CN112409296A - Preparation method of propylene oxide - Google Patents
Preparation method of propylene oxide Download PDFInfo
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- CN112409296A CN112409296A CN202011359739.3A CN202011359739A CN112409296A CN 112409296 A CN112409296 A CN 112409296A CN 202011359739 A CN202011359739 A CN 202011359739A CN 112409296 A CN112409296 A CN 112409296A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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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
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Abstract
The invention provides a preparation method of propylene oxide, which is characterized in that a material after primary epoxidation reaction is concentrated by tert-butyl hydroperoxide, unreacted propylene with low boiling point and PO are separated by rectification, and then the concentration of TBHP in a reaction system is increased by rectification, specifically, the concentration of TBHP and a catalyst is increased by reducing TBA, so that the epoxidation reaction rate is increased; most importantly, the acetone and water generated in the primary epoxidation reaction can be separated and then subjected to secondary epoxidation reaction, so that the reaction rate and the PO selectivity are improved.
Description
Technical Field
The invention belongs to the technical field of propylene oxide, and particularly relates to a preparation method of propylene oxide.
Background
Propylene oxide is a very important organic compound starting material, second only to polypropylene and acrylonitrile, the third largest propylene-based derivative. The propylene oxide is mainly used for producing polyether polyol, propylene glycol, various nonionic surfactants and the like, wherein the polyether polyol is an important raw material for producing polyurethane foam, heat insulation materials, elastomers, adhesives, coatings and the like, and the various nonionic surfactants are widely applied to industries such as petroleum, chemical engineering, pesticides, textile, daily chemicals and the like. Meanwhile, propylene oxide is also an important basic chemical raw material.
In the prior art, ethylbenzene, isobutane or cumene is usually used for oxidation to prepare organic peroxides such as ethylbenzene hydroperoxide (EBHP), tert-butyl hydroperoxide (TBHP) or Cumene Hydroperoxide (CHP), and the organic peroxides are subjected to epoxidation reaction with propylene under the action of a catalyst to generate propylene oxide. In the case of t-butyl hydroperoxide, the reaction is as
In the epoxidation reaction of propylene and TBHP, excessive propylene is usually required, and the conversion rate of TBHP is more than 99%, on one hand, based on the process requirement, the conversion rate of TBHP is high, and more PO is obtained; on the other hand, based on the process safety requirement, if the TBHP remains a lot in the reaction process, the TBHP content in the post-treated waste liquid will be increased, and potential safety hazards will be brought to incineration treatment and the like.
Therefore, how to increase the reaction rate of propylene oxide in the preparation process of propylene oxide and further increase the selectivity of PO is an urgent problem to be solved in the field.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a preparation method of propylene oxide, which can improve the TBHP concentration in a reaction system through the arrangement of a rectifying tower, and can improve the TBHP reaction rate and the selectivity of the propylene oxide.
The purpose of the invention is realized by the following technical scheme:
a preparation method of propylene oxide comprises the steps of preparing raw materials of propylene oxide, tert-butyl hydroperoxide, tert-butyl alcohol and a catalyst;
the preparation method comprises the step of carrying out concentration treatment on the tertiary butyl hydroperoxide on the material after the primary epoxidation reaction.
According to the present invention, the primary epoxidation reaction is an epoxidation reaction in which propylene, t-butyl hydroperoxide, t-butanol and a catalyst are mixed, the reaction process is a fast reaction stage, and the conversion rate of t-butyl hydroperoxide during the primary epoxidation reaction can reach about 85-95%.
According to the invention, in the primary epoxidation reaction process, the molar ratio of propylene to tert-butyl hydroperoxide is 1.6-3.0: 1; t-butanol is a solvent during the primary epoxidation reaction which may provide a reaction medium for the reaction.
According to the present invention, the catalyst is a catalyst for producing propylene oxide using t-butyl hydroperoxide, which is conventional in the art, and is, for example, a molybdenum-containing catalyst (illustratively, a catalyst in which molybdenum is contained in an amount of 5 to 30 wt%, for example, 8 to 15 wt%), specifically, for example, a dialkyldiol compound of molybdenum (e.g., molybdenum glycol), a molybdenum peroxide compound, or the like. Illustratively, the addition amount of the catalyst is 100-1000 ppm.
According to the invention, the temperature of the primary epoxidation reaction is 120-140 ℃, the residence time of the primary epoxidation reaction is 0.5-0.8 hr, and the pressure of the primary epoxidation reaction is 3.2-4.0 MPa.
According to the present invention, the primary epoxidation reaction may be carried out in an isothermal manner or in a stepwise manner.
