JP2000290236A - Production of tertiary diamine - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for simply producing a tertiary diamine, industrially advantageously, that has little small and shows good catalytic activity in the polyurethane production and is represented by formula I: RR'N-CH2-X- CH2-NRR' (X is a 6-10C divalent saturated hydrocarbon group; R and R' are each a saturated hydrocarbon group; R and R' may be incorporated into a divalent hydrocarbon group which may include oxygen atom(s) in the carbon chain). SOLUTION: A dialdehyde represented by formula II (X is defined as stated above) is reacted with a secondary diamine represented by formula III: HNRR' (R and R' are defined as stated above) or its salt to form a dienamine and the resultant dienamine is reduced. In another case, the dialdehyde of formula II and the secondary amine of formula III or its salt and hydrogen are reacted with one another in the presence of a hydrogenation catalyst.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a method for producing a tertiary diamine and a novel tertiary diamine produced by the method. The tertiary diamine obtained by the production method of the present invention is useful as a catalyst for producing a polyurethane by reacting a polyol component and a polyisocyanate component.

[0002]

2. Description of the Related Art Conventionally, as a catalyst for producing a polyurethane by reacting a polyol component and a polyisocyanate component, for example, N, N, N ', N'-tetramethylethylenediamine, N, N, N', N '-Tetramethylpropane-1,3-diamine, N, N, N', N'-tetramethylhexanediamine, N, N, N ', N'-tetramethylnonanediamine, N, N'-dimethylpiperazine, Tertiary amines such as N-methylmorpholine have been used. Japanese Patent Application Laid-Open No. 7-90040 discloses a catalyst having a low-irritant odor and having a good catalytic activity.
N, N, N ′, N′-tetramethyloctanediamine,
N, N, N ′, N′-tetramethylnonanediamine,
N, N, N ′, N′-tetramethyldecanediamine,
Tertiary diamines such as N, N, N ', N'-tetramethylundecanediamine and N, N, N', N'-tetramethyldodecanediamine have been proposed, among which N, N, N ', N '-Tetramethylnonanediamine is preferred.

[0003]

Problems to be Solved by the Invention Japanese Patent Laid-Open No. 7-90040
The publication describes that the tertiary diamine can be produced by reductive methylation of a primary diamine such as 1,9-nonanediamine or by reaction of a diol such as 1,9-nonanediol with dimethylamine. In the examples, copper, nickel supported on synthetic zeolite,
A specific example is a method for producing N, N, N ′, N′-tetramethylnonanediamine, which comprises reacting a mixed gas of 1,9-nonanediol, dimethylamine and hydrogen using a palladium three-way catalyst. It has been disclosed. However, in the production method described in this example, preparation of the catalyst is complicated. The present invention has been made in view of the above prior art, and is based on tertiary tertiary compounds such as N, N, N ', N'-tetramethylnonanediamine which are considered to be preferable in JP-A-7-90040. It is an object of the present invention to provide a method for producing a diamine conveniently and industrially advantageously. Another object of the present invention is to provide a novel tertiary diamine useful as a catalyst for producing a polyurethane by reacting a polyol component and a polyisocyanate component.

[0004]

According to the present invention, one of the above-mentioned problems is represented by the following expression (2).

[0005]

Embedded image

In the formula, X represents a divalent saturated hydrocarbon group having 6 to 10 carbon atoms, and a dialdehyde represented by the formula (3) HRRR '(3) (wherein R and R' Represents a saturated hydrocarbon group.
R and R 'may be taken together to represent a divalent saturated hydrocarbon group which may contain an oxygen atom in the carbon chain. ) With a secondary amine or dienamine obtained by reacting a salt thereof (hereinafter represented simply consists of reducing the sometimes abbreviated as dienamine), formula (1) RR'N-CH ₂ -X- CH ₂ —NRR ′ (1) (wherein, X, R and R ′ are as defined above)
Is solved by providing a method for producing a tertiary diamine represented by the following formula (hereinafter, may be abbreviated as production method 1). Further, in the presence of a hydrogenation catalyst, a dialdehyde represented by the above formula (2), a secondary amine represented by the above formula (3) or a salt thereof and hydrogen are reacted, and the above formula ( Production method of tertiary diamine shown in 1) (hereinafter, may be abbreviated as production method 2)
Is also solved by providing.

