CN111961032A - Preparation method of synthetic nicotine salt and composition thereof - Google Patents
Preparation method of synthetic nicotine salt and composition thereof Download PDFInfo
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- CN111961032A CN111961032A CN202010569649.0A CN202010569649A CN111961032A CN 111961032 A CN111961032 A CN 111961032A CN 202010569649 A CN202010569649 A CN 202010569649A CN 111961032 A CN111961032 A CN 111961032A
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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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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/10—Chemical features of tobacco products or tobacco substitutes
- A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
- A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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Abstract
The invention relates to a preparation method of synthetic nicotine salt, which is characterized by comprising the following steps: (1) mixing synthetic nicotine raw material with propylene glycol and glycerol according to a certain weight ratio to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; (2) adding acid into the transparent liquid obtained in the step (1), heating and stirring, refluxing at 60-120 ℃ for 0.2-2h, and cooling to room temperature to obtain the synthetic nicotine salt. The synthetic nicotine salt obtained by the method has the advantages of greatly improved yield, simple and easy operation of the preparation method, high practicability, cost saving and suitability for industrial mass production. The invention also relates to a tobacco tar composition and a preparation method thereof, the composition comprises synthetic nicotine salt, propylene glycol and glycerol, wherein the synthetic nicotine salt is prepared by the method.
Description
Technical Field
The invention relates to the field of electronic cigarette oil, in particular to a preparation method of high-yield synthetic nicotine salt and a composition thereof.
Background
Nicotine, 3- [ 1-methylpyrrolidin-2-yl ] pyridine, is a molecular alkaloid,
naturally produced by some solanaceous plants, often referred to as nicotine, which include not only tobacco, but also pepper, tomato, potato, eggplant or petunia. Among these plants, tobacco is one of the most abundant plants with nicotine content, accounting for 8% -14%, which is also responsible for its use in cigarettes.
The emergence of electronic cigarettes has changed the fate of millions of smokers, and the emergence of nicotine salt tobacco tar has further promoted the healthy development of small smoke tides. Compared with the traditional nicotine tobacco tar extracted from tobacco, the nicotine salt tobacco tar has higher content of synthesized nicotine salt, can be easily absorbed by human blood, can relieve the nicotine requirement of nicotine addicts, has more comfortable inhalation feeling and addiction relieving capability, can achieve the advantages of quick addiction relieving and small smoke without interfering other people when being properly applied to low-power equipment, and does not cause unacceptable throat hitting experience when pursuing high nicotine unlike the traditional tobacco tar.
Nicotine salt is a nicotine extracted from tobacco leaves found in nature, and if this form of nicotine is added to the liquid to be aspirated, the nicotine solution needs to be aspirated at extremely high temperatures to be effective and not as readily absorbed (bioavailable) as free-radical nicotine. Therefore, some improvements are needed.
The free base nicotine has a higher ph value, resulting in an increased alkalinity. This sharp increase in alkalinity can lead to more severe throat pain, resulting in people having less steam than they need. The acid has a counter-acting effect, reducing the ph of the nicotine, reducing the alkalinity in the process, and the end result is a smoother steaming experience.
One of the greatest benefits of using nicotine salts is that higher nicotine levels can be more easily inhaled by the human blood, unlike free nicotine smoke, which can cause an unacceptable throat choking sensation. The nicotine salt has smooth throat-hitting feeling, and at present, a lot of tobacco tar is 50mg, and the nicotine can bring strong nicotine experience to smokers without choking the throat.
Regarding nicotine salt, in the prior art, CN110477442, published japanese patent No. 2019.11.22 discloses a compound nicotine salt and a preparation method thereof, which is prepared from the following raw materials: 40-60 parts of organic acid and 40-60 parts of nitrending, wherein the organic acid comprises benzoic acid, linolenic acid, linoleic acid, citric acid, malic acid, ascorbic acid and other organic acids. This application does not contain any description of the product yield.
