JPH05140051A - Tertiary amino-alcohol containing hydroxyl group at one end and its production - Google Patents

Abstract

PURPOSE:To obtain a new compound useful as an emulsifying agent, an epoxy curing agent, a urethane catalyst, an extractant, a lubricating oil an additive, etc. CONSTITUTION:A compound of the formula (R is 2-24C alkylene, cycloalkylene, arylene, aralkylene, etc.; R' is 1-24C alkyl, aryl or aralkyl; (n) is 2-50). The compound is obtained by reacting a diol or a dialdehyde with a primary amine in the presence of a catalyst having a composition which comprises copper-a transition metal element of the fourth period-a platinum element of the group 8 and may contain an alkali metal or an alkaline earth metal and by selectively tertiary aminating one of hydroxyl groups at molecular ends and the compound is applicable to wide uses by introducing the compound to a quaternary ammonium salt, a benzalkonium salt, carbobetaine, amine oxide, etc.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention provides a novel tertiary amino alcohol having a hydroxyl group at one end, which is an emulsifier, an epoxy curing agent, a urethane catalyst, and a flotation device. It is used as a drug, an extractant, a lubricant additive, and the like, and can be applied to various uses by introducing a derivative such as a quaternary ammonium salt, a benzalkonium salt, carbobetaine, and amine oxide. Further, it is possible to obtain various derivatives by taking advantage of the characteristic that one end is an alcohol and modifying it, for example, esterifying, sulfating, phosphating, aminating or halogenating.

[0002]

2. Description of the Related Art An amino alcohol having a tertiary amino group in its main chain and a hydroxyl group at one end as in the present invention and a method for easily producing the amino alcohol have not been found in any conventionally known publications.

For example, as a method for producing a polyamine having amino groups at both terminals by reacting a diol with NH ₃ , JP-A-61-278528 (Texaco Co., Ltd.) and JP-A-62-51646 (W. Grace and Company), and a method for producing a tertiary amine by a condensation reaction of a di-secondary amine and a di-aryl iodide compound is described in Japanese Examined Patent Publication No. 1-29818 (Xerox Corporation). There is. Further, a method for producing a polyalkylene polyamine by co-condensation of lower diamine and hexamethylene diamine is disclosed in Japanese Examined Patent Publication No. 62-31009 (Nippon Petroleum).
It is known by the company. A method for producing a polyamine by a dehydration condensation reaction between a cyclic amine and a diol is disclosed in Japanese Patent Publication No.
-288847 (The Dow Chemical Company). As a derivative of polyamine, a method of obtaining a polycation by reacting a ditertiary amine with a dihalide is described in JP-B-61-37242 and JP-B-61-37243 (L'Oreal).

The tertiary amino alcohol defined by the general formula (I) of the present invention in which a tertiary amino group is incorporated into the skeleton and a terminal of one of the molecules is a hydroxyl group is completely novel,
Further, a method for easily producing such a tertiary amino alcohol having a hydroxyl group at one terminal has not been found in any conventionally known publication.

[0005]

As described above, the tertiary amino alcohol having a tertiary amino group in the main chain skeleton and having a hydroxyl group at one end of the molecule and an effective production method thereof are still unclear. Disclosure has not been made. If it is possible to easily produce such a tertiary amino alcohol having a hydroxyl group at one end, it is possible to develop applications as amines and amine derivatives different from conventional ones.
It is expected that the unique characteristics will be created by the polymerization of the skeleton containing the primary amino group, and that new fields of amine applications will be opened up.

[0006]

The present inventors have completed the present invention as a result of intensive studies in view of the present situation.

That is, the present invention has the general formula (I)

[0008]

[Chemical 3]

[Wherein, R is the same or different carbon number 2 to
24 linear or branched alkylene group, alicyclic alkylene group, cycloalkylene group, arylene group, aralkylene group, or-(CH ₂ CH ₂ O) _p- (CH ₂ CH ₂ ) _q- (where p is 0 or a positive number, and q is a positive number), and R ′ is the same or different linear or branched alkyl group having 1 to 24 carbon atoms,
It represents an aryl group or an aralkyl group, and n represents a positive number of 2 to 50. ] In producing the tertiary aminoalcohol having a hydroxyl group at one end and a tertiary aminoalcohol having a hydroxyl group at one end thereof, copper-fourth period transition metal element-group 8 platinum group element The present invention provides a method for producing a tertiary amino alcohol having a hydroxyl group at one end, which uses a catalyst having a composition which is composed of and which may contain an alkali metal or an alkaline earth metal. Here, the aralkyl group means an alkyl group having an aromatic ring such as a benzyl group and a phenethyl group. Further, the aralkylene group of R'is a divalent group obtained by removing one hydrogen atom from the aralkyl group.

