CN111686762A - Green synthesis method of amino alcohol compound under catalysis of visible light - Google Patents
Green synthesis method of amino alcohol compound under catalysis of visible light Download PDFInfo
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- CN111686762A CN111686762A CN202010524504.9A CN202010524504A CN111686762A CN 111686762 A CN111686762 A CN 111686762A CN 202010524504 A CN202010524504 A CN 202010524504A CN 111686762 A CN111686762 A CN 111686762A
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- amino alcohol
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- aqueous solution
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- -1 amino alcohol compound Chemical class 0.000 title claims abstract description 32
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 21
- 238000001308 synthesis method Methods 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 239000007864 aqueous solution Substances 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 18
- 238000001816 cooling Methods 0.000 claims abstract description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims abstract description 14
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052980 cadmium sulfide Inorganic materials 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 9
- 239000011941 photocatalyst Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001413 amino acids Chemical class 0.000 claims abstract description 7
- 229910052786 argon Inorganic materials 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 7
- 238000013375 chromatographic separation Methods 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 238000007789 sealing Methods 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 12
- 239000002159 nanocrystal Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 229940024606 amino acid Drugs 0.000 claims description 6
- 235000001014 amino acid Nutrition 0.000 claims description 6
- 150000001414 amino alcohols Chemical class 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 238000011068 loading method Methods 0.000 claims description 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 4
- 238000007599 discharging Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 229910021555 Chromium Chloride Inorganic materials 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 claims description 2
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 claims description 2
- 229930195711 D-Serine Natural products 0.000 claims description 2
- 229930182847 D-glutamic acid Natural products 0.000 claims description 2
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 claims description 2
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims description 2
- 229930182832 D-phenylalanine Natural products 0.000 claims description 2
- 229930182820 D-proline Natural products 0.000 claims description 2
- KZSNJWFQEVHDMF-SCSAIBSYSA-N D-valine Chemical compound CC(C)[C@@H](N)C(O)=O KZSNJWFQEVHDMF-SCSAIBSYSA-N 0.000 claims description 2
- 229930182831 D-valine Natural products 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-Glutamic acid Natural products OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- 229930182821 L-proline Natural products 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 229960003767 alanine Drugs 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 229960002989 glutamic acid Drugs 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 229960002429 proline Drugs 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 229960001153 serine Drugs 0.000 claims description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 229960004295 valine Drugs 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 241000190633 Cordyceps Species 0.000 description 1
- ZZIKIHCNFWXKDY-UHFFFAOYSA-N Myriocin Natural products CCCCCCC(=O)CCCCCCC=CCC(O)C(O)C(N)(CO)C(O)=O ZZIKIHCNFWXKDY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- ZZIKIHCNFWXKDY-GNTQXERDSA-N myriocin Chemical compound CCCCCCC(=O)CCCCCC\C=C\C[C@@H](O)[C@H](O)[C@@](N)(CO)C(O)=O ZZIKIHCNFWXKDY-GNTQXERDSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/04—Sulfides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/39—Photocatalytic properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G11/00—Compounds of cadmium
- C01G11/02—Sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- Chemical Kinetics & Catalysis (AREA)
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- Manufacturing & Machinery (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the technical field of compound preparation, and discloses a green synthesis method of amino alcohol compounds under visible light catalysis, which comprises the steps of sequentially adding amino acid, photocatalyst and inorganic acid aqueous solution into a reaction kettle; introducing argon into the reaction kettle; sealing the reaction kettle, introducing hydrogen into the reaction kettle, and heating to 120-130 ℃; after reacting for 30 minutes, cooling and continuing to react for 30 minutes; cooling, and cooling at room temperature; adding a solvent into the reaction product, stirring for 20 minutes, carrying out chromatographic separation, and purifying the separated product to obtain the amino alcohol compound. The synthesis route provided by the invention is simple, the raw materials are easy to obtain, the cost is low, the operation is simple and convenient, the reaction process is mild and controllable, and meanwhile, the byproducts are few and the yield is high; meanwhile, the invention utilizes cadmium sulfide nanocrystalline as photocatalyst to improve the efficiency of the whole reaction and effectively improve the activity of amino alcohol compounds.
Description
Technical Field
The invention belongs to the technical field of compound preparation, and particularly relates to a green synthesis method of an amino alcohol compound under the catalysis of visible light.
