CN109400475A - A kind of preparation method of R- propene carbonate - Google Patents
A kind of preparation method of R- propene carbonate Download PDFInfo
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- CN109400475A CN109400475A CN201811349047.3A CN201811349047A CN109400475A CN 109400475 A CN109400475 A CN 109400475A CN 201811349047 A CN201811349047 A CN 201811349047A CN 109400475 A CN109400475 A CN 109400475A
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- esterification
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- mixed liquor
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0241—Imines or enamines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
-
- 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
- C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to field of new materials, and in particular to a kind of preparation method of R- propene carbonate, comprising: esterification；Recycle the by-product of esterification；And the product of distilation esterification, obtain the R- propene carbonate.The purity for having lacked R- propene carbonate is improved, reduces the discharge and processing of by-product and unwanted contaminants, reduces production cost.
Description
Technical field
The present invention relates to field of new materials, and in particular to a kind of preparation method of R- propene carbonate.
Background technique
R- propene carbonate is the key intermediate for synthesizing tenofovir (Tenofovir).Tenofovir is anti-AIDS
First-line drug, therefore R- propene carbonate is held in both hands by market heat naturally, and demand rises every year.And R- carbonic acid is produced at present
The method of acrylic ester is to obtain (R)-propylene oxide from racemic epoxide propane Hydrolysis Resolution, then produce the production with carbon dioxide reaction
Product.The high requirements on the equipment, production risk is big, while the purity of obtained R- propene carbonate is lower.
Summary of the invention
The object of the present invention is to provide a kind of preparation methods of R- propene carbonate, to improve the pure of R- propene carbonate
Degree.
In order to solve the above-mentioned technical problems, the present invention provides a kind of preparation methods of R- propene carbonate, comprising: esterification
Reaction；Recycle the by-product of esterification；And the product of distilation esterification, obtain the R- propene carbonate.
Further, dimethyl carbonate and (R) -1,2-PD are added in reaction kettle, are then added that schiff bases is compound to urge
Agent, heating carry out the esterification.
Further, the temperature of the esterification is 65-68 DEG C.
Further, the method for the by-product of the recycling esterification includes: to carry out the reactant after esterification often
Pressure distillation, to steam by-product；It is recycled by condensing and separating；And fixed gas enters exhaust treatment system.
Further, the mode of the condensation is in such a way that level-one water cooling and level-one chilled brine combine.
Further, the product of esterification is added in vacuum distillation kettle and is evaporated under reduced pressure, obtain the propylene carbonate
Ester；And the raffinate in vacuum distillation kettle is dead catalyst mixed liquor.
Further, the preparation method further include: bring back to life dead catalyst mixed liquor；The resurrection dead catalyst mixed liquor
Method includes: that water and glacial acetic acid are added into dead catalyst mixed liquor；Centrifugation, filtering, obtain solid phase；And it is added into solid phase
Methanol and sodium methoxide, as Schiff alkali composite catalyst.
Another aspect, the present invention also provides a kind of methods for bringing back to life dead catalyst mixed liquor, comprising: to foregoing
Water and glacial acetic acid are added in dead catalyst mixed liquor；Centrifugation, filtering, obtain solid phase；And methanol and methanol are added into solid phase
Sodium, as Schiff alkali composite catalyst.
The invention has the advantages that preparation method of the invention generates product (R- propene carbonate) by esterification
With by-product (methanol), then by by-product recovery, product distilation, preparation process is simple, save the cost, environmentally protective
Advantage, the R- propene carbonate purity is high of preparation, impurity are few；Further, it is also possible to make seat by bringing back to life dead catalyst mixed liquor
Husband's alkali composite catalyst is recycled, and reduces production cost.
Detailed description of the invention
Present invention will be further explained below with reference to the attached drawings and examples.
Fig. 1 is the process flow diagram of preparation method of the invention.
Specific embodiment
In conjunction with the accompanying drawings, the present invention is further explained in detail.
Embodiment 1
As shown in Figure 1, the present embodiment 1 provides a kind of preparation method of R- propene carbonate, comprising: esterification；Recycle ester
Change the by-product of reaction；And the product of distilation esterification, obtain the R- propene carbonate.Now to preparation method
Each preparation section is specifically described.
(1) esterification.
Dimethyl carbonate and (R) -1,2-PD are added in reaction kettle, Schiff alkali composite catalyst, control are then instilled
Reaction temperature processed reacts 6h at 65-68 DEG C.
(2) by-product is recycled.
Esterification can generate by-product carbinol and product R- propene carbonate.
Air-distillation is carried out to reactant after esterification, steams by-product carbinol；Using level-one water cooling and one
The condensing mode that grade chilled brine combines, separating methanol is recycled, both to reduce for bringing back to life Schiff alkali composite catalyst
The discharge amount of by-product, and the discharge and processing of waste can be reduced.Fixed gas is discharged into exhaust treatment system simultaneously, is prevented
Pollute environment.
(3) distilation product.
Reactant is pumped into vacuum distillation kettle again and is evaporated under reduced pressure, obtains the R- propene carbonate that purity is 99%；With
And the raffinate in vacuum distillation kettle is dead catalyst mixed liquor.
(4) dead catalyst is brought back to life.
Water and glacial acetic acid are added into dead catalyst mixed liquor；It is dissolved and neutralizes remaining methanol；Then to neutralization
Liquid centrifugation, filtering, obtain solid phase；Methanol and sodium methoxide, i.e. Schiff alkali composite catalyst are added into solid phase.And liquid phase is flowed into and is given up
Water treatment system.
