KR20230115501A - Method for producing alcohol - Google Patents

Abstract

This application relates to a method for producing alcohol.

Description

Method for producing alcohol {METHOD FOR PRODUCING ALCOHOL}

The present invention relates to a method for producing alcohol.

A hydroformylation reaction, generally known as an OXO reaction, is an industrially very important reaction in a homogeneous catalytic reaction, and various aldehydes including alcohol derivatives are produced and consumed worldwide through the OXO process.

Various aldehydes synthesized by the oxo reaction are sometimes transformed into various acids and alcohols containing long alkyl groups by oxidation or hydrogenation after a condensation reaction such as aldol. In particular, hydrogenated alcohol of aldehyde by the oxo reaction is called oxoalcohol, and oxoalcohol is widely used industrially for solvents, additives, raw materials for various plasticizers, and synthetic lubricants.

Octanol, a representative example of the oxoalcohol, is mainly used as a raw material for PVC plasticizers such as DOP (dioctyl phathalate), and is also used as an intermediate raw material for synthetic lubricants and surfactants.

The octanol occupies a large proportion of the production of alcohol for plasticizer, but has the following two limitations in the manufacturing process.

The first drawback of the octanol process is the continued rise in raw material costs. Propylene, a raw material of the octanol process, is also in high demand as a raw material for other polymers such as polypropylene, and its price continues to rise. The second disadvantage of the octanol process is that the process is complex and the investment cost is high. The octanol process consists of three steps: hydroformylation, dimer formation, and hydrogenation, and the hydroformylation is carried out in a continuous manner requiring two or more pressure reactors rather than a simple batch process. Since the existing octanol process cannot exclude these factors, it is necessary to develop a process for producing a new high-performance alcohol other than octanol at low cost.

Republic of Korea Patent Registration No. 10-1150557

The present invention is to provide a method for producing alcohol.

An exemplary embodiment of the present application includes preparing a raw-C5 feed, which is a product of a Naphtha Cracking Center (NCC) process; preparing C6-aldehyde by reacting the raw-C5 feed with synthesis gas in the presence of a catalyst composition for hydroformylation reaction; Pre-treating the hydrogenation catalyst under reducing conditions; and producing C6-alcohol by hydrogenating the C6-aldehyde under a pressure condition of 3 bar to 5 bar and a temperature condition of 160° C. to 175° C. in the presence of the pretreated hydrogenation catalyst. do.

According to an exemplary embodiment of the present application, the formation of by-products generated in the process of producing alcohol by hydrogenating aldehyde can be suppressed, and the selectivity of alcohol can be increased.

According to an exemplary embodiment of the present application, it is possible to increase the yield of alcohol, which is a product of the process of producing alcohol by hydrogenating aldehyde.

1 is a diagram schematically illustrating a process diagram of a method for producing alcohol according to an exemplary embodiment of the present application.

Hereinafter, the present invention will be described in detail so that those skilled in the art can easily practice it. However, the present invention may be embodied in many different forms and is not limited to the configurations described herein.

In this specification, when a certain part 'includes' a certain component, this means that it may further include other components, not excluding other components unless otherwise stated.

In this specification, 'p to q' means 'p or more and less than q'.

In addition, in describing the present invention, detailed descriptions of related known technologies that may unnecessarily obscure the subject matter of the present invention will be omitted.

An exemplary embodiment of the present invention includes preparing a raw-C5 feed, which is a product of a Naphtha Cracking Center (NCC) process; preparing C6-aldehyde by reacting the raw-C5 feed with synthesis gas in the presence of a catalyst composition for hydroformylation reaction; Pre-treating the hydrogenation catalyst under reducing conditions; and producing C6-alcohol by hydrogenating the C6-aldehyde under a pressure condition of 3 bar to 5 bar and a temperature condition of 160° C. to 175° C. in the presence of the pretreated hydrogenation catalyst. do.

In one embodiment of the present invention, a pressure condition of 3 bar to 5 bar, preferably 3.5 bar to 4.5 bar, and a temperature of 160 ° C to 175 ° C, preferably 165 ° C to 175 ° C, in the presence of the pretreated catalyst for hydrogenation reaction Provided is a method for producing alcohol comprising the step of hydrogenating the C6-aldehyde under conditions to produce C6-alcohol.

