CN111153782A - Method for preparing high-carbon aldehyde by hydroformylation of high-carbon olefin - Google Patents
Method for preparing high-carbon aldehyde by hydroformylation of high-carbon olefin Download PDFInfo
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- CN111153782A CN111153782A CN201911424545.4A CN201911424545A CN111153782A CN 111153782 A CN111153782 A CN 111153782A CN 201911424545 A CN201911424545 A CN 201911424545A CN 111153782 A CN111153782 A CN 111153782A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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Abstract
The invention relates to a method for preparing high-carbon aldehyde by hydroformylation of high-carbon olefin. The method comprises the following steps: (1) providing a fiber membrane reactor and a stirred tank reactor, and respectively contacting high-carbon olefin and synthesis gas with a catalyst in the fiber membrane reactor and the stirred tank reactor under certain conditions to generate corresponding high-carbon aldehyde; (2) gas phase and liquid phase in the fiber membrane reactor enter a stirred tank reactor for separation; (3) cooling the reaction liquid in the stirred tank reactor, conveying the reaction liquid to the top of the fiber membrane reactor, and returning part of the reaction liquid to the stirred tank reactor to control the temperature; (4) condensing and cooling the mixed gas discharged from the top of the stirred tank reactor, returning the liquid phase to the stirred tank reactor, and discharging the gas phase; (5) and overflowing the liquid phase in the stirred tank reactor, cooling the liquid phase to enter an aldehyde-water separator for aldehyde-water separation, removing the crude aldehyde for subsequent refining, and circulating the catalyst solution to the stirred tank reactor. The invention can improve the hydroformylation reaction efficiency, reduce the side reaction and reduce the loss of the catalyst.
Description
Technical Field
The invention relates to a preparation method of aldehydes or an olefin hydroformylation reaction method, in particular to a method for preparing high-carbon aldehydes by hydroformylation of high-carbon olefins, belonging to the field of preparation of aldehydes.
Background
The hydroformylation of olefins with synthesis gas over a catalyst to produce aldehydes having one more carbon atom than the olefin is a well known process, and the equation is as follows:
the hydroformylation reactors used in the current industrial production, whether kettle type reactors with stirring or tower type reactors, belong to back-mixing type reactors, and for the hydroformylation reaction of olefin, carbon monoxide and hydrogen, under the reaction conditions, the olefin, the carbon monoxide and the hydrogen are all gas phases, and the catalyst is dissolved in water and is a liquid phase. The solubility of olefin, carbon monoxide and hydrogen in water is very low, and the materials can be mixed only by bubbling gas in a back-mixing reactor. In commercial reactors, this reaction is actually controlled by the mass transfer rate at the gas-liquid two-phase interface. Therefore, for the hydroformylation reactor of olefin, the key to improving the efficiency of the reactor is strengthening the mass transfer.
The main way of strengthening the mass transfer of the reactor is to increase the mass transfer interface, and for the bubbling type reactor without stirring, the mass transfer is strengthened and improved only by a proper gas distributor. In such bubbling back mixing devices (e.g., column type devices), because there is no mixing energy input, the bubbles cannot be fine enough, and in order to have a sufficient mass transfer area, a large enough space is necessary, which makes the device bulky, the utilization efficiency of the device is low, and the investment is large. The stirred tank reactor has many disadvantages, and because of the limitation of stirring speed, the dispersion of gas in the catalyst aqueous solution is influenced, and the mass transfer effect is influenced, especially the large scale and the large size of the reaction kettle are more prominent.
In order to increase the conversion of olefins, two or more reactors can be operated in series, and chinese patent CN86101063 discloses an improved hydroformylation method, which allows unconverted raw materials in the first reaction zone and supplementary CO/H2 gas to enter the second reaction zone together for further reaction, thereby increasing the conversion per pass of olefins. Similar practices are disclosed in GB1387657, US5105018 and US 5367106.
In order to improve the reaction efficiency, CN102649718 discloses a rotary packed bed hypergravity high-efficiency reactor, which can improve the mass transfer efficiency by geometric order of magnitude, further greatly improve the reaction rate of hydroformylation of olefins from C2 to C8, and simultaneously, greatly shorten the retention time and effectively improve the selectivity. Because the dynamic seal under high pressure is easy to damage and has short service life, the maintenance cost of the production process is very high, and the normal operation of the production is often influenced, so far, no report about the application of the high-efficiency rotating packed bed reactor to the production of the olefin hydroformylation reaction exists.
