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WO2016193755A1 - Procédé de récupération de terpènes à partir de matière végétale - Google Patents

Procédé de récupération de terpènes à partir de matière végétale Download PDF

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Publication number
WO2016193755A1
WO2016193755A1 PCT/GB2016/051651 GB2016051651W WO2016193755A1 WO 2016193755 A1 WO2016193755 A1 WO 2016193755A1 GB 2016051651 W GB2016051651 W GB 2016051651W WO 2016193755 A1 WO2016193755 A1 WO 2016193755A1
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WIPO (PCT)
Prior art keywords
biomass
reactor
terpenes
product
squalene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB2016/051651
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English (en)
Inventor
Jason ORNSTEIN
Yuan DAI
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Synshark LLC
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Synshark LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Synshark LLC filed Critical Synshark LLC
Publication of WO2016193755A1 publication Critical patent/WO2016193755A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241—Extraction of specific substances
    • 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
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • 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
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241—Extraction of specific substances
    • A24B15/243—Nicotine
    • 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
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/26—Use of organic solvents for extraction

Definitions

  • the invention relates to processes for the recovery or isolation of terpenes, such as squalene, from plant material and in particular from tobacco-derived plant material.
  • the processes may also include the isolation of alkaloids.
  • the invention also relates to associated processes and products.
  • biomass Biological material derived from living, or recently living, organisms is referred to as biomass and this material may contain a wide range of potentially useful components.
  • Fractionation is a very important process used industrially in order to isolate valuable components or constituents from biomass, such as that derived from tobacco.
  • Terpenes such as squalene, and alkaloids such as nicotine, are naturally produced in tobacco, but the ability to efficiently recover or isolate these high value products from the biomass determines their marketability. Further, as new processes are developed to genetically increase the production of terpenes and alkaloids, novel methods are needed to improve fractionation yields.
  • Squalene is widely found in marine animal oils as a trace component. It is suggested that the demand for squalene is the cause for livering' three to five million deep-water sharks a year. This number is expected to increase significantly as the preventative effect in many human diseases of squalene is further explored. Because of this, new sources for squalene such as plants are being developed. Tobacco is extensively farmed and could be a candidate for squalene production, but fractionation yields must be high to deliver cost competitive tobacco squalene. Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms.
  • Alkaloids are produced by a large variety of organisms including bacteria, fungi, plants, and animals and they have previously been purified from such sources by acid-base extraction. Alkaloids have a wide range of pharmacological activities including anti-malarial (e.g. quinine), anti-asthma (e.g. ephedrine), anti- cancer (e.g. homoharringtonine), cholinomimetic (e.g. galantamine), vasodilatory (e.g. vincamine), anti-arrhythmic (e.g. quinidine), analgesic (e.g. morphine), antibacterial (e.g. chelerythrine), and anti-hyperglycemic (e.g. piperine). Other alkaloids are well- known stimulants (e.g. caffeine and nicotine).
  • a process for isolating one or more terpenes from tobacco-derived biomass comprising: a)
  • the process comprises fractionation of the liquid product to isolate one or more terpenes. In some embodiments, the process comprises mechanical decomposition of the biomass by centrifugation, shaking or stirring of the biomass and the organic solvent in the reactor.
  • the pressure in the reactor is elevated compared to the ambient pressure outside the reactor.
  • the first temperature is between o°C and 350°C.
  • the biomass has a residence time within the reactor of less than 360 minutes.
  • the solvent is selected from the group consisting of: alcohols, supercritical fluids, hydrocarbons including volatile purified hydrocarbons, alkali metal salts including sodium hydroxide and potassium hydroxide, animal-derived fats and oils, vegetable-derived fats and oils, liquid carbon dioxide, water, acetone, and chloroform, and combinations thereof.
  • the solvent comprises water, hexane, supercritical carbon dioxide, supercritical methanol, or a combination of two or more thereof.
  • the process further comprises extracting oil from the solid product. In some embodiments, the process further comprises: d) introducing the solid product into a reactor with an organic solvent; e) further decomposing the solid product with the organic solvent at a second temperature; and f) recovering a second liquid product and a second solid product from the reactor, wherein the second liquid product contains additional terpene.
  • the process comprises fractionation of the second liquid product to isolate one or more terpenes.
  • the process comprises further treating the second solid product to isolate further terpene.
  • the liquid product contains greater than 0.05 wt % solids derived from the biomass.
  • the first temperature is between o°C and 150°C and the second temperature is between about o°C and 350°C.