Further, according to the present invention, another one of the above-mentioned problems is represented by the following formula (5).

[0008]

Embedded image

(In the formula, R and R ′ represent a saturated hydrocarbon group. R and R ′ may be taken together to form a divalent saturated hydrocarbon which may contain an oxygen atom in the carbon chain. This may be achieved by providing a tertiary diamine represented by the formula:

[0010]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS First, a manufacturing method 1 will be described. In the production method 1, in formula (2) representing a dialdehyde used as a starting material, X has 6 carbon atoms.
The divalent saturated hydrocarbon group of 10 to 10 may be linear or branched, for example, a hexamethylene group, a heptamethylene group, an octamethylene group, a formula-(CH ₂ ) _5-
CH (CH ₃₎ - and a group represented by the like.

Specific examples of the dialdehyde represented by the formula (2) include 1,8-octanediol, 1,9-nonandial, 2-methyl-1,8-octanedial,
1,10-decandial and the like. Equation (2)
As the dialdehyde represented by, one type may be used, or a mixture of two or more types may be used as desired. As the dialdehyde represented by the formula (2),
Those having 9 carbon atoms, and among them, 1,9-nonandial and / or 2-methyl-1,8-octanedial are preferable because they are inexpensive compounds.

The dialdehyde represented by the formula (2) is disclosed in, for example, JP-A-58-118535 and JP-A-58-1.
It can be produced according to a known method described in, for example, JP-A-57739 and JP-A-58-216138.

The second method used in the manufacturing method 1
In the formula (3) representing a primary amine, examples of the saturated hydrocarbon group represented by R and R ′ include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, Examples include a t-butyl group, an n-pentyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, and a 2-ethylhexyl group. Examples of the divalent saturated hydrocarbon group which may contain an oxygen atom in the carbon chain, represented by R and R ′ as one, include a tetramethylene group, a pentamethylene group,
Formula _{-CH 2 -CH 2 -O-CH 2} -CH 2 below - and a group represented by the like. These saturated hydrocarbon groups or divalent saturated hydrocarbon groups which may contain an oxygen atom in the carbon chain preferably have 8 or less carbon atoms.

Specific examples of the secondary amine represented by the formula (3) include dimethylamine, N-ethylmethylamine,
Diethylamine, N-methylpropylamine, N-methylisopropylamine, N-methyl-n-butylamine, N-methyl-tert-butylamine, N-ethylpropylamine, N-methylisopropylamine, dipropylamine, diisopropylamine, N -Ethylbutylamine, N-methylhexylamine, N-propylbutylamine, di-n-butylamine, di-sec-butylamine, di-tert-butylamine, diisobutylamine, dipentylamine, di-n-hexylamine,
Di-n-octylamine, bis (2-ethylhexyl)
Examples include amine, dicyclohexylamine, pyrrolidine, piperidine, morpholine and the like. Further, specific examples of the salt of the secondary amine represented by the formula (3) include the hydrochloride and sulfate of those exemplified above.

In the production method 1, the secondary amine represented by the formula (3) or the salt thereof is used in an amount of usually 0.5 to 10 mol, preferably 0.5 to 10 mol, per mol of the dialdehyde represented by the formula (2). 0.8-5 mol, more preferably 0.9
モ ル 3 mol.

In the production method 1, in the reaction of the dialdehyde represented by the formula (2) with the secondary amine represented by the formula (3) or a salt thereof, for example, potassium carbonate, p-toluenesulfonic acid, acetic acid, ion A catalyst used in ordinary enamine synthesis such as an exchange resin, zinc chloride, titanium chloride, phosphoryl chloride, and boron trifluoride may be used. The amount of the catalyst used is based on the dialdehyde represented by the formula (2).
The weight is usually 0.1 times or less, preferably 0.05 times or less.

The reaction between the dialdehyde represented by the formula (2) and the secondary amine represented by the formula (3) or a salt thereof is as follows:
Although the reaction can be carried out in the absence of a solvent, the reaction is preferably carried out in the presence of a solvent that does not adversely influence the reaction. Examples of usable solvents include, for example, methanol, ethanol, n-propanol, 2-propanol, n-
Alcohols such as butanol; hydrocarbons such as hexane, heptane, benzene, toluene, and xylene; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; N, N-dimethylformamide, dimethyl sulfoxide and the like Polar aprotic solvents; water and the like. The amount of the solvent used is usually 10 times or less the weight of the dialdehyde represented by the formula (2). The solvent is 1
One type may be used, or two or more types may be used in combination.

