KR101338646B1 - A process for production of aldehyde having high yield from olefin - Google Patents
A process for production of aldehyde having high yield from olefin Download PDFInfo
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Abstract
The present invention relates to a method for preparing aldehyde from olefins, specifically, after pretreatment in which a olefin is charged after high-pressure in the presence of a compound of a metal element belonging to groups 8 to 10 of the periodic table and an organophosphorus compound in the reactor. After supplying the synthesis gas of olefin, hydrogen, and carbon monoxide to the reactor and reacting, the effluent containing the aldehyde and the low-boiling compound was separated by the aldehyde / catalyst solution separation device from the reaction products obtained, and the groups 8 to 10 The aldehyde is simply produced in high yield by extracting the compound of the belonging metal element and the organic phosphorus compound-containing lower liquid, respectively.
Description
The present invention relates to a process for producing aldehydes from olefins, and more particularly to a process for producing aldehydes from olefins in high yield quickly and simply.
The method for producing aldehydes by reacting an olefinic compound with hydrogen and carbon monoxide in the presence of a catalyst consisting of a transition metal belonging to
The linear aldehyde obtained in this manner is usually an alcohol by a hydrogenation reaction, or a hydrogenated reaction after conversion of an aldehyde having a high molecular weight by a condensation reaction, and then converted into an alcohol having a higher molecular weight, thereby producing a raw material, an adhesive or a coating material of a plasticizer. It is used for the raw material of.
On the other hand, the hydroformylation reaction is important to improve the reaction efficiency by allowing the starting materials consisting of the liquid phase and the gas phase to be in smooth contact. To this end, conventionally, a continuous stirred tank reactor (CSTR) is used to stir the liquid and gaseous components evenly in the reactor. Alternatively, a loop type reactor may be used to replace agitation through circulation. However, the above methods have a limitation in increasing the efficiency of the hydroformylation reaction, and have a problem in that a satisfactory aldehyde product cannot be obtained.
Accordingly, it is an object of the present invention to provide a simple and high yield method for preparing aldehydes by reacting olefins with hydrogen and carbon monoxide in the presence of a catalyst.
In order to solve the above problems, a method for producing an aldehyde from the olefin of the present invention,
A pretreatment step of waiting for the olefin after high-pressure filling in the presence of a compound of a metal element and an organophosphorus compound belonging to
A hydroformylation reaction step of supplying a synthesis gas of olefin, hydrogen and carbon monoxide to the reactor and reacting the reaction; And
Extracting an aldehyde and a low boiling point compound containing upper effluent, a compound of a metal element belonging to
Hereinafter, the present invention will be described in detail.
In the present invention, the reactor is pretreated with olefins (high pressure filling and then atmosphere) in the presence of compounds of metal elements and organophosphorus compounds belonging to
In the present invention, the reaction may be performed using a venturi-loop reactor or the like as well as the continuous stirred reactor (CSTR) shown in FIG. 1. In other words, any reactor can be pre-treated with olefins (high pressure after filling), and the reaction can be carried out without limiting the specific reactor. It has such an advantage.
In addition, in the pretreatment with the olefin, when the reaction is performed at 80 to 100 ° C., the reaction is preferably performed at a maximum of 39 bar, specifically, at a pressure of 20 to 30 bar. This can be seen from the point that the relative productivity (%) is directly proportional to the higher the reaction pressure, as is clear in the following examples (see the graph of Figure 2). In this case, relative productivity (%) is n per unit time and unit catalyst weight (volume) under specific conditions when the production of n-butyl aldehyde (BAL) per unit time and unit catalyst weight (volume) under reference conditions is 100. -Means the ratio of the relative production of butyl aldehyde (BAL).
