Method for producing n-alkylborazine compound

Abstract

The purpose of the present invention is to provide a method with which an N-alkylborazine compound can be obtained at a high yield. Provided is a method for producing an N-alkylborazine compound by reacting an alkali borohydride represented by ABH4 (A is a lithium atom, a sodium atom or a potassium atom) with an alkylamine salt represented by RNH3X (R is an alkyl group, and X is a halogen atom) in an organic solvent. The method is characterized in that the alkali borohydride and the alkylamine salt are reacted while applying a stirring power of 0.1-10 kW per 1 m3 of the total volume of the reaction liquid containing the alkali borohydride, the alkylamine salt and the organic solvent.

Description

Method for producing N-alkylborazine compound

[0001] The present invention relates to a method for producing an N-alkylborazine compound.

[0002] As information devices become more sophisticated, LSI design rules are becoming finer every year. In manufacturing LSIs with fine design rules, the materials that make up the LSIs must also be high-performance and able to function even on the fine LSIs.

[0003] For example, when it comes to materials used for interlayer insulating films in LSIs, a high dielectric constant can cause signal delay. This signal delay has a particularly large impact on miniaturized LSIs. Therefore, there has been a demand for the development of new low-dielectric materials that can be used as interlayer insulating films. Furthermore, to be used as an interlayer insulating film, materials must not only have a low dielectric constant, but also excellent properties such as moisture resistance, heat resistance, and mechanical strength.

[0004] To meet such demands, borazine compounds having a borazine ring skeleton in the molecule have been proposed, and because of their small molecular polarizability, the resulting coating films have low dielectric constants and excellent heat resistance. Examples of such borazine compounds include N-alkylborazines, in which the nitrogen atom constituting the borazine ring is bonded to an alkyl group, and these compounds are preferably used to form semiconductor interlayer insulating films, barrier metal layers, and etch stopper layers.

[0005] For example, Patent Document 1 describes a method for producing N-alkylborazine, ４ (A is a lithium atom, a sodium atom, or a potassium atom), and an alkali borohydride represented by RNH ３ The following are disclosed: a method for producing N-alkylborazine, which includes the steps of charging a reaction vessel with one of the alkylamine salts represented by X (R is an alkyl group, and X is a halogen atom) and gradually supplying the other to the reaction vessel and reacting them in a solvent; and a method for producing N-alkylborazine, which involves gradually supplying the alkali borohydride and the alkylamine salt to the reaction vessel and reacting them in a solvent.

[0006] Japanese Patent Application Laid-Open No. 2006-213683

[0007] According to the production method disclosed in Patent Document 1, the amount of hydrogen gas generated in the reaction of an alkali borohydride with an alkylamine salt can be controlled. However, further investigation by the present inventors revealed that it may be difficult to efficiently obtain the resulting N-alkylborazine compound in high yield using a method in which an alkali borohydride with an alkylamine salt is reacted in an organic solvent.

[0008] Therefore, an object of the present invention is to provide a production method that can produce an N-alkylborazine compound in high yield.

[0009] The present invention, which has achieved the above object, is as follows: [1] ABH ４ (A is a lithium atom, a sodium atom, or a potassium atom) and an alkali borohydride represented by RNH ３ A method for producing an N-alkylborazine compound by reacting an alkylamine salt represented by X (R is an alkyl group, and X is a halogen atom) in an organic solvent, the method comprising: ３ [2] A method for producing an N-alkylborazine compound, comprising reacting the alkali borohydride and the alkylamine salt while applying a stirring power of 0.1 to 10 kW per unit time. [2] The method according to [1], wherein the yield of N-alkylcycloborazane is 1.0% or less. [3] The method according to [1] or [2], wherein the ratio of the yield of N-alkylcycloborazane to the yield (%) of N-alkylborazine is 0.010 or less. [4] The method according to any one of [1] to [3], wherein the alkali borohydride and the alkylamine salt are reacted at 100 to 200°C. [5] The method according to [4], wherein the alkali borohydride and the alkylamine salt are reacted at a temperature T1 of 150°C or higher but lower than 200°C, and then reacted at a temperature T2 of higher than 150°C but lower than 200°C, and the stirring power is applied at least while the temperature is at T2. [6] The alkali borohydride is sodium borohydride (NaBH ４[7] The alkylamine salt is monomethylamine hydrochloride (CH ３ NH ３ [8] The method according to any one of [1] to [7], wherein the organic solvent is one or more selected from the group consisting of monoglyme, diglyme, triglyme, and tetraglyme. [9] The method according to any one of [1] to [8], wherein the alkali borohydride and the alkylamine salt are reacted in a reaction vessel having a volume of 0.5 to 10,000 L.