  • the biomass is prepared by physically reducing the tobacco plant material.
  • the biomass is prepared by grinding the tobacco plant material.
  • the grinding may be mechanical grinding or cryogenic grinding.
  • the physical reduction of the plant material is carried out in the presence of one or more solvents.
  • the biomass is prepared by drying the tobacco plant material.
  • water or supercritical water is added as a facilitator for fractionation.
  • the terpene is a hemiterpene, monoterpene, sesquiterpene, diterpene, sesterterpene, triterpene, tetraterpene or polyterpene.
  • the terpene is a triterpene, for example, the terpene may be the linear triterpene squalene.
  • the process is a process for isolating one or more terpenes and one or more alkaloids from tobacco-derived biomass, the liquid product recovered from the reactor containing one or more terpenes and one or more alkaloids.
  • the process comprises fractionation of the liquid product to isolate one or more terpenes and/or one or more alkaloids.
  • the biomass is decomposed in an acidic or polar environment to optimize alkaloid recovery.
  • the biomass has a residence time within the reactor of up to 360 minutes to optimize terpene recovery.
  • the biomass has a residence time within the reactor of between 3 minutes and 720 minutes to optimize alkaloid recovery.
  • the alkaloid is selected from the group consisting of: a pyrrolidine, tropane, pyrrolizidine, piperidine, quinolizidine, indolizidine, pyridine, isoquinoline, oxazole, isoxazole, thiazole, quinazoline, acridine, quinoline, indole, imidazole, purine, ⁇ -phenylethylamine, colchicine, muscarine, benzylamine, putrescine, spermidine, sperine, peptide, diterpenes, and a steroid.
  • the alkaloid is a pyridine, selected from the group consisting of:
  • the alkaloid may be nicotine.
  • a process of manufacturing a product comprising a process of the first aspect of the invention, and further comprising isolating one or more terpenes from the liquid product and incorporating at least one of the isolated terpenes into the product.
  • the product is a cosmetic or pharmaceutical product.
  • a product manufactured according to a process of the second aspect of the invention there is provided a use of squalene obtained by a process according to the first aspect of the invention in a cosmetic or pharmaceutical product.
  • a use of nicotine obtained by a process as according to the first aspect of the invention in pharmaceuticals, supplements or smoking experiences there is provided.
  • Figure l is a flow diagram summarizing the process for isolating one or more terpenes from tobacco biomass according to an embodiment of the present invention.
  • Figure 2 is a GC-MS analysis run on GCMS-QP2010SE (Shimadzu) of a fractioned liquid produced in accordance with an embodiment of the process of the present invention set out in Example 1.
  • Figure 3 is a graph showing squalene yield from samples produced in accordance with an embodiment of the process of the present invention set out in Example 2, and a GC- MS analysis of a fractioned liquid.
  • Figure 4 is a graph showing squalene yield from samples produced in accordance with an embodiment of the process of the present invention set out in Example 3, and a GC- MS analysis of a fractioned liquid.
  • Figure 5 is a graph showing squalene yield from samples produced in accordance with an embodiment of the process of the present invention set out in Example 3, and a GC- MS analysis of a fractioned liquid.
  • Figure 6 is a graph showing squalene yield from samples produced in accordance with an embodiment of the process of the present invention set out in Example 4, and a GC- MS analysis of a fractioned liquid.
  • Figure 7 is a graph showing squalene yield from samples produced in accordance with an embodiment of the process of the present invention set out in Example 5, and a GC- MS analysis of a fractioned liquid.
  • Figure 8 is a graph showing squalene yield from samples produced in accordance with an embodiment of the process of the present invention set out in Example 6, and a GC- MS analysis of a fractioned liquid.
  • Fractionation is a separation process in which a mixture of components is divided during a phase transition into a number of fractions which are collected based on differences in a specific property of the individual components. Fractionation allows the isolation of multiple components in a mixture in a single run.
  • a typical protocol to isolate a pure chemical agent from natural origin is bioassay-guided fractionation, which involves the step-by-step separation of extracted components based on differences in their physicochemical properties, and assessing the biological activity, followed by next round of separation and assaying.
  • the starting material from which desired components including terpenes and alkaloids are to be isolated include biomass derived from plants. Suitable plants include tobacco. In some embodiments, plants are selected which are a good source of the desired components to be isolated. Plants may, for example, be bred to have high levels of the desired components and/or maybe genetically modified to have high levels of those components.
  • Biomass is organic matter derived from plants and it includes lignocellulosic biomass, for example, harvested plant matter such as leaf and stalk.
  • the biomass may be virgin biomass derived (directly) from plants, or it may be waste biomass, which is a low value by-product of biomass processing.
  • the biomass is tobacco- derived.
  • it comprises fresh, dried and/or cured leaves of a tobacco plant. For clarity, it is confirmed that seeds and oils extracted from plants, for example from their seeds, are not suitable for use as the biomass starting material in the processes of the present invention.
