CN111375439B - Method and catalyst for preparing epoxypropane by liquid-phase propylene in one step - Google Patents
Method and catalyst for preparing epoxypropane by liquid-phase propylene in one step Download PDFInfo
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- CN111375439B CN111375439B CN202010320820.4A CN202010320820A CN111375439B CN 111375439 B CN111375439 B CN 111375439B CN 202010320820 A CN202010320820 A CN 202010320820A CN 111375439 B CN111375439 B CN 111375439B
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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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/041—Mesoporous materials having base exchange properties, e.g. Si/Al-MCM-41
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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
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
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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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- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
- B01J2229/183—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself in framework positions
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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
- 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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- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention relates to the field of chemical industry, in particular to a method for preparing propylene oxide by liquid-phase propylene in one step and a catalyst. The catalyst of the invention is composed of 5-10 parts of cerium and the balance of Ti-MCM41 molecular sieve by weight part of 100. The invention solves the problems of high raw material cost, serious three-waste pollution, difficult product separation and purification and the like in the traditional propylene oxide preparation method, can effectively improve the conversion rate of propylene and the selectivity of propylene oxide in the propylene oxide preparation process, and has the advantages of low raw material cost, no three-waste discharge and zero process pollution.
Description
Technical Field
The invention relates to the field of chemical industry, in particular to a method for preparing propylene oxide by liquid-phase propylene in one step and a catalyst.
Background
Propylene oxide, also known as propylene oxide, methyl ethylene oxide, is a very important organic compound starting material, second only to polypropylene and acrylonitrile, the third largest propylene derivative. The epoxy propane is colorless ether liquid, low boiling point and inflammable. With chirality, the commercial product is typically a racemic mixture of two enantiomers. Mixing with water, ethanol and diethyl ether. Form binary azeotropic mixtures with pentane, pentene, cyclopentane, cyclopentene, dichloromethane. Toxic, irritating to mucous membranes and skin, and can damage the cornea and conjunctiva of the eye, causing respiratory pain, skin burns and swelling, and even tissue necrosis.
Propylene Oxide (PO) is the third largest propylene derivative except polypropylene and acrylonitrile, is an important basic organic chemical synthesis raw material and is 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. The derivative of the epoxypropane is widely used in the industries of automobiles, buildings, food, tobacco, medicines, cosmetics and the like. The produced downstream products are hundreds of types and are important raw materials of fine chemical products.
Propylene oxide is an important derivative of propylene, with about 7% of propylene being used for propylene oxide production each year. The production process mainly comprises a chlorohydrination method, a co-oxidation method (also called an indirect oxidation method) and a direct oxidation method. The predominant commercial processes for the worldwide production of propylene oxide today are the chlorohydrination process and the co-oxidation process, which in turn is divided into the ethylbenzene co-oxidation process and the isobutane co-oxidation process. In recent years, a cumene oxidation process and a hydrogen peroxide direct oxidation process have been successfully developed and successively realized for industrial production, and a direct oxidation process using oxygen as an oxidizing agent is also under development.
Chlorohydrin process
The chlorohydrin process has been a long-standing process, has been commercialized for over 60 years, and is represented by the chlorohydrin process of Dow chemical (Dow chemical) in the United states. The chlorohydrination process mainly comprises chlorohydrination of propylene, saponification of lime milk and product refining, and is characterized by mature production process, large elasticity of operation load, good selectivity and low requirement for the purity of the raw material propylene, thereby improving the safety of production and reducing construction investment. Because the investment of fixed assets is less, the product cost is lower, and the product has stronger cost competitiveness. The worldwide production of propylene oxide is now about 40% of the chlorohydrin process.
The chlorohydrin method has the defects of high water resource consumption, generation of a large amount of wastewater and waste residues, generation of 40-50 t of chloride-containing saponified wastewater and more than 2t of waste residues every 1t of propylene oxide production, high temperature, high pH value, high chlorine content, high COD content and high suspended matter content, and difficulty in treatment. Meanwhile, the chlorohydrin method also consumes a large amount of chlorine and lime raw materials with high energy consumption, chlorine and calcium are discharged in wastewater and waste residues, and hypochlorous acid generated in the production process has serious corrosion to equipment.