The reaction between the dialdehyde represented by the formula (2) and the secondary amine represented by the formula (3) or a salt thereof is as follows:
Usually, it is carried out at -20 to 200C, preferably at 20 to 150C.

In the reaction between the dialdehyde represented by the formula (2) and the secondary amine represented by the formula (3) or a salt thereof, the reaction is carried out while removing water produced as a by-product of the reaction. You may. Examples of the method for removing water include a method for removing water by azeotropy using a solvent such as toluene, a method for using a dehydrating agent such as molecular sieves, anhydrous magnesium sulfate, and anhydrous sodium sulfate. Known methods can be used.

After completion of the reaction, the resulting dienamine can be separated and obtained by a known method such as a method of distilling the reaction mixture after removing the catalyst if necessary.

In the production method 1, by reducing the dienamine thus obtained, the desired formula (1)
To produce a tertiary diamine represented by the formula: The reaction mixture obtained by the reaction of the dialdehyde represented by the formula (2) with the secondary amine represented by the formula (3) or a salt thereof may be used as it is as a raw material to be subjected to the reduction. .

The reduction of dienamine can be carried out according to a known method, but is preferably carried out by hydrogenation in the presence of a hydrogenation catalyst. In the hydrogenation, a catalyst conventionally used in hydrogenation of enamine can be used, and examples thereof include palladium carbon, Raney nickel, and ruthenium catalysts. The amount of the catalyst used is usually 1 to dienamine.
0% by weight or less, preferably 5% by weight or less.

In the hydrogenation, the pressure of hydrogen used is preferably in the range of normal pressure to 80 atm.
A pressure range is more preferred.

The reduction of dienamine can be carried out in the absence of a solvent, but is preferably carried out in the presence of a solvent which does not adversely influence the reaction. Examples of usable solvents include alcohols such as methanol, ethanol, n-propanol, 2-propanol and n-butanol; hydrocarbons such as hexane, heptane, benzene, toluene and xylene; ethers such as diethyl ether and tetrahydrofuran; Dichloromethane, dichloroethane,
Halogenated hydrocarbons such as chloroform; polar aprotic solvents such as N, N-dimethylformamide and dimethylsulfoxide; and water. The amount of the solvent used is usually 10 times or less the weight of dienamine. In addition, one type of solvent may be used, or two or more types may be used in combination.

The reduction of dienamine is usually carried out at -20 to 20.
It is carried out at 0 ° C, preferably at 20 to 150 ° C.

After completion of the reaction, the obtained tertiary diamine represented by the formula (1) can be separated and obtained by a known method such as a method of distilling the reaction mixture after removing the catalyst if necessary. it can.

Next, the manufacturing method 2 will be described. The dialdehyde represented by the formula (2) and the secondary amine represented by the formula (3) or a salt thereof used in the production method 2 are the same as those described in the production method 1.
Further, the amount of the secondary amine represented by the formula (3) or a salt thereof is also the same as in the production method 1.

The hydrogenation catalyst used in the production method 2 may be the same as that used in the hydrogenation of dienamine in the production method 1. Examples of the hydrogenation catalyst include palladium carbon, Raney nickel and ruthenium catalysts. Is mentioned. The amount of the catalyst to be used is generally 10% by weight or less, preferably 5% by weight or less, based on the aldehyde represented by the formula (2).

In the hydrogenation, the pressure of hydrogen used is preferably in the range of normal pressure to 80 atm.
A pressure range is more preferred.

The reaction according to Production method 2 can be carried out in the absence of a solvent, but is preferably carried out in the presence of a solvent that does not adversely influence the reaction. Examples of usable solvents include alcohols such as methanol, ethanol, n-propanol, 2-propanol and n-butanol; hexane, heptane, benzene, toluene,
Hydrocarbons such as xylene; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as dichloromethane, dichloroethane and chloroform; polar aprotic solvents such as N, N-dimethylformamide and dimethylsulfoxide; and water. The amount of the solvent used is usually 10 to the dialdehyde represented by the formula (2).
It is less than double weight. In addition, one type of solvent may be used, or two or more types may be used in combination.

