WO2008102661A1 - Method for producing trialkylsilylnitrile - Google Patents

Abstract

Disclosed is a method for easily and safely producing high-quality trimethylsilylnitrile, which is useful as a nitrilation agent or the like, with high yield. Specifically disclosed is a method for producing a trialkylsilylnitrile represented by the general formula (3) below, which is characterized in that a trialkylsilylhalide represented by the general formula (1) below is reacted with an inorganic salt of hydrogen cyanide represented by the general formula (2) below in the presence of a catalyst in a non-solvent system or in an organic solvent system. (In the formula (1), R1, R2 and R3 may be the same or different and represent an alkyl group, and A represents a halogen atom.). (In the formula M(CN)n (2), M represents an alkali metal or an alkaline earth metal, and n is 1 or 2.) (In the formula (3), R1, R2 and R3 are as defined above.)

Description

 Method for producing trialkylsilyl nitrile Technical Field

 The present invention relates to a novel process for producing trialkylsilyl nitrile. Light

 Background art

 Rice field

 Conventionally, for example, the following methods (1) to (4) are known as methods for producing trimethylsilylnitrile.

 (1) A method in which trimethylsilyl chloride and an inorganic salt of hydrogen cyanide are reacted in a solvent such as dichloromethane, acetonitrile, or N-methylpyrrolidone (see Non-Patent Documents 1, 2, and 3).

 (2) A method of reacting perchloric acid trimethylsilyl ester with sodium cyanide (see Non-Patent Document 4).

 (3) A method of reacting trimethylsilyl bromide with bis (triphenylphosphine) iminum cyanide (see Non-Patent Document 5).

 (4) A method of reacting a cyanidation power rhium with bistrimethylsilanyl sulfate (see Non-Patent Document 6).

 However, in the above production method (1), when the produced trimethylsilylnitrile is purified by distillation, it cannot be sufficiently separated from the solvent. That is, in order to obtain high-purity trimethylsilylnitrile, a multi-stage precision distillation apparatus is necessary, and equipment for that purpose is required, leading to an increase in production cost.

 In addition, since the above production methods (2) to (4) use reaction reagents that are not commercially available, they are necessary for their preparation and require a long process.

 Therefore, the conventional method for producing trialkylsilyl nitrile has the problems described above, and is not necessarily an industrially optimal method.

Non-patent literature l: S ynt h. C o mm u n., 3 5 (9), 1 27 1 (2005) = Synthetic Communications, 3rd 5th (9) edition, pl 27 1, 2000 5 years

 Non-Patent Document 2: S yn ht e s, 2 1 2 (1 982) = synthesis,

2, 1 9 8 2 years

 Non-Patent Document 3: T e ra a h e d r o n, 5 2 (3 7), 1 2 06 (1 9

= Tetrahedron, 52nd (3 7) edition, ρ 1 20 6, 1 9 96

 Non-Patent Document 4: J. Chem. Soc · Chem. Commm., 45

9 88) = Journal • Op. Chemical • Society 'Chemicals'

—Shillons, p 45 5, 1 9 88

 Non-Patent Document 5: Synth. Comm n., 84 9 (1 9 8 5) = Synthetic 'Communications, ρ 84 9, 1 9 8 5

 Non-Patent Document 6: Syn ht e s, 2 7 7 (1 9 8 2) = Synthesis, p 27 7, 1 9 8 2

 Problems to be solved by the invention

 An object of the present invention is to provide a method for easily and safely producing a trialkylsilyl nitrinole useful as a tolylating agent and the like in a high yield and a high quality.

 Means for solving the problem

 The present invention provides a method for producing trialkylsilyl nitrile as shown below.

 Item 1. — General formula (1);

[Chemical 1]

(Wherein R 1, R 2 and R 3 are the same or different and each represents an alkyl group, and A represents a halogen atom) and a general formula (2) ; [Chemical 2]

M (CN) _n (2)

(Wherein M is an alkali metal or alkaline earth metal, and n is 1 or 2), and is reacted in a non-solvent system in the presence of a catalyst with an inorganic salt of hydrogen cyanide represented by General formula (3);

[Chemical 3]

(Wherein R 1, R 2 and R 3 have the same meanings as described above).

 Item 2. The method for producing trialkylsilyl nitrile according to Item 1, wherein the trialkylsilyl halide is trimethylsilyl halide.