Disclosure of Invention
The invention mainly solves the technical problems of low reaction conversion rate and low target product selectivity in the olefin hydroformylation reaction process in the prior art, and provides a method for preparing high-carbon aldehyde by hydroformylation of high-carbon olefin. The method has the advantages of high reaction conversion rate and high selectivity of target products, and has the characteristics of low equipment investment and simple maintenance.
The technical scheme of the invention is as follows:
a method for preparing high carbon aldehyde by hydroformylation of high carbon olefin comprises (1) providing a fiber membrane reactor and a stirred tank reactor, wherein the high carbon olefin and synthesis gas are respectively contacted with a water-soluble olefin hydroformylation catalyst in the fiber membrane reactor and the stirred tank reactor under certain conditions to generate corresponding high carbon aldehyde; (2) unreacted synthesis gas, gas-phase by-products and product aldehyde in the fiber membrane reactor and a catalyst aqueous solution enter a stirred tank reactor from the bottom, and gas phase and liquid phase are separated; (3) cooling the reaction liquid containing the water-soluble olefin hydroformylation catalyst in the stirred tank reactor, sending the reaction liquid to the top of the fiber membrane reactor, and returning part of the reaction liquid to the stirred tank reactor to control the temperature; (4) condensing and cooling unreacted mixed gas and gaseous by-products discharged from the top of the stirred tank reactor, returning unreacted olefin to the stirred tank reactor, and discharging gaseous phase; (5) and the product aldehyde and the catalyst solution overflow from the stirred tank reactor, are cooled and enter a crude aldehyde tank for aldehyde-water separation, the crude aldehyde is subjected to subsequent separation and refining, and the catalyst solution is circulated to the stirred tank reactor to continuously participate in the reaction.
In the technical scheme, a large amount of hydrophilic fiber media are arranged in the fiber membrane reactor. The geometric configuration of the hydrophilic fiber medium is any one or the mixture of any more of filiform shape, reticular shape and cylinder shape with porous wall. The length of the filamentous fiber medium is 0.2-10m, and the diameter is 30-1000 μm; the diameter of the mesh of the reticular fiber medium and the porous cylindrical fiber medium with the wall is 30-1000 μm; the fibrous filler is made of any one or a mixture of any more of 316L stainless steel, ceramic, silicon oxide or carbon materials.
In the above technical scheme, the water-soluble olefin hydroformylation catalyst is a water-soluble rhodium-phosphine complex catalyst, and the concentration of rhodium in the catalyst aqueous solution is 1 × 10-4mol/L to 1X 10-2mol/L。
In the technical scheme, the reaction temperature of the hydroformylation is controlled to be 90-130 ℃, and preferably 120 ℃.
In the technical scheme, the reaction pressure of the hydroformylation is controlled to be 2.0-4.0 MPa, and preferably 2.5 MPa.
In the technical scheme, a plurality of cooled reaction liquids containing the water-soluble olefin hydroformylation catalyst are arranged on the side wall of the fiber membrane reactor at different heights and form a reaction temperature regulating system through inlets.
In the technical scheme, the fiber membrane reactor is connected with the stirred tank reactor through a pipeline or a flange.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
In the drawings:
FIG. 1 shows a schematic diagram of an oxo reaction system according to a preferred embodiment of the present invention.
Wherein the figures include the following reference numerals:
A. a fiber membrane reactor; B. a stirred tank reactor; C. a stirrer; D. an olefin condensation recoverer; E. a product cooler; F. an aldehyde-water separator; G. a catalyst circulation pump; H. a circulating liquid cooler; I. and (4) a circulating liquid pump.
Detailed Description
The present invention is not limited by the following examples, and specific embodiments may be determined according to the technical solutions and practical situations of the present invention.