The reaction according to Production Method 2 is usually carried out at 20 to 2
It is carried out at 00C, preferably at 50 to 150C.

In the reaction according to Production method 2,
For example, a catalyst used in ordinary enamine synthesis, such as potassium carbonate, p-toluenesulfonic acid, acetic acid, an ion exchange resin, zinc chloride, titanium chloride, phosphoryl chloride, and boron trifluoride can be used. The amount of catalyst used is
It is usually at most 10% by weight, preferably at most 5% by weight, based on the dialdehyde represented by the formula (2).

In the reaction according to the production method 2, the components required for the reaction may be collectively charged into a reaction vessel,
The dialdehyde represented by the formula (2) may be continuously or intermittently added to a mixture of the secondary amine represented by the formula (3) or a salt thereof and the hydrogenation catalyst under a hydrogen atmosphere.
The latter method of continuously or intermittently adding the dialdehyde represented by the formula (2) is preferred.

After completion of the reaction, the obtained tertiary diamine represented by the formula (1) can be separated and obtained by a known method such as a method of distilling a reaction mixture after removing a catalyst if necessary. it can.

According to the production method 1 or 2, for example, N, N,
N ′, N′-tetramethylnonanediamine (when 1,9-nonandial is used as the dialdehyde represented by formula (2)), N, N, N ′, N′-tetramethyldecanediamine (formula (2) ), When 1,10-decandial is used), N, N,
Formulas such as N ', N'-tetramethyl-2-methyl-1,8-octanediamine (when 2-methyl-1,8-octanedial is used as the dialdehyde represented by the formula (2)); The tertiary diamine represented by (1) is obtained. In addition, among the tertiary diamines represented by the formula (1), in the case of using 2-methyl-1,8-octanedial as the dialdehyde represented by the formula (2), The tertiary diamine shown is a novel compound.

The tertiary diamine represented by the formula (1) is useful as a catalyst for producing a polyurethane by reacting a polyol component with a polyisocyanate component.

Here, as the polyol component, polyols which have been conventionally used in the production of polyurethane can be used. For example, polyester polyols, polyether polyols, polycarbonate polyols, acrylic polyols, hydroxyl group-containing diene-based polyols can be used. Polymer polyols such as polymers; ethylene glycol,
1,3-propanediol, 1,4-butanediol,
1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, xylylene glycol, neopentyl glycol,
Low molecular polyols such as glycerin are exemplified. As the polyol component, one kind may be used, or two or more kinds may be used in combination. Also, if necessary,
A low molecular compound having an active hydrogen atom such as 3,3-dichloro-4,4′-diaminophenylmethane, isophoronediamine, 4,4′-diaminodiphenylmethane, hydrazine, and dihydrazide may be used in combination.

As the polyisocyanate component,
Any polyisocyanate conventionally used in the production of polyurethanes can be used, for example,
4,4′-diphenylmethane diisocyanate, tolylene diisocyanate, phenylene diisocyanate,
1,5-naphthylene diisocyanate, 3,3′-dichloro-4,4′-diphenylmethane diisocyanate,
Aromatic diisocyanates such as xylylene diisocyanate and toluylene diisocyanate; hexamethylene diisocyanate, isophorone diisocyanate, 4,4 ′
-Aliphatic or alicyclic diisocyanates such as dicyclohexylmethane diisocyanate and hydrogenated xylylene diisocyanate. As the polyisocyanate component, one type may be used, or two or more types may be used in combination.

In the production of the polyurethane, the amount of the tertiary diamine represented by the formula (1) is usually 0.01 to 10% by weight, preferably 0.1 to 5% by weight, based on the whole raw materials. It is. As the tertiary diamine represented by the formula (1), one kind may be used, and
More than one species may be used in combination.

As a method for producing the polyurethane, any of the known urethane reaction techniques can be used, and either a prepolymer method or a one-shot method may be used. The molar ratio of active hydrogen atoms to isocyanate groups in the components is from 1: 1 to 1: 1.
After adding the polyisocyanate component in an amount of 5 and stirring for a short time, for example, heating to 50 to 160 ° C. to produce a polyurethane. A mixture of the polyol component and the polyisocyanate component is heated to, for example, 180 to 260 ° C. A method of kneading at a high temperature to produce a polyurethane, a polyol component and a polyisocyanate component are continuously supplied to an extruder such as a multi-screw extruder, for example, and a continuous melt polymerization is performed at a high temperature of 180 ° C. to 260 ° C. And a method in which a polyurethane component is reacted with a polyol component and a polyisocyanate component in an organic solvent. Among them, the tertiary diamine represented by the formula (1) has a feature that the odor derived from the catalyst component is small when the polyurethane is produced by the above method or the above method.

