CN110981738A - Synthesis method of 2-aminopropanol - Google Patents
Synthesis method of 2-aminopropanol Download PDFInfo
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- CN110981738A CN110981738A CN201911392553.5A CN201911392553A CN110981738A CN 110981738 A CN110981738 A CN 110981738A CN 201911392553 A CN201911392553 A CN 201911392553A CN 110981738 A CN110981738 A CN 110981738A
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- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
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Abstract
The invention discloses a method for synthesizing 2-aminopropanol, which comprises the steps of taking propylene oxide and liquid ammonia as raw materials, introducing the propylene oxide and the liquid ammonia into a fixed bed reactor, wherein the mass ratio of the propylene oxide to the liquid ammonia is 1:5-20, and reacting at 100-200 ℃ for 10-60s under the action of a rare earth modified catalyst to obtain the 2-aminopropanol. The method has the advantages of reasonable process, simple and convenient operation, high atom economy and less three-waste discharge, and meets the requirement of industrial production.
Description
Technical Field
The invention relates to a synthetic method of 2-aminopropanol.
Background
Ofloxacin is a third-generation quinolone antibacterial drug with the chemical name of (+/-) -9-fluoro-2, 3-dihydro-3-methyl-10- (4-methyl-1-piperazinyl) -7-oxo-7H-pyrido [1,2,3-de ] - [1,4] benzoxazine-6-carboxylic acid. The ofloxacin has wide antibacterial spectrum, definite curative effect and low toxic and side effect, so the ofloxacin has wide clinical application, and the 2-aminopropanol is mostly adopted as the starting material for industrial production at present in China.
In the prior art, the synthesis method of 2-aminopropanol mainly comprises the following steps:
method for ammonolysis of hydroxy acetone
Monochloroacetone is adopted as a raw material, dimethyl carbonate is taken as a solvent, KI is taken as a catalyst, after acetoxylation, hydroxyacetone is obtained by hydrolysis, and then the target product 1 is prepared by reduction and ammoniation under the catalysis of Raney Ni, wherein the total yield is 44%. The reaction formula is as follows:
the hydroxyacetone related by the method has high preparation cost, large catalyst consumption and low product yield, so the method is not suitable for industrial production.
Di, alanine reduction process
The method takes alanine or alanine derivatives as initial raw materials and carries out Raney Ni hydrogenation or NaBH4Reducing by a reducing agent to obtain the 2-aminopropanol. The raw materials and reducing agents used in the method are expensive, and the method is not suitable for large-scale production.
Ammonolysis of tri, 2-chloro-1-propanol
The method uses the ring opening of the epoxypropane and the hydrochloric acid to generate the 2-chloro-1-propanol (β -chloropropanol), and then uses the 2-chloro-1-propanol as a raw material to carry out ammonolysis to prepare the 2-aminopropanol, the process solves the problem of overhigh cost of the raw material of the process, but the main product of the ring opening of the epoxypropane and the hydrochloric acid is the 1-chloro-2-propanol (α -chloropropanol), and the reaction formula is as follows:
the experimental result of Stewart C A and the like shows that the molar ratio of β -chloropropanol to α -chloropropanol is 11:89, the ring-opening reaction is also reported in China, and the result shows that the main product is α -chloropropanol, so that the operability of the process is greatly reduced, the separation difficulty is greatly increased, and no industrialized report is found.
Ammonolysis of propylene oxide
In general, when 2-aminopropanol is prepared by using propylene oxide and ammonia as raw materials, 1-aminopropanol is generated by ring opening, and 2-aminopropanol is rarely generated.
Therefore, in the prior art, the 2-aminopropanol production process has the problems of high production cost, high risk, more byproducts and the like, and researchers need to innovate research ideas to design a 2-aminopropanol preparation method suitable for industrial production.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a method for synthesizing 2-aminopropanol, which can obtain the high-selectivity synthesized 2-aminopropanol under the relatively cheap reaction condition, and has the advantages of low cost, reasonable process, simple and convenient operation, high atom economy and less three-waste discharge.
