CN110903277A - Method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation - Google Patents

Method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation Download PDF

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Publication number
CN110903277A
CN110903277A CN201811083549.6A CN201811083549A CN110903277A CN 110903277 A CN110903277 A CN 110903277A CN 201811083549 A CN201811083549 A CN 201811083549A CN 110903277 A CN110903277 A CN 110903277A
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nicotine
extracting
tobacco
tobacco leaves
petroleum ether
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解克伟
孙建阁
候文军
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Henan Yuancui Biotechnology Co Ltd
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Henan Yuancui Biotechnology Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74Separation; Purification; Use of additives, e.g. for stabilisation

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  • Organic Chemistry (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

The invention discloses a method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation, which comprises the following steps: (1) crushing tobacco leaves, adding alkaline water, and performing ultrasonic saponification; (2) vacuum distilling under reduced pressure to obtain nicotine distillate; (3) extracting with 2-3 times of petroleum ether at 60-90 deg.C, and recovering petroleum ether to obtain high-purity nicotine; (4) and (4) continuously extracting the solanesol from the tobacco residue after extraction. The method disclosed by the invention has the advantages that the pertinence is strong, the process is stable, the efficiency is high, the cost is low, the solvent is recycled by the technology, no waste liquid is discharged, the method is a green production technology which is beneficial to environmental protection, and the method is suitable for industrial mass production. The nicotine is extracted from the waste tobacco leaves, so that the waste is changed into valuable, and the method has good economic benefit, social benefit and environmental benefit.