In the production method of the present invention, a diol or dialdehyde and a primary amine are reacted in the presence of the above-mentioned specific three-way or four-way catalyst to continuously advance the tertiary amination, First, a tertiary amino alcohol having hydroxyl groups at both ends is obtained, and then a tertiary amino alcohol having hydroxyl groups at both ends and a secondary amine are added in the presence of the specific three-way or four-way catalyst as described above. And selectively tertiary aminated one of the hydroxyl groups at the terminal of the molecule to give the tertiary amino alcohol of the present invention having a tertiary amino group in the main chain and a hydroxyl group at one terminal of the molecule. A method of manufacturing is provided.

As the diol or dialdehyde used in the present invention, a linear or branched one having 2 to 24 carbon atoms is used. For example, 1,3-butanediol, 1,
4-butanediol, 1,5-pentanediol, 1,
6-hexanediol, 1,9-nonanediol, 1,
10-decanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,4-
Examples thereof include cyclohexanedimethanol, bisphenol A ethylene oxide adduct, hydroquinone and the like, and corresponding dialdehydes and the like.

Examples of the primary amine used in the present invention include linear or branched primary amines having 1 to 24 carbon atoms or aromatic amines such as methylamine, propylamine, isopropylamine and butylamine. , 2-
Examples thereof include ethylhexylamine, heptylamine, octylamine, decylamine, dodecylamine, cetylamine, stearylamine, docosylamine, oleylamine, benzylamine, phenethylamine and aniline.

Examples of the secondary amine used in the present invention include those represented by the general formula of formula R'R'NH, wherein R'is the same or different straight or branched chain. It is a hydrocarbon group having 1 to 24 carbon atoms or an aromatic group. Examples thereof include dimethylamine, dibutylamine, didodecylamine, dibenzylamine and the like. Also, the second with different R '
Examples of the primary amine include stearyl oleyl amine and methyl ethyl amine.

Usually, as a tertiary amination technique, a Japanese patent publication
57-549, JP-B-59-12106, JP-A-57-55704,
Japanese Patent Publication 60-1297 (Hoechst), Japanese Patent Publication 60-48499 (Shel
l), U.S. Pat.Nos. 4440403, 4404404, 4409399 (Onyx), JP 61-60636 (Shering),
JP-A-59-14457 (Texaco) and JP-B-62-28947
No. (New Japan Rika) and the like are disclosed, but these production methods are not sufficient. This is because the catalysts described therein do not have sufficient reactivity and the target product of the tertiary amino alcohol having an amino group at one end cannot be obtained in a sufficient yield. On the other hand, the catalyst used in the present invention is a catalyst composed of copper-the fourth period transition metal element-the group 8 platinum group element and having a composition which may contain an alkali metal or an alkaline earth metal. The desired tertiary amino alcohol can be obtained in a sufficient yield for the first time by the production method using the same.

The copper-fourth period transition metal element-group 8 platinum group element catalyst, the fourth period transition metal element is one selected from the group consisting of chromium, manganese, iron, cobalt, nickel and zinc. That is, the Group 8 platinum group element is at least one selected from the group consisting of platinum, palladium, ruthenium, and rhodium. Further, the molar ratio of copper to the metal of the 4th period transition metal element to the copper of the 4th period transition metal element-Group 8 platinum group element catalyst and the metal atom of the 4th period transition metal element is 1: 9 to 9: 1. And the Group 8 platinum group element has a molar ratio of 0.001 to 0.1 with respect to the total of copper and the fourth period transition metal element.

Copper, the fourth period transition metal element and the platinum group element are essential as the metal composition of the catalyst used in the present invention, but in addition to this, an alkali metal or an alkaline earth metal may be contained. Various forms can be selected for the catalyst compatible with.

That is, in the present invention, three components of copper, a fourth period transition metal element, and a Group 8 platinum group element, or an alkali metal or an alkaline earth metal (hereinafter referred to as the fourth component).
The effect of the interaction between these components is exhibited only when the four components including the above are present in the reaction system as a catalyst composition.