In general, the reaction of reducing C6-aldehyde component to C6-alcohol proceeds at a temperature of 160° C. or more and 3 bar or more, considering the boiling point of C6-aldehyde and the pressure at which the hydrogenation reaction easily occurs. Therefore, the present invention for preparing an alcohol comprising the step of preparing a C6-alcohol must proceed at a temperature of 160° C. or higher and a pressure of 3 bar or higher. In addition, if the process is carried out at too high a temperature or pressure, a condition in which aldehyde polymerization may occur or the catalyst may be out of activation condition. Accordingly, by hydrogenating an aldehyde while satisfying the pressure and temperature conditions, the formation of by-products generated in the process of preparing alcohol can be suppressed, and the selectivity and yield of alcohol can be increased.

Raw-C5, one of the products of the Naphtha Cracking Center (NCC) process, is traded cheaply at the price of naphtha and has a high olefin content of 40% to 50% by weight, so it is converted to aldehyde through the hydroformylation process. It is a raw material with high economic efficiency.

Currently, after separating specific C5 olefins such as isoprene from raw-C5 feed in advance, C6-aldehyde is produced using the separated specific C5 olefin, and then C6-alcohol is produced. For reference, in order to selectively use a specific C5 olefin such as isoprene in the raw-C5 feed, a separation process and a purification process using the raw-C5 feed must necessarily precede.

In the present specification, the separation process and purification process using the raw-C5 feed may use methods known in the art.

In an exemplary embodiment of the present application, the hydrogenation catalyst may include one or more of copper, nickel, copper-zinc, and platinum.

More specifically, in an exemplary embodiment of the present application, the catalyst for the hydrogenation reaction may be represented by Formula 1 below.

[Formula 1]

CuO—ZnO—Al ₂ O ₃

In an exemplary embodiment of the present application, the hydrogenation catalyst represented by Chemical Formula 1 includes 30 parts by weight to 35 parts by weight of CuO, 60 parts by weight to 70 parts by weight of ZnO, and Al ₂ O ₃ based on 100 parts by weight of the hydrogenation catalyst. It may include 1 part by weight to 3 parts by weight.

In an exemplary embodiment of the present application, the step of pre-treating the hydrogenation catalyst under reducing conditions may be performed while supplying N ₂ and H ₂ under a temperature condition of 200° C. to 400° C.

More specifically, the step of pretreating the hydrogenation catalyst under reducing conditions is carried out while supplying N ₂ and H ₂ under a temperature condition of 200 ° C to 400 ° C, preferably 200 ° C to 300 ° C, and the N ₂ is supplied at a flow rate of 60 cc/min to 150 cc/min, preferably 80 cc/min to 120 cc/min, and H ₂ is supplied at a flow rate of 3 cc/min to 20 cc/min, preferably 6 cc/min to 15 cc/min. may be supplied.

In one embodiment of the present application, the hydrogenation reaction of the C6-aldehyde may proceed while supplying N ₂ and H ₂ .

More specifically, the hydrogenation reaction of the C6-aldehyde proceeds while supplying N ₂ and H ₂ , and the N ₂ is 40 cc/min to 220 cc/min, preferably 50 cc/min to 220 cc/min, more preferably is supplied at a flow rate of 100 cc/min to 210 cc/min, and the H ₂ is 60 cc/min to 220 cc/min, preferably 65 cc/min to 150 cc/min, more preferably 65 cc/min to 90 cc/min. may be supplied by

Most preferably, the hydrogenation reaction of the C6-aldehyde proceeds while supplying N ₂ and H ₂ , the N ₂ is supplied at a flow rate of 190 cc/min to 210 cc/min, and the H ₂ is supplied at a flow rate of 65 cc/min to 210 cc/min. It may be supplied at a flow rate of 75 cc/min. If this is satisfied, the yield of C6-alcohol prepared from the raw-C5 feed is very high, similar to the yield of C6-alcohol prepared using a single aldehyde.

In an exemplary embodiment of the present application, the hydrogenation reaction of the C6-aldehyde may be performed in a hydrogenation reactor. The hydrogenation reactor is not particularly limited as long as it can fix the above-mentioned hydrogenation catalyst. For example, a continuous stirred reactor (CSTR), a venturi-loop reactor, a trickle-bed reactor, etc. can be used. can

A process diagram of a method for producing alcohol according to an exemplary embodiment of the present application is schematically shown in FIG. 1 below. As shown in FIG. 1 below, in an exemplary embodiment of the present application, C6-aldehyde is prepared by performing a hydroformylation process (HF reaction) on raw-C5 feed. A hydrogenation reaction may be performed on the C6-aldehyde to produce C6-alcohol.