Description

Method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation
Technical Field
The invention relates to a method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation, which is applied to the extraction of nicotine from waste tobacco leaves and can also be used as pretreatment before solanesol is extracted from the tobacco leaves, and belongs to the field of tobacco chemistry.
Background
Nicotine (commonly known as nicotine) is 1-methyl-2- (3-pyridyl) pyrrolidine, which belongs to a special alkaloid contained in natural tobacco leaves. Because nicotine is unstable (can be stored in a vacuum, sealed and dark state), nicotine sulfate is usually prepared by absorption of dilute sulfuric acid in industrial production. The nicotine can be widely applied to the fields of fine chemical industry, pharmacy, organic synthesis, national defense industry, agriculture and the like. The 40% nicotine sulfate can be used to prepare high-efficiency pesticide and biological pesticide without residue and public nuisance for grain, oil, vegetable, fruit, etc. In recent years, high purity natural nicotine has begun to be applied to the development of some high tech products. For example, in the pharmaceutical industry, it is used to develop drugs for treating cardiovascular diseases, skin diseases, snake venom diseases, insect bite, undefined lump, etc.; the nicotine citrate prepared from nicotine is also a main component for producing high-grade cigarette quality modifiers. With the rapid expansion of the field of application of nicotine products, the demand for natural nicotine in the market is increasing.
The current situation of tobacco waste: the planting area and the yield of tobacco plants in China all live at the first place in the world, tobacco planting and product processing play an important role in national economic development, and tobacco only occupies the sixth place next to rice, wheat, cotton, soybeans and corns in the income of agricultural products in China. At present, tobacco planted at home and abroad is mainly used as cigarettes. As a big country for tobacco production, the yield of tobacco leaves in China is 500 ten thousand tons every year, and about 25 percent of leftovers such as tobacco leaves, tobacco leaves and the like are discarded and cannot be used for cigarette production. If the tobacco is subjected to resource utilization, not only can natural chemical raw materials meeting the green and sanitary standards be obtained, a sustainable development opportunity is provided for the excavation and transformation of enterprises, but also the possible harmfulness of the waste tobacco to the change of soil texture and soil structure can be reduced, and the pollution of harmful ingredients to underground water is avoided. Therefore, the comprehensive utilization of the waste tobacco is enhanced, so that the waste is changed into precious resources, the economic income of tobacco growers can be increased, and the policy of recycling the solid waste in China is met.
The ultrasonic technology is to extract biological effective components by increasing the movement speed of medium molecules and the penetrating power of a medium by utilizing the mechanical effect, the cavitation effect and the thermal effect of ultrasonic waves. The ultrasonic wave can also generate a plurality of secondary effects, such as emulsification, diffusion, crushing, chemical effects and the like, which also promote the dissolution of the effective components in the plant body, promote the target effective components to enter the medium and be fully mixed with the medium, accelerate the extraction process and improve the extraction rate of the target effective components.
The invention discloses a production process of a CN1064680A nicotine salt and a pure nicotine product, and relates to a method for extracting nicotine from tobacco.
The invention discloses a method for extracting nicotine from tobacco, and discloses a method for extracting nicotine from tobacco, which comprises the steps of mixing tobacco raw materials with dilute sulfuric acid, crushing, rolling, adding a mixture of alkali and an organic solvent for impregnation, heating, filtering, extracting with the organic solvent, and then separating to obtain nicotine sulfate, natural nicotine, protein and spice.
The invention discloses a publication number CN102241565A, relates to the field of natural product chemistry, and particularly relates to a method for synchronously extracting solanesol and nicotine from tobacco. The invention relates to a method for extracting solanesol and nicotine from tobacco leaves, which comprises the following process flows: crushing tobacco leaves, mixing the crushed tobacco leaves with 0.5-4% sodium hydroxide solution according to the mass ratio of 1: 4-1: 15, then adding n-hexane or No. 6 solvent oil according to the mass ratio of 1: 0.6-1: 2 of the sodium hydroxide solution, carrying out reflux extraction for 1-3 hours, stopping heating, filtering the extract by using 100-200-mesh filter cloth, standing and layering the filtrate, separating out an upper n-hexane or No. 6 solvent oil phase, then extracting by using 2-12% hydrochloric acid, concentrating the n-hexane or No. 6 solvent oil phase to form a paste, wherein the paste is a solanesol crude extract, and the water phase is a crude hydrochloric acid nicotine solution.
The invention discloses a method for simultaneously extracting and separating solanesol and nicotine from tobacco, which comprises the following steps: (1) simultaneously extracting the solanesol and the nicotine; (2) extracting and separating; (3) separating and purifying the solanesol; (4) and (4) separating and purifying nicotine. The method of the invention can simultaneously carry out the dissociation and extraction of nicotine and the saponification and extraction of solanesol, thereby greatly simplifying the extraction steps and saving the time and the solvent consumption.
Chinese patent publication No. CN104086425A describes a method for simultaneously extracting and separating tobacco chlorogenic acid, solanesol, alkaloid and rutin, which comprises the steps of: step one, simultaneous extraction: crushing the tobacco raw material, extracting once by using 80% ethanol under the conditions of temperature of 40-50 ℃, ultrasonic frequency of 45KHz and material-liquid ratio of 10: 1, and after suction filtration or centrifugation, extracting the residues once by using 80% ethanol and 95% ethanol respectively; mixing the three extractive solutions to obtain crude extractive solutions of tobacco chlorogenic acid, solanesol, nicotine and rutin, wherein the extraction rates of tobacco chlorogenic acid, solanesol, nicotine and rutin are all 100%; step two, separation: separating the solanesol; separating chlorogenic acid and rutin; isolating the nicotine. The method realizes the simultaneous high-efficiency extraction of the chlorogenic acid, the solanesol, the nicotine and the rutin in the tobacco, the extraction rate reaches 100 percent, and the four are effectively separated by simple steps.
The above-mentioned invention patents have some drawbacks:
1. nicotine contains organic solvent residues, particularly residues of the toxic organic solvent chloroform;
2. the pollution to the environment and the harm to the health of operators are easy to cause;
3. the organic solvent directly extracts the nicotine water solution, so the emulsification is easy, the extraction efficiency is low, and the color value of the nicotine product is higher;
4. the loss of the organic solvent is large, and the production cost is improved.
The invention aims at the technical defect of extracting nicotine from tobacco, adopts alkaline water ultrasonic saponification hydrolysis, solid-liquid separation, reduced pressure distillation of liquid part, repeated extraction by using petroleum ether and petroleum ether recovery to obtain high-purity nicotine, and can also be used for pretreatment of tobacco leaves by extracting solanesol from the tobacco leaves.
In order to achieve the purpose, the invention adopts the technical scheme that: a method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation comprises the following steps:
1. pulverizing tobacco leaf into coarse powder, or adding 5% NaOH solution into tobacco residue from chlorogenic acid extraction, performing saponification at 60 deg.C for 45 min at a solid-liquid ratio of 1: 5-10, and press-filtering with plate-and-frame filter press to obtain liquid and solid;
2. vacuum distilling the filtrate obtained in the step 1 under reduced pressure to obtain colorless transparent distillate containing nicotine;
3. adding petroleum ether into the distillate obtained in the step 2 according to the proportion of 1: 2, stirring and extracting for 2-3 times, combining the petroleum ether extract, recovering the petroleum ether to obtain nicotine, and repeatedly recycling the petroleum ether;
4. returning the wastewater extracted in the step 3 to the step 1 to prepare a 5% NaOH solution for repeated recycling;
5. transferring the solid obtained in the step 1 into solanesol for extraction.
The invention has the beneficial effects that: the ultrasonic saponification hydrolysis is characterized by short reaction time and complete and sufficient reaction, on one hand, nicotine is fully dissociated from a salt state to facilitate distillation, on the other hand, solanesol ester components are saponified and hydrolyzed to dissociate the solanesol components to facilitate the next step of solanesol extraction, so that the ultrasonic saponification hydrolysis technology has the advantages of two purposes, water, alkali and petroleum ether are repeatedly utilized in the production process, no environmental pollution, high production efficiency of reduced pressure distillation and energy conservation; sulfuric acid and toxic organic solvent are not used for extraction in the production, and the product quality is high. The technology firstly extracts nicotine in the waste tobacco leaves, not only fully utilizes the resources of the tobacco leaves, but also performs primary pretreatment on the solanesol extracted from the tobacco leaves, reduces the quality of polar components, is beneficial to the extraction and purification of the solanesol in the next step, and is convenient for industrial mass production.
Drawings
FIG. 1 is a process flow diagram of a method for ultrasonically saponifying and hydrolyzing tobacco leaves by alkaline water and extracting nicotine by reduced pressure distillation.
Figure 2 shows the HPLC fingerprint of nicotine in vacuum distillate under reduced pressure, figure 3 shows the HPLC fingerprint of nicotine in liquid after extracting the distillate with petroleum ether, and the extraction rate of petroleum ether reaches 92% by comparison.
FIG. 4 shows the HPLC detection spectrum of high purity nicotine product, with the content reaching 98%.
Detailed Description
The practice examples of the present invention are used to further illustrate the essence of the present invention, but the present invention is not limited thereto.
The nicotine determination method comprises the following steps: high pressure liquid phase shimadzu LC-15C, column using thermo C18 silica gel column (5.0 μm, 4.6mm i.d. × 250cm), mobile phase: methanol to 0.3% phosphoric acid water 65: 35, wavelength: 260nm, flow rate: 1mL/min, sample size: 20uL, temperature: 35 degrees.
The detection method of the solanesol comprises the following steps: high pressure liquid phase shimadzu LC-15C, column using a thermo C18 silica gel column (5.0 μm, 4.6mm i.d. × 250cm), mobile phase acetonitrile/isopropanol 13: 7, wavelength: 210nm, flow rate: 1mL/min, sample size: 20uL, column temperature: at 30 ℃.
Example 1
1. Crushing tobacco leaves into coarse powder, or adding 60 kg of extracted chlorogenic acid tobacco leaves into 400 kg of 5% NaOH solution at the temperature of 60 ℃, carrying out ultrasonic treatment for 45 minutes, and carrying out filter pressing by using a plate-and-frame filter press to obtain 320 kg of liquid and a solid part;
2. carrying out vacuum reduced pressure distillation on the filtrate obtained in the step 1, and collecting 160 kg of colorless transparent distillate containing nicotine;
3. adding the distillate obtained in the step 2 into 320 liters of petroleum ether (60-90 ℃) according to the proportion of 1: 2, stirring and extracting for 2-3 times, combining petroleum ether extract liquor, recovering the petroleum ether to obtain 0.92 liters of nicotine, and repeatedly recycling the petroleum ether;
4. drying the solid part obtained by the plate-and-frame filter press in the step 1, and extracting the solanesol;
5. determining the concentration of the alkali liquor, supplementing insufficient decrement, and continuously recycling the alkali liquor as the alkaline hydrolysis liquid for reuse;
6. and (4) returning the water extracted in the step (3) to the step (1) for preparing alkali liquor.
Example 2
1. Pulverizing tobacco leaf into coarse powder, or extracting chlorogenic acid from tobacco leaf 60 kg, adding 5% Na2CO3400 kg of solution is added, the temperature is 60 ℃,performing ultrasonic treatment for 60 minutes, and performing pressure filtration by using a plate-and-frame filter press to obtain 320 kg of liquid and a solid part;
2. carrying out vacuum reduced pressure distillation on the filtrate obtained in the step 1, and collecting 160 kg of colorless transparent distillate containing nicotine;
3. and (3) adding the distillate obtained in the step (2) into 320 liters of petroleum ether (60-90 ℃) according to the proportion of 1: 2, stirring and extracting for 2-3 times, combining petroleum ether extract liquor, recovering the petroleum ether to obtain 0.89 liter of nicotine, and repeatedly recycling the petroleum ether.
4. Drying the solid part obtained by the plate-and-frame filter press in the step 1, and extracting the solanesol;
5. determining the concentration of the alkali liquor, supplementing insufficient decrement, and continuously recycling the alkali liquor as the alkaline hydrolysis liquid for reuse;
6. and (4) returning the water extracted in the step (3) to the step (1) for preparing alkali liquor.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.

