CN112715555A - Synthetic method and application of nicotine salt - Google Patents
Synthetic method and application of nicotine salt Download PDFInfo
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- CN112715555A CN112715555A CN202011510677.1A CN202011510677A CN112715555A CN 112715555 A CN112715555 A CN 112715555A CN 202011510677 A CN202011510677 A CN 202011510677A CN 112715555 A CN112715555 A CN 112715555A
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- nicotine salt
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a synthesis method and application of nicotine salt, which comprises the following steps: s1, putting liquid nicotine, organic acid and an organic solvent into the reaction kettle I according to a certain proportion, and heating and stirring for reaction to obtain initial liquid nicotine salt; s2, putting a certain proportion of reaction liquid into a reaction kettle II according to the feeding sequence of the organic solvent, the binder and the sustained-release agent, adjusting the pH to 7-9, and heating, stirring and reacting to obtain a first reaction liquid; s3, putting the initial liquid nicotine salt, the first reaction liquid and the organic acid into a reaction kettle III according to a certain proportion, adjusting the pH to 7-9, heating and stirring to react to obtain a nicotine salt solution; s4, distilling the S3 nicotine salt solution to obtain powdery solid nicotine salt. The nicotine salt prepared by the method has stable state, is not easy to volatilize, has slow release effect, and is suitable for application in the field of pesticides.
Description
Technical Field
The invention relates to the field of chemical synthesis, in particular to a synthetic method and application of nicotine salt.
Background
Nicotine salts, i.e. nicotine salts, which is a form of nicotine characterized by the presence of interactions between nicotine in ionic form and in ionic form, e.g. organic acids. There are a wide variety of nicotine salts known today, for example, nicotine sulfate has been sold as an insecticide; nicotine tartrate can be used for the treatment of gastric ulcerative colitis; the strawberry acid, the glyceric acid, the fumaric acid and the nicotine are mixed to prepare salt, and the salt is added into the electronic cigarette liquid, so that the smoking mouth feel is comfortable.
Free nicotine has the defects of unstable state and extremely high volatility, and when the free nicotine is applied to insecticides, the problems of quick volatilization, poor pesticide effect and unsatisfactory prevention and treatment effect of the insecticides are easily caused. Therefore, how to prepare the stable and nonvolatile nicotine salt and realize the sustained and controlled release effect of the release of the nicotine pesticide is the key of the research on the nicotine pesticide.
Disclosure of Invention
In view of this, the present invention provides a method for synthesizing stable and nonvolatile nicotine salt and its application.
The technical scheme of the invention is realized as follows: the invention provides a synthesis method of nicotine salt and application thereof, comprising the following steps:
s1, putting the liquid nicotine, the organic acid and the organic solvent into the reaction kettle I according to a certain proportion, heating and stirring for reaction to obtain initial liquid nicotine salt;
s2, according to the feeding sequence of the organic solvent, the adhesive and the sustained-release agent, the organic solvent, the adhesive and the sustained-release agent are fed into a reaction kettle II according to a certain proportion, pH of the reaction solution is adjusted to 7-9 by using an acid-base regulator, and the reaction solution is heated, stirred and reacted to obtain a first reaction solution;
s3, putting the initial liquid nicotine salt, the first reaction liquid and the organic acid into a reaction kettle III according to a certain proportion, adjusting the pH of the reaction liquid to 7-9 by using an acid-base regulator, and heating and stirring for reaction to obtain a nicotine salt solution;
s4, distilling the S3 nicotine salt solution to obtain powdery solid nicotine salt.
On the basis of the above technical scheme, preferably, the purity of the liquid nicotine is not lower than 99%.
On the basis of the technical scheme, preferably, the organic acid is one or a combination of more of glutamic acid, arginine, phenylalanine, tyrosine, dodecanedioic acid, dodecahydroxystearic acid, heptanoic acid and citric acid.
On the basis of the technical scheme, preferably, nitrogen is introduced into the reaction kettle I and the reaction kettle III.
