CN107987036B - Preparation method of propylene oxide - Google Patents
Preparation method of propylene oxide Download PDFInfo
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- CN107987036B CN107987036B CN201711000046.3A CN201711000046A CN107987036B CN 107987036 B CN107987036 B CN 107987036B CN 201711000046 A CN201711000046 A CN 201711000046A CN 107987036 B CN107987036 B CN 107987036B
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- 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
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
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- 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
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
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- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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- Y02P20/50—Improvements relating to the production of bulk chemicals
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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
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention discloses a preparation method of propylene oxide. Under the action of titanium silicalite molecular sieve catalyst, propylene and H2O2Carrying out epoxidation reaction to generate propylene oxide, and obtaining the propylene oxide product with the purity of more than or equal to 99.5 percent through product separation, gas recovery treatment and crude product refining. The byproduct propylene glycol is obtained by catalyst separation and byproduct separation. In the invention, because no solvent is involved in the reaction process, compared with the process technology for preparing the propylene oxide by using a hydrogen peroxide propylene epoxidation method by using methanol as a solvent, the method has the advantages of low production cost, high safety, low energy consumption, short process flow, low operation cost, low equipment investment, high propylene oxide product purity, conversion rate of hydrogen peroxide of more than or equal to 99 percent, effective utilization rate of hydrogen peroxide of more than or equal to 98.5 percent and selectivity of propylene oxide (calculated by propylene oxide) of more than or equal to 99 percent.
Description
Technical Field
The invention relates to a preparation method of an organic matter, in particular to a preparation method of propylene oxide.
Background
Propylene Oxide (PO) is the third largest propylene derivative except polypropylene and acrylonitrile, and is an important basic organic chemical raw material mainly used for producing polyether, propylene glycol and the like. It is also the main raw material of fourth generation detergent nonionic surfactant, oil field demulsifier, pesticide emulsifier, etc. Derivatives of PO are widely used in the industries of automobiles, buildings, food, tobacco, medicines, cosmetics and the like. In the prior art, the PO production mainly adopts a process (HPPO method) for preparing propylene oxide by using hydrogen peroxide, PO and water are mainly generated in the production process of the process, the process flow is simple, and the product yield is highThe method has less by-products and basically no pollution, and belongs to an environment-friendly clean production process compared with a chlorohydrin method and a co-oxidation method. HPPO process means H2O2The epoxidation of propylene to PO is catalyzed on a TS-1 catalyst, the solvent is methanol, and the operation is carried out under the conditions of medium temperature, low pressure and liquid phase reaction. Two production technologies of the HPPO method exist at present, namely a technology jointly developed by Dow chemical company and BASF company, and a technology jointly developed by Degussa company and Uhde company. In the Dow/BASF process, n (propylene): n (H)2O2) 2:1, m (methanol): m (H)2O2) The reaction temperature is 40-50 ℃, and the reaction pressure is 2.0MPa (G). H2O2The conversion and PO selectivity were 96% and 95%, respectively, and the Degussa process was similar to the BASF process. The two process technologies adopt propylene and H in the presence of a solvent methanol and a catalyst2O2The epoxidation reaction is carried out to generate propylene oxide, in the reaction process, the existence of a solvent methanol can cause long production flow, high investment, energy consumption and operation cost, high contents of byproducts formaldehyde, formic acid, methylal and methyl formate, particularly small boiling point difference between the byproduct methyl formate (boiling point 32 ℃), methylal (boiling point 42 ℃) and the product propylene oxide (boiling point 34 ℃), high rectification separation difficulty, low purity and low polymerization degree of the product propylene oxide, influence on the product propylene oxide reaching the polymerization level, great influence on the production of polymerized polyhydric alcohols and polyether substances, relatively large amount of three wastes and relatively high environmental protection treatment cost.
Disclosure of Invention
The invention aims to provide a method for preparing propylene oxide aiming at the defects of the prior art so as to improve the quality of the product propylene oxide, simplify the process flow, reduce the energy consumption and the production cost and improve the production safety.