According to the present invention, the material after the primary epoxidation reaction contains unreacted propylene, t-butyl hydroperoxide and t-butyl alcohol, propylene oxide produced by the reaction and a small amount of impurity components (such as water, acetone, etc.).
According to the invention, the material after the primary epoxidation reaction contains 10-25 wt% of unreacted propylene, 1.5-5.0 wt% of tert-butyl hydroperoxide, 30-60 wt% of tert-butyl alcohol, 10-20 wt% of propylene oxide and 2-4 wt% of impurity components (such as 0.01-0.40 wt% of water, 0.1-0.4 wt% of acetone and the like).
According to the invention, before the concentration treatment step of TBHP, the material after the primary epoxidation reaction can be subjected to a propylene separation treatment step and a propylene oxide separation treatment step; the separation treatment step of the propylene aims to separate unreacted propylene, so that materials are recycled, the process cost is saved, and the unreacted propylene is inevitably separated from a reaction system when the propylene oxide is separated because the boiling point of the propylene is lower than that of the propylene oxide; the separation treatment step of the propylene oxide aims to avoid the series of side reactions such as polymerization, ring opening and the like of the propylene oxide which is generated in the subsequent reaction process.
According to the invention, the propylene separation step and the propylene oxide separation step are carried out using separation steps customary in the art, for example in a rectification column or in a flash column.
According to the present invention, the propylene separation treatment step and the propylene oxide separation treatment step may be carried out in the same rectification column; or in two rectifying towers, namely, the rectifying tower is firstly used for rectifying and separating propylene, and then the rectifying tower is used for rectifying and separating propylene oxide.
When the propylene separation treatment step and the propylene oxide separation treatment step are carried out in the same rectifying tower, the operating conditions of the rectifying tower are that the temperature of a tower kettle of the rectifying tower is 95-105 ℃, and preferably 100 ℃; the top pressure of the rectifying tower is 1.9-2.2 MPa, the reflux ratio is 1.6-1.8, and a low-temperature refrigerant of-20 ℃ is used.
When the propylene separation treatment step and the propylene oxide separation treatment step are carried out in two rectifying towers, the operating conditions of the rectifying towers for separating propylene are that the temperature of a tower kettle of the rectifying tower is 100-110 ℃, the pressure of the tower top of the rectifying tower is 0.6-0.7 MPa, and the reflux ratio is 1-1.2; the operating conditions of the rectifying tower for separating the epoxypropane are that the temperature of the bottom of the rectifying tower is 100-110 ℃, the top pressure of the rectifying tower is 0.15-0.20 MPa, and the reflux ratio is 2.5-2.0.
According to the invention, the material after the primary epoxidation reaction from which propene and propene oxide are separated is subjected to a TBHP concentration treatment step.
According to the invention, the material after the primary epoxidation reaction of propylene and propylene oxide is separated contains 2-7 wt% of tert-butyl hydroperoxide, 70-90 wt% of tert-butyl alcohol and 3-5 wt% of impurity components (such as 0.05-0.50 wt% of water, 0.15-0.50 wt% of acetone and the like).
According to the invention, the concentration treatment step of the tert-butyl hydroperoxide is carried out in a rectifying tower, and the operating conditions of the rectifying tower are that the temperature of a tower kettle of the rectifying tower is 60-80 ℃, the pressure of a tower top of the rectifying tower is 0.05-0.08 MPa, and the reflux ratio is 0.8-1.5.
According to the invention, after the concentration treatment step of the tert-butyl hydroperoxide, a gas phase component containing tert-butyl alcohol and a small amount of impurities such as acetone and water can be obtained, and simultaneously, the concentrated tert-butyl hydroperoxide and tert-butyl alcohol and a liquid phase component with less impurity content are obtained.
According to the invention, the concentration treatment step of the tert-butyl hydroperoxide can realize the purpose of improving the concentration of the tert-butyl hydroperoxide, and simultaneously, the solvent acetone which can obviously reduce the epoxidation reaction rate is removed, and the content of water which has a destructive effect on the product propylene oxide is greatly reduced.
According to the invention, in the concentrated liquid phase components of tert-butyl hydroperoxide, tert-butyl alcohol and a small amount of impurities, the mass percentage of tert-butyl hydroperoxide is 5.0-10.0 wt%, the mass percentage of acetone is 0.01-0.2 wt%, and the mass percentage of water is 0.01-0.2 wt%.
According to the invention, after the concentration treatment step of TBHP is carried out on the material after the primary epoxidation reaction, a secondary epoxidation reaction can be carried out, wherein the secondary epoxidation reaction can adopt an isothermal reaction or an adiabatic reaction, the reaction temperature is 130-135 ℃, and the reaction pressure is 3-4 MPa.
