Method for preparing amino alcohol compound, and amino alcohol compound prepared thereby

Abstract

The present invention provides a method for preparing an amino alcohol and a high-purity amino alcohol prepared thereby, the method comprising the steps of: a) introducing a Pd / C catalyst into a nitro alcohol compound and carrying out a hydrogenation reaction; and b) recovering an amino alcohol reduced by the hydrogenation reaction.

Description

Method for producing amino alcohol compound and amino alcohol compound produced by the method

[0001] The present invention relates to a method for producing an amino alcohol compound and an amino alcohol compound produced by the method.

[0002] Methods for preparing amines, especially aromatic mono-, di- or poly-amines, by catalytic hydrogenation of mono-, di- or poly-nitro compounds are well known.

[0003] Tolylenediamine (TDA), a commonly used aromatic amine, is produced by hydrogenating dinitrotoluene (DNT). It is known that hydrogenating dinitrotoluene (DNT) using conventional catalysts increases the production of reaction byproducts. Specifically, in addition to low-boiling products, deamidated or ring-hydrogenated products, high-molecular-weight products, and tar-like products are commonly produced. These reaction byproducts not only reduce process yields but can also lead to premature catalyst deactivation.

[0004] In particular, when manufacturing amino alcohols used in the biotechnology industry, the use of conventional catalysts containing heavy metals and certain metal carriers is difficult due to limitations in the content of metal impurities. Furthermore, the use of conventional catalysts results in low selectivity and the large amount of catalyst added, generating large amounts of catalyst waste, which is undesirable from both an environmental and economic perspective.

[0005] Therefore, there is a need for the development of a catalyst that can improve the above-mentioned shortcomings.

[0006] A prior patent related to the present invention is Japanese Patent Registration No. 5307103.

[0007] The present invention has been devised to solve the above problems of the prior art.

[0008] The purpose of the present invention is to provide an environmentally friendly and economical method for producing amino alcohol and an amino alcohol produced by the method, which provides the effects of high conversion rate, excellent selectivity, reduction in the content of metal impurities, reduction in the amount of catalyst used, stable reuse of catalyst, and reduction in the amount of catalyst waste when producing an amino alcohol compound by hydrogenating a nitro alcohol compound.

[0009] The present invention

[0010] a) a step of adding a Pd / C catalyst to a nitro alcohol compound and performing a hydrogenation reaction; and

[0011] b) A method for producing amino alcohol is provided, comprising a step of recovering amino alcohol reduced by the hydrogenation reaction.

[0012]

[0013] In addition, the present invention

[0014] An amino alcohol is provided by the above method.

[0015] The method for producing amino alcohol of the present invention provides the effects of high conversion rate, excellent selectivity, reduced content of metal impurities, reduced amount of catalyst used, stable reuse of catalyst, and reduced amount of catalyst waste.

[0016] In addition, the above effects enable the production of environmentally friendly and economical amino alcohols.

[0017] Since the amino alcohol of the present invention is produced by the above method, it provides high purity and excellent economic efficiency.

[0018] The present invention is described in detail below.

[0019] The method for producing amino alcohol of the present invention has the following features.

[0020] a) a step of adding a Pd / C catalyst to a nitro alcohol compound and performing a hydrogenation reaction; and

[0021] b) A step of recovering amino alcohol reduced by the above hydrogenation reaction.

[0022]

[0023] In the above step a), the nitro alcohol compound may be a compound containing at least one nitro group and at least one OH group substituted on a C1-C10 straight-chain, branched-chain, or cyclic hydrocarbon.

[0024] Specifically, the nitro alcohol compound may be tris(hydroxymethyl)nitromethane, 2-methyl-2-nitro-1-propanol, 2-methyl-2-nitro-1-propanediol, 2-ethyl-2-nitro-1,3-propanediol, 2-methyl-5-nitro-1,3-dioxane, 2-nitro-1,3-propanediol, and the like.

[0025] In the step b), the amino alcohol compound may be a compound containing one or more amino groups and one or more OH groups substituted on a C1-C10 straight-chain, branched-chain, or cyclic hydrocarbon.

[0026] Specifically, the amino alcohol compound may be tris(hydroxymethyl)aminomethane, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1-propanediol, 2-amino-2-ethyl-1,3-propanediol, 5-amino-2-methyl-1,3-dioxane, 2-amino-1,3-propanediol, etc.

