CN108976137A - A kind of preparation method of 6- amino -1- hexanol - Google Patents
A kind of preparation method of 6- amino -1- hexanol Download PDFInfo
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- CN108976137A CN108976137A CN201810861985.5A CN201810861985A CN108976137A CN 108976137 A CN108976137 A CN 108976137A CN 201810861985 A CN201810861985 A CN 201810861985A CN 108976137 A CN108976137 A CN 108976137A
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- hexanol
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- 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
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/83—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with rare earths or actinides
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Abstract
The invention discloses a kind of preparation methods of 6- amino -1- hexanol, it is evaporated specifically includes the following steps: nickel powder and dehydrated alcohol are carried out mixed grinding to solvent, is then dispersed in deionized water, sodium ethylene diamine tetracetate is added, it is dispersed with stirring uniformly, dispersion liquid is made；Cerous nitrate is dissolved in deionized water and is uniformly mixed obtained cerous nitrate solution, then it is added drop-wise in dispersion liquid simultaneously with sodium hydroxide solution, is stirred to react, filters after reaction, and drying will be precipitated, catalyst precursor is made；Catalyst precursor is placed in Muffle furnace and handles 1-2h at 800-950 DEG C, after treatment cools to room temperature with the furnace, and the Raney nickel containing cerium is made in grinding；With 1,6- hexylene glycol for raw material, ammonia and hydrogen are then passed to, reacts 1-2h under the catalysis of the Raney nickel obtained above containing cerium, 6- amino -1- hexanol is made.This method is easy to operate, and product yield reaches 93.5% or more.
Description
Technical field:
The present invention relates to medicine intermediate preparation fields, are specifically related to a kind of preparation method of 6- amino -1- hexanol.
Background technique:
6- amino -1- hexanol, is a kind of chemical intermediate, is at room temperature white, needle-shaped crystals, 58-60 DEG C of fusing point, boiling point
130.5-131.5℃(10.2mmHg).It contains amino and hydroxyl, the general character with alkohol and amine, widely used, can be used for preparing
Special chemical article, medicine and pesticide.
Patent (201610114746.4) discloses a kind of using calcium carbonate as the 6- amino -1- hexanol preparation side of catalyst
Method, using calcium carbonate as catalysts, by 1,6- hexylene glycol, ammonia and hydrogen temperature be 270-290 DEG C, pressure 150-180MPa
Under the conditions of Hybrid Heating compressive reaction 1.5-2h.The catalyst that this method uses is cheap, high catalytic efficiency, but reacts item
Part is more harsh.
Summary of the invention:
The object of the present invention is to provide a kind of preparation methods of 6- amino -1- hexanol, and this method mild condition, low energy consumption,
Low for equipment requirements, the cost of material of use is low, and product yield is high.
To achieve the above object, the invention adopts the following technical scheme:
A kind of preparation method of 6- amino -1- hexanol, comprising the following steps:
(1) nickel powder and dehydrated alcohol are carried out mixed grinding to solvent to be evaporated, are then dispersed in deionized water,
Sodium ethylene diamine tetracetate is added, is dispersed with stirring uniformly, dispersion liquid is made；
(2) cerous nitrate is dissolved in deionized water and is uniformly mixed obtained cerous nitrate solution, then by itself and hydroxide
Sodium solution is added drop-wise to simultaneously in dispersion liquid made from step (1), and 0.5-3.5h is stirred to react in the state of 1500-5000 revs/min,
It filters after reaction, and drying will be precipitated, catalyst precursor is made；
(3) catalyst precursor obtained above is placed in Muffle furnace and handles 1-2h, after treatment at 800-950 DEG C
It cools to room temperature with the furnace, grinds, the Raney nickel containing cerium is made；
(4) ammonia and hydrogen are then passed to, in the Raney nickel obtained above containing cerium for raw material with 1,6- hexylene glycol
Catalysis is lower to react 1-2h, and 6- amino -1- hexanol is made.