In this way, the reactor filled with olefin at a pressure of up to 39 bar was allowed to stand at 20 to 40 minutes under 80 to 100 ° C. in the presence of a compound of metal elements and organophosphorus compounds belonging to
These reaction products are subjected to an aldehyde / catalyst solution separator as a post-process to extract an upper effluent containing an aldehyde and a low boiling point compound from the top of the separator, and from the bottom of the separator to
In one embodiment of the present invention, a method for producing an aldehyde from an olefin is a compound of a metal element belonging to
Examples of preferred olefins for use in the present invention include ethylene, propylene, 1-butene, 1-hexene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 2-butene, 2-methylpropene, 2-pentene, 2-hexene, 2- Heptene, 2-ethylhexene, 2-octene, styrene, 3-phenyl-1-propene, 1,4-hexadiene, 1,7-octadiene, 3-cyclohexyl-1-butene, allyl acetate, allylbutyl Rate, methyl methacrylate, vinyl methyl ether, vinyl ethyl ether, allyl ethyl ether, n-propyl-7-octenoate, 3-butenenitrile, 5-hexenamide, 4-methylstyrene, 4-isopropylstyrene, etc. Can be mentioned.
As described above, pretreatment of the inside of the reactor with olefin (atmospheric pressure after filling) is preferable because it can improve relative productivity, as described in the following examples. In addition, said "the compound of the metal element and organophosphorus compound which belong to the 8th group-10th group of a periodic table" correspond to the catalyst used for this embodiment.
Looking at the catalyst used in the present invention, the metal compound used in the present embodiment is in the group consisting of metal elements belonging to
Specific examples of such metal compounds include iron compounds, ruthenium compounds, osmium compounds, cobalt compounds, rhodium compounds, iridium compounds, nickel compounds, palladium compounds, platinum compounds and the like. Among these, ruthenium compound, rhodium compound, iridium compound, nickel compound, palladium compound and platinum compound are preferable, and a rhodium compound is especially preferable.
Although the kind of these metal compounds is arbitrary, for example, acetate, acetylacetonate compound, halide, sulfate, nitrate, organic salt, inorganic salt, alkene coordination compound, amine coordination compound, pyridine coordination compound, carbon monoxide of the transition metal Coordination compound, phosphine coordination compound, phosphite coordination compound, etc. are mentioned, It is preferable to use an alkyl phosphine especially.
Hereinafter, the specific example of a metal compound is listed. Examples of the iron compound include Fe (OAc) 2 , Fe (acac) 3 , FeCl 2 , Fe (NO 3 ) 3 , and the like. Examples of the ruthenium compound include RuCl 3 , Ru (OAc) 3 , Ru (acac) 3 , RuCl 2 (PPh 3 ) 3 , and the like. Examples of osmium compounds include OsCl 3 , Os (OAc) 3 , and the like. Examples of the cobalt compound include Co (OAc) 2 , Co (acac) 2 , CoBr 2 , Co (NO 3 ) 2 , and the like. Examples of the rhodium compound include RhCl 3 , RhI 3 , Rh (NO 3 ) 3 , Rh (OAc) 3 , RhCl (CO) (PPh 3 ) 2 , RhH (CO) (PPh 3 ) 3 , RhCl (PPh 3 ) 3 , Rh (acac) 3 , Rh (acac) (CO) 2 , Rh (acac) (cod), [Rh (OAc) 2 ] 2 , [Rh (OAc) (cod)] 2 , [RhCl (CO)] 2 , [RhCl (cod)] 2 , [Rh 4 (CO) 12 ], and the like. Examples of the iridium compound include IrCl 3 , Ir (OAc) 3 , and [IrCl (cod)] 2 . Examples of the nickel compound include NiCl 2 , NiBr 2 , Ni (NO 3 ) 2 , NiSO 4 , Ni (cod) 2 , and NiCl 2 (PPh 3 ) 3 . As the palladium compound, PdCl 2 , PdCl 2 (cod), PdCl 2 (PPh 3 ) 2 , Pd (PPh 3 ) 4 , Pd 2 (dba) 3 , K 2 PdCl 4 , PdCl 2 (CH 3 CN) 2 , Pd (NO 3 ) 2 , Pd (OAc) 2 , PdSO 4 , Pd (acac) 2 , and the like. Examples of the platinum compound include Pt (acac) 2 , PtCl 2 (cod), PtCl 2 (CH 3 CN) 2 , PtCl 2 (PhCN) 2 , Pt (PPh 3 ) 4 , K 2 PtCl 4 , Na 2 PtCl 6 , H 2 PtCl 6 is mentioned. In the above description, cod is 1,5-cyclooctadiene, dba is dibenzylideneacetone, acac is acetylacetonate, Ac is an acetyl group, and Ph group represents a phenyl group, respectively. The kind of metal compound mentioned above is not restrict | limited, Any of a monomer, a dimer, and / or a multimer can be used if it is an active metal complex paper.