[10] The method according to any one of [1] to [9], wherein the reaction solution is stirred using at least one stirring blade selected from the group consisting of a propeller type, a paddle type, a turbine type, a cone type, a ribbon screw type, and a Maxblend type.

[0010] According to the present invention, an N-alkylborazine compound can be obtained in high yield, and preferably, the amount of the borazane compound, which is a reaction intermediate, in the final product can also be reduced.

[0011] The present invention is ４ (A is a lithium atom, a sodium atom, or a potassium atom) and an alkali borohydride represented by RNH ３ A method for producing an N-alkylborazine compound by reacting an alkylamine salt represented by X (R is an alkyl group and X is a halogen atom) in an organic solvent, the method comprising: ３The method is characterized in that the alkali borohydride and the alkylamine salt are reacted while applying a stirring power of 0.1 to 10 kW per unit volume. By applying the stirring power described above to drive the reaction, an N-alkylborazine compound can be obtained in high yield, and preferably, the amount of borazane compound, a reaction intermediate, in the final product can be reduced. To obtain an N-alkylborazine compound, further purification such as distillation can be performed after employing the production method of the present invention. However, obtaining an N-alkylborazine compound in high yield is also preferable in that it improves purification efficiency and allows for the production of a high-purity N-alkylborazine compound suitable as a film-forming material for semiconductors. Furthermore, because of their similar molecular structures, it is possible to reduce the amount of borazane compound, a reaction intermediate that requires time and effort to separate from the N-alkylborazine compound, which is also preferable in that it improves purification efficiency.

[0012] The stirring power is determined based on the final volume of the solution of the alkali borohydride, alkylamine salt, and organic solvent. ３ This means a value converted to per unit mass. Preferably, in the production method of the present invention, a stirring power in the above-mentioned range is applied at least after the entire amount of the alkali borohydride and the entire amount of the alkylamine salt have been charged into a reaction vessel, and more preferably, a stirring power in the above-mentioned range is applied from the start of the reaction of the alkali borohydride and the alkylamine salt to the end of the reaction. The start of the reaction may be the time when the alkali borohydride and the alkylamine salt have been mixed even partially, and the end of the reaction may be the time when cooling begins when the reaction solution containing the alkali borohydride and the alkylamine salt is heated and then cooled.

[0013] The stirring power is preferably 0.2 kW / m ３ More preferably, it is 0.3 kW / m or more. ３ and above 8kW / m ３ It may be less than 5 kW / m ３ That is, the stirring power may be 0.2 to 8 kW / m ３ is preferred, and 0.3 to 5 kW / m ３The time for applying the stirring power in the above range is preferably 1 hour or more, more preferably 2 hours or more, and even more preferably 4 hours or more, and the upper limit may be 72 hours. In other words, the time for applying the stirring power in the above range is preferably 1 to 72 hours, more preferably 2 to 72 hours, and even more preferably 4 to 72 hours.