Also, in the production of polyurethane using a tertiary diamine represented by the formula (1) as a catalyst, the tertiary diamine represented by the formula (1), which is usually used in the production of polyurethane, is different. Optional components such as a catalyst, a reaction accelerator, a foaming agent, an internal release agent, a filler, a reinforcing agent, a dye, a pigment, an ultraviolet absorber, and a stabilizer can be used as needed.

The polyurethane obtained by the above method is used for sheets, films, foams, rolls, gears, solid tires, belts, hoses, tubes, packing materials, vibration insulators, shoe soles, sports shoes, machine parts, and building materials. It can be used for a wide range of applications, such as automotive parts, furniture, linings, sealing materials, waterproof materials, sports goods, elastic fibers, artificial leather, fiber treatment agents, adhesives, coating agents, various binders, and paints.

[0043]

EXAMPLES The present invention will be described below in more detail with reference to examples, but the present invention is not limited to these examples. In the following Examples and Comparative Examples, the reaction yield and the purity were all measured by the column G-100 manufactured by Chemical Inspection Association.
This is a value calculated based on the peak area ratio of gas chromatography using (trade name).

Example 1 221 g of a dimethylamine aqueous solution (concentration: 50% by weight), 221 g of toluene, 1.9 g of p-toluenesulfonic acid monohydrate and 1.9 g of palladium carbon were placed in a pressure-resistant reaction vessel.
56 g was charged, and under a hydrogen atmosphere at a pressure of 0.5 MPa,
While stirring at 80 ° C., 1,9-nonandial and 2-
156 g of a mixture of methyl-1,8-octanedial (former / latter = 72/28) were added continuously over 2 hours. The reaction was almost completed when the addition of the mixture of 1,9-nonandial and 2-methyl-1,8-octanedial was completed, but the mixture was further stirred at the same temperature for 2 hours to complete the reaction. During this time, hydrogen consumed in the reaction was appropriately supplied to the reaction vessel to maintain the hydrogen pressure at 0.5 MPa. The yield of the desired tertiary diamine is 99.7%.
Met. The obtained reaction mixture was taken out, and after separating and removing the aqueous layer and palladium carbon, the obtained organic layer was concentrated under reduced pressure. The obtained concentrated liquid was distilled under reduced pressure, and N,
N, N ', N'-tetramethyl-2-methyl-1,8-
38.4 g of octanediamine (purity: 99.4%, boiling point: 101 ° C./2 mmHg) and N, N, N ′, N ′
182 g of tetramethyl-1,9-nonanediamine (purity: 99.9%, boiling point: 107 ° C./2 mmHg) were obtained.

Example 2 In Example 1, a mixture of 1,9-nonandial and 2-methyl-1,8-octanedial (former / latter =
The tertiary diamine was produced in the same manner as in Example 1 except that 135 g of 57/43) was used. The yield of the target tertiary diamine was 99.7%. After taking out the obtained reaction mixture and separating and removing the aqueous layer and palladium carbon, the obtained organic layer was purified by simple evaporation to give N, N, N ', N'-tetramethyl-2.
-Methyl-1,8-octanediamine and N, N, N ',
A mixture of N′-tetramethyl-1,9-nonanediamine (N, N, N ′, N′-tetramethyl-2-methyl-
1,8-octanediamine / N, N, N ', N'-tetramethyl-1,9-nonanediamine = 52/48) 17
1 g (purity: 99.5%) was obtained.

Reference Example 1 Kuraray polyol P-2010 [trade name, manufactured by Kuraray Co., Ltd .; polyester polyol, number average molecular weight: 200]
0] to 3.75 g of N, N,
100 ppm of N ′, N′-tetramethyl-2-methyl-1,8-octanediamine was added and at 50 ° C.
DI (4,4'-diphenylmethane diisocyanate)
By reacting with 30.0 g, polyurethane was produced.
The reaction rate constant at this time was calculated from the disappearance rate of the isocyanate. Table 1 shows the results.