The catalyst used in the present invention has an essential catalytic function in the composition of the above-mentioned three components or four components, and comprises a diol or dialdehyde and a primary amine, or a tertiary amino alcohol having hydroxyl groups at both terminals. Upon reacting the secondary amine, the catalytic activity is exhibited only by the reduction operation of each metal component in a hydrogen atmosphere. Therefore, the difference in the form of the metal before the reduction operation and the state in the system after the reduction operation is not limited in the present invention, and copper, the fourth period transition metal element, and the Any form may be used as long as it is a group platinum group element or an interaction between these elements and the fourth component.

Therefore, the form of the metal suitable for the catalyst used in the production method of the present invention is as follows: 1) copper, the fourth period transition metal element, the Group 8 platinum group element, or these and the fourth component metal, or the metal thereof. In the form of being dispersed in a reaction medium such as oxides or hydroxides, and mixtures thereof. 2) Copper, a fourth component including a fourth component of the Group 4 platinum group element of the fourth period transition metal element on a suitable carrier,
A form in which they are supported on the same carrier and dispersed in the reaction medium. 3) Reaction as a complex stabilized with copper, a 4-component aliphatic carboxylic acid salt of 4 components including a 4th period transition metal element Group 8 platinum group element or a 4 component including a 4th component, or a suitable ligand A form in which it becomes a metal colloid in the medium and becomes a homogeneous system. 4) A mixture of 1) to 2) that is dispersed in the reaction medium and 3) that is uniform in the reaction medium, or is in a dispersed state before hydrogen reduction. It should have a uniform morphology after hydrogen reduction. Any of the above cases may be used as long as the three-component or four-component metal which is the essence of the catalyst used in the present invention exhibits an interaction between the components by the operation in a hydrogen atmosphere.

A more preferred form of the catalyst used in the present invention is to stabilize the catalytic metal, that is, to immobilize the active surface, and from the viewpoint of durability against catalyst poisoning substances. It is preferable that the particles are uniformly supported.

Copper of the present invention, 4th period transition metal element, 8th
4 including 3 component metals or 4th component of platinum group element
When the component metal is supported on a carrier, suitable carriers include those commonly used as a catalyst carrier, such as alumina, silica-alumina, diatomaceous earth, silica, activated carbon, natural and artificial zeolites. The amount of the catalyst metal supported on the carrier can be arbitrarily determined, but it is usually in the range of 5 to 70% by weight.

Various methods can be selected for supporting these three-component or four-component metals on the surface of the carrier. In this case, as the metal form of the catalyst raw material, copper, the fourth period transition metal element, the Group 8 platinum group element, the oxide of the fourth component, the hydroxide or various metal salts thereof can be used. Examples of the metal salt include copper, the fourth period transition metal element, the Group 8 platinum group element, and the chloride of the fourth component, sulfate, nitrate, acetate, and aliphatic carboxylate. In addition, these metal complexes, such as copper, the 4th period transition metal element, the acetylacetone complex of the Group 8 platinum group element and the dimethylglyoxime complex, and the carbonyl complex, amine complex, phosphine complex of the Group 8 platinum group element. Etc. can also be used.

When a catalyst is produced by a method of supporting a metal on a carrier using these metal raw material species, for example, copper, a 4th period transition metal element, a Group 8 platinum group element and a 4th group metal are used.
A method in which a carrier is put in a solution of an appropriate salt of the components, sufficiently impregnated, and then dried and baked (impregnation method), a carrier and copper,
After thoroughly mixing an aqueous solution of an appropriate salt of a periodic transition metal element or a Group 8 platinum group element, an alkaline aqueous solution such as sodium carbonate, sodium hydroxide or aqueous ammonia is added to precipitate the metal salt on the carrier, or After sufficiently mixing an aqueous solution of copper, an appropriate salt of a 4th period transition metal element, and a platinum group element of Group 8 with the water slurry of, the pH of the slurry is adjusted with an alkaline aqueous solution such as sodium carbonate, sodium hydroxide or aqueous ammonia. Simultaneously add them so that they become constant (for example, constant at pH = 7), precipitate the metal salt on the carrier, dry,
When calcining to prepare a copper-fourth period transition metal element-group 8 platinum group element to obtain a four-component catalyst, the obtained three-component catalyst is treated with an alkali metal salt or alkaline earth metal. A method of obtaining a four-component catalyst by putting it in an aqueous metal solution and thoroughly impregnating it, followed by drying and firing (the above combination of the coprecipitation method and the impregnation method), or a method of ion-exchange with hydrogen or metal contained in zeolite ( Any conventionally known method such as an ion exchange method) may be used. In the case of the coprecipitation method, after depositing the metal, wash it thoroughly with water, and dry it at around 100 ° C, then 300-70
The catalyst is obtained by calcining at 0 ° C.

