CN101648879A - Synthetic method of L-aminopropanol - Google Patents
Synthetic method of L-aminopropanol Download PDFInfo
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- CN101648879A CN101648879A CN200910184468A CN200910184468A CN101648879A CN 101648879 A CN101648879 A CN 101648879A CN 200910184468 A CN200910184468 A CN 200910184468A CN 200910184468 A CN200910184468 A CN 200910184468A CN 101648879 A CN101648879 A CN 101648879A
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Abstract
The invention provides a preparation method of L-aminopropanol, using L-alanine and H2 as main raw materials and carbon ruthenium as a catalyst to carry out direct catalytic hydrogenation to synthesize the L-aminopropanol. The method increases the selectivity of process reaction, accelerates reaction speed and shortens reaction step, thereby greatly reducing the production cost, increasing the L-aminopropanol yield, reducing the production of harmful wastes and realizing the greenization of the reaction process; and the aspects of energy saving and emission reduction of SOD and SO2 are obviously improved in order to realize less environment pollution. Any organic solvent is not added to the whole reaction process, thereby reducing the emission of pollutants, and protecting environment.
Description
Technical field
The present invention relates to a kind of preparation method of fine chemicals, particularly a kind of preparation method of medicine intermediate specifically, relates to a kind of synthetic method of L aminopropanol.
Background technology
The L-aminopropanol is the key intermediate of synthetic Levofloxacin, Levofloxacin (levofxcain, DR-3355) be the left-handed optical isomer of S shape of Ofloxacine USP 23 Zanocin, anti-microbial activity is the latter's a twice, toxic side effect is little, water-soluble big, be one of extensive pedigree antibiotic outstanding in the quinolones.The anti-microbial activity of Levofloxacin be enantiomorph 8-128 doubly, to intestinal tract infections, gonococcal infection is efficient reaches 100%, is one of large medicine of present clinical use.This product is succeeded in developing the beginning of the nineties in last century by Japanese Daiichi Pharmaceutical Co., Ltd. the earliest, nineteen ninety-five formally enters Chinese market, began to realize production domesticization in 1997, subsequently, the market sales revenue of levofloxacin is soaring rapidly, leaps to the domestic antibiotic pharmaceutical market first place of dying in 2002, annual sales amount reaches 12,447 ten thousand yuan, account for 2.08% of medical market share, alternative Ciprofloxacin becomes the soldier at the head of a formation in this market, and annual average rate of increase is about 10%.2007, year consumption sum of levofloxacin was firmly in occupation of the position of the market ranking first, and the market share continues taking on the role of leading kind also in occupation of the half of the country of fluoroquinolones.
There are a plurality of producers in China at present, system production Levofloxacin.Along with Levofloxacin is gone on the market at home as national essential drugs, it is extremely important that the synthetic method of intermediate just seems.Generally adopt first esterification to restore to produce the L-aminopropanol both at home and abroad, i.e. two step of POTASSIUM BOROHYDRIDE reaction method, cost of material height, yield are low; And use KBH
4As catalyzer, during solvent recuperation, sizable pollutent is arranged, as solid waste such as waste water, waste gas and borides, be difficult for handling, be unfavorable for environment protection.
The synthetic method of L-aminopropanol, conclusion is got up, and mainly contains the synthetic and chemical resolution method of stereoselectivity and prepares approach for two kinds.Because chemical resolution method is not suitable for industrialized production, thereby various countries are primarily aimed at and select synthesis method to study to solid.
At present domestic have several approach to Stereoselective synthesizing process:
(1) direct-reduction process: utilize LiAlH
4Reduction L-L-Ala is produced the L-aminopropanol, at 5%LiAlH
4THF solution in reflux, use CH
2Cl
2A certain amount of water treatment is used in dilution again, filters to remove inorganic salt, and filter cake is handled and can be reached promising result twice, and yield reaches 75%.The method of reducing process is simple, but reductive agent LiAlH
4Cost an arm and a leg and operational hazards, last handling process is too complicated in addition, so method has rarely had employing at present.
(2) esterification reduction method: utilize L-L-Ala and SOCl
2Reaction generates ester with dehydrated alcohol, at NaBH
4Drip the ethanolic soln 1h of L-alanine ethyl ester (L-alanine ethyl ester) in the aqueous solution continuously, and continue to stir 3h under room temperature, reduction obtains the L-aminopropanol, with underpressure distillation after the ethyl acetate extraction, and yield 67%.
