CN112209903A - Purification method of propylene oxide - Google Patents
Purification method of propylene oxide Download PDFInfo
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- CN112209903A CN112209903A CN201910616493.4A CN201910616493A CN112209903A CN 112209903 A CN112209903 A CN 112209903A CN 201910616493 A CN201910616493 A CN 201910616493A CN 112209903 A CN112209903 A CN 112209903A
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- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
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- 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
Abstract
The invention provides a purification method of propylene oxide, which comprises the following steps: 1) carrying out extractive distillation on propylene oxide containing water, oxygen-containing impurities and hydrocarbon impurities in a rectifying tower by using an extractive distillation agent with the purity of more than or equal to 99.9 percent to obtain propylene oxide basically containing no water at the tower top and obtain an extractive distillation agent rich solution containing water and the oxygen-containing impurities at the tower bottom; 2) and (3) regenerating the extractive rectification agent rich solution containing water and oxygen-containing impurities to obtain an extractive rectification agent barren solution with the purity of more than or equal to 99.9%, and returning the extractive rectification agent barren solution with the purity of more than or equal to 99.9% to the rectification tower. Namely, the method comprises the steps of carrying out extractive rectification on propylene oxide containing oxygen-containing impurities such as water, methanol, acetone and the like and C5-C6 hydrocarbon impurities in a rectification tower by using an extractive rectification agent with the purity of more than 99.9%, and carrying out primary extractive rectification at a relatively low temperature to obtain the propylene oxide with the water content of less than 20 ppm.
Description
Technical Field
The invention belongs to the technical field of propylene oxide, and particularly relates to a method for purifying propylene oxide.
Background
Propylene Oxide (PO) plays an important role in chemical synthesis, is mainly used for producing polyether polyol and Propylene glycol, wherein the polyether polyol is a necessary raw material for synthesizing polyurethane, is widely applied to industries such as heat insulation materials, furniture, elastomers, adhesives, coatings and the like, and has large quantity of derived downstream products and wide application.
PO is typically formed by the reaction of propylene with an oxidizing agent in the presence of a catalyst. It is commercially produced by reacting propylene with an organic hydroperoxide (e.g. ethylbenzene hydroperoxide, cumene hydroperoxide or tert-butyl hydroperoxide) in the presence of a dissolved molybdenum catalyst or a heterogeneous catalyst of titania on silica. In addition, PO can also be prepared by reacting propylene with hydrogen peroxide in the presence of a titanium silicate catalyst. The PO prepared by these processes usually contains a small amount of water, hydrocarbon (usually C)4-C6Alkanes and alkenes) and oxygen-containing by-products (e.g., methanol, acetone, methyl formate, and aldehydes (acetaldehyde and propionaldehyde), etc.), and propylene oxide containing such impurities is referred to as crude propylene oxide. For most PO applications, especially polymer grade PO, high PO purity is required. In order to obtain propylene oxide satisfying the polymerization requirements, it is necessary to separate and remove impurities contained in the crude propylene oxide and purify the propylene oxide content to 99.95 wt% or more.
Because the relative volatility of methyl formate and propylene oxide is close to 1, the boiling points of acetaldehyde, acetone and propylene oxide are close, and propylene oxide, water, methanol and the like all form azeotrope and the like, the common rectification method is difficult to complete the purification of propylene oxide. The removal of water from crude propylene oxide is of utmost importance in relation to other impurities, since propylene oxide undergoes hydrolysis in the presence of water to form Propylene Glycol (PG), and the water content of polymer grade propylene oxide products is very critical, and is usually required to be less than 50 ppm. Therefore, the PO must be dewatered to reduce its moisture content to a certain level or even to a moisture free level.
