Acoarecoline tartrate solid salt as well as preparation method and application thereof

Abstract

The invention discloses arecoline tartrate solid salt as well as a preparation method and application thereof. The preparation method comprises the following preparation steps: S10, adding tartaric acid into a first solvent, heating and stirring to obtain a tartaric acid solution; s20, adding the arecoline solution into the tartaric acid solution, and uniformly stirring and mixing to obtain a salt solution; s30, adding a second solvent into the salt solution, uniformly stirring and mixing, and heating for reaction to obtain a solid-liquid mixture; s40, adding a third solvent into the solid-liquid mixture, and pulping to obtain slurry; and S50, washing and filtering the slurry with a fourth solvent to obtain a filter cake, and carrying out vacuum drying on the filter cake to obtain the arecoline tartrate solid salt. According to the technical scheme, the arecoline tartrate solid salt is prepared through a simple process, the stability of arecoline can be improved, so that in further application of buccal tobacco products, arecoline is uniformly, slowly and durably released in the oral cavity, long-acting and mild physiological satisfaction is provided for consumers, and meanwhile irritation to digestive tracts can be reduced.

Description

Technical Field

[0001] The present application relates to the technical field of oral cigarettes, and in particular to a solid salt of arecoline tartrate, a preparation method and an application thereof. Background Art

[0002] Arecoline is an alkaloid similar to nicotine. It can bring similar physiological satisfaction and pleasure to nicotine during chewing. It is an important component of oral tobacco products such as snus. Currently, arecoline used in oral tobacco products mostly exists in the form of betel nut extract, free arecoline, liquid arecoline salt, etc. However, betel nut extract has complex ingredients, strong odor, and poor taste; free arecoline has poor stability, strong irritation, and poor taste; and liquid arecoline salt has shortcomings such as too fast arecoline release rate, too much strength in the early stage of oral holding and less strength in the later stage, and the taste quickly fades during the entire oral holding process.

[0003] Therefore, it is very necessary to improve the release effect and taste of arecoline in the oral cavity and provide consumers with long-lasting and peaceful physiological satisfaction. Summary of the invention

[0004] The present application provides a solid salt of arecoline tartrate, a preparation method and an application thereof, aiming to solve the problem in the prior art that arecoline has an overly fast release rate and poor taste in the human oral cavity.

[0005] To achieve the above object, the present application proposes a method for preparing a solid salt of arecoline tartrate. The preparation method comprises the following preparation steps:

[0006] S10, adding tartaric acid to the first solvent, heating and stirring, to obtain a tartaric acid solution;

[0007] S20, adding the arecoline solution to the tartaric acid solution, stirring and mixing to obtain a salt solution;

[0008] S30, adding a second solvent to the salt solution, stirring and mixing, and heating to react to obtain a solid-liquid mixture;

[0009] S40, adding a third solvent to the solid-liquid mixture, and performing beating operation to obtain a slurry;

[0010] S50, washing and filtering the slurry with a fourth solvent to obtain a filter cake, and vacuum drying the filter cake to obtain a solid salt of arecoline tartrate.

[0011] In some embodiments, in step S10, the mass ratio of the tartaric acid to the first solvent is 1:3-8;

[0012] Wherein, the tartaric acid is one of L-tartaric acid, DL-tartaric acid and D-tartaric acid; the first solvent is at least one of ethanol, isopropanol, ethyl acetate and ultrapure water.

[0013] In some embodiments, in step S10, the heating temperature is 40-70°C, the stirring speed is 800-1500 RPM, and the heating time is 10-60 min.

[0014] In some embodiments, in step S20, the molar ratio of arecoline in the arecoline solution to tartaric acid in the tartaric acid solution is 1:1.2-1.7.

[0015] In some embodiments, in step S30, the mass ratio of the second solvent to the first solvent is 0.1 to 0.3:1;

[0016] Wherein, the second solvent is at least one of petroleum ether, ethyl acetate and ultrapure water.

[0017] In some embodiments, in step S30, the heating temperature is 40-70° C., and the heating reaction time is 3-5 hours.

[0018] In some embodiments, in step S40, the mass ratio of the third solvent to the first solvent is 0.2 to 0.6:1;

[0019] Wherein, the third solvent is ethyl acetate.