[0014] In the present invention, it is preferable to satisfy any one of the following requirements: (i) a step of first charging an alkali borohydride into a reaction vessel, and a step of gradually feeding an alkylamine salt to the reaction vessel containing the alkali borohydride to react the alkali borohydride and the alkylamine salt in a solvent; (ii) a step of first charging an alkylamine salt into a reaction vessel, and a step of gradually feeding the alkali borohydride to the reaction vessel containing the alkylamine salt to react the alkali borohydride and the alkylamine salt in a solvent; or (iii) a step of gradually feeding both the alkali borohydride and the alkylamine salt to the reaction vessel. By satisfying any of these requirements, it is possible to prevent the reaction from generating a large amount of hydrogen gas in a short period of time. Of these, mode (ii) is preferred.

[0015] In both cases (i) and (ii) above, it is preferable to premix both the alkali borohydride and the alkylamine salt with an organic solvent. Also in case (iii), a mixture of the alkali borohydride and the alkylamine salt with an organic solvent may be prepared, and both may be gradually fed simultaneously to the reaction vessel. Alternatively, one of the alkali borohydride and the alkylamine salt may be mixed with an organic solvent, while the other is prepared as a solid, and both may be gradually fed simultaneously to the reaction vessel. Note that the term "gradually fed" as used above means that the entire amount is not fed all at once, but is fed in portions intermittently or continuously. The feed time can be determined depending on the reaction scale and the compounds used; for example, it can be fed over a period of 0.5 to 48 hours. If the feed amount can be determined empirically or experimentally, it is preferable to control the feed to a predetermined amount. The feed rate of the gradually fed alkali borohydride or alkylamine salt is, for example, 8 to 20 g / (L-hour) per unit volume (L) of the reaction vessel and per unit time. The supply of the solvent may be automatic or manual. For example, when production is carried out at a laboratory level, the amount of precipitation may be visually confirmed and the solvent may be supplied as needed.

[0016] The alkali borohydride and the alkylamine salt are preferably reacted under an inert gas atmosphere. Examples of the inert gas include nitrogen gas and rare gases such as helium gas, neon gas, argon gas, krypton gas, and xenon gas. Nitrogen gas or argon gas is preferred, and nitrogen gas is particularly preferred.

[0017] The temperature at which the alkali borohydride and the alkylamine salt are reacted, i.e., the temperature of the reaction solution as the reaction proceeds (from the start of the reaction to the end of the reaction), is preferably 100 to 200°C, more preferably 150 to 200°C, and it is even more preferable to apply stirring power within the above-mentioned range while the reaction solution is at this temperature. While the reaction proceeds, the temperature may be constant or variable within the preferred temperature range of 150 to 200°C. It is also preferable to set the temperature at T1 (where 150°C ≦ T1 < 200°C) and then raise the temperature to T2 (where 150°C < T2 ≦ 200°C), which is higher than T1. It is presumed that when the alkali borohydride and the alkylamine salt are reacted, an intermediate N-alkylcycloborazane is first produced, and then hydrogen is released from the N-alkylcycloborazane to produce N-alkylborazine. The reaction to produce N-alkylborazine from this intermediate is thought to proceed at relatively high temperatures. For example, at the beginning of the reaction, it is preferable to control the reaction solution to a low temperature of T1 to produce N-alkylcycloborazane, and then raise the temperature of the reaction solution to T2 once most of the raw material has become N-alkylcycloborazane, thereby completing the synthesis of N-alkylborazine. The reaction time is, for example, a total of 3 to 72 hours. When the temperature of the reaction solution is changed from T1 to T2, it is preferable to carry out the reaction at T1 for 2 to 48 hours and at T2 for 1 to 24 hours. In the above-mentioned embodiment (i), the temperature during the supply of the alkylamine salt is set to T1, and in the embodiment (ii), the temperature during the supply of the alkali borohydride is set to T1. In either case, it is preferable to set the temperature to T2 after the supply is completed. In these cases, it is preferable to apply the above-mentioned stirring power at least while the temperature is at T2, and it is more preferable to apply the above-mentioned stirring power at both temperatures T1 and T2. It is preferable that the stirring power applied while the temperature is at T2 is 0.2 kW / m ３ or more than 0.3kW / m ３ After the reaction is complete, the mixture may be allowed to cool to room temperature (about 10 to 35° C.) by, for example, allowing it to stand. The reaction temperature can be measured using a temperature sensor such as a K thermocouple.

