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WO2008138084A2 - Procédé d'enrichissement du safrole - Google Patents

Procédé d'enrichissement du safrole Download PDF

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Publication number
WO2008138084A2
WO2008138084A2 PCT/BR2008/000133 BR2008000133W WO2008138084A2 WO 2008138084 A2 WO2008138084 A2 WO 2008138084A2 BR 2008000133 W BR2008000133 W BR 2008000133W WO 2008138084 A2 WO2008138084 A2 WO 2008138084A2
Authority
WO
WIPO (PCT)
Prior art keywords
safrole
enrichment
essential oil
activated charcoal
adsorption
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/BR2008/000133
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English (en)
Other versions
WO2008138084A3 (fr
Inventor
Marco Aurélio CREMASCO
Nazareno De Pina Braga
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universidade Estadual de Campinas UNICAMP
Original Assignee
Universidade Estadual de Campinas UNICAMP
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Filing date
Publication date
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Publication of WO2008138084A2 publication Critical patent/WO2008138084A2/fr
Publication of WO2008138084A3 publication Critical patent/WO2008138084A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/04—Preparation or injection of sample to be analysed
    • G01N30/06—Preparation
    • G01N30/08—Preparation using an enricher
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C11B9/025—Recovery by solvent extraction
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N2030/022—Column chromatography characterised by the kind of separation mechanism
    • G01N2030/025—Gas chromatography
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/04—Preparation or injection of sample to be analysed
    • G01N30/06—Preparation
    • G01N30/14—Preparation by elimination of some components