[0020] In some embodiments, in step S50, the mass ratio of the fourth solvent to the first solvent is 0.5 to 1.5:1;

[0021] Wherein, the fourth solvent is ethyl acetate or petroleum ether; during the vacuum drying process, the vacuum drying temperature is 40-60° C., the vacuum degree is 0.5-0.8 MPa, and the drying time is 3-5 h.

[0022] The present application also proposes a solid salt of arecoline tartrate, which is prepared by the preparation method of the solid salt of arecoline tartrate as described above.

[0023] The present application also proposes a use of the solid salt of arecoline tartrate as described above in oral tobacco products.

[0024] The technical scheme of the present application proposes a solid salt of arecoline tartrate, a preparation method and an application. The preparation method comprises the following preparation steps: S10, adding tartaric acid to a first solvent, heating and stirring to obtain a tartaric acid solution; S20, adding an arecoline solution to the tartaric acid solution, stirring and mixing evenly to obtain a salt solution; S30, adding a second solvent to the salt solution, stirring and mixing evenly, and heating the reaction to obtain a solid-liquid mixture; S40, after adding a third solvent to the solid-liquid mixture, beating operation to obtain a slurry; S50, washing and filtering the slurry with a fourth solvent to obtain a filter cake, and vacuum drying the filter cake to obtain a solid salt of arecoline tartrate. The technical scheme of the present application prepares free arecoline and tartaric acid into a solid salt of arecoline tartrate through a simple process, which can improve the stability of arecoline, so that in the further application of oral tobacco products, arecoline can be released evenly, slowly and persistently in the oral cavity, providing consumers with a long-lasting and peaceful physiological satisfaction, while reducing the irritation to the digestive tract. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings required for use in the embodiments or the prior art descriptions are briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those of ordinary skill in the art, other drawings can be obtained based on these drawings without creative work, among which:

[0026] Figure 1 This is a schematic diagram of the preparation process of arecoline tartrate solid salt according to one embodiment of the present application;

[0027] Figure 2 Schematic diagram of the arecoline oral cigarette release curve corresponding to samples 1-4 tested in this application. DETAILED DESCRIPTION

[0028] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of this application.

[0029] See also Figure 1 As shown, the present application proposes a method for preparing a solid salt of arecoline tartrate. The preparation method comprises the following preparation steps:

[0030] Step S10, adding tartaric acid to the first solvent, heating and stirring to obtain a tartaric acid solution.

[0031] This step is intended to completely dissolve tartaric acid to form a uniform tartaric acid solution. In this step, tartaric acid is one of L-tartaric acid, DL-tartaric acid and D-tartaric acid, and all presents as colorless or white crystalline forms at normal temperature. The first solvent adopted has good solubility properties to tartaric acid, and the first solvent is at least one of ethanol, isopropanol, ethyl acetate and ultrapure water.

[0032] It is understandable that before tartaric acid is dissolved, it is necessary to proportion tartaric acid and the addition of the first solvent. In this step, the mass ratio of tartaric acid to the first solvent is 1: 3-8, i.e., 1 mass part of tartaric acid is matched with 3-8 mass parts of the first solvent, to balance the dissolution cost and dissolution effect. And after tartaric acid is added to the first solvent, the dissolution rate of tartaric acid can be increased by heating and stirring, and the heating and stirring parameters further set are: heating temperature 40-70°C, stirring speed 800-1500RPM, heating time 10-60min, and in actual operation, specific parameter selection can be determined according to the characteristics of the dissolution system.

[0033] Step S20, adding the arecoline solution to the tartaric acid solution, stirring and mixing to obtain a salt solution.

[0034] In this step, when the tartaric acid solution and the arecoline solution are mixed, the protons in the tartaric acid molecules will be accepted by the arecoline molecules to form ionic bonds, thereby generating the corresponding arecoline tartrate salt, and the solution obtained at this time is a salt solution.

[0035] Among them, the arecoline solution refers to a solution formed by dissolving arecoline in a solvent (such as water and ethanol). It is worth noting that during the addition process, the molar ratio of arecoline in the arecoline solution to tartaric acid in the tartaric acid solution is 1:1.2-1.7. By setting the molar ratio of arecoline to tartaric acid within this range, the yield of the product can be maximized while ensuring that the reaction is completely carried out.