[ example 1 ]
The rhodium content in the stirred tank reactor B is 1 multiplied by 10-4mol/L to 1X 10-4The method comprises the steps of feeding a part of circulating liquid into a middle part and a lower part of a fiber membrane reactor and a stirring kettle reactor simultaneously with feeding of the mixed gas, controlling the temperature in the reactor, stabilizing the temperature in the reactor at about 120 ℃, feeding a fiber A reactor mixture into a hydroformylation reactor, feeding a crude gas-liquid phase catalyst mixture into a gas-liquid phase reaction kettle B, and feeding the crude gas-liquid phase reaction kettle B into a liquid phase reaction kettle which contains aldehyde and aldehyde, wherein the temperature is 120 ℃, the water solution is pressurized by a circulating pump I, the water solution is cooled to 80 ℃ by a circulating liquid cooler H, the water solution 1 and the water solution 2 are 99% of α -heptene, the water solution 4 and the water solution 5 are synthesis gas with the volume ratio of hydrogen to carbon monoxide = 1:1, the water solution 3 and the water solution 6 are fed into a gas phase distributor at the bottom of the fiber membrane reactor A, the water and the water are fed into a gas phase reactor at the top of the fiber membrane reactor A under the action of a catalyst, the heptene, the hydrogen and the carbon monoxide are subjected to a hydroformylation reaction under the action of the catalyst in the reaction in the reactor A, the reaction kettle, the crude gas phase reaction kettle is fed into the fiber reactor A, the fiber reactor, the crudeAnd (3) cooling the mixed gas and the gas-phase by-products to 10 ℃ through an olefin condensation recoverer D, condensing aldehyde and unreacted olefin carried in the gas phase, returning the condensed aldehyde and unreacted olefin to the stirred tank reactor B, maintaining the system pressure of the gas phase at 2.0MPa through a gas-phase pressure control valve, and feeding the gas phase into a fuel pipe network or a recovery facility. The reaction liquid is cooled to 40 ℃ from an overflow pipe of the stirring kettle reactor B through a product cooler E, enters an aldehyde-water separator F, oil and water are quickly layered, a water phase containing the catalyst is sent to an outlet of a circulating liquid pump I through a catalyst circulating pump G, and the octyl aldehyde generated by the reaction is discharged from the upper part of the aldehyde-water separator F and enters subsequent separation and purification.
The flow rate of the circulating liquid in the reaction tube is controlled to be 0.5m/s, the gas-liquid ratio of the mixed gas entering the fiber membrane reactor A and the circulating liquid is 280, the conversion rate of the reaction is 90.5 percent, and the selectivity is 97 percent.
[ example 2 ]
The rhodium content in the stirred tank reactor B is 1 multiplied by 10-4mol/L to 1X 10-4The method comprises the steps of feeding a mixed gas into a reactor A, allowing heptene, hydrogen and carbon monoxide to perform hydroformylation reaction under the action of a catalyst in the reactor A, feeding part of a circulating liquid into the reactor B, allowing part of the circulating liquid to return to the middle and the lower part of a fiber, allowing a gas phase mixture containing a catalyst B in the reactor B to enter a stirred tank reactor B, allowing a gas phase mixture containing olefin and aldehyde to quickly return to the reactor B, allowing the gas phase mixture containing olefin and aldehyde to pass through a stirred tank reactor B, allowing the gas phase mixture to quickly return to a stirred tank reactor B, allowing the gas phase mixture to pass through a gas phase condensation reactor B, allowing the gas phase mixture to quickly pass through a gas phase condensation reactor B, allowing the gas phase condensation reactor B to enter a stirred tank reactor B, and a gas phase condensation aldehyde recovery device B to quickly pass through a circulating liquid phase condensation reactor B, and a gas phase condensation reactor B, and introducing the gas phase condensation aldehyde recovery device, and recovering deviceThe pressure of the system is maintained at 2.0MPa, and the gas phase is sent to a fuel pipe network or a recovery facility. The reaction liquid is cooled to 40 ℃ from an overflow pipe of the stirring kettle reactor B through a product cooler E, enters an aldehyde-water separator F, oil and water are quickly layered, a water phase containing the catalyst is sent to an outlet of a circulating liquid pump I through a catalyst circulating pump G, and the octyl aldehyde generated by the reaction is discharged from the upper part of the aldehyde-water separator F and enters subsequent separation and purification.
The flow rate of the circulating liquid in the reaction tube is controlled to be 0.5m/s, the gas-liquid ratio of the mixed gas entering the fiber membrane reactor A and the circulating liquid is 250, the conversion rate of the reaction is 73.5 percent, and the selectivity is 98 percent.
