CN111747925A - Nicotine purification method - Google Patents
Nicotine purification method Download PDFInfo
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- CN111747925A CN111747925A CN202010614621.4A CN202010614621A CN111747925A CN 111747925 A CN111747925 A CN 111747925A CN 202010614621 A CN202010614621 A CN 202010614621A CN 111747925 A CN111747925 A CN 111747925A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Abstract
The invention provides a nicotine purification method, which comprises the following steps: putting nicotine to be treated into a short-range molecular distiller, rectifying under the conditions of temperature of 20-60 ℃ and pressure of 10-20mbar, taking heavy components, putting the heavy components into the short-range molecular distiller again, rectifying under the conditions of temperature of 40-80 ℃ and pressure of 0.01-1mbar, taking light components, dissolving the light components into a mobile phase, introducing the light components into a high-speed counter-current chromatograph with established stationary phase-mobile phase dynamic balance through a sample introduction valve, collecting nicotine solution by utilizing an ultraviolet detector spectrum or a high performance liquid chromatography, and concentrating the nicotine solution to obtain high-purity nicotine.
Description
Technical Field
The invention relates to the technical field of purification of natural products, in particular to a nicotine purification method.
Background
Nicotine, also called nicotine, is an important pharmaceutical and chemical raw material, which is mainly extracted from tobacco leaves or tobacco stems, wherein in the current industrial production, alkali liquor is adopted to extract free nicotine from tobacco raw materials, and then the free nicotine is extracted by an organic solvent, and then the free nicotine is extracted by an acid liquor and an organic solvent to obtain nicotine with relatively high purity, because the boiling point difference of the nicotine and the conventional organic solvent is large, partial impurities with high boiling points, such as dehydroneonicotine, meslamine, cotinine, L (-) -octagon and the like, can exist in the nicotine obtained by rectification and extraction of the organic solvent, wherein the partial impurities, such as mestamine and cotinine, are quite close to the boiling point of the nicotine, the impurities are difficult to separate by the way of separation of the boiling point difference, although different products can be effectively separated by the way of adsorption separation of resin, a large amount of solvent and time can still be consumed for cleaning and reducing the resin after separation, thereby reducing the efficiency of the purification of the whole nicotine and easily generating a waste solvent.
Therefore, how to provide a nicotine purification method which has an industrial application prospect, can effectively purify nicotine and is not easy to generate three wastes is called a technical problem which needs to be solved urgently in the field.
Disclosure of Invention
In view of the above, the present invention provides a purification method of nicotine, which can effectively separate nicotine with similar boiling points and less waste solvent.
The technical scheme of the invention is realized as follows: the invention provides a nicotine purification method, which comprises the following steps:
step one, putting nicotine to be treated into a short-range molecular distiller, and rectifying at the temperature of 20-60 ℃ and under the pressure of 10-20mbar to obtain heavy components;
step two, putting the heavy component obtained in the step one into a short-distance molecular distiller again, rectifying the heavy component at the temperature of 40-80 ℃ and under the pressure of 0.01-1mbar, and taking a light component;
dissolving the light component obtained in the step two in a mobile phase, feeding the light component into a high-speed counter-current chromatograph with established stationary phase-mobile phase dynamic balance through a sample injection valve, and collecting nicotine solution by utilizing an ultraviolet detector spectrum or a high performance liquid chromatography;
and step four, concentrating the nicotine solution obtained in the step three to obtain high-purity nicotine.
On the basis of the technical scheme, preferably, in the step one, the temperature is 40-60 ℃, and the pressure is 10-15 mbar.
On the basis of the technical scheme, preferably, in the second step, the temperature is 60-80 ℃, and the pressure is 0.01-0.05 mbar.
On the basis of the above technical solution, preferably, in step three, the method for establishing the stationary phase-mobile phase dynamic equilibrium by the high-speed countercurrent chromatograph includes:
step one, respectively preparing a stationary phase solvent system and a mobile phase solvent system;
filling the high-speed counter-current chromatograph with the stationary phase, setting the temperature of the constant-temperature circulator, adjusting the rotating speed of a host of the high-speed counter-current chromatograph, finally pumping the mobile phase, detecting by using an ultraviolet detector, and when the mobile phase flows out obviously, establishing the stationary phase-mobile phase dynamic balance by the high-speed counter-current chromatograph.