According to the invention, propylene can be added in the secondary epoxidation reaction process, and the molar ratio of the added amount of the propylene to tert-butyl hydroperoxide in the reaction system is 3.0-10.0: 1, preferably 5.0-6.0: 1; the residence time of the secondary epoxidation reaction is 30-60 min.
According to the invention, after the concentration process of the tert-butyl hydroperoxide, the concentration of the tert-butyl hydroperoxide in the reaction system is improved, the concentration of the catalyst is improved, and the acetone is removed, so that the epoxidation reaction rate of propylene and the tert-butyl hydroperoxide is high, the PO selectivity is good, the impurities are reduced, and the total conversion rate of the tert-butyl hydroperoxide reaches more than 99%.
According to the invention, the method comprises the following steps:
1) mixing propylene, tert-butyl hydroperoxide, tert-butyl alcohol and a catalyst to carry out primary epoxidation reaction;
2) rectifying the product after the primary epoxidation reaction to separate propylene and propylene oxide;
3) concentrating the product obtained after the primary epoxidation reaction of propylene and propylene oxide is separated out to obtain a tower bottom liquid phase component with the tert-butyl hydroperoxide content of 5-10 wt%;
4) and 3) mixing propylene with the tower bottom liquid phase component with the tert-butyl hydroperoxide content of 5-10 wt% obtained in the step 3), and performing a secondary epoxidation reaction to obtain the propylene oxide.
The invention has the beneficial effects that:
the invention provides a preparation method of propylene oxide, which is characterized in that a material after primary epoxidation reaction is concentrated by tert-butyl hydroperoxide, unreacted propylene with low boiling point and PO are separated by rectification, and then the concentration of TBHP in a reaction system is increased by rectification, specifically, the concentration of TBHP and a catalyst is increased by reducing TBA, so that the epoxidation reaction rate is increased; most importantly, the acetone and water generated in the primary epoxidation reaction can be separated and then subjected to secondary epoxidation reaction, so that the reaction rate and the PO selectivity are improved.
Detailed Description
The preparation method of the present invention will be described in further detail with reference to specific examples. It is to be understood that the following examples are only illustrative and explanatory of the present invention and should not be construed as limiting the scope of the present invention. All the technologies realized based on the above-mentioned contents of the present invention are covered in the protection scope of the present invention.
The experimental methods used in the following examples are all conventional methods unless otherwise specified; reagents, materials and the like used in the following examples are commercially available unless otherwise specified.
Comparative example 1
160.08g of TBHP/TBA solution (the content of TBHP is 38.39 wt%) is added into a 1L reaction kettle, 0.70g of ethylene-molybdenum glycol catalyst (the content of Mo is 8.90 wt%) is added, the mixture is stirred and mixed uniformly, then a kettle cover is sealed, 79.00g of propylene is added, the temperature is raised to 125 ℃, and the reaction is carried out for 40 min. A sample was taken and analyzed to find that the TBHP content was 3.64 wt%, the PO content was 13.03 wt%, the propylene content was 23.50 wt%, the acetone content was 0.32 wt%, and the water content was 0.31 wt%.
The reaction product was transferred to a rectification column at a column bottom temperature of 100 deg.C, a column top temperature of-20 deg.C, a reflux ratio of 1.6, and a column top pressure of 1.9MPa, to distill off 87.40g of the propylene and PO mixture in the product. 152.20g of heavy components in the bottom of the primary epoxidation product tower are obtained in the tower, wherein the content of TBHP is 5.74 wt%, the content of acetone is 0.39 wt%, and the content of water is 0.38 wt%.
120.00g of heavy components at the bottom of the tower, which are separated by rectification, of the primary epoxidation product are added into a 1L stainless steel reaction kettle, 19.00g of propylene is added into the reaction kettle, the temperature is increased by heating, the reaction temperature is controlled to be kept at 134 ℃, the reaction is carried out for 34 minutes, the TBHP content is 0.35 percent by sampling analysis, and the PO content is 2.55 percent.
The conversion of the secondary epoxidation TBHP was calculated to be 92.9% and the PO selectivity was calculated to be 86.0%.
