KR101457734B1 - An apparatus for separation of a catalyst for the hydroformylation of olefin, and a method for separation using thereof - Google Patents
An apparatus for separation of a catalyst for the hydroformylation of olefin, and a method for separation using thereof Download PDFInfo
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Abstract
The present invention relates to an apparatus for separating a catalyst for hydroformylation of olefins and a method for separating the catalyst using hydroformylation of olefins, the apparatus comprising: A reactant inlet formed in a side wall of the reactor and connected to a lower pipe of the hydroformylation reactor and having a spray nozzle for spraying the hydroformylation reaction liquid at a high speed, And a liquid discharge outlet formed at a lower side of the reactor for discharging a low boiling point component of the reactants in the catalyst separation reactor and a liquid discharge outlet for discharging a high boiling point component of the reactants in the catalyst separation reactor And a separation method using the same.
According to the present invention, it is possible to separate the catalyst from the product formed by the hydroformylation reaction and the unreacted raw material, etc., but energy-efficient separation can be achieved while reducing catalyst deactivation without using a vaporizer.
Description
The present invention relates to an apparatus for separating an olefin from a hydroformylation catalyst and a separation method using the same, and more particularly, to a catalyst for separating olefins from a hydroformylation catalyst, The present invention relates to a separation apparatus of a catalyst for hydroformylation of an olefin and a separation method using the same.
A hydroformylation reaction, commonly known as an oxo (OXO) reaction, involves the reaction of various olefins with a synthesis gas (CO / H 2 ) in the presence of a metal catalyst and a ligand, linear, normal, branched and iso aldehyde are produced. The oxo reaction was first discovered by Otto Roelen in Germany in 1938 and around 8.4 million tons of various aldehydes (including alcohol derivatives) are produced and consumed worldwide through the oxo process in 2001 ( SRI report , November 2002 , 682 , 700A).
Various aldehydes synthesized by oxo reaction are converted to aldehyde derivatives, acid and alcohol, through oxidation or reduction processes. In addition, it may be transformed into various acids and alcohols containing long alkyl groups through oxidation or reduction reaction after condensation reaction such as Aldol. These alcohols and acids are used as raw materials for solvents, additives, and various plasticizers.
As a typical example of hydroformylation, propylene is introduced into an oxo reactor using a catalyst together with syngas (CO / H 2 ) to produce n-butylaldehyde and iso-butylaldehyde. The resulting aldehyde mixture is sent to the separation system together with the catalyst mixture to separate into hydrocarbon and catalyst mixture, then the catalyst mixture is circulated to the reactor and the hydrocarbon component is transferred to the stripper. The stripper's hydrocarbons are stripped by the freshly supplied syngas so that unreacted propylene and syngas are recovered in the oxo reactor and the butylaldehyde is transferred to the column and separated into normal and iso-butylaldehyde, respectively.
The hydroformylation reaction can be carried out continuously, semicontinuously or batchwise, and a typical hydroformylation process is a gas or liquid recirculation system. It is important that the hydroformylation reaction improves the reaction efficiency by allowing smooth contact of liquid and gaseous starting materials. For this purpose, a continuous stirred tank reactor (CSTR) has been used, which conventionally stirs the liquid and vapor components in the reactor uniformly.
FIG. 1 is a process diagram for performing the hydroformylation process of an olefin using a continuous stirred tank reactor (CSTR), in which a catalyst solution recycling pipe is connected between recycle piping to remove aldehyde from a vaporizer as a catalyst separator, Solution or reactivated catalyst solution into the reactor system. That is, the olefin (for example, propylene) and the synthesis gas are supplied to the nozzles provided on the upper portion of the oxo reactor through which the catalyst solution is loaded, through the olefin supply pipe and the syngas supply pipe, respectively.
In order to increase the efficiency of the gas-liquid reaction, a nozzle is provided inside the oxo reactor, and the supplied olefin and synthesis gas are continuously injected and supplied into the oxo reactor through the nozzles. The olefin and synthesis gas injected into the oxo reactor are subjected to a hydroformylation reaction in the presence of a catalyst to produce a reaction mixture. The reaction mixture includes unconverted olefins, reaction by-products and catalyst solutions in addition to the objective aldehydes (e.g., normal- and iso-butylaldehyde).
The reaction mixture containing the aldehyde is recovered through the recycle line using a circulation pump and then circulated to the reactor via the recycle line. At this time, a portion of the circulating reaction mixture can be led to the catalyst / aldehyde separator through a separate line from the recycle line to separate the aldehyde. That is, it is sent to a separation / recovery device and the like, and can be treated with a conventional distillation device or the like to separate and recover various aldehydes and condensation products. The desired aldehyde is recovered from the reaction mixture and the remaining catalyst mixture is fed to the recycle line of the oxo reactor through the catalyst solution recycle line.