The prior patent application CN110452219 of the applicant, published with the number of 2019.11.15, discloses a nicotine salt and a preparation method thereof, wherein the nicotine salt comprises benzoic acid, anhydrous citric acid and nicotine, and the benzoic acid, the anhydrous citric acid and the nicotine are prepared by reacting according to the mass ratio of 1:0.5-2: 2-3. This application also does not describe the yield of the product. Patent application CN110483479, published japanese patent No. 2019.11.22, discloses a high-stability nicotine salt and a preparation method thereof, wherein the raw materials comprise nicotine and m-hydroxybenzoic acid in a mass ratio of (1.8-2.85): 1. this application describes the product yield (page 4 of the specification), but the product is m-hydroxybenzoate and the yields are not high, 65%, 68%, 73%, 75%, 70%, 66%, respectively.
Thus, no report of improving the yield of nicotine benzoate exists in the prior art, and in the prior art, nicotine and acid are reacted to form nicotine salt, and other substances are added to form tobacco tar. The inventor of the invention has conducted extensive research to obtain a novel preparation method of nicotine benzoate with high yield.
Disclosure of Invention
The invention aims to provide a preparation method of a synthetic nicotine salt with high yield.
In order to achieve the above object, the present invention relates to a method for preparing a synthetic nicotine salt, which is characterized by comprising the steps of:
(1) mixing the synthetic nicotine raw material with propylene glycol and glycerol according to a certain weight ratio to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid;
(2) adding acid into the transparent liquid obtained in the step (1), heating and stirring, refluxing at 60-120 ℃ for 0.2-2h, and cooling to room temperature to obtain the synthetic nicotine salt.
In the method for preparing a synthetic nicotine salt according to the present invention, in step (1), the propylene glycol may be 1, 2-propylene glycol or 1, 3-propylene glycol, and preferably 1, 2-propylene glycol. The glycerol in the step (1) can be vegetable glycerol.
The preparation method of the synthetic nicotine salt of the present invention comprises the following steps of (1) synthesizing nicotine, propylene glycol and glycerin in a weight ratio of 1: 0.1-1: 0.1 to 1, preferably 1: 0.2-0.9: 0.2 to 0.9, more preferably 1: 0.2-0.4: 0.2-0.4.
In the method for producing a synthetic nicotine salt according to the present invention, the acid in the step (2) is an organic acid, and examples thereof include benzoic acid, citric acid, malic acid, lactic acid, tartaric acid, etc., preferably benzoic acid and lactic acid, and more preferably benzoic acid.
The above method for preparing a synthetic nicotine salt according to the present invention, wherein the amount of the acid used in step (2) is mixture a: acid 1: 0.1 to 1 (weight ratio), preferably mixture a: the acid is 1:0.3-1 (weight ratio), and more preferably mixture a: acid 1:0.5-1 (weight ratio).
The method for preparing a synthetic nicotine salt according to the present invention may further include adding water and/or alcohol in step (2), wherein the amount of the water and/or alcohol added is mixture a: water and/or alcohol ═ 1: 0.01-:0.2 (weight ratio), preferably mixture a: water and/or alcohol 1:0.01-0.1 (by weight), more preferably mixture a: water and/or alcohol 1:0.01-0.05 (weight ratio).
The yield of the synthetic nicotine salt is more than 99.5%, preferably more than 99.8%. The method for determining the yield can be performed according to a method known to those skilled in the art.
It is another object of the present invention to provide a tobacco tar composition, characterized in that the composition comprises a synthetic nicotine salt, propylene glycol, glycerol, wherein the synthetic nicotine salt is prepared by the following method:
(1) mixing the synthetic nicotine raw material with propylene glycol and glycerol according to a certain weight ratio to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid;
(2) adding acid into the transparent liquid obtained in the step (1), heating and stirring, refluxing at 60-120 ℃ for 0.2-2h, and cooling to room temperature to obtain the synthetic nicotine salt.
In the tobacco tar composition according to the present invention, the synthetic nicotine salt is an organic acid synthetic nicotine salt, and examples thereof include benzoate, citrate, malate, lactate, and tartrate, preferably benzoate and lactate, and more preferably benzoate. The propylene glycol in the tobacco tar composition and step (1) may be 1, 2-propylene glycol or 1, 3-propylene glycol, and preferably 1, 2-propylene glycol. The tobacco tar composition and the glycerin in the step (1) may be vegetable glycerin. The acid in the step (2) is an organic acid, and includes benzoic acid, citric acid, malic acid, lactic acid, tartaric acid, etc., preferably benzoic acid and lactic acid, and more preferably benzoic acid.