The production of the epoxy propane in China begins in the 60's of the 20 th century and adopts a self-developed technological route of a chlorohydrin method. In the late 20 th century and early 90 s, the chlorohydrin process technology of Japan Xuxu nitre company, Sanjing Dongguan company, Showa electrician company and Dow company in America was introduced in China, and good economic benefits were obtained after the construction and production of propylene oxide devices of enterprises such as brocade chemical industry, Shandong Binshi chemical industry, Zhongshiyu Shanghai Gaoqiao petrochemical industry, Tianjin staphyla chemical industry and the like, and the production level was greatly improved. At present, the chlorohydrin process is used in 80 percent of the available propylene oxide production capacity in China except that the 25 ten thousand ton/a propylene oxide device of the Zhonghai shell adopts the co-oxidation process.
Co-oxidation process
The co-oxidation method is also called Hakang method, and comprises 2 kinds of iso-butane co-oxidation method and ethyl benzene co-oxidation method, wherein iso-butane or ethyl benzene and propylene are respectively subjected to co-oxidation reaction to generate tert-butyl alcohol or styrene, and simultaneously, propylene oxide is co-produced.
The co-oxidation process was developed by Oakland, USA, and is now owned by Lyondell, also known as Liander, USA. The co-oxidation method overcomes the defects of heavy corrosion, more sewage and the like of a chlorohydrin method, and has the advantages of low product cost (co-product apportionment cost), less environmental pollution and the like. Since the industrialization in 1969, the worldwide development is rapid, and the co-oxidation method propylene oxide production accounts for about 55% of the world total production energy nowadays.
The co-oxidation method has the defects of long process flow, various raw materials, high requirement on propylene purity, high pressure for process operation, high equipment cost and high construction investment, and the equipment is made of alloy steel. Meanwhile, in the production of the propylene oxide by the co-oxidation method, only 1 coproduct with low yield is produced, 2.2-2.5 t of styrene or 2.3t of tert-butyl alcohol needs to be co-produced in each ton of propylene oxide, the mutual restriction factors of raw material sources and product sales are large, the mutual restriction factors are required to be properly solved, and the advantages of the process can be shown only when the market requirements of the propylene oxide and the coproduct are matched. In addition, the sewage generated by the co-oxidation method also has higher COD content, and the treatment cost accounts for about 10 percent of the total investment.
Cumene oxidation process
The cumene oxidation process was developed by Sumitomo chemical company, japan, and employs a fixed bed reactor with a titanium-based catalyst, Cumene Hydroperoxide (CHP) as an oxidant, and CHP epoxidizes propylene to obtain propylene oxide and dimethyl benzyl alcohol, which are dehydrated to alpha-methylstyrene, and then hydrogenated to cumene, which is oxidized to CHP for recycling.
The cumene oxidation process is actually 1 improvement of the co-oxidation process, and is mainly different from the co-oxidation process in that cumene is used instead of ethylbenzene, and is recycled without producing co-products. Because the process does not need auxiliary equipment required by co-production of styrene, the investment cost of the device is about 1/3 lower than that of the co-oxidation method, and corrosion-resistant equipment required by the chlorohydrin method process using chlorine gas is not required. In 5 months 2003, Sumitomo chemical corporation invests more than 1 hundred million dollars, and in Japan, thousands of leaves build a 20-million/a propylene oxide plant that uses its own unique cumene oxidation process. Additionally, Sumitomo and Saudi Arabia-American oil company (Saudi Aramco) in Saudi's co-venture corporation will also use the Sumitomo cumene oxidation process technology to build 20 million/a propylene oxide plants.