In this process, after separating specific C5 olefins such as isoprene from the raw-C5 feed in advance, C6-aldehyde is produced using the separated specific C5 olefin, and then C6-alcohol can be produced using it. there is.

In addition, unlike the above-described method, in the product of C6-aldehyde and unreacted raw-C5 feed generated after the step of reacting the raw-C5 feed with synthesis gas without separating a specific C5 olefin in advance, the unreacted raw -C5 feed can be separated and recovered, and C6-alcohol can be produced using the C6-aldehyde.

That is, a product generated after the step of reacting raw-C5 feed with synthesis gas may be a C6-aldehyde mixture.

In this way, the unreacted raw-C5 feed is separated and recovered from the product of C6-aldehyde and unreacted raw-C5 feed generated after the step of reacting the raw-C5 feed with synthesis gas without separating the C5 olefin. , There is an effect of reducing operating cost and investment cost during the manufacturing process of aldehyde and / or alcohol.

At this time, the separation of the unreacted raw-C5 feed may use the difference in boiling point.

Specifically, the separation of the C6-aldehyde and unreacted raw-C5 feed may be performed using a distillation process. The boiling point of the substances included in the unreacted raw-C5 feed is less than 100 ° C, and the boiling point of C6-aldehyde is 120 ° C to 140 ° C, and the boiling point difference is very large, so it can be easily separated using little energy.

In the distillation process for separating the C6-aldehyde and the unreacted raw-C5 feed, C6-aldehyde having a relatively high boiling point can be separated from the bottom of the distillation column, and all materials other than C6-aldehyde are removed from the top of the distillation column. It can be separated and discharged. At this time, the material separated at the top of the distillation column may be recovered as raw-C5 feed.

In one embodiment of the present application, specific components of the raw-C5 feed are shown in Table 1 below.

In an exemplary embodiment of the present application, the C5 terminal monoene is 1-pentene, 2-methyl-1-butene, 3-methyl-1-butene (3 -methyl-1-butene), cyclopentene, and the like. In addition, the C5 internal monoene may include 2-pentene, 2-methyl-2-butene, and the like. In addition, the C5 diene is isoprene, 1,3-pentadiene (1,3-pentadiene), 1,4-pentadiene (1,4-pentadiene), 2-methyl-1-butene-3-in (2-methyl-1-buten-3-yne) and the like.

In one embodiment of the present application, based on the total weight of the mixture of the terminal monoene, internal monoene, and diene, the content of the diene may be 30% by weight or more, , 40% to 80% by weight.

In one embodiment of the present application, the catalyst composition for the hydroformylation reaction includes a phosphine-based ligand; A transition metal compound represented by Formula 2 below; and a solvent.

[Formula 2]

M(L1)x(L2)y(L3)z

In Formula 2,

M is rhodium (Rh), cobalt (Co), iridium (Ir), ruthenium (Ru), iron (Fe), nickel (Ni), palladium (Pd), platinum (Pt) or osmium (Os),

L1, L2 and L3 are the same as or different from each other, and each independently hydrogen, carbonyl (CO), cyclooctadiene, norbornene, chlorine, triphenylphosphine (TPP) Or acetylacetonato (acetylacetonato, AcAc),

The x, y, and z are each independently an integer of 0 to 5, and x, y, and z are not 0 at the same time.

In one embodiment of the present application, the phosphine-based ligand may use a diphosphine-based ligand such as 1,2-bis (diphenylphosphino) ethane (DPPE), It is not limited to this.

In an exemplary embodiment of the present application, the transition metal compound is cobaltcarbonyl [Co ₂ (CO) ₈ ], acetylacetonatodicarbonylodium [Rh(AcAc)(CO) ₂ ], acetylacetonatocarbonyl Triphenylphosphine rhodium [Rh(AcAc)(CO)(TPP)], hydridocarbonyltri(triphenylphosphine)rhodium [HRh(CO)(TPP) ₃ ], acetylacetonatodicarbonyliridium [Ir (AcAc)(CO) ₂ ], hydridocarbonyltri(triphenylphosphine)iridium [HIr(CO)(TPP) ₃ ] and chloro(1,5-cyclooctadiene)rhodium [Rh(COD)Cl ₂ ] may include one or more of them.

In one embodiment of the present application, the solvent is propane aldehyde, butyl aldehyde, pentyl aldehyde, valeraldehyde, acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, cyclohexanone, ethanol, pentanol, octanol, at least one of tensanol, benzene, toluene, xylene, orthodichlorobenzene, tetrahydrofuran, dimethoxyethane, dioxane, methylene chloride and heptane.

