CN110117225A - A kind of dialkyl group-α, the synthetic method of two carbonic ester of ω-alkylidene and its application in carbon dioxide absorption - Google Patents

A kind of dialkyl group-α, the synthetic method of two carbonic ester of ω-alkylidene and its application in carbon dioxide absorption Download PDF

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CN110117225A
CN110117225A CN201810113798.9A CN201810113798A CN110117225A CN 110117225 A CN110117225 A CN 110117225A CN 201810113798 A CN201810113798 A CN 201810113798A CN 110117225 A CN110117225 A CN 110117225A
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alkylidene
carbonic ester
dialkyl group
synthetic method
carbonate
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CN110117225B (en
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陈彤
石娅琴
汤志刚
王公应
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Chengdu Organic Chemicals Co Ltd of CAS
University of Chinese Academy of Sciences
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Chengdu Organic Chemicals Co Ltd of CAS
University of Chinese Academy of Sciences
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1456—Removing acid components
    • B01D53/1475—Removing carbon dioxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1493—Selection of liquid materials for use as absorbents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/205—Other organic compounds not covered by B01D2252/00 - B01D2252/20494
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
    • Y02C20/00—Capture or disposal of greenhouse gases
    • Y02C20/40—Capture or disposal of greenhouse gases of CO2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention belongs to carbonate material technical fields, and in particular to a kind of dialkyl group-α, the synthetic method of two carbonic ester of ω-alkylidene and its application in carbon dioxide absorption.For existing dialkyl group-α, that there are process efficiencies is low for two carbonic ester synthetic method of ω-alkylidene, not environmentally the disadvantages of.The technical scheme is that aliphatic dihydroxy alcohol, dialkyl carbonate and solid base catalyst are mixed, in atmospheric conditions, heating reaction obtains dialkyl group-α, two carbonic ester of ω-alkylidene.Furthermore the present invention also provides a kind of by dialkyl group-α, and two carbonic ester of ω-alkylidene is applied to the method for carbon dioxide absorption.It is industrial that the present invention is suitable for drug, cosmetics, fragrance, electrolyte, biological medicine and polymer etc..