(3) esterification reduction method synthesis technique, detailed process as shown in Figure 1.
In two kinds of method of reducing of above-mentioned synthetic L-aminopropanol, though reaction conditions all compares gentleness, employed NaBH in the reduction method
4, LiAlH
4Reductive agent costs an arm and a leg, inflammable; dangerous higher; and has stronger toxicity; and separation and purification of products program complexity, be unfavorable for suitability for industrialized production, in synthetic and the sepn process in a large number with an organic solvent; difficult solvent recovery in the production process; there is a large amount of pollutents,, very is unfavorable for environment protection as waste water, waste gas, solid waste etc.
Esterification reduction method in addition needs to restore just through esterification earlier to obtain target product, has increased reactions steps undoubtedly, has prolonged the production cycle, has increased production cost, and these have all limited the application of this synthetic method in industrial production.
In recent years, country advocates the green chemical industry technology, in field of fine chemical, focus development hangs down the technology that evil raw material, solvent and catalyzer substitute high poison high evil raw material, solvent and catalyzer with nontoxic or low toxicity, realizes the greenization of raw material, solvent and catalyzer.This makes the green synthesis process project of L-aminopropanol have more important environment protection significance and social benefit.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of L-aminopropanol, this method adopts the shortening single step reaction, can improve the selectivity of technological reaction, fast reaction speed, shorten reactions steps, improve L-aminopropanol yield, reduce the generation of bazardous waste.
In order to realize the object of the invention, the present invention is through great deal of experimental, and find out a whole set of cleaning, environmental protection, synthetic route efficiently: adopting L-alanine and H2 is main raw material, and the ruthenium charcoal is a catalyzer, carry out the technology of the synthetic L-aminopropanol of direct shortening, reaction scheme is short, has maximally utilised resource, the yield height, the atom utilization height, significantly reduce the use of organic solvent, reduced environmental pollution, embodied the feature of Green Chemistry " Atom economy ".
The preparation method of a kind of L-aminopropanol of the present invention, it comprises the steps:
1) earlier that the L-L-Ala is soluble in water, be that 85% sulfuric acid mixes with mass percent then;
2) add ruthenium Pd/carbon catalyst and feed hydrogen again, the control control reaction temperature is 80-90 ℃, and pressurization 8-9Mpa stirred 5-6 hour with 500-600 rev/min.
3) after reaction finishes, filter to get filtrate, and carry out underpressure distillation, the concentrated solution after the distillation forms through centrifugal, rectifying.
Wherein, L-L-Ala and vitriolic weight ratio are (1-1.2) in the step 1): 1;
Step 2) ruthenium content 10% of ruthenium Pd/carbon catalyst in, particle diameter 100-150 order, specific surface area＞1000 square meter/grams, metal specific surface area 40-60 square meter/gram, water ratio 45%.
Described ruthenium Pd/carbon catalyst consumption and L-L-Ala mass ratio are (4.8-5): 1, and the mol ratio of L-L-Ala and hydrogen is 1: (5-5.5).
The filter cake that filters gained in the step 3) is a catalyzer, can turn back to step 2), be used for batch reaction down.
The water that underpressure distillation goes out can be used for dissolving L-L-Ala in the step 1).
Underpressure distillation in the inventive method step, centrifugal, rectifying all can adopt the processing condition of this area routine to carry out.
The L-aminopropanol purity that method of the present invention obtains can reach more than 99%.
Reaction formula of the present invention is as follows:
The present invention is a main raw material with L-alanine (L-L-Ala), and directly catalytic hydrogenating reduction prepares the L-aminopropanol, after processes such as separation, purification finally obtain qualified product (GC purity 〉=99.0%).Can improve the selectivity of technological reaction, fast reaction speed shortens reactions steps, greatly reduces production cost, improves L-aminopropanol yield, reduces the generation of bazardous waste, the greenization of realization response process, and energy-conservation, reduce discharging SOD and SO
2There is more significantly raising the aspect, realizes less environmental pollution.Do not add any organic solvent in the entire reaction course, reduced the discharging of pollutent, protected environment.