[0036] Furthermore, the process of adding the arecoline solution to the tartaric acid solution should be slow, such as by dropwise addition, to control the reaction rate and prevent the reaction from being too violent and causing dangers, such as sudden heat release, gas release or precipitation. And stirring after the addition is completed can promote uniform mixing, so that the tartaric acid molecules and the arecoline molecules can fully contact and react.

[0037] Step S30, adding the second solvent to the salt solution, stirring and mixing, and heating for reaction to obtain a solid-liquid mixture.

[0038] In this step, the addition of the second solvent will change the solubility of the solute in the solution. Since the solubility of arecoline tartrate in the second solvent is significantly different from that in the first solvent, when the second solvent is added to the salt solution, the solubility of arecoline tartrate will decrease, thereby causing it to precipitate from the solution to form solid particles.

[0039] The mass ratio of the second solvent to the first solvent is 0.1 to 0.3:1, so as to provide sufficient solubility change and obtain higher product purity and reaction rate. The second solvent is at least one of petroleum ether, ethyl acetate and ultrapure water.

[0040] Furthermore, by heating the reaction, a solid-liquid mixture is gradually formed during the heating process as the solvent evaporates and the solubility of the solute changes. The heating temperature is 40 to 70° C. and the heating reaction time is 3 to 5 hours.

[0041] Step S40, adding a third solvent to the solid-liquid mixture, and performing a pulping operation to obtain a slurry.

[0042] In this step, the third solvent is ethyl acetate. By adding ethyl acetate, the solubility of each component in the solid-liquid mixture can be changed, thereby facilitating the precipitation and dispersion of the solid salt of arecoline tartrate, and facilitating the subsequent separation of the solid product from the mixture through filtering, washing, etc. The mass ratio of the third solvent to the first solvent is 0.2 to 0.6:1.

[0043] Step S50, using a fourth solvent to wash and filter the slurry to obtain a filter cake, and vacuum drying the filter cake to obtain a solid salt of arecoline tartrate.

[0044] In this step, the purpose is to remove impurities in the slurry by washing with the fourth solvent, and filter out the liquid part in the slurry to obtain a filter cake containing a solid product.

[0045] Among them, the selection of the fourth solvent should have high solubility for impurities in the slurry and low solubility for the solid salt of arecoline tartrate, such as ether or petroleum ether, and further control the mass ratio of the fourth solvent to the first solvent to be 0.5-1.5:1, to ensure that the fourth solvent can effectively wash the impurities in the slurry, while avoiding excessive solvents that cause difficulties in subsequent treatment. During the washing process, by fully stirring the slurry, it can be ensured that there is sufficient contact with the slurry, and then the filter cake containing the solid product is filtered; and then rapid drying is achieved at a lower temperature in a vacuum drying oven to avoid excessive drying and resulting in a decrease in the quality of the solid salt. Among them, the vacuum drying parameters are set as follows: vacuum drying temperature is 40-60°C, vacuum degree is 0.5-0.8MPa, and drying time is 3-5h.

[0046] Based on this, the present application uses the above simple process to make free arecoline and tartaric acid into a solid salt, thereby improving the stability and taste of arecoline, and improving the problems of strong irritation, poor taste, and too fast release in existing products. It provides consumers with long-lasting and peaceful physiological satisfaction and reduces irritation to the digestive tract.

[0047] Furthermore, the present application proposes a specific preparation example of arecoline tartrate solid salt, including:

[0048] Example 1

[0049] S10, dissolving 6.7 g of D-tartaric acid in 50.0 g of ethyl acetate, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0050] S20, slowly adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0051] S30, adding 10.0 g of ultrapure water to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0052] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0053] S50, using 50.0 g of ethyl acetate to wash the slurry and filter to obtain a filter cake, and the filter cake is dried at 45° C. in a vacuum to obtain a yellow powder solid, namely, D-arecoline tartrate solid salt.