The technical scheme adopted by the invention for solving the technical problem is that the preparation method of the propylene oxide comprises the following steps:
(1) reaction of
Continuously adding raw material propylene and H with the mass fraction of 4-90% into a reaction kettle according to the molar ratio of (1.02-1.3): 12O2The method comprises the steps of preparing an aqueous solution, a fresh titanium silicalite molecular sieve catalyst and a pH regulator, controlling the temperature in a reaction kettle to be 25-75 ℃, the pressure to be 0.8-2.8 MPa, the mass fraction of the catalyst to be 1-8%, the pH to be 3.5-11.5, and the retention time to be 20-180 min, and under the action of the catalyst, reacting propylene and H2O2Carrying out epoxidation reaction to generate propylene oxide, obtaining reaction liquid and reaction tail gas containing propylene, a very small amount of propylene oxide and a trace amount of inert gas, sending the reaction liquid to a product separation process, and sending the reaction tail gas to a gas recovery treatment process;
(2) product separation
Distilling and separating the reaction liquid obtained in the step (1) to obtain a crude epoxypropane product and slurry, feeding the crude epoxypropane product into a crude product refining process, returning part of the slurry serving as circulating liquid into the reaction kettle in the step (1) for continuous reaction, and feeding the other part of the slurry into a catalyst separation process, wherein the temperature is 5-40 ℃ and the pressure is-90-30 kPa during distillation;
(3) gas recovery treatment
Treating reaction tail gas containing propylene, a very small amount of propylene oxide and a trace amount of inert gas discharged from the top of the reaction kettle in the step (1) through a gas recovery treatment process to obtain circulating propylene, crude propylene oxide and non-condensable gas, returning the circulating propylene to the reaction kettle in the step (1) to continue reacting, conveying the crude propylene oxide to a crude product refining process, and discharging the non-condensable gas after the non-condensable gas is treated to reach the standard in a waste gas treatment process;
(4) catalyst separation
Separating the catalyst from the other part of the slurry obtained in the step (2) to respectively obtain a catalyst concentrated solution and a by-product clear solution, and sending the by-product clear solution to a by-product separation process; returning part of the catalyst concentrated solution serving as a circulating catalyst to the reaction kettle in the step (1) to continuously participate in the reaction; the other part of the catalyst concentrated solution is sent to a catalyst regeneration process;
(5) refining of the crude product
Rectifying the crude epoxypropane obtained in the steps (2) and (3) through a refining process to obtain a epoxypropane product with the purity of more than or equal to 99.5 percent and process water, and sending the process water to a wastewater pretreatment process; (ii) a
(6) By-product separation
Rectifying and separating the clear liquid of the byproduct obtained in the step (4) to obtain water containing trace organic matters and propylene glycol of which the purity is more than or equal to 99%, and sending the water containing trace organic matters to a wastewater pretreatment process;
(7) catalyst regeneration
Regenerating the catalyst from the other part of the catalyst concentrated solution obtained in the step (4), returning the regenerated catalyst as a regenerated circulating catalyst to the reaction kettle in the step (1) for continuous use, and sending the regenerated catalyst waste liquid to a wastewater pretreatment process;
(8) pretreatment of wastewater
And (4) pretreating the water containing trace organic matters obtained in the step (6) and the catalyst regeneration waste liquid obtained in the step (7), and then discharging the pretreated water and the catalyst regeneration waste liquid to an environment-friendly device for further treatment until the water reaches the standard and is discharged.
In the method, the reaction kettle in the step (1) is in a combined mode of one or more reaction kettles in a fixed bed, a slurry bed and a microreactor.
The process of the invention, preferably under the conditions of step (1), comprises the continuous addition of starting material H2O2Is H with the mass fraction of 5-80%2O2An aqueous solution.
