JPH11189563A - Preservation of hydroformylated product - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for stably preserving the subject product without purifying operation by obtaining a specific hydroformylation product in a shape to be included in an organic layer, and preserving the obtained organic layer in the presence of a specified compound. SOLUTION: A hydroformylation product obtained by reacting (A) an olefinic compound (e.g. 7-octen-1-al) with (B) hydrogen and (C) carbon monoxide in the presence of (D) a rhodium compound (e.g. rhodium acetylacetonate), (E) an alkali(ne earth) metal salt of tertiary-organic phosphorus compound having sulfonic acid group (SO3 H) (e.g. lithium 3-diphenylphosphino-1-benzenesulfonate) and (F) a polar organic compound is obtained in a state included in an organic layer preferably obtained by the method for carrying out an extraction operation of the hydroformylation reaction mixture with water, and the obtained organic layer is preserved in the presence of (G) an basic compound and/or an epoxy compound in the method for preserving the objective compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for preserving a hydroformylation product of an olefinic compound, which is useful as an intermediate for pharmaceuticals, agricultural chemicals, fragrances and the like.

[0002]

2. Description of the Related Art A method of producing an aldehyde by reacting an olefinic compound with hydrogen and carbon monoxide using a rhodium compound as a catalyst is called a hydroformylation reaction or an oxo reaction, and is an industrially useful synthesis method. Is the law. However, since the rhodium compound is expensive, a technique for recycling the rhodium compound is required to carry out the above-mentioned hydroformylation reaction industrially and advantageously. As a method of separating a rhodium compound and a hydroformylation product from a reaction mixture in a hydroformylation reaction, a rhodium catalyst is made water-soluble, a hydroformylation reaction is carried out in an aqueous solvent, and then an extraction solvent such as a hydrocarbon solvent is used. A method in which a hydroformylation product is extracted and separated into an organic layer, and a rhodium catalyst is left in an aqueous layer (Japanese Patent Publication No. 6-62479, JP-A-58-201).
743) or a water-soluble rhodium catalyst dissolved in a reaction solution using a solubilizing agent such as N-methylpyrrolidone to carry out a hydroformylation reaction, and then using water as an extraction solvent. A method in which a rhodium catalyst is extracted and separated into an aqueous layer and a hydroformylation product is left in an organic layer (US Pat. No. 5,180,854;
A method using extraction separation is known.

[0003]

In the method for separating a rhodium compound and a hydroformylation product from a hydroformylation reaction mixture by using the above-mentioned extraction separation, the method comprises the steps of: Monodentate tertiary organic phosphorus compounds having a substituent represented by SO ₃ M (M represents an alkali metal) are suitably used as a cocatalyst. And the hydroformylation product taken out in the form contained in the organic layer by these methods is:
If necessary, the compound is further converted to another compound by a reduction reaction, an oxidation reaction, or the like. However, according to the findings of the present inventors, the hydroformylation product obtained in the form contained in the organic layer by the above method has low storage stability as it is, and has a high boiling point within a relatively short period of time. May produce large amounts of compound. For this reason, when the hydroformylation product in the form contained in the organic layer is directly used for a subsequent reaction such as a reduction reaction, the next reaction may be carried out within a short time after the completion of the hydroformylation reaction. This is a restriction in establishing an industrial process for producing various useful substances using the obtained hydroformylation product as an intermediate. In order to solve this problem, the hydroformylation product taken out in the form contained in the organic layer may be subjected to a purification operation such as distillation, but the production cost is increased due to the additional purification step. And the loss of hydroformylation products. Thus, the present invention provides a hydroformylation product extracted from a hydroformylation reaction mixture of an olefinic compound catalyzed by a water-soluble rhodium compound in a form contained in an organic layer, stably without performing a purification operation. It is an object to provide a method that can be stored.

