Method of producing cyclohexane and derivatives thereof

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing cyclohexane and derivatives thereof of general formula R=H, . The method involves producing saturated hydrocarbons and derivatives thereof, which can be used as semi-products in organic synthesis. The method involves hydrogenation of cyclohexene or a derivative thereof, which is selected from 1-(N-piperidino)cyclohexene-1,1-(N-morpholino)cyclohexene-1 or 1,4-dicyclohex-1-enylpiperazine with hydrogen gas at atmospheric pressure of hydrogen in the presence of a nanocatalyst in tetrahydrofuran medium at temperature of 50-70°C for 5-6 hours, followed by extraction of the end product. The nanocatalyst used is nickel nanoparticles which are obtained by reducing nickel (II) chloride with lithium aluminium hydride in situ. The method can also be used to obtain a wider range of cyclohexane derivatives which contain heterocyclic groups.

EFFECT: method enables to conduct the process at atmospheric pressure using a catalyst obtained using a simpler technique, which simplifies the method overall.

4 ex

 

The invention relates to a method for producing cyclohexane and its derivatives, in particular to a new method of hydrogenation of cyclic olefins and their derivatives, which is applicable in the laboratory and allows you to get saturated hydrocarbons and their derivatives of the General formula

R=H,

which are used as intermediates in organic synthesis.

There is a method of hydrogenation of the olefins from the series: octene-1, hexene-1, hexene-2, styrene, cyclohexene hydrogen at atmospheric pressure in the presence of a specially prepared catalyst, the catalyst is produced by restoration diacetate Nickel metal sodium, zinc dust, aluminum hydride, lithium borohydride or sodium [ACTIVATION OF REDUCING AGENTS. SODIUM HYDRIDE CONTAINING COMPLEX REDUCING AGENTS. VII. NIC, A NEW HETEROGENEOUNS NI HYDROGENATION CATALYST / J.J.BRUNET, P.GALLOIS, P.CAUBERE // TETRAHEDRON LETTERS 1977, No. 45, pp.3955-3958]. The disadvantage of this method is the stage of neutralization of excessive fire hazard reducing agent, resulting in the loss of expensive reagents. The reaction products were determined by gas chromatography without highlighting.

There is a method of hydrogenation of enamines number of 1-methyl-5-aryl-2,3-dihydropyrrolo hydrogen at atmospheric pressure for metallocomplex the UNC iridium catalyst [Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Enamines // Guo-Hua Hou, Jian-Hua Xie, Pu-Cha Yan, Qi-Lin Zhou // J. Am. Chem. Soc., 2009, 131 (4), pp. 1366-1367]. The disadvantage of this method is the use of expensive iridium catalyst, this method is not the compounds of the claimed structural formulas.

The closest analogue of the present invention is a method for cyclohexane and its derivatives in the heterogeneous catalytic hydrogenation of cyclohexene and its derivatives on iron nanoparticles [At the frontier between heterogeneous and homogeneous catalysis: hydro-genation of olefins and alkynes with soluble iron nanoparticles / C.Rangheard, C. de Julian Fernandez, Pim-Huat Phua, J.Hoorn, L.Lefort, J.G. de Vries // Dalton Trans., 2010, 39, 8464-8471].

The disadvantage of this method is the necessity of using an autoclave to generate the required hydrogen pressure (20 ATM). There are also some difficulties with the preparation of the solution of catalyst, which is prepared under a nitrogen blanket in half an hour.

The objective of the proposed method is to develop a technologically advanced method of producing cyclohexane and its derivatives by hydrogenation of cyclohexene and its derivatives with gaseous hydrogen, which does not require the use of expensive catalysts and complex technological conditions, which will allow to achieve high values output by the source cyclohexane or its derivative in the chemical laboratory, using available reagents. Those who practical result is a simplification of the method of producing compounds of the claimed structural formulas.