Background
At present: amino alcohol compounds of the formula: among them, the β -aminoalcohol compound, which contains both amino and alcohol groups, exhibits dual chemical reactivity of amine and alcohol, and thus is widely used in various fields of production and life, such as: the product can be used as high molecular material catalyst, pigment dispersant, industrial fluid emulsifier, formaldehyde fixing agent, organic synthetic reagent (especially for synthesizing small molecular drugs), etc. In addition, the structure of amino alcohols is also widely found in many bioactive natural products, such as anti-aids drugs, anti-hypertensive drugs, cordyceps myriocin, marine natural products that resist multidrug resistance, and the like. The synthesis of amino alcohols is therefore of great interest to chemists.
The existing synthesis method of amino alcohol compounds is mainly used for preparing the amino alcohol compounds by a method of catalyzing by a chemical catalyst and then reducing, however, the amino alcohol compounds prepared by the existing preparation method are low in yield, complex in preparation method, high in cost and more in byproducts.
Through the above analysis, the problems and defects of the prior art are as follows: the amino alcohol compound prepared by the existing preparation method has low yield, and meanwhile, the preparation method is complex, high in cost and more in byproducts.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a green synthesis method of amino alcohol compounds under the catalysis of visible light.
The invention is realized in such a way that the green synthesis method of the amino alcohol compound under the catalysis of visible light comprises the following steps:
step one, sequentially adding amino acid, photocatalyst and inorganic acid aqueous solution into a reaction kettle, and uniformly stirring to obtain a mixed solution;
step two, closing the reaction kettle, introducing argon into the reaction kettle for 30 minutes, and completely discharging the original air in the reaction kettle;
step three, sealing the reaction kettle, introducing hydrogen into the reaction kettle, and heating to 120-130 ℃;
step four, after reacting for 30 minutes, cooling to 100-120 ℃, and continuing to react for 30 minutes; then cooling, and cooling at room temperature;
and step five, adding a solvent into the reactant, stirring for 20 minutes, carrying out chromatographic separation, and purifying the separated substance to obtain the amino alcohol compound.
Further, in the first step, the amino acid is any one of L-alanine, L-proline, L-glutamic acid, L-phenylalanine, L-lysine, L-serine, L-valine, D-alanine, D-proline, D-glutamic acid, D-phenylalanine, D-lysine, D-serine and D-valine.
Further, in the step one, the photocatalyst is cadmium sulfide nanocrystal.
Further, the preparation method of the cadmium sulfide nanocrystal comprises the following steps:
(1) adding 10mmol of chromium chloride into 50mL of water, and magnetically stirring;
(2) after stirring evenly, adding 6mmol of thioglycollic acid, and adjusting the pH value of the solution to 6-7;
(3) slowly adding 3mmol of sodium sulfate aqueous solution into the solution, and stirring until the solution is transparent;
(4) and adding absolute ethyl alcohol into the solution, separating out a precipitate, washing and drying to obtain the cadmium sulfide nanocrystal.
Further, in the first step, the inorganic acid aqueous solution is any one of a silicic acid aqueous solution, a boric acid aqueous solution, a hydrocyanic acid aqueous solution, a hydrofluoric acid aqueous solution, a nitrous acid aqueous solution, a perhalogenic acid aqueous solution, and a meta-aluminate aqueous solution.
Further, in the first step, the concentration of the inorganic acid aqueous solution is 2.0-3.0 mol/L.
Further, in the second step, the purity of the argon gas is 99.99%.
Further, in the third step, the pressure of the hydrogen is 6-12 MPa.
Further, in the fifth step, the solvent is any one of acetonitrile, N-dimethylformamide and acetone.
Further, in the fifth step, the purifying the isolate specifically comprises:
(1) loading silica gel and petroleum ether of 100-200 meshes into a column, loading the column, and dissolving the separated substance in dichloromethane to be loaded at the upper end part of the silica gel column;
(2) eluting with mixed solvent of petroleum ether and ethyl acetate, and concentrating the organic phase under reduced pressure to remove solvent;
(3) vacuum drying to obtain pure amino alcohol compound.
Further, the green synthesis method of the amino alcohol compound under the catalysis of visible light further comprises the following steps:
extracting gas in the reaction bottle by using a sample injection needle and injecting the gas into a gas chromatograph to detect the type and content of the gas; when no carbonyl compound is present in the gas, the reaction is complete.
By combining all the technical schemes, the invention has the advantages and positive effects that: the synthesis method provided by the invention has the advantages of simple technical route, simple and easily obtained raw materials, low cost, simple and convenient operation, no high-temperature reaction condition, mild and controllable reaction process, few byproducts and high yield. Meanwhile, the cadmium sulfide nanocrystal is used as the photocatalyst, so that the overall reaction efficiency can be improved, and the activity of the amino alcohol compound can be effectively improved.