In order to achieve the purpose, the technical scheme adopted by the invention is a method for synthesizing 2-aminopropanol, which comprises the steps of taking propylene oxide and liquid ammonia as raw materials, introducing the propylene oxide and the liquid ammonia into a fixed bed reactor, wherein the mass ratio of the propylene oxide to the liquid ammonia is 1:5-20, and carrying out ring-opening addition reaction at 100-200 ℃ for 10-60s under the action of a rare earth modified catalyst to obtain the 2-aminopropanol.
In an embodiment of the invention, the rare earth modified catalyst is a hydrogen-type mordenite molecular sieve modified by rare earth nitrate, and the silicon-aluminum ratio of the hydrogen-type mordenite molecular sieve is 10-30: 1.
In an embodiment of the present invention, the rare earth nitrate is any one of cerium nitrate, lanthanum nitrate, yttrium nitrate, praseodymium nitrate, neodymium nitrate, europium nitrate, and terbium nitrate.
In one embodiment of the present invention, the silicon-aluminum ratio of the hydrogen mordenite molecular sieve is 22: 1.
In an embodiment of the present invention, the mass ratio of the propylene oxide to the liquid ammonia is 1: 10.
In an embodiment of the present invention, the reaction temperature of the ring-opening addition is 150-.
In an embodiment of the present invention, the preparation of the rare earth modified catalyst is: and (3) carrying out ion exchange on the hydrogen-type mordenite molecular sieve and a rare earth nitrate solution to obtain the rare earth modified hydrogen-type mordenite (H-MOR) molecular sieve catalyst.
In an embodiment of the invention, the concentration of the rare earth nitrate solution is 0.3mol/L, and the mass ratio of the hydrogen-type mordenite molecular sieve to the rare earth nitrate solution is 1: 15.
In one embodiment of the invention, the ion exchange is followed by washing, filtering and roasting, wherein the roasting temperature is 500-600 ℃, and the roasting time is 3-4.5 h.
In one embodiment of the invention, the temperature for ion exchange is 80-90 ℃, and the ion exchange time is 4-5 h.
The technical scheme has the following beneficial effects:
the method has the advantages of few by-product generation, high atom economy, simple reaction and convenient operation.
Through the ion exchange between the rare earth nitrate and the hydrogen mordenite molecular sieve, rare earth elements can effectively act on the molecular sieve, and because the rare earth modified hydrogen mordenite molecular sieve is used as a catalyst for reaction, the epoxypropane is mainly subjected to ring opening and ammoniation at one end of methyl substitution, so that the position selectivity of the 2-aminopropanol is greatly improved, and the selectivity of monosubstitution is also greatly improved; meanwhile, the addition of the catalyst reduces the reaction temperature of the system, so that the yield is improved.
In addition, the catalyst adopted in the invention can be used for a long time, and the use of a large amount of Raney Ni and NaBH is avoided4Reducing agents and the like, greatly reduces the cost and reduces the emission of pollutants.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
Preparation of rare earth modified catalyst A hydrogen-type mordenite molecular sieve with a silicon-aluminum ratio of 22:1 and 0.3mol/L cerium nitrate are subjected to ion exchange for 4 hours at 80 ℃ according to a solid-liquid mass ratio of 1:15, and then washed, filtered and dried, and the temperature is programmed to 550 ℃ for roasting for 4 hours to obtain a cerium modified hydrogen-type mordenite (H-MOR) molecular sieve catalyst.
Preparation of 2-aminopropanol in a tubular fixed bed reactor, placing a cerium modified catalyst, heating the system to 150 ℃, and then adding propylene oxide: and mixing liquid ammonia substances according to the mass ratio of 1:10, introducing the mixture into the tubular fixed bed reactor, and staying for 30 seconds to obtain the 2-aminopropanol.
Example 2
Preparation of rare earth modified catalyst A hydrogen-type mordenite molecular sieve with a silicon-aluminum ratio of 22:1 and 0.3mol/L lanthanum nitrate are subjected to ion exchange for 4 hours at 80 ℃ according to a solid-liquid mass ratio of 1:15, and then the hydrogen-type mordenite (H-MOR) molecular sieve modified by lanthanum is obtained by washing, filtering and drying, and roasting for 4 hours at 550 ℃ after temperature programming.