Methods of extractive distillation are disclosed in the prior art, for example, U.S. Pat. No. 4, 3578568 discloses a method for separating propylene oxide from water, methanol, acetone and acetaldehyde by extractive distillation using ethylene glycol, propylene glycol, ethylene glycol monomethyl ether or diethylene glycol monomethyl ether as extraction solvent. U.S. Pat. No. 5,5354430 discloses a method for purifying crude PO by fractionation, wherein diol is used as extractant for extractive distillation to remove oxygen-containing impurities such as methanol and aldehyde, and C is added8The alkane is extracted, rectified and deparaffinized, and the extraction and rectification agent is recycled after regeneration.
Unfortunately, when PO is refined using glycol as the extractive distillation agent, water and the extractive distillation agent react with PO under normal extractive distillation conditions, resulting in a decrease in PO yield and loss of the extractive distillation agent.
In order to obtain PO with low water content and avoid the reaction of water, extractive rectification agent and PO during extractive rectification, US5354431 discloses a method for preparing purified PO by multistage extractive rectification, wherein crude PO is subjected to glycol extractive rectification at a high kettle temperature to remove most of water, then subjected to alkane extractive rectification to remove oxygen-containing impurities and hydrocarbon impurities, and then subjected to extractive rectification with glycol at a low kettle temperature to obtain pure PO substantially free of water. The regeneration operation of the triethylene glycol (TEG) extraction rectification agent is completed by vacuum rectification. The process flow is complex and needs two times of glycol solvent extraction and rectification operations.
In the above process schemes, either the purified impurity content is not suitable for practical application, or pure PO substantially free of moisture can be obtained, but the process is complicated and critical, for example, two glycol extractions and distillations are required. Therefore, there is still a strong need for a simple and efficient purification process to obtain pure PO with a desired content of substantially moisture-free impurities.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a method for purifying propylene oxide. The inventor finds that in the existing crude PO rectification dehydration technology, the extraction rectification dehydration effect is poor due to the fact that the fresh or regenerated extraction rectification dehydrating agent is high in moisture content; if the PO is refined by using the extractive distillation agent with extremely low water content, almost all impurity water can be removed by extractive distillation at a lower tower kettle temperature through one-step extractive distillation operation to obtain PO containing substantially no water, and the reaction of water with the extractive agent and the PO under the conventional extractive distillation operation condition is avoided, thereby completing the invention.
The purpose of the invention is realized by the following technical scheme:
a process for the purification of propylene oxide, the process comprising:
1) carrying out extractive distillation on propylene oxide containing water, oxygen-containing impurities and hydrocarbon impurities in a rectifying tower by using an extractive distillation agent with the purity of more than or equal to 99.9 percent to obtain propylene oxide basically containing no water at the tower top and obtain an extractive distillation agent rich solution containing water and the oxygen-containing impurities at the tower bottom;
2) and (3) regenerating the extractive rectification agent rich solution containing water and oxygen-containing impurities to obtain an extractive rectification agent barren solution with the purity of more than or equal to 99.9%, and returning the extractive rectification agent barren solution with the purity of more than or equal to 99.9% to the rectification tower.
In the present invention, the propylene oxide containing moisture, oxygen-containing impurities and hydrocarbon impurities is also referred to as crude PO.
According to the invention, in step 1), the concentration of the extractive distillation agent is preferably greater than or equal to 99.95%, and more preferably greater than or equal to 99.99%.
According to the invention, in the step 1), the extractive distillation agent is selected from one of ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropyl ethylene glycol, ethylene glycol monomethyl ether, glycerol, propylene glycol, butanediol and hexanediol or a mixture thereof.
According to the invention, in step 1), the oxygen-containing impurities are selected, for example, from one or more of methanol, acetaldehyde, acetone, methyl formate, propionaldehyde and the like.
According to the invention, in step 1), the hydrocarbon impurities are for example selected from one or more of C5 hydrocarbons, C6 hydrocarbons and the like.
According to the invention, in step 1), the weight ratio of the extractive rectification agent to the crude PO is 1:2 to 7, for example 1:2, 1:3, 1:4, 1:5, 1:6, 1: 7.