On the basis of the technical scheme, preferably, the organic solvent is one or a combination of more of pyridine, dimethyl sulfoxide, ethylene glycol and dimethylformamide.
On the basis of the technical scheme, preferably, the binder is one or a combination of more of sodium alginate, chitosan, hydroxymethyl cellulose, polyvinyl alcohol and polybutylene adipate.
On the basis of the technical scheme, preferably, the acid-base regulator is one or a combination of more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, sodium citrate or potassium citrate.
On the basis of the technical scheme, preferably, the slow release agent is one or the combination of two of beta cyclodextrin and hydroxypropyl methyl cellulose.
On the basis of the above technical scheme, preferably, the mass ratio of the liquid nicotine to the organic acid to the organic solvent in the step S1 is (3-7) to (5-10) to (8-15), the heating temperature is 60-100 ℃, and the heating and stirring reaction time is 20-30 minutes.
On the basis of the technical scheme, preferably, the mass ratio of the organic solvent to the binder to the sustained-release agent in the step S2 is (8-15) to (6-10) to (3-7), the heating temperature is 60-80 ℃, and the heating and stirring reaction time is 10-20 minutes.
On the basis of the above technical scheme, preferably, the mass ratio of the initial liquid nicotine salt, the first reaction solution and the organic acid in the step S3 is (7-18): (8-15): (10-20), the heating temperature is 50-80 ℃, and the heating and stirring reaction time is 10-20 minutes.
Further preferred is the use of a nicotine salt for the preparation of a pesticide.
Compared with the prior art, the synthesis method and the application of the nicotine salt have the following beneficial effects:
(1) the invention adds the adhesive and the slow release agent as the auxiliary agent on the basis of selecting the high-purity nicotine and the organic acid, and the prepared nicotine salt has good stability and is not easy to volatilize, and the prepared nicotine salt solution is colorless and transparent.
(2) The nicotine salt provided by the invention is applied to the insecticide, and can effectively slow down the volatilization of the insecticide, delay the decomposition of the insecticide and improve the drug effect, thereby improving the insect control effect.
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 invention provides a synthesis method of nicotine salt, which comprises the following steps:
s1, putting liquid nicotine, dodecahydroxystearic acid and pyridine with the purity of not less than 99% into a reaction kettle I, wherein the mass ratio of the liquid nicotine to the dodecahydroxystearic acid to the pyridine is 3: 5: 8, and stirring and reacting for 20 minutes at the temperature of 60 ℃ under the condition that nitrogen is introduced into the reaction kettle to obtain initial liquid nicotine salt;
s2, putting the reaction materials into a reaction kettle II according to the sequence of dimethyl sulfoxide, sodium alginate and beta-cyclodextrin, wherein the mass ratio of the dimethyl sulfoxide to the sodium alginate to the beta-cyclodextrin is 15: 10: 7, adjusting the pH of the reaction solution to 7 by using sodium carbonate and potassium carbonate, and stirring and reacting for 10 minutes at the temperature of 60 ℃ to obtain a first reaction solution;
s3, putting initial liquid nicotine salt, first reaction liquid and heptanoic acid into a reaction kettle III, adjusting the pH of the reaction liquid to 7 by using sodium carbonate and potassium carbonate, and stirring for reacting for 10 minutes at 50 ℃ under the condition that nitrogen is introduced into the reaction kettle, wherein the mass ratio of the initial liquid nicotine salt to the first reaction liquid to the heptanoic acid is 18: 15: 20;
s4, distilling the S3 nicotine salt solution to obtain powdery solid nicotine salt.