 Item 3. The method for producing a trialkylsilyl nitrile according to Item 2, wherein the trimethylsilyl halide is trimethylsilyl chloride.

 Item 4. The method for producing trialkylsilylnitrile according to Item 1, wherein the inorganic salt of hydrogen cyanide is sodium cyanide or potassium cyanide.

 Item 5. The method for producing trialkylsilyl nitrile according to Item 1, wherein the catalyst is a compound selected from the group consisting of iodine, zinc iodide, trimethylsilyl nitrile and a mixture thereof. .

 Item 6. General formula (1);

 [Chemical 4]

R ³

(Wherein Rl, R2, and R3 are the same or different and each represents an alkyl group, and A represents a halogen atom), and a general formula (2); [Chemical 5]

M (CN) _n (2)

(In the formula, M is an alkali metal or alkaline earth metal, and n is 1 or 2.) In the presence of a catalyst, an organic solvent system is reacted with an inorganic salt of hydrogen cyanide represented by General formula characterized by (3);

[Chemical 6]

(Wherein R 1, R 2 and R 3 are as defined above).

Item 7. The method for producing a trialkylsilyl nitrile according to Item 6, wherein the trialkylsilyl halide is trimethylsilyl halide.

Item 8. The method for producing a trialkylsilyl nitrile according to Item 6, wherein the trimethylsilyl halide is trimethylsilyl chloride.

Item 9. The method for producing trialkylsilylnitrile according to Item 6, wherein the inorganic salt of hydrogen cyanide is sodium cyanide or potassium cyanide.

Item 10. The method for producing a trialkylsilanolonitrile according to Item 6, wherein the catalyst is a compound selected from the group consisting of iodine, zinc iodide, trimethylsilylnitrile, and a mixture thereof.

Item 11. The method for producing trialkylsilylnitrile according to Item 6, wherein the organic solvent is silicone oil or liquid paraffin.

Item 12. The trialkylsilyl dito compound according to Item 6, wherein the organic solvent is decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane or eicosane. A method for producing rills.

Item 13. React in a non-solvent system in the presence of a catalyst, then add an organic solvent and distill Item 7. The method for producing a trialkylsilyl nitrile according to Item 6, wherein

Item 14. The method for producing a trialkylsilyl-tolyl according to Item 13, wherein an organic solvent is added according to the amount of the distillate of the trialkylsilyl nitrile during distillation.

 The invention's effect

 According to the present invention, it is a very advantageous method for easily producing high-purity trialkylsilyl nitrinole as compared with the conventional method required for precision distillation and the method using a reagent that is not easily available. It is. In addition, since no reaction solvent is used, it is a great advantage that the environmental impact is greatly reduced.

 BEST MODE FOR CARRYING OUT THE INVENTION

 The present invention is described in detail below.

 First, R 1, R 2, R 3, A, M, and n in the general formulas (1), (2), and (3) will be described.

 R 1, R 2 and R 3 are the same or different alkyl groups, but may be linear or branched. In the case of a branched chain, the branch position and the number of branches are not particularly limited, and those having 1 to 10 carbon atoms are preferable, and those having 1 to 4 carbon atoms are more preferable. Preferred examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopino pinole group, an n-butyl group, a but-2-yl group, and a 2-methylprop-1-yl group. 2-methylprop-2-yl group and the like. A methyl group and an ethyl group are preferable, and a methyl group is particularly preferable.

 A is a halogen atom, but there is no particular limitation. Specific examples include fluorine, chlorine, bromine, iodine and the like, and chlorine is particularly preferred from the standpoint of availability.

M is an Al-strength metal or Al-strength earth metal, but there is no particular limitation. Specific examples include alkali metals such as lithium, sodium, potassium, rubidium, and cesium, and alkaline earth metals such as beryllium, magnesium, calcium, strontium, and sodium, and potassium and sodium are particularly preferable. n is 1 when M is an alkali metal, and 2 when M is an alkaline earth metal. The amount of the hydrogen cyanide inorganic salt used is preferably 1.0 mol to 3.0 mol with respect to 1 mol of trialkylsilyl halide represented by the general formula (1). 1.0 mol to 2.0 mol is preferred.

