CN113200820A - Method for separating dimethyl carbonate and methanol by using imidazole ionic liquid - Google Patents
Method for separating dimethyl carbonate and methanol by using imidazole ionic liquid Download PDFInfo
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- CN113200820A CN113200820A CN202110498468.8A CN202110498468A CN113200820A CN 113200820 A CN113200820 A CN 113200820A CN 202110498468 A CN202110498468 A CN 202110498468A CN 113200820 A CN113200820 A CN 113200820A
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 130
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 91
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 42
- 238000000622 liquid--liquid extraction Methods 0.000 claims abstract description 32
- 238000000638 solvent extraction Methods 0.000 claims abstract description 32
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 238000000605 extraction Methods 0.000 claims abstract description 18
- 238000000926 separation method Methods 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 17
- GUNDKLAGHABJDI-UHFFFAOYSA-N dimethyl carbonate;methanol Chemical compound OC.COC(=O)OC GUNDKLAGHABJDI-UHFFFAOYSA-N 0.000 claims description 13
- RVEJOWGVUQQIIZ-UHFFFAOYSA-N 1-hexyl-3-methylimidazolium Chemical compound CCCCCCN1C=C[N+](C)=C1 RVEJOWGVUQQIIZ-UHFFFAOYSA-N 0.000 claims description 4
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical compound CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 230000008901 benefit Effects 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 description 13
- 239000012528 membrane Substances 0.000 description 9
- 239000012466 permeate Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000005373 pervaporation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- -1 carbonyl methoxy Chemical group 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005832 oxidative carbonylation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
-
- 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
- Y02P20/10—Process efficiency
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for separating dimethyl carbonate and methanol by using imidazole ionic liquid and a device suitable for the method. The method uses imidazole ionic liquid as an extracting agent, dimethyl carbonate and methanol firstly enter a liquid-liquid extraction tower for extraction and separation, materials at the bottom of the liquid-liquid extraction tower enter a flash tank for separation, high-purity dimethyl carbonate is obtained at the top of the extraction tower, and the extracting agent is recycled after being extracted from the bottom of the flash tank. The method has the advantages of low energy consumption, simple process, high purity of the separated dimethyl carbonate and methanol and the like, the adopted extractant imidazole ionic liquid is almost non-volatile, the loss of the extractant is reduced, and the method is easy to recover, good in chemical thermal stability, green and pollution-free.
Description
[ technical field ] A method for producing a semiconductor device
The invention belongs to the field of chemical separation and purification, and particularly relates to a method for separating methanol and dimethyl carbonate by using imidazole ionic liquid, namely a method for separating methanol and dimethyl carbonate by using imidazole ionic liquid through a liquid-liquid extraction method, and then recovering and utilizing ionic liquid through flash evaporation.
[ background of the invention ]
Dimethyl carbonate (DMC), a low toxicity, environmental protection, excellent, use extensive chemical raw materials, it is an important organic synthesis intermediate, because its molecular structure contains carbonyl, methyl, methoxy and carbonyl methoxy, so can be used in carbonylation, methylation, methoxy and carbonyl methylation organic synthesis reaction, it is a "green" chemical product with development prospect. Among the DMC synthesis processes, the transesterification process and the oxidative carbonylation process are the most promising industrial ones, but since complete conversion of methanol (MeOH) is always difficult to achieve, the end result is a mixture of dimethyl carbonate and methanol, which is an azeotrope that is difficult to separate, and dimethyl carbonate and methanol must be separated to obtain pure dimethyl carbonate.
The azeotropic temperature of DMC-MeOH under normal pressure was 63.7 ℃ and the azeotropic composition was 70% by mass of methanol (hereinafter, the same applies) and 30% by mass of dimethyl carbonate. The common rectification separation process is difficult to achieve the required high-purity product, and the purity of the dimethyl carbonate product directly influences the production benefit, so the research of the methanol-dimethyl carbonate azeotrope separation process is particularly important.