  • a process for recovering terpenes, and optionally alkaloids, from a tobacco-derived biomass including feeding the biomass and an organic solvent into a reactor, decomposing the biomass with organic solvent, or with an organic solvent and water or supercritical water, at a temperature between o°C and 350°C and recovering a liquid product and solid product from the reactor, wherein the liquid product contains at least one terpene.
  • the liquid product further includes one or more alkaloid.
  • the liquid product includes squalene and nicotine.
  • reactor is used to refer to a container or vessel within which the process occurs.
  • the reactor is an apparatus that allows the temperature or the pressure within it to be controlled and/ or adjusted.
  • the reactor is an apparatus that allows the contents to be agitated, for example by shaking, stirring, blending or milling.
  • a process for isolating one or more terpenes from tobacco-derived biomass comprising: a) introducing the biomass and an organic solvent into a vessel, b) physically reducing the biomass with the organic solvent at a first temperature, and c) recovering a liquid product and a solid product from the reactor, wherein the liquid product contains one or more terpenes.
  • the solvent may be added to the biomass after it has been physically reduced.
  • an additional step of physical reduction of the biomass and solvent may be carried out, or the mixture may be agitated, such as by shaking or stirring.
  • a process is provided for isolating one or more terpenes and/or one or more alkaloids from a biomass starting material.
  • the terpene to be isolated is squalene.
  • the alkaloid to be isolated is nicotine.
  • the objective is to develop a process which maximizes terpene, or terpene and alkaloid yield in liquid phase.
  • terpene specifically squalene
  • Processes according to the present invention may include one or more steps of treating the biomass to enhance removal of the terpenes from the biomass, referred to as "decomposition” or “decomposing” the plant material herein.
  • the biomass is treated to physically reduce the biomass, thereby disrupting the physical structure of the biomass.
  • the treatment may involve, for example, separating parts of the biomass and/or disrupting individual plant cells to access the interior of such cells. Such treatment may involve cutting, chopping, milling, grinding, crushing, blending, and the like.
  • the biomass may be physically reduced or decomposed by adjusting the pressure and/ or temperature.
  • the processes of the invention may also include a step of drying the biomass.
  • the biomass may be dried by any suitable method, including air drying, oven drying at elevated temperatures or freeze-drying. The drying step may be carried out prior to contacting the biomass with a solvent and before any decomposition step to further physically reduce the biomass.
  • Solvents suitable for use in the processes of the invention include those in which terpenes such as squalene are soluble.
  • the solvent is selective for terpenes, so that upon contact with the biomass, terpenes are solubilized whilst other components of the biomass are not solubilized or are solubilized to a lesser degree.
  • Suitable solvents include organic solvents. Solvents used may be selected from: alcohols including methanol, ethanol, propanol (such as 2-propanol);
  • supercritical fluids including supercritical carbon dioxide and supercritical methanol; hydrocarbons including volatile purified hydrocarbons such as petroleum ether and hexane; alkali metal salts including sodium hydroxide, potassium hydroxide; animal- derived fats and oils; vegetable-derived fats and oils; liquid carbon dioxide; water; acetone; and chloroform.
  • combinations of solvents may be used.
  • the solvent used may comprise a combination of supercritical carbon dioxide and an alcohol (such as ethanol or methanol) or a hydrocarbon solvent.
  • the treatment to physically reduce or decompose the biomass may be conducted in the presence of one or more solvents.
  • the biomass may be milled, chopped or blended in the presence of a solvent such as water, hexane or supercritical carbon dioxide. This results in a slurry of biomass from which terpenes may be separated, preferably from the liquid phase.
  • the process may, in some embodiments, include further steps to break down and/or remove unwanted constituents from the biomass or from an extract isolated from the biomass, for example the liquid phase.
  • Such steps may include, for example:
  • FIG. 1 is a flow diagram of a process for isolating one or more terpenes from a tobacco-derived biomass 1.
  • the biomass is subjected to physical reduction treatment. This step may comprise one or more of freeze-drying, grinding and drying.
  • the physically reduced biomass resulting from step 2 is next contacted with a solvent in step 3.
  • Suitable solvents include water, hydrocarbons such as hexane and supercritical fluids such as supercritical carbon dioxide, or combinations thereof.
  • the solvents can be used to extract oil from the biomass after physical reduction in step 2. Extraction can be performed using a reactor vessel, as a non-limiting example.
  • the combination of the physically reduced biomass and solvent may be subjected to further processing, as shown in step 4.
  • This processing may include adjusting the pressure within the reactor, adjusting the temperature within the reactor or agitation, such as stirring, blending or otherwise creating turbulence within the slurry comprising the physically reduced biomass and solvent.
  • the liquid phase and solid phase of the slurry are separated after the extraction in step 5, with the liquid phase being terpene oil 6 which can be used as a cosmetic or pharmaceutical precursor.