Example 2
The invention provides a synthesis method of nicotine salt, which comprises the following steps:
s1, putting liquid nicotine with the purity not lower than 99%, citric acid and dimethylformamide into a reaction kettle I, wherein the mass ratio of the liquid nicotine to the citric acid to the dimethylformamide is 7: 10: 15, and stirring and reacting for 30 minutes at 100 ℃ under the condition that nitrogen is introduced into the reaction kettle to obtain initial liquid nicotine salt;
s2, putting the reaction materials into a reaction kettle II according to the sequence of ethylene glycol, chitosan and hydroxypropyl methyl cellulose, adjusting the pH of the reaction solution to 9 by using potassium carbonate and potassium citrate according to the mass ratio of the ethylene glycol, the chitosan and the hydroxypropyl methyl cellulose to be 8: 6: 3, and stirring and reacting for 20 minutes at 80 ℃ to obtain a first reaction solution;
s3, putting initial liquid nicotine salt, first reaction liquid and heptanoic acid into a reaction kettle III, adjusting the pH of the reaction liquid to 9 by using potassium carbonate and potassium citrate, and stirring and reacting for 20 minutes at 80 ℃ under the condition that nitrogen is introduced into the reaction kettle to obtain a nicotine salt solution, wherein the mass ratio of the initial liquid nicotine salt to the first reaction liquid to the heptanoic acid is 7: 8: 10;
s4, distilling the S3 nicotine salt solution to obtain powdery solid nicotine salt.
Example 3
The invention provides a synthesis method of nicotine salt, which comprises the following steps:
s1, putting liquid nicotine, heptanoic acid and dimethylformamide with the purity of not less than 99% into a reaction kettle I, wherein the mass ratio of the liquid nicotine to the heptanoic acid to the dimethylformamide is 4: 6: 9, and stirring and reacting for 22 minutes at 70 ℃ under the condition that nitrogen is introduced into the reaction kettle to obtain initial liquid nicotine salt;
s2, putting the reaction materials into a reaction kettle II according to the sequence of dimethyl sulfoxide, polybutylene adipate, beta-cyclodextrin and hydroxypropyl methyl cellulose, adjusting the pH value of the reaction solution to 8 by using potassium bicarbonate and sodium citrate according to the mass ratio of 9: 7: 2 of the dimethyl sulfoxide, the polybutylene adipate, the beta-cyclodextrin and the hydroxypropyl methyl cellulose, and stirring and reacting for 12 minutes at 70 ℃ to obtain a first reaction solution;
s3, putting initial liquid nicotine salt, first reaction liquid and citric acid into a reaction kettle III, adjusting the pH of the reaction liquid to 8 by using potassium bicarbonate and sodium citrate, and stirring and reacting for 15 minutes at 60 ℃ under the condition that nitrogen is introduced into the reaction kettle to obtain a nicotine salt solution, wherein the mass ratio of the initial liquid nicotine salt to the first reaction liquid to the citric acid is 10: 12: 15;
s4, distilling the S3 nicotine salt solution to obtain powdery solid nicotine salt.
Example 4
The invention provides a synthesis method of nicotine salt, which comprises the following steps:
s1, putting liquid nicotine with the purity not lower than 99%, glutamic acid, phenylalanine, dimethyl sulfoxide and glycol into a reaction kettle I, wherein the mass ratio of the liquid nicotine to the glutamic acid to the phenylalanine to the dimethyl sulfoxide to the glycol is 5: 4: 6: 7: 8, and stirring and reacting for 25 minutes at 80 ℃ under the condition that nitrogen is introduced into the reaction kettle to obtain initial liquid nicotine salt;
s2, putting the reaction materials into a reaction kettle II according to the sequence of pyridine, dimethyl sulfoxide, sodium alginate, chitosan and beta cyclodextrin, wherein the mass ratio of the pyridine to the dimethyl sulfoxide to the sodium alginate to the chitosan to the beta cyclodextrin is 5: 6: 3: 5: 4: 3, adjusting the pH of the reaction solution to 7 by using sodium carbonate and sodium citrate, and stirring and reacting for 18 minutes at 65 ℃ to obtain a first reaction solution;
s3, putting initial liquid nicotine salt, first reaction liquid, phenylalanine and dodecane dibasic acid into a reaction kettle III, adjusting the pH of the reaction liquid to 8 by using sodium carbonate and sodium citrate, and stirring and reacting for 17 minutes at 65 ℃ under the condition that nitrogen is introduced into the reaction kettle to obtain a nicotine salt solution, wherein the mass ratio of the initial liquid nicotine salt to the first reaction liquid to the phenylalanine to the dodecane dibasic acid is 12: 14: 7: 8;
s4, distilling the S3 nicotine salt solution to obtain powdery solid nicotine salt.