More preferably, the preparation method of the stationary phase solvent system and the mobile phase solvent system comprises the steps of mixing and stirring petroleum ether, ethyl acetate, methanol and water uniformly, standing for layering, taking the upper layer as the stationary phase, and taking the lower layer as the mobile phase.
On the basis of the above technical solution, preferably, the petroleum ether: ethyl acetate: methanol: the volume ratio of water is (3-5): (3-5): (4-7): (3-6).
On the basis of the above technical solution, preferably, the petroleum ether: ethyl acetate: methanol: the volume ratio of water is (3-4): (3-4): (5-6): (5-6).
On the basis of the above technical solution, preferably, in the second step, the temperature of the constant temperature circulator is 20 to 30 ℃.
On the basis of the above technical solution, preferably, in the step two, the rotation speed of the host of the high-speed countercurrent chromatograph is 800-.
On the basis of the technical scheme, the pumping speed of the mobile phase is preferably 0.5-5 ml/min.
Compared with the prior art, the nicotine purification method has the following beneficial effects:
(1) the method utilizes the short-path molecular distiller to carry out rectification twice on the nicotine crude product, respectively removes low-boiling impurities and high-boiling impurities, reduces the types of the impurities in the nicotine crude product, and then utilizes the high-speed counter-current chromatograph to carry out impurity separation, does not need the high-temperature process of conventional rectification, does not need a large amount of cost brought by adsorption of a resin tower and the cleaning treatment flow of the resin tower, has high production efficiency, can produce more pure nicotine as far as possible, and has good application prospect;
(2) the whole purification method has simple steps, the distillation efficiency of the short-range molecular distiller is high, nicotine can be prevented from being at a higher temperature, more impurities are avoided, and after primary impurity separation, the nicotine is purified by using a more accurate high-speed counter-current chromatograph, so that the investment of raw materials can be reduced, the yield is improved, and meanwhile, the operation method is simple and has a good application prospect.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a gas chromatography-mass spectrum of a nicotine solution of the heavy component obtained in example 1;
FIG. 2 is a gas chromatography-mass spectrum of a nicotine solution of the light fraction obtained in example 1;
FIG. 3 is a gas chromatography-mass spectrum of the high purity nicotine solution obtained in example 1.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
Example 1
The nicotine purification method of this example is as follows:
putting nicotine with low purity obtained by conventional preparation into a short-distance molecular distiller, keeping the temperature in the short-distance molecular distiller at 60 ℃ and the pressure at 20mbar, rectifying the nicotine, and taking heavy components;
putting the heavy component into another short-path molecular distiller, keeping the temperature in the short-path molecular distiller at 80 ℃ and the pressure at 1mbar, rectifying the heavy component, and taking the light component;
petroleum ether, ethyl acetate, methanol and water are configured according to the volume ratio of 3:3:4:3, mixed and stirred, and are kept stand for layering, the lower layer is taken as a mobile phase, the upper layer is taken as a stationary phase, the stationary phase is injected into a high-speed counter-current chromatograph until the stationary phase is filled with the high-speed counter-current chromatograph, then a main machine of the high-speed counter-current chromatograph is started, the rotating speed is adjusted to 800r/min, the temperature of the constant temperature circulator is kept at 20 ℃, injecting mobile phase at 0.5ml/min, continuously injecting sample until obvious mobile phase flows out, dissolving light component in the mobile phase, continuously injecting sample, detecting the mobile phase with ultraviolet detector with wavelength of 240-280 nm, and when the ultraviolet detector detects that the flowing mobile phase contains the peak shape of nicotine, starting to collect the mobile phase, and concentrating after the collection is finished to obtain the high-purity nicotine.
