CN112569620A - Process system for preparing cyclopentyl methyl ether by using bulkhead reaction rectifying tower - Google Patents
Process system for preparing cyclopentyl methyl ether by using bulkhead reaction rectifying tower Download PDFInfo
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- CN112569620A CN112569620A CN202110026688.0A CN202110026688A CN112569620A CN 112569620 A CN112569620 A CN 112569620A CN 202110026688 A CN202110026688 A CN 202110026688A CN 112569620 A CN112569620 A CN 112569620A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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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
- Y02P20/10—Process efficiency
Abstract
The invention belongs to the technical field of chemical production processes and equipment, and particularly relates to a process system for preparing cyclopentyl methyl ether by using a bulkhead reaction rectifying tower. Cyclopentene and methanol react in the reaction rectification section on the left side of the partition plate of the rectifying tower, dimethyl ether is separated from the top on the left side of the partition plate of the rectifying tower on the partition plate of the partition wall, heterogeneous azeotrope of cyclopentene and water obtained from the top on the right side enters a delaminator for layering, wherein the upper layer is mainly cyclopentene, the lower layer is water, and the cyclopentene is used as a raw material or a water-carrying agent and returns to the rectifying tower. The components extracted from the tower bottom mainly comprise cyclopentyl methyl ether, a small amount of cyclopentanol, cyclopentene and polymerization byproducts. The invention can effectively improve the conversion per pass of cyclopentene, and integrate the chemical conversion and the subsequent product separation and purification into a set of equipment, with wide application prospect.
Description
Technical Field
The invention belongs to the technical field of chemical production processes and equipment, and particularly relates to a process system for preparing cyclopentyl methyl ether by using a bulkhead reaction rectifying tower.
Background
Cyclopentyl methyl ether is a novel green environment-friendly hydrophobic ether solvent. Compared with the traditional ether solvents such as tetrahydrofuran, methyl tert-butyl ether, dioxane and the like, the cyclopentyl methyl ether has the following advantages: strong hydrophobicity, low evaporation latent heat, wide liquid phase range, narrow explosion limit and strong oxidation resistance. The cyclopentyl methyl ether can be used as a green solvent for various reactions such as Grignard reaction, coupling amination reaction, metal reduction reaction and the like, and can also be used for the processes such as extraction, crystallization, polymerization and the like.
European patent EP1405840A discloses three processes for the preparation of cyclopentyl methyl ether: (1) a fixed bed reactor is adopted, a certain amount of SPC118, Amberlyst-15, PK228LH and RCP145 acidic cation exchange resin are filled in a reaction tube in sequence to be used as catalysts, high-purity cyclopentene and methanol are used as raw materials, and the specific reaction conditions are as follows: the reaction temperature is 90 ℃, and the mole ratio of cyclopentene to methanol is 1.6: 1, the feeding flow is 0.8ml/min, the conversion rate of cyclopentene is analyzed after the reaction time is 7 hours, and the conversion rates of cyclopentene corresponding to the different catalysts are respectively 68.9%, 68.0%, 50.1% and 27.0% -56.2%. (2) Adding 283g N N-dimethylformamide as solvent into a kettle reactor, replacing air in the kettle with nitrogen, adding sodium hydride containing 60wt% of oily substances, slowly adding 103.3g of cyclopentanol dropwise into the kettle at 50 ℃, heating the reaction liquid to 110 ℃ within 1h, carrying out reflux reaction at 110-120 ℃ for 1h, cooling the reaction liquid to 50 ℃, dropwise adding 341.0g of methyl iodide, carrying out reflux reaction at 110-120 ℃ for 5h, and finally evaporating and rectifying the reaction liquid to obtain the cyclopentyl methyl ether with the purity of 99.8%. (3) The method adopts a kettle type reactor and takes an acid cation exchange resin RCP145 as a catalyst, wherein the addition amount of cyclopentene serving as a raw material =3.0g, the addition amount of methanol =32.0g, the addition amount of resin =3.0g, the reaction temperature =120 ℃, the reaction pressure is 2.5Mpa, the reaction time is 6-8h, and the conversion rate of the cyclopentene is 30 percent finally.