In the method of the present invention, in the step (1), the pH adjuster is an inorganic acid or base or an organic acid or base. One of sodium hydroxide, ammonia, sulfuric acid, phosphoric acid, butyric acid, and triethanolamine is commonly used.
The method has the preferable conditions that in the step (1), the temperature in the reaction kettle is controlled to be 28-68 ℃, the pressure is 1.2-2.5 MPa, the mass fraction of the catalyst is 1.5-4.5%, and the retention time is 30-150 min.
The method has the preferable conditions that in the separation of the product in the step (2), the temperature is 15-25 ℃ and the pressure is-80 to-30 kPa during distillation.
The invention adopts the conventional tower type equipment in the product separation in the step (2), the crude product refining in the step (5) and the by-product separation in the step (6).
The catalyst separation in the step (4) of the invention adopts a membrane separation method, and the used membranes comprise various membranes which can resist propylene glycol, propylene oxide and propylene, such as ceramic membranes, metal membranes, polysulfone membranes, polyamide membranes and the like; the installation mode can be a kettle built-in membrane or a kettle external membrane; the filtration mode can be cross-flow filtration or cross-flow filtration, or other mechanical centrifugal separation equipment or equipment such as gravity settling, static filtration or filter pressing and the like and a corresponding separation mode.
In the process of the present invention, "pressure" means "gauge pressure".
The invention has the following beneficial effects:
according to the method, because no solvent is involved in the reaction process, compared with the existing process technology for preparing the propylene oxide by using a propylene epoxidation method by using methanol as a solvent, no solvent is used in the whole process, so that the production cost is reduced, and the safety is improved; the ineffective decomposition rate of the hydrogen peroxide is extremely low, no complicated gas phase deoxidation procedure and equipment are needed, the process flow is short, and the equipment investment is low; no methanol and impurities brought by the methanol participate in the reaction, the byproduct is single (only propylene glycol), the separation is easy, the purity of the product propylene oxide is improved, and the purity can easily reach more than 99.5%; the conversion rate (calculated by hydrogen peroxide) of the hydrogen peroxide is higher and is more than or equal to 99 percent; the effective utilization rate of the hydrogen peroxide is higher and is more than or equal to 98.5 percent; the mol ratio of the propylene to the hydrogen peroxide is (1.02-1.3) to 1, and the mol ratio is (n (propylene) in the Dow/BASF process): n (H)2O2) The ratio of 2:1 is lower by more than 70%, the separation of propylene is simple, the circulating amount is small, and the production cost is greatly reduced; the selectivity of the propylene oxide (calculated by the propylene oxide) is higher and is more than or equal to 99 percent; less waste water, waste gas and waste residue and less environmental pollution.
Drawings
FIG. 1 is a schematic process flow diagram of the present invention.
Detailed Description
The following examples serve to illustrate the invention.
Example 1
Referring to the process flow diagram of the invention given in fig. 1, the preparation method of the invention comprises the following steps:
(1) reaction of
Continuously adding raw material propylene and H with the mass fraction of 50 percent into a reaction kettle according to the mol ratio of 1.05:12O2Taking an aqueous solution, a fresh titanium silicalite molecular sieve catalyst and 2 mass percent NaOH as pH regulators, controlling the temperature in a reaction kettle to be 42 ℃, the pressure to be 1.6MPa, the catalyst mass percent to be 3 percent, the pH to be 6, and the retention time to be 70min, and under the action of the catalyst, propylene and H2O2Carrying out epoxidation reaction to generate propylene oxide, obtaining reaction liquid and reaction tail gas containing propylene, a very small amount of propylene oxide and a trace amount of inert gas, sending the reaction liquid to a product separation process, and sending the reaction tail gas to a gas recovery treatment process;
wherein the reaction kettle adopts a paddle-state bed reaction kettle;
(2) product separation