The L-aminopropanol product that adopts the inventive method to obtain detects through Zhejiang Province's quality of chemical products test house company limited, reaches standard.The key technical indexes detects as follows:
| Sequence number | The key technical indexes | The index performance |
| ??1 | Quality index: content 〉=99.0%, moisture content＜1%, specific optical rotation+17 °～+ 18 °, maximum contaminant＜0.5% | Product sampling inspection result: content 99.9%, moisture are less than 0.3%, and specific optical rotation+17.8 ° total impurities is less than 0.3%, and single impurity is less than 0.1% |
Description of drawings
Fig. 1 is an esterification reduction method synthesis process flow diagram in the prior art;
Fig. 2 prepares the process flow sheet of L-aminopropanol for catalytic hydrogenating reduction of the present invention.
Embodiment
Further describe the present invention with embodiment below, help understanding, but described embodiment only is used to illustrate the present invention rather than restriction the present invention the present invention and advantage thereof, better effects if.
Embodiment 1
The preparation method of a kind of L-aminopropanol of present embodiment, it comprises the steps:
1) earlier the 50gL-L-Ala being dissolved in 500 milliliters the deionized water, is that 85% sulfuric acid mixes with the mass percent of 50g then;
2) add 250g ruthenium Pd/carbon catalyst and feed 5.6g (2.8mol) hydrogen again, 88 ± 2 ℃ of control reaction temperature, pressurization 8MPa stirred 6 hours with 500 rev/mins;
3) after reaction finishes, filter to get filtrate, underpressure distillation in concentration kettle, boil off water, the concentrated solution cooling, the after-filtration that stirs is removed insoluble substance wherein, and the pure filtrate that obtains is gone rectifying tower rectifying, behind high vacuum rectification, obtaining purity and be 99.5% L-aminopropanol, specific optical rotation reaches+and 17.70 °.
Filter the filter cake that contains the ruthenium Pd/carbon catalyst of gained, can turn back to step 2), be used for batch reaction down.The water that underpressure distillation goes out can be used for dissolving L-L-Ala in the step 1).
Wherein, the ruthenium Pd/carbon catalyst is available from Xi'An Catalyst Chemical Co., Ltd., its ruthenium content 10%, particle diameter 100-150 order, specific surface area＞1000 square meter/grams, metal specific surface area 40-60 square meter/gram, water ratio 45%.
Embodiment 2
The preparation method of a kind of L-aminopropanol of present embodiment, it comprises the steps:
1) earlier the 120gL-L-Ala being dissolved in 850 milliliters the deionized water, is that 85% sulfuric acid mixes with the mass percent of 100g then;
2) add 576g ruthenium Pd/carbon catalyst and feed 12.32g (6.16mol) hydrogen again, control reaction temperature is 82 ± 2 ℃, and pressurization 9MPa stirred 5 hours with 600 rev/mins;
3) after reaction finishes, filter to get filtrate, underpressure distillation in concentration kettle, boil off water, the concentrated solution cooling, the after-filtration that stirs is removed insoluble substance wherein, and the pure filtrate that obtains is gone rectifying tower rectifying, behind high vacuum rectification, obtaining purity and be 99.9% L-aminopropanol, specific optical rotation reaches+and 17.8 °.
Filter the filter cake that contains the ruthenium Pd/carbon catalyst of gained, can turn back to step 2), be used for batch reaction down.The water that underpressure distillation goes out can be used for dissolving L-L-Ala in the step 1).
Experimental example 1
The good and bad effect that directly influences hydrogenation reduction of catalyzer, the hydrogenation reaction multiselect is a catalyzer with Pd/C, Pt/C etc.When hydrogenating reduction uses the nickel catalyzator poor effect, can select noble metal catalyst palladium, platinum, rhodium etc.
The preparation of ruthenium Pd/carbon catalyst
Activated carbon supported nail catalyzer is widely used for catalyzer as hydrogenation reaction owing to having good hydrogenation performance.The method for preparing the ruthenium Pd/carbon catalyst has pickling process, ion exchange method and liquid phase reduction.
(a) the pickling process pickling process mainly is that gac and parent are flooded for some time in certain solvent, make parent compound can be adsorbed on carrier surface more equably, filtration or solvent evaporated then at a certain temperature, oven dry, reduce under the temperature of setting with high-purity hydrogen again, make the parent that is adsorbed in activated carbon surface change into metal Ru, promptly get loading type Ru/C catalyzer.In this process, proofing and reductive condition are the principal elements that influences catalyst activity.