[0054] The product of D-arecoline tartrate solid salt is 10.3 g, with a yield of 88.0%. The total arecoline content of the obtained yellow powder solid is 43.2% after testing.

[0055] Example 2

[0056] S10, dissolving 6.7 g of D-tartaric acid in 50.0 g of ethanol, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0057] S20, slowly adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0058] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0059] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0060] S50, using 50.0 g of ethyl acetate to wash the slurry and filter to obtain a filter cake, and the filter cake is dried at 45° C. in a vacuum to obtain a yellow powder solid, namely, D-arecoline tartrate solid salt.

[0061] The product of D-arecoline tartrate solid salt is 8.1 g, with a yield of 69.2%. The total arecoline content of the obtained yellow powder solid is 45.2% after testing.

[0062] Example 3

[0063] S10, dissolving 6.7 g of D-tartaric acid in 50.0 g of ultrapure water, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0064] S20, slowly adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0065] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0066] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0067] S50, using 50.0 g of ethyl acetate to wash the slurry and filter to obtain a filter cake, and the filter cake is dried at 45° C. in a vacuum to obtain a yellow powder solid, namely, D-arecoline tartrate solid salt.

[0068] The product of D-arecoline tartrate solid salt is 8.3 g, with a yield of 70.9%. The total arecoline content of the obtained yellow powder solid is 33.2% after testing.

[0069] Example 4

[0070] S10, dissolving 6.7 g of D-tartaric acid in 50.0 g of isopropanol, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0071] S20, slowly adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0072] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0073] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0074] S50, using 50.0 g of ethyl acetate to wash the slurry and filter to obtain a filter cake, and the filter cake is dried at 45° C. in a vacuum to obtain a yellow powder solid, namely, D-arecoline tartrate solid salt.

[0075] The product of D-arecoline tartrate solid salt is 8.3 g, with a yield of 71.0%. The total arecoline content of the obtained yellow powder solid is 43.2% after testing.

[0076] Example 5

[0077] S10, dissolving 6.3 g of L-tartaric acid in 50.0 g of isopropanol, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain an L-tartaric acid solution;

[0078] S20, slowly adding 5 g of the arecoline solution to the L-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0079] S30, adding 10.0 g of petroleum ether to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. and reacting for 4 hours to obtain a solid-liquid mixture;

[0080] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0081] S50, washing and filtering with 50.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a yellow powder solid, namely, L-arecoline tartrate solid salt.

[0082] The solid salt of L-arecoline tartrate was 9.7 g, with a yield of 85.8%. The total arecoline content of the yellow powder solid obtained was 39.2% after testing.

[0083] Example 6

[0084] S10, dissolving 6.7 g of D-tartaric acid in 40.0 g of isopropanol, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0085] S20, slowly dropwise adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0086] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0087] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0088] S50, washing and filtering with 50.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a yellow powder solid, namely, D-arecoline tartrate solid salt.

[0089] The solid salt of D-tartaric arecoline acid was 10.2 g, with a yield of 87.2%. The total arecoline content of the obtained yellow powder solid was 42.2% after testing.

[0090] Example 7

[0091] S10, dissolving 6.7 g of D-tartaric acid in a mixed solvent of 30.0 g of isopropanol and 5.0 g of ultrapure water, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0092] S20, slowly dropwise adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0093] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0094] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0095] S50, washing and filtering with 40.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a light yellow powder solid, namely, D-tartaric arecoline acid solid salt.

[0096] The solid salt of D-tartaric arecoline acid was 9.7 g, with a yield of 82.9%. The total arecoline content of the obtained light yellow solid powder was 48.1% after testing.

[0097] Example 8

[0098] S10, dissolving 6.7 g of D-tartaric acid in a mixed solvent of 30.0 g of isopropanol and 5.0 g of ultrapure water, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0099] S20, slowly dropwise adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0100] S30, adding 5.0 g of ultrapure water to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0101] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0102] S50, washing and filtering with 50.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a white powder solid, namely, D-tartaric arecoline acid solid salt.

[0103] The solid salt of D-tartaric arecoline acid was 10.9 g, with a yield of 93.1%. The total arecoline content of the obtained white powder solid was 44.3% after testing.