 The catalyst used in the reaction is preferably iodine, sodium iodide, potassium iodide, zinc chloride, zinc bromide, zinc iodide, zinc oxide, copper iodide, manganese iodide, trimethylsilylnitrile, iodine, iodide. Zinc and trimethylsilylnitrile are particularly preferred. These may be used alone or in combination. The amount of the catalyst used is preferably from 0.001 mol to 0.5 mol based on 1 mol of the trialkylsilyl halide represented by the general formula (1). 3 moles is more preferred.

 The reaction is performed by mixing a trialkylsilyl halide represented by the general formula (1), a catalyst, and an inorganic salt of hydrogen cyanide.

 If the reaction temperature is too high, by-products are increased, and if it is too low, the reaction rate is low. Therefore, the reaction temperature is preferably about 0 ° C to 60 ° C, more preferably about 10 ° C to 50 ° C. . The reaction time is usually about 1 hour to 200 hours, preferably about 3 hours to 100 hours, depending on the type of catalyst and the amount added.

 After completion of the reaction, high-purity trialkylsilylnitrile represented by the above general formula (3) can be obtained by simple distillation (no need for a multistage precision distillation apparatus) or only filtration of inorganic salts.

 Examples of the organic solvent used in the present invention include liquid paraffin, silicone, silicone oil, hexane, heptane, octane, nonane, decane, decalin, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, Examples include, but are not limited to, octadecane, nonadecane, and eicosane. Silicone oil, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, and octadecane are preferred industrially.

When used as a reaction solvent, the organic solvent is preferably used in an amount of usually 0.5 g to 50 g with respect to 1 g of trimethylsilyl halide represented by the general formula (1). 5 g to 20 g is more preferable. In addition, when added and used during distillation, 0.5 to 3 ml is usually preferable to 1 g of trimethylsilyl halide. More preferably, 1 m 1 to 2 m 1 is more preferable.

 After the reaction, high-purity trimethylsilylnitrile can be isolated by distillation. When the reaction is carried out in a non-solvent system, the by-product salt is difficult to disperse at the end of the distillation and the stirrability is lowered.

 Depending on the amount of trimethylsilylnitrile distilled, trimethylsilylnitrile can be isolated without reducing the volume fraction by adding an organic solvent. Furthermore, since the organic solvent used has a high boiling point, it does not distill with trimethylsilylnitrile, so that high-purity trimethylsilylnitrile can be obtained only by simple distillation without the need for a multistage precision distillation apparatus. .

 Example

 The present invention will be described more specifically with reference to the following examples. However, the present invention is not limited to these examples.

Example 1 Preparation of trimethylsilyl nitrile in a non-solvent system

 Trimethino resilino lectin lid (30 g, 276 mm o 1), sodium cyanide (14.9 g, 304 mm o 1), iodine (1.5 g, 5.9 mm o 1) in a 100 ml flask In addition, the reaction was carried out at 20 ° C to 30 ° C for 13 hours. After completion of the reaction, simple distillation yielded 22.3 g (yield 81.4%) of trimethylsilylnitrile as a colorless liquid. The content was 95.9% (GC area percentage).

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

 1H NMR (400MHz, CDC):? 0.35 (s, 9H).

Example 2 Preparation of triethylsilylnitrile in a non-solvent system

 To a 50 ml flask, add triethylsilinolec mouthlid (10 g, 66 mm o 1), sodium cyanide (3.6 g, 73 mmo 1), iodine (0.5 g, 3.9 mmo 1) 20 The reaction was carried out at 15-30 ° C for 15 hours. After completion of the reaction, simple distillation gave triethylsilylnitrile as a colorless liquid in 6.8 g (yield 73.2%). The content was 93.6% (GC area percentage).

1H Awakening R (400MHz, CDC13): δ 1.00 (q, J = 7.2 Hz, 6H), 0.78 (t, J = 7.2 Hz, 9H).

Example 3 Production of trimethylsilyl nitrile in a non-solvent system

 To a 100 ml flask, add trimethylsilyl chloride (30 g, 276 mm o 1 power cyanide (21.8 g, 304 mmo 1), iodine (1.5 g, 5.9 mmo 1) The reaction was carried out for 16 hours at 30 ° C. After completion of the reaction, tridiylsilylnitrile was obtained as a colorless liquid in 24.1 g (yield 88.0%) by simple distillation. GC area percentage) IR (KCl, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

Example 4 Preparation of trimethylsilyl nitrile in a non-solvent system

 100 ml flask with trimethinoresinolec lide (30 g, 276 mm o 1), sodium cyanide (14.9 g, 304 mm o 1), zinc iodide (8.8 g, 27.6) mm o 1) was added and the reaction was carried out at 20 ° C to 30 ° C for 39 hours. After completion of the reaction, simple distillation gave trimethylsilylnitrile as a colorless liquid in 19.5 g (yield 71.2%). The content was 93.1% (GC area percentage).