The amount of the metal compound used is not particularly limited, but from the viewpoint of the catalytic activity and economical efficiency, the metal compound concentration in the reaction medium is usually 0.1 ppm or more, preferably 1 ppm or more, more preferably 10 ppm or more, and usually 10,000 ppm or less, preferably 1,000 ppm or less, more preferably 500 ppm or less.
Subsequently, when looking at an organophosphorus compound, the phosphine or phosphite etc. which have the capability as a monodentate ligand or a multidentate ligand are used for this organophosphorus compound.
The organic phosphine compound (Hereinafter, it may be described as "single phosphine") which has the capability as a single seat ligand used by this embodiment is represented by the following general formula. In particular, in order to sufficiently exhibit the catalytic activity, the organic phosphine compound is preferably dissolved under the reaction conditions, and the molecular weight thereof is usually 1,500 or less, preferably 1,000 or less, and more preferably 800 or less.
Specific examples of the organic phosphine compound include triphenylphosphine, tri-o-tolylphosphine, 1-naphthyldiphenylphosphine, 4-methoxyphenyldiphenylphosphine and tris (2,4,6-trimeth Triaryl type single seat phosphines, such as a methoxyphenyl) phosphine, a tris (3, 5- diphenylphenyl) phosphine, and 4-dimethylaminophenyl di-2- naphthyl phosphine; Diphenyl-n-propylphosphine, n-octadecyldiphenylphosphine, di (3-t-butyl-2-naphthyl) methylphosphine, isopropyl-2-naphthyl-p-tolylphosphine, 2 Single seat phosphine of the diaryl monoalkyl type, such as ethylhexyldi (4-fluorophenyl) phosphine; Dimethylphenylphosphine, diethyl-4-methoxyphenylphosphine, di-n-octylphenylphosphine, tert-butyl-n-octyl-3,5-dimethylphenylphosphine, diisopropyl- Monoaryldialkyl type single-dented phosphines such as 2-naphthylphosphine and isobutyl-n-pentyl-4-acetylphenylphosphine; Trimethylphosphine, triethylphosphine, tri-n-propylphosphine, tri-n-butylphosphine, tri-n-octylphosphine, tri-n-octadecylphosphine, n-octadecyldimethylphosphine, Diethyl-n-octylphosphine, ethylmethyl-n-propylphosphine, tri-2-ethoxyethylphosphine, isobutyl neopentyl-n-hexylphosphine, tri-2-ethylhexylphosphine, tribenzyl Phosphine, trineopentylphosphine, triisopropylphosphine, tri-t-butylphosphine, tri-2-butylphosphine, di-n-hexyl-1,1-dimethylpropylphosphine, 3-phenylpropyl Single alkyl phosphine of trialkyl type, such as di-t- butylphosphine and 2-butyl- n-propyl-3, 3- dimethoxypropyl phosphine, is mentioned.
Among the above specific examples, as the most preferable single-site phosphine, trimethylphosphine, triethylphosphine, tri-n-propylphosphine, tri-n-butylphosphine, tri-n-octylphosphine, tri-n- Octadecylphosphine, n-octadecyldimethylphosphine, diethyl-n-octylphosphine, ethylmethyl-n-propylphosphine. As the phosphine compound, phosphine having the ability as a bidentate ligand or a polydentate ligand can also be used. Moreover, you may use combining these organophosphorus compounds in multiple numbers.