[0018] Alkali borohydrides (ABH４ In the formula (I), A is a lithium atom, a sodium atom, or a potassium atom. A preferred example of an alkali borohydride is sodium borohydride (NaBH ４ ) and lithium borohydride (LiBH ４ ) is mentioned, and sodium borohydride is more preferred.

[0019] Alkylamine salts (RNH ３ In the formula (X), R is an alkyl group and X is a halogen atom. The alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 4. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 1-methylbutyl group, a 2-methylbutyl group, a pentyl group, an isopentyl group, a neopentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group, with a methyl group or an ethyl group being preferred. An alkyl group other than these may also be used. X is preferably a fluorine atom, a chlorine atom, or a bromine atom, and more preferably a chlorine atom. Examples of alkylamine salts include monomethylamine hydrochloride (CH ３ NH ３ Cl), monoethylamine hydrochloride (CH ３ CH ２ NH ３ Cl), monomethylamine hydrobromide (CH ３ NH ３ Br), monoethylamine hydrofluoride (CH ３ CH ２ NH ３ F) The alkylamine salt is preferably monomethylamine hydrochloride.

[0020] The N-alkylborazine compound obtained by the present invention is a compound represented by the following formula (I).

[0021]

[0022] In formula (I), R １ ~R ３ is the same as R in the alkylamine salt, and R １ ~R ３ may be the same as or different from each other. Examples of N-alkylborazine include N,N',N''-trimethylborazine, N,N',N''-triethylborazine, N,N',N''-tri(n-propyl)borazine, N,N',N''-tri(isopropyl)borazine, N,N',N''-tri(n-butyl)borazine, N,N',N''-tri(sec-butyl)borazine, N,N',N''-tri(isobutyl)borazine, N,N',N''-tri(tert-butyl)borazine, and N,N',N''-tri(1-methylbutyl)borazine. Examples thereof include N,N',N''-tri(2-methylbutyl)borazine, N,N',N''-tri(neo-pentyl)borazine, N,N',N''-tri(1,2-dimethylpropyl)borazine, N,N',N''-tri(1-ethylpropyl)borazine, N,N',N''-tri(n-hexyl)borazine, N,N',N''-tricyclohexylborazine, N,N'-dimethyl-N''-ethylborazine, N,N'-diethyl-N''-methylborazine, and N,N'-dimethyl-N''-propylborazine. The borazine compound is preferably one or more of N,N',N''-trimethylborazine, N,N',N''-triethylborazine, N,N'-dimethyl-N''-ethylborazine, and N,N'-diethyl-N''-methylborazine, and more preferably N,N',N''-trimethylborazine.

[0023] The alkali borohydride and alkylamine salt to be used may be selected depending on the structure of the N-alkylborazine to be synthesized. For example, when producing N-methylborazine in which a methyl group is bonded to the nitrogen atom constituting the borazine ring, an alkylamine salt in which R is a methyl group, such as monomethylamine hydrochloride, may be used as the alkylamine salt.

[0024] The organic solvent is preferably one or more ether solvents, such as diethyl ether, tetrahydrofuran, monoethylene glycol dimethyl ether (monoglyme), diethylene glycol dimethyl ether (diglyme), triethylene glycol dimethyl ether (triglyme), and tetraethylene glycol dimethyl ether (tetraglyme). The organic solvent is more preferably one or more selected from the group consisting of monoglyme, diglyme, triglyme, and tetraglyme, even more preferably one or more of triglyme and tetraglyme, and even more preferably triglyme.

[0025] The ratio of the amount of the alkali borohydride to the amount of the alkylamine salt used is not particularly limited, but it is preferable that the amount of the alkali borohydride used is 0.8 to 1.2 moles when the amount of the alkylamine salt used is 1 mole.