[0104] Example 9

[0105] S10, dissolving 6.7 g of D-tartaric acid in 40.0 g of isopropanol, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0106] S20, slowly dropwise adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0107] S30, adding a mixed solvent of 5.0 g ethyl acetate and 5.0 g ultrapure water to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0108] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0109] S50, washing and filtering with 50.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a yellow powder solid, namely, D-arecoline tartrate solid salt.

[0110] The solid salt of D-arecoline tartrate was 10.2 g, with a yield of 87.2%. The total arecoline content of the yellow powder solid obtained was 42.2% after testing.

[0111] Example 10

[0112] S10, dissolving 8.5 g of D-tartaric acid in 50.0 g of isopropanol, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0113] S20, slowly dropwise adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0114] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0115] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0116] S50, washing and filtering with 50.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a white powder solid, namely, D-arecoline tartrate solid salt.

[0117] The solid salt of D-arecoline tartrate was 10.6 g, with a yield of 77.4%. The total arecoline content of the obtained white powder solid was 45.2% after testing.

[0118] Embodiment 11

[0119] S10, dissolving 8.5 g of D-tartaric acid in 50.0 g of isopropanol, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0120] S20, slowly dropwise adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0121] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0122] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0123] S50, washing and filtering with 50.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a white powder solid, namely, D-arecoline tartrate solid salt.

[0124] The solid salt of D-arecoline tartrate was 8.9 g, with a yield of 76.1%. The total arecoline content of the obtained white powder solid was 35.9% after testing.

[0125] Example 12

[0126] S10, dissolving 6.7 g of D-tartaric acid in 20.0 g of ethyl acetate, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a DL-tartaric acid solution;

[0127] S20, slowly adding 5 g of the arecoline solution to the DL-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0128] S30, adding 10.0 g of ultrapure water to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0129] S40, adding 12.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0130] S50, using 10.0 g of petroleum ether to wash the slurry and filter to obtain a filter cake, and the filter cake is dried at 45° C. in a vacuum to obtain a yellow powder solid, namely, DL-arecoline tartrate solid salt.

[0131] The product of DL-tartrate arecoline solid salt is 9.3 g, with a yield of 79.5%. The total arecoline content of the obtained yellow powder solid is 44.1% after testing.

[0132] Comparative Example 1

[0133] S10, dissolving 9.7 g of D-tartaric acid in 50.0 g of methanol, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0134] S20, slowly dropwise adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0135] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0136] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0137] S50, washing and filtering with 50.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a yellow oily liquid, namely, arecoline-D-tartaric acid liquid salt.

[0138] The amount of arecoline-D-tartaric acid liquid salt was 10.0 g, and the yield was 63.0%. The total arecoline content of the yellow oily liquid obtained was 37.3% after testing, which was in line with the theoretical value range.

[0139] Comparative Example 2

[0140] S10, dissolving 9.7 g of D-tartaric acid in 50.0 g of acetonitrile, heating and stirring (50° C., 1200 RPM, 0.5 h) to obtain a D-tartaric acid solution;

[0141] S20, slowly dropwise adding 5 g of the arecoline solution to the D-tartaric acid solution obtained in step S10, stirring and mixing to obtain a salt solution;

[0142] S30, adding 10.0 g of ethyl acetate to the salt solution obtained in step S20, stirring and mixing evenly, heating to 50° C. to react for 4 hours, to obtain a solid-liquid mixture;

[0143] S40, adding 20.0 g of ethyl acetate to the solid-liquid mixture obtained in step S30, and beating for 30 minutes to obtain a slurry;

[0144] S50, washing and filtering with 50.0 g of ethyl acetate to obtain a filter cake, and drying the filter cake in vacuum at 45° C. to obtain a yellow oily liquid, namely, arecoline-D-tartaric acid liquid salt.

[0145] The amount of arecoline-D-tartaric acid liquid salt was 9.6 g, and the yield was 66.0%. The total arecoline content of the yellow oily liquid obtained was 34.2% after testing, which was in line with the theoretical value range.

[0146] The above are only some embodiments of the present application, and other implementations carried out within the parameter range proposed in the present application are within the protection scope of the present application. The arecoline tartrate salts obtained in Examples 1 to 12 and Comparative Examples 1 and 2 were weighed and subjected to material detection treatment to obtain the data in Table 1.