Example 2
The nicotine purification method of this example is as follows:
putting nicotine with low purity obtained by conventional preparation into a short-distance molecular distiller, keeping the temperature in the short-distance molecular distiller at 20 ℃ and the pressure at 10mbar, rectifying the nicotine, and taking heavy components;
putting the heavy component into another short-path molecular distiller, keeping the temperature in the short-path molecular distiller at 40 ℃ and the pressure at 0.01mbar, and rectifying the heavy component to obtain a light component;
petroleum ether, ethyl acetate, methanol and water are configured according to the volume ratio of 5:5:7:6, mixed and stirred, and are kept stand for layering, the lower layer is taken as a mobile phase, the upper layer is taken as a stationary phase, the stationary phase is injected into a high-speed counter-current chromatograph until the stationary phase is filled with the high-speed counter-current chromatograph, then a main machine of the high-speed counter-current chromatograph is started, the rotating speed is adjusted to 1200r/min, the temperature of the constant temperature circulator is kept at 30 ℃, injecting the mobile phase at a speed of 5ml/min, continuously injecting the sample until obvious mobile phase flows out, dissolving the light component in the mobile phase, continuously injecting the sample, detecting the mobile phase with ultraviolet detector with wavelength of 240-280 nm, and when the ultraviolet detector detects that the flowing mobile phase contains the peak shape of nicotine, starting to collect the mobile phase, and concentrating after the collection is finished to obtain the high-purity nicotine.
Example 3
The nicotine purification method of this example is as follows:
putting nicotine with low purity obtained by conventional preparation into a short-distance molecular distiller, keeping the temperature in the short-distance molecular distiller at 40 ℃ and the pressure at 15mbar, rectifying the nicotine, and taking heavy components;
putting the heavy component into another short-path molecular distiller, keeping the temperature in the short-path molecular distiller at 60 ℃ and the pressure at 0.05mbar, and rectifying the heavy component to obtain a light component;
petroleum ether, ethyl acetate, methanol and water are configured according to the volume ratio of 4:4:6:6, mixed and stirred, and are kept stand for layering, the lower layer is taken as a mobile phase, the upper layer is taken as a stationary phase, the stationary phase is injected into a high-speed counter-current chromatograph until the stationary phase is filled with the high-speed counter-current chromatograph, then a main machine of the high-speed counter-current chromatograph is started, regulating the rotation speed to 1000r/min, keeping the temperature of the constant temperature circulator at 25 ℃, injecting the mobile phase at a speed of 3ml/min, continuously injecting the sample until obvious mobile phase flows out, dissolving the light component in the mobile phase, continuously injecting the sample, detecting the mobile phase with ultraviolet detector with wavelength of 240-280 nm, and when the ultraviolet detector detects that the flowing mobile phase contains the peak shape of nicotine, starting to collect the mobile phase, and concentrating after the collection is finished to obtain the high-purity nicotine.
Example 4
The nicotine purification method of this example is as follows:
putting nicotine with low purity obtained by conventional preparation into a short-distance molecular distiller, keeping the temperature in the short-distance molecular distiller at 40 ℃ and the pressure at 12mbar, rectifying the nicotine, and taking heavy components;
putting the heavy component into another short-path molecular distiller, keeping the temperature in the short-path molecular distiller at 60 ℃ and the pressure at 0.02mbar, and rectifying the heavy component to obtain a light component;
petroleum ether, ethyl acetate, methanol and water are configured according to the volume ratio of 4:4:5:5, mixed and stirred, and are kept stand for layering, the lower layer is taken as a mobile phase, the upper layer is taken as a stationary phase, the stationary phase is injected into a high-speed counter-current chromatograph until the stationary phase is filled with the high-speed counter-current chromatograph, then a main machine of the high-speed counter-current chromatograph is started, regulating the rotation speed to 1000r/min, keeping the temperature of the constant temperature circulator at 25 ℃, injecting the mobile phase at a speed of 2.6ml/min, continuously injecting the sample until obvious mobile phase flows out, dissolving the light component in the mobile phase, continuously injecting the sample, detecting the mobile phase with ultraviolet detector with wavelength of 240-280 nm, and when the ultraviolet detector detects that the flowing mobile phase contains the peak shape of nicotine, starting to collect the mobile phase, and concentrating after the collection is finished to obtain the high-purity nicotine.