In an exemplary embodiment of the present application, the step of reacting the raw-C5 feed with synthesis gas to produce C6-aldehyde may be performed at a reaction temperature of 50 °C to 130 °C and a pressure of 5 bar to 75 bar.

In an exemplary embodiment of the present application, the step of preparing C6-aldehyde by reacting the raw-C5 feed with synthesis gas may be performed at a reaction temperature of 50 ° C to 130 ° C and a pressure of 5 bar to 75 bar, It may be carried out at a reaction temperature of 70 °C to 110 °C and a pressure of 5 bar to 50 bar. When the reaction temperature in the step of reacting the raw-C5 feed with synthesis gas to produce C6-aldehyde is less than 50 ° C, the activity of the reaction may decrease or the reaction may not occur, and when it exceeds 130 ° C, the catalyst and The ligand may be decomposed, and the reactivity may be lowered.

In an exemplary embodiment of the present application, in the step of preparing C6-aldehyde by reacting the raw-C5 feed with synthesis gas, the molar ratio of the raw-C5 feed: synthesis gas may be 95: 5 to 5: 95. .

In an exemplary embodiment of the present application, the synthesis gas includes carbon monoxide and hydrogen, and the molar ratio of carbon monoxide to hydrogen may be 20:80 to 80:20 or 30:70 to 70:30.

In one embodiment of the present application, the hydroformylation reaction may use a method known in the art.

Hereinafter, examples will be described in detail in order to specifically describe the present application. However, embodiments according to the present application may be modified in many different forms, and the scope of rights of the present application is not construed as being limited to the embodiments detailed below. The embodiments of the present application are provided to more completely explain the present application to those skilled in the art.

<Example>

<Preparation of aldehyde>

<Production Example 1>

The C5 stream solution (raw-C5) collected from LG Chem's Daesan NCC plant, catalyst precursor, ligand, and solvent were mixed at a predetermined ratio and put into a pressure reactor (capacity: 500 mL). Rhacac(CO) ₂ was used as a catalyst precursor, 1,2-bis(diphenylphosphino)ethane (DPPE) as a ligand, and tetraethylene glycol dimethyl ether (DPPE) as a solvent. Tetraethylene glycol dimethyl ether, TEGDME) were used, respectively. The C5 stream solution: catalyst precursor: ligand: solvent = 10 g: 0.1 g: 2 g: 100 g was introduced. Components of the C5 stream solution are the same as those in Table 1 above.

While stirring the reaction solution at 1,000 rpm, the inside of the reactor was purged with a nitrogen atmosphere. When purging was completed, the temperature inside the reactor was heated to 100°C. After reaching the reaction temperature, synthesis gas (CO/H ₂ = 1/1) was injected into the reactor at 40 bar to initiate the hydroformylation reaction. After maintaining the hydroformylation reaction condition for 12 hours, the reactor was cooled to room temperature and the reaction was terminated by removing gas inside the reactor to obtain a 6-aldehyde mixture.

<Example 1>

3g of CuO-ZnO-Al ₂ O ₃ (CuO: 33%, ZnO: 65%-Al ₂ O ₃ : 2%, hereinafter referred to as OXO-1), which is a hydrogenation catalyst shown in Table 2 below, was charged into the reactor, A pretreatment for reducing the catalyst was performed under the reducing conditions shown in Table 2 below. Specifically, after raising the temperature from room temperature to the reduction temperature condition shown in Table 2 for 4 hours, the pretreatment was performed while maintaining the temperature for 2 hours.

Thereafter, the temperature of the reactor was cooled to the reaction temperature conditions described in Table 3 below, and then maintained.

Thereafter, the 6-aldehyde mixture prepared in Preparation Example 1 was introduced into the reactor at a flow rate of 0.275 cc/min, and alcohol was prepared by hydrogenating the 6-aldehyde under the reaction conditions shown in Table 3 below.

The prepared alcohol was analyzed by GC equipped with an HP-1 column to analyze 6-aldehyde conversion rate, 6-alcohol selectivity, and 6-alcohol yield.

The results are shown in Table 3 below.