Description

A kind of dialkyl group-α, the synthetic method of two carbonic ester of ω-alkylidene and its in titanium dioxide Application in carbon absorption
Technical field
The invention belongs to carbonate material technical fields, and in particular to a kind of dialkyl group-α, two carbonic ester of ω-alkylidene Synthetic method and its application in carbon dioxide absorption.
Background technique
Dialkyl group-α, two carbonic ester of ω-alkylidene is nontoxic, pollution-free, is mainly used for drug, cosmetics, fragrance, electrolysis Liquid, biological medicine and polymer industry.Its synthetic method mainly has phosgenation, oxidation carbonylation method and ester-interchange method.Traditional light Gas method is just gradually eliminated due to safety and environmental problem；Oxidation carbonylation method used catalyst is expensive and catalytic efficiency is lower, Limit its industrialization development；And ester-interchange method reaction condition is mild, reaction process is simple, solvent, product is added without additional High income and contamination of raw material are small.
Currently, transesterification synthesizes dialkyl group-α, two carbonic ester of ω-alkylidene mainly uses quaternary phosphonium salt, metal carbonyl complexes The catalyst such as object and adsorbent 4A molecular sieve.M.Selva etc. (Organic&Biomolecular Chemistry 2014,12: 4143-4155) catalytic performance of the methyl tri octyl phosphine methyl carbonate salt in such reaction is had studied, binary alcohol conversion > 99%, dialkyl group-α, two carbonic ester highest yield of ω-alkylidene is up to 90%.But methyl tri octyl phosphine methyl carbonate salt is equal There is separation, recycling, environmental pollution in phase catalyst.(the Russian Journal of such as R.I.Khusnutdinov Organic Chemistry.2014,50:948-952) using eight carbonyls, two cobalts of conjunction as catalyst, binary alcohol conversion is reachable 100%, dialkyl group-α, two carbonic ester highest yield of ω-alkylidene is up to 98%.But metal carbonyl complex preparation process is multiple It is miscellaneous, stability is poor, difficult separation and higher cost.It is not suitable for industrialized production.(the Advanced Synthesis such as S.H.Pyo Catalsis.2016,358:834-839) methanol adsorption agent made with 4A molecular sieve, binary alcohol conversion is up to 100%, dioxane Base-α, two carbonic ester highest yield of ω-alkylidene is up to 99%.But 4A molecular sieve as adsorbent dosage in the reaction compared with Greatly, easily adsorbed product and solvent, have seriously affected the high efficiency of technique.
In conclusion existing dialkyl group-α, that there are process efficiencies is low for two carbonic ester synthetic method of ω-alkylidene, not ring The disadvantages of guarantor.Therefore, transesterification synthesis dialkyl group-α highly efficient, cheap, that preparation process is succinct and environmental-friendly is developed, The method of two carbonic ester of ω-alkylidene has great importance and industrial application value.
Global warming has caused a series of environmental problems.According to assessment report, the average earth's surface in the whole world warms mainly Depending on accumulating CO2Discharge amount.The trapping of carbon dioxide and Plugging Technology Applied are considered as stablizing atmospheric carbon dioxide levels most Efficiently and effectively approach.Integral gasification combined circulation technology (IGCC) and pre-combustion capture technology combine, and are expected to reality Existing CO2Near-zero release has become a hot topic of research.Pre-combustion capture most critical technology is CO2Separation, common separation method has: Absorption and sorption, UF membrane etc., absorption process have preferable selectivity, and application is more.Typical physical absorbent has methanol, gathers Glycol dimethyl ether, propene carbonate, N-Methyl pyrrolidone etc..Industrialized propene carbonate absorbent properties are preferable.N- first Base pyrrolidones 1MPa, 30 DEG C of absorptive capacities be 0.12mol/mol (Gui Xia, Tang Zhigang, Fei Weiyang chemical engineering .2011, 39:55-58；The Hangzhou Zhou Xueliang: Zhejiang science tech publishing house .1993,3-5).Propene carbonate holds in 1MPa, 30 DEG C of absorptions Amount is 0.14mol/mol (Li Tiezhi, Tang Zhigang, Hu Hui, Guo Dong colleges and universities chemical engineering journal .2012,26:1-6).
But existing CO2The absorbability of absorbent is still lower, and there are also the spaces promoted.
Summary of the invention
For existing dialkyl group-α, that there are process efficiencies is low for two carbonic ester synthetic method of ω-alkylidene, not environmentally etc. lacks Point.The present invention provides a kind of dialkyl group-α, the synthetic method of two carbonic ester of ω-alkylidene, its object is to: so that synthesis has Efficiently, inexpensively, the succinct and environmental-friendly advantage of preparation process.
It is a further object of the present invention to provide a kind of dialkyl group-α, and two carbonic ester of ω-alkylidene is in carbon dioxide absorption Application, its object is to: a kind of couple of CO is provided2Absorbent with stronger absorbability.
The technical solution adopted by the invention is as follows:
A kind of dialkyl group-α, the synthetic method of two carbonic ester of ω-alkylidene, include the following steps: by aliphatic dihydroxy alcohol, Dialkyl carbonate and solid base catalyst mixing are heated to 65-90 DEG C of reaction, obtain dialkyl group-α in atmospheric conditions, Two carbonic ester of ω-alkylidene.
After the technical solution, catalyst uses the simple substance or mixture of solid base, and the method for preparing catalyst is simple, And the temperature heated when having good catalytic performance, thus react and carry out in atmospheric conditions, and reacting is 65-90 DEG C, reaction condition is as mild as a dove.Thus the synthetic method has the advantages that at low cost and environmental-friendly.In addition, solid base is easy Separated with reaction product, can simplification of flowsheet, improve process efficiency.
Preferably, aliphatic dihydroxy alcohol isR1For alkylidene；The dialkyl carbonate is R2For alkyl；Obtained dialkyl group-α is synthesized, two carbonic ester of ω-alkylidene is
It, can be by adjusting R using the preferred embodiment1And R2Obtain the dialkyl group-α, ω-Asia with different chemical environments Two carbonic ester of alkyl, furthermore R1Variation can also adjust the distance between carbonic ester.