[0026] The total amount of the alkali borohydride and alkylamine salt relative to the total amount of the alkali borohydride, alkylamine salt, and solvent used in the reaction is preferably 10 to 30% by mass, more preferably 15 to 25% by mass. Furthermore, in the above cases (i) and (ii), when the alkali borohydride and alkylamine salt are mixed with an organic solvent, the amount of the alkali borohydride relative to 100 parts by mass of the organic solvent is preferably 10 to 40 parts by mass, more preferably 15 to 35 parts by mass, and the amount of the alkylamine salt relative to 100 parts by mass of the organic solvent is preferably 20 to 50 parts by mass, more preferably 25 to 40 parts by mass.

[0027] The volume of the reaction vessel is preferably 0.5 to 10,000 L, and may be 0.5 to 5,000 L, 0.5 to 1,000 L, 0.5 to 500 L, or 0.5 to 100 L, and may be appropriately set depending on the target production amount.

[0028] The stirring blades for adjusting the stirring power within the above range are preferably at least one type selected from the group consisting of propeller type, paddle type, turbine type, cone type, ribbon screw type, and Maxblend type, and are particularly preferably paddle type, and preferably satisfy at least one of the requirements of having 2 to 6 paddle blades and being an inclined paddle type. It is also preferable to use at least one type selected from the group consisting of propeller type, paddle type, turbine type, cone type, ribbon screw type, and Maxblend type in combination with an anchor type, and in this case, it is preferable to install the anchor type below with respect to the direction of the rotation axis. It is particularly preferable to use an inclined paddle type blade with 2 to 6 blades in combination with an anchor type blade, with the anchor type below with respect to the direction of the rotation axis.

[0029] The yield of N-alkylborazine obtained by the production method of the present invention is preferably 80.0% or more, more preferably 85% or more, and even more preferably 88% or more, with the upper limit being most preferably 100% but may be around 95%. That is, the yield of N-alkylborazine is preferably 80.0 to 100%, more preferably 85 to 95%, and even more preferably 88 to 95%.

[0030] In the production method of the present invention in which an N-alkylborazine compound is produced by reacting an alkali borohydride with an alkylamine salt, an N-alkylcycloborazane of the following formula (II) can be produced as an intermediate.

[0031] In formula (II), R １ ~R ３ is R in formula (I) １ ~R ３ is synonymous with.

[0032] However, in the present invention, in which a predetermined range of stirring power is applied to the reaction solution, the amount of intermediates in the final product is reduced, and the yield of N-alkylcycloborazane can be reduced to 1.0% or less, preferably 0.9% or less, and more preferably 0.8% or less, with the lower limit being most preferably 0% but also approximately 0.1%. That is, the yield of N-alkylcycloborazane is preferably 0 to 1.0%, more preferably 0.1 to 0.9%, and even more preferably 0.1 to 0.8%.

[0033] Furthermore, the ratio of the yield (%) of N-alkylcycloborazane to the yield (%) of N-alkylborazine is preferably 0.010 or less, more preferably 0.009 or less, and even more preferably 0.008 or less, and the lower limit may be, for example, about 0.001. That is, the ratio of the yield (%) of N-alkylcycloborazane to the yield (%) of N-alkylborazine is preferably 0.001 to 0.010, more preferably 0.001 to 0.009, and even more preferably 0.001 to 0.008.

[0034] The N-alkylborazine compound obtained by the present invention can be used in the formation of an interlayer insulating film for semiconductors, a barrier metal layer, an etch stopper layer, etc., either as the N-alkylborazine compound itself or as a polymer obtained by polymerizing an N-alkylborazine or an N-alkylborazine derivative.

[0035] This application claims the benefit of priority based on Japanese Patent Application No. 2023-140438, filed on August 30, 2023. The entire contents of the specification of Japanese Patent Application No. 2023-140438, filed on August 30, 2023, are incorporated herein by reference.