[0027]

[0028] In the above step a), the nitro alcohol can be used in a dissolved state in at least one selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, cyclopropanol, butanol, cyclobutanol and water.

[0029]

[0030] The hydrogenation reaction of step a) above can be performed at a temperature of 20 to 120°C, preferably 20 to 60°C.

[0031] The hydrogenation reaction of step a) above can be performed under a hydrogen atmosphere.

[0032] The hydrogenation reaction of step a) above can be performed under a pressure of 5 to 100 bar, more preferably 30 to 50 bar.

[0033]

[0034] The above Pd / C catalyst may be added in an amount of 5 to 25 parts by weight, more preferably 5 to 15 parts by weight, based on 100 parts by weight of nitro alcohol.

[0035]

[0036] The recovery of amino alcohol in step b) above may include one or more of the following processes.

[0037] (1) Catalyst removal by filtration and centrifugation

[0038] (2) Solvent removal by concentration and reduced pressure distillation method

[0039] (3) Purification of amino alcohol by recrystallization and distillation under reduced pressure

[0040]

[0041] In addition, the present invention

[0042] An amino alcohol is provided by the above manufacturing method.

[0043] The above amino alcohol has excellent purity and economical properties.

[0044] The above amino alcohol has a purity of 95% or more.

[0045]

[0046] Hereinafter, the present invention will be described in more detail through examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by these examples. Those skilled in the art may appropriately modify or alter the following examples within the scope of the present invention.

[0047]

[0048] Example 1: Preparation of amino alcohol

[0049] A Parr MRS4871 reactor was charged with 2.25 g of tris(hydroxymethyl)nitromethane, 16.58 g of MeOH, and 0.5 g of a 5 wt% Pd / C catalyst (H2O 50 wt%), and the reactor was then sealed. To check for leaks within the reactor, nitrogen or argon gas was purged, the gas valve was closed, and pressure loss was checked. After confirming that no leaks were present, the gas inside the reactor was discharged. The process of purging and discharging nitrogen or argon was repeated three times to remove oxygen from the reactor. After three repetitions, all nitrogen or argon gas was discharged from the reactor, and hydrogen gas was used to purge the reactor to the reaction pressure. The purging and discharging process was repeated three times to create a hydrogen atmosphere. Next, hydrogen gas was purged and the pressure was increased to 40 bar. The reactor was stirred at 200 rpm and the temperature was increased to 40°C. When the target temperature was reached, the stirring speed was increased to 1500 rpm and the reaction was conducted for 2 hours. After the target reaction time, heating was stopped and stirring was stopped using a temperature controller. The hydrogen gas injection valve was closed, and all hydrogen gas in the reactor was discharged and removed. Next, all the connected reactors were separated, and the catalyst and liquid phase were separated through a filtration device using a pressure reducing pump. The separated liquid phase was distilled under reduced pressure using a rotary evaporator to remove the solvent and water, obtaining crude tris(hydroxymethyl)aminomethane.

[0050]

[0051] Comparative Example 1: Preparation of amino alcohol

[0052] A Parr MRS4871 reactor was charged with 2.25 g of tris(hydroxymethyl)nitromethane, 16.58 g of MeOH, and 0.9 g of Raney Ni 3111 catalyst (H2O 50 wt%), and the reactor was then sealed. To check for leaks within the reactor, nitrogen or argon gas was purged, the gas valve was closed, and pressure loss was checked. After confirming that no leaks occurred, the gas inside the reactor was discharged. The process of purging and discharging nitrogen or argon was repeated three times to remove oxygen inside the reactor. After three repetitions, all nitrogen or argon gas was discharged from the reactor, and hydrogen gas was purged to the reaction pressure. The purging and discharging process was repeated three times to create a hydrogen atmosphere. Next, hydrogen gas was purged and the pressure was increased to 40 bar. The reactor was stirred at 200 rpm and the temperature was increased to 40°C. When the target temperature was reached, the stirring speed was increased to 1500 rpm and the reaction was conducted for 2 hours. After the target reaction time, heating was stopped and stirring was stopped using a temperature controller. The hydrogen gas injection valve was closed, and all hydrogen gas in the reactor was discharged and removed. Next, all the connected reactors were separated, and the catalyst and liquid phase were separated through a filtration device using a pressure reducing pump. The separated liquid phase was distilled under reduced pressure using a rotary evaporator to remove the solvent and water, obtaining crude tris(hydroxymethyl)aminomethane.