Preparation of 2-aminopropanol in a tubular fixed bed reactor, placing a lanthanum modified catalyst, heating the system to 150 ℃, and then adding propylene oxide: and mixing liquid ammonia substances according to the mass ratio of 1:10, introducing the mixture into the tubular fixed bed reactor, and staying for 30 seconds to obtain the 2-aminopropanol.
Example 3
Preparation of rare earth modified catalyst A hydrogen-type mordenite molecular sieve with a silicon-aluminum ratio of 22:1 and 0.3mol/L yttrium nitrate are subjected to ion exchange for 4 hours at 80 ℃ according to a solid-liquid mass ratio of 1:15, and then washed, filtered and dried, and the temperature is programmed to 550 ℃ for roasting for 4 hours to obtain the yttrium modified hydrogen-type mordenite (H-MOR) molecular sieve catalyst.
Preparation of 2-aminopropanol in a tubular fixed bed reactor, placing an yttrium modified catalyst, heating the system to 150 ℃, and then adding propylene oxide: and mixing liquid ammonia substances according to the mass ratio of 1:10, introducing the mixture into the tubular fixed bed reactor, and staying for 30 seconds to obtain the 2-aminopropanol.
Example 4
The preparation of the rare earth modified catalyst comprises the steps of carrying out ion exchange on a hydrogen-type mordenite molecular sieve with a silicon-aluminum ratio of 22:1 and 0.3mol/L praseodymium nitrate at a solid-liquid mass ratio of 1:15 at 80 ℃ for 4 hours, then washing, filtering, drying, and roasting at a temperature of 550 ℃ by programming to obtain the praseodymium-modified hydrogen-type mordenite (H-MOR) molecular sieve catalyst.
Preparation of 2-aminopropanol in a tubular fixed bed reactor, placing a praseodymium modified catalyst, heating the system to 150 ℃, and then adding propylene oxide: and mixing liquid ammonia substances according to the mass ratio of 1:10, introducing the mixture into the tubular fixed bed reactor, and staying for 30 seconds to obtain the 2-aminopropanol.
Comparative example 1
In a tubular fixed bed reactor, the system was warmed to 150 ℃ and then the ratio of propylene oxide: and mixing liquid ammonia substances in a mass ratio of 1:10, introducing the mixture into the tubular fixed bed reactor, and staying for 30 seconds to obtain a reaction product, wherein the generation of 2-aminopropanol is not detected through gas chromatography detection.
Comparative example 2
Placing an unmodified hydrogen mordenite (H-MOR) molecular sieve in a tubular fixed bed reactor, heating the system to 150 ℃, and then adding propylene oxide: and mixing liquid ammonia substances in a mass ratio of 1:10, introducing the mixture into the tubular fixed bed reactor, and staying for 30 seconds to obtain a reaction product, and detecting by using gas chromatography to obtain a very small amount of 2-aminopropanol.
The reaction products of examples 1 to 4 and comparative examples 1 to 2 were subjected to gas chromatography detection, respectively, to obtain the yields of the respective products, and as shown in table 1, the remaining amount of the raw material, epoxypropane, after the reaction of the system was detected, to judge the degree of the reaction.