In addition, in the above method, only copper or only copper and the fourth period transition metal element are supported on the carrier and subjected to the reaction, and the carrier or the aliphatic substance of the platinum group 8 element or the fourth component is supported. A method of adding a carboxylate or a complex to form a complex with copper, a fourth period transition metal element, a Group 8 platinum group element and a fourth component in a hydrogen atmosphere in a reaction medium is also effective.

The catalysts obtained by the above various methods are
More preferably, it is in a form in which three or four components are uniformly supported on the same carrier. The catalyst used in the present invention is essentially indispensable of the three components of copper, the fourth period transition metal element, and the Group 8 platinum group element.

The method for producing a tertiary amino alcohol having a hydroxyl group at one end according to the present invention will be described in more detail.

The production method of the present invention, that is, a diol or dialdehyde is reacted with a primary amine to obtain a tertiary amino alcohol having hydroxyl groups at both ends, and then this compound is reacted with a secondary amine. In producing the tertiary amino alcohol of the present invention having a hydroxyl group at one end,
Copper-nickel-group 8 platinum group element, copper-chromium-group 8 platinum group element, copper-zinc-group 8 platinum group element, copper-manganese-group 8 platinum group element, copper-iron-group 8 Using a catalyst having a composition of group platinum group element, copper-cobalt-group 8 platinum group element and the like, and a catalyst in which these catalysts further include a fourth component,
In the presence of these catalysts, first, a tertiary amino alcohol having hydroxyl groups at both ends is obtained, and then this compound is reacted with a secondary amine to obtain a third amino alcohol according to the present invention having a hydroxyl group at one end.
Higher grade amino alcohols can be produced. In this case, a tertiary amino alcohol having hydroxyl groups at both ends is produced at a temperature of about 150 to 250 ° C. in the reaction of a diol or dialdehyde and a primary amine, and a tertiary amino alcohol having hydroxyl groups at both ends is used. The purpose is achieved by carrying out the reaction between the amino alcohol and the secondary amine at a temperature of about 160 to 200 ° C.

When the primary amine and the secondary amine are gases, they may be blown continuously or intermittently during the reaction, or a predetermined amount may be blown at once under pressure. When the primary amine is a liquid, it may be charged continuously, or a predetermined amount may be charged from the beginning.

Here, the molar ratio of the primary amine to the diol or dialdehyde is 0.7 times or more, preferably 1
It is necessary to double the molar amount, and in the case of a gaseous amine, an excessively charged gas together with hydrogen may be recovered and recycled. The secondary amine is required to be 0.8 times or less, preferably 0.4 to 0.6 times the mole of the tertiary amino alcohol having hydroxyl groups at both ends, and in the case of a gaseous amine, the gas charged in excess with hydrogen is required. It may be recovered and reused by circulation.

In the production method of the present invention, water produced by the reaction between a diol or dialdehyde and a primary amine or the reaction between a hydroxyl group-terminated tertiary amino alcohol and a secondary amine is taken out of the reaction system. Is preferred. If the generated water is not taken out of the system, the catalytic activity and selectivity are often lowered.For example, when the reaction is carried out without removing the generated water, the disproportionation product of the amine increases, A large amount of condensate is produced and the yield of the tertiary amino alcohol is reduced.

The removal of water may be carried out continuously or continuously after the reaction is interrupted, and the produced water does not exist in the reaction system for a long time and may be appropriately removed. It is desirable to remove it. Specifically, it is common to introduce an appropriate amount of hydrogen gas into the reaction system during the reaction and distill the produced water together with the hydrogen gas.By concentrating and separating the produced water with a condenser, the hydrogen gas is circulated. It can also be used. It is also possible to add an appropriate solvent during the reaction and distill the produced water by azeotropic distillation with this solvent, or to add an inert solvent for the purpose of lowering the viscosity of the product.

In the present invention, a catalyst previously reduced with hydrogen gas may be used separately, or a catalyst before reduction is reacted with diol or dialdehyde as a reaction raw material and a tertiary amino alcohol having hydroxyl groups at both ends. When the hydrogen gas or the amine to be reacted is a gaseous amine, the catalyst can be reduced by introducing the mixed gas of hydrogen gas and gaseous amine and raising the temperature to the reaction temperature.