In the Chinese patent CN103342624A, the carbon five fraction rich in cyclopentene is mixed with hydrogen and then is subjected to selective hydrogenation reaction, and the catalyst is Pd/Al2O3(ii) a The molar feeding ratio of hydrogen to diolefin in the material is 1-3: 1, and the mass space velocity is 1-8 hr-1The reaction pressure is 10-20 bar, and the reaction temperature is 30-90 ℃. 2) Mixing the hydrogenation reaction liquid with methanol, and then carrying out etherification reaction, wherein the catalyst is strong acid cation exchange resin; the molar ratio of the methanol to the cyclopentene is 0.3-1.0: 1, and the mass space velocity is 1-5 hr-1The reaction pressure is 2-10 bar, and the reaction temperature is 80-140 ℃; refining the etherification reaction liquid to obtain high-purity cyclopentyl methyl ether.
The prior art has the following problems: (1) the conversion rate of cyclopentene in the system is lower under the conventional reaction condition due to the limitation of thermodynamics; (2) the azeotrope exists in the system, the subsequent separation is complex, and the problem is not paid much attention at present.
Disclosure of Invention
The invention aims to provide a process system for preparing cyclopentyl methyl ether by using a bulkhead reactive distillation tower, which breaks the thermodynamic equilibrium limit of the etherification reaction of cyclopentene and methanol by a heterogeneous bulkhead reactive distillation technology, solves the defects in the existing method and solves the trouble of difficult product separation.
In order to achieve the purpose, the invention adopts the following technical scheme:
the process system comprises the following equipment: a bulkhead reaction rectifying tower, two condensers, a delayer and a reboiler; wherein the two condensers are condensers positioned on reflux pipelines at the left side and the right side of the top of the bulkhead reactive distillation tower, the delayer is a delayer positioned on a discharge pipeline at the right side of the top of the bulkhead reactive distillation tower, and the reboiler is a reboiler positioned on a reflux pipeline at the tower bottom of the bulkhead reactive distillation tower; the middle upper part of the bulkhead reaction rectifying tower is provided with a vertical clapboard, the left side of the clapboard is a reaction rectifying section, the left upper side of the clapboard is a dimethyl ether separating section, the right side of the clapboard is a cyclopentene and water heterogeneous azeotrope separating section, and the lower side of the clapboard is a public stripping section; the upper side of the reaction rectifying section is provided with a methanol raw material inlet, and the lower side of the reaction rectifying section is provided with a cyclopentene raw material inlet; the light component dimethyl ether in the reaction system is separated and extracted through a left rectification section; other components in the system enter a public stripping section of a bulkhead type reactive distillation tower, wherein the heterogeneous azeotrope of cyclopentene and water rapidly enters a right separation section of the distillation tower, is condensed and extracted from the right tower top and enters a delayer, and cyclopentene in the upper oil phase is used as a raw material for recycling; the main components of the tower bottom are cyclopentyl methyl ether, a small amount of methanol, cyclopentanol and cyclopentene oligomerization byproducts.
Further, a part or all of the reaction rectifying section on the left side of the partition plate of the bulkhead reaction rectifying tower is filled with a solid acid catalyst; the separation zone and the bottom zone are then filled with structured packing or trays.
Furthermore, the theoretical plate number of the reaction rectifying section is 6-16, the theoretical plate number of the left rectifying section is 3-9, the theoretical plate number of the right separating section is 10-18, and the theoretical plate number of the public stripping section is 10-15.
Furthermore, the reflux ratio of the left side of the next-wall reaction rectifying tower is 0.5-1.5, and the reflux ratio of the right side is 2-3.
Furthermore, the operation pressure of the bulkhead reaction rectifying tower is 0.1-1.0 MPa.
Further, the mol ratio of the cyclopentene and the methanol fed into the reactive distillation section is 0.2-0.8.
The invention has the following remarkable advantages:
the invention can effectively improve the conversion per pass of cyclopentene, and integrate the chemical conversion and the subsequent product separation and purification into a set of equipment, with wide application prospect.
Drawings
FIG. 1 is a schematic diagram of the apparatus of the present invention, 1-dividing wall reaction rectifying column, 2-condenser, 3-condenser, 4-laminator, 5-reboiler;
FIG. 2 is a schematic view of the process of the present invention.
Detailed Description
In order to make the present invention more comprehensible, the technical solutions of the present invention are further described below with reference to specific embodiments, but the present invention is not limited thereto.
The process system comprises the following equipment: the device comprises a bulkhead reaction rectifying tower, condensers, a delayer and a reboiler, wherein the condensers are positioned on reflux pipelines at the left side and the right side of the top of the bulkhead reaction rectifying tower, the delayer is positioned on a discharge pipeline at the right side of the top of the bulkhead reaction rectifying tower, and the reboiler is positioned on a reflux pipeline at a tower kettle of the bulkhead reaction rectifying tower.