[0004]

Means for Solving the Problems As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that an organic layer containing a hydroformylation product obtained from a hydroformylation reaction mixture of an olefinic compound has a trace amount. It has been found that the acid substance is one of the causes of greatly impairing the stability of the hydroformylation product, and as a result of further investigation, the present invention has been completed. That is, the present invention provides an olefinic compound as (a) a rhodium compound, (b) a sulfonic acid group (-S
An alkali metal salt or an alkaline earth metal salt of a tertiary organic phosphorus compound having O ₃ H) (hereinafter sometimes abbreviated as a salt of a tertiary organic phosphorus compound), and (c)
A method for storing a hydroformylation product obtained by reacting hydrogen and carbon monoxide in the presence of a polar organic compound, wherein the hydroformylation product is contained in an organic layer from a hydroformylation reaction mixture of the olefinic compound. And storing the organic layer in the presence of a basic compound and / or an epoxy compound in the form of a hydroformylation product of an olefinic compound.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, the olefinic compound as a raw material for the hydroformylation reaction is a compound having an ethylenic carbon-carbon double bond,
Any material that reacts with hydrogen and carbon monoxide to give the corresponding aldehydes can be used. Such an olefinic compound may have a substituent that does not inhibit the hydroformylation reaction. Examples of such a substituent include a formyl group; a hydroxyl group; an alkoxy group such as a methoxy group and an ethoxy group; an alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group and a t-butoxycarbonyl group; a cyano group; Examples include a halogen atom such as a bromine atom.

Here, specific examples of the olefinic compound include 1-butene, 2-butene, isobutene, 1-hexene, 1-octene, cyclohexene, styrene,
Unsaturated hydrocarbons such as 5-hexadiene, 1,7-octadiene, vinylcyclohexene, dicyclopentadiene and cyclooctadiene; unsaturated aldehydes such as 7-octen-1-al; 7-octen-1-ol;
Unsaturated alcohols such as 2,7-octadien-1-ol; acrylonitrile; vinyl acetate; vinyl chloride; methyl methacrylate and the like.

The rhodium compound used in the present invention includes:
Any rhodium compound that has hydroformylation catalysis or changes to have hydroformylation catalysis under the conditions of the hydroformylation reaction can be used, for example, HRh (CO) (PPh ₃ ), Rh ₄ (C
_{O) 12, Rh 6 (CO} ) 16, Rh (acac) (C
O) ₂ , rhodium oxide, rhodium chloride, rhodium acetylacetonate, rhodium acetate, RhCl (PPh ₃ ) ₃
And the like.

The amount of the rhodium compound to be used is usually such that the concentration is in the range of 0.005 to 10 milligram atoms in terms of rhodium atom per liter of the hydroformylation reaction solution.

The salt of the tertiary organic phosphorus compound used in the present invention is a tertiary organic phosphorus compound having a sulfonic acid group (—SO ₃ H).
Alkali metal salts or alkaline earth metal salts of organic phosphorus compounds of lower grades. Here, the alkali metal is lithium, sodium or potassium, and the alkaline earth metal is
Magnesium and calcium. Such a salt of the tertiary organic phosphorus compound may be a salt of a compound having two or more sulfonic acid groups, and in that case, it is preferable that all of the sulfonic acid groups form a salt.

Specific examples of the salt of the tertiary organic phosphorus compound include sodium 3-diphenylphosphino-1-benzenesulfonate, lithium 3-diphenylphosphino-1-benzenesulfonate, and 3-diphenylphosphino- 1
-Potassium benzenesulfonate, calcium 3-diphenylphosphino-1-benzenesulfonate, magnesium 3-diphenylphosphino-1-benzenesulfonate, sodium 3-butylphenylphosphino-1-benzenesulfonate, 3-butylcyclohexyl Sodium phosphino-1-benzenesulfonate, 3-bis (1
-Methylethyl) sodium phosphino-1-benzenesulfonate, lithium 3-dicyclohexylphosphino-1-benzenesulfonate, sodium 3-dicyclohexylphosphino-1-benzenesulfonate, 3-dicyclohexylphosphino-1-benzenesulfonate Potassium, sodium 3-hexadecylphenylphosphino-1-benzenesulfonate, sodium 3-dicyclohexylphosphino-1-propanesulfonate, sodium 3-diphenylphosphino-1-propanesulfonate, 4-diphenylphosphino-1 Sodium butanesulfonate, sodium 4- (1,1-dimethylethyl) (phenyl) phosphino-1-butanesulfonate, 3
Salts of tertiary organic phosphorus compounds having one sulfonic acid group, such as sodium diethylphosphino-1-propanesulfonate and sodium 3-dihexylphosphino-1-propanesulfonate; 3- [phenyl (3-sulfosulfonic acid); Phenyl) phosphino] -1-benzenesulfonic acid disodium salt, 3- [phenyl (3-sulfophenyl) phosphino] -1-benzenesulfonic acid dilithium salt, 3- [phenyl (3-sulfophenyl) phosphino] -1 -Dipotassium benzenesulfonate, 3- [phenyl (3-sulfophenyl) phosphino] -1-calcium salt of 1-benzenesulfonate, 3- [phenyl (3-sulfophenyl)
Phosphino] -1-A salt of a tertiary organic phosphorus compound having two sulfonic acid groups such as magnesium benzenesulfonate; 3-bis (3-sulfophenyl) phosphino-1-
Benzenesulfonic acid trisodium salt, 3-bis (3-sulfophenyl) phosphino-1-benzenesulfonic acid trilithium salt, 3-bis (3-sulfophenyl) phosphino-1-benzenesulfonic acid tripotassium salt, 3-bis (3-Sulfophenyl) phosphino-1-benzenesulfonic acid calcium salt, 3-bis (3-sulfophenyl)
Salts of a tertiary organic phosphorus compound having three sulfonic acid groups, such as magnesium phosphino-1-benzenesulfonate, are exemplified.