In addition, a heat exchanger may be provided between the recycling lines, but the location thereof is not limited to a specific position on the circulation cycle. Wherein the heat exchanger serves to maintain the reaction mixture recycled to the oxo reactor at a temperature suitable for the hydroformylation reaction conditions.
However, by separating the catalyst through the vaporizer, not only the activity of the catalyst is lowered due to the high heating temperature in the vaporizer, but also the energy requirement is considerable, which is not efficient.
Accordingly, it is an object of the present invention to provide a separation apparatus for replacing a vaporizer in separating a hydroformylation reaction catalyst, thereby reducing the deactivation of the catalyst and separating energy efficiently.
Another object of the present invention is to provide a separation method using the above apparatus.
As a means for solving the above problems, the present invention provides a separation apparatus for olefin hydroformylation reaction catalyst,
An apparatus for separating a catalyst after hydroformylation reaction of an olefin,
The apparatus includes a reactor for performing a catalyst separation reaction, a reaction inlet formed in a sidewall of the reactor and connected to a lower pipe of the hydroformylation reactor and equipped with a spray nozzle for spraying the hydroformylation reaction solution at a high speed, A gas phase discharge outlet formed on the upper side of the reactor for discharging a low boiling point component of the reactants in the catalyst separation reactor and a liquid phase outlet for discharging a high boiling point component of the reactants in the catalyst separation reactor, And a discharge outlet.
The olefins usable in the present invention are not limited thereto, but olefins having 2 to 20 carbon atoms can be used. More specifically, olefins such as ethylene, propylene, 1-butene, 1-hexene, Hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 2-butene, 1-octadecene, 2-hexene, 2-hexene, 2-octene, styrene, 3-phenyl-1-propene or 4-isopropylstyrene, , 1-butene, 2-butene or 1-octene.
Suitable catalysts suitable for use in the present invention include, but are not limited to, cobalt (Co) and rhodium (Rh) systems currently used in the oxo process, and the hetero- As used in the milling reaction, it may include a metal-carbonyl complex catalyst and a ligand.
The metal-carbonyl complex catalyst can be used without limitation as long as it is commonly used in the art. Examples of the catalyst include cobalt (Co), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os) A catalyst containing a transition metal such as palladium (Pt), palladium (Pd), iron (Fe), or nickel (Ni) as a central metal may be used. Specifically, there may be mentioned cobalt carbonyl [Co 2 (CO) 8 ], acetylacetonato dicarbonyl rhodium [Rh (AcAc) (CO) 2 ], acetylacetonato carbonyl triphenylphosphine rhodium [Rh (CO) (TPP) 3 ], acetylacetonatedicarbonyl iridium [Ir (AcAc) (CO) 2 ], and hydrido At least one complex catalyst selected from the group consisting of carbonyl tri (triphenylphosphine) iridium [HIr (CO) (TPP) 3 ] can be used.
The ligand may be a tri-substituted phosphine, a phosphine oxide, an amine, an amide, or an isonitrile, or may be a tri-substituted phosphine, . The tri-substituted phosphines include, but are not limited to, triaryl phosphine, triaryl phosphite, alkyldiaryl phosphine, and more specifically triphenyl phosphine, tritolyl phosphine, triphenyl phosphite, and n -Butyldiphenylphosphine and the like can be used.
The rhodium catalyst is used in most commercialized processes because it provides stable reaction conditions for the hydroformylation process rather than cobalt or iridium catalyst and provides excellent catalytic activity and high selectivity. Is more preferable. Further, it is more preferable to include triphenylphosphine (TPP) as a ligand in view of the activity, stability and cost of the catalyst.
Examples of the solvent that can be used in the catalyst mixture solution include aldehydes such as propanaldehyde, butylaldehyde, pentylaldehyde, and valeraldehyde; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, or cyclohexanone; Alcohols such as ethanol, pentanol, octanol, and pentanol; Aromatic compounds such as benzene, toluene and xylene; Ethers such as tetrahydrofuran, dimethoxyethane and dioxane; And paraffin hydrocarbons such as heptane. Preferably, the aldehyde produced through the hydroformylation reaction from the olefin used as the raw material is used as a raw material. For example, butylaldehyde is used when propylene is a raw material, and pentylaldehyde is used when butylen is a raw material.
The concentration of the catalyst mixture solution is preferably 10 to 2000 ppm in the case of the metal carbonyl complex catalyst, and 1 to 30 wt% in the case of the ligand.