The high purity nicotine prepared in the above examples 1 to 4 and the heavy and light components obtained in the middle were subjected to gas chromatography-mass spectrometry, respectively, and the yield of the high purity nicotine prepared in examples 1 to 4 was calculated, and the results of the detection and calculation are as follows:
the results of the measurement of the obtained high purity nicotine were as follows:
the detection results of the obtained light components were as follows:
the detection results of the obtained heavy components were as follows:
the yields of examples 1 to 4 were as follows
| Grouping | Example 1 | Example 2 | Example 3 | Example 4 |
| Yield (%) | 87.6 | 95.4 | 96.2 | 96.8 |
The nicotine purification method of the invention firstly adopts the short-path molecular distiller to carry out primary purification, impurities with larger boiling point difference and other alkaloids are separated, meanwhile, the short-path molecular distiller can prevent the nicotine from generating additional impurities in the distillation process as much as possible by adopting a low-temperature low-pressure high-efficiency distillation mode, which influences the quality and yield of the nicotine, and the short-path molecular distiller can improve the purification production efficiency by carrying out pretreatment, and then the nicotine purified by twice distillation is further separated by utilizing a high-speed counter-current chromatograph, because part of impurities in the nicotine are close to the boiling point of the nicotine, the separation is difficult in a conventional rectification mode, the temperature of the nicotine is higher, the rectification needs high-temperature treatment, the outward impurities are easy to be generated again, a specific stationary phase and mobile phase system are adopted to separate the nicotine, and the loss of materials can be reduced by adopting the high-speed counter-current chromatograph to carry out separation, and a large amount of solvents and solid-phase adsorption materials are not needed, so that the cost is greatly reduced, the waste solvents are prevented from polluting the environment, the elution step is omitted, and the production flow is shortened.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A method of nicotine purification comprising the steps of:
step one, putting nicotine to be treated into a short-range molecular distiller, and rectifying at the temperature of 20-60 ℃ and under the pressure of 10-20mbar to obtain heavy components;
step two, putting the heavy component obtained in the step one into a short-distance molecular distiller again, rectifying the heavy component at the temperature of 40-80 ℃ and under the pressure of 0.01-1mbar, and taking a light component;
dissolving the light component obtained in the step two in a mobile phase, feeding the light component into a high-speed counter-current chromatograph with established stationary phase-mobile phase dynamic balance through a sample injection valve, and collecting nicotine solution by utilizing an ultraviolet detector spectrum or a high performance liquid chromatography;
and step four, concentrating the nicotine solution obtained in the step three to obtain high-purity nicotine.
2. The method of nicotine purification according to claim 1, wherein in step one, the temperature is 40-60 ℃ and the pressure is 10-15 mbar.
3. The nicotine purification process according to claim 1, wherein in step two, the temperature is 60-80 ℃ and the pressure is 0.01-0.05 mbar.
4. The nicotine purification method according to claim 1, wherein in step three, the method for establishing stationary phase-mobile phase dynamic equilibrium by high-speed countercurrent chromatography comprises:
step one, respectively preparing a stationary phase solvent system and a mobile phase solvent system;
filling the high-speed counter-current chromatograph with the stationary phase, setting the temperature of the constant-temperature circulator, adjusting the rotating speed of a host of the high-speed counter-current chromatograph, finally pumping the mobile phase, detecting by using an ultraviolet detector, and when the mobile phase flows out obviously, establishing the stationary phase-mobile phase dynamic balance by the high-speed counter-current chromatograph.
5. The method of purifying nicotine according to claim 4, wherein the fixed phase solvent system and the mobile phase solvent system are prepared by mixing petroleum ether, ethyl acetate, methanol and water, stirring them uniformly, standing and layering, and taking the upper layer as the fixed phase and the lower layer as the mobile phase.
6. The nicotine purification method of claim 5, wherein the petroleum ether: ethyl acetate: methanol: the volume ratio of water is (3-5): (3-5): (4-7): (3-6).
7. The nicotine purification method of claim 6, wherein the petroleum ether: ethyl acetate: methanol: the volume ratio of water is (3-4): (3-4): (5-6): (5-6).
8. The nicotine purification method according to claim 4, wherein in step two, the temperature of the constant temperature circulator is 20-30 ℃.
9. The nicotine purification method as claimed in claim 4, wherein in the second step, the rotation speed of the high-speed countercurrent chromatograph is 800-1200 r/min.
10. The nicotine purification method of claim 4, in which the mobile phase is pumped at a rate of 0.5 to 5 ml/min.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113861165A (en) * | 2021-11-18 | 2021-12-31 | 湖北和诺生物工程股份有限公司 | Two-phase extraction method of nicotine |
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Denomination of invention: A Method for Purification of Nicotine Effective date of registration: 20230912 Granted publication date: 20221108 Pledgee: China Construction Bank Corporation Enshi branch Pledgor: HUBEI HENO BIOLOGICAL ENGINEERING CO.,LTD. Registration number: Y2023980056381 |
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