[0036] The present invention will be described in more detail below with reference to examples. The present invention is not limited to the following examples, and can of course be practiced with appropriate modifications within the scope of the above and below-described aims, all of which are included in the technical scope of the present invention.

[0037] Example 1 A 0.5 L reaction vessel equipped with a cooling tube and four anchor-type impellers and four 45° paddle-type impellers as stirring blades (with the anchor-type impellers positioned downward relative to the direction of the rotation axis) was charged with 42 g of methylamine hydrochloride as an alkylamine salt and 123 g of triglyme as a solvent while purging with nitrogen, and the liquid temperature was raised to 150°C with stirring.

[0038] Next, the liquid temperature was kept at 150°C, and the stirring power per unit volume given to the charge liquid (the liquid consisting of 42 g of methylamine hydrochloride and 123 g of triglyme) was 0.73 kW / m ３ A slurry liquid consisting of 26 g of sodium borohydride as an alkali borohydride and 111 g of triglyme as a solvent was gradually fed into the reaction vessel over 4 hours while stirring to obtain a reaction temperature of 100°C. The change in the amount of gas discharged from the reaction vessel revealed that hydrogen gas was steadily generated during the reaction.

[0039] After the slurry liquid was supplied, the temperature of the reaction liquid (containing 42 g of the above-mentioned methylamine hydrochloride, 123 g of triglyme, 26 g of sodium borohydride, and 111 g of triglyme) was raised to 170°C, and the stirring power per unit volume given to the reaction liquid was 0.40 kW / m ３ The reaction mixture was stirred for 2 hours to mature the reaction.

[0040] After completion of the reaction, the reaction solution was allowed to cool to 25°C, and then analyzed by gas chromatography (GC). The reaction yield of N,N',N''-trimethylborazine and the reaction yield of the reaction intermediate N,N',N''-trimethylcycloborazane were measured by the methods described below.

[0041] Example 2 A 1 L reaction vessel equipped with a cooling tube and four anchor-type impellers and four 45° paddle-type impellers as stirring blades (with the anchor-type impellers positioned downward relative to the direction of the rotation axis) was charged with 84 g of methylamine hydrochloride as an alkylamine salt and 246 g of triglyme as a solvent while purging with nitrogen, and the liquid temperature was raised to 150°C with stirring.

[0042] Next, the temperature was maintained at 150°C, and the stirring power per unit volume given to the charged liquid (the liquid consisting of 84 g of methylamine hydrochloride and 246 g of triglyme) was 0.73 kW / m ３ A slurry liquid consisting of 52 g of sodium borohydride as an alkali metal borohydride and 222 g of triglyme as a solvent was gradually fed into the reaction vessel over 4 hours while stirring to obtain a reaction temperature of 100°C. The change in the amount of gas discharged from the reaction vessel revealed that hydrogen gas was steadily generated during the reaction.

[0043] After the slurry liquid was supplied, the temperature of the reaction liquid (containing 84 g of the above-mentioned methylamine hydrochloride, 246 g of triglyme, 52 g of sodium borohydride, and 222 g of triglyme) was raised to 170°C, and the stirring power per unit volume given to the reaction liquid was 0.40 kW / m ３ The reaction mixture was stirred for 2 hours to mature the reaction.

[0044] After completion of the reaction, the reaction solution was allowed to cool to 25°C and then analyzed by gas chromatography (GC). The reaction yield of N,N',N''-trimethylborazine and the reaction yield of the reaction intermediate N,N',N''-trimethylcycloborazane were measured by the methods described below.

[0045] Comparative Example 1 A 0.5 L reaction vessel equipped with a condenser and a half-moon impeller as a stirring blade was charged with 42 g of methylamine hydrochloride as an alkylamine salt and 123 g of triglyme as a solvent while purging with nitrogen, and the liquid temperature was raised to 150°C with stirring.