Imidazole ionic liquids such as [ MIM ] [ HSO4], [ HMIM ] [ PF6], [ OMIM ] [ OTF ] and the like, and [ MIM ] [ PF6] is taken as an example in the patent to illustrate a method for separating dimethyl carbonate-methanol by liquid-liquid extraction of imidazole plasma.
Chinese patent CN104370699B discloses a method for separating methanol-dimethyl carbonate azeotropic liquid, which utilizes different permselectivity of pervaporation membranes to component adsorption, effectively breaks through the azeotropic bottleneck of methanol-dimethyl carbonate, the side feed liquid with low concentration of dimethyl carbonate returns to a reaction rectifying tower for circular separation, the side feed liquid with high concentration of dimethyl carbonate is conveyed to a normal pressure rectifying tower, and the dimethyl carbonate product with the mass purity of more than 99.6 percent is obtained at the tower bottom after the separation of the normal pressure rectifying tower.
Chinese patent CN101143803 discloses a process for the separation of dimethyl carbonate and methanol azeotropes by pervaporation-rectification integration. The method comprises the steps of conveying azeotrope saturated steam to a membrane separator to contact with a separation membrane, allowing dimethyl carbonate to permeate the membrane and concentrate on the permeation side of the membrane, condensing the dimethyl carbonate into liquid under vacuum and low pressure, directly feeding the liquid into a normal pressure rectifying tower, obtaining over 99.5% of dimethyl carbonate at the bottom of the tower, and obtaining high-concentration methanol at the interception side of the membrane. The patent preferentially permeates the dimethyl carbonate component with low content in the membrane, which is beneficial to reducing the area of the membrane and reducing the investment.
Chinese patent CN103084076 describes a method for preparing a hollow fiber membrane for separating a mixture of methanol and dimethyl carbonate and its application, the mixture of methanol and dimethyl carbonate to be separated is filled into a feed liquid tank, the feed liquid permeates from the feed liquid side to the permeate side through a permeate component, a vacuum pump is used to provide negative pressure at the permeate side, and permeate liquid is collected in a cold trap. However, the above patents only show that the pervaporation separation experiments show higher selectivity and greater permeation flux, and do not relate to industrial applications, and it can be expected that the collected permeate needs to be further separated.
The imidazole ionic liquid-liquid extraction-flash evaporation device is used for realizing high-purity recovery of dimethyl carbonate in a dimethyl carbonate-methanol mixture, and the purity of the separated dimethyl carbonate is up to more than 99.96 percent by using [ MIM ] [ PF6] ionic liquid as an extractant and utilizing the characteristic of high solubility of methanol in the extractant; the extraction agent has the characteristics of high thermal stability and chemical stability, very small vapor pressure, non-volatility and the like, so that the extraction agent can be recycled, the separation cost is reduced, and the method has low energy consumption and simple process.
[ summary of the invention ]
[ problem to be solved ]
The invention aims to provide a method for separating a mixture by liquid-liquid extraction of imidazole ionic liquid and efficiently recovering the ionic liquid.
The invention also aims to provide a method for separating methanol-dimethyl carbonate by using the device and recovering the ionic liquid through liquid-liquid extraction of the imidazole ionic liquid.
The invention also aims to provide the application of the imidazole salt ionic liquid as an extracting agent in liquid-liquid extraction-flash separation of methanol and methyl carbonate.
[ solution ]
The invention is realized by the following technical scheme.
A method for separating dimethyl carbonate and methanol by using imidazole ionic liquid is characterized in that a device for realizing the method mainly comprises the following parts: liquid-liquid extraction column (LET), flash tank (FLA), Condenser (COL), Mixer (MIX); wherein the bottom of the liquid-Liquid Extraction Tower (LET) is connected with an inlet of the flash tank (FLA) and is connected into the flash tank (FLA), the bottom of the flash tank (FLA) enters the Mixer (MIX) through the Condenser (COL), and the recovered ionic liquid and the supplemented fresh ionic liquid enter the extraction tower (LET) through the Mixer (MIX) and the top of the extraction tower (LET). The components to be separated enter via the bottom of an extraction column (LET).
