, 12.5mmol cyclohexene oxides and 0.45mmol co-catalyst tetra-n-butyl ammonium bromides, are passed through two
Carbonoxide and to keep pressure be 0.1MPa, under the conditions of temperature is 25 DEG C, after stirring 12h, room temperature cooling, slowly discharges remaining
After carbon dioxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 80%.
Embodiment 8
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.4mol%)Catalyst conjugation chromium
Porphyrin bibenzyl amine capillary copolymer material, 12.5mmol expoxy propane and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, are passed through
Carbon dioxide and to keep pressure be 0.1MPa, under the conditions of temperature is 25 DEG C, after stirring 48h, room temperature cooling, slowly release is remaining
Carbon dioxide after, filter to isolate catalyst, after purification cyclic carbonate separation yield be 80%.
Embodiment 9
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.3mol%)Catalyst conjugation chromium
Porphyrin bibenzyl amine capillary copolymer material, 12.5mmol epoxy butanes and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, are passed through
Carbon dioxide and to keep pressure be 0.1MPa, under the conditions of temperature is 25 DEG C, after stirring 48h, room temperature cooling, slowly release is remaining
Carbon dioxide after, filter to isolate catalyst, after purification cyclic carbonate separation yield be 76%.
Embodiment 10
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.5mol%)Catalyst conjugation chromium
Porphyrin bibenzyl amine capillary copolymer material, 12.5mmol epoxychloropropane and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, lead to
It is 0.1MPa to enter carbon dioxide and keep pressure, and under the conditions of temperature is 25 DEG C, after stirring 48h, room temperature cooling, slowly release is surplus
After remaining carbon dioxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 82%.
Embodiment 11
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.45mol%)Catalyst conjugation chromium
Porphyrin bibenzyl amine capillary copolymer material, 12.5mmol epoxy bromopropanes and 0.675mmol co-catalyst tetra-n-butyl ammonium bromides,
It is 0.1MPa to be passed through carbon dioxide and keep pressure, under the conditions of temperature is 25 DEG C, after stirring 12h, and room temperature cooling, slowly release
After remaining carbon dioxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 80%.
Embodiment 12
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.2mol%)Catalyst conjugation chromium
Porphyrin bibenzyl amine capillary copolymer material, 12.5mmol styrene oxides and 0.9mmol co-catalyst tetra-n-butyl ammonium bromides, lead to
It is 0.1MPa to enter carbon dioxide and keep pressure, and under the conditions of temperature is 25 DEG C, after stirring 48h, room temperature cooling, slowly release is surplus
After remaining carbon dioxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 74%.
Embodiment 13
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.2mol%)Catalyst conjugation chromium
Porphyrin bibenzyl amine capillary copolymer material, 12.5mmol phenyl glycidyl ethers and 0.675mmol co-catalyst tetra-n-butyl bromines
Change ammonium, it is 0.1MPa to be passed through carbon dioxide and keep pressure, under the conditions of temperature is 25 DEG C, after stirring 24h, room temperature cooling, is delayed
After the remaining carbon dioxide of On The Drug Release, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 72%.
Embodiment 14
The method that the chromium-based catalysts chemical recycling of carbon dioxide of the present embodiment prepares cyclic carbonate, step are as follows:
Into 10mL stainless steel autoclave, 50mg is sequentially added(Active component chromium 0.3mol%)Catalyst conjugation chromium
Porphyrin bibenzyl amine capillary copolymer material, 12.5mmol cyclohexene oxides and 0.45mmol co-catalyst tetra-n-butyl ammonium bromides,
It is 0.1MPa to be passed through carbon dioxide and keep pressure, under the conditions of temperature is 25 DEG C, after stirring 12h, and room temperature cooling, slowly release
After remaining carbon dioxide, catalyst is filtered to isolate, the separation yield for obtaining cyclic carbonate after purification is 75%.
The content of active component is on the basis of the dosage of epoxide in above-described embodiment.
Claims (6)
1. a kind of method that chromium-based catalysts chemical recycling of carbon dioxide prepares cyclic carbonate, it is characterised in that using carbon dioxide and
Epoxides is as raw material, and to be conjugated chromium porphyrin capillary copolymer material as heterogeneous catalyst, tetra-n-butyl ammonium bromide is urged to help
Agent, in the case where normal temperature and pressure is solvent-free, 12-48h is reacted, realize efficient green catalysis carbon dioxide synthesizing annular carbonate.
2. the method that chromium-based catalysts chemical recycling of carbon dioxide according to claim 1 prepares cyclic carbonate, its feature exist
In:The conjugation chromium porphyrin capillary copolymer material uses Scholl coupling reactions, using chromium tetraphenylporphyrin as monomer, uses
Anhydrous AlCl3Catalyst preparation obtains, and its structural formula is as follows:
。
3. the method that chromium-based catalysts chemical recycling of carbon dioxide according to claim 1 prepares cyclic carbonate, its feature exist
In:The epoxide is expoxy propane, epoxy butane, epoxychloropropane, epoxy bromopropane, styrene oxide, phenyl contracting
Water glycerin ether or cyclohexene oxide.
4. the method that chromium-based catalysts chemical recycling of carbon dioxide according to claim 1 prepares cyclic carbonate, its feature exist
In:The dosage of the active component of the heterogeneous catalyst is 0.2~0.5mol% of epoxide dosage.
5. the method that chromium-based catalysts chemical recycling of carbon dioxide according to claim 1 prepares cyclic carbonate, its feature exist
In:The dosage of the co-catalyst is 3.6~7.2mol% of epoxide.
6. the method that cyclic carbonate is prepared according to any described chromium-based catalysts chemical recycling of carbon dioxide of claim 1 ~ 5, its
It is characterised by:The conjugation chromium porphyrin capillary copolymer material can use conjugation chromium porphyrin bibenzyl amine capillary copolymer material generation
Replace, the conjugation chromium porphyrin bibenzyl amine capillary copolymer material uses Scholl coupling reactions, with chromium tetraphenylporphyrin and benzyl
Amine is monomer, uses anhydrous AlCl3Catalyst preparation obtains, and its structural formula is as follows:
。
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CN112778533A (en) * | 2021-01-08 | 2021-05-11 | 广东工业大学 | Porphyrin-based porous organic polymer, preparation method thereof and synthesis method of cyclic carbonate |
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