[ example 3 ]
The rhodium content in the stirred tank reactor B is 1 multiplied by 10-4mol/L to 1X 10-4The method comprises the steps of feeding a mixture of heptane, hydrogen and carbon monoxide into a hydrogen hydroformylation reaction reactor, feeding part of a circulating liquid into the middle and the lower part of a fiber membrane reactor, controlling the temperature in the reactor, stabilizing the temperature at about 130 ℃, feeding a mixture of rhodium-phosphine complex catalyst (supplied by Sichuan university) in a water solution at 130 ℃, pressurizing the mixture by a circulating pump I, cooling the mixture to 90 ℃ by a circulating liquid cooler H, feeding the mixture into a top liquid distributor of the fiber membrane reactor A, feeding the mixture of α -nonene with 99% of stream 1 and stream 2, feeding the mixture of α -nonene with the volume ratio of hydrogen to carbon monoxide = 1:1 in stream 4 and stream 5, feeding the mixture of α -nonene with the volume ratio of hydrogen to carbon monoxide = 1.10 in stream 3 and stream 6, feeding the mixture of stream 3 into a bottom gas phase distributor of a stirred tank reactor A, feeding the mixture of α -nonene into a top gas distributor of the fiber membrane reactor A under the action of catalyst, feeding the mixture of heptene, hydrogen and carbon monoxide into a hydroformylation reaction under the action of the catalyst in the reactor, feeding part of the circulating liquid phase mixture of the circulating liquid phase into the fiber membrane reactor, feeding the gas phase reactor B, feeding the mixture of the stirred tank, feeding the mixture of a gas phase reactor B, feeding the mixture of a condensed water-aldehyde condensate recovery system, feeding the mixture of the condensed oil recovery system of the stirred phase reactor B, cooling system, feeding the condensed oil recovery system of the condensed oil recovery systemAnd (3) quickly layering, conveying the catalyst-containing water phase to an outlet of a circulating liquid pump I through a catalyst circulating pump G, and allowing the octanal generated by the reaction to partially flow out of an aldehyde-water separator F and enter subsequent separation and purification.
The flow rate of the circulating liquid in the reaction tube is controlled to be 0.5m/s, the gas-liquid ratio of the mixed gas entering the fiber membrane reactor A and the circulating liquid is 300, the conversion rate of the reaction is 90.5 percent, and the selectivity is 97.5 percent.
Claims (6)
1. A method for preparing high carbon aldehyde by hydroformylation of high carbon olefin comprises the following process steps:
(1) high-carbon olefin and synthesis gas are contacted with a water-soluble olefin hydroformylation catalyst in a fiber membrane reactor and a stirred tank reactor at the temperature of 90-130 ℃ and the pressure of 2-4 MPa to generate high-carbon aldehyde;
(2) unreacted synthesis gas, gas-phase by-products and product aldehyde in the fiber membrane reactor and a water-soluble olefin hydroformylation catalyst enter a stirred tank reactor, and gas phase and liquid phase are separated at the upper part of the stirred tank reactor;
(3) most of the reaction liquid containing the water-soluble olefin hydroformylation catalyst in the stirred tank reactor is cooled and sent to the top of the fiber membrane reactor, and the rest reaction liquid returns to the fiber membrane reactor and the stirred tank reactor to control the reaction temperature;
(4) condensing and cooling the mixed gas and the gaseous by-product discharged from the top of the stirred tank reactor, returning the unreacted high-carbon olefin to the stirred tank reactor, and discharging the gaseous phase;
(5) and (3) overflowing the product aldehyde and the water-soluble olefin hydroformylation catalyst from the stirred tank reactor, cooling the product aldehyde and the water-soluble olefin hydroformylation catalyst, allowing the product aldehyde and the water-soluble olefin hydroformylation catalyst to enter a crude aldehyde tank for aldehyde water separation, subsequently separating and refining the crude aldehyde, and circulating the catalyst solution to the stirred tank reactor to continuously participate in the reaction.
2. The method for preparing high carbon aldehyde by hydroformylation of high carbon olefin according to claim 1, wherein: the high-carbon olefin is an olefin with 5-12 carbon atoms.
3. The homocarbene according to claim 1A process for the hydroformylation of hydrocarbons to produce higher aldehydes, characterised in that: the product gas phase stream in step (2) comprises: h2CO, unreacted higher olefins, alkanes, product aldehydes and inert components.