<Example 2, Comparative Examples 1 to 7, Reference Examples 1 and 2>

As shown in Table 2 below, the aldehyde mixture or 2-ethylhexanl of Preparation Example 1 was used as a reactant, except that the type of catalyst, pretreatment conditions, and reaction conditions were set as shown in Tables 2 and 3 below. Alcohols of Example 2, Comparative Examples 1 to 7, and Reference Examples 1 and 2 were prepared by hydrogenating 6 aldehydes in the same manner as in Example 1.

In Table 2 below, PRICAT is NiO/SiO ₂ /promoter (NiO: 50%), PdO/C is PdO/C (PdO: 5%), and the C6-aldehyde mixture is prepared from raw-C5 by the method of Preparation Example 1 above. means the obtained material.

reactant catalyst (pretreatment condition)
reduction condition Temperature (℃) N ₂ (cc/min) H ₂ (cc/min) Example 1 C6-aldehyde mixture OXO-1 250 100 10 Example 2 C6-aldehyde mixture OXO-1 250 100 10 Comparative Example 1 C6-aldehyde mixture OXO-1 250 100 10 Comparative Example 2 C6-aldehyde mixture PRICAT 450 100 10 Comparative Example 3 C6-aldehyde mixture PdO/C 250 100 10 Comparative Example 4 C6-aldehyde mixture OXO-1 250 100 10 Comparative Example 5 C6-aldehyde mixture OXO-1 250 100 10 Comparative Example 6 C6-aldehyde mixture OXO-1 250 100 10 Comparative Example 7 C6-aldehyde mixture OXO-1 250 100 10 Reference example 1 2-ethlyhexanal OXO-1 250 100 10 Reference example 2 2-ethlyhexanal OXO-1 250 100 10

reaction conditions Temperature (℃) pressure (bar) N ₂ (cc/min) H ₂ (cc/min) Example 1 170 4 200 70 Example 2 170 4 53 211.5 Comparative Example 1 170 One 0 70 Comparative Example 2 170 One 0 70 Comparative Example 3 170 One 0 70 Comparative Example 4 180 One 0 70 Comparative Example 5 170 One 200 70 Comparative Example 6 170 One 53 211.5 Comparative Example 7 170 6 200 70 Reference example 1 170 4 200 70 Reference example 2 170 6 200 70

Alcohols of Examples 1 and 2, Comparative Examples 1 to 7, and Reference Examples 1 and 2 prepared by the above method were analyzed by GC equipped with an HP-1 column to obtain C6-aldehyde conversion, C6-alcohol selectivity and C6-alcohol Yield was analyzed.

The results are shown in Table 4 below.

C6-aldehyde conversion (%) C6-alcohol selectivity (%) C6-alcohol yield (%) Example 1 99.5 99.2 98.7 Example 2 99.2 98.5 97.7 Comparative Example 1 94.7 98.5 93.2 Comparative Example 2 96.1 55.0 52.8 Comparative Example 3 91.5 35.5 7.6 Comparative Example 4 94.3 91.3 86.1 Comparative Example 5 78.1 99.5 77.7 Comparative Example 6 90.3 99.0 89.4 Comparative Example 7 99.8 96.1 95.9 Reference example 1 99.5 99.3 98.8 Reference example 2 99.8 99.1 98.9

In Table 4, C6-aldehyde conversion rate, C6-alcohol selectivity and C6-alcohol yield were calculated as follows.

C6-aldehyde conversion rate (%) = [Number of moles of C6-aldehyde reacted/Number of moles of C6-aldehyde supplied] Х 100 (%)

C6-alcohol selectivity (%) = [number of moles of C6-alcohol produced/number of moles of C6-aldehyde reacted] Х 100 (%)

C6-alcohol yield (%) = [number of moles of C6-alcohol produced / number of moles of C6-aldehyde supplied] Х 100 (%)

In addition, the GC analysis conditions were as follows.

<GC analysis conditions>

① Column: HP-1 (L:100m, ID:0.25mm, film:0.5㎛)

② Injection volume: 1 μl

③ Inlet Temp.: 250℃, Pressure: 34.46psi, Total flow: 32.8ml/min, Split flow: 28.4ml/min, spill ratio: 20:1

④ Column flow: 1.4ml/min

⑤ Oven temp.: 35℃, 3min (hold) / 170℃, 2℃/min / 300℃, 10℃/min 20min (hold) (Total 120min)

⑥ Detector temp.: 250℃ H2: 30ml/min, Air: 300ml/min, He: 25ml/min

⑦ GC Model: Agilent 7890B

As shown in Table 4 above, unlike the case of Reference Examples 1 and 2 using 2-ethlyhexanal as a single component as a reactant used to prepare aldehyde, the selectivity and yield of alcohol decrease depending on the type of catalyst and reaction conditions. was able to confirm

That is, it was confirmed that the reaction conditions according to the present application should be satisfied in order to secure high alcohol selectivity and yield from the C6-aldehyde mixture produced as a C5 stream solution (raw-C5).