(b) ion exchange method adopts to prepare the Ru/C catalyzer with ion exchange method.To impregnated in the water with the clorox processed active carbon, at following Ru (NH of nitrogen protection
3) 6Cl
3Solution slowly adds in the solution that is suspended with gac, at room temperature stirs and carries out ion-exchange in 24 hours, filters, and is washed to neutrality, the oven dry reduction, and catalyzer gets product.
(c) liquid phase reduction has adopted liquid phase reduction to prepare the Ru/C catalyzer.Gac is added in the deionized water, at the following RuCl of nitrogen protection
3Salts solution add and to be suspended with in the water of gac, make suspension cool to 0 ℃, the KOH solution that adds a certain amount of formaldehyde and 30% reduces, and stirs 15 hours after-filtration, is washed to neutrality, dries promptly to get required catalyzer.
According to the different qualities of above several catalyzer, through repetition test, the quality and the technical indicator situation of the experiment effect of the relatively above catalyzer of analysis, the L-aminopropanol that obtains determine that finally with the ruthenium Pd/carbon catalyst be the first-selected catalyzer of this project.
Experimental example 2 lab scale operational paths of the present invention
Researchist of the present invention through study repeatedly, test, lab scale etc., develop one and produce the effective and lower production technology of pollution level of L-aminopropanol: with the L-alanine is main raw material, direct hydrogenation prepares the L-aminopropanol, separate purification process through aftertreatment, adopt the ruthenium Pd/carbon catalyst, making up-to-standard (purity 〉=99.0%) of product, the key technical indexes specific optical rotation reaches+and 17 °～+ 18 °.
1. the preparation of reaction feed liquid
(1) take by weighing the L-L-Ala of 50 grams with electronic balance, be dissolved in 500 milliliters the water:
(2) massfractions of getting 50 grams with balance are 85% sulfuric acid, sulfuric acid are added slowly in the solution that (1) prepare, and add sulfuric acid and will stir simultaneously, and the preparation back that finishes is stand-by.
2. reactions steps
(1) opens the pneumatic outlet valve, reactor (FCH-1L) is communicated with atmosphere, open the charging valve, the reaction feed liquid for preparing is poured in the reactor with funnel, add catalyzer in the time of stirring slowly, close the pneumatic outlet valve;
(2) in still, vacuumize with vacuum pump (2SK-3), vacuum tightness reaches-0.10Mpa in still, close vacuum valve, feed nitrogen to pressure 0.4Mpa, emptying leaves the pressure of 0.05Mpa, feed nitrogen again to pressure 0.4Mpa, repeat twice, displace the air in the still, use hydrogen exchange nitrogen again, same operation displaces the nitrogen in the still, and displacement finishes.
(3) open the hydrogen inlet valve, treat to stop ventilation after the still internal pressure rises to required reaction pressure, close the inlet mouth valve;
(4) open the agitator motor water of condensation, establishing and stirring revolution is 500rad/min, begins to stir;
(5) set Heating temperature and be predetermined temperature of reaction, beginning heat temperature raising, timing, reaction beginning;
(6) after reaction finishes, open the kettle water of condensation, make it be cooled to room temperature:
(7) off-response still inlet mouth valve and hydrogen gas cylinder outlet valve are opened the air outlet valve, make the still internal pressure reduce to normal pressure.
(8) filtrate underpressure distillation in concentration kettle boils off water, the concentrated solution cooling, and the after-filtration that stirs is removed insoluble substance wherein, and the pure filtrate that obtains is then gone rectifying tower rectifying, obtains final product behind high vacuum rectification.
Experimental example 3 pilot process routes of the present invention
(1) reactions steps is as follows:
I, decolouring batching
Add entry in the decolouring still, open and stir, add sulfuric acid, drop into quantitative L-Ala, add gac, Yu Zhongwen stirs decolouring.Decolouring is finished and to be entered the millipore filter suction filtration, and filtrate is returned and added catalyzer in the batching still and stir.
II, hydrogenating reduction
Material in the batching still is drawn in the hydrogenation reaction kettle hydrogenating reduction with the vacuum unit.This reaction conversion ratio is more than 90%, and reaction equation is as follows:
III, blowing filter
Put after material extrudes with nitrogen from the hydrogenation still to filter pocket and carry out suction filtration, filtrate sucks in the concentration kettle; Filter cake is a catalyzer, can overlap to be used for batch reaction down.