HPPO process
The hydrogen peroxide direct oxidation method (HPPO method) is a new process for preparing propylene oxide by catalyzing and epoxidizing propylene with hydrogen peroxide (hydrogen peroxide), only generates propylene oxide and water in the production process, has simple process flow, high product yield, no other co-products and basically no pollution, and belongs to an environment-friendly clean production system.
The hydrogen peroxide direct oxidation process is jointly developed and industrially popularized by the winning industry group (original Degussa, Degussa) and wood (Uhde) company and the dow chemical and BASF (BASF) company respectively.
In 2001, the winning industry group and the wood company built 1 set of hydrogen peroxide experimental devices in frankfurt, germany, tested the optimal catalyst and determined critical parameters, and started industrial design of the technology. In 2003, a commercial process kit for the technology was won.
In the year 2006, the SKC company of Korean propylene oxide and polyester film manufacturers began to build the world 1 st set of hydrogen peroxide method propylene oxide device in Korea Yushan from winning and Wood's purchase patents, the production scale of the device is 10 ten thousand t/a, and the device is already built and put into production in the year 2008 of 7 months and has good production operation. The winning industrial group is negotiating with Sibur, a subsidiary of russian natural gas oligopolis, planning the construction of a combined production plant for hydrogen peroxide and propylene oxide in russia.
In 2001, Dow chemical purchased laboratory technology from EniChem for the production of propylene oxide using hydrogen peroxide as the oxidant and included 1 set of test units in Italy. In 2003, the dow chemistry and basf began to collaborate to develop and commercialize hydrogen peroxide process technology. In 2006, the dow chemical and basf company together announced that a 30-ten-thousand-ton/a hydrogen peroxide method propylene oxide plant was built in the united resources of attemper, belgium, and planned to be built and put into production at the beginning of 2009. In 6 months of 2008, the propylene oxide plant of the SCG-DOW group built by the Dow chemical and the SiamCement group (SCG) in Thailand works, the hydrogen peroxide process technology developed by the Dow and the Pasteur jointly is used, the capacity is 39 million t/a, and the project is expected to be put into operation in 2011. The Dow chemical project was also planned to start in Switzerland in 2010 to build a 38-million/a project of propylene oxide by the hydrogen peroxide process.
Direct oxidation with oxygen
Lyondell, usa is developing a direct oxidation technology for converting propylene, hydrogen and oxygen into propylene oxide, using 1 bi-functional catalyst consisting of palladium and titanium silicate, with hydrogen and oxygen to produce hydrogen peroxide and then immediately converting propylene into propylene oxide, and the whole process is completed in 1 reactor. The company has 1 experimental set up in the united states to further bring the process to industrialization. This process is still in the experimental stage today.
The prior various propylene oxide production methods still have the problems of high raw material cost, serious three-waste pollution, difficult product separation and purification and the like. If the propylene oxide can be prepared by propylene and oxygen one-step method with high selectivity, the production cost and the process flow can be greatly reduced, and a green, environment-friendly and competitive production route can be realized.
Disclosure of Invention
In order to solve the problems of high raw material cost, serious three-waste pollution, difficult product separation and purification and the like in the traditional propylene oxide preparation method, the invention provides a cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst which can effectively utilize propylene to prepare propylene oxide.
The technical scheme of the invention is as follows:
a cerium-titanium bimetal framework type MCM-41 molecular sieve catalyst is composed of, by weight, 100 parts of cerium 5-10 parts and the balance of a Ti-MCM41 molecular sieve.
Preferably, the cerium-titanium bimetal framework type MCM-41 molecular sieve catalyst consists of 8 parts of cerium and the balance of Ti-MCM41 molecular sieves by weight part of 100.