Drawings
FIG. 1 is a flow chart of a green synthesis method of amino alcohol compounds under visible light catalysis provided by the embodiment of the invention.
Fig. 2 is a flowchart of a method for preparing cadmium sulfide nanocrystals provided in an embodiment of the present invention.
FIG. 3 is a flow chart of the purification of an isolate provided by an embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Aiming at the problems in the prior art, the invention provides a green synthesis method of amino alcohol compounds under the catalysis of visible light, and the invention is described in detail with reference to the accompanying drawings.
As shown in fig. 1, the green synthesis method of aminoalcohol compounds under visible light catalysis provided by the embodiment of the present invention includes the following steps:
s101, sequentially adding amino acid, a photocatalyst and an inorganic acid aqueous solution into a reaction kettle, and uniformly stirring to obtain a mixed solution;
s102, closing the reaction kettle, introducing argon into the reaction kettle for 30 minutes, and completely discharging the original air in the reaction kettle;
s103, sealing the reaction kettle, introducing hydrogen into the reaction kettle, and heating to 120-130 ℃;
s104, cooling to 100-120 ℃ after reacting for 30 minutes, and continuing to react for 30 minutes; then cooling, and cooling at room temperature;
and S105, adding a solvent into the reaction product, stirring for 20 minutes, carrying out chromatographic separation, and purifying the separated product to obtain the amino alcohol compound.
As shown in fig. 2, the preparation method of the cadmium sulfide nanocrystal provided by the embodiment of the present invention includes:
s201, adding 10mmol of chromium chloride into 50mL of water, and magnetically stirring;
s202, adding 6mmol of thioglycollic acid after uniformly stirring, and adjusting the pH value of the solution to 6-7;
s203, slowly adding 3mmol of sodium sulfate aqueous solution into the solution, and stirring until the solution is transparent;
and S204, adding absolute ethyl alcohol into the solution, separating out the precipitate, washing and drying to obtain the cadmium sulfide nanocrystal.
As shown in fig. 3, the purification of the separated substance provided by the embodiment of the present invention specifically includes:
s301, filling a column with 100-200 mesh silica gel and petroleum ether, loading the column, and dissolving the separated substance in dichloromethane, wherein the upper end part of the silica gel column is filled with the dissolved substance;
s302, eluting with a mixed solvent of petroleum ether and ethyl acetate, and concentrating the organic phase under reduced pressure to remove the solvent;
s303, drying in vacuum to obtain the pure amino alcohol compound.
The method comprises the following steps of sequentially adding amino acid, photocatalyst and inorganic acid aqueous solution into a reaction kettle, and uniformly stirring to obtain a mixed solution; closing the reaction kettle, introducing argon into the reaction kettle for 30 minutes, and completely discharging the original air in the reaction kettle; sealing the reaction kettle, introducing hydrogen into the reaction kettle, and heating to 120-130 ℃; after reacting for 30 minutes, cooling to 100-120 ℃, and continuing to react for 30 minutes; then cooling, and cooling at room temperature; adding a solvent into the reaction product, stirring for 20 minutes, carrying out chromatographic separation, and purifying the separated product to obtain the amino alcohol compound.
The above description is only for the purpose of illustrating the present invention and the appended claims are not to be construed as limiting the scope of the invention, which is intended to cover all modifications, equivalents and improvements that are within the spirit and scope of the invention as defined by the appended claims.
Claims (10)
1. A green synthesis method of amino alcohol compounds under visible light catalysis is characterized by comprising the following steps:
step one, sequentially adding amino acid, photocatalyst and inorganic acid aqueous solution into a reaction kettle, and uniformly stirring to obtain a mixed solution;
step two, closing the reaction kettle, introducing argon into the reaction kettle for 30 minutes, and completely discharging the original air in the reaction kettle;
step three, sealing the reaction kettle, introducing hydrogen into the reaction kettle, and heating to 120-130 ℃;
step four, after reacting for 30 minutes, cooling to 100-120 ℃, and continuing to react for 30 minutes; then cooling, and cooling at room temperature;
and step five, adding a solvent into the reactant, stirring for 20 minutes, carrying out chromatographic separation, and purifying the separated substance to obtain the amino alcohol compound.
2. The method for green synthesis of aminoalcohol compounds under visible light catalysis as claimed in claim 1, wherein in step one, the amino acid is any one of L-alanine, L-proline, L-glutamic acid, L-phenylalanine, L-lysine, L-serine, L-valine, D-alanine, D-proline, D-glutamic acid, D-phenylalanine, D-lysine, D-serine, and D-valine.