In conclusion the preparation method of the application generates product (R- propene carbonate) and by-product by esterification
(methanol), then by by-product recovery, product distilation, preparation process is simple, save the cost, environmentally protective advantage,
The R- propene carbonate purity is high of preparation, impurity are few；Further, it is also possible to which bringing back to life dead catalyst mixed liquor makes schiff bases composite catalyzing
Agent is recycled, but also by-product carbinol continues to use, also reduces the discharge and processing of by-product and unwanted contaminants,
Reduce production cost.
Embodiment 2
On the basis of embodiment 1, the present embodiment 2 additionally provides a kind of method for bringing back to life dead catalyst mixed liquor, comprising: Xiang Ru
Water and glacial acetic acid is added in the preceding dead catalyst mixed liquor；Centrifugation, filtering, obtain solid phase；And first is added into solid phase
Pure and mild sodium methoxide, as Schiff alkali composite catalyst.
Specific ingredient and implementation process about dead catalyst mixed liquor are discussed referring to the correlation of embodiment 1, herein no longer
It repeats.
Taking the above-mentioned ideal embodiment according to the present invention as inspiration, through the above description, relevant staff is complete
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property range is not limited to the contents of the specification, it is necessary to which the technical scope thereof is determined according to the scope of the claim.
Claims (8)
1. a kind of preparation method of R- propene carbonate characterized by comprising
Esterification；
Recycle the by-product of esterification；And
The product of distilation esterification obtains the R- propene carbonate.
2. preparation method according to claim 1, which is characterized in that
Dimethyl carbonate and (R) -1,2-PD are added in reaction kettle, Schiff alkali composite catalyst is then added, heat into
The row esterification.
3. preparation method according to claim 2, which is characterized in that
The temperature of the esterification is 65-68 DEG C.
4. preparation method according to claim 1, which is characterized in that
The method of by-product of the recycling esterification includes:
Reactant after esterification is subjected to air-distillation, to steam by-product；
It is recycled by condensing and separating；And
Fixed gas enters exhaust treatment system.
5. the preparation method according to claim 4, which is characterized in that
The mode of the condensation is in such a way that level-one water cooling and level-one chilled brine combine.
6. preparation method according to claim 1, which is characterized in that
The product of esterification is added in vacuum distillation kettle and is evaporated under reduced pressure, the propene carbonate is obtained；And
The raffinate being evaporated under reduced pressure in kettle is dead catalyst mixed liquor.
7. preparation method according to claim 6, which is characterized in that
The preparation method further include: bring back to life dead catalyst mixed liquor；
It is described bring back to life dead catalyst mixed liquor method include:
Water and glacial acetic acid are added into dead catalyst mixed liquor；
Centrifugation, filtering, obtain solid phase,
Methanol and sodium methoxide, as Schiff alkali composite catalyst are added into solid phase.
8. a kind of method for bringing back to life dead catalyst mixed liquor characterized by comprising
Water and glacial acetic acid are added into dead catalyst mixed liquor as claimed in claim 6；
Centrifugation, filtering, obtain solid phase；And
Methanol and sodium methoxide, as Schiff alkali composite catalyst are added into solid phase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811349047.3A CN109400475A (en) | 2018-11-13 | 2018-11-13 | A kind of preparation method of R- propene carbonate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811349047.3A CN109400475A (en) | 2018-11-13 | 2018-11-13 | A kind of preparation method of R- propene carbonate |
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| Publication Number | Publication Date |
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| CN109400475A true CN109400475A (en) | 2019-03-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201811349047.3A Pending CN109400475A (en) | 2018-11-13 | 2018-11-13 | A kind of preparation method of R- propene carbonate |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559180A (en) * | 1982-11-26 | 1985-12-17 | Bp Chemicals Limited | Transesterification of esters |
| CN1416953A (en) * | 2002-12-06 | 2003-05-14 | 大连理工大学 | Double-function catalyst for synthesizing cyclic carbonate and methyl carbonate |
| CN104447675A (en) * | 2014-11-17 | 2015-03-25 | 潍坊汇韬化工有限公司 | Solvent-free R-propylene carbonate and production process thereof |
| CN104725423A (en) * | 2013-12-18 | 2015-06-24 | 山东新时代药业有限公司 | Tenofovir disoproxil fumarate synthesis method |
-
2018
- 2018-11-13 CN CN201811349047.3A patent/CN109400475A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559180A (en) * | 1982-11-26 | 1985-12-17 | Bp Chemicals Limited | Transesterification of esters |
| CN1416953A (en) * | 2002-12-06 | 2003-05-14 | 大连理工大学 | Double-function catalyst for synthesizing cyclic carbonate and methyl carbonate |
| CN104725423A (en) * | 2013-12-18 | 2015-06-24 | 山东新时代药业有限公司 | Tenofovir disoproxil fumarate synthesis method |
| CN104447675A (en) * | 2014-11-17 | 2015-03-25 | 潍坊汇韬化工有限公司 | Solvent-free R-propylene carbonate and production process thereof |
Non-Patent Citations (4)
| Title |
|---|
| MAURIZIO SELVA ET AL.: "Carbonate phosphonium salts as catalysts for the transesterification of dialkyl carbonates with diols. The competition between cyclic carbonates and linear dicarbonate products", 《ORG. BIOMOL. CHEM.》 * |
| NICOLAS S. SUVEGES SELVA ET AL.: "Continuous-Flow Synthesis of (R)-Propylene Carbonate: An Important Intermediate in the Synthesis of Tenofovir", 《EUR. J. ORG. CHEM.》 * |
| 夏剑辉等: "甲醇钠催化合成(R)-碳酸丙烯酯", 《化学世界》 * |
| 张龙等: "《绿色化学（第二版）》", 31 August 2014, 华中科技大学出版社 * |
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Application publication date: 20190301 |