 IR (KCl, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

 1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

Example 5 Preparation of triethylsilylnitrile in a non-solvent system

 Triethino resilino lectin lid (10 g, 66 mmo 1), sodium cyanide (3.6 g, 73 mm o 1), zinc oxalate (2.1 g, 6.6 mmo 1) in a 50 ml flask And reacted at 20 ° C to 30 ° C for 28 hours. After completion of the reaction, simple distillation yielded 6.3 g (yield: 6.6.9%) of triethylsilyl-tolyl as a colorless liquid. The content was 94.7% (GC area percentage).

 1H hire R (400MHz, CDC13): δ 1.00 (q, J = 7.2 Hz, 6H), 0.78 (t, J = 7.2 Hz,

9H).

Example 6 Production of trimethylsilinolenitrile in a non-solvent system

In a 100 ml flask, trimethylsilyl chloride (30 g, 276 mm o 1), Sodium cyanide (15.0 g, 30 4 mm ol), zinc oxalate (8.8 g, 27.6 mm o 1), trimethylsilylnitrinole (1.5 g, 15.1 mm o 1) was added and reacted at 20 ° C. to 30 ° C. for 15 hours. After completion of the reaction, trimethylsilylnitrile was obtained as a colorless liquid in 16.9 g (yield 61.7%) by simple distillation. The content was 92.4% (GC area percentage).

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

 1H NMR (400MHz, CDC):? 0.35 (s, 9H).

 Example 7 Production of trimethylsilyl nitrile in a non-solvent system

 Trimethylsilyl chloride (30 g, 2 76 mm o 1), sodium cyanide (1 4.9 g, 30 4 mmo 1), sodium iodide (4 lg, 2 7. 6 mmo 1) Add 20 ° C ~ 30. The mixture was reacted at C for 36 hours. The production rate of trimethylsilylnitrile was 55% (1H-NMR).

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

 1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

 Example 8 Production of trimethylsilyl nitrile in a non-solvent system

 Trimethylsilyl chloride (30 g, 2 76 mm o 1), sodium cyanide (15.0 g, 30 4 mm o l), potassium iodide (4 lg, 2 7. 6 mm o 1) ) Was added and reacted at 30 ° C. to 40 ° C. for 80 hours. The production rate of trimethylsilyl nitrile was 40% (1 H-NMR).

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

1H NMR (400MHz, CDC):? 0.35 (s, 9H).

Example 9 Preparation of trimethylsilyl nitrile in an organic solvent system

In a 300 ml flask, trimethylsilyl chloride (30 g, 2 76 mm o 1), n-tetradecane (15 500 g), sodium cyanide (14.9 g, 30 4 mm o 1) Iodine (1.5 g, 5.9 mm o 1) was added and reacted at 35 ° C. for 72 hours. After completion of the reaction, trimethylsilanolonitrile was obtained as a colorless liquid in 24.0 g (yield 87.6%) by simple distillation. The content was 94.2% (GC area percentage). IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

 1H NME (400MHz, CDC13) :? 0.35 (s, 9H).

 Example 1 o Preparation of trimethylsilylnitrile in an organic solvent system

 Trimethylsilyl chloride lid (30 g, 276 mm o in a 300 ml flask

1), n_tetradecane (150 g), sodium cyanide (15.0 g, 304 mm o 1), sodium hydride, (8.8 g, 27.6 mm o 1), trimethylsilylnitrile ( 1.5 g, 15.1 mmo 1) was added, and the mixture was reacted at 40 ° C for 17 hours. After completion of the reaction, simple distillation yielded 18.2 g (yield 66.4%) of trimethylsilyl-tolyl as a colorless liquid. The content was 92.8% (GC area percentage). IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

Example 11 Preparation of trimethylsilinolenitrile in organic solvent system

 Trimethylsilyl chloride (30 g, 276 mm o 1), n-hexadecane (30 g), sodium cyanide (14.9 g, 304 mm o 1), iodine (1.5 g 5.9 mmo 1) was added and reacted at 40 ° C for 48 hours. After completion of the reaction, simple distillation yielded 25.1 g (yield 91.6%) of trimethylsilylnitrile as a colorless liquid. The content was 96.2% (GC area percentage).