Preferably, solid base catalyst is alkali metal oxide, alkali metal hydroxide, alkali carbonate, alkali metal One of acetate, alkaline earth oxide, alkaline earth metal hydroxide, alkaline earth metal carbonate or alkaline earth metal acetates Or it is a variety of.
The selection multiplicity of solid base catalyst, can select according to the actual condition of production.
A kind of dialkyl group-α, application of two carbonic ester of ω-alkylidene in carbon dioxide absorption, by dialkyl group-α, ω-Asia Two carbonic ester of alkyl is used as carbon-dioxide absorbent.
In the prior art, propene carbonate as the principle of effective carbon-dioxide absorbent be due to the similar principle that mixes, Compound with carbonate functionalities has stronger physical force to carbon dioxide.And in the technical program, dialkyl group- α, there are two carbonate functionalities for tool in two carbonic ester of ω-alkylidene, the alkylidene fat between two carbonate functionalities In the suitable situation of chain length, two carbonate functionalities can simultaneously be acted on carbon dioxide, to enhance dioxy Change the solubility of carbon.Furthermore after carbon dioxide is in conjunction with two carbonate functionalities, the alkyl group positioned at both ends can be provided Certain steric hindrance hinders carbon dioxide far from carbonate functionalities to further enhance carbon dioxide and two carbonic ester officials The active force that can be rolled into a ball, and then enhance the solubility of carbon dioxide.Due to the above reasons, compared with the prior art in common carbon Acid propylene ester, dialkyl group-α, two carbonic ester of ω-alkylidene have stronger carbon dioxide solubility ability, are more suitable as two The absorbent of carbonoxide is industrially applied.
In conclusion by adopting the above-described technical solution, the beneficial effects of the present invention are:
1. method for preparing catalyst is simple, and has good catalytic performance, thus reaction carries out in atmospheric conditions, And the temperature heated when reacting is 65-90 DEG C, and reaction condition is as mild as a dove.Thus the synthetic method has at low cost and environment Friendly advantage.
2. solid base be easy separated with reaction product, can simplification of flowsheet, raising process efficiency.
3. synthesis process is without additional addition solvent and methanol adsorption agent, environmental-friendly.
4. can be by adjusting R1And R2Dialkyl group-α of the acquisition with different chemical environments, two carbonic ester of ω-alkylidene, Furthermore R1Variation can also adjust the distance between carbonic ester.
5. the selection multiplicity of solid base catalyst, can select according to the actual condition of production.
6. common propene carbonate in compared with the prior art, dialkyl group-α, two carbonic ester of ω-alkylidene have stronger Carbon dioxide solubility ability, be more suitable and industrially applied as the absorbent of carbon dioxide.
Detailed description of the invention
Fig. 1: dialkyl group-α, two carbonic ester of ω-alkylidene is to CO2Absorptive capacity.
Specific embodiment
All features disclosed in this specification or disclosed all methods or in the process the step of, in addition to mutually exclusive Feature and/or step other than, can combine in any way.
Embodiment 1
0.025mol 1,3- propylene glycol, 0.75mol carbonic acid are added in the two-mouth bottle for being connected with condensing reflux pipe and thermometer Dimethyl ester, 0.17mol magnesia catalyst.Under normal pressure, 4h is reacted at a temperature of 80 DEG C.After being separated by filtration catalyst, obtain Reaction solution containing two carbonic ester of dimethyl -1,3- propylidene.The reaction solution of two carbonic ester of dimethyl -1,3- propylidene is carried out Vacuum distillation can isolated two carbonic ester product of dimethyl -1,3- propylidene.
Embodiment 2
The synthesis that two carbonic ester of dimethyl -1,3- butylidene is carried out in the method for embodiment 1, replaces with 1,3- for dihydric alcohol Butanediol.Catalyst replaces with MgO-K2O.Reaction temperature is 75 DEG C, reaction time 6h.Other conditions are consistent.
Embodiment 3
The synthesis of diethyl-two carbonic ester of Isosorbide-5-Nitrae-butylidene is carried out in the method for embodiment 1, dihydric alcohol is replaced with into Isosorbide-5-Nitrae- Butanediol, dialkyl carbonate are diethyl carbonate.Catalyst is calcium carbonate.Reaction temperature is 90 DEG C, reaction time 2h.Its Other conditions are consistent.
Embodiment 4
The synthesis that two carbonic ester of dimethyl -1,5- pentylidene is carried out in the method for embodiment 1, replaces with 1,5- for dihydric alcohol Pentanediol.Catalyst is sodium hydroxide.Reaction temperature is 65 DEG C, reaction time 8h.Other conditions are consistent.
Embodiment 5
The synthesis of dimethyl -1,2- ethylene carbonic ester is carried out in the method for embodiment 1, but dihydric alcohol is 1,2- second two Alcohol.Catalyst is potassium acetate.Reaction temperature is 75 DEG C, reaction time 0.5h.Other conditions are consistent.
To two alcohol conversions and dialkyl group-α of the embodiment 1 into embodiment 5, the yield of two carbonic ester of ω-alkylidene into Row analysis, obtained reaction solution is analyzed with Agilent 7820A type chromatograph, uses inner mark method ration.Its result such as following table It is shown.
Dialkyl group-the α of above-mentioned synthesis, two carbonic ester of ω-alkylidene are suitable as efficient CO2Absorbent.With embodiment 1 For two carbonic ester of dimethyl -1,3- propylidene of synthesis.Using vascular unloading technique in 30 DEG C of measurement dimethyl -1,3- propylidene Two carbonic esters are to CO2Absorptive capacity.As a result as shown in Figure 1.It is upper as it can be seen that two carbonic ester of dimethyl -1,3- propylidene exists from figure 1MPa, CO at 30 DEG C2Absorptive capacity is up to 0.21mol/mol.Existing propene carbonate is under the conditions of same to CO2Absorptive capacity For 0.14mol/mol, i.e., under this condition two carbonic ester of dimethyl -1,3- propylidene to CO2Absorbability improve 50%.
The specific embodiment of the application above described embodiment only expresses, the description thereof is more specific and detailed, but simultaneously The limitation to the application protection scope therefore cannot be interpreted as.It should be pointed out that for those of ordinary skill in the art For, under the premise of not departing from technical scheme design, various modifications and improvements can be made, these belong to this The protection scope of application.