  • the solid phase is a wet cake which can be used as bio char or which can optionally undergo further processing to extract more terpenes or other components.
  • alkaloids present in tobacco biomass with terpenes are alkaloids. It improves the economic feasibility of tobacco terpene production if alkaloids, specifically nicotine, are also recovered in the fraction process. The nicotine oil market is growing in response to the shift towards electronic and other alternative smoking experiences.
  • compositional analysis on the flow through (2 mL) was performed and the results are shown in Figure 2.
  • One microliter of sample was injected into the GC-MS using an AOC-201 auto-sampler in 10:1 split mode (injector 28o°C) onto a ZB-5MS1 fused silica capillary column (30 m x 0.25 mm x 0.25 ⁇ thickness).
  • the initial oven temperature was 40°C, which was ramped to 120°C at 20°C/min, then ramped to 200°C at 6°C/min, then ramped to 26o°C at 20°C/min, and finally ramped to 3io°C for 3 min at 5°C/min.
  • Helium was used as the carrier gas.
  • the ion source was set to 230°C and the interface was 28o°C.
  • Squalene quantification was performed using selected ions. Peak identification of the compound was performed using direct comparison of the sample mass chromatogram with those of commercially available standard compounds. The quantitative calculations of squalene concentration were based on the peak area ratios relative to those of the standard.
  • Example 2 In a further set of experiments, tobacco leaves (8.35 g) were dried in an oven at 65.6°C (i50°F) for different time periods. The drying times are listed in Table 2.
  • the biomass had reached a stable weight after six hours in the oven. It was therefore concluded that fresh tobacco leaves could be dried in 6 hours in an oven at 65.6°C, and that longer drying periods provided no additional benefit.
  • the drying time will vary under different experiment conditions, such as drying temperature, amount of leaves and capacity of the oven.
  • the squalene yields are shown in the graph of Figure 3.
  • the black bars represent the squalene yield from the fresh leaf samples
  • the grey bars represent the squalene yield from the samples of dried tobacco leaves.
  • the amounts of squalene are provided as g of squalene per g of Fresh Weight (FW) leaf and the dry weight was converted to fresh weight for dried samples according to the dry weight vs fresh weight ratio to facilitate the comparison of squalene amounts between the treatment and control.
  • tobacco leaves (10 g) were blended in a household blender with hexane at different volumes for ⁇ minute.
  • the volume of hexane used is listed in Table 3.
  • Example 1 The blended tobacco leaves were centrifuged at 4000 rpm and the supernatant was loaded onto a silica column and the extracted squalene was analyzed as described in Example 1. As a comparison, 0.5 g samples of fresh leaf were prepared in liquid nitrogen as described in Example 1 and were also analyzed using the standard protocol.
  • the squalene yields are shown in the graph of Figure 4.
  • the black bars (Samples 1 to 3) represent the squalene yield from the fresh leaf samples, and the grey bars (Samples 4 to 6) represent the squalene yield from the leaf which had been blended for 1 minute with 60 ml hexane (6: 1 ratio).
  • the effects of reducing the amount of hexane used in wet milling extraction were also assessed and the results are shown in Figure 5.
  • the black bars (Samples 1 to 3) show the squalene yield from fresh leaf samples measured using the standard protocol
  • the grey bars show the squalene yield from samples blended with hexane in a ratio of 3:1 (30 ml hexane for 10 g of tobacco leaf)
  • the white bars show the squalene yield from samples blended with hexane in a ratio of 2:1 (20 ml hexane for 10 g of tobacco leaf).
  • the squalene extraction efficiency was not affected by reducing the volume of hexane used.
  • the hexane amount used for wet milling could be reduced to 2 ml per gram tobacco leaf without adversely affecting the squalene yield.
  • tobacco leaves (10.5 g) were blended with 21 mL water in a household blender for 1 minute. Samples of approximately 3 to 4 g of blended tobacco leaves were withdrawn at different times after blending (o, 0.5, 1, 2, 3, 4, 6, 24 hours).
  • the aqueous blends of tobacco leaf provide one physical format to process the leaf for downstream extraction process.
  • the aqueous blends enable efficient size expansion of the biomass and facilitate extraction process that requires biomass particle to exceed certain diameters.
  • the squalene yields are shown in the graph of Figure 7.
  • the black bars represent the squalene yield from the fresh leaf samples prepared using the standard method as set out in Example 1, and the grey bars (Samples 4 to 6) represent the squalene yield from the samples of wet milled dried tobacco sample. Because the yields are similar, the efficiency of wet milling method for dried tobacco leaf is similar with the standard squalene extraction method.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé d'isolation d'un ou de plusieurs terpènes à partir de biomasse dérivée de tabac, le procédé comprenant l'introduction de la biomasse et d'un solvant organique dans un réacteur, la décomposition de la biomasse avec le solvant organique à une première température, et la récupération d'un produit liquide et d'un produit solide dans le réacteur, le produit liquide contenant un ou plusieurs terpènes. L'invention concerne aussi des procédés et des produits associés.
PCT/GB2016/051651 2015-06-04 2016-06-03 Procédé de récupération de terpènes à partir de matière végétale Ceased WO2016193755A1 (fr)