The tobacco tar composition of the present invention comprises 1 to 15.0 parts by weight of synthetic nicotine salt, 15.0 to 84.0 parts by weight of propylene glycol, and 15.0 to 70.0 parts by weight of glycerin, preferably 5.0 to 12.0 parts by weight of synthetic nicotine salt, 35.0 to 60.0 parts by weight of propylene glycol, and 28.0 to 57.0 parts by weight of glycerin.
The preparation method of the synthetic nicotine salt of the present invention comprises the following steps of (1) synthesizing nicotine, propylene glycol and glycerin in a weight ratio of 1: 0.1-1: 0.1 to 1, preferably 1: 0.2-0.9: 0.2 to 0.9, more preferably 1: 0.2-0.4: 0.2-0.4.
In the method for producing a synthetic nicotine salt according to the present invention, the acid in the step (2) is an organic acid, and examples thereof include benzoic acid, citric acid, malic acid, lactic acid, tartaric acid, etc., preferably benzoic acid and lactic acid, and more preferably benzoic acid.
The above method for preparing a synthetic nicotine salt according to the present invention, wherein the amount of the acid used in step (2) is mixture a: acid 1: 0.1 to 1 (weight ratio), preferably mixture a: the acid is 1:0.3-1 (weight ratio), and more preferably mixture a: acid 1:0.5-1 (weight ratio).
The method for preparing a synthetic nicotine salt according to the present invention may further include adding water and/or alcohol in step (2), wherein the amount of the water and/or alcohol added is mixture a: water and/or alcohol ═ 1: 0.01-:0.2 (weight ratio), preferably mixture a: water and/or alcohol 1:0.01-0.1 (by weight), more preferably mixture a: water and/or alcohol 1:0.01-0.05 (weight ratio).
The invention also aims to provide a preparation method of the tobacco tar composition, which comprises the steps of mixing the synthetic nicotine salt, the propylene glycol and the glycerol according to a certain proportion to obtain the tobacco tar composition; wherein the synthetic niflumin salt is prepared by the following method:
(1) mixing the synthetic nicotine raw material with propylene glycol and glycerol according to a certain weight ratio to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid;
(2) adding acid into the transparent liquid obtained in the step (1), heating and stirring, refluxing at 60-120 ℃ for 0.2-2h, and cooling to room temperature to obtain the synthetic nicotine salt.
The tobacco tar composition of the invention can be further added with other substances commonly used in the field according to the needs, such as spices for regulating smell, mouthfeel and the like.
Propylene glycol and glycerin are generally added into tobacco tar compositions in the prior art, but the propylene glycol and the glycerin are used for synthesizing nicotine salt to improve the yield of the synthesized nicotine salt, so the technical proposal is not provided in the field, and the technical proposal is not thought by the technical personnel in the field. In the course of research, the present inventors surprisingly found that the yield of the synthetic nicotine salt can be unexpectedly and greatly improved by mixing propylene glycol and glycerin, which are commonly used in the tobacco oil composition, with the synthetic nicotine and then reacting with acid, and using a small amount of propylene glycol and glycerin, and the yield of the synthetic nicotine salt obtained by the preparation method of the present invention is above 99.5%, preferably above 99.8%.
Compared with the prior art, the preparation method of the synthetic nicotine salt does not introduce additional impurity substances, and the yield of the synthetic nicotine salt is greatly improved. Meanwhile, the preparation method has the advantages of simple process, easy operation, high practicability and cost saving, and is suitable for industrial mass production.
The tobacco tar composition prepared from the synthetic nicotine salt prepared by the invention has higher purity, clear and thorough appearance and better smoking experience.
Detailed Description
The present invention will be described in detail below with reference to specific examples, but the present invention is not limited to these examples.
Example 1
According to the weight ratio of 1: 0.3: 0.35 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: benzoic acid is 1: adding benzoic acid at a ratio of 0.7, heating and stirring at 100 deg.C, refluxing for 2 hr, and cooling to room temperature to obtain synthetic nicotine benzoate with yield of 99.9%.