Example 5
The invention provides a synthesis method of nicotine salt, which comprises the following steps:
s1, putting liquid nicotine with the purity not lower than 99%, phenylalanine, citric acid, pyridine, glycol and dimethylformamide into a reaction kettle I, wherein the mass ratio of the liquid nicotine to the phenylalanine to the citric acid to the pyridine to the glycol to the dimethylformamide is 7: 4: 5: 4: 6: 5, and stirring and reacting for 26 minutes under the conditions that the temperature is 90 ℃ and nitrogen is introduced into the reaction kettle to obtain initial liquid nicotine salt;
s2, putting the reaction materials into a reaction kettle II according to the sequence of dimethyl sulfoxide, dimethyl formamide, chitosan, polyvinyl alcohol, poly (butylene adipate) and beta-cyclodextrin, wherein the mass ratio of the dimethyl sulfoxide to the dimethyl formamide to the chitosan to the polyvinyl alcohol to the poly (butylene adipate) to the beta-cyclodextrin is 6: 7: 3: 4: 7, adjusting the pH value of the reaction solution to 8 by using potassium bicarbonate and sodium citrate, and stirring and reacting for 19 minutes at 75 ℃ to obtain a first reaction solution;
s3, putting initial liquid nicotine salt, first reaction liquid, tyrosine, dodecahydroxystearic acid and citric acid into a reaction kettle III, adjusting the pH of the reaction liquid to 8 by using potassium bicarbonate and sodium citrate, and stirring and reacting for 13 minutes under the conditions of 76 ℃ and introducing nitrogen into the reaction kettle to obtain a nicotine salt solution, wherein the mass ratio of the initial liquid nicotine salt to the first reaction liquid to the tyrosine to the dodecahydroxystearic acid to the citric acid is 16: 15: 5: 6: 9;
s4, distilling the S3 nicotine salt solution to obtain powdery solid nicotine salt.
Example 6
A synthesis method of nicotine salt comprises the following steps:
s1, putting liquid nicotine with the purity not lower than 99%, glutamic acid, phenylalanine, dimethyl sulfoxide and glycol into a reaction kettle I, wherein the mass ratio of the liquid nicotine to the glutamic acid to the phenylalanine to the dimethyl sulfoxide to the glycol is 5: 4: 6: 7: 8, and stirring and reacting for 25 minutes at the temperature of 80 ℃ to obtain a nicotine salt solution;
s2, distilling the nicotine salt solution to obtain powdery solid nicotine salt.
Examples 1-5 are synthetic methods of the present invention and example 6 is a conventional synthetic method, as a control of the present invention. The nicotine salt synthesized by the invention is added into deltamethrin insecticide and is sprayed on aphids of hot pepper plants, and the dosage is 20g/667m2The results of comparing the effects of the agricultural chemicals of the examples are shown in Table 1.
TABLE 1 examples 1-6 aphid lethality
As can be seen from table 1, the nicotine salt prepared without adding a binder and a sustained release agent in the prior art, that is, the nicotine salt synthesized in example 6 is added to the deltamethrin insecticide, and the drug effect is 89% -94% of the average drug effect value of examples 1-5, thereby demonstrating that the nicotine salt synthesized by the invention is added to the deltamethrin insecticide, so that the volatilization of pesticides is effectively slowed down, the aphid mortality is increased, and the drug effect of deltamethrin is improved.