TABLE 1
| Propylene oxide | 2-aminopropanol | 1-aminopropanol | Polysubstituted products | |
| Comparative example 1 | 100％ | 0％ | 0％ | 0％ |
| Comparative example 2 | 27.5％ | 2.4％ | 62.3％ | 7.8％ |
| Example 1 | 2.3％ | 88.6％ | 6.1％ | 3.0％ |
| Example 2 | 0.9％ | 95.9％ | 1.8％ | 1.4％ |
| Example 3 | 0％ | 98.4％ | 0.7％ | 0.9％ |
| Example 4 | 1.2％ | 93.5％ | 2.6％ | 2.7％ |
According to detection, propylene oxide and liquid ammonia are used as reaction raw materials and react under the action of a rare earth modified catalyst to generate 2-aminopropanol, 1-aminopropanol and a polysubstituted product, wherein the generated 1-aminopropanol and the polysubstituted product account for a very small amount, and the main product is the 2-aminopropanol. In comparative example 1, no 2-aminopropanol was formed in the absence of catalyst and no chemical reaction of propylene oxide occurred. In comparative example 2, however, only a small amount of 2-aminopropanol was produced, the main product being 1-aminopropanol, and also polysubstituted products, although propylene oxide was chemically reacted in the presence of the unmodified hydrogen mordenite (H-MOR) molecular sieve. Therefore, the hydrogen-type mordenite (H-MOR) molecular sieve modified by the rare earth elements can be used as a catalyst to effectively promote the ring-opening reaction of the propylene oxide to obtain the 2-aminopropanol, and the reaction selectivity is higher.
Under the action of the rare earth modified catalyst, the specific reaction formula of the epoxypropane and the liquid ammonia is as follows:
wherein, the reaction in the formula (1) generates 2-aminopropanol and 1-aminopropanol, and as the reaction of the system continues, the reaction in the formula (2) can occur among the 2-aminopropanol, 1-aminopropanol and propylene oxide, and a polysubstituted product is generated. Because the configuration of the rare earth modified catalyst enables linear molecules to easily enter and pass through, the volume of a multi-substituted product is large and the product has a branched chain, and the reaction of the formula (2) is difficult to carry out, so that the reaction selectivity is improved, and only a small amount of propylene oxide and 2-aminopropanol are consumed. In particular, in the case of the yttrium-modified hydrogen mordenite molecular sieve of example 3 as a catalyst, the reaction of the system is the most complete, and the yield of 2-aminopropanol is the highest, namely 98.4%, at this time, the propylene oxide as a reaction raw material is completely reacted, and the propylene oxide can not be detected in the reaction product.
Example 5
Performing ion exchange on hydrogen-type mordenite molecular sieves with different silicon-aluminum ratios at 80 ℃ for 4 hours by using 0.3mol/L yttrium nitrate solution according to the solid-liquid mass ratio of 1:15, washing, filtering, drying, and roasting at 550 ℃ by programming temperature for 4 hours to obtain the yttrium-modified hydrogen-type mordenite (H-MOR) molecular sieve catalyst. Placing an yttrium modified hydrogen mordenite (H-MOR) molecular sieve catalyst in a tubular fixed bed reactor, heating the system to 150 ℃, and then adding propylene oxide: the mass ratio of the liquid ammonia to the liquid ammonia is 1:10, the mixture is introduced into a tubular fixed bed reactor, the residence time is 30 seconds, and the substances and the respective occupation ratios of the substances are shown in Table 2 after the detection of the reactants by gas chromatography.
TABLE 2
| Silicon to aluminum ratio | Propylene oxide | 2-aminopropanol | 1-aminopropanol | Polysubstituted products |
| 10:1 | 8.0％ | 79.3％ | 3.2％ | 9.5％ |
| 18:1 | 2.8％ | 88.6％ | 2.0％ | 6.6％ |
| 22:1 | 0％ | 98.4％ | 0.7％ | 0.9％ |
| 25:1 | 0.3％ | 96.9％ | 0.9％ | 1.9％ |
| 30:1 | 0.2％ | 95.6％ | 0.8％ | 3.4％ |
As can be seen from Table 2, when the silica to alumina ratio of the catalyst is in the range of 10:1 to 30:1, both propylene oxide and liquid ammonia reactions can produce higher yields of 2-aminopropanol. Wherein, when the silicon-aluminum ratio is 22:1, no propylene oxide residue can be detected, and the propylene oxide is completely shrunk at the moment, so that more 2-aminopropanol is obtained, and the by-products are minimized.