As the salt of the tertiary organic phosphorus compound, one kind may be used, or two or more kinds may be used in combination.

The amount of the salt of the tertiary organic phosphorus compound to be used is usually an amount that gives a concentration in the range of 1 mmol or more, preferably 2 mmol or more per liter of the hydroformylation reaction solution. The amount of the salt of the tertiary organophosphorus compound used is preferably such that the concentration falls within the above range and at the same time, the amount becomes 2 mol or more per gram atom of rhodium. More preferably, the amount is 20 mol or more per unit. The upper limit of the amount of the salt of the tertiary organic phosphorus compound is not particularly limited. However, in consideration of the production cost and the like, the concentration is in the range of 200 mmol or less per liter of the hydroformylation reaction solution. Is good.

The polar organic compound used in the present invention means an olefinic compound which is inert to the hydroformylation reaction of the olefinic compound and also inert to the olefinic compound and its hydroformylation product. When the reaction mixture containing the polar organic compound is mixed with the compound and the reaction product uniformly and water, the mixture is separated into two layers, an aqueous layer and an organic layer, and the polar organic compound in the reaction mixture is separated. It refers to a compound that has the property of being at least partially extracted into the aqueous layer. It is preferable that the polar organic compound has a property of being uniformly mixed with the salt of the tertiary organic phosphorus compound.

As such a polar organic compound, for example,
Sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; carbonates such as ethylene carbonate; amides such as N-methylpyrrolidone and N, N-dimethylformamide; nitriles such as acetonitrile; diols such as ethylene glycol and butanediol. Polyalkylene glycols such as diethylene glycol and polyethylene glycol (number average molecular weight 400); polyalkylene glycol monomethyl ethers such as polyethylene glycol monomethyl ether (number average molecular weight 400); triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, polyethylene glycol Polyalkylene glycol dimethyl ethers such as dimethyl ether (number average molecular weight 400) Etc., and the like. Among these,
Dimethyl sulfoxide, N-methylpyrrolidone, N, N
-Dimethylformamide, number average molecular weight of 300 or more 6
Polyethylene glycol having a molecular weight of 00 or less and polyethylene glycol dimethyl ether having a number average molecular weight of 300 or more and 600 or less are suitable in terms of an extraction recovery rate in an aqueous layer and separability from water after extraction, and are relatively easily available. Therefore, it is a polar organic compound suitable for industrially carrying out the method of the present invention. These polar organic compounds may be used alone or as a mixture of two or more.

The amount of the polar organic compound to be used is usually an amount in the range of 2% by volume to 30% by volume in the hydroformylation reaction solution.
It is preferable that the concentration is in the range of 5% by volume or more and 20% by volume or less.

The hydroformylation reaction of the olefinic compound is usually carried out at 40 to 140 ° C., preferably at 70 to 120 ° C.
Carried out at a temperature in the range The molar ratio of hydrogen to carbon monoxide in the hydrogen / carbon monoxide mixed gas used for the reaction is usually expressed as hydrogen / carbon monoxide = 1 as the input gas composition.
/ 2 to 5/1. The reaction pressure is generally in the range of normal pressure to 300 atm, preferably 2 to 300 atm.
It is in the range of 100 atm.