IV, distillation concentrate, rectifying
Filtrate is underpressure distillation in concentration kettle, boils off water, and the concentrated solution cooling is put after stirring to the centrifugal removal of whizzer insoluble substance wherein, and the pure filtrate that obtains is then gone rectifying tower rectifying, obtains final product behind high vacuum rectification.
The present invention has the following advantages:
(1) adopt the ruthenium Pd/carbon catalyst to substitute the Green Chemical Technology of sodium borohydride, POTASSIUM BOROHYDRIDE: to get rid of the use of the big thionyl chloride of environmental pollution in the traditional technology, realized the greenization and the ecology of production process; Solved also in the past that carboxylic acid can not directly reduce or be difficult to a reductive difficult problem, technical process is simplified greatly, and it is about about 20% that the cost amplitude reduces, and yield is brought up to more than 90%, and environmental pollution reduces greatly.
(2) replace inflammable and explosive organic solvent with deionized water, security improves greatly.And in producing in the process gaseous emission be green.In general traditional technological process, be to be organic solvent with thionyl chloride, ethanol, thus give off some toxic gases in the reaction process, and easy explosive combustion.But with the deionized water replace organic solvent, emission gases is hydrogen and a spot of ammonia nitrogen, does not have problem of environment pollution caused in the synthesis technique of the present invention.
Simultaneously, solid catalyst can reclaim and reuse, and exhaust gas emission etc. also can be reduced to quite low level, reaches national environmental standard fully.
The present invention adopts the hydrogenating reduction method directly to prepare, with the L-alanine is main raw material, is solvent with the deionized water, behind activated carbon decolorizing, under the effect of ruthenium Pd/carbon catalyst, through hydro-reduction, blowing filter, processes such as distillation concentrates, rectifying obtain L-aminopropanol product.
L-aminopropanol green synthesis process of the present invention replaces inflammable and explosive organic solvent with deionized water, and security improves greatly; Solvent recuperation is applied mechanically, and the rate of recovery can reach more than 90%, reaches zero release substantially, has greatly improved environment-friendly type; The key technical indexes specific optical rotation can reach+17.8 ° between+17 °～+ 18 °; Solid catalyst can reclaim and activate recycling repeatedly, and exhaust gas emission etc. also can be reduced to quite low level, reach national environmental standard fully.
The ruthenium Pd/carbon catalyst is produced down the L-aminopropanol that draws and esterification and is reduced the L-aminopropanol of producing under the two step process methods, and both technical indicators contrast:
| The technical indicator title | The novel technique index | The conventional process techniques index |
| Specific optical rotation | ??+17.8° | ??+17.2°-+17.3° |
| Moisture content | ??＜0.5％ | ??＜1％ |
| Purity | ??≥99.8％ | ??＞99％ |
| Solvent recovering rate | ??＞90％ | ??＞70％ |
Aspect energy-conservation, reduction of discharging, both relatively are:
| Content | Novel process down blow amount | Traditional technology down blow amount |
| Waste gas t/a | ??1.56 | ??7.8 |
| Waste water m 3/a | ??4516 | ??4711 |
| Gu refuse t/a | ??0 | ??66.59 |
As seen, the present invention adopts and prepares the L-aminopropanol with ruthenium Pd/carbon catalyst direct hydrogenation, separate purification process through aftertreatment, require the synthesis route of up-to-standard (GC purity 〉=99.0%) of product, than traditional technology route purity height, yield is also high, and specific optical rotation be controlled at+17 °-+18 °.
Although the present invention has been done detailed explanation and quoted some specific exampless as proof, for a person skilled in the art, only otherwise leave the spirit and scope of the present invention, it is obvious doing various variations or correction.
Claims (7)
1. the synthetic method of a L-aminopropanol is characterized in that, it adopts L-alanine and H2 is main raw material, and the ruthenium charcoal is a catalyzer, carries out the synthetic L-aminopropanol of direct shortening.
2. method according to claim 1 is characterized in that it comprises the steps:
1) earlier that the L-L-Ala is soluble in water, be that 85% sulfuric acid mixes with mass percent then;
2) add ruthenium Pd/carbon catalyst and feed hydrogen again, the control control reaction temperature is 80-90 ℃, and pressurization 8-9MPa stirred 5-6 hour with 500-600 rev/min.