Distilling and separating the reaction liquid obtained in the step (1) to obtain a crude epoxypropane product and slurry, feeding the crude epoxypropane product into a crude product refining process, returning part of the slurry serving as circulating liquid into the reaction kettle in the step (1) for continuous reaction, and feeding the other part of the slurry into a catalyst separation process, wherein the temperature during distillation is 24 ℃, and the pressure is-30 kPa;
(3) gas recovery treatment
Treating reaction tail gas containing propylene, a very small amount of propylene oxide and a trace amount of inert gas discharged from the top of the reaction kettle in the step (1) through a gas recovery treatment process to obtain circulating propylene, crude propylene oxide and non-condensable gas, returning the circulating propylene to the reaction kettle in the step (1) to continue reacting, conveying the crude propylene oxide to a crude product refining process, and discharging the non-condensable gas after the non-condensable gas is treated to reach the standard in a waste gas treatment process;
(4) catalyst separation
Separating the catalyst from the other part of the slurry obtained in the step (2) by adopting an external ceramic membrane separation method to obtain a catalyst concentrated solution and a byproduct clear solution respectively, and sending the byproduct clear solution to a byproduct separation process; returning part of the catalyst concentrated solution serving as a circulating catalyst to the reaction kettle in the step (1) to continuously participate in the reaction; the other part of the catalyst concentrated solution is sent to a catalyst regeneration process;
(5) refining of the crude product
Rectifying the crude epoxypropane obtained in the steps (2) and (3) through a refining process to obtain a epoxypropane product with the purity of 99.92% and process water, and sending the process water to a wastewater pretreatment process;
(6) by-product separation
Rectifying and separating the clear liquid of the by-product obtained in the step (4) to obtain water containing trace organic matters and by-product propylene glycol with the purity of 99.46%, and sending the water containing trace organic matters to a wastewater pretreatment process;
(7) catalyst regeneration
Regenerating the catalyst from the other part of the catalyst concentrated solution obtained in the step (4), returning the regenerated catalyst as a regenerated circulating catalyst to the reaction kettle in the step (1) for continuous use, and sending the regenerated catalyst waste liquid to a wastewater pretreatment process;
(8) pretreatment of wastewater
Pretreating the water containing trace organic matters obtained in the step (6) and the catalyst regeneration waste liquid obtained in the step (7), and then discharging the pretreated water and the catalyst regeneration waste liquid to an environment-friendly device for further treatment until the water reaches the standard and is discharged;
in the process of the present invention, "pressure" means "gauge pressure".
Example 2
Referring to the process flow diagram of the invention given in fig. 1, the preparation method of the invention comprises the following steps:
(1) reaction of
Continuously adding raw material propylene and 60 percent of H by mass into a reaction kettle according to the mol ratio of 1.26:12O2Taking an aqueous solution, a fresh titanium silicalite molecular sieve catalyst and 1% ammonia water as pH regulators, controlling the temperature in the reaction kettle to be 43 ℃, the pressure to be 1.7MPa, the catalyst mass fraction to be 2.3%, the pH to be 4.8, and the retention time to be 80min, and under the action of the catalyst, propylene and H2O2Generating epoxypropane by epoxidation reaction to obtain reaction liquid and reaction tail gas containing propylene, a very small amount of epoxypropane and a trace amount of inert gas, and sending the reaction liquid to a product separatorA separation step, wherein reaction tail gas is sent to a gas recovery treatment step;
wherein the reaction kettle adopts a paddle-state bed reaction kettle;
(2) product separation
Distilling and separating the reaction liquid obtained in the step (1) to obtain a crude epoxypropane product and slurry, feeding the crude epoxypropane product into a crude product refining process, returning part of the slurry as a circulating liquid into the reaction kettle in the step (1) for continuous reaction, and feeding the other part of the slurry into a catalyst separation process, wherein the temperature during distillation is 27 ℃, and the pressure is-20 kPa;
