CN101660171B - Method for preparing aminopropanol by electrolysis - Google Patents
Method for preparing aminopropanol by electrolysis Download PDFInfo
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- CN101660171B CN101660171B CN2009101448989A CN200910144898A CN101660171B CN 101660171 B CN101660171 B CN 101660171B CN 2009101448989 A CN2009101448989 A CN 2009101448989A CN 200910144898 A CN200910144898 A CN 200910144898A CN 101660171 B CN101660171 B CN 101660171B
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- Prior art keywords
- aminopropanol
- catholyte
- electrolytic
- preparation
- electrolysis
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- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000005868 electrolysis reaction Methods 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001413 amino acids Chemical class 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 239000003014 ion exchange membrane Substances 0.000 claims abstract description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 7
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 7
- 235000001014 amino acid Nutrition 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 235000004279 alanine Nutrition 0.000 claims description 6
- 239000010405 anode material Substances 0.000 claims description 5
- 239000008151 electrolyte solution Substances 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000010406 cathode material Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000004821 distillation Methods 0.000 abstract description 3
- 239000003792 electrolyte Substances 0.000 abstract 2
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000011110 re-filtration Methods 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 6
- 229960003767 alanine Drugs 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229960003376 levofloxacin Drugs 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229950010030 dl-alanine Drugs 0.000 description 1
- 238000003411 electrode reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for preparing aminopropanol by electrolysis comprises two steps, namely preparation of aminopropanol by electrolysis reduction of an amino acid cathode and purification; the method for preparing aminopropanol by electrolysis is characterized in that an ion exchange membrane is adopted to divide an electrolyzer into a negative chamber and a positive chamber; the concentration of the aminopropanol in catholyte is 0.3mol/L to 2.0mol/L; the pH of the catholyte is 1 to 4; the anolyte is sulfuric acid with mass percentage concentration of 2 percent to 20 percent; the temperature of the electrolyte is controlled to be from 30 DEG C to 60 DEG C; the current density is 200 A/m<2> to 2000 A/m<2>; and when electrolyte balance is reached, the aminopropanol is obtained after the catholyte experiences filtration, neutralization, re-filtration and distillation. The method for preparing aminopropanol by electrolysis has low production cost and no pollution in the production process.
Description
Technical field
The present invention relates to the preparation method of aminopropanol, more precisely is a kind of method for preparing aminopropanol with the water-soluble amino acid of electrolytic reduction.
Background technology
Aminopropanol has vast market prospect, fine chemistry industry and pharmaceutical industry in World chemical product market in 2002, and its sales volume reaches 7,000,000,000 and 1,590 hundred million dollars respectively.The L-aminopropanol is the important intermediate of synthetic third generation quinolones broad spectrum antibiotic Levofloxacin, its optical purity and price directly have influence on the quality and the price of Levofloxacin, it is important source material, intermediate and the chiral auxiliary(reagent) in pharmacy and the agribusiness simultaneously, has a wide range of applications as chiral source and chirality modifier in asymmetric synthesis.Its preparation is based on reduction method, as patent: 01127017.9; 200710190457.3; Disclosing with the L-alanine is starting raw material, prepares the method for aminopropanol with metal borohydride as reductive agent, and has obtained industrial application.The industrialization of still being unrealized of shortening method and biological synthesis process.Patent: 200610029053.1; 200710067973.7; Disclosing with the propylene oxide is starting raw material, prepares the method for aminopropanol through phase-transfer catalysis.Realized at present the method for industrialized production aminopropanol, its reductive agent consumption is big, cost an arm and a leg, and 1 ton of aminopropanol of every production will consume 2.5 tons of reductive agent KBH
4, this individual event cost promptly reaches 220,000 yuan, and reaction conditions requires height and long reaction time, and reaction efficiency is low, the residue contaminate environment.
Catalytic hydrogenating reduction just with its environmental friendliness, easy and simple to handlely be subjected to common concern.But up to now, the method for preparing aminopropanol with the water-soluble amino acid of electrolytic reduction does not have open report as yet.
Summary of the invention
The present invention is for avoiding above-mentioned existing in prior technology weak point, a kind of method of electrolytic preparation aminopropanol is provided, to reduce the production cost of aminopropanol, reducing the pollution of production process to environment.
The present invention adopts following technical scheme for the technical solution problem:
The method of electrolytic preparation aminopropanol of the present invention, comprise the amino acid catholyte reduction preparation aminopropanol and two steps of purifying, it is characterized in that adopting ion-exchange membrane that electrolyzer is divided into negative and positive two Room, the concentration of alanine is 0.3～2.0mol/L in the catholyte, and the pH of catholyte is 1～4; Described anolyte is that concentration is 2～20% sulfuric acid by mass percentage; The temperature of control electrolytic solution is 30～60 ℃, current density 200～2000A/m
2After reaching electrolytic equilibrium, with catholyte after filtration, neutralize, refilter, distill and promptly get aminopropanol.