Example 2
According to the weight ratio of 1: 0.7: 0.5 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: benzoic acid is 1: adding benzoic acid at a ratio of 0.4, heating and stirring at 110 deg.C, refluxing for 5 hr, and cooling to room temperature to obtain synthetic nicotine benzoate with yield of 99.7%.
Example 3
According to the weight ratio of 1: 0.6: 0.9 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the obtained transparent liquid, the mixture a: benzoic acid is 1: adding benzoic acid at a ratio of 0.4, heating and stirring at 50 deg.C, refluxing for 8 hr, and cooling to room temperature to obtain synthetic nicotine benzoate with yield of 99.8%.
Example 4
According to the weight ratio of 1: 0.9: 0.2 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: lactic acid is 1: adding lactic acid at a ratio of 0.3, heating and stirring at 90 deg.C, refluxing for 3.6 hr, and cooling to room temperature to obtain synthetic nicotine lactate with yield of 99.6%.
Example 5
According to the weight ratio of 1: 0.5: 0.5 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the obtained transparent liquid, the mixture a: lactic acid is 1: adding lactic acid at a ratio of 0.7, heating and stirring at 70 deg.C, refluxing for 1.5 hr, and cooling to room temperature to obtain synthetic nicotine lactate with yield of 99.6%.
Example 6
According to the weight ratio of 1: 0.8: 0.9 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: citric acid is 1: 0.2, heating and stirring at 105 ℃, refluxing for 1h, and cooling to room temperature to obtain the synthetic nicotine citrate with the yield of 99.7%.
Example 7
According to the weight ratio of 1: 0.9: 0.1 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: malic acid is 1: adding L-malic acid at a ratio of 0.2, heating and stirring at 100 deg.C, refluxing for 2.8 hr, and cooling to room temperature to obtain synthetic nicotine malate with yield of 99.5%.
Example 8
According to the weight ratio of 1: 0.8: 0.8 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: tartaric acid is 1: 0.1, adding tartaric acid according to the weight ratio of the mixture A: distilled water is 1: adding water at a ratio of 0.01, heating and stirring at 112 deg.C, refluxing for 5 hr, and cooling to room temperature to obtain synthetic nicotine tartrate with yield of 99.8%.
Example 9
According to the weight ratio of 1: 0.9: 0.5 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: tartaric acid is 1: 0.15, adding tartaric acid according to the weight ratio of the mixture A: distilled water is 1: adding water at a ratio of 0.02, heating and stirring at 105 deg.C, refluxing for 3.5 hr, and cooling to room temperature to obtain synthetic nicotine tartrate with yield of 99.9%.
Example 10
According to the weight ratio of 1: 0.8: 0.2 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: lactic acid is 1: 0.4, adding lactic acid according to the weight ratio of the mixture A: ethanol is 1: adding ethanol at a ratio of 0.01, heating and stirring at 80 deg.C, refluxing for 1.5 hr, and cooling to room temperature to obtain synthetic nicotine lactate with yield of 99.7%.
Example 11
According to the weight ratio of 1: 0.9: 0.3 respectively weighing synthetic nicotine, 1, 2-propylene glycol and glycerol, mixing to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid; in the transparent liquid obtained, by weight, mixture a: benzoic acid is 1: 0.4 of benzoic acid, the weight ratio of mixture A: distilled water and ethanol were 1: adding water and ethanol at a ratio of 0.01, heating and stirring at 78 deg.C, refluxing for 0.8 hr, and cooling to room temperature to obtain synthetic nicotine benzoate with yield of 99.9%.
Example 12
10 parts by weight of the synthetic nicotine benzoate obtained in example 1 of the present invention, 48 parts by weight of propylene glycol and 42 parts by weight of glycerin were uniformly mixed to prepare a tobacco tar composition according to the present invention.
Example 13
5 parts by weight of the synthetic nicotine benzoate obtained in example 1 of the present invention, 60 parts by weight of propylene glycol and 35 parts by weight of glycerin were uniformly mixed to prepare a tobacco tar composition according to the present invention.
Example 14
8 parts by weight of the synthetic nicotine benzoate obtained in example 1 of the present invention, 48 parts by weight of propylene glycol and 44 parts by weight of glycerin were uniformly mixed to prepare a tobacco tar composition according to the present invention.