The middle upper part of the bulkhead reaction rectifying tower is provided with a vertical clapboard, the left side of the clapboard is a reaction rectifying section, the left upper side of the clapboard is a dimethyl ether separation section, the right side of the clapboard is a cyclopentene and water heterogeneous azeotrope separation section, and the lower side of the clapboard is a public stripping section. The upper side of the reaction rectifying section is provided with a methanol raw material inlet, and the lower side is provided with a cyclopentene raw material inlet. The light component dimethyl ether in the reaction system is separated and extracted through a left rectification section; other components in the system enter a public stripping section of the bulkhead type reactive distillation tower, wherein the heterogeneous azeotrope of cyclopentene and water rapidly enters a right separation section of the distillation tower, is condensed and extracted from the right tower top and enters a delayer, and the cyclopentene in the upper oil phase is recycled as a raw material. The main components of the tower bottom are cyclopentyl methyl ether, a small amount of methanol, cyclopentanol and cyclopentene oligomerization byproducts.
The specific process comprises the following steps: raw material methanol enters a bulkhead type reaction rectifying tower from a feed inlet at the upper end outside the reaction separation area, raw material cyclopentene enters the bulkhead type reaction rectifying tower from a feed inlet at the lower end outside the reaction separation area, and the two raw materials are subjected to etherification reaction under the action of an acidic cation exchange resin catalyst to generate target products of cyclopentyl methyl ether, by-products of dimethyl ether, water and cyclopentene oligomers. The by-product dimethyl ether is separated through a primary rectification section at the upper end of the reaction area, the main component obtained at the tower top is dimethyl ether, and the azeotrope of cyclopentene and water is condensed by a condenser and then flows back to the tower from the tower top. In a public stripping section below a partition plate of the bulkhead type reactive distillation tower, high-boiling-point components including cyclopentyl methyl ether, a small amount of cyclopentanol and cyclopentene oligomers are separated, a part of the separated high-boiling-point components is extracted as a product after heat exchange of a reboiler at the bottom of the tower, and a part of the separated high-boiling-point components is returned to the tower as reflux rising steam at the bottom of the tower. The azeotropic mixture of cyclopentene and water is separated by the secondary rectifying section on the right side of the baffle plate and extracted from the right side tower top, condensed by the tower top water condenser and then enters the delaminating device, the upper layer in the delaminating device is oil phase, mainly cyclopentene, and the lower layer is water phase, mainly water. The cyclopentene can be used as water-carrying agent or raw material for recycling.
Example 1:
the enol molar ratio of reaction feeding is 0.5, the total feeding amount is 1ml/min, the catalyst is acidic ion exchange resin Amberlyst36, the number of theoretical plates of a reaction section is 6, the number of theoretical plates of a left rectification section is 3, the number of theoretical plates of a right separation section is 10, the number of theoretical plates of a common stripping section is 10, the reflux ratio of the left side of a dividing wall tower is 0.5, the reflux ratio of the right side is 2, and the operation pressure of the tower is 0.5 MPa. The selectivity of the by-product dimethyl ether is 50 percent, and the purity of the product cyclopentyl methyl ether is 99 percent.
Example 2:
the enol molar ratio of reaction feeding is 0.6, the total feeding amount is 1ml/min, the catalyst is acidic ion exchange resin Amberlyst36, the number of theoretical plates of a reaction section is 8, the number of theoretical plates of a left side rectifying section is 6, the number of theoretical plates of a right side separating section is 12, the number of theoretical plates of a common stripping section is 13, the reflux ratio of the left side of a dividing wall tower is 0.8, the reflux ratio of the right side is 2.5, and the operation pressure of the tower is 0.8 MPa. The selectivity of the byproduct dimethyl ether is 40 percent, and the purity of the product cyclopentyl methyl ether is 99 percent.
Example 3:
the enol molar ratio of reaction feeding is 0.5, the total feeding amount is 1ml/min, the catalyst is acidic ion exchange resin Amberlyst36, the number of theoretical plates of a reaction section is 6, the number of theoretical plates of a left rectification section is 3, the number of theoretical plates of a right separation section is 10, the number of theoretical plates of a common stripping section is 10, the reflux ratio of the left side of a dividing wall tower is 0.5, the reflux ratio of the right side is 2, and the operation pressure of the tower is 0.7 MPa. The selectivity of the by-product dimethyl ether is 50 percent, and the purity of the product cyclopentyl methyl ether is 98 percent.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and all equivalent changes and modifications made in the claims of the present invention should be covered by the present invention.