According to the invention, in step 1), the operating temperature of the extraction and rectification column is 80-110 ℃ (for example, 80 ℃, 85 ℃, 90 ℃, 95 ℃, 100 ℃, 105 ℃ or 110 ℃); the temperature at the top of the column is 35-80 deg.C (exemplary, 35 deg.C, 40 deg.C, 45 deg.C, 50 deg.C, 55 deg.C, 60 deg.C, 65 deg.C, 70 deg.C, 75 deg.C or 80 deg.C).
According to the present invention, in step 1), the propylene oxide containing moisture, oxygen-containing impurities and hydrocarbon impurities contains moisture in an amount of about 0.01 to 2.0 wt%, oxygen-containing impurities in an amount of 0.01 to 2.0 wt% and hydrocarbon impurities in an amount of 0.01 to 2.0 wt%.
According to the present invention, in the substantially moisture-free propylene oxide in the step 1), the content of moisture is 20ppm or less.
According to the invention, in the step 2), fresh extractive distillation agent can be supplemented as required, the fresh extractive distillation agent and the extractive distillation agent rich solution containing water and oxygen-containing impurities are subjected to regeneration treatment to obtain extractive distillation agent barren solution with purity of 99.9% or more, and the extractive distillation agent barren solution with purity of 99.9% or more is returned to the distillation tower. Wherein, the fresh extractive distillation agent is mainly used for supplementing the loss of the extractive distillation agent.
Preferably, in step 2), an extractive rectification agent barren solution with a purity of 99.95% or more, and further 99.99% is obtained, and the barren solution is returned to the rectification column.
According to the invention, in step 2), the regeneration method comprises one of distillation, stripping (such as azeotropic agent stripping), cold finger method (Coldfinger), or their combination; preferably entrainer stripping. The entrainer in the entrainer stripping is selected from one or more of benzene, toluene, n-heptane, isooctane, isobutane, pentane, hexane, isobutene and the like.
Wherein the stripping is a unit operation for recovering absorbed solutes and separating the absorbent from the solutes to obtain regeneration. Steam stripping is a physical process, which adopts a gas medium to destroy the original gas-liquid two-phase equilibrium and establish a new gas-liquid equilibrium state, so that a certain component in the solution is desorbed due to the reduction of partial pressure, thereby achieving the purpose of separating substances. Entrainer stripping means that stripping is carried out using as stripping substance a substance which forms an azeotrope with water.
According to the invention, in step 2), the water content of the extractive distillation poor solution after the regeneration treatment is less than or equal to 50ppm, preferably less than or equal to 20 ppm.
The invention has the beneficial effects that:
the invention provides a method for purifying propylene oxide, which comprises the steps of carrying out extractive rectification on the propylene oxide containing oxygen-containing impurities such as moisture, methanol, acetone and the like and C5-C6 hydrocarbon impurities in a rectification tower by using an extractive rectification agent with the purity of more than 99.9 percent, and obtaining the propylene oxide with the moisture of less than 20ppm by carrying out primary extractive rectification at a lower tower bottom temperature; and regenerating the extractive rectification agent rich solution obtained at the bottom of the tower to obtain an extractive rectification agent barren solution with the purity of more than 99.9%, and returning the extractive rectification agent with the purity of more than 99.9% to the extractive rectification tower. The method can efficiently realize the purification of the propylene oxide, avoid the water content from being mixed in the propylene oxide, and increase the removal rate of the impurities such as acetone, methanol and the like.
Drawings
FIG. 1 is a process flow diagram of propylene oxide purification as described in example 1 of the present invention.
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.