In this case, it is preferable that the injection means in the catalyst separation reactor includes one or more nozzles, in particular, an ejector equipped with a spray nozzle, and the diameter of the unit nozzle is preferably 0.1 to 1000 mm. The contact area of the gas-liquid is widened due to the rapid flow velocity at the nozzle portion, thereby providing a sufficient reaction area.
It is most preferable that 1 to 3 spray nozzles are provided in consideration of the reaction efficiency.
The synthesis gas, which is another starting material of the hydroformylation reaction, is a mixed gas of carbon monoxide and hydrogen. The mixing ratio of CO: H 2 is not limited thereto, but it is preferably 5:95 to 70:30, More preferably 60:40 to 45:55, and most preferably 45:55 to 55:45. The molar ratio of the olefin to the synthesis gas is preferably 95: 5 to 5:95, and more preferably 75:25 to 25:75.
Further, the olefin and the syngas are preferably injected at a pressure of 1 to 200 bar, respectively. The linear velocity of the injected olefin and the syngas is preferably 2 to 50 m / s and more preferably 15 to 20 m / s.
The hydroformylation reaction is preferably carried out at a temperature of 80 to 200 ° C, and more preferably at a temperature of 90 to 150 ° C. Further, the reaction is preferably carried out at a pressure of 5 to 100 bar, more preferably at a pressure of 5 to 50 bar. Further, as the hydroformylation reactor, it is preferable to use a reactor selected from a continuous stirred tank reactor (CSTR) and a venturi loop reactor desirable.
The reaction mixture formed by the hydroformylation reaction includes a synthesis gas, an unreacted reactant, an aldehyde, a catalyst, and the like. The reaction mixture is recycled continuously or intermittently from the reactor to the circulation line via the circulation pump. That is, most of the reaction products are separated from the catalyst through the separation unit, and the hydrogenation reactor or the aldol condensation reactor and the separation distillation column are sequentially passed through, and the separated catalyst is recycled to the hydroformylation reactor.
During the total residence time of the process, the unreacted olefin is recycled during the predetermined number of cycles. The cycle recovery can be selected as desired in the process according to the invention.
Particularly, it is preferable that the catalyst separation reactor is maintained at a normal pressure to 5 bar, more preferably at a normal pressure to 2 bar. That is, at the instant when the reaction liquid is injected at a high speed through the spray nozzle in the catalyst separation reactor under atmospheric pressure, or immediately after, excessively low boiling point components such as aldehyde product, unreacted raw material and syngas are mostly vaporized, The ligand component and a small amount of the aldehyde product remain in a liquid phase.
In this case, the vaporized gas component is discharged through the upper side of the catalyst separation reactor, and the liquid component remaining after being liquefied is discharged through the lower side of the catalyst separation reactor and circulated through the circulation pump to the hydroformylation reactor . The flow rate of the circulating reaction mixture may vary depending on the content of the catalyst solution charged into the reactor, and the flow rate of the reaction mixture circulated per minute is preferably 0.1 to 0.8 times, more preferably 0.2 to 0.5 times, More preferable.
FIG. 2 is a view illustrating the use of the catalyst separating apparatus according to the present invention. FIG. 2 shows various standard items of equipment actually used in factories such as a valve, a temperature measuring device, .
In order to accomplish the above object, the present invention provides a process for separating an olefin from a hydroformylation catalyst, comprising the steps of: hydroformylating an olefin together with a catalyst and a synthesis gas to form a reaction mixture containing aldehyde; Rapidly dispersing the reaction mixture through a spray nozzle in the catalyst separator, and performing a vaporization reaction of the low boiling point component in the reactor; And discharging the low boiling point gas phase component through the reactor upper gas phase exhaust outlet and discharging the remaining high boiling point liquid phase component through the liquid phase outlet outlet on the lower side of the reactor; And a control unit.
Circulating the liquid phase effluent on the lower side of the reactor to the hydroformylation reactor; In view of the reaction efficiency.
The apparatus for separating a catalyst for hydroformylation reaction of olefins according to the present invention and the separation method using the same are characterized in that a catalyst is separated from a product produced by a hydroformylation reaction and an unreacted raw material and further comprises an additional heating / Which is advantageous in that it can be separated in an energy-efficient manner while reducing catalyst deactivation.
1 is a schematic view showing a process of separating a catalyst after hydroformylation reaction of an olefin using a vaporizer according to the prior art.
2 is a schematic view showing a process of separating a catalyst after hydroformylation reaction of an olefin using a catalyst separation apparatus that maintains an atmospheric pressure condition according to an embodiment of the present invention.
Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited by the examples in order to facilitate a specific understanding of the invention.
Example 1 (Example using CSTR)
In this embodiment, the results obtained when the process of separating the catalyst after the hydroformylation reaction of olefin by using the catalyst separating apparatus of FIG. 2 was performed.
First, a hydroformylation reactor was constituted by a 50.0 liter CSTR. Also, as shown in FIG. 2, a catalyst separation reactor was constructed using a reaction chamber having a size of 3.0 liters as a catalyst separating apparatus.
In order to supply the reaction liquid from the lower pipe of the hydroformylation reactor to the catalyst separation reactor, one spray nozzle having a diameter of 0.4 mm was mounted on one side wall of the separation reactor.
1728 g of triphenylphosphine (TPP) and 34.4 g of rhodium triphenylphosphine acetylacetonate carbonyl (ROPAC) were weighed and dissolved in purified n-butylaldehyde to prepare a n-butylaldehyde catalyst solution having a total weight of 27.6 g . The catalyst solution thus prepared was poured into a hydroformylation reactor and the entire system was purged three times with purified nitrogen gas while slowly circulating the catalyst solution at a rate of 0.2 liters per minute by operating the circulation pump.
Propylene is fed at a flow rate of 3.7 kg / hr until the pressure inside the reactor reaches 13 bar. Thereafter, the internal temperature of the reactor was raised to 90 ° C. by using an external circulation heat exchanger, and a syngas (mixed gas having a molar ratio of carbon monoxide and hydrogen of 50:50) was supplied to the reactor at a flow rate of 2.5 kg / hr, . During the reaction, the reaction pressure was maintained at 19 bar and the reaction temperature was kept at 90 ° C. To this end, propylene and syngas were supplied at the equivalent ratio.
In addition, the produced reaction product and the unreacted reactants were injected at high speed through the nozzle of the catalyst separation reactor through the lower side piping of the hydroformylation reactor together with the catalyst solution. At this time, the pressure in the catalyst separation reactor was kept at atmospheric pressure, and the jetting rate in the nozzle injection was in the range of 15 to 20 m / s.
Therefore, the reaction mixtures injected into the catalyst separation reactor were vaporized at the instant of high-speed injection and the low-boiling components (excess BAL product, propylene, syngas, etc.) were vaporized and separated through the gas discharge outlet on the upper side of the reactor.
In addition, the catalyst made of the metal and the small amount of the BAL product were discharged through the liquid discharge outlet on the lower side of the reactor because the vaporization reaction was not caused and the product remained in the liquid state. The resulting liquid effluent was recycled to the hydroformylation reactor to continuously carry out the hydroformylation reaction.
As a result, the amount of butylaldehyde recovered at the upper part of the catalyst separator was 6.1 kg / hr. After 168 hours of reaction, the catalyst was partially recovered to recover the activity, 100% of the catalyst activity was maintained at 70% level.
Example 2 (Use of a Venturi-loop Reactor)
The same experiment as in Example 1 was repeated except that the hydroformylation reactor in Example 1 was replaced with a benzyl-loop reactor.
As a result, the amount of butylaldehyde recovered at the upper part of the catalyst separator was 6.15 kg / hr. After 168 hr of reaction, the catalyst recovered in the liquid phase was partially recovered and the degree of deactivation was measured. 100% of the catalyst activity was maintained at 68% level.
Comparative Example 1 (using vaporizer)
The same experiment as in Example 1 was repeated except that the catalyst was further heated to 118 DEG C using the vaporizer of Fig. 1 instead of the catalyst separator used in Example 1. [
As a result, there was no change in the amount of butylaldehyde produced, but when the initial activity of the reaction was taken as 100%, the catalytic activity was reduced to 48% I could confirm.
Comparative Example 2 (Example 1 in which no nozzle is used)
The same experiment as in Example 1 was repeated, except that the catalyst separation reactor used in Example 1 was not provided with any spray nozzle.
As a result, the amount of butylaldehyde recovered at the upper part of the catalyst separator was as low as 5.0 kg / hr, and the activity of the catalyst solution remained at 65% after 168 hr reaction.
In this condition, there is a limit in separating the reaction product continuously produced from the catalyst solution, and it is confirmed that there is a limit to use additional heating or decompression device in the catalyst separation reactor.
Comparative Example 3 (Example 2 in which no nozzle is used)
The same experiment as in Example 1 was repeated except that the catalyst separation reactor used in Example 1 was heated at 110 캜 to separate the reaction product into a catalyst without any spray nozzle.
As a result, the amount of butylaldehyde recovered at the top of the catalyst separator was 6.1 kg / hr, which is similar to that of Example 1, but the activity of the catalyst solution was reduced to 50% after 168 hr of reaction.