By using the compounds of the metal elements of
The organophosphorus compound is usually at least 0.1 mol, preferably at least 1 mol, more preferably at least 2 mol, usually at most 1,000 mol, preferably at most 500 mol, more preferably at most 100 mol per mol of the metal compound. .
At this time, the pretreatment condition of the olefin is preferably filled at a maximum of 39 bar, preferably 20 to 25 bar and then maintained for 20 to 40 minutes when the temperature of the reaction in the reactor is 80 to 100 ℃, if 90 ℃ Filling at about 25 bar and then holding for about 30 minutes is desirable in view of relative productivity.
In addition, after the pretreatment process, the olefin is supplied to the reactor together with the synthesis gas, and the molar ratio of olefin: synthesis gas supplied to the reactor is 95: 5 to 5:95, preferably 75:25 to 25:75. .
In particular, the synthesis gas is a mixed gas of carbon monoxide and hydrogen, the mixing molar ratio of CO: H 2 is not limited thereto, but is preferably 5:95 to 70:30, more preferably 40:60 to 60:40. Most preferred is 50:50.
In addition, the olefin and the synthesis gas is preferably injected at a pressure of 5 to 200 bar, respectively. In addition, the linear velocity of the olefin and the synthesis gas is preferably 5 to 40 m / s.
The hydroformylation reaction according to the present invention is carried out at a temperature of 50 to 200 ℃, preferably 50 to 150 ℃, pressure is 5 to 100 bar, preferably 5 to 50 bar, most preferably the temperature is elevated in the pretreatment step Performing the reaction while maintaining the temperature is efficient in terms of reaction efficiency and economy.
Next, the reaction conditions to which the present embodiment is applied will be described in detail.
The reaction pressure formed by the sum of the vapor partial pressures of hydrogen partial pressure, carbon monoxide partial pressure, raw materials, products, and solvents is usually 10 bar or more, preferably 44 bar or less, and more preferably about 15 bar or more and 35 bar or less. If the reaction pressure is excessively low, the metal compound may be inactivated and metallized, and the catalyst activity itself is not sufficiently expressed, and the aldehyde yield is lowered, which is not preferable. In addition, when the reaction pressure is excessively high, the linear selectivity of the aldehyde obtained tends to be lowered, which is also undesirable, and it is difficult to proceed smoothly. In particular, in the present invention, since the reaction rate is sufficiently increased due to pretreatment of the olefin, there is no need to perform the reaction under excessively hard conditions.
In addition, the hydrogen fraction is suitably 2 to 40%, preferably 5 to 30%. If the hydrogen fraction is excessively low, the lowering of the reaction activity is feared, if too high, the selectivity of the raw olefin compound may be lowered.
In addition, the carbon monoxide fraction is appropriate in the gas phase fraction of 0.1 to 30%, preferably 2 to 20%. If the carbon monoxide fraction is too low, the lowering of the reaction activity, in particular metallization of the metal compound is feared, and if the carbon monoxide fraction is excessively high, a decrease in the linear selectivity of the aldehyde obtained is expected.
The reaction temperature in the present invention is usually 25 ° C or higher, preferably 50 ° C or higher, more preferably 70 ° C or higher, and usually 300 ° C or lower, preferably 250 ° C or lower, and more preferably 150 ° C or lower. If the reaction temperature is excessively low, it is expected that the reaction activity itself is not sufficiently obtained. If the reaction temperature is excessively high, a decrease in the linear selectivity of the obtained aldehyde, loss due to thermal decomposition of the ligand, and the like are expected. If the reaction temperature is excessively low, it is expected that the reaction activity itself is not sufficiently obtained. If the reaction temperature is excessively high, a decrease in the linear selectivity of the obtained aldehyde, loss due to thermal decomposition of the ligand, and the like are expected.