3. The green synthesis method of amino alcohol compounds under visible light catalysis as claimed in claim 1, wherein in step one, the photocatalyst is cadmium sulfide nanocrystal.
4. The green synthesis method of amino alcohol compounds under the catalysis of visible light according to claim 3, wherein the preparation method of the cadmium sulfide nanocrystal comprises the following steps:
(1) adding 10mmol of chromium chloride into 50mL of water, and magnetically stirring;
(2) after stirring evenly, adding 6mmol of thioglycollic acid, and adjusting the pH value of the solution to 6-7;
(3) slowly adding 3mmol of sodium sulfate aqueous solution into the solution, and stirring until the solution is transparent;
(4) and adding absolute ethyl alcohol into the solution, separating out a precipitate, washing and drying to obtain the cadmium sulfide nanocrystal.
5. The method for green synthesis of aminoalcohol compounds under visible light catalysis as claimed in claim 1, wherein in the first step, the inorganic acid aqueous solution is any one of silicic acid aqueous solution, boric acid aqueous solution, hydrocyanic acid aqueous solution, hydrofluoric acid aqueous solution, nitrous acid aqueous solution, perhalogenate aqueous solution, and metaaluminate aqueous solution.
6. The method for green synthesis of aminoalcohol compounds under visible light catalysis as claimed in claim 1, wherein in step one, the concentration of the aqueous solution of inorganic acid is 2.0-3.0 mol/L.
7. The green synthesis method of amino alcohol compounds under visible light catalysis as claimed in claim 1, wherein in step two, the purity of argon gas is 99.99%.
8. The green synthesis method of amino alcohol compounds under visible light catalysis as claimed in claim 1, wherein in step three, the pressure of hydrogen is 6-12 MPa;
in the fifth step, the solvent is any one of acetonitrile, N-dimethylformamide and acetone.
9. The green synthesis method of amino alcohol compounds under visible light catalysis as claimed in claim 1, wherein in step five, the purification of the isolate specifically comprises:
(1) loading silica gel and petroleum ether of 100-200 meshes into a column, loading the column, and dissolving the separated substance in dichloromethane to be loaded at the upper end part of the silica gel column;
(2) eluting with mixed solvent of petroleum ether and ethyl acetate, and concentrating the organic phase under reduced pressure to remove solvent;
(3) vacuum drying to obtain pure amino alcohol compound.
10. The method for green synthesis of amino alcohol compounds under visible light catalysis according to claim 1, wherein the method for green synthesis of amino alcohol compounds under visible light catalysis further comprises:
extracting gas in the reaction bottle by using a sample injection needle and injecting the gas into a gas chromatograph to detect the type and content of the gas; when no carbonyl compound is present in the gas, the reaction is complete.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000019205A (en) * | 1998-09-09 | 2000-04-06 | 김충섭 | Method for producing hydrogen using cadmium sulfide grouped photo catalyst for generating hydrogen |
| 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 |
| CN110550992A (en) * | 2019-09-20 | 2019-12-10 | 杭州师范大学 | green synthesis method of amino alcohol compound under catalysis of visible light |
| CN110605137A (en) * | 2019-09-20 | 2019-12-24 | 湖北大学 | Preparation method of CdS-based composite photocatalyst and application of CdS-based composite photocatalyst in aspect of hydrogen production through water splitting |
| CN110665516A (en) * | 2019-09-23 | 2020-01-10 | 常州大学 | Preparation method of composite cadmium sulfide photocatalyst |
-
2020
- 2020-06-10 CN CN202010524504.9A patent/CN111686762A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000019205A (en) * | 1998-09-09 | 2000-04-06 | 김충섭 | Method for producing hydrogen using cadmium sulfide grouped photo catalyst for generating hydrogen |
| 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 |
| CN110550992A (en) * | 2019-09-20 | 2019-12-10 | 杭州师范大学 | green synthesis method of amino alcohol compound under catalysis of visible light |
| CN110605137A (en) * | 2019-09-20 | 2019-12-24 | 湖北大学 | Preparation method of CdS-based composite photocatalyst and application of CdS-based composite photocatalyst in aspect of hydrogen production through water splitting |
| CN110665516A (en) * | 2019-09-23 | 2020-01-10 | 常州大学 | Preparation method of composite cadmium sulfide photocatalyst |
Non-Patent Citations (2)
| Title |
|---|
| 唐一文等: "《近代物理实验教程》", 30 July 2015, 华中师范大学出版 * |
| 武英峰: "可控形貌CdS的制备及光催化性能的研究", 《中国优秀硕士学位论文全文数据库》 * |
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