In this condition, there is a limit in separating the reaction product continuously produced from the catalyst solution, and it is confirmed that there is a limit to use additional heating or decompression device in the catalyst separation reactor. As can be seen from the above description, the embodiments according to the method of the present invention require not only a remarkably improved deterioration in catalytic activity as compared with the comparative examples but also an additional heating or decompression device for separating the catalyst. It can be confirmed that it is improved.
Claims (18)
The apparatus comprises a catalyst separation reactor connected to the hydroformylation reactor of olefin and performing a catalyst separation reaction,
A reactant inlet formed in a side wall of the reactor and connected to a lower pipe of the hydroformylation reactor and having a spray nozzle for spraying the hydroformylation reaction liquid at a high speed,
A vapor discharge outlet formed on the upper side of the reactor for discharging a low boiling point component of the reactants in the catalyst separation reactor,
And a liquid discharge outlet formed in the lower side of the reactor for discharging a high boiling point component of the reactants in the catalyst separation reactor, wherein the pressure in the catalyst separation reactor is maintained in the range of atmospheric pressure to 5 bar. Separation device for hydroformylation reaction catalyst.
The olefin may be at least one selected from the group consisting of ethylene, propylene, 1-butene, 1-hexene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-tridecene, Butene, 2-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 2-butene, 2-methylpropene, -Hexene-octene, styrene, 3-phenyl-1-propene or 4-isopropylstyrene.
As the catalyst separation reactor, there may be used a continuous-type reactor (CSTR) or a venturi loop reactor Characterized in that the olefin hydroformylation reaction catalyst is separated.
Wherein the low boiling point gas component discharged from the upper side of the catalyst separation reactor is unreacted olefin, syngas, and an excessive amount of aldehyde product.
Wherein the high boiling point liquid component discharged from the lower side of the catalyst separation reactor is a catalyst and a small amount of an aldehyde product.
Wherein the high-speed injection line speed through the spray nozzle is in the range of 2 to 50 m / s.
Wherein the spray nozzle is provided with 1 to 3 spray nozzles.
Wherein the liquid phase effluent is connected to the circulation pipe to be circulated to the olefin hydroformylation reactor by a circulation pump.
Rapidly dispersing the reaction mixture through a spray nozzle in the catalyst separation apparatus of claim 1 into the catalyst separation reactor having a pressure within a range of atmospheric pressure to 5 bar and performing a vaporization reaction of a low boiling point component in the reactor; And
Discharging the low boiling point vapor component through the reactor upper vapor phase discharge outlet and discharging the remaining high boiling point liquid component through the liquid phase outlet outlet on the lower side of the reactor; ≪ / RTI > wherein the olefin is reacted with an olefin.
The olefin may be at least one selected from the group consisting of ethylene, propylene, 1-butene, 1-hexene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-tridecene, Butene, 2-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 2-butene, 2-methylpropene, Olefins selected from the group consisting of octene, styrene, 3-phenyl-1-propene or 4-isopropylstyrene.
Wherein the reaction in the hydroformylation reactor is carried out at a temperature of from 80 to 200 DEG C and a pressure of from 5 to 100 bar.
As the catalyst separation reactor, there may be used a continuous stirred tank reactor (CSTR) or a venturi loop reactor ≪ / RTI > wherein the catalyst is a hydroformylation catalyst.
Wherein the low boiling point gas phase component discharged from the upper side of the catalyst separation reactor is an unreacted olefin, a syngas, and an excessive amount of an aldehyde product.
Wherein the high boiling point liquid component discharged from the lower side of the catalyst separation reactor is a catalyst and a small amount of an aldehyde product.
Wherein the high-speed injection line speed through the spray nozzle is in the range of 2 to 50 m / s.
Circulating the reactor bottom liquid effluent to the hydroformylation reactor; Wherein the olefin is present in an amount of from about 1% to about 50% by weight.
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| JP2000034252A (en) * | 1998-07-17 | 2000-02-02 | Mitsubishi Chemicals Corp | Production of aldehyde |
| KR20100058713A (en) * | 2008-11-25 | 2010-06-04 | 주식회사 엘지화학 | Reactor for the hydroformylation of olefin and method for the hydroformylation using the same |
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| JP2000034252A (en) * | 1998-07-17 | 2000-02-02 | Mitsubishi Chemicals Corp | Production of aldehyde |
| KR20100058713A (en) * | 2008-11-25 | 2010-06-04 | 주식회사 엘지화학 | Reactor for the hydroformylation of olefin and method for the hydroformylation using the same |
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