Next, the reaction flow in this embodiment is demonstrated in detail with reference to FIG. 1 provided with the continuous stirred reactor (CSTR) 1 and the aldehyde /
First, the catalyst solution is supplied at a separate line (not shown) as necessary or subjected to a high pressure treatment up to 39 bar while injecting olefin, which is a kind of raw material, by line 2 into the
Subsequently, the raw material olefin, hydrogen and carbon monoxide are fed to the
Next, the reaction liquid containing an unreacted raw material is taken out from the
In the aldehyde /
Preferably, by distillation in the aldehyde /
In addition, by the
According to the process described above, aldehydes can be obtained in high yield and in a quick and simple manner.
BRIEF DESCRIPTION OF THE DRAWINGS It is a figure explaining a reaction flow in the case of using a continuous stirred reactor (CSTR) in this embodiment.
FIG. 2 is a graph showing the relative productivity of propylene for each pretreatment pressure in this embodiment, calculated in%.
The following Examples and Comparative Examples do not separately supply olefins in syngas supply so that the reaction rate can be measured. A reaction scheme of a method of using olefins introduced during pretreatment as a raw material is presented, and the present invention is not limited thereto.
Example
1 (
In the process of Fig. 1, 800 g of purified n-butyl aldehyde was dissolved in 48 g of triphenylphosphine (TPP) and 0.8 g of rhodium triphenylphosphine acetylacetonatecarbonyl (ROPAC) to dissolve n-butyl aldehyde catalyst. The solution was prepared.
The catalyst solution thus prepared was previously charged from a separate line (not shown) into the 3-liter CSTR reactor (1), and the heat medium oil flowed to the outer jacket while stirring at a speed of 200 RPM to bring the temperature inside the reactor to 90 ° C. It heated up and kept. When the temperature stabilized at 90 ° C propylene was supplied until reaching 25 bar and then waited for 30 minutes at a temperature of 90 ° C.
Raise the stirrer to 700 RPM and open the valve into the reactor to open syngas (mixture with 50:50 mole ratio of carbon monoxide and hydrogen) and propylene (molar ratio of propylene: synthesis gas is in the range of 95: 5 to 5:95). Started to feed. The flow rate of the syngas supplied to the
Example 2 (pretreatment pressure 23 bar )
In the process of Example 1, the same process was repeated except that the pretreatment pressure of propylene was reduced to 23 bar, the resulting butyl aldehyde was 494 g and the maximum consumption rate of the syngas was 4.7 liters per minute.
Example 3 (pretreatment pressure 21 bar )
The same process was repeated except that the pretreatment pressure of propylene was reduced to 21 bar in Example 1, the resulting butyl aldehyde weight was 478 g and the maximum consumption rate of syngas was 4.6 liters per minute.
The relative productivity of each of the propylene pretreatment pressures of Examples 1 to 3 is calculated as a graph in FIG. 2. As shown in Figure 2, the relative productivity (%) was found to increase proportionally with the pretreatment pressure of propylene.
Comparative Example (Without propylene pretreatment)
As in Example 1, ROPAC catalyst solution having the same composition and weight was prepared, charged to the same reactor, and then filled with propylene up to 18 bar, and no pretreatment of propylene was performed. Subsequently, the same process as in Example 1 was repeated. As a result of measuring the product, the butyl aldehyde weighed 412 g and the maximum consumption rate of the syngas during the reaction was 4.0 liters per minute.
As described above, it was confirmed that the relative productivity is improved up to 150% level by performing a pretreatment process in which the olefin is charged at a high pressure of 18 to 25 bar and then waiting at a specific temperature range.
1 ... Continuous Stirred Reactor (CSTR)
2, 3, 4, 6, 7 ... lines
5. Aldehyde / Catalyst Solution Separator
Claims (14)
Hydroformylation reaction step of supplying olefin and hydrogen and carbon monoxide synthesis gas to the reactor and reacting; And
Extracting an aldehyde and a low boiling point compound containing upper effluent, a compound of a metal element belonging to Groups 8 to 10 and an organophosphorus compound containing lower liquid from the obtained reaction product stream by an aldehyde / catalyst solution separator; It comprises a
Process for preparing aldehydes from olefins.
The pretreatment is characterized in that waiting for 20 to 40 minutes
Process for preparing aldehydes from olefins.