Example 1
Fig. 1 is a process flow diagram of propylene oxide purification according to example 1 of the present invention, as shown in fig. 1, crude propylene oxide 1 (containing water, oxides such as methanol, acetaldehyde, acetone, methyl formate, and the like, and C5-C6 hydrocarbons) enters from the lower part of an extractive distillation column 3 and contacts with an extractive distillation agent (purity is greater than or equal to 99.9%) entering from the upper part of the distillation column 3, dehydrated propylene oxide 4 is obtained at the top of the column, and the dehydrated propylene oxide 4 is subjected to the next refining treatment (not shown in fig. 1); the aqueous extractive distillation agent 5 (extractive distillation agent rich liquid) and the supplemented fresh extractive distillation agent 15 at the bottom of the extractive distillation tower 3 are sent to a regeneration tower 6 for distillation; the dehydration extraction rectifying agent 8 discharged from the bottom of the regeneration tower 6 enters a stripping tower 17 from the top, a recovered and reused stripped substance 23 or a fresh stripped substance 20 discharged from the top of the regeneration tower 6 after condensation, phase separation and other treatments is subjected to combined water removal by a stripped substance dehydration adsorption tower 22 and then is heated by a heater 19 to form a high-temperature stripped gas 11, the high-temperature stripped gas 11 enters from the bottom of the stripping tower 17, and the stripped gas 14 carrying water and other impurities discharged from the top of the stripping tower 17 enters the regeneration tower 6 from the lower part; the steam stripping substance 7 carrying moisture obtained at the top of the regeneration tower 6 is cooled by a cooler 16 and then enters a buffer tank 9 for phase separation; non-condensable gas 10 at the top of the buffer tank 9 is sent to other treatment units, the condensate is divided into two phases in the buffer tank 9, a bottom water phase 13 is discharged to other treatment processes, the upper part of the buffer tank is steam stripping condensate, part of the steam stripping condensate 12 flows back to the regeneration tower 6, part of the steam stripping condensate 18 is cooled by a cooler 21 and then used as steam stripping material 23 for recovery, and the steam stripping material 23 for recovery enters a steam stripping material dehydration adsorption tower 22 to remove combined water and then enters a heater 19 to be heated into high-temperature steam stripping gas 11 and then returns to the steam stripping tower 17; the low-water-content extractant (extractive rectification agent barren solution) 2 obtained from the tower bottom of the stripping tower 17 returns to the extractive rectification tower for reuse.
After the extractive rectification agent rich solution (and fresh extractive rectification agent) is regenerated, the moisture content is lower than 20ppm, and the extractive rectification agent with the concentration of more than 99.9% is obtained; when the method is used for dehydrating the crude PO, the PO with low water content of less than 20ppm can be obtained at one time, and the removal rate of oxygen-containing impurities such as methanol, acetone and the like in the crude PO is improved.
Example 2
50 ℃ crude propylene oxide (98.85 percent of propylene oxide, 1896 percent of water, 678 percent of acetaldehyde, 800 percent of methanol, 6700 percent of methyl formate, 350 percent of acetone and 1400 percent of pentane and hexane) 1450kg/hr enters an extraction and rectification tower from a 40 tower plate, the total 85 tower plates of the extraction and rectification tower, a triethylene glycol extractant (with the purity of 99.99 percent) at 40 ℃ enters the extraction and rectification tower from a 25 tower plate, the tower pressure is 0.17MPa, the tower bottom temperature is 95 ℃, the tower top temperature is 40 ℃, the reflux ratio is 1, and a PO component with partial impurities removed is obtained at the tower top 1444kg/hr, wherein the PO content is 99.2 percent, the water is 4 percent, the acetaldehyde is 350 percent, the methanol is 20 percent, the methyl formate is 6710 percent, and the pentane and hexane content is 1410 percent. The aqueous triethylene glycol extractive rectification agent (containing 0.76% of water) is discharged from the bottom of the extractive rectification tower and enters a regeneration tower, and the temperature of the tower bottom of the regeneration tower is 195 ℃ and the pressure is 103 kPa. The extractive rectification agent with low water content from the bottom of the regeneration tower enters a stripping tower from the upper part, and 55kg/hr of isooctane gas with the temperature of 230 ℃ is introduced into the lower part of the stripping tower. The method comprises the following steps of enabling isooctane gas containing water from the top of a stripping tower to enter from the lower part of a regeneration tower, enabling isooctane carrying impurities such as water to exit from the top of the regeneration tower, cooling the isooctane gas to enter a buffer tank for phase splitting, enabling non-condensable gas at the top of the buffer tank to be processed in other procedures, enabling water phase exiting from the bottom of the buffer tank to be discharged out of a system, enabling an isooctane liquid phase at the upper part of the buffer tank to be cooled by a cooler, enabling a solid adsorbent dehydration adsorption tower to remove combined water in the isooctane liquid phase, then enabling the isooctane liquid phase to enter a heater for heating, and. The dehydrated extraction rectification agent triethylene glycol (the content of triethylene glycol is 99.99 wt%) is discharged from the bottom of the stripping tower and returned to the extraction rectification tower for reuse.