Example 1
150.00g of the heavy component at the bottom of the primary epoxidation product in the comparative example 1 is added into a rectifying tower, and the concentration is carried out by adopting a reduced pressure rectification mode, wherein the temperature of a tower bottom is 64.6 ℃, the pressure of a tower top is 0.06MPa, and the reflux ratio is 1. The TBA and part of impurities extracted from the top of the column amounted to 34.8g, with the acetone content of 0.88 wt% and the water content of 0.98 wt%. 115.0g of heavy components in the column bottom are extracted from the column bottom, wherein the TBHP content is 7.46 wt%, the acetone content is 0.017 wt%, and the water content is 0.20 wt%.
115.00g of the tower bottom components are added into a 1L stainless steel reaction kettle, 25.12g of propylene is added, the temperature is raised by heating to control the reaction temperature to be 134 ℃, the reaction is carried out for 34 minutes, the TBHP content is 0.23 wt% by sampling analysis, and the PO content is 3.59 wt%.
The conversion of the secondary epoxidation TBHP was calculated to be 96.2% and the PO selectivity was calculated to be 94.5%.
Further, as can be seen from example 1 and comparative example 1, the conversion of TBHP of example 1 was higher over the same time period, indicating a faster rate of reaction.
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A preparation method of propylene oxide comprises the steps of preparing raw materials of propylene oxide, tert-butyl hydroperoxide, tert-butyl alcohol and a catalyst;
the preparation method comprises the step of carrying out concentration treatment on the tertiary butyl hydroperoxide on the material after the primary epoxidation reaction.
2. The process according to claim 1, wherein the primary epoxidation reaction is an epoxidation reaction carried out after mixing propylene, t-butyl hydroperoxide, t-butanol and a catalyst.
Preferably, the temperature of the primary epoxidation reaction is 120-140 ℃, the residence time of the primary epoxidation reaction is 0.5-0.8 hr, and the pressure of the primary epoxidation reaction is 3.2-4.0 MPa.
Preferably, the primary epoxidation reaction may be carried out in an isothermal manner or in a stepwise temperature rise manner.
3. The process according to claim 1 or 2, wherein the material after the primary epoxidation reaction contains unreacted propylene, t-butyl hydroperoxide and t-butanol, and propylene oxide produced by the reaction and a small amount of impurity components (such as water, acetone, etc.).
Preferably, the material after the primary epoxidation reaction contains 10 to 25 wt% of unreacted propylene, 1.5 to 5 wt% of tert-butyl hydroperoxide, 30 to 60 wt% of tert-butyl alcohol, 10 to 20 wt% of propylene oxide, and 2 to 4 wt% of impurity components (such as 0.01 to 0.40 wt% of water, 0.1 to 0.4 wt% of acetone, etc.).
4. A process according to any one of claims 1 to 3, wherein the feed after the primary epoxidation reaction is subjected to a separation treatment of propylene and a separation treatment of propylene oxide before the concentration treatment of TBHP.
5. The process according to claim 4, wherein the propylene separation treatment step and the propylene oxide separation treatment step are carried out in the same rectification column; or in two rectifying towers, namely, the rectifying tower is firstly used for rectifying and separating propylene, and then the rectifying tower is used for rectifying and separating propylene oxide.
Preferably, when the propylene separation treatment step and the propylene oxide separation treatment step are carried out in the same rectifying tower, the operating conditions of the rectifying tower are that the temperature of a tower kettle of the rectifying tower is 95-105 ℃, and preferably 100 ℃; the top pressure of the rectifying tower is 1.9-2.2 MPa, the reflux ratio is 1.6-1.8, and a low-temperature refrigerant of-20 ℃ is used.
Preferably, when the propylene separation treatment step and the propylene oxide separation treatment step are carried out in two rectifying towers, the operating conditions of the rectifying towers for separating propylene are that the temperature of a tower kettle of the rectifying tower is 100-110 ℃, the pressure of the tower top of the rectifying tower is 0.6-0.7 MPa, and the reflux ratio is 1-1.2; the operating conditions of the rectifying tower for separating the epoxypropane are that the temperature of the bottom of the rectifying tower is 100-110 ℃, the top pressure of the rectifying tower is 0.15-0.20 MPa, and the reflux ratio is 2.5-2.0.
6. The process according to any one of claims 1 to 5, wherein the feed after the primary epoxidation of propylene and propylene oxide is separated contains 2 to 7 wt% of t-butyl hydroperoxide, 70 to 90 wt% of t-butyl alcohol, 3 to 5 wt% of impurity components (e.g., 0.05 to 0.50 wt% of water, 0.15 to 0.50 wt% of acetone, etc.).
7. The process as claimed in any one of claims 1 to 6, wherein the concentration treatment step of t-butyl hydroperoxide is carried out in a rectifying tower operated under such conditions that the temperature of the bottom of the rectifying tower is 60 to 80 ℃, the pressure of the top of the rectifying tower is 0.05 to 0.08MPa, and the reflux ratio is 0.8 to 1.5.