Put the result in a new method of obtaining cyclohexane and its derivatives of General formula

R=H,

using hydrogenation with hydrogen in the presence of nanocatalysts, followed by separation of the target product, characterized in that the hydrogenation is subjected to cyclohexen or its derivatives selected from the range of: 1-(N-piperidino)cyclohexan-1, 1-(N-morpholino)cyclohexene-1 or 1,4-DICYCLOHEXYL-1-eilperin, and nanocatalysts use nanoparticles of Nickel obtained by the recovery of Nickel chloride (II) with lithium aluminum hydride in situ and the process is carried out at atmospheric pressure of hydrogen in the environment of tetrahydrofuran at a temperature of 50-70°C for 5-6 hours.

The essence of the method is the reaction of hydrogenation of cyclohexene or derived from a number: 1-(N-piperidino)cyclohexan-1, 1-(N-morpholino)cyclohexene-1 or 1,4-DICYCLOHEXYL-1-eilperin gaseous hydrogen in the environment of tetrahydrofuran in the presence of nanoparticles of Nickel.

In the present invention, the entire synthesis is carried out in one stage: obtaining a catalyst and hydrogenation occur in situ. Another advantage of p is izlagaemogo of the invention is the use of hydrogen at atmospheric pressure, allowing for an easier and cheaper way to obtain the target products.

The method is as follows.

In a flat-bottomed flask is loaded alumoweld lithium and anhydrous salt of Nickel or cobalt at a molar ratio of 1:2 reaction

2NiCl2+LiAlH4=2Ni0+LiCl+AlCl3+2H2

the solvent is tetrahydrofuran. The amount of aluminum hydride is calculated from the amount of catalyst with a slight excess, and therefore, hydroalumination reactions of cyclohexene or its derivative is not. After receiving black, transparent in a thin layer of a colloidal solution of metal loaded GearWay the substrate and through the reaction mass for 5-6 hours at a temperature of 50-70°C at atmospheric pressure barbatiruem hydrogen gas, which previously passed through the layer of concentrated sulfuric acid to remove traces of moisture. The catalyst during the reaction coagulates, and are formed agglomerates of particles, which can then be separated by filtration. If necessary for coagulation of the catalyst particles in the reaction mixture add a few drops of water. From the filtrate produce the target product by distillation at atmospheric pressure or in vacuum. Properties of synthesized compounds correspond to the literature dealing with the tion data.

Stabilization of colloidal solutions of metal nanoparticles is not required, it greatly simplifies and reduces the cost of the proposed method for the hydrogenation. As in the synthesis of the catalyst, and recovering the stated substances are used in the same conditions, the whole process is reduced to one-step synthesis in which the catalyst is formed in situ from chloride Nickel (II).

The invention is illustrated by the following examples.

Example 1.

Cyclohexane

In a flat-bottomed flask on a magnetic stirrer equipped with a bubbler and a reflux condenser, download a suspension of 0.5 g (0,013 mol) of lithium aluminum hydride in 20 ml of dried tetrahydrofuran, and then gradually sprinkled 2.7 g (0,021 mol) of anhydrous Nickel chloride (II), forming a black colloidal solution of Nickel. After that add to 36.8 g (0.40 mol) of cyclohexene and include sparging hydrogen. The reaction is carried out by heating to 60°C for 6 hours. Upon completion of the reaction the mixture is cooled, add 10 ml of water, while the colloidal catalyst is transferred to the aqueous layer. The layers separated, the organic layer is subjected to fractional distillation at atmospheric pressure to obtain 28 g (0.34 mol, 85%) cyclohexane, colorless liquid with a characteristic smell, because 80-82°C.

Example 2.

N-Cyclohexylpiperidine

In PlusCode the ing the flask on the magnetic stirrer, equipped with a bubbler and a reflux condenser, download a suspension of 0.5 g (0,013 mol) of lithium aluminum hydride in 20 ml of dried tetrahydrofuran, and then gradually sprinkled 2.7 g (0,021 mol) of anhydrous Nickel chloride (II), forming a black colloidal solution of Nickel. After that add 35 g (0.21 mol) of 1-(N-piperidino)cyclohexene-1 and include the bubbling of hydrogen. The reaction is carried out by heating to 60°C for 6 hours. Upon completion of the reaction the mixture is cooled, add 10 ml of water, while the colloidal catalyst is transferred to the aqueous layer. The layers separated, the organic layer is distilled tetrahydrofuran. The residue is distilled at atmospheric pressure, get to 31.5 g (0,189 mol, 90%) of N-cyclohexylpiperidine, colorless liquid, because 235-240°C (lit. data as 231-234°C [8]). An NMR spectrum1N, δ, ppm: 1.07-1.71 m (N, 8 CH2); 2.11 m (1H, CHN); 2.36 t (4H, CH2N).