The hydroformylation reaction of the olefinic compound can be carried out in a known reactor such as a stirred reactor or a bubble column reactor, in a continuous or batch system.

The olefinic compound is converted to the corresponding aldehyde by the above-mentioned hydroformylation reaction.
Specific examples of the obtained aldehydes include, for example, aliphatic aldehydes such as butanal, 2-methylpropanal and nonanal; aromatic aldehydes such as 2-phenylpropanal and 3-phenylpropanal; 3- (3- Unsaturated aldehydes such as cyclohexenyl) propanal, 2- (3-cyclohexenyl) propanal, 7-octen-1-al; 9-hydroxynonanal, 2-methyl-8-hydroxyoctanal, 9-hydroxy- 7
-Hydroxy aldehydes such as nonene-1-al;
Ester aldehydes such as methyl formyl-2-methylpropionate; 2-formyltetrahydrofuran, 3-
Ether aldehydes such as formyltetrahydrofuran; 2-hydroxy-4-methyltetrahydrofuran;
Hemiacetals such as 2-hydroxy-4-methyltetrahydropyran; 1,5-diformylcyclooctane;
Examples include polyhydric aldehydes such as 1,5,9-triformylcyclododecane, 2-methyl-1,8-octanedial, and 1,9-nonandial.

The hydroformylation product of the olefinic compound obtained by the above-mentioned hydroformylation reaction is
It is removed from the hydroformylation reaction mixture in the form contained in the organic layer. The method for removing the hydroformylation product of the olefinic compound in a form contained in the organic layer includes the following steps: i) subjecting the reaction mixture to an extraction operation with water to obtain a rhodium compound, a salt of a tertiary organophosphorus compound, and a polar organic compound. Separating the compound into an aqueous layer and leaving the hydroformylation product of the olefinic compound in the organic layer, or ii) subjecting the reaction mixture to extraction with a hydrocarbon solvent such as hexane to hydroformylate the olefinic compound. There are two methods of obtaining the product as a solution of the hydrocarbon-based solvent. Either method may be used in the present invention, but the desired hydroformylation product is produced on an industrial scale. If so, it is preferable to adopt a method of performing an extraction operation with water on the reaction mixture from the viewpoint of production cost, incidental facilities, and the like. .

When an extraction operation with water is performed on the reaction mixture, the proportion of water used is preferably in the range of 1/20 to 2/1 by volume relative to the reaction mixture, and 1/20.
More preferably, it is in the range of 20 to 1/1. The extraction temperature is usually set within the range of 10 to 90 ° C. The extraction operation is preferably performed in an atmosphere of an inert gas such as nitrogen, helium, or argon, or a mixed gas of hydrogen and carbon monoxide.

On the other hand, when the reaction mixture is subjected to an extraction operation with a hydrocarbon solvent, the proportion of the hydrocarbon solvent used is within a range of 1/20 to 2/1 by volume of the reaction mixture. It is preferably, and more preferably in the range of 1/20 to 1/1. The extraction temperature is usually 10 to 9
It is set within the range of 0 ° C. In addition, the extraction operation is performed with nitrogen,
It is preferable to perform the process under an atmosphere of an inert gas such as helium or argon or a mixed gas of hydrogen and carbon monoxide.
In the above, specific examples of the hydrocarbon-based solvent include aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane, and decalin; and aromatic hydrocarbons such as benzene, toluene, and xylene.

The organic layer thus taken out usually contains a small amount of a catalyst component (a salt of a rhodium compound and a tertiary organic phosphorus compound) and a small amount of a polar organic compound in addition to the hydroformylation product of the olefinic compound. Contains compounds.
Accordingly, it is preferable that the catalyst component and the polar organic compound are extracted and recovered in the aqueous layer by subjecting the obtained organic layer to a washing operation with water as necessary. In this case, there is no upper limit for the amount of water used, but it is usually equal to or less than the volume of the organic layer.