8. The process as claimed in any one of claims 1 to 7, wherein the concentration treatment step of t-butyl hydroperoxide can obtain a gas phase component containing t-butyl alcohol and small amount of impurities such as acetone and water, and obtain a liquid phase component containing less impurities.
Preferably, in the concentrated liquid phase components of the tert-butyl hydroperoxide, the tert-butyl alcohol and a small amount of impurities, the mass percentage of the tert-butyl hydroperoxide is 5.0-10.0 wt%, the mass percentage of the acetone is 0.01-0.2 wt%, and the mass percentage of the water is 0.01-0.2 wt%.
9. The method according to any one of claims 1 to 8, wherein after the concentration treatment step of TBHP, the material after the primary epoxidation reaction is subjected to a secondary epoxidation reaction, wherein the secondary epoxidation reaction can be an isothermal reaction or an adiabatic reaction, the reaction temperature is 130-135 ℃, and the reaction pressure is 3-4 MPa.
Preferably, propylene can be added in the secondary epoxidation reaction process, and the molar ratio of the added propylene to tert-butyl hydroperoxide in the reaction system is 3.0-10.0: 1, preferably 5.0-6.0: 1; the residence time of the secondary epoxidation reaction is 30-60 min.
10. The method according to any one of claims 1-9, wherein the method comprises the steps of:
1) mixing propylene, tert-butyl hydroperoxide, tert-butyl alcohol and a catalyst to carry out primary epoxidation reaction;
2) rectifying the product after the primary epoxidation reaction to separate propylene and propylene oxide;
3) concentrating the product obtained after the primary epoxidation reaction of propylene and propylene oxide is separated out to obtain a tower bottom liquid phase component with the tert-butyl hydroperoxide content of 5-10 wt%;
4) and 3) mixing propylene with the tower bottom liquid phase component with the tert-butyl hydroperoxide content of 5-10 wt% obtained in the step 3), and performing a secondary epoxidation reaction to obtain the propylene oxide.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0179664A2 (en) * | 1984-10-26 | 1986-04-30 | Arco Chemical Technology, Inc. | Preparation of soluble molybdenum Catalysts for epoxidation of olefins |
| US4977285A (en) * | 1989-12-08 | 1990-12-11 | Texaco Chemical Company | Recovery of tertiary butyl hydroperoxide and tertiary butyl alcohol |
| US4992566A (en) * | 1989-08-31 | 1991-02-12 | Texaco Chemical Company | Recovery of tertiary butyl hydroperoxide and tertiary butyl alcohol |
| US5349072A (en) * | 1993-07-06 | 1994-09-20 | Texaco Chemical Company | Staged epoxidation of propylene with recycle |
| EP0710640A1 (en) * | 1994-11-01 | 1996-05-08 | Texaco Development Corporation | Recovery and purification of tertiary butyl alcohol |
| CN109890791A (en) * | 2016-10-12 | 2019-06-14 | 利安德化学技术有限公司 | The production of tert-butyl hydroperoxide solution and the method that product is consequently formed |
-
2020
- 2020-11-27 CN CN202011359739.3A patent/CN112409296B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0179664A2 (en) * | 1984-10-26 | 1986-04-30 | Arco Chemical Technology, Inc. | Preparation of soluble molybdenum Catalysts for epoxidation of olefins |
| US4992566A (en) * | 1989-08-31 | 1991-02-12 | Texaco Chemical Company | Recovery of tertiary butyl hydroperoxide and tertiary butyl alcohol |
| US4977285A (en) * | 1989-12-08 | 1990-12-11 | Texaco Chemical Company | Recovery of tertiary butyl hydroperoxide and tertiary butyl alcohol |
| US5349072A (en) * | 1993-07-06 | 1994-09-20 | Texaco Chemical Company | Staged epoxidation of propylene with recycle |
| EP0710640A1 (en) * | 1994-11-01 | 1996-05-08 | Texaco Development Corporation | Recovery and purification of tertiary butyl alcohol |
| CN109890791A (en) * | 2016-10-12 | 2019-06-14 | 利安德化学技术有限公司 | The production of tert-butyl hydroperoxide solution and the method that product is consequently formed |
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Inventor after: Ma Min Inventor after: Jun Ming Dai Inventor after: Xie Shumin Inventor after: Zhu Dequan Inventor after: Yang Can Inventor before: Ma Min Inventor before: Jun Ming Dai Inventor before: Xie Shumin Inventor before: Zhu Dequan |
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