[0053]

[0054] Test Example 1: Confirmation of conversion rate and selectivity of amino alcohol

[0055] Confirm that the GC equipment main unit is powered on. Confirm that the autosampler syringe is properly connected, the waste vial is empty, the washing solvent is filled, and the He, Air, and H2 gas valves are open and free of leaks.

[0056] The GC and headspace main unit were turned on, and He gas was allowed to flow through the column. Approximately 0.1 g of the samples of Example 1 and Comparative Example 1 were collected and placed in vials. 10 mL of methanol solvent was added to the vials using a reagent spoon. Ultrasonic waves were used to dissolve all the samples in the vials. Solid residues contained in the dissolved samples were filtered using a syringe filter. Approximately 1.5 mL of the filtered sample was collected and placed in a GC vial, which was then sealed using a vial cap. The sealed vials were attached to the autosampler, and the program was run to analyze the samples. The analysis results are shown in Table 1 below.

[0057] Sample used catalyst conversion rate selectivity Example 1 Pd / C 100% 96.79% Comparative example 1 Raney Ni 100% 91.79%

Claims

1. a) a step of adding a Pd / C catalyst to a nitro alcohol compound and performing a hydrogenation reaction; and b) A method for producing amino alcohol, comprising a step of recovering amino alcohol reduced by the hydrogenation reaction.

2. In paragraph 1, A method for producing amino alcohol, characterized in that in step a), the nitro alcohol compound is a compound containing at least one nitro group and at least one OH group substituted on a C1-C10 straight-chain, branched-chain, or cyclic hydrocarbon.

3. In paragraph 2, A method for producing amino alcohol, characterized in that in step a), the nitro alcohol compound is selected from tris(hydroxymethyl)nitromethane, 2-methyl-2-nitro-1-propanol, 2-methyl-2-nitro-1-propanediol, 2-ethyl-2-nitro-1,3-propanediol, 2-methyl-5-nitro-1,3-dioxane, and 2-nitro-1,3-propanediol.

4. In paragraph 1, A method for producing an amino alcohol, characterized in that in the step b), the amino alcohol compound is a compound containing at least one amino group substituted with a C1-C10 straight-chain, branched-chain, or cyclic hydrocarbon and at least one OH group.

5. In paragraph 4, A method for producing amino alcohol, characterized in that in step b), the amino alcohol compound is selected from tris(hydroxymethyl)aminomethane, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1-propanediol, 2-amino-2-ethyl-1,3-propanediol, 5-amino-2-methyl-1,3-dioxane, and 2-amino-1,3-propanediol.

6. In paragraph 1, A method for producing amino alcohol, characterized in that in step a), the nitro alcohol is dissolved in at least one solvent selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, cyclopropanol, butanol, cyclobutanol, and water.

7. In paragraph 1, A method for producing amino alcohol, characterized in that the hydrogenation reaction of step a) above is performed at a temperature of 20 to 120°C.

8. In paragraph 1, A method for producing amino alcohol, characterized in that the hydrogenation reaction of step a) above is performed under a hydrogen atmosphere.

9. In paragraph 1, A method for producing amino alcohol, characterized in that the hydrogenation reaction of step a) above is performed under a pressure of 5 to 100 bar.

10. In paragraph 1, A method for producing amino alcohol, characterized in that in step a), the Pd / C catalyst is added in an amount of 5 to 25 parts by weight based on 100 parts by weight of nitro alcohol.

11. In paragraph 1, A method for producing amino alcohol, characterized in that the recovery of amino alcohol in step b) above includes a catalyst removal process by filtration and centrifugation methods.

12. In paragraph 1, A method for producing amino alcohol, characterized in that the recovery of amino alcohol in step b) includes a solvent removal process by a concentration and reduced pressure distillation method.

13. In paragraph 1, A method for producing amino alcohol, characterized in that the recovery of amino alcohol in step b) includes a process for purifying amino alcohol by recrystallization and reduced pressure distillation.

14. Amino alcohol manufactured by the manufacturing method of paragraph 1.

15. In paragraph 14, The above amino alcohol is characterized in that it has a purity of 95% or more.