Claims (6)
1. A process system for preparing cyclopentyl methyl ether by using a bulkhead reaction rectifying tower is characterized by comprising the following equipment: a bulkhead reaction rectifying tower, two condensers, a delayer and a reboiler; wherein the two condensers are condensers positioned on reflux pipelines at the left side and the right side of the top of the bulkhead reactive distillation tower, the delayer is a delayer positioned on a discharge pipeline at the right side of the top of the bulkhead reactive distillation tower, and the reboiler is a reboiler positioned on a reflux pipeline at the tower bottom of the bulkhead reactive distillation tower; the middle upper part of the bulkhead reaction rectifying tower is provided with a vertical clapboard, the left side of the clapboard is a reaction rectifying section, the left upper side of the clapboard is a dimethyl ether separating section, the right side of the clapboard is a cyclopentene and water heterogeneous azeotrope separating section, and the lower side of the clapboard is a public stripping section; the upper side of the reaction rectifying section is provided with a methanol raw material inlet, and the lower side of the reaction rectifying section is provided with a cyclopentene raw material inlet; the light component dimethyl ether in the reaction system is separated and extracted through a left rectification section; other components in the system enter a public stripping section of a bulkhead type reactive distillation tower, wherein the heterogeneous azeotrope of cyclopentene and water rapidly enters a right separation section of the distillation tower, is condensed and extracted from the right tower top and enters a delayer, and cyclopentene in the upper oil phase is used as a raw material for recycling; the main components of the tower bottom are cyclopentyl methyl ether, a small amount of methanol, cyclopentanol and cyclopentene oligomerization byproducts.
2. The process system of claim 1, wherein the reaction-rectification section on the left side of the bulkhead reaction-rectification column is partially or completely filled with the solid acid catalyst; the separation zone and the bottom zone are then filled with structured packing or trays.
3. The process system according to claim 1, wherein the number of theoretical plates of the reactive distillation section is 6 to 16, the number of theoretical plates of the left-side distillation section is 3 to 9, the number of theoretical plates of the right-side separation section is 10 to 18, and the number of theoretical plates of the common stripping section is 10 to 15.
4. The process system of claim 1, wherein the reflux ratio on the left side of the divided reactive distillation column is 0.5 to 1.5 and the reflux ratio on the right side is 2 to 3.
5. The process system of claim 1, wherein the bulkhead reactive distillation column is operated at a pressure of 0.1 to 1.0 MPa.
6. The process system for preparing cyclopentyl methyl ether according to claim 1, wherein the molar ratio of the cyclopentene and methanol fed into the reactive distillation section is 0.2-0.8.
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| US20030230476A1 (en) * | 2002-06-14 | 2003-12-18 | Bill Brady | Process for the purification of mixtures of toluenediisocyanate incorporating a dividing-wall distillation column |
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| CN109776284A (en) * | 2017-11-15 | 2019-05-21 | 江苏鼎烨药业有限公司 | A kind of preparation method of 2- methoxyl group propylene |
| CN110090464A (en) * | 2019-04-16 | 2019-08-06 | 天津大学 | Partition wall reactive distillation method and device for polymethoxy dimethyl ether synthesis |
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2021
- 2021-01-09 CN CN202110026688.0A patent/CN112569620B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB727614A (en) * | 1951-12-29 | 1955-04-06 | Foster Wheeler Ltd | Improvements in and relating to distilling apparatus |
| US20040210093A1 (en) * | 2001-07-05 | 2004-10-21 | Catalytic Distillation Technologies | Process and apparatus for catalytic distillations |
| US20030230476A1 (en) * | 2002-06-14 | 2003-12-18 | Bill Brady | Process for the purification of mixtures of toluenediisocyanate incorporating a dividing-wall distillation column |
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| CN103694088A (en) * | 2013-12-12 | 2014-04-02 | 中石化上海工程有限公司 | Method for separating ethylene glycol mixture series |
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| CN110090464A (en) * | 2019-04-16 | 2019-08-06 | 天津大学 | Partition wall reactive distillation method and device for polymethoxy dimethyl ether synthesis |
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