Specifically, when a catalyst having too strong hydrogenation ability was used as in Comparative Examples 2 and 3, it was confirmed that the selectivity and yield of alcohol decreased.

In addition, it was confirmed from Comparative Example 4 that the selectivity and yield of alcohol decreased even when the reaction temperature was out of the conditions of the present application. This is judged to be the result of creating conditions in which polymerization of aldehyde can occur.

In addition, from the results of Comparative Examples 1 to 4 and Comparative Example 7, it was confirmed that the selectivity and yield of alcohol decreased even when the reaction pressure was out of the pressure condition of the present application. It is believed that this is because the reaction can be performed well when the pressure is increased, but when too high a pressure is applied, a lot of polymerization products are formed due to the generation of heat of hydrogenation reaction.

In addition, it was found that the conditions of N ₂ and H ₂ also affect the selectivity and yield of alcohol during buto reaction in Comparative Examples 1, 5 and 6.

In summary, from Table 4, it was confirmed that the alcohol selectivity and yield of Examples 1 and 2 satisfying the reaction conditions of the present application were excellent, and in particular, it was confirmed that Example 1 was the optimized reaction condition.

Claims (10)

Preparing raw-C5 feed, which is a product of the Naphtha Cracking Center (NCC) process;
preparing C6-aldehyde by reacting the raw-C5 feed with synthesis gas in the presence of a catalyst composition for hydroformylation reaction;
Pre-treating the hydrogenation catalyst under reducing conditions; and
Hydrogenating the C6-aldehyde in the presence of the pretreated hydrogenation catalyst under a pressure condition of 3 bar to 5 bar and a temperature condition of 160 ° C to 175 ° C to produce C6-alcohol. According to claim 1,
The catalyst for the hydrogenation reaction is a method for producing an alcohol comprising at least one of copper, nickel, copper-zinc and platinum. According to claim 1,
The catalyst for the hydrogenation reaction is a method for producing an alcohol represented by the following formula (1):
[Formula 1]
CuO—ZnO—Al ₂ O ₃ According to claim 1,
The step of pre-treating the hydrogenation catalyst under reducing conditions is a method for producing alcohol that proceeds while supplying N ₂ and H ₂ under a temperature condition of 200 ° C to 400 ° C. According to claim 1,
The hydrogenation reaction of the C6-aldehyde proceeds while supplying N ₂ and H ₂
The N ₂ is supplied at a flow rate of 50 cc/min to 220 cc/min,
The H ₂ is a method for producing alcohol that is supplied at a flow rate of 60 cc / min to 220 cc / min. According to claim 1,
The step of producing C6-aldehyde by reacting the raw-C5 feed with synthesis gas is carried out at a reaction temperature of 50 ° C to 130 ° C and a pressure of 5 bar to 75 bar. According to claim 1,
The raw-C5 feed is a method for producing alcohol comprising a mixture of terminal monoene, internal monoene and diene. According to claim 1,
The catalyst composition for the hydroformylation reaction includes a phosphine-based ligand; A transition metal compound represented by Formula 2 below; And a method for producing an alcohol comprising a solvent:
[Formula 2]
M(L1)x(L2)y(L3)z
In Formula 2,
M is rhodium (Rh), cobalt (Co), iridium (Ir), ruthenium (Ru), iron (Fe), nickel (Ni), palladium (Pd), platinum (Pt) or osmium (Os),
L1, L2 and L3 are the same as or different from each other, and each independently hydrogen, carbonyl (CO), cyclooctadiene, norbornene, chlorine, triphenylphosphine (TPP) Or acetylacetonato (acetylacetonato, AcAc),
The x, y, and z are each independently an integer of 0 to 5, and x, y, and z are not 0 at the same time. According to claim 1,
In the step of reacting the raw-C5 feed with synthesis gas to produce C6-aldehyde,
Wherein the raw-C5 feed: the molar ratio of synthesis gas is 95: 5 to 5: 95. According to claim 1,
The synthesis gas includes carbon monoxide and hydrogen,
Wherein the carbon monoxide: hydrogen molar ratio is 30: 70 to 70: 30.