Claims (8)

1. A method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation is characterized by comprising the following preparation steps:
(1) crushing waste tobacco leaves into coarse powder, extracting chlorogenic acid, adding alkaline water at the temperature of 55-60 ℃, saponifying and hydrolyzing for 60 minutes by ultrasonic oscillation, and performing plate-frame filter pressing and filter pressing to obtain nicotine extracting solution;
(2) and (2) carrying out vacuum reduced pressure concentration on the nicotine extracting solution obtained in the step (1) to obtain nicotine distillate.
2. Extracting the nicotine distillate obtained in the step (2) with petroleum ether with a boiling point of 60-90 ℃ for 3 times, wherein the liquid-liquid ratio of each time is 1: 2.
3. And (4) concentrating the petroleum ether extract obtained in the step (3) until no petroleum ether residue exists, so as to obtain the high-purity nicotine.
4. The method according to claim 1, wherein (1) the tobacco leaves are subjected to direct ultrasonic saponification reaction, the concentration of NaOH is 0.5-5%, the ultrasonic treatment time is 10-90 minutes, and the temperature is 40-60 ℃.
5. The method according to claim 1, wherein the base of (1) is NaOH, KOH, Na2CO3、CaO。
6. The process of claim 1, wherein the vacuum distillation of (2).
7. The method according to claim 1, wherein the extraction of (3) is carried out with petroleum ether having a boiling point of 60 to 90 ℃.
8. The method is also suitable for pretreatment of tobacco by extracting solanesol from tobacco.
CN201811083549.6A 2018-09-18 2018-09-18 Method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation Pending CN110903277A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114534361A (en) * 2021-12-31 2022-05-27 南阳理工学院 Method for combined extraction of essential oil, nicotine and extract from waste and inferior tobacco leaves
CN114698867A (en) * 2022-04-08 2022-07-05 贵州黄果树金叶科技有限公司 Preparation method of reconstituted tobacco with accurate components and reconstituted tobacco