(3) gas recovery treatment
Treating reaction tail gas containing propylene, a very small amount of propylene oxide and a trace amount of inert gas discharged from the top of the reaction kettle in the step (1) through a gas recovery treatment process to obtain circulating propylene, crude propylene oxide and non-condensable gas, returning the circulating propylene to the reaction kettle in the step (1) to continue reacting, conveying the crude propylene oxide to a crude product refining process, and discharging the non-condensable gas after the non-condensable gas is treated to reach the standard in a waste gas treatment process;
(4) catalyst separation
Separating the catalyst from the other part of the slurry obtained in the step (2) by adopting a kettle built-in metal membrane separation method to respectively obtain a catalyst concentrated solution and a byproduct clear solution, and sending the byproduct clear solution to a byproduct separation process; returning part of the catalyst concentrated solution serving as a circulating catalyst to the reaction kettle in the step (1) to continuously participate in the reaction; the other part of the catalyst concentrated solution is sent to a catalyst regeneration process;
(5) refining of the crude product
Rectifying the crude epoxypropane obtained in the steps (2) and (3) through a refining process to obtain a epoxypropane product with the purity of 99.86% and process water, and sending the process water to a wastewater pretreatment process;
(6) by-product separation
Rectifying and separating the clear liquid of the by-product obtained in the step (4) to obtain water containing trace organic matters and by-product propylene glycol with the purity of 99.52 percent, and sending the water containing trace organic matters to a wastewater pretreatment process;
(7) catalyst regeneration
Regenerating the catalyst from the other part of the catalyst concentrated solution obtained in the step (4), returning the regenerated catalyst as a regenerated circulating catalyst to the reaction kettle in the step (1) for continuous use, and sending the regenerated catalyst waste liquid to a wastewater pretreatment process;
(8) pretreatment of wastewater
Pretreating the water containing trace organic matters obtained in the step (6) and the catalyst regeneration waste liquid obtained in the step (7), and then discharging the pretreated water and the catalyst regeneration waste liquid to an environment-friendly device for further treatment until the water reaches the standard and is discharged;
in the above embodiments, "pressure" means "gauge pressure".
Claims (5)
1. A method for preparing propylene oxide is characterized by comprising the following steps:
(1) reaction of
Continuously adding raw material propylene and H with the mass fraction of 50-60% into a reaction kettle according to the molar ratio (1.02-1.3) of 12O2The method comprises the steps of preparing an aqueous solution, a titanium silicalite molecular sieve catalyst and a pH regulator, controlling the temperature in a reaction kettle to be 25-75 ℃, the pressure to be 0.8-2.8 MPa, the mass fraction of the catalyst to be 1-8%, the pH to be 4.8-6, and the residence time to be 20-180 min, wherein under the action of the catalyst, propylene and H are reacted2O2Carrying out epoxidation reaction to generate propylene oxide, obtaining reaction liquid and reaction tail gas containing propylene, a very small amount of propylene oxide and a trace amount of inert gas, sending the reaction liquid to a product separation process, and sending the reaction tail gas to a gas recovery treatment process;
(2) product separation
Distilling and separating the reaction liquid obtained in the step (1) to obtain a crude epoxypropane product and slurry, feeding the crude epoxypropane product into a crude product refining process, returning one part of slurry as a circulating liquid into the reaction kettle in the step (1) for continuous reaction, and feeding the other part of slurry into a catalyst separation process, wherein the temperature during distillation is 5-40 ℃, and the pressure is-90-30 kPa;
(3) gas recovery treatment