The characteristics of electrolytic preparation aminopropanol method of the present invention also are:
Described catholyte consists of by mass ratio: alanine 15～35, water 80～60, sulfuric acid and vitriol 4～4.5, catalyzer 1～0.5.
The catalyzer that adds in the described catholyte is the loaded article of Re, Ru, Cu, Ni, Pd simple substance or its compound, and carrier is carbon, aluminum oxide or silica gel.
The cathode material that is provided with in the described electrolyzer is platinum, molybdenum, lead or the graphite with katalysis; Anode material is the inert material of acid corrosion-resistant.
Described anode material is platinum or molybdenum.
The principle of foundation of the present invention is: in electrolytic process, and the H of anolyte compartment
+Enter cathode compartment by cationic exchange membrane, at negative electrode H
+Get electronics and be reduced into atomic hydrogen and amino acid whose carboxyl generation reduction reaction.Electrode reaction is:
Anode: H
2O-2e=2H
++ 1/2O
2
Negative electrode: 2H
++ 2e=H
2
2H
2+R-CH(NH
2)-COOH→R-CH(NH
2)-CH
2OH+H
2O
Compared with the prior art, beneficial effect of the present invention is embodied in:
1, the inventive method is because of the inexpensive remarkable cost that reduces the preparation aminopropanol of raw material.
2, reaction conditions gentleness of the present invention, no residue.The oxyethane that adopts in the technology of having reported is inflammable explosive article; Borane reducing agent hydride is met wet inflammable, residue is arranged, contaminate environment after the reaction.
3, electrolytic reduction of the present invention carries out at normal pressure, room temperature condition, safety, easily control, and catalyzer can be reused.The catalytic hydrogenating reduction of report is to carry out under High Temperature High Pressure, and catalyzer can not be reused.
4, the inventive method is suitable for the preparation of water soluble amino alcohol, comprises that all water-soluble amino acids can adopt the inventive method to be prepared corresponding amino alcohol.
Embodiment
In the present embodiment, adopt ion-exchange membrane that electrolyzer is divided into cathode compartment and anolyte compartment, in cathode compartment and anolyte compartment, place 30～60 ℃ of the temperature that the prolong that is used to reduce utmost point room temp is regulated electrolytic solution respectively.
Cathode material adopts platinum, molybdenum, lead flake or graphite rod;
Anode material is corrosion resistant inert material, can be platinum or molybdenum sheet.
In the concrete preparation, the concentration of alanine is 0.3～2.0mol/L in the catholyte, and the pH of catholyte is 1～4; Anolyte is 2～20% sulfuric acid by the concentration of mass ratio; The temperature of control electrolytic solution is 30～60 ℃, current density 200～2000A/m
2After reaching electrolytic equilibrium, will neutralize, refilter with sodium hydroxide or yellow soda ash after the catholyte filtration and get aminopropanol through underpressure distillation.
In concrete the enforcement, catholyte consists of by mass ratio: alanine 15～35, water 80～60, sulfuric acid and vitriol 4～4.5, catalyzer 1～0.5.
The catalyzer that adds in catholyte is the loaded article of Re, Ru, Cu, Ni, Pd simple substance or its compound, and carrier is carbon, aluminum oxide or silica gel.
Embodiment 1:
Present embodiment is made electrolyzer with synthetic glass, is divided into cathode compartment and anolyte compartment with cationic exchange membrane, and anode and negative electrode adopt platinized platinum or molybdenum sheet to do electrode, and negative electrode and anodic useful area are 14cm
2, negative electrode and anodic spacing are 1.5cm.
With distilled water preparation 0.5mol/L L-L-Ala solution 100mL, add the 2mL vitriol oil and 2g sodium sulfate, add 0.1g gram palladium-carbon catalyst and get catholyte; Anolyte is 5% sulfuric acid, at current density 250A/m
2Electrolysis is 7 hours under the condition, with the efficient liquid phase chromatographic analysis feed stock conversion is 46.7%, catholyte after filtration, filtrate is neutralized to neutrality, refilters, 77～80 ℃/2.0KPa cut is collected in the filtrate decompression distillation obtained the L-aminopropanol with sodium hydroxide, and productive rate is 41.3%.