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Publication number Priority date Publication date Assignee Title
CN1944425A (en) * 2006-08-11 2007-04-11 三明华健生物工程有限公司 High effective simultanuous clean extraction of high purity solanesol and nicotine
CN102241565A (en) * 2011-05-04 2011-11-16 东北林业大学 Method for synchronously extracting solanesol and nicotine from tobacco
CN103342628A (en) * 2013-07-26 2013-10-09 湖北中烟工业有限责任公司 Method for simultaneously extracting and separating solanesol and nicotine from tobacco
CN104072479A (en) * 2014-06-16 2014-10-01 南京泽朗医药科技有限公司 Method for extracting nicotine with synergy of enzymolysis and continuous counter-current ultrasonic extraction
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CN104725351A (en) * 2015-02-15 2015-06-24 洛阳市甘霖生物技术有限公司 Method of extracting high-purity nicotine from waste tobacco
CN105111184A (en) * 2015-09-24 2015-12-02 恩施和诺生物工程有限责任公司 Preparation method of high-purity nicotine
CN105566288A (en) * 2014-10-14 2016-05-11 北京本草通汇科技中心 High purity nicotine industrial preparation method
CN105985315A (en) * 2015-02-06 2016-10-05 杨晓林 Method for extracting nicotine from tobacco waste

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Publication number Priority date Publication date Assignee Title
CN1944425A (en) * 2006-08-11 2007-04-11 三明华健生物工程有限公司 High effective simultanuous clean extraction of high purity solanesol and nicotine
CN102241565A (en) * 2011-05-04 2011-11-16 东北林业大学 Method for synchronously extracting solanesol and nicotine from tobacco
CN103342628A (en) * 2013-07-26 2013-10-09 湖北中烟工业有限责任公司 Method for simultaneously extracting and separating solanesol and nicotine from tobacco
CN104072479A (en) * 2014-06-16 2014-10-01 南京泽朗医药科技有限公司 Method for extracting nicotine with synergy of enzymolysis and continuous counter-current ultrasonic extraction
CN104326912A (en) * 2014-07-25 2015-02-04 湖北中烟工业有限责任公司 Separation method of effective components from tobacco
CN104086425A (en) * 2014-07-30 2014-10-08 中国农业科学院烟草研究所 Method for simultaneously extracting and separating chlorogenic acid, solanesol, alkaloid and rutin in tobacco
CN105566288A (en) * 2014-10-14 2016-05-11 北京本草通汇科技中心 High purity nicotine industrial preparation method
CN105985315A (en) * 2015-02-06 2016-10-05 杨晓林 Method for extracting nicotine from tobacco waste
CN104725351A (en) * 2015-02-15 2015-06-24 洛阳市甘霖生物技术有限公司 Method of extracting high-purity nicotine from waste tobacco
CN105111184A (en) * 2015-09-24 2015-12-02 恩施和诺生物工程有限责任公司 Preparation method of high-purity nicotine

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114534361A (en) * 2021-12-31 2022-05-27 南阳理工学院 Method for combined extraction of essential oil, nicotine and extract from waste and inferior tobacco leaves
CN114698867A (en) * 2022-04-08 2022-07-05 贵州黄果树金叶科技有限公司 Preparation method of reconstituted tobacco with accurate components and reconstituted tobacco
CN114698867B (en) * 2022-04-08 2023-03-03 贵州黄果树金叶科技有限公司 Preparation method of reconstituted tobacco with accurate components and reconstituted tobacco

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