Reference Example 2 N, N, N ', N'-tetramethyl-2-methyl-1,
The amount of 8-octanediamine added was Kuraray polyol P-
Polyurethane was produced in the same manner as in Reference Example 1 except that the amount was changed to 1000 ppm with respect to 2010, and the reaction rate constant was calculated. Table 1 shows the results.

Reference Examples 3 to 8 Polyurethane was produced in the same manner as in Reference Example 1 except that the type and amount of the tertiary diamine used were as shown in Table 1, and the reaction rate constant was calculated. The results are shown in Table 1.

[0049]

[Table 1]

Example 3 A reactor was charged with 77.5 g of dibutylamine and 77.5 g of toluene.
g and 0.4 g of p-toluenesulfonic acid monohydrate, and 1,9-nonandial was added under reflux of toluene.
-Methyl-1,8-octanedial mixture (1,9
-Nonandial and 2-methyl-1,8-octanedial = 52/48) were added dropwise over 1 hour. At this time, generated water was removed from the reaction system as an azeotrope with toluene. The obtained azeotropic mixture of water and toluene was separated into water and toluene using a water separator, and the toluene was returned to the reaction system. After completion of the dropwise addition of the mixture of 1,9-nonandial and 2-methyl-1,8-octanedial, the mixture was refluxed for another 2 hours, and the obtained reaction solution was treated with a 5% aqueous sodium hydrogen carbonate solution, water and saturated saline. After successive washings, concentration under reduced pressure gave the corresponding dienamine.

38 g of the concentrate obtained above and toluene 5
2 g and 0.9 g of palladium carbon were charged into a pressure-resistant reactor, and stirred at 80 ° C. for 3 hours under a hydrogen atmosphere at a pressure of 0.5 MPa. During this time, hydrogen consumed in the reaction was appropriately supplied to the reaction vessel to maintain the hydrogen pressure at 0.5 MPa. The target tertiary diamine yield was 80.2%.

[0052]

According to the present invention, a tertiary diamine represented by the above formula (1), which has a low odor and a good catalytic activity in the production of polyurethane, can be produced simply and industrially advantageously. Can be.

 ──────────────────────────────────────────────────続 き Continued on front page F term (reference) 4G069 AA02 AA03 AA08 BA08B BB03B BC70B BC72B CB06 CB77 DA05 4H006 AA01 AA02 AB40 AC11 AC52 BA61 BD70 BE20 4H039 CA10 CA71 CD10 CD40

Claims (4)

[Claims] (1) Formula (2) (Wherein X represents a divalent saturated hydrocarbon group having 6 to 10 carbon atoms) and a dialdehyde represented by the formula (3) HNRR ′ (3) (wherein R and R ′ are saturated hydrocarbon groups) Represents a hydrogen group,
R and R 'may be taken together to represent a divalent saturated hydrocarbon group which may contain an oxygen atom in the carbon chain. RR′N—CH ₂ —X—CH ₂ —NRR ′ (1) comprising reducing a dienamine obtained by reacting a secondary amine represented by the following formula or a salt thereof: X, R and R ′ are as defined above)
A method for producing a tertiary diamine represented by the formula: 2. Formula (2) in the presence of a hydrogenation catalyst (Wherein X represents a divalent saturated hydrocarbon group having 6 to 10 carbon atoms), a formula (3) HNRR ′ (3) (wherein R and R ′ are saturated hydrocarbons) Represents a group,
R and R 'may be taken together to represent a divalent saturated hydrocarbon group which may contain an oxygen atom in the carbon chain. (1) RR′N—CH ₂ —X—CH ₂ —NRR ”(1) wherein X, R and R ′ Is as defined above)
A method for producing a tertiary diamine represented by the formula: 3. A dialdehyde represented by the formula (2):
1,9-nonandial and / or 2-methyl-
The production method according to claim 1 or 2, wherein the production method is 1,8-octanedial. 4. Formula (5) (Wherein, R and R ′ represent a saturated hydrocarbon group.
R and R 'may be taken together to represent a divalent saturated hydrocarbon group which may contain an oxygen atom in the carbon chain. A tertiary diamine represented by).