[0147] Table 1

[0148]

[0149] From the data in the above table, it can be concluded that arecoline has a high solubility in tartaric acid solution and is easy to generate arecoline tartrate salt, which makes the arecoline tartrate salt more stable during storage and less prone to discoloration caused by oxidation, volatilization or moisture absorption, thereby extending the shelf life of the arecoline salt.

[0150] The details are as follows:

[0151] 1. In combination with Examples 1 to 8, it can be seen that the arecoline tartrate salt obtained by adjusting the reaction by changing the type and addition amount of the first solvent and the second solvent has good stability, high yield, and high arecoline content. At the same time, the solid arecoline salt finally formed is more convenient to be used in the field of oral cigarettes, and the obtained taste meets the product requirements.

[0152] 2. Combining Examples 1 to 12 and Comparative Examples 1 to 2, it can be seen that the type of the first solvent in the reaction system has a great influence on the yield of the solid salt of arecoline tartrate. The arecoline salt obtained by adding a highly polar solvent such as methanol, acetonitrile, etc. is a liquid, while the addition of a less polar solvent such as isopropanol, ethyl acetate, ultrapure water, etc., obtains a solid arecoline salt.

[0153] 3. In combination with Example 4, Example 5, Example 8 and the comparative example, it can be seen that the mass ratio of arecoline and tartaric acid has a great influence on the yield of the solid salt, and increasing the addition amount of tartaric acid will reduce the yield of the arecoline solid salt.

[0154] 4. In combination with Example 7, Example 8 and Example 11, it can be seen that the type and amount of the second solvent used are also related to the color, yield and arecoline content of the arecoline solid salt. When a certain amount of ultrapure water is added to the reaction system, it can not only accelerate the dissolution of tartaric acid in the reaction system and shorten the reaction time, but also improve the properties of the arecoline tartrate solid salt product and increase the yield.

[0155] In order to more intuitively experience the taste and sustained-release performance of the prepared arecoline tartrate solid salt, oral tobacco products were prepared based on equal amounts of different arecoline sources (including the arecoline tartrate solid salt prepared in the present application, free arecoline, arecoline extract and arecoline liquid salt) for actual testing.

[0156] The preparation method of the oral tobacco product specifically comprises the following steps: 1) mixing a pH regulator, a sweetener, a cooling agent, a flavoring agent, an antioxidant and a filler, adding an appropriate amount of water and stirring for 2 hours to obtain a uniform mixed solution, and placing the mixed solution in an environment of 50°C for drying to obtain a powdered auxiliary material; 2) adding an arecoline source and a moisturizer into a container, stirring for 35 minutes to obtain a liquid main material; 3) adding the obtained auxiliary material to the obtained main material, stirring for 35 minutes to obtain a semi-wet powdered composition; 4) subjecting the obtained composition to microwave sterilization, aging for 24 hours after sterilization, and obtaining the oral tobacco; 5) wrapping the obtained oral tobacco with a nicotine bag made of food-grade non-woven fabric to obtain a finished product (0.8 g / bag) that can be placed in the oral cavity.

[0157] Then, the snus prepared from different arecoline sources were scored. For example, the snus prepared from solid salt of arecoline tartrate corresponds to sample 1; the snus prepared from free arecoline corresponds to sample 2; the snus prepared from arecoline extract corresponds to sample 3; and the snus prepared from liquid salt of arecoline tartrate corresponds to sample 4.

[0158] The actual measurement method adopted is: organize 40 snus experts to taste food samples, with each group of 10 experts conducting cross-tasting. Then remove the highest and lowest scores, calculate the average of the scores of the remaining 8 experts, and finally compare the total scores obtained.

[0159] Table 2 Sensory evaluation table of arecoline oral smoke

[0160]

[0161] Further referring to the national pharmacopoeia, artificial saliva was prepared and the pH of the artificial saliva was adjusted to 6.7. The snus corresponding to each test sample was added to 50 ml of artificial saliva with a pH value of 6.7, and then the entire sample was placed in a constant temperature shaker at 37°C to simulate human oral digestion in vitro. Samples were taken and tested according to the experimental design time to obtain the relationship between the sustained release degree of the arecoline sustained-release snus and time, and then the release curve of the arecoline sustained-release snus was prepared, such as Figure 2 shown.