The method for separating dimethyl carbonate and methanol by using the imidazole ionic liquid comprises the following steps:
(1) the method comprises the following steps that a mixture of dimethyl carbonate and methanol enters from the bottom of a liquid-Liquid Extraction Tower (LET), an extracting agent enters from the top of the liquid-Liquid Extraction Tower (LET), after effective contact extraction and separation, the dimethyl carbonate flows out from the top of the extraction tower (LET), and the methanol and ionic liquid flow out from the bottom of the extraction tower (LET) and enter a flash tank (FLA);
(2) after flash evaporation through a flash tank (FLA), methanol flows out from the top material flow, the material flow at the bottom of the flash tank (FLA) is almost pure ionic liquid, the ionic liquid enters a Cooler (COL) for cooling, and then enters a Mixer (MIX) and enters a liquid-Liquid Extraction Tower (LET) together with supplemented fresh ionic liquid for recycling;
the extracting agent is imidazole ionic liquid.
According to another preferred embodiment of the invention, it is characterized in that: the imidazole ionic liquid has the characteristics of high thermal stability and chemical stability, very small vapor pressure, non-volatility and the like, and common imidazole ionic liquids comprise [ MIM ] [ PF6], [ MIM ] [ PF6], [ HMIM ] [ PF6], [ OMIM ] [ OTF ] and the like, which shows the method for separating dimethyl carbonate-methanol by imidazole plasma liquid-liquid extraction.
According to another preferred embodiment of the invention, it is characterized in that: the liquid-Liquid Extraction Tower (LET) has the operating pressure of normal pressure, 5-10 tower plates, the feeding temperature of the ionic liquid of 25 ℃, the operating pressure of a flash tank (FLA) of 0.5bar and the flash temperature of 150 ℃.
According to another preferred embodiment of the invention, it is characterized in that: the mass ratio of the feed flow of the extracting agent to the feed flow of the methanol-dimethyl carbonate mixture is 0.3-0.5.
According to another preferred embodiment of the invention, it is characterized in that: in the binary mixed solution of methanol and dimethyl carbonate, the mass fraction of methanol is 20-30% and the mass fraction of dimethyl carbonate is 80-70%.
According to another preferred embodiment of the invention, it is characterized in that: the purity of the ionic liquid recovered from the bottom of the flash tank (FLA) is higher than 99.91%, and the recycling rate is higher than 99.91%.
[ advantageous effects ]
Compared with the prior art, the invention mainly has the following beneficial effects:
(1) the method is adopted to separate the dimethyl carbonate and the methanol to obtain the high-purity dimethyl carbonate, so that the high-purity component can be obtained from the binary azeotropic mixture, and the problem that the dimethyl carbonate and the methanol are difficult to separate is solved.
(2) The method has the advantages of simple process, less investment equipment, high purity of the separated dimethyl carbonate, high recovery rate and the like, and the adopted extractant imidazole ionic liquid is easy to recover, good in chemical thermal stability, green and pollution-free.
(3) The adopted extractant imidazole ionic liquid is almost non-volatile, the loss of the extractant is reduced, the secondary pollution of dimethyl carbonate and methanol is avoided, in addition, the extractant is easy to recycle, and the separation cost is reduced.
[ description of the drawings ]
FIG. 1 is a process flow diagram for the liquid-liquid extraction-flash separation of phenol and water according to the present invention.
In the figure, LET-liquid extraction column; FLA-flash tank; a COL-cooler; a MIX-mixer; the numbers represent the respective lines.