Example 3.

N-Cyclohexylaniline

In a flat-bottomed flask on a magnetic stirrer equipped with a bubbler and a reflux condenser, download a suspension of 0.5 g (0,0 .13 mole) of lithium aluminum hydride in 20 ml of dried tetrahydrofuran, and then gradually sprinkled 2.7 g (0,021 mol) of anhydrous Nickel chloride (II), forming a black colloidal solution of Nickel. After this type of 35.1 g (0.21 mol) of 1-(N-morpholino)cyclohexene-1 and include the bubbling of hydrogen. is eakly carried out by heating to 50°C for 5 hours. Upon completion of the reaction the mixture is cooled, add 10 ml of water, while the colloidal catalyst is transferred to the aqueous layer. The layers separated, the organic layer is distilled tetrahydrofuran. The residue is distilled in a water jet vacuum pump, obtain 30.5 g (0,181 mol, 86%) of N-cyclohexylaniline, colorless liquid, because 141-142°C / 25 mm rtrt. An NMR spectrum1N, δ, ppm: 1.03-1.75 m (10H, 5 CH2); 2.06 m (1H, CHN); 2.39 t (4H, 2CH2N); 3.49 t (4H, 2CH2O).

Example 4.

N,N-Dicyclohexylurea

In a flat-bottomed flask on a magnetic stirrer equipped with a bubbler and a reflux condenser, download a suspension of 0.5 g (0,013 mol) of lithium aluminum hydride in 20 ml of dried tetrahydrofuran, and then gradually sprinkled 2.7 g (0,021 mol) of anhydrous Nickel chloride (II), forming a black colloidal solution of Nickel. Then add 25 g (0.10 mol) of 1,4-DICYCLOHEXYL-1-rilpivirine and include sparging hydrogen. The reaction is performed by heating up to 70°C for 6 hours. Upon completion of the reaction the mixture is cooled, add 10 ml of water, while the colloidal catalyst is transferred to the aqueous layer. The layers separated, the organic layer is distilled tetrahydrofuran. The residue is distilled in a water jet vacuum pump, gain of 21.3 g (of 0.085 mol, 85%) of N,N-dicyclohexylurea, colorless crystals, because 240-245°C / 20 mm Hg, TPL 98-100°C. Range of the Mr 1N, δ, ppm: 1.10-1.72 m (20N, 10 CH2); 2.06 m (2N, 2CHN); 2.39 t (8H, 2 CH2N).

Thus, the above data confirm that the implementation of the use of the claimed invention the following cumulative conditions:

the tool embodying the claimed invention in its implementation is intended for use in laboratory conditions;

for the claimed invention in the form as it is described in the independent clause following claims, confirmed the possibility of its implementation using the above described in the application or known before the priority date tools and methods;

the tool embodying the claimed invention in its implementation is able to achieve a technical result.

Conclusions

Developed a new method for producing cyclohexane and its derivatives by hydrogenation of cyclohexene or its derivatives with gaseous hydrogen at atmospheric pressure in the presence of nanoparticles of Nickel, followed by separation of the products, which proceeds with high yield on the original substances.

The method of producing cyclohexane and its derivatives of General formula

where R=H,

using hydrogenation with hydrogen in the presence of nanogate is Isadora, followed by separation of the target product, characterized in that the hydrogenation is subjected to cyclohexen or its derivatives selected from the range of: 1-(N-piperidino)cyclohexan-1, 1-(N-morpholino)cyclohexene-1 or 1,4-DICYCLOHEXYL-1-eilperin, and nanocatalysts use nanoparticles of Nickel obtained by the recovery of Nickel chloride (II) with lithium aluminum hydride in situ, and the process is carried out at atmospheric pressure of hydrogen in the environment of tetrahydrofuran at a temperature of 50-70°C for 5-6 hours



 

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