In the present invention, the hydroformylation product taken out of the hydroformylation reaction mixture in the form contained in the organic layer is usually stored as it is until the next reaction step such as a hydrogenation reaction or an oxidation reaction. However, if the hydroformylation product of the olefinic compound is obtained in a form contained in the organic layer by a method of performing an extraction operation with water on the reaction mixture, if necessary, hexane, cyclohexane, toluene, diethyl The organic layer may be diluted by adding an organic solvent such as ether, ethyl acetate, methylene chloride, chloroform, dimethylformamide, and acetone. When a hydroformylation product of an olefinic compound is obtained by performing an extraction operation with an organic solvent on the reaction mixture, an organic solvent such as hexane, cyclohexane, benzene, or toluene used for the extraction may be used, if necessary. Can be removed and concentrated. In the above operation, the water or hydrocarbon solvent used for extraction and various solvents used for dilution as required may be reduced in the amount of dissolved oxygen by degassing or the like. It is preferable from the viewpoint of further increasing the stability of the hydroformylation product of the acidic compound.

The organic layer containing the hydroformylation product of the olefinic compound obtained above usually contains a small amount of an acidic substance. In the present invention, in order to eliminate the influence of the acidic substance, the organic layer is stored in the presence of a basic compound and / or an epoxy compound.

The basic compound used in the present invention includes, for example, lithium carbonate, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide, sodium phosphate, disodium hydrogenphosphate, sodium hydride and the like. Sodium acetate, potassium acetate, ammonium acetate, sodium propionate, sodium stearate, sodium methoxide, sodium phenoxide, sodium t-butoxide, potassium t-butoxide, triethylamine, tributylamine, trioctylamine, triethanol Organic bases such as amines and pyridines; solid bases such as anion exchange resins; The basic compound may be supported on a carrier as necessary. One type of basic compound may be used, or two or more types may be used in combination.

Examples of the epoxy compound used in the present invention include ethylene oxide, propylene oxide, styrene oxide, cyclohexene oxide, trimethylolpropane polyglycidyl ether, neopentyl glycol diglycidyl ether, and polypropylene glycol diglycidyl ether. Can be
One kind of epoxy compound may be used,
Two or more types may be used in combination. It is also possible to use the above-mentioned basic compound and epoxy compound in combination.

The amount of the basic compound and / or the epoxy compound used is preferably 0.5 to 500 gram equivalent with respect to 1 gram equivalent of the acidic substance mixed in the organic layer. More preferably, the basic compound is in an amount of 1 to 5 gram equivalents to 1 gram equivalent of the acidic substance, while the epoxy compound is 1 to 100 gram equivalents to 1 gram equivalent of the acidic substance. It is more preferable that the amount be as follows. The amount of the acidic substance mixed in the organic layer can be measured according to a conventional method such as titration analysis using sodium hydroxide, potassium hydroxide, or the like, after concentrating the organic layer as necessary.

The basic compound and / or the epoxy compound is added to the organic layer containing the hydroformylation product of the olefinic compound. If necessary, the basic compound and / or the epoxy compound may be diluted with the above-mentioned extraction solvent or the like. It may be added to the layer. The addition of the basic compound and / or the epoxy compound is usually performed at a temperature in the range of 10 to 90C, preferably 15 to 80C.

In the present invention, the storage temperature of the organic layer containing the hydroformylation product of the olefinic compound to which the basic compound and / or the epoxy compound has been added is usually 0 to 90 ° C., preferably 5 to 60 ° C. Range. The storage of the organic layer containing the hydroformylation product of the olefinic compound is preferably performed, for example, in an atmosphere of an inert gas such as nitrogen or argon.

As described above, by adding the basic compound and / or the epoxy compound, the hydroformylation product of the olefinic compound is converted into the acidic substance mixed in the organic layer containing the hydroformylation product. It can be stored stably for a long time without being affected.

The organic layer containing a hydroformylation product of an olefinic compound to which a basic compound and / or an epoxy compound has been added is often used as a raw material in the next reaction step such as a hydrogenation reaction or an oxidation reaction. Can be used as an organic solvent solution. When the basic compound and / or the epoxy compound have an adverse effect in the next reaction step, they may be used as a raw material after removing them by a conventional method such as distillation.

[0032]

EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.