Example 3
The feeding and the equipment are the same as the example 2, except that the purity of the reclaimed barren solution of the extractive rectification agent is 99.9 percent, and PO with partial impurities removed is obtained at the top of the extractive rectification tower, wherein the water content is 18 ppm.
Comparative example 1
1450kg/hr of 50 ℃ crude propylene oxide (98.85 percent of propylene oxide, 1896 percent of water, 678 percent of acetaldehyde, 800 percent of methanol, 6700 percent of methyl formate, 350 percent of acetone and 1400 percent of pentane and hexane) enters an extractive distillation tower from a 40 tower plate, the total 85 tower plates of the extractive distillation tower, 360kg/hr of 40 ℃ triethylene glycol extractant (containing 1.0 percent of water and 98.7 percent of triethylene glycol) enters the extractive distillation tower from a 25 tower plate, the tower pressure is 0.24MPa, the tower bottom temperature is 176 ℃, the tower top temperature is 40 ℃, the reflux ratio is 1, 1440kg/hr of PO component with partial impurities removed is obtained at the tower top, wherein the PO content is 99.0 percent, the water content is 226 percent, the acetaldehyde content is 450 percent, 460 percent of methanol, the methyl formate is 6700 percent, the acetone content is 10 percent, and the pentane and hexane content is 1390 percent. The water-containing triethylene glycol extractive rectification agent is extracted from the bottom of the extractive rectification tower, wherein the water content is 1.65%, the methanol content is 960ppm, the acetone content is 530ppm, the water-containing triethylene glycol extractive rectification agent is regenerated through reduced pressure distillation, the regeneration pressure is 3kPa, and the temperature of the bottom of the tower is 176 ℃. And regenerating to obtain the low-water-content extractive distillation agent, wherein the water content is 1.0 percent, the triethylene glycol content is 98.7 percent, and the low-water-content extractive distillation agent is returned to the extractive distillation tower for reuse.
Compared with the method for extracting and rectifying the crude PO by using the extractive rectifying agent with low water content, the method for extracting and rectifying the PO has the advantages that the removal rate of water, acetone, methanol and the like in the crude PO treated in the examples 2 and 3 is high, and the PO yield is high.
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 method for purifying propylene oxide, wherein the method comprises:
1) carrying out extractive distillation on propylene oxide containing water, oxygen-containing impurities and hydrocarbon impurities in a rectifying tower by using an extractive distillation agent with the purity of more than or equal to 99.9 percent to obtain propylene oxide basically containing no water at the tower top and obtain an extractive distillation agent rich solution containing water and the oxygen-containing impurities at the tower bottom;
2) and (3) regenerating the extractive rectification agent rich solution containing water and oxygen-containing impurities to obtain an extractive rectification agent barren solution with the purity of more than or equal to 99.9%, and returning the extractive rectification agent barren solution with the purity of more than or equal to 99.9% to the rectification tower.
2. The method according to claim 1, wherein in step 1), the concentration of the extractive distillation agent is preferably greater than or equal to 99.95%, and further greater than or equal to 99.99%.
Preferably, in step 1), the extractive distillation agent is selected from one of ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropyl ethylene glycol, ethylene glycol monomethyl ether, glycerol, propylene glycol, butanediol, hexanediol, or a mixture thereof.