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US62/171,121 2015-06-04

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Cited By (4)

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JP2018095619A (ja) * 2016-12-15 2018-06-21 三菱重工環境・化学エンジニアリング株式会社 ジテルペン及びステロイドの回収方法、ジテルペン及びステロイドの回収システム
CN108516923A (zh) * 2018-05-22 2018-09-11 天津汉荣生物技术有限公司 一系列烯萜类化合物及其制备方法和应用
CN111671130A (zh) * 2020-05-22 2020-09-18 深圳市德森生物科技有限公司 一种具有槟榔功效的电子烟油及其制备方法
CN113812668A (zh) * 2021-09-27 2021-12-21 浙江中烟工业有限责任公司 一种烟叶干馏提取精馏致香物的方法

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JP2018095619A (ja) * 2016-12-15 2018-06-21 三菱重工環境・化学エンジニアリング株式会社 ジテルペン及びステロイドの回収方法、ジテルペン及びステロイドの回収システム
CN108516923A (zh) * 2018-05-22 2018-09-11 天津汉荣生物技术有限公司 一系列烯萜类化合物及其制备方法和应用
CN111671130A (zh) * 2020-05-22 2020-09-18 深圳市德森生物科技有限公司 一种具有槟榔功效的电子烟油及其制备方法
CN113812668A (zh) * 2021-09-27 2021-12-21 浙江中烟工业有限责任公司 一种烟叶干馏提取精馏致香物的方法

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