[0162] Depend on Figure 2 It can be seen that the sample 1 of the present application releases arecoline slowly and evenly from the beginning to 24 minutes. In the sample 2-4, arecoline is completely released within 10 minutes, and it can be clearly seen that in the sample 2-4, the release of arecoline is uneven, with rapid release in the first 6 minutes and relatively slow release in the last 4 minutes. Combined with the sensory evaluation table of arecoline buccal cigarette in Table 2, it can be seen that arecoline tartrate solid salt can effectively improve the existing arecoline chewing products, such as strong irritation, poor taste, and too fast release, so as to ensure that the mouth can maintain a stable momentum for a long time, and can make arecoline uniformly, slowly, and persistently released in the oral cavity, providing consumers with a long-lasting and peaceful physiological satisfaction, while effectively reducing the irritation to the digestive tract.

[0163] The above description is only a partial or preferred embodiment of the present application. Neither the text nor the drawings can limit the scope of protection of the present application. All equivalent structural changes made using the contents of the present application specification and drawings under the overall concept of the present application, or direct / indirect application in other related technical fields are included in the scope of protection of the present application.

Claims

1. A method for preparing a solid salt of arecoline tartrate, characterized in that: The method comprises the following preparation steps: S10, adding tartaric acid to the first solvent, heating and stirring, to obtain a tartaric acid solution; S20, adding the arecoline solution to the tartaric acid solution, stirring and mixing to obtain a salt solution; S30, adding a second solvent to the salt solution, stirring and mixing, and heating to react to obtain a solid-liquid mixture; S40, adding a third solvent to the solid-liquid mixture, and performing beating operation to obtain a slurry; S50, washing and filtering the slurry with a fourth solvent to obtain a filter cake, and vacuum drying the filter cake to obtain a solid salt of arecoline tartrate.

2. The method for preparing the solid salt of arecoline tartrate according to claim 1, wherein In step S10, the mass ratio of the tartaric acid to the first solvent is 1:3-8; Wherein, the tartaric acid is one of L-tartaric acid, DL-tartaric acid and D-tartaric acid; the first solvent is at least one of ethanol, isopropanol, ethyl acetate and ultrapure water.

3. The preparation method of arecoline tartrate solid salt according to claim 2, characterized in that, In step S10, the heating temperature is 40-70°C, the stirring speed is 800-1500RPM, and the heating time is 10-60min.

4. The preparation method of arecoline tartrate solid salt according to claim 1, characterized in that, In step S20, the molar ratio of arecoline in the arecoline solution to tartaric acid in the tartaric acid solution is 1:1.2-1.

7.

5. The preparation method of arecoline tartrate solid salt according to claim 1, characterized in that, In step S30, the mass ratio of the second solvent to the first solvent is 0.1 to 0.3:1; Wherein, the second solvent is at least one of petroleum ether, ethyl acetate and ultrapure water.

6. The method for preparing the solid salt of arecoline tartrate according to claim 5, wherein In step S30, the heating temperature is 40-70°C, and the heating reaction time is 3-5 hours.

7. The method for preparing the solid salt of arecoline tartrate according to claim 1, wherein In step S40, the mass ratio of the third solvent to the first solvent is 0.2-0.6:1; Wherein, the third solvent is ethyl acetate.

8. The method for preparing the solid salt of arecoline tartrate according to claim 1, wherein In step S50, the mass ratio of the fourth solvent to the first solvent is 0.5-1.5:1; Wherein, the fourth solvent is ethyl acetate or petroleum ether; during the vacuum drying process, the vacuum drying temperature is 40-60° C., the vacuum degree is 0.5-0.8 MPa, and the drying time is 3-5 h.

9. A solid salt of arecoline tartrate, characterized in that: The solid salt of arecoline tartrate is prepared by the preparation method of the solid salt of arecoline tartrate as described in any one of claims 1 to 8.

10. Use of the solid salt of arecoline tartrate according to claim 9 in oral tobacco products.

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