Embodiment 2:
Present embodiment electrolyzer and electrolytic solution initial composition are with embodiment 1, catalyzer adopts 0.1 gram ruthenium carbon, constant voltage 14V, electrolysis 9 hours, with the efficient liquid phase chromatographic analysis feed stock conversion is 67.8%, catholyte after filtration, filtrate is neutralized to neutrality, refilters, distills and obtain the L-aminopropanol with yellow soda ash, and productive rate is 64.7%.
Embodiment 3:
Present embodiment initial amino acid DL-alanine, catalyzer are 0.1 gram Raney's nickel, and other are as example 1, control current density 20A/dm
2, electrolysis 12 hours,, be 38.6% with the efficient liquid phase chromatographic analysis feed stock conversion, catholyte after filtration, neutralize, refilter, distill and obtain the DL-aminopropanol, productive rate is 35.4%.
Claims (4)
1. the method for an electrolytic preparation aminopropanol, comprise the amino acid catholyte reduction preparation aminopropanol and two steps of purifying, it is characterized in that adopting ion-exchange membrane that electrolyzer is divided into negative and positive two Room, the concentration of alanine is 0.3～2.0mol/L in the catholyte, and the pH of catholyte is 1～4; Add in described catholyte that catalyzer, described catalyzer are arranged is the loaded article of Re, Ru, Cu, Ni, Pd simple substance or its compound, carrier is carbon, aluminum oxide or silica gel; Described anolyte is that concentration is 2～20% sulfuric acid by mass percentage; The temperature of control electrolytic solution is 30～60 ℃, current density 200～2000A/m
2After reaching electrolytic equilibrium, with catholyte after filtration, neutralize, refilter, distill and promptly get aminopropanol.
2. the method for electrolytic preparation aminopropanol according to claim 1 is characterized in that described catholyte consisting of by mass ratio: alanine 15～35, water 80～60, sulfuric acid and vitriol 4～4.5, catalyzer 1～0.5.
3. the method for electrolytic preparation aminopropanol according to claim 1, the cathode material that it is characterized in that being provided with in the described electrolyzer is platinum, molybdenum, lead or the graphite with katalysis; Anode material is the inert material of acid corrosion-resistant.
4. the method for electrolytic preparation aminopropanol according to claim 4 is characterized in that described anode material is platinum or molybdenum.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101448989A CN101660171B (en) | 2009-09-09 | 2009-09-09 | Method for preparing aminopropanol by electrolysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101448989A CN101660171B (en) | 2009-09-09 | 2009-09-09 | Method for preparing aminopropanol by electrolysis |
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| Publication Number | Publication Date |
|---|---|
| CN101660171A CN101660171A (en) | 2010-03-03 |
| CN101660171B true CN101660171B (en) | 2011-01-05 |
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|---|---|---|---|
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102344378B (en) * | 2010-08-03 | 2013-12-18 | 江苏康恒化工有限公司 | Amino alcohol preparation method using aqueous amino acid |
| CN102229536B (en) * | 2011-04-25 | 2013-11-13 | 上虞市众昌化工有限公司 | Method for separating amino alkyl alcohol through membrane electrodialysis |
| CN102584606B (en) * | 2011-12-28 | 2014-01-29 | 浙江工业大学 | A kind of method utilizing bipolar membrane electrodialysis to prepare amino propanol |
| JP6758628B2 (en) | 2016-11-15 | 2020-09-23 | 国立大学法人横浜国立大学 | Organic hydride manufacturing equipment and organic hydride manufacturing method |
| CN110016684B (en) * | 2019-04-08 | 2021-03-16 | 天津大学 | Method for preparing enamine by electrolyzing amino acid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513132A (en) * | 1947-02-10 | 1950-06-27 | Shell Dev | Preparation of amino alcohols |
| EP0415189A2 (en) * | 1989-08-26 | 1991-03-06 | BASF Aktiengesellschaft | Process for the preparation of aminbenzylalcohol |
| CN1641071A (en) * | 2004-01-18 | 2005-07-20 | 浙江工业大学 | Alkyl hydroxylamine and its salt electrochemical synthesis method |
-
2009
- 2009-09-09 CN CN2009101448989A patent/CN101660171B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513132A (en) * | 1947-02-10 | 1950-06-27 | Shell Dev | Preparation of amino alcohols |
| EP0415189A2 (en) * | 1989-08-26 | 1991-03-06 | BASF Aktiengesellschaft | Process for the preparation of aminbenzylalcohol |
| CN1641071A (en) * | 2004-01-18 | 2005-07-20 | 浙江工业大学 | Alkyl hydroxylamine and its salt electrochemical synthesis method |
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| CN101660171A (en) | 2010-03-03 |
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