Example 17
The different weight ratios of the synthetic nicotine, propylene glycol and glycerol have an influence on the yield of the synthetic nicotine acid salt.
The test was conducted in the same manner as in example 1 except that the weight ratio of synthetic nicotine, propylene glycol and glycerin was changed, and the results were as shown in Table 1.
Table 1: influence of different synthetic nicotine, propylene glycol, glycerol weight ratio on yield
It can be seen that within the weight ratio range of the present invention, high yields of the synthetic nicotinic acid salt are obtained, whereas without the addition of propylene glycol and glycerol, or within the weight ratio range of the present invention, low yields of the synthetic nicotinic acid salt are obtained.
Example 18 tobacco oil evaluation
The appearance and smoking experience of the tobacco products of examples 12-14 were evaluated and the results are shown in Table 2.
Table 2:
| appearance of the product | Irritation property | |
| Example 12 | Clear and transparent | Without choking throat |
| Example 13 | Clear and transparent | Without choking throat |
| Example 14 | Clear and transparent | Without choking throat |
Therefore, the tobacco tar prepared from the nicotine benzoate prepared by the preparation method disclosed by the invention is clear and transparent in appearance, free of throat choking feeling and good in smoking experience.
Claims (10)
1. A method of preparing a synthetic nicotine salt, comprising the steps of:
(1) mixing synthetic nicotine raw material with propylene glycol and glycerol according to a certain weight ratio to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid;
(2) adding acid into the transparent liquid obtained in the step (1), heating and stirring, refluxing at 60-120 ℃ for 0.2-2h, and cooling to room temperature to obtain the synthetic nicotine salt.
2. The method of claim 1, wherein the propylene glycol in step (1) is 1, 2-propylene glycol or 1, 3-propylene glycol, and the glycerin is vegetable glycerin.
3. The method of making a synthetic nicotine salt of claim 2, wherein the propylene glycol is 1, 2-propylene glycol.
4. The method of preparing a synthetic nicotine salt of claim 1, wherein the weight ratio of synthetic nicotine to propylene glycol and glycerin is 1: 0.1-1: 0.1-1.
5. A process of preparing a synthetic nicotine salt according to claim 4, wherein the weight ratio of synthetic nicotine to propylene glycol, glycerol is preferably 1: 0.2-0.9: 0.2-0.9.
6. A process of preparing a synthetic nicotine salt according to claim 5, wherein the weight ratio of synthetic nicotine to propylene glycol, glycerol is more preferably 1: 0.2-0.4: 0.2-0.4.
7. The method of claim 1, wherein the acid of step (2) is benzoic acid, citric acid, malic acid, lactic acid, tartaric acid.
8. The method of preparing a synthetic nicotine salt according to claim 1, wherein the acid is used in step (2) in an amount of mixture a: acid =1: 0.1-1 (weight ratio).
9. The method of preparing a synthetic nicotine salt of claim 8, wherein the ratio of mixture a: acid =1:0.3-1 (weight ratio).
10. A tobacco tar composition, comprising a synthetic nicotine salt, propylene glycol, and glycerin, wherein the synthetic nicotine salt is prepared by the following method:
(1) mixing synthetic nicotine raw material with propylene glycol and glycerol according to a certain weight ratio to form a mixture A, fully stirring, and uniformly mixing to obtain transparent liquid;
(2) adding acid into the transparent liquid obtained in the step (1), heating and stirring, refluxing at 60-120 ℃ for 0.2-2h, and cooling to room temperature to obtain the synthetic nicotine salt.
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| CN113545510A (en) * | 2021-06-17 | 2021-10-26 | 深圳市博睿生物科技有限公司 | Nicotine salt, preparation method and application |
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| CN114868955B (en) * | 2022-05-09 | 2023-08-18 | 东莞市吉纯生物技术有限公司 | Nicotine salt preparation method, nicotine salt and aerosol product |
| CN114736188A (en) * | 2022-05-21 | 2022-07-12 | 南京科技职业学院 | Synthetic nicotine salt and preparation method thereof |
| CN114957208A (en) * | 2022-05-22 | 2022-08-30 | 南京科技职业学院 | Organic salt of nicotine and preparation method thereof |
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