Example 6
Performing ion exchange on a hydrogen-type mordenite molecular sieve with a silicon-aluminum ratio of 22:1 by using 0.3mol/L yttrium nitrate solution at 80 ℃ for 4 hours according to a solid-liquid mass ratio of 1:15, washing, filtering, drying, and roasting at 550 ℃ by programming temperature for 4 hours to obtain the yttrium-modified hydrogen-type mordenite (H-MOR) molecular sieve catalyst. Placing an yttrium modified hydrogen mordenite (H-MOR) molecular sieve catalyst in a tubular fixed bed reactor, heating the system to 150 ℃, and then adding propylene oxide: liquid ammonia is mixed according to different mass ratios and is introduced into the reactor for 30 seconds, reactants are detected by gas chromatography, and the measured substances and the respective occupation ratios are shown in table 3.
TABLE 3
| Ratio of cyclic ammonia | Propylene oxide | 2-aminopropanol | 1-aminopropanol | Polysubstituted products |
| 1:5 | 8.6％ | 80.7％ | 2.5％ | 8.2％ |
| 1:7 | 3.0％ | 87.9％ | 2.1％ | 7.0％ |
| 1:10 | 0％ | 98.4％ | 0.7％ | 0.9％ |
| 1:15 | 0％ | 96.2％ | 2.8％ | 1.0％ |
| 1:20 | 0％ | 90.0％ | 5.9％ | 4.1％ |
As can be seen from Table 3, when the mass ratio of propylene oxide to liquid ammonia is within the above range, both propylene oxide and liquid ammonia reactions can produce 2-aminopropanol in higher yield, and the propylene oxide reaction becomes more complete with the increase of the proportion of liquid ammonia, and when the cyclic ammonia ratio is 1:10, the yield of the target product is the highest and the by-products are the least.
Example 7
Performing ion exchange on a hydrogen-type mordenite molecular sieve with a silicon-aluminum ratio of 22:1 by using 0.3mol/L yttrium nitrate solution at 80 ℃ for 4 hours according to a solid-liquid mass ratio of 1:15, washing, filtering, drying, and roasting at 550 ℃ by programming temperature for 4 hours to obtain the yttrium-modified hydrogen-type mordenite (H-MOR) molecular sieve catalyst. Placing a catalyst in a tubular fixed bed reactor, heating the system to different temperatures, and then adding propylene oxide: liquid ammonia with a mass ratio of 1:10 was mixed and introduced into the reactor for a residence time of 30 seconds, and the reactants were measured by gas chromatography, and the measured substances and the respective occupancy ratios are shown in table 4.
TABLE 4
| Temperature of | Propylene oxide | 2-aminopropanol | 1-aminopropanol | Polysubstituted products |
| 100℃ | 25.5％ | 72.6％ | 0.8％ | 1.1％ |
| 130℃ | 11.9％ | 86.3％ | 0.8％ | 1.0％ |
| 150℃ | 0％ | 98.4％ | 0.7％ | 0.9％ |
| 170℃ | 1.2％ | 92.0％ | 3.6％ | 3.2％ |
| 200℃ | 2.2％ | 85.7％ | 7.8％ | 4.3％ |
As can be seen from Table 4, when the reaction temperature of the propylene oxide and liquid ammonia system is in the above range, the reaction of propylene oxide and liquid ammonia can give 2-aminopropanol in a higher yield. Particularly, when the reaction temperature is 150 ℃, the reaction of the raw materials is complete, residual 2-aminopropanol cannot be detected in reactants, the target product is generated most, and the by-products are minimized.
Example 8
Performing ion exchange on a hydrogen-type mordenite molecular sieve with a silicon-aluminum ratio of 22:1 by using 0.3mol/L yttrium nitrate solution at 80 ℃ for 4 hours according to a solid-liquid mass ratio of 1:15, washing, filtering, drying, and roasting at 550 ℃ by programming temperature for 4 hours to obtain the yttrium-modified hydrogen-type mordenite (H-MOR) molecular sieve catalyst. Placing the catalyst in a tubular fixed bed reactor, heating the system to 150 ℃, and then adding propylene oxide: liquid ammonia with a mass ratio of 1:10 was mixed and introduced into the reactor for different periods of time, and the reactants were measured by gas chromatography, and the measured substances and the respective occupancy ratios are shown in table 5.