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

Example 12 Preparation of trimethylsilyl-tolyl in an organic solvent system

 In a 200 ml flask, trimethylsilyl chloride (30 g, 276 mm o 1), n-hexadetone (90 g), potassium cyanide (21.8 g, 304 mm o 1), iodine (1.5 g 5.9 mmo 1) was added and reacted at 40 ° C for 56 hours. After the completion of the reaction, simple distillation was performed to obtain a colorless liquid with 25.9 g of trimethylsilylnitrile force S (yield 94.5%). The content was 95.7% (GC area percentage). IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm—l.

1H NMR (400MHz, CDC):? 0.35 (s, 9H). Example 1 3 Production of trimethylsilinolenitrile in organic solvent system

 Trimethylolyl chloride (30 g 276 mm o 1) n dexade (1 50 g), sodium cyanide (14.9 g 304 mmo 1), sodium iodide (4.1 g 27) in a 300 ml flask 6 mm o 1) was added and reacted at 50 ° C for 9 hours. After completion of the reaction, simple distillation yielded 15.8 g (yield 57.7%) of trimethylsilylnitrile as a colorless liquid. The content was 94.4% (GC area percentage).

 IR (KC1, neat): 2997, 2189 1258, 854, 768, 640 cm— 1.

 1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

 Example 14 Production of trimethylsilylnitrile in an organic solvent system

 In a 200 ml flask, trimethylsilyl chloride (30 g 276 mm o 1), n-octadecane (90 g), sodium cyanide (14.9 g 30 4 mm o 1), iodine (1.5 g 5 9 mmo 1) was added and the reaction was carried out at 35 ° C for 72 hours. After completion of the reaction, simple distillation yielded 25.0 g (yield 91.3%) of trimethylsilylnitrile as a colorless liquid. The content was 95.1% (GC area percentage).

Example 15 Non-solvent reaction · Production of trimethylsilylnitrile by distillation with addition of organic solvent

Add trimethylsilyl chloride (10 g 92 mmo 1), sodium cyanide (5.0 g 101 mm ol), iodine (0.5 g 2. Ommo 1) to a 50 ml flask at 20 ° C and 30 ° C for 20 hours. Reacted. After completion of the reaction, trimethylsilylnitrile was isolated by simple distillation. During simple distillation, 15 ml of silicone oil (GE Toshiba Silicone TSF458-100) was added according to the outflow of trimethylsilylnitrile. The amount of liquid in the flask during distillation was almost constant. Furthermore, the by-product salt could be dispersed even after the distillation was completed and could be easily stirred. As a result of distillation, trimethylsilylnitrinole power S 7.2 g (yield 78.9%) was obtained as a colorless liquid. (Content: 95. 2% GC area percentage) IE (KC1, neat): 2997, 2189 1258, 854, 768, 640 cm— 1. 1H NMR (400MHz, CDC):? 0.35 (s, 9H).

 Example 16 Non-solvent reaction · Production of trimethylsilylnitrile by distillation with addition of organic solvent

 Add trimethylsilyl chloride (10 g, 92 mm o 1), sodium cyanide (5.0 g, 101 mm o 1), and iodine (0.5 g, 2. Ommo 1) to a 5 Oml flask at 20 ° The reaction was carried out at C-30 ° C for 15 hours. After completion of the reaction, trimethylsilylnitrile was isolated by simple distillation. During simple distillation, 15 ml of liquid paraffin was added according to the outflow amount of trimethylsilylnitrile. The amount of liquid in the flask during distillation was almost constant. Furthermore, the by-product salt could be dispersed even after the distillation was completed and could be easily stirred. As a result of distillation, trimethylsilylnitrile was obtained as a colorless liquid in a yield of 7.8 g (yield: 85.4%).

(Content: 98.0%, GC area percentage)

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

 1H NME (400MHz, CDC13) :? 0.35 (s, 9H).