As a preferred embodiment of the above technical solution, in step (1), the amount ratio of the nickel powder and dehydrated alcohol is 1g:10mL.
As a preferred embodiment of the above technical solution, in step (1), the nickel powder, deionized water, the use of sodium ethylene diamine tetracetate
Amount is than being 1g:(15-20) mL:(0.01-0.05) g.
As a preferred embodiment of the above technical solution, in step (2), the mass concentration of the cerous nitrate solution is 5-15%.
As a preferred embodiment of the above technical solution, in step (2), the mass concentration of the sodium hydroxide solution is 10-20%.
As a preferred embodiment of the above technical solution, in step (2), cerous nitrate, nickel mass ratio be 0.3:(2-6).
As a preferred embodiment of the above technical solution, in step (4), the temperature of the reaction is 200-220 DEG C, the reaction
Pressure is 4-5MPa.
As a preferred embodiment of the above technical solution, in step (4), 6- amino -1- hexanol, catalyst mass ratio be 2:
(0.015-0.03)。
The invention has the following advantages:
The present invention is that raw material prepares 6- amino -1- hexanol, the catalyst of use using one-step method with 1,6- hexylene glycol
Activity is good, and the conversion ratio of 1,6- hexylene glycol is that the yield of 100%, 6- amino -1- hexanol is 93.5% or more；
The present invention, first by nickel powder and ethyl alcohol mixed grinding, effectively refines nickel powder partial size during preparing catalyst,
The surface-active of nickel powder is improved, then stable dispersion is in deionized water under the action of sodium ethylene diamine tetracetate；Then same
When cerous nitrate solution and sodium hydroxide solution co-precipitation is added dropwise, be finally heat-treated again, catalyst activity obtained is high,
High temperature resistant can effectively reduce reaction temperature, pressure, shorten the reaction time, improve product yield.
Specific embodiment:
In order to better understand the present invention, below by embodiment, the present invention is further described, and embodiment is served only for solving
The present invention is released, any restriction will not be constituted to the present invention.
Embodiment 1
A kind of preparation method of 6- amino -1- hexanol, comprising the following steps:
(1) nickel powder and dehydrated alcohol are carried out mixed grinding to solvent to be evaporated, are then dispersed in deionized water,
Sodium ethylene diamine tetracetate is added, is dispersed with stirring uniformly, dispersion liquid is made；Wherein, nickel powder, deionized water, sodium ethylene diamine tetracetate
Amount ratio be 1g:15mL:0.01g；
(2) cerous nitrate is dissolved in and is uniformly mixed the cerous nitrate solution that obtained mass concentration is 5% in deionized water, so
Afterwards it is added drop-wise in dispersion liquid made from step (1) simultaneously with sodium hydroxide solution, is stirred to react in the state of 1500 revs/min
0.5h is filtered after reaction, and will precipitate drying, and catalyst precursor is made；Wherein, cerous nitrate, nickel mass ratio be
0.3:2；
(3) catalyst precursor obtained above is placed in Muffle furnace and handles 1h at 800 DEG C, after treatment is cold with furnace
But to room temperature, the Raney nickel containing cerium is made in grinding；
(4) ammonia and hydrogen are then passed to, in the Raney nickel obtained above containing cerium for raw material with 1,6- hexylene glycol
Catalysis is lower to react 1h, and 6- amino -1- hexanol is made；The temperature of the reaction is 200 DEG C, and the pressure of the reaction is 4-5MPa；
6- amino -1- hexanol, catalyst mass ratio be 2:0.015.