A preparation method of the cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst comprises the following steps:
b1: grinding the Ti-MCM41 molecular sieve for later use;
b2: adding cerium carbonate into a citrulline aqueous solution at the isoelectric point of creatine, and adjusting the pH of a mixed solution formed by the cerium carbonate and the citrulline aqueous solution to the isoelectric point of creatine by using dilute hydrochloric acid to obtain an amino acid metal complex solution;
b3: adding a Ti-MCM41 molecular sieve into the amino acid metal complex solution obtained from the B2, soaking for 12-24 hours at room temperature, heating to 80-90 ℃, and carrying out secondary purification for 12-24 hours;
b4: filtering, washing with distilled water of the same volume for 3-5 times, and drying at the temperature of 120-150 ℃ for 4-6 hours to obtain the cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst.
A method for preparing propylene oxide by liquid phase propylene in one step comprises the following steps:
filling a bed layer formed by the cerium-titanium bimetallic framework MCM-41 molecular sieve catalyst in a slurry bed reactor, taking a mixed solution of C12-16 straight-chain alkane and DMF as a solvent, taking propylene and oxygen as raw materials, and reacting at the temperature of 80-120 ℃, the reaction pressure of 0.5-1.5MPa and the weight space velocity of 0.1-1 hour -1 Introducing into the slurry bed reactor under the condition, and carrying out direct epoxidation reaction on propylene through a bed layer formed by the cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst to prepare propylene oxide.
Preferably, the first and second electrodes are formed of a metal,the reaction temperature is 120 ℃, the reaction pressure is 1.3MPa, and the weight space velocity is 0.8 hour -1。
Compared with the prior art, the invention has the following technical effects:
1) the raw material cost is low, the process route is simple and efficient, and the economic advantages are remarkable: the invention takes cheap propylene and oxygen as raw materials, is not suitable for expensive oxidants such as hydrogen peroxide and the like, and adopts a slurry bed reactor to realize the preparation of the propylene oxide by gas, liquid and solid phases with high selectivity under the action of a cerium-titanium bimetallic molecular sieve and a solvent;
2) the technical route is advanced, the raw materials have no toxicity, no three-waste discharge and zero process pollution;
3) simple separation and purification and high product selectivity: the method adopts propylene and oxygen as raw materials, and reduces the possibility of propylene being oxidized into acrylic acid and further being oxidized into carbon dioxide under the action of the cerium-titanium-silicon molecular sieve and the solvent effect. The selectivity of the main product of the propylene oxide is greatly improved by utilizing the molecular sieve shape-selecting effect, few byproducts are generated, the composition of reactants is simple, and the cost of the separation and purification process is low.
Detailed Description
In order to make the technical solutions of the present invention better understood and enable those skilled in the art to practice the present invention, the following embodiments are further described, but the present invention is not limited to the following embodiments.
A preparation method of a cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst comprises the following steps:
b1: grinding the Ti-MCM41 molecular sieve for later use;
b2: adding cerium carbonate into a citrulline aqueous solution at the isoelectric point of creatine, and adjusting the pH of a mixed solution formed by the cerium carbonate and the citrulline aqueous solution to the isoelectric point of creatine by using dilute hydrochloric acid to obtain an amino acid metal complex solution;
b3: adding a Ti-MCM41 molecular sieve into the amino acid metal complex solution obtained from the B2, soaking for 12-24 hours at room temperature, heating to 80-90 ℃, and carrying out secondary purification for 12-24 hours;
b4: after filtration, washing the obtained product for 3 to 5 times by using equal volume of distilled water, and drying the product for 4 to 6 hours at the temperature of 120-150 ℃ to obtain the cerium-titanium bimetal framework type MCM-41 molecular sieve catalyst.
Example 1
The cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst used in the example contains 5 parts of cerium and the balance of Ti-MCM41 type molecular sieve by weight of 100. The catalyst was numbered YCSY-01.
Evaluating the performance of the catalyst in a slurry bed reactor, and filling the catalyst to form a catalyst bed layer. Taking propylene and oxygen as raw materials in a molar ratio of 1:1.2, and mixing C12-16 linear paraffin and DMF in a volume ratio of 5: 1, propylene oxide product is produced, and the reaction conditions and results are shown in table 1.