 Example 17 Non-solvent reaction · Production of trimethylsilylnitrile by distillation with addition of organic solvent

 Add trimethylsilyl chloride (10 g, 92 mmo 1), sodium cyanide (5 O g, 101 mmo 1), iodine (0.5 g, 2. Ommo 1) to a 50 ml flask at 20 ° C. The reaction was carried out at ˜30 ° C. for 18 hours. After completion of the reaction, trimethylsilylnitrile was isolated by simple distillation. During simple distillation, 15 ml of n-tetradecane was added according to the outflow amount of trimethylsilylnitrile. The liquid volume in the flask during distillation was almost constant. Furthermore, the by-product salt could be dispersed even after the distillation was completed, and stirring was easy. As a result of distillation, trimethylsilyl nitrile was obtained as a colorless liquid at 8.0 g (yield: 87.6%). (Content: 96.2%, GC area percentage)

 IR (C1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

1H NMR (400MHz, CDC):? 0.35 (s, 9H).

Example 18 Non-solvent reaction 'trimethylsilylnitrate by distillation with addition of organic solvent Manufacture of ril

 Add trimethylsilyl chloride (10 g, 92 mm o 1), potassium cyanide (7.3 g, 101 mm ol), iodine (0.5 g, 2.0 mm o 1) to a 50 ml flask at 20 ° The reaction was carried out at C-30 ° C for 16 hours. After completion of the reaction, trimethylsilylnitrinole was isolated by simple distillation. During simple distillation, 15 ml of n-hexadecane was added according to the outflow amount of trimethylsilyl nitrile. The amount of liquid in the flask during distillation was almost constant. Furthermore, the by-product salt could be dispersed even after the distillation was completed and could be easily stirred. As a result of distillation, trimethylsilyl ditolyl force S was obtained as a colorless liquid with S7.9 g (yield 86.5%). (Content: 9

7. 0%, GC area percentage)

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

Example 1 9 Production of trimethylsilylnitrile by distillation with non-solvent reaction 'addition of organic solvent'

 Add trimethylsilyl chloride (10 g, 92 mmo 1), sodium cyanide (5.0 g, 101 mmo 1), iodine (0.5 g, 2. Ommo 1) to a 50 ml flask at 20 ° C ~ It reacted at 30 ° C for 23 hours. After completion of the reaction, trimethylsilanolonitrile was isolated by simple distillation. During simple distillation, 15 ml of n-hexadecane was added according to the outflow amount of trimethylsilylnitrile. The liquid volume in the flask during distillation was almost constant. Furthermore, the by-product salt could be dispersed even after the distillation was completed, and stirring was easy. As a result of distillation, trimethylsilyl nitrile was obtained as a colorless liquid in 7.1 g (yield 77.8%). (Content: 96.0%, GC area percentage)

 IE (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

Example 20 Production of trimethylsilylnitrile by distillation with non-solvent reaction 'addition of organic solvent'

Trimethino resilino rechloride (10 g, 92 mmo 1) in a 50 ml flask, Sodium cyanide (5.0 g 101 mmo 1) and zinc iodide (2.9 g 9. 2 mmo 1) were added and reacted at 20 ° C. and 30 ° C. for 39 hours. After completion of the reaction, trimethylsilylnitrile was isolated by simple distillation. During simple distillation, 15 ml of n-xade strength was added according to the outflow of trimethylsilylnitrile. The amount of liquid in the flask during distillation was almost constant. Furthermore, by-product salt could be dispersed even after the distillation was completed, and stirring was easy. As a result of distillation, trimethylsilylnitrile was obtained as a colorless liquid in 7.8 g (yield 85.4%). (Content: 96.6% GC area percentage)

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm-1.

 1H NMR (400MHz CDC ?? 0.35 (s, 9H).

 Example 21 Non-solvent reaction · Production of trimethylsilylnitrile by distillation with addition of organic solvent

 Into a 5 ml flask, trimethylsilyl chloride (10 g 92 mmo 1), sodium cyanide (5 O g 10 1 mm o 1), zinc oxalate (2.9 g 9. 2 mmo 1), trimethylsilanol Nitrile (0.5 g 5. Ommo 1) was added, and the mixture was reacted at 20 ° C. 30 for 32 hours. After completion of the reaction, trimethylsilylnitrile was isolated by simple distillation. During simple distillation, 15 ml of n-xadecane was added according to the outflow of trimethylsilylnitrile. The amount of liquid in the flask during distillation was almost constant. Furthermore, the by-product salt could be dispersed even after the distillation was completed and could be easily stirred. As a result of distillation, trimethylsilylnitrile was obtained as a colorless liquid in 7.4 g (yield: 81.1%). (Content: 93.2% GC area percentage)

 IE (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm-1.