TABLE 5
| Residence time | Propylene oxide | 2-aminopropanol | 1-aminopropanol | Polysubstituted products |
| 10s | 25.7％ | 71.8％ | 0.7％ | 0.8％ |
| 20s | 10.9％ | 86.8％ | 0.9％ | 0.8％ |
| 30s | 0％ | 98.4％ | 0.7％ | 0.9％ |
| 45s | 0％ | 98.1％ | 0.9％ | 1.0％ |
| 60s | 0％ | 98.0％ | 0.9％ | 1.1％ |
As can be seen from Table 5, when the reaction time of the propylene oxide and liquid ammonia system is in the above range, the reaction of propylene oxide and liquid ammonia can obtain 2-aminopropanol with higher yield under the condition of ensuring more sufficient reaction time, except that the yield is influenced by incomplete reaction due to too short residence time.
According to the invention, through innovative exploration on a synthesis route, the 2-aminopropanol is synthesized by performing ammonolysis on propylene oxide with high selectivity by using the rare earth modified catalyst under specific conditions, the reaction temperature for preparing the 2-aminopropanol is lower, the conversion rate of raw materials after reaction is higher, the reaction time is short, the operation is convenient, and the method is suitable for the requirements of an industrial process route.
The above-described embodiments are intended to illustrate rather than to limit the invention, and any changes and alterations made without inventive step within the spirit and scope of the claims are intended to fall within the scope of the invention.
Claims (10)
1. A method for synthesizing 2-aminopropanol is characterized in that epoxypropane and liquid ammonia are used as raw materials, epoxypropane and liquid ammonia are introduced into a fixed bed reactor, the mass ratio of the epoxypropane to the liquid ammonia is 1:5-20, and ring-opening addition reaction is carried out for 10-60s at the temperature of 200 ℃ under the action of a rare earth modified catalyst to obtain the 2-aminopropanol.
2. The method for synthesizing 2-aminopropanol according to claim 1, wherein the rare earth modified catalyst is a hydrogen mordenite molecular sieve modified by rare earth nitrate, and the silicon-aluminum ratio of the hydrogen mordenite molecular sieve is 10-30: 1.
3. The method for synthesizing 2-aminopropanol according to claim 2, wherein said rare earth nitrate is any one of cerium nitrate, lanthanum nitrate, neodymium nitrate, yttrium nitrate, europium nitrate, praseodymium nitrate and terbium nitrate.
4. The method for synthesizing 2-aminopropanol according to claim 2, wherein said hydrogen mordenite molecular sieve has a silica to alumina ratio of 22: 1.
5. The process for the synthesis of 2-aminopropanol according to claim 1, wherein said mass ratio of propylene oxide to liquid ammonia is 1: 10.
6. The method as claimed in claim 1, wherein the reaction temperature of the ring-opening addition is 150-160 ℃.
7. Process for the synthesis of 2-aminopropanol according to any of claims 2 to 6, wherein said rare earth modified catalyst is prepared by: and (3) carrying out ion exchange on the hydrogen-type mordenite molecular sieve and a rare earth nitrate solution to obtain the rare earth modified hydrogen-type mordenite molecular sieve catalyst.
8. The synthesis method of 2-aminopropanol according to claim 7, wherein the concentration of said rare earth nitrate solution is 0.3mol/L, and the mass ratio of said hydrogen mordenite molecular sieve to said rare earth nitrate solution is 1: 15.
9. The method for synthesizing 2-aminopropanol according to claim 7, wherein the ion exchange is followed by washing, filtering and roasting, wherein the roasting temperature is 500-600 ℃, and the roasting time is 3-4.5 h.
10. The process for the synthesis of 2-aminopropanol according to claim 7 wherein the temperature of ion exchange is comprised between 80 and 90 ℃ and the ion exchange time is comprised between 4 and 5 h.
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| CN114031510A (en) * | 2021-11-25 | 2022-02-11 | 万华化学集团股份有限公司 | Preparation method of 2-aminopropanol |
| CN114558577A (en) * | 2022-02-18 | 2022-05-31 | 山东新和成精化科技有限公司 | Catalyst for preparing 3-aminopropanol and preparation and application thereof |
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