[ detailed description ] embodiments
Example 1:
the feed flow is 1000kg/h, the feed contains 20% of methanol and 80% of dimethyl carbonate (mass fraction), the number of theoretical plates of a liquid-Liquid Extraction Tower (LET) is 9, a mixture of phenol and water enters from the bottom of the liquid-Liquid Extraction Tower (LET), an extracting agent enters from the top of the liquid-Liquid Extraction Tower (LET), the extracting agent is [ OMIM ] [ OTF ] ionic liquid, the flow is 500kg/h (the feed flow mass ratio of the extracting agent to the dimethyl carbonate-methanol mixture is 0.5), and the temperature of the liquid-Liquid Extraction Tower (LET) is 16 ℃. The operating pressure of the flash tank (FLA) was 0.4bar, the purity of the separated dimethyl carbonate was 99.90% and the purity of the ionic liquid was 99.91%.
Example 2:
the feed flow is 1000kg/h, the feed contains 20% of methanol and 80% of dimethyl carbonate (mass fraction), the theoretical plate number of a liquid-Liquid Extraction Tower (LET) is 9, a mixture of phenol and water enters from the bottom of the liquid-Liquid Extraction Tower (LET), an extracting agent enters from the top of the liquid-Liquid Extraction Tower (LET), the extracting agent is [ MIM ] [ PF6] ionic liquid, the flow is 500kg/h (the feed flow mass ratio of the extracting agent to the dimethyl carbonate-methanol mixture is 0.5), and the temperature of the liquid-Liquid Extraction Tower (LET) is 16 ℃. The operating pressure of the flash tank (FLA) was 0.4bar, the purity of the separated dimethyl carbonate was 99.95% and the purity of the ionic liquid was 99.91%.
Example 3:
the feed flow is 1000kg/h, the feed contains 20% of methanol and 80% of dimethyl carbonate (mass fraction), the number of theoretical plates of a liquid-Liquid Extraction Tower (LET) is 9, a mixture of phenol and water enters from the bottom of the liquid-Liquid Extraction Tower (LET), an extracting agent enters from the top of the liquid-Liquid Extraction Tower (LET), the extracting agent is [ HMIM ] [ PF6] ionic liquid, the flow is 500kg/h (the feed flow mass ratio of the extracting agent to the dimethyl carbonate-methanol mixture is 0.5), and the temperature of the liquid-Liquid Extraction Tower (LET) is 16 ℃. The operating pressure of the flash tank (FLA) was 0.4bar, the purity of the separated dimethyl carbonate was 99.97%, and the purity of the ionic liquid was 99.91%.
Claims (6)
1. A method for separating dimethyl carbonate and methanol by using imidazole ionic liquid is characterized in that a device for realizing the method mainly comprises the following parts: liquid-liquid extraction column (LET), flash tank (FLA), Condenser (COL), Mixer (MIX); wherein the bottom of the liquid-Liquid Extraction Tower (LET) is connected with an inlet of the flash tank (FLA) and is connected into the flash tank (FLA), the bottom of the flash tank (FLA) enters a Mixer (MIX) through a Condenser (COL), the recovered ionic liquid and supplemented fresh ionic liquid enter the extraction tower (LET) through the Mixer (MIX) and the top of the extraction tower (LET), and components to be separated enter the extraction tower (LET) through the bottom of the extraction tower (LET);
the method for separating dimethyl carbonate and methanol by using the imidazole ionic liquid comprises the following steps:
(1) the method comprises the following steps that a mixture of dimethyl carbonate and methanol enters from the bottom of a liquid-Liquid Extraction Tower (LET), an extracting agent enters from the top of the liquid-Liquid Extraction Tower (LET), after effective contact extraction and separation, the dimethyl carbonate flows out from the top of the extraction tower (LET), and the methanol and ionic liquid flow out from the bottom of the extraction tower (LET) and enter a flash tank (FLA);
(2) after flash evaporation through a flash tank (FLA), methanol flows out from the top material flow, the material flow at the bottom of the flash tank (FLA) is almost pure ionic liquid, the ionic liquid enters a Cooler (COL) for cooling, and then enters a Mixer (MIX) and enters a liquid-Liquid Extraction Tower (LET) together with supplemented fresh ionic liquid for recycling;
the extracting agent is imidazole ionic liquid.