Example 1 Internal Volume 300 with Gas Inlet and Sampling Port
ml of a magnetically stirred autoclave with hydrogen / carbon monoxide =
After replacement with a 1/1 (molar ratio) mixed gas, 13 mg (0.05 mmol) of dicarbonylacetylacetonatotrodium, 348 mg (1 mmol) of lithium 3-diphenylphosphinobenzenesulfonate, 7-octene-
80 ml of 1-R (68 g, 0.54 mol) and N
20 ml of methylpyrrolidone was charged without contact with air, and the pressure inside the autoclave was kept at 50 atm with a mixed gas of hydrogen / carbon monoxide = 1/1 (molar ratio). The internal temperature was raised to 100 ° C. while stirring, and the reaction was carried out for 5 hours in this state. When the obtained reaction mixture was analyzed by gas chromatography, the conversion of 7-octen-1-al was 98%, and 1,9-nonandial and 2-methyl-1,8-octanediol were combined. 80g (0.5
(1 mol) (hydroformylation selectivity: 97)
%).

The reaction mixture obtained above was withdrawn without contact with air, and 20 ml of sufficiently degassed water was removed.
And the catalyst component and N-methylpyrrolidone were extracted and removed from the aqueous layer by vigorous shaking at room temperature.
An organic layer containing -nonandial and 2-methyl-1,8-octanedial (hydroformylation product) was obtained. Titration analysis of the obtained organic layer with an aqueous sodium hydroxide solution revealed that the organic layer contained an acidic substance at a concentration of 0.15 mN. 20 ml of this organic layer (1,9-nonandial and 2-methyl-1,
Containing 0.109 mol of 8-octanedials) at room temperature with 1.21 m of triethylamine.
g (0.012 mmol, amount equivalent to 4 gram equivalent to 1 gram equivalent of the above-mentioned acidic substance) was added, and the mixture was allowed to stand at 60 ° C. for 48 hours under a nitrogen atmosphere. The total amount of 1,9-nonandial and 2-methyl-1,8-octanedial in the layer was 0.104 mol, indicating that 96% of the initial amount remained.

COMPARATIVE EXAMPLE 1 In Example 1, an organic layer containing 1,9-nonandial and 2-methyl-1,8-octanedial was added at 60 ° C. for 48 hours without adding triethylamine. Analysis by chromatography revealed that 1,9-nonandial in the organic layer and 2-methyl-1,8-
The total amount of octanedial was 0.056 mol, leaving only 51% of the original amount.

Examples 2 to 9 and Comparative Examples 2 to 6 In Example 1, the compounds shown in Table 1 were used in place of triethylamine in the amounts shown in Table 1, and the temperature and time for storing the organic layer were changed. The same operation as in Example 1 was performed, except for changing as shown in Table 1. The residual ratio (%) of the initial hydroformylation products (1,9-nonandial and 2-methyl-1,8-octanedial) was calculated by analyzing by gas chromatography. The results are shown in Table 1.

[0037]

[Table 1]

Table 1 also shows the results of Example 1 and Comparative Example 1 described above. Also, as the above storage conditions,
48 hours at 60 ° C is about 7 when converted to room temperature (25 ° C).
It corresponds to 20 hours (about 30 days), and it is estimated that 2 hours at 80 ° C. also corresponds to about 120 hours when converted to room temperature (25 ° C.).

[0039]

According to the preservation method of the present invention, a hydroformylation product obtained in a form contained in an organic layer from a hydroformylation reaction mixture of an olefinic compound catalyzed by a water-soluble rhodium compound is purified. It can be stored stably without any operation.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI C07C 45/50 C07C 45/50 (72) Inventor Yoshihiro Tokuda 2045, Sazu, Kurashiki-shi, Okayama Prefecture 1 Kuraray Co., Ltd. (72) Invention Shigeaki Suzuki 1-12-39 Umeda, Kita-ku, Osaka-shi, Osaka Inside Kuraray Co., Ltd.

Claims (2)

[Claims] 1. An olefinic compound comprising: (a) a rhodium compound; (b) an alkali metal salt or an alkaline earth metal salt of a tertiary organic phosphorus compound having a sulfonic acid group (—SO ₃ H); A) A method for preserving a hydroformylation product obtained by reacting hydrogen and carbon monoxide in the presence of a polar organic compound, wherein the hydroformylation product is contained in an organic layer from a hydroformylation reaction mixture of the olefinic compound. A method for storing a hydroformylation product of an olefinic compound, the method comprising storing the organic layer in the presence of a basic compound and / or an epoxy compound. 2. The method according to claim 1, wherein the hydroformylation reaction mixture is subjected to an extraction operation with water to obtain a hydroformylation product in a form contained in an organic layer.