1H NMR (400MHz, CDC13) :? 0.35 (s, 9H).

 Example 22 Non-solvent reaction · Production of trimethylsilylnitrile by distillation with addition of organic solvent

Trimethylsilyl chloride (10 g 92 mmo 1) _N sodium cyanide (5. O g 101 mmo l), iodine (0.5 g 2.0) in a 50 ml flask mmo 1) was added and the reaction was carried out at 20 ° C-30 ° C for 13 hours. After completion of the reaction, trimethylsilylnitrile was isolated by simple distillation. During simple distillation, 15 mL of n-octadecane was added according to the outflow amount of trimethinoresilinore nitrile. The amount of liquid in the flask during distillation was almost constant. Furthermore, the by-product salt could be dispersed even after the distillation was completed and could be easily stirred. As a result of distillation, trimethylsilyl ditrinore force S 8.4 g (yield 92.0%) was obtained as a colorless liquid. (Content: 97.4%, GC area percentage)

 IR (KC1, neat): 2997, 2189, 1258, 854, 768, 640 cm— 1.

1H NMR (400MHz, CDC):? 0.35 (s, 9H).

Claims

Claim General formula (1); [Chemical 1]

 (Wherein R 1, R 2 and R 3 are the same or different and each represents an alkyl group and A represents a halogen atom) and a general formula (2) ; [Chemical 2] M (CN) _n (2) (Wherein M is an alkali metal or alkaline earth metal, and n is 1 or 2). In the presence of a catalyst, a non-solvent system is reacted with an inorganic salt of hydrogen cyanide. A general formula characterized by (3); [Chemical 3]

(Wherein R 1, R 2 and R 3 are as defined above).  2. The method for producing trialkylsilyl nitrile according to claim 1, wherein the trialkylsilyl halide is trimethylsilyl halide.  The method for producing a trialkylsilyl nitrile according to claim 2, wherein the trimethylsilyl halide is trimethylsilyl chloride.  The method for producing trialkylsilylnitrile according to claim 1, wherein the inorganic salt of hydrogen cyanide is sodium cyanide or lithium cyanide. 5. The catalyst is iodine, zinc iodide, trimethylsilyl nitrile and mixtures thereof RRRR ^ a compound selected from the group consisting of one  1  Rear SR Le I A method for producing Kirsilylnitrile.  Three  A  General formula (1);  [Chemical 1] (Wherein R 1, R 2 and R 3 are the same or different and each represents an alkyl group, and A represents a halogen atom.) And a general formula (2) ; [Chemical 2] M (CN) _n (2) (Wherein M is an alkali metal or alkaline earth metal, and n is 1 or 2) is reacted with an inorganic salt of hydrogen cyanide represented by an organic solvent system in the presence of a catalyst. General formula characterized by (3);  [Chemical 3] (Wherein R 1, R 2 and R 3 are as defined above).  7. The method for producing trialkylsilyl-tolyl according to claim 6, wherein the trialkylsilyl halide is trimethylsilyl halide.  8. The method for producing a trialkylsilyl nitrile according to claim 6, wherein the trimethylsilyl halide is trimethylsilyl chloride.  9. The method for producing trialkylsilylnitrile according to claim 6, wherein the inorganic salt of hydrogen cyanide is sodium cyanide or lithium cyanide. 10. The catalyst is iodine, zinc iodide, trimethylsilyl nitrile or a mixture of these 7. The method for producing a trialkylsilylnitrile according to claim 6, wherein the compound is a compound selected from the group consisting of products.  11. The method for producing trialkylsilyl-tolyl according to claim 6, wherein the organic solvent is silicone oil or liquid paraffin.  12. The production of trialkylsilyl nitrile according to claim 6, characterized in that the organic solvent is decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane or eicosane. Method.  13. The method for producing a trialkylsilyl nitrile according to claim 6, wherein the reaction is carried out in a non-solvent system in the presence of a catalyst, and then an organic solvent is added and distilled.  14. The method for producing trialkylsilyl nitrile according to claim 13, wherein an organic solvent is added in accordance with the amount of distillate of trialkylsilyl nitrile during distillation.