Embodiment 2
A kind of preparation method of 6- amino -1- hexanol, comprising the following steps:
(1) nickel powder and dehydrated alcohol are carried out mixed grinding to solvent to be evaporated, are then dispersed in deionized water,
Sodium ethylene diamine tetracetate is added, is dispersed with stirring uniformly, dispersion liquid is made；Wherein, nickel powder, deionized water, sodium ethylene diamine tetracetate
Amount ratio be 1g:20mL:0.05g；
(2) cerous nitrate is dissolved in be uniformly mixed in deionized water obtained mass concentration be 5-15% cerous nitrate it is molten
Then it is added drop-wise in dispersion liquid made from step (1) simultaneously with sodium hydroxide solution, stirs in the state of 5000 revs/min by liquid
Reaction 3.5h is mixed, is filtered after reaction, and drying will be precipitated, catalyst precursor is made；Wherein, the quality of cerous nitrate, nickel
Than for 0.3:6；
(3) catalyst precursor obtained above is placed in Muffle furnace and handles 2h at 950 DEG C, after treatment is cold with furnace
But to room temperature, the Raney nickel containing cerium is made in grinding；
(4) ammonia and hydrogen are then passed to, in the Raney nickel obtained above containing cerium for raw material with 1,6- hexylene glycol
Catalysis is lower to react 2h, and 6- amino -1- hexanol is made；The temperature of the reaction is 220 DEG C, and the pressure of the reaction is 4-5MPa；
6- amino -1- hexanol, catalyst mass ratio be 2:0.03.
Embodiment 3
A kind of preparation method of 6- amino -1- hexanol, comprising the following steps:
(1) nickel powder and dehydrated alcohol are carried out mixed grinding to solvent to be evaporated, are then dispersed in deionized water,
Sodium ethylene diamine tetracetate is added, is dispersed with stirring uniformly, dispersion liquid is made；Wherein, nickel powder, deionized water, sodium ethylene diamine tetracetate
Amount ratio be 1g:15mL:0.02g；
(2) cerous nitrate is dissolved in and is uniformly mixed the cerous nitrate solution that obtained mass concentration is 10% in deionized water,
Then it is added drop-wise in dispersion liquid made from step (1) simultaneously with sodium hydroxide solution, is stirred in the state of 2000 revs/min anti-
1h is answered, is filtered after reaction, and drying will be precipitated, catalyst precursor is made；Wherein, cerous nitrate, nickel mass ratio be
0.3:3；
(3) catalyst precursor obtained above is placed in Muffle furnace at 850 DEG C and handles 1.2h, after treatment is with furnace
It is cooled to room temperature, grinds, the Raney nickel containing cerium is made；
(4) ammonia and hydrogen are then passed to, in the Raney nickel obtained above containing cerium for raw material with 1,6- hexylene glycol
Catalysis is lower to react 1.2h, and 6- amino -1- hexanol is made；The temperature of the reaction is 205 DEG C, and the pressure of the reaction is 4-
5MPa；6- amino -1- hexanol, catalyst mass ratio be 2:0.02.
Embodiment 4
A kind of preparation method of 6- amino -1- hexanol, comprising the following steps:
(1) nickel powder and dehydrated alcohol are carried out mixed grinding to solvent to be evaporated, are then dispersed in deionized water,
Sodium ethylene diamine tetracetate is added, is dispersed with stirring uniformly, dispersion liquid is made；Wherein, nickel powder, deionized water, sodium ethylene diamine tetracetate
Amount ratio be 1g:20mL:0.03g；
(2) cerous nitrate is dissolved in and is uniformly mixed the cerous nitrate solution that obtained mass concentration is 10% in deionized water,
Then it is added drop-wise in dispersion liquid made from step (1) simultaneously with sodium hydroxide solution, is stirred in the state of 3000 revs/min anti-
1.5h is answered, is filtered after reaction, and drying will be precipitated, catalyst precursor is made；Wherein, cerous nitrate, nickel mass ratio be
0.3:4；
(3) catalyst precursor obtained above is placed in Muffle furnace at 850 DEG C and handles 1.4h, after treatment is with furnace
It is cooled to room temperature, grinds, the Raney nickel containing cerium is made；
(4) ammonia and hydrogen are then passed to, in the Raney nickel obtained above containing cerium for raw material with 1,6- hexylene glycol
Catalysis is lower to react 1.4h, and 6- amino -1- hexanol is made；The temperature of the reaction is 210 DEG C, and the pressure of the reaction is 4-
5MPa；6- amino -1- hexanol, catalyst mass ratio be 2:0.02.