An example of the embodiment of the method for producing a tertiary amino alcohol of the present invention will be briefly described. In the case of using hydrogen and gaseous amine, use a tube for introducing the amine, and a reaction vessel equipped with a condenser and a separator for condensing / separating water and excess amine produced in the reaction and the oily substance distilled out. A raw material diol or dialdehyde and a catalyst are charged. The catalyst can be charged in any amount, but it is usually in the range of 1 to 10% by weight based on the charged diol or dialdehyde. After the system is replaced with nitrogen gas, the temperature rise is started while introducing hydrogen alone or a mixed gas of hydrogen and a small amount of gaseous primary amine. When using a liquid primary amine, the primary amine is added all at once after reaching a certain temperature, or
Alternatively, it is added little by little to the reaction system. The reaction temperature in this reaction is usually about 150 to 250 ° C., but a temperature outside this range can be set depending on the kind of raw material. The catalyst is reduced during this temperature rise to become an active catalyst. After reaching the predetermined temperature, the primary amine is introduced or dropped to start the reaction. Water produced during the reaction is discharged out of the reaction system together with a gaseous substance (hydrogen and excess gaseous amine) and a small amount of an oily substance, and separated from the oily substance through a condenser and a separator. The separated oily substance is returned to the reaction vessel.
By this reaction, a tertiary amino alcohol having hydroxyl groups at both ends is first obtained.

In the case of aminating one terminal of the tertiary aminoalcohol having hydroxyl groups at both terminals thus produced, the reaction temperature is 160 to 20 depending on the starting material.
By setting the temperature to 0 ° C., reacting the secondary amine as described above, and further setting the hydrogen introduction amount to 5 to 50 liters / hr · kg,
The tertiary amino alcohol of the present invention, which is selectively aminated at one end, is synthesized. If the reaction temperature exceeds 200 ° C, the amination of both terminals will proceed rapidly and the following general formula (II)

[0035]

[Chemical 4]

It is not preferable because the by-product represented by is increased. If the reaction temperature is lower than 160 ° C, the amination reaction rate is extremely slow, which is not preferable. The amount of hydrogen introduced is 5
If it is less than liter / hr · kg, a large amount of aldehyde condensate tends to be produced as a by-product, and if it exceeds 50 liter / hr · kg, the amination of both terminals proceeds rapidly, and the above general formula (II)
It is not preferable because by-products represented by are increased. Also,
The reaction time may be appropriately determined depending on the type of secondary amine, the reaction temperature, the amount of hydrogen introduced, and the like. For example, at 160 ° C., a mixed gas of dimethylamine and hydrogen gas is mixed with 10 liters / hr.
The reaction time when blowing into the reaction system at a flow rate of kg is about 3
It's about time.

After the completion of the reaction, various reaction products can be obtained by subjecting the reaction product to a distillation operation. As a result of analyzing the gaseous substances (excess hydrogen and gaseous amine), these gaseous substances contain almost no by-products (for example, hydrocarbons), and the use of a circulator allows these gases to be removed. The substance can be reused without special purification steps. After the reaction is completed, the catalyst is filtered by a suitable method to obtain a product.

[0038]

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

<Preparation of catalyst> A ternary catalyst of copper-fourth period transition metal element-group 8 platinum group element supported on synthetic zeolite was prepared as follows. A synthetic zeolite was charged into a 1-liter flask, and then copper nitrate, nickel nitrate, and palladium chloride were used in a molar ratio of each metal atom of Cu: Ni: Pd =
What was melt | dissolved in water so that it might become 4: 1: 0.1 was put, and it heated up, stirring. A 10% Na ₂ CO ₃ aqueous solution was gradually added dropwise at 90 ° C. After aging for 1 hour, the precipitate is filtered and washed with water to 80
After drying at ℃ for 10 hours, it was baked at 400 ℃ for 3 hours. The amount of the obtained metal oxide supported on the carrier was 50%.

Example 1 1,6-Hexanediol and monomethylamine were reacted. In a 1 liter flask equipped with a condenser and a separator for separating produced water, 600 g of 1,6-hexanediol and 24 g of the above catalyst (Cu / Ni / Pd catalyst 4/1 / 0.1 molar ratio) (vs. raw material) (Diol 4% by weight) was charged, the system was replaced with nitrogen while stirring, and the temperature rise was started. When the temperature in the system reached 100 ° C, hydrogen gas was blown into the system at a flow rate of 10 liter / Hr · kg using a flow meter to raise the temperature to 220 ° C. At this temperature, a mixed gas of monomethylamine and hydrogen gas was blown into the reaction system at a flow rate of 60 liters / hr · kg to carry out a reaction for about 4 hours. The reaction was followed by amine number. As a result, a viscous compound having the following structure having hydroxyl groups at both ends was obtained.