3. The process of claim 1 or 2, wherein in step 1), the oxygen-containing impurities are selected from one or more of methanol, acetaldehyde, acetone, methyl formate, propionaldehyde.
Preferably, in step 1), the hydrocarbon impurities are selected from one or more of C5 hydrocarbons, C6 hydrocarbons.
4. The process of any one of claims 1-3, wherein in step 1), the weight ratio of the extractive distillation agent to propylene oxide containing moisture, oxygen-containing impurities, and hydrocarbon impurities is from 1:2 to 7.
5. The method as claimed in any one of claims 1 to 4, wherein, in the step 1), the operation temperature of the extraction rectification tower is 80-110 ℃; the temperature at the top of the tower is 35-80 ℃.
6. The process according to any one of claims 1 to 5, wherein in step 1), the propylene oxide containing moisture, oxygen-containing impurities and hydrocarbon impurities contains 0.01 to 2.0 wt% of moisture, 0.01 to 2.0 wt% of oxygen-containing impurities and 0.01 to 2.0 wt% of hydrocarbon impurities.
7. The process according to any one of claims 1 to 6, wherein the content of moisture in the substantially moisture-free propylene oxide in step 1) is 20ppm or less.
8. The method according to any one of claims 1 to 7, wherein in the step 2), fresh extractive distillation agent is supplemented as required, the fresh extractive distillation agent and the extractive distillation agent rich solution containing water and oxygen-containing impurities are regenerated to obtain extractive distillation agent barren solution with purity of 99.9% or more, and the extractive distillation agent barren solution with purity of 99.9% or more is returned to the distillation tower.
Preferably, in step 2), an extractive rectification agent barren solution with a purity of 99.95% or more, and further 99.99% is obtained, and the barren solution is returned to the rectification column.
9. The process according to any one of claims 1-8, wherein in step 2) the regeneration process comprises one or a combination of distillation, stripping (such as azeotropic agent stripping), cold finger process; preferably entrainer stripping. The entrainer in the entrainer stripping is selected from one or more of benzene, toluene, n-heptane, isooctane, isobutane, pentane, hexane and isobutene.
10. The process as claimed in any one of claims 1 to 9, wherein the water content of the lean extractive distillation liquid after the regeneration treatment in step 2) is 50ppm or less, preferably 20ppm or less.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115073397A (en) * | 2022-05-12 | 2022-09-20 | 博大东方新型化工(吉林)有限公司 | Novel epoxypropane dehydration process |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5354430A (en) * | 1993-10-26 | 1994-10-11 | Texaco Chemical Company | Staged purification of contaminated propylene oxide |
| CN105566252A (en) * | 2014-10-24 | 2016-05-11 | 中国石油化工股份有限公司 | Method for purifying epoxypropane (PO) |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5354430A (en) * | 1993-10-26 | 1994-10-11 | Texaco Chemical Company | Staged purification of contaminated propylene oxide |
| CN105566252A (en) * | 2014-10-24 | 2016-05-11 | 中国石油化工股份有限公司 | Method for purifying epoxypropane (PO) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115073397A (en) * | 2022-05-12 | 2022-09-20 | 博大东方新型化工(吉林)有限公司 | Novel epoxypropane dehydration process |
| CN115073397B (en) * | 2022-05-12 | 2024-01-26 | 博大东方新型化工(吉林)有限公司 | Novel epoxypropane dehydration process |
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Effective date of registration: 20230703 Address after: 100192 rooms 309a and 309b, 3rd floor, building 1, district C, Zhongguancun Dongsheng Science Park, 66 xixiaokou Road, Haidian District, Beijing Patentee after: CENWAY TECHNOLOGIES, Ltd. Address before: 311, 3rd floor, building 7, 18 anningzhuang East Road, Qinghe, Haidian District, Beijing 100085 Patentee before: BEIJING NUOWEI NEW MATERIAL TECHNOLOGY Co.,Ltd. |