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 for synthesizing a nicotine salt, which is characterized by comprising the following steps: the method comprises the following steps:
s1, putting the liquid nicotine, the organic acid and the organic solvent into the reaction kettle I according to a certain proportion, heating and stirring for reaction to obtain initial liquid nicotine salt;
s2, according to the feeding sequence of the organic solvent, the adhesive and the sustained-release agent, the organic solvent, the adhesive and the sustained-release agent are fed into a reaction kettle II according to a certain proportion, pH of the reaction solution is adjusted to 7-9 by using an acid-base regulator, and the reaction solution is heated, stirred and reacted to obtain a first reaction solution;
s3, putting the initial liquid nicotine salt, the first reaction liquid and the organic acid into a reaction kettle III according to a certain proportion, adjusting the pH of the reaction liquid to 7-9 by using an acid-base regulator, and heating and stirring for reaction to obtain a nicotine salt solution;
s4, distilling the S3 nicotine salt solution to obtain powdery solid nicotine salt.
2. A method of synthesizing a nicotine salt as claimed in claim 1, wherein: the purity of the liquid nicotine is not less than 99%.
3. A method of synthesizing a nicotine salt as claimed in claim 1, wherein: the organic acid is one or a combination of glutamic acid, arginine, phenylalanine, tyrosine, dodecanedioic acid, dodecahydroxystearic acid, heptanoic acid and citric acid.
4. A method of synthesizing a nicotine salt as claimed in claim 1, wherein: and introducing nitrogen into the reaction kettle I and the reaction kettle III.
5. A method of synthesizing a nicotine salt as claimed in claim 1, wherein: the organic solvent is one or a combination of more of pyridine, dimethyl sulfoxide, ethylene glycol and dimethylformamide; the binder is one or a combination of more of sodium alginate, chitosan, hydroxymethyl cellulose, polyvinyl alcohol and polybutylene adipate; the acid-base regulator is one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, sodium citrate or potassium citrate.
6. A method of synthesizing a nicotine salt as claimed in claim 1, wherein: the slow release agent is one or the combination of two of beta-cyclodextrin and hydroxypropyl methyl cellulose.
7. A method of synthesizing a nicotine salt as claimed in claim 1, wherein: in the step S1, the mass ratio of the liquid nicotine to the organic acid to the organic solvent is (3-7) to (5-10) to (8-15), the heating temperature is 60-100 ℃, and the heating and stirring reaction time is 20-30 minutes.
8. A method of synthesizing a nicotine salt as claimed in claim 1, wherein: in the step S2, the mass ratio of the organic solvent to the adhesive to the sustained-release agent is (8-15) to (6-10) to (3-7), the heating temperature is 60-80 ℃, and the heating and stirring reaction time is 10-20 minutes.
9. A method of synthesizing a nicotine salt as claimed in claim 1, wherein: in the step S3, the mass ratio of the initial liquid nicotine salt to the first reaction liquid to the organic acid is (7-18) to (8-15) to (10-20), the heating temperature is 50-80 ℃, and the heating and stirring reaction time is 10-20 minutes.
10. Use of a nicotine salt prepared by a method according to any one of claims 1-9 for the preparation of a pesticide.
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| CN202011510677.1A CN112715555A (en) | 2020-12-18 | 2020-12-18 | Synthetic method and application of nicotine salt |
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| CN202011510677.1A CN112715555A (en) | 2020-12-18 | 2020-12-18 | Synthetic method and application of nicotine salt |
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Cited By (2)
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| CN113197327A (en) * | 2021-05-13 | 2021-08-03 | 云南中烟工业有限责任公司 | Gel based on long-chain alkyl dibasic fatty acid nicotine salt gelling agent |
| CN113812665A (en) * | 2021-10-08 | 2021-12-21 | 云南巴菰生物科技股份有限公司 | Electronic cigarette atomized liquid containing betelnut citrate salt and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113197327A (en) * | 2021-05-13 | 2021-08-03 | 云南中烟工业有限责任公司 | Gel based on long-chain alkyl dibasic fatty acid nicotine salt gelling agent |
| CN113812665A (en) * | 2021-10-08 | 2021-12-21 | 云南巴菰生物科技股份有限公司 | Electronic cigarette atomized liquid containing betelnut citrate salt and preparation method thereof |
| CN113812665B (en) * | 2021-10-08 | 2022-07-08 | 云南巴菰生物科技股份有限公司 | Electronic cigarette atomized liquid containing betelnut citrate salt and preparation method thereof |
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