Treating reaction tail gas containing propylene, a very small amount of propylene oxide and a trace amount of inert gas discharged from the top of the reaction kettle in the step (1) through a gas recovery treatment process to obtain circulating propylene, crude propylene oxide and non-condensable gas, returning the circulating propylene to the reaction kettle in the step (1) to continue reacting, conveying the crude propylene oxide to a crude product refining process, and discharging the non-condensable gas after the non-condensable gas is treated to reach the standard in a waste gas treatment process;
(4) catalyst separation
Separating the catalyst from the other part of the slurry obtained in the step (2) to obtain a catalyst concentrated solution and a by-product clear solution, and sending the by-product clear solution to a by-product separation process; returning a part of the catalyst concentrated solution serving as a circulating catalyst to the reaction kettle in the step (1) to continuously participate in the reaction, and sending the other part of the catalyst concentrated solution to a catalyst regeneration process for regeneration;
(5) refining of the crude product
Rectifying the crude epoxypropane products obtained in the steps (2) and (3) to obtain epoxypropane products with the purity of more than or equal to 99.5% and process water, and sending the process water to a wastewater pretreatment process;
(6) by-product separation
Rectifying and separating the clear liquid of the byproduct obtained in the step (4) to obtain water containing trace organic matters and propylene glycol of which the purity is more than or equal to 99%, and sending the water containing trace organic matters to a wastewater pretreatment process;
(7) catalyst regeneration
Regenerating the catalyst from the other part of the catalyst concentrated solution obtained in the step (4), returning the regenerated catalyst as a regenerated circulating catalyst to the reaction kettle in the step (1) for continuous use, and sending the regenerated catalyst waste liquid to a wastewater pretreatment process;
(8) pretreatment of wastewater
And (4) pretreating the water containing trace organic matters obtained in the step (6) and the catalyst regeneration waste liquid obtained in the step (7), and then discharging the pretreated water and the catalyst regeneration waste liquid to an environment-friendly device for further treatment until the water reaches the standard and is discharged.
2. The preparation method according to claim 1, wherein the reaction vessel in the step (1) is in the form of one or a combination of two reaction vessels selected from a fixed bed and a slurry bed.
3. The method according to claim 1, wherein the pH adjusting agent in the step (1) is one of sodium hydroxide, ammonia water, sulfuric acid, phosphoric acid, butyric acid and triethanolamine.
4. The preparation method according to claim 1, wherein in the step (1), the temperature in the reaction kettle is controlled to be 28-68 ℃, the pressure is 1.2-2.5 MPa, the mass fraction of the catalyst is 1.5-4.5%, and the retention time is 30-150 min.
5. The process according to claim 1, wherein the temperature in the distillation in the step (2) is 15 to 25 ℃ and the pressure is-80 to-30 kPa.
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| CN108997264A (en) * | 2018-08-22 | 2018-12-14 | 湖南长科诚享石化科技开发有限公司 | A kind of consersion unit and technique of hydrogen peroxide legal system propylene oxide |
| CN111116519B (en) * | 2018-10-30 | 2022-11-01 | 中国石油化工股份有限公司 | Alkylene oxide utilization method |
| CN110642810A (en) * | 2019-10-14 | 2020-01-03 | 河北美邦工程科技股份有限公司 | Solvent-free sectional type epichlorohydrin production method |
| CN110642808A (en) * | 2019-10-15 | 2020-01-03 | 河北美邦工程科技股份有限公司 | Production method of segmented epichlorohydrin |
| EP4171804A1 (en) * | 2020-06-26 | 2023-05-03 | Lyondell Chemical Technology, L.P. | Use of monopropylene glycol from purge streams in epoxidation catalyst preparation |
| CN116283833A (en) * | 2023-04-11 | 2023-06-23 | 南京舒宜汇科学仪器有限公司 | Process for preparing epoxypropane by directly oxidizing propylene |
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| CN1256274A (en) * | 1998-12-09 | 2000-06-14 | 中国石油化工集团公司 | Technological process of oxidizing propylene with hydrogen peroxide solution to produce epoxy propane continuously |
| CN101279957A (en) * | 2007-04-04 | 2008-10-08 | 中国石油化工股份有限公司 | Method for preparing epoxypropane by epoxidation of propene |
| CN105439815A (en) * | 2014-08-21 | 2016-03-30 | 中国石油化工股份有限公司 | Method for preparing propylene glycol |
| CN106967010A (en) * | 2016-01-13 | 2017-07-21 | 中国石油化工股份有限公司 | A kind of chloropropene method for oxidation |
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