[0046] Next, while maintaining the temperature at 150°C, the stirring power per unit volume applied to the charged liquid (the liquid consisting of 42 g of methylamine hydrochloride and 123 g of triglyme) was 0.09 kW / m ３ While stirring to obtain the above, a slurry liquid consisting of 26 g of sodium borohydride as an alkali borohydride and 111 g of triglyme as a solvent was gradually fed into the reaction vessel over a period of 4 hours to carry out the reaction.

[0047] After the slurry liquid was supplied, the temperature of the reaction liquid (containing 42 g of the above-mentioned methylamine hydrochloride, 123 g of triglyme, 26 g of sodium borohydride, and 111 g of triglyme) was raised to 170°C, and the stirring power per unit volume given to the reaction liquid was 0.05 kW / m ３ The reaction was aged for 2 hours by stirring until the temperature reached 0.5°C.

[0048] After completion of the reaction, the reaction solution was allowed to cool to 25°C and then analyzed by gas chromatography (GC). The reaction yield of N,N',N''-trimethylborazine and the reaction yield of the reaction intermediate N,N',N''-trimethylcycloborazane were measured by the methods described below.

[0049] In the examples and comparative examples, the reaction solution was analyzed by gas chromatography under the following conditions, and the yields of N,N',N''-trimethylborazine and N,N',N''-trimethylcycloborazane were calculated based on the amount of methylamine hydrochloride charged. Apparatus: GC-2014 manufactured by Shimadzu Corporation Column: Ultra Alloy-1 manufactured by Frontier Labs Carrier gas: Nitrogen Carrier gas flow rate: 3.0 mL / min Sample injection temperature: 200°C Detector temperature: 280°C Sample injection amount: 0.2 μL Column temperature: 50°C (4 min), heated to 280°C at a heating rate of 20°C / min, and then 280°C (15 min)

[0050] The results are shown in Table 1.

[0051]

[0052] From the above, in the method for producing an N-alkylborazine compound, the stirring power per unit volume given to the reaction solution is set to 0.1 to 10 kW / m ３ It was found that by stirring while maintaining the temperature at 200°C, an N-alkylborazine compound can be obtained in high yield. In addition, it was found that the amount of N-alkylcycloborazane, a reaction intermediate, can be reduced, making it easy to obtain a high-purity N-alkylborazine compound.

Claims

1. A.B.H. ４ (A is a lithium atom, a sodium atom, or a potassium atom) and an alkali borohydride represented by RNH ３ A method for producing an N-alkylborazine compound by reacting an alkylamine salt represented by X (R is an alkyl group and X is a halogen atom) in an organic solvent, the method comprising the steps of: ３ The method for producing an N-alkylborazine compound comprises reacting the alkali borohydride with the alkylamine salt while applying a stirring power of 0.1 to 10 kW per minute.

2. The method according to claim 1, wherein the alkali borohydride and the alkylamine salt are reacted at 100 to 200°C.

3. The method of claim 2, wherein the alkali borohydride and the alkylamine salt are reacted at a temperature T1 of 150°C or higher but lower than 200°C, and then at a temperature T2 of more than 150°C but lower than 200°C, and the stirring power is applied at least while the reaction mixture is at the temperature T2.

4. The alkali borohydride is sodium borohydride (NaBH ４ 3. The method according to claim 1 or 2, wherein 5. The alkylamine salt is monomethylamine hydrochloride (CH ３ N.H. ３ 3. The method according to claim 1 or 2, wherein the compound is selected from the group consisting of fluorine, fluorine 6. The method according to claim 1 or 2, wherein the organic solvent is at least one selected from the group consisting of monoglyme, diglyme, triglyme, and tetraglyme.

7. The method according to claim 1 or 2, wherein the alkali borohydride and the alkylamine salt are reacted in a reaction vessel having a volume of 0.5 to 10,000 L.

8. The method according to claim 1 or 2, wherein the reaction solution is stirred using at least one type of stirring blade selected from the group consisting of a propeller type, a paddle type, a turbine type, a cone type, a ribbon screw type, and a Max Blend type.

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