Embodiment 5
A kind of preparation method of 6- amino -1- hexanol, comprising the following steps:
(1) nickel powder and dehydrated alcohol are carried out mixed grinding to solvent to be evaporated, are then dispersed in deionized water,
Sodium ethylene diamine tetracetate is added, is dispersed with stirring uniformly, dispersion liquid is made；Wherein, nickel powder, deionized water, sodium ethylene diamine tetracetate
Amount ratio be 1g:20mL:0.03g；
(2) cerous nitrate is dissolved in and is uniformly mixed the cerous nitrate solution that obtained mass concentration is 9% in deionized water, so
Afterwards it is added drop-wise in dispersion liquid made from step (1) simultaneously with sodium hydroxide solution, is stirred to react in the state of 4000 revs/min
2h is filtered after reaction, and will precipitate drying, and catalyst precursor is made；Wherein, cerous nitrate, nickel mass ratio be 0.3:
5；
(3) catalyst precursor obtained above is placed in Muffle furnace and handles 1.6h, after treatment at 800-950 DEG C
It cools to room temperature with the furnace, grinds, the Raney nickel containing cerium is made；
(4) ammonia and hydrogen are then passed to, in the Raney nickel obtained above containing cerium for raw material with 1,6- hexylene glycol
Catalysis is lower to react 1.6h, and 6- amino -1- hexanol is made；The temperature of the reaction is 210 DEG C, and the pressure of the reaction is 4-
5MPa；6- amino -1- hexanol, catalyst mass ratio be 2:0.02.
Embodiment 6
A kind of preparation method of 6- amino -1- hexanol, comprising the following steps:
(1) nickel powder and dehydrated alcohol are carried out mixed grinding to solvent to be evaporated, are then dispersed in deionized water,
Sodium ethylene diamine tetracetate is added, is dispersed with stirring uniformly, dispersion liquid is made；Wherein, nickel powder, deionized water, sodium ethylene diamine tetracetate
Amount ratio be 1g:15mL:0.04g；
(2) cerous nitrate is dissolved in and is uniformly mixed the cerous nitrate solution that obtained mass concentration is 12% in deionized water,
Then it is added drop-wise in dispersion liquid made from step (1) simultaneously with sodium hydroxide solution, is stirred in the state of 4500 revs/min anti-
3h is answered, is filtered after reaction, and drying will be precipitated, catalyst precursor is made；Wherein, cerous nitrate, nickel mass ratio be
0.3:5.5；
(3) catalyst precursor obtained above is placed in Muffle furnace at 900 DEG C and handles 1.8h, after treatment is with furnace
It is cooled to room temperature, grinds, the Raney nickel containing cerium is made；
(4) ammonia and hydrogen are then passed to, in the Raney nickel obtained above containing cerium for raw material with 1,6- hexylene glycol
Catalysis is lower to react 1.8h, and 6- amino -1- hexanol is made；The temperature of the reaction is 210 DEG C, and the pressure of the reaction is 4-
5MPa；6- amino -1- hexanol, catalyst mass ratio be 2:0.025.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (8)
1. a kind of preparation method of 6- amino -1- hexanol, which comprises the following steps:
(1) nickel powder and dehydrated alcohol are carried out mixed grinding to solvent to be evaporated, is then dispersed in deionized water, is added
Sodium ethylene diamine tetracetate is dispersed with stirring uniformly, dispersion liquid is made；
(2) cerous nitrate is dissolved in deionized water and is uniformly mixed obtained cerous nitrate solution, it is then that it is molten with sodium hydroxide
Liquid is added drop-wise to simultaneously in dispersion liquid made from step (1), and 0.5-3.5h is stirred to react in the state of 1500-5000 revs/min, reaction
After filter, and drying will be precipitated, catalyst precursor is made；
(3) catalyst precursor obtained above is placed in Muffle furnace at 800-950 DEG C and handles 1-2h, after treatment is with furnace
It is cooled to room temperature, grinds, the Raney nickel containing cerium is made；
(4) ammonia and hydrogen are then passed to, in the catalysis of the Raney nickel obtained above containing cerium for raw material with 1,6- hexylene glycol
6- amino -1- hexanol is made in lower reaction 1-2h.