4. The method for preparing high carbon aldehyde by hydroformylation of high carbon olefin according to claim 1, wherein: and (3) controlling the cooling temperature to be 40-100 ℃ and controlling the reaction temperature of the fiber membrane reactor and the stirred tank reactor to be 90-130 ℃.
5. The method for preparing high carbon aldehyde by hydroformylation of high carbon olefin according to claim 1, wherein: and (4) the condensation cooling temperature in the step (4) is-10-50 ℃.
6. The method for preparing high carbon aldehyde by hydroformylation of high carbon olefin according to claim 1, wherein: and (3) separating the product aldehyde from the water-soluble olefin hydroformylation catalyst in the step (5) by adopting standing liquid-liquid layering or centrifugation.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112479841A (en) * | 2020-11-26 | 2021-03-12 | 万华化学集团股份有限公司 | Process for synthesizing butyraldehyde by hydroformylation of propylene |
| CN113372206A (en) * | 2021-05-12 | 2021-09-10 | 上海簇睿低碳能源技术有限公司 | Method for synthesizing high-carbon aldehyde by using microchannel reaction device |
| CN113735695A (en) * | 2021-10-11 | 2021-12-03 | 青岛三力本诺新材料股份有限公司 | Method for preparing high-carbon aldehyde by adopting high-carbon olefin and production device thereof |
| CN114874083A (en) * | 2022-05-31 | 2022-08-09 | 上海华谊（集团）公司 | Olefin hydroformylation method and system |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5648553A (en) * | 1994-12-09 | 1997-07-15 | Mitsubishi Chemical Corporation | Method for producing aldehydes |
| JP2001316320A (en) * | 2000-05-01 | 2001-11-13 | Mitsubishi Chemicals Corp | Method for producing aldehyde compounds |
| CN101575272A (en) * | 2009-06-16 | 2009-11-11 | 南京荣欣化工有限公司 | Process for continuously producing corresponding aldehyde by alkene hydroformylation reaction |
| CN102649718A (en) * | 2011-02-25 | 2012-08-29 | 中国石油化工股份有限公司 | Olefin hydroformylation method |
| CN102826970A (en) * | 2011-06-17 | 2012-12-19 | 中国石油化工股份有限公司 | Two-stage reaction method and device of hydroformylation of low-carbon alkene |
| CN102826972A (en) * | 2011-06-17 | 2012-12-19 | 中国石油化工股份有限公司 | Method for preparing aldehydes though hydroformylation of olefins |
-
2019
- 2019-12-31 CN CN201911424545.4A patent/CN111153782A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5648553A (en) * | 1994-12-09 | 1997-07-15 | Mitsubishi Chemical Corporation | Method for producing aldehydes |
| JP2001316320A (en) * | 2000-05-01 | 2001-11-13 | Mitsubishi Chemicals Corp | Method for producing aldehyde compounds |
| CN101575272A (en) * | 2009-06-16 | 2009-11-11 | 南京荣欣化工有限公司 | Process for continuously producing corresponding aldehyde by alkene hydroformylation reaction |
| CN102649718A (en) * | 2011-02-25 | 2012-08-29 | 中国石油化工股份有限公司 | Olefin hydroformylation method |
| CN102826970A (en) * | 2011-06-17 | 2012-12-19 | 中国石油化工股份有限公司 | Two-stage reaction method and device of hydroformylation of low-carbon alkene |
| CN102826972A (en) * | 2011-06-17 | 2012-12-19 | 中国石油化工股份有限公司 | Method for preparing aldehydes though hydroformylation of olefins |
Non-Patent Citations (1)
| Title |
|---|
| 王同恩等: "混合C_8烯烃氢甲酰化反应的实验研究", 《煤化工》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112479841A (en) * | 2020-11-26 | 2021-03-12 | 万华化学集团股份有限公司 | Process for synthesizing butyraldehyde by hydroformylation of propylene |
| CN113372206A (en) * | 2021-05-12 | 2021-09-10 | 上海簇睿低碳能源技术有限公司 | Method for synthesizing high-carbon aldehyde by using microchannel reaction device |
| CN113735695A (en) * | 2021-10-11 | 2021-12-03 | 青岛三力本诺新材料股份有限公司 | Method for preparing high-carbon aldehyde by adopting high-carbon olefin and production device thereof |
| CN114874083A (en) * | 2022-05-31 | 2022-08-09 | 上海华谊（集团）公司 | Olefin hydroformylation method and system |
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