Claims (4)

1. a kind of dialkyl group-α, the synthetic method of two carbonic ester of ω-alkylidene, which comprises the steps of: will be fatty Race's dihydric alcohol, dialkyl carbonate and solid base catalyst mixing are heated to 65-90 DEG C of reaction, obtain two in atmospheric conditions Alkyl-α, two carbonic ester of ω-alkylidene.
2. a kind of dialkyl group-α described in accordance with the claim 1, the synthetic method of two carbonic ester of ω-alkylidene, it is characterised in that: The aliphatic dihydroxy alcohol isR1For alkylidene；The dialkyl carbonate isR2For alkyl；It closes At obtained dialkyl group-α, two carbonic ester of ω-alkylidene is
3. a kind of dialkyl group-α described in accordance with the claim 1, the synthetic method of two carbonic ester of ω-alkylidene, it is characterised in that: The solid base catalyst is alkali metal oxide, alkali metal hydroxide, alkali carbonate, alkali metal acetate, alkaline earth One of metal oxide, alkaline earth metal hydroxide, alkaline earth metal carbonate or alkaline earth metal acetates are a variety of.
4. a kind of dialkyl group-α, application of two carbonic ester of ω-alkylidene in carbon dioxide absorption, it is characterised in that: by dioxane Base-α, two carbonic ester of ω-alkylidene are used as carbon-dioxide absorbent.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116655471A (en) * 2023-05-23 2023-08-29 杭州元素添加剂科技有限公司 Method for purifying dicarbonate diester compound

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
C. ROBERT MCEIROY ET AL.: "Cyclization reaction of amines with dialkyl carbonates to yield 1,3-oxazinan-2-ones", 《PURE APPL.CHEM.》 *
FABIO ARICO ET AL.: "Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate", 《CHEMSUSCHEM》 *
桂霞等: "高压下CO2在几种物理吸收剂中的溶解度测定", 《化学工程》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116655471A (en) * 2023-05-23 2023-08-29 杭州元素添加剂科技有限公司 Method for purifying dicarbonate diester compound
CN116655471B (en) * 2023-05-23 2023-11-17 杭州元素添加剂科技有限公司 Method for purifying dicarbonate diester compound

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