2. a kind of preparation method of 6- amino -1- hexanol as described in claim 1, which is characterized in that described in step (1)
The amount ratio of nickel powder and dehydrated alcohol is 1g:10mL.
3. a kind of preparation method of 6- amino -1- hexanol as described in claim 1, which is characterized in that described in step (1)
Nickel powder, deionized water, sodium ethylene diamine tetracetate amount ratio be 1g:(15-20) mL:(0.01-0.05) g.
4. a kind of preparation method of 6- amino -1- hexanol as described in claim 1, which is characterized in that described in step (2)
The mass concentration of cerous nitrate solution is 5-15%.
5. a kind of preparation method of 6- amino -1- hexanol as described in claim 1, which is characterized in that described in step (2)
The mass concentration of sodium hydroxide solution is 10-20%.
6. a kind of preparation method of 6- amino -1- hexanol as described in claim 1, which is characterized in that in step (2), nitric acid
Cerium, nickel mass ratio be 0.3:(2-6).
7. a kind of preparation method of 6- amino -1- hexanol as described in claim 1, which is characterized in that described in step (4)
The temperature of reaction is 200-220 DEG C, and the pressure of the reaction is 4-5MPa.
8. a kind of preparation method of 6- amino -1- hexanol as described in claim 1, which is characterized in that in step (4), 6- ammonia
Base -1- hexanol, catalyst mass ratio be 2:(0.015-0.03).
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| CN201810861985.5A CN108976137A (en) | 2018-08-01 | 2018-08-01 | A kind of preparation method of 6- amino -1- hexanol |
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| CN201810861985.5A CN108976137A (en) | 2018-08-01 | 2018-08-01 | A kind of preparation method of 6- amino -1- hexanol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110330438A (en) * | 2019-07-04 | 2019-10-15 | 苏州华道生物药业股份有限公司 | A kind of synthetic method of 6- amino -1- hexanol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01242559A (en) * | 1988-03-23 | 1989-09-27 | Japan Synthetic Rubber Co Ltd | Production of amino alcohol |
| CN106810459A (en) * | 2015-11-30 | 2017-06-09 | 中国科学院大连化学物理研究所 | A kind of method that amino alcohol is prepared as raw material with dihydroxylic alcohols and/or polyalcohol |
-
2018
- 2018-08-01 CN CN201810861985.5A patent/CN108976137A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01242559A (en) * | 1988-03-23 | 1989-09-27 | Japan Synthetic Rubber Co Ltd | Production of amino alcohol |
| CN106810459A (en) * | 2015-11-30 | 2017-06-09 | 中国科学院大连化学物理研究所 | A kind of method that amino alcohol is prepared as raw material with dihydroxylic alcohols and/or polyalcohol |
Non-Patent Citations (2)
| Title |
|---|
| 任夫健 等: "6-氨基-1-己醇的合成方法", 《化工生产与技术》 * |
| 任夫健: "6-氨基-1-己醇合成工艺进展", 《精细与专用化学品》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110330438A (en) * | 2019-07-04 | 2019-10-15 | 苏州华道生物药业股份有限公司 | A kind of synthetic method of 6- amino -1- hexanol |
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