2. The method for separating dimethyl carbonate from methanol by using the imidazole ionic liquid as claimed in claim 1, which is characterized in that: the imidazole ionic liquid has the characteristics of high thermal stability and chemical stability, very small vapor pressure, non-volatility and the like, and common imidazole ionic liquids comprise [ MIM ] [ PF6], [ MIM ] [ PF6], [ HMIM ] [ PF6], [ OMIM ] [ OTF ] and the like, which shows the method for separating dimethyl carbonate-methanol by imidazole plasma liquid-liquid extraction.
3. The method for separating dimethyl carbonate from methanol by using the imidazole ionic liquid as claimed in claim 1, which is characterized in that: the liquid-Liquid Extraction Tower (LET) has the operating pressure of normal pressure, 5-10 tower plates, the feeding temperature of the ionic liquid of 25 ℃, the operating pressure of a flash tank (FLA) of 0.5bar and the flash temperature of 150 ℃.
4. The method for separating dimethyl carbonate from methanol by using the imidazole ionic liquid as claimed in claim 1, which is characterized in that: the mass ratio of the feed flow of the extracting agent to the feed flow of the methanol-dimethyl carbonate mixture is 0.3-0.5.
5. The method for separating dimethyl carbonate from methanol by using the imidazole ionic liquid as claimed in claim 1, which is characterized in that: in the binary mixed solution of methanol and dimethyl carbonate, the mass fraction of methanol is 20-30% and the mass fraction of dimethyl carbonate is 80-70%.
6. The method for separating dimethyl carbonate from methanol by using the imidazole ionic liquid as claimed in claim 1, which is characterized in that: the purity of the ionic liquid recovered from the bottom of the flash tank (FLA) is higher than 99.91%, and the recycling rate is higher than 99.91%.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0616596A (en) * | 1992-07-01 | 1994-01-25 | Asahi Chem Ind Co Ltd | Separation of dimethyl carbonate from methanol |
| JPH0625104A (en) * | 1991-07-19 | 1994-02-01 | Ube Ind Ltd | Continuous production of dimethyl carbonate |
| CN107915642A (en) * | 2016-10-10 | 2018-04-17 | 中国石油化工股份有限公司 | The separation method of dimethyl carbonate and methanol |
| CN111004092A (en) * | 2019-12-26 | 2020-04-14 | 岳阳昌德环境科技有限公司 | Method for separating dimethyl carbonate and methanol |
| CN112225634A (en) * | 2020-10-02 | 2021-01-15 | 洪泽县恒泰科工贸有限公司 | Method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation |
-
2021
- 2021-05-08 CN CN202110498468.8A patent/CN113200820B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0625104A (en) * | 1991-07-19 | 1994-02-01 | Ube Ind Ltd | Continuous production of dimethyl carbonate |
| JPH0616596A (en) * | 1992-07-01 | 1994-01-25 | Asahi Chem Ind Co Ltd | Separation of dimethyl carbonate from methanol |
| CN107915642A (en) * | 2016-10-10 | 2018-04-17 | 中国石油化工股份有限公司 | The separation method of dimethyl carbonate and methanol |
| CN111004092A (en) * | 2019-12-26 | 2020-04-14 | 岳阳昌德环境科技有限公司 | Method for separating dimethyl carbonate and methanol |
| CN112225634A (en) * | 2020-10-02 | 2021-01-15 | 洪泽县恒泰科工贸有限公司 | Method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation |
Non-Patent Citations (1)
| Title |
|---|
| CAI FUFENG等: "A study on the liquid–liquid equilibrium of 1-alkyl-3-methylimidazolium dialkylphosphate with methanol and dimethyl carbonate", 《FLUID PHASE EQUILIBRIA》 * |
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