The reactor is characterized in that the continuous stirred reactor or venturi-loop reactor
Process for preparing aldehydes from olefins.
The stirring speed of the reactor during the pretreatment step is characterized in that in the range of 100 to 700 rpm
Process for preparing aldehydes from olefins.
The stirring speed of the reactor during the hydroformylation step is characterized in that in the range of 500 to 1000 rpm
Process for preparing aldehydes from olefins.
The olefins are ethylene, propylene, 1-butene, 1-hexene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexa Decene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 2-butene, 2-methylpropene, 2-pentene, 2-hexene, 2-heptene, 2-ethylhexene, 2 -Octene, styrene, 3-phenyl-1-propene, 1,4-hexadiene, 1,7-octadiene, 3-cyclohexyl-1-butene, allyl acetate, allyl butyrate, methyl methacrylate, vinyl At least one member selected from the group consisting of methyl ether, vinyl ethyl ether, allyl ethyl ether, n-propyl-7-octenoate, 3-butenenitrile, 5-hexenamide, 4-methylstyrene, and 4-isopropylstyrene Characterized
Process for preparing aldehydes from olefins.
The metal element belonging to the group 8 to 10 is at least one selected from the group consisting of ruthenium, rhodium, iridium, nickel, palladium and platinum
Process for preparing aldehydes from olefins.
The organophosphorus compound is characterized in that the phosphine coordination compound or phosphite coordination compound
Process for preparing aldehydes from olefins.
The molar ratio of the olefin and the synthesis gas supplied during the hydroformylation reaction is in the range of 95: 5 to 5:95
Process for preparing aldehydes from olefins.
The molar ratio of carbon monoxide and hydrogen in the synthesis gas is in the range of 5:95 to 70:30
Process for preparing aldehydes from olefins.
The hydroformylation reaction is characterized in that it is carried out at a temperature of 50 to 200 ℃ and a pressure of 5 to 100 bar
Process for preparing aldehydes from olefins.
The hydroformylation reaction is characterized in that to maintain the elevated temperature in the pretreatment step
Process for preparing aldehydes from olefins.
The bottom effluent from the aldehyde / catalyst solution separator is circulated to the reactor
Process for preparing aldehydes from olefins.
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| US11534744B2 (en) | 2016-07-08 | 2022-12-27 | Lg Chem, Ltd. | Composition including hydroformylation catalyst |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000034252A (en) | 1998-07-17 | 2000-02-02 | Mitsubishi Chemicals Corp | Production of aldehyde |
| JP2008137996A (en) * | 2006-11-09 | 2008-06-19 | Mitsubishi Chemicals Corp | Simultaneous production method of normal butanol and isobutyl aldehyde |
| KR100874608B1 (en) | 2002-05-10 | 2008-12-17 | 에보니크 옥세노 게엠베하 | A process for preparing aldehydes and alchols by hydroformylation of olefins with reduction of rhodium catalyst losses |
| KR20090028251A (en) * | 2007-09-14 | 2009-03-18 | 주식회사 엘지화학 | Phosphorus-containing catalyst composition and hydroformylation process using the same |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000034252A (en) | 1998-07-17 | 2000-02-02 | Mitsubishi Chemicals Corp | Production of aldehyde |
| KR100874608B1 (en) | 2002-05-10 | 2008-12-17 | 에보니크 옥세노 게엠베하 | A process for preparing aldehydes and alchols by hydroformylation of olefins with reduction of rhodium catalyst losses |
| JP2008137996A (en) * | 2006-11-09 | 2008-06-19 | Mitsubishi Chemicals Corp | Simultaneous production method of normal butanol and isobutyl aldehyde |
| KR20090028251A (en) * | 2007-09-14 | 2009-03-18 | 주식회사 엘지화학 | Phosphorus-containing catalyst composition and hydroformylation process using the same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11534744B2 (en) | 2016-07-08 | 2022-12-27 | Lg Chem, Ltd. | Composition including hydroformylation catalyst |
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