Example 2
The cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst used in the example contains 6 parts of cerium and the balance of Ti-MCM41 type molecular sieve, wherein the weight fraction is 100. The catalyst was numbered YCSY-02.
The catalyst performance evaluation conditions were the same as in example 1, and the reaction conditions and results are shown in Table 1.
Example 3
The cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst used in the example contains 7 parts of cerium and the balance of Ti-MCM41 type molecular sieve by weight of 100. The catalyst was numbered YCSY-03.
The catalyst performance was evaluated in the same manner as in example 1, and the reaction conditions and results are shown in Table 1.
Example 4
The cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst used in the example contains 8 parts of cerium and the balance of Ti-MCM41 type molecular sieve by weight of 100. The catalyst was numbered YCSY-04.
The catalyst performance evaluation conditions were the same as in example 1, and the reaction conditions and results are shown in Table 1.
Example 5
The cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst used in the example contains 9 parts of cerium and the balance of Ti-MCM41 type molecular sieve by weight of 100. The catalyst was numbered YCSY-05.
The catalyst performance evaluation conditions were the same as in example 1, and the reaction conditions and results are shown in Table 1.
Example 6
The cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst used in the example contains 10 parts of cerium and the balance of Ti-MCM41 type molecular sieve, wherein the weight fraction is 100. The catalyst was numbered YCSY-06.
The catalyst performance evaluation conditions were the same as in example 1, and the reaction conditions and results are shown in Table 1.
TABLE 1 test results
Claims (4)
1. A method for preparing propylene oxide by liquid phase propylene in one step is characterized in that: the method comprises the following steps:
filling a bed layer formed by a cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst in a slurry bed reactor, taking a mixed solution of C12-16 straight-chain alkane and DMF as a solvent, taking propylene and oxygen as raw materials, and reacting at the temperature of 80-120 ℃, the reaction pressure of 0.5-1.5MPa and the weight space velocity of 0.1-1 hour -1 Introducing the mixture into the slurry bed reactor under the condition, and carrying out direct epoxidation reaction on propylene through a bed layer formed by the cerium-titanium bimetal framework type MCM-41 molecular sieve catalyst to obtain propylene oxide;
wherein, the cerium-titanium bimetal framework type MCM-41 molecular sieve catalyst is composed of 5-10 parts of cerium and the balance of Ti-MCM41 molecular sieves by weight part of 100.
2. The liquid phase propylene one-step process for preparing propylene oxide according to claim 1, wherein: the preparation method of the cerium-titanium bimetal framework type MCM-41 molecular sieve catalyst comprises the following steps:
b1: grinding the Ti-MCM41 molecular sieve for later use;
b2: adding cerium carbonate into a citrulline aqueous solution at the isoelectric point of creatine, and adjusting p H of a mixed solution formed by the cerium carbonate and the citrulline aqueous solution to the isoelectric point of creatine by using dilute hydrochloric acid to obtain an amino acid metal complex solution;
b3: adding a Ti-MCM41 molecular sieve into the amino acid metal complex solution obtained from the B2, soaking for 12-24 hours at room temperature, heating to 80-90 ℃, and carrying out secondary purification for 12-24 hours;
b4: after filtration, washing the obtained product for 3 to 5 times by using equal volume of distilled water, and drying the product for 4 to 6 hours at the temperature of 120-150 ℃ to obtain the cerium-titanium bimetal framework type MCM-41 molecular sieve catalyst.
3. The liquid phase propylene one-step process for preparing propylene oxide according to claim 1, wherein: the reaction temperature is 120 ℃, the reaction pressure is 1.3MPa, and the weight space velocity is 0.8 hour -1 。
4. The liquid phase propylene one-step process for preparing propylene oxide according to claim 1, wherein: the cerium-titanium bimetallic framework type MCM-41 molecular sieve catalyst consists of 8 parts of cerium and the balance of Ti-MCM41 molecular sieve by weight of 100 parts.
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