[0041]

[Chemical 5]

Subsequently, using the above catalyst, a mixed gas of dimethylamine and hydrogen gas was blown into the reaction system at a flow rate of 10 l / hr at 160 ° C. The conversion rate reached 85% in about 3 hours from the start of introduction. The reaction was controlled by hydroxyl number and gas chromatography and liquid chromatography. After the reaction was completed, the catalyst was separated by filtration to obtain a pale yellow liquid. Further, using a precision distillation apparatus, the tower top temperature of 210 ~
By separating and purifying under a distillation condition of 220 ° C (n = 2) and a pressure of 0.3 torr, the target one end has a hydroxyl group.
40.3% of a primary amino alcohol was obtained in an isolated yield based on 1,6-hexanediol.

Next, the obtained product was analyzed. In order to prove that the terminal of this product was an amino group and a hydroxyl group, ¹³ C-NMR spectrum, ¹ H-NMR spectrum and infrared absorption spectrum were measured and identified by 270 MHz-NMR (JNM-GX270WB). Each chart of the tertiary amino alcohol having a hydroxyl group at one end is shown in FIGS. Further, regarding the amine value, the measured total amine value was 435, which was in good agreement with the theoretical value of 435 when n was 2. The tertiary amine value was 432.5 (hydroxyl value 218). From these facts, it was confirmed that a tertiary amino alcohol having a structure shown below and having a hydroxyl group at one end was obtained.

[0044]

[Chemical 6]

[Brief description of drawings]

FIG. 1 shows the tertiary amino alcohol obtained in Example 1.
It is a figure which shows a ¹ H-NMR spectrum.

FIG. 2 shows the tertiary amino alcohol obtained in Example 1.
It is a figure which shows a ¹³ C-NMR spectrum.

FIG. 3 is a diagram showing an infrared absorption spectrum of the tertiary amino alcohol obtained in Example 1.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display location C07C 217/04 6742-4H // C07B 61/00 300

Claims (4)

[Claims] 1. A compound represented by the general formula (I): [In the formula, R is the same or different, a linear or branched alkylene group having 2 to 24 carbon atoms, an alicyclic alkylene group, a cycloalkylene group, an arylene group, an aralkylene group, or-(C
H ₂ CH ₂ O) _p- (CH ₂ CH ₂ ) _q- (where p is 0 or a positive number, and q
Is a positive number) and R'is the same or different carbon number 1
-24 is a linear or branched alkyl group, aryl group or aralkyl group, and n is a positive number of 2-50. ] A tertiary amino alcohol having a hydroxyl group at one end represented by the following formula. 2. A compound represented by the general formula (I): [In the formula, R is the same or different, a linear or branched alkylene group having 2 to 24 carbon atoms, an alicyclic alkylene group, a cycloalkylene group, an arylene group, an aralkylene group, or-(C
H ₂ CH ₂ O) _p- (CH ₂ CH ₂ ) _q- (where p is 0 or a positive number, and q
Is a positive number) and R'is the same or different carbon number 1
-24 is a linear or branched alkyl group, aryl group or aralkyl group, and n is a positive number of 2-50. ] In producing a tertiary amino alcohol having a hydroxyl group at one end represented by the formula, copper-fourth transition metal element-8th
A method for producing a tertiary amino alcohol having a hydroxyl group at one end, which uses a catalyst having a composition which is composed of a group platinum element and which may contain an alkali metal or an alkaline earth metal. 3. The fourth period transition metal element is at least one selected from the group consisting of chromium, manganese, iron, cobalt, nickel and zinc, and the Group 8 platinum group element is selected from platinum, palladium, ruthenium and rhodium. 1 selected from the group
The third group having a hydroxyl group at one end according to claim 2, which is more than one species
For producing high grade amino alcohol. 4. A copper-fourth period transition metal element-group 8 platinum group element catalyst, wherein the molar ratio of copper to the fourth period transition metal element metal atom is from 1: 9 to copper: fourth period transition metal element. 9: 1
4. The method for producing a tertiary amino alcohol having a hydroxyl group at one end according to claim 3, wherein the Group 8 platinum group element has a molar ratio of 0.001 to 0.1 with respect to the sum of copper and the fourth period transition metal element. ..