3) after reaction finishes, filter to get filtrate, and carry out underpressure distillation, the concentrated solution after the distillation forms through centrifugal, rectifying.
3. method according to claim 2 is characterized in that, L-L-Ala and vitriolic weight ratio are (1-1.2) in the step 1): 1.
4. according to claim 2 or 3 described methods, it is characterized in that step 2) described in the ruthenium content 10% of ruthenium Pd/carbon catalyst, particle diameter 100-150 order, specific surface area＞1000 square meter/grams, metal specific surface area 40-60 square meter/gram.
5. according to any described method of claim 2-4, it is characterized in that the mass ratio of described ruthenium Pd/carbon catalyst consumption and L-L-Ala is (4.8-5): 1, the mol ratio of L-L-Ala and hydrogen is 1: (5-5.5).
6. method according to claim 2 is characterized in that, the filter cake that filters gained in the step 3) is a catalyzer, turns back to step 2), be used for batch reaction down.
7. method according to claim 2 is characterized in that, the water that underpressure distillation goes out is used for step 1) dissolving L-L-Ala.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103769211A (en) * | 2014-01-24 | 2014-05-07 | 淮北新兴实业有限责任公司 | Preparation method of organic-inorganic hybrid material ruthenium-loaded catalyst for synthesizing L-alaninol |
| CN110483314A (en) * | 2019-07-19 | 2019-11-22 | 温州大学新材料与产业技术研究院 | A kind of full green synthesis method and its device of chiral beta-alkamine compound |
| CN113121368A (en) * | 2021-03-29 | 2021-07-16 | 安徽华恒生物科技股份有限公司 | Method for preparing gamma-aminopropanol by one-step catalytic hydrogenation and application thereof |
| CN114573463A (en) * | 2022-03-23 | 2022-06-03 | 江西宇能制药股份有限公司 | Preparation method of R-3-aminobutanol |
| CN115417776A (en) * | 2022-08-23 | 2022-12-02 | 万华化学集团股份有限公司 | Method for preparing 2-amino-1-propanol |
| CN115819253A (en) * | 2022-11-18 | 2023-03-21 | 安徽华恒生物科技股份有限公司 | Method for preparing 3-aminopropanol by using fixed bed reactor |
| CN115888701A (en) * | 2022-11-28 | 2023-04-04 | 江西宇能制药股份有限公司 | Catalyst for preparing L-aminopropanol by catalytic hydrogenation and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103769211A (en) * | 2014-01-24 | 2014-05-07 | 淮北新兴实业有限责任公司 | Preparation method of organic-inorganic hybrid material ruthenium-loaded catalyst for synthesizing L-alaninol |
| CN110483314A (en) * | 2019-07-19 | 2019-11-22 | 温州大学新材料与产业技术研究院 | A kind of full green synthesis method and its device of chiral beta-alkamine compound |
| CN113121368A (en) * | 2021-03-29 | 2021-07-16 | 安徽华恒生物科技股份有限公司 | Method for preparing gamma-aminopropanol by one-step catalytic hydrogenation and application thereof |
| CN114573463A (en) * | 2022-03-23 | 2022-06-03 | 江西宇能制药股份有限公司 | Preparation method of R-3-aminobutanol |
| CN115417776A (en) * | 2022-08-23 | 2022-12-02 | 万华化学集团股份有限公司 | Method for preparing 2-amino-1-propanol |
| CN115417776B (en) * | 2022-08-23 | 2024-04-09 | 万华化学集团股份有限公司 | Method for preparing 2-amino-1-propanol |
| CN115819253A (en) * | 2022-11-18 | 2023-03-21 | 安徽华恒生物科技股份有限公司 | Method for preparing 3-aminopropanol by using fixed bed reactor |
| CN115888701A (en) * | 2022-11-28 | 2023-04-04 | 江西宇能制药股份有限公司 | Catalyst for preparing L-aminopropanol by catalytic hydrogenation and preparation method and application thereof |
| CN115888701B (en) * | 2022-11-28 | 2023-10-10 | 江西宇能制药股份有限公司 | Catalyst for preparing L-aminopropanol by catalytic hydrogenation and preparation method and application thereof |
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| CN101648879B (en) | 2012-08-22 |
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