Definitions

  • the present invention relates to a process for enrichment of safrole from mixtures obtained through safrole extraction carried out in plants from family Lauraceae or plants from family Piperaceae.
  • Essential oils are natural volatile fractions extracted from aromatic plants, and which evaporate at room temperature. These volatile chemical substances present in essential oils are formed by esters classes of fatty acids, mono- and sesquiterpenes, phenylpropanones, aldehyde alcohols, and, in some cases, aliphatic hydrocarbons, among others.
  • Safrole is a natural alylbenzene present in essential oils from plants and it is widely distributed in the plant kingdom. However, it is on species of families Aristolochiaceae, Lauraceae, and Piperaceae that it can be found in substantial amounts.
  • Safrole whose properties are shown in Table 1, is a alyl-benzene, more specifically 4-alyl-l,2- methylenedioxybenzene (C I0 H 10 O 2 ), used in various kinds of industries as a raw material for the manufacturing of different compounds.
  • Essential oils containing safrole usually sold in their natural form by producers, have attained, in the recent years, an increasingly higher market value due to their extensive application and low supply.
  • some examples of compounds resulting from the processing of safrole are piperonal, used as a fragrance fixer; piperonyl butoxyde, used as a synergist insecticide; methylenedioxy-indol-yl-methanoic acid, used as a plant growth regulator; veratraldehyde, used as a flavorant; and methylisochromanylacetic acid, used as an anti-inflammatory.
  • Safrole occurs as the main component of essential oil from Sassafras albidum Nees, a lauraceae found in the eastern area of the United States.
  • safrole-rich species belonging to the family Piperaceae are Piper hispidinervium, C. DC, Piper saiscum, and Piper hispidum.
  • safrole- rich species belonging to the family Lauraceae are Cinnamomum camphora, used as a source of safrole in China, Cinamomum petrophilum, Sassafras albidum, and Ocotea pretiosa widely used in Brazil during the 1980 ⁇ s as a source of safrole.
  • Sassafras oil due to its characteristic flavor, has already been used as food flavorant, but now its use for this purpose is prohibited due to its toxicity. Studies made with rats subjected to a food diet containing safrole evidenced hepatotoxic and carcinogenic effects. However, sassafras oil is still used as a flavorant for technical products, such as insecticides and disinfectants. Nevertheless, the main application of sassafras oil is in the obtainment of safrole and its derivative piperonal, which are important mediators in organic synthesis.
  • Safrole is considered, among the components of Brazilian essential oils, as one of the most abundant, naturally present in sassafras oil extracted from the Laurel Ocotea pretiosa Mez., which is abundant in the valley of Itajai-Ac ⁇ river, Located in the State of Santa Caratina, through the steam distillation of its trunk and branches sassafras oil is produced in Brazil, whose safrole content is higher to 90% (Barreiro e Fraga, Quimica Nova, 22 (5), 744-759, 1999).
  • the cost of implantation for 1 hectare of long pepper is US$ 1,090 and the maintenance cost for 1 hectare from the 2 nd year is US$ 350.
  • a mill station for processing 15 hectares is estimated in US$ 5,044.
  • the processing cost for 1 liter of oil is US$ 0.36.
  • the average net revenue per hectare/year i.e., taking into consideration the whole implantation and maintenance costs for 15 hectares during the period of 6 years, the construction of the mill station, the harvesting and oil processing, including salaries and commissions for a manager and an operator required for the operation of the mill station is R$ 305 (Pimentel, F.A., Consicado tecnico Embrapa/AC, n.99, 1999).
  • the oil price on national and international markets ranges from 4.5 to 8 dollars/kilogram.
  • the productivity in the 1 st year is from 100 to 125 kg of oil per hectare and in the 2 nd year, i.e., with two cuts is from 200 to 250 kg of oil.
  • the oil yield ranges from 2 to 2.5% (Pimentel, F. A., Consicado tecnico Embrapa/AC n.148, 2001).
  • This process of redistillation of an essential oil obtained from the fresh biomass of long pepper occurs within 3 hours and 30 minutes and uses essential oils with a minimal concentration of 75% of safrole and reaches a concentration higher than 90%.
  • the process disclosed by Pimentel, F.A. has a high energy cost and also promotes chemical reactions beceuse of the temperature reached in the distillation process (105 0 C / 221 0 F).
  • the present invention aims to provide a simple and efficient method for enrichment of safrole from an essential oil extracted from plants belonging to family Lauraceae or plants belonging to family Piperaceae. Summary of the invention
  • the present invention refers to an important step in the processing of bioproducts, as the case of essential oils rich in safrole.
  • the invention described herein refers to the enrichment of safrole from mixtures containing safrole resulting from the extraction of safrole from plants which are rich in this component.
  • the enrichment process uses the operation of adsorption and desorption in an activated charcoal bed.
  • the adsorption operation is followed by desorption using an alcoholic solvent which is enriched with the desorbed essential oil.
  • This method employs simple and easy-to-handle equipments, as well as has a lower time consumption and lower financial cost when compared to the safrole content reached by the currently used methods.
  • This invention refers to a process for enrichment of safrole from a mixture containing safrole resulting from the extraction of safrole from plants belonging to family Lauraceae or plants from family Piperaceae, and comprises the following steps:
  • the present invention also refers to an essential oil obtained by the process for enrichment of safrole, and the refered process contains the described steps of adsorption and desorption.
  • the present invention also refers to an essential oil comprising safrole obtained by the process for enrichment of safrole, and the refered process has the described steps of adsorption and desorption.
  • the present invention refers to an essential oil comprising safrole and terpinolene obtained by the process for enrichment of safrole, said process comprising the previously described steps of adsorption and desorption.
  • this invention refers to an essential oil comprising safrole and terpinolene dissolved in an alcoholic solvent, obtained by the process for enrichment of safrole, said process comprising the described steps of adsorption and desorption, as well as an essential oil comprising safrole and terpinolene dissolved in ethanol obtained by the process for enrichment of safrole, said process comprising the described steps of adsorption and desorption.
  • This invention also refers to a process for enrichment of safrole which comprises the use of the process for enrichment of safrole, said process comprising the described steps of adsorption and desorption.
  • Figure 1 shows derivatives of Safrole.
  • Figure 2 shows an experimental packed-bed adsorption / desorption system, where: 1) Vessel containing essential oil to be enriched, 2) hose, 3) peristaltic pump, 4) column containing packed activated charcoal, 5) vessel (vial) for sample collecting.
  • Figure 3 shows chromatograms of essential oil from long pepper (a) without adsorption, (b) with adsorption.
  • Figure 4 is a comparison between the adsorption and the distillation of the essential oil from long pepper (Piper hispidinervium C. DC).
  • Safrole is an important compound which can be used as a raw material for obtaining various products in the pharmaceutical, cosmetic, and agricultural fields. Safrole can be chemically converted into heliotropin, a fixer agent for fragrances, and piperonyl butoxyde, a synergistic agent of pyrethrum, forming a natural, biodegradable insecticide used in food storing and preservation. Safrole is the main constituent of some essential oils from plants such as oils derived from the species Piper hispidinervium C. DC, Cinamomum petrophilum and Sassafras albidum. Usually, these essential oils are commercialized in their natural form by their producers, reaching lower prices on the market.
  • the present invention describes the operation of adsorption and desorption in activated charcoal, in fixed bed and at atmospheric pressure, as a step of concentrating safrole in the essential oil of plants belonging to family Lauraceae or plants from the family Piperaceae.
  • the process for enrichment of safrole described in this invention uses a mixture that contains safrole resulting from the extraction of safrole from plants belonging to family
  • the passage through the activated charcoal of this continuous flow of the mixture containing safrole can be facilitated with the use of a pump.
  • the activated charcoal used in the adsorption step may be arranged in various ways, but preferentially, the activated charcoal is packed into column, through which the mixture containing safrole flows.
  • the desorption step which occurs after the adsorption of the mixture containing safrole, is carried out by contacting the solvent with the activated charcoal containing the adsorbed material.
  • the contact between the solvent with the charcoal in the desorption process can also be made by passing , a continuous flow of solvent through the activated charcoal. This passage of a continuous flow of solvent through the activated charcoal may be provided using a pump.
  • the activated charcoal used in the desorption step may be arranged in various ways, but preferably, the activated charcoal is packed into a column, by which occurs the passage of the solvent. Any solvent that provides the elution of the adsorbed safrole from activated charcoal can be used, but preferably, alcoholic solvents are used, and even more preferably, ethanol is used.
  • a mixture comprising essential oil is obtained.
  • the mixture obtained in the end of the enrichment process may comprise essential oil and an alcoholic solvent.
  • the mixture obtained in the end of the enrichment process comprises essential oil and an alcoholic solvent.
  • the essential oil present in the mixture obtained in the end of the process for enrichment of safrole comprises safrole.
  • the essential oil present in the mixture obtained in the end of the process for enrichment of safrole also comprises safrole and terpinolene.
  • the present invention refers to the essential oil obtained by the process of adsorption and desorption described in this document.
  • the present invention still refers to the essential oil comprising safrole obtained by the process of adsorption and desorption described in this document.
  • This invention also refers to the essential oil comprising safrole and terpinolene obtained by the process of adsorption and desorption described in this document.
  • the essential oil referred in this document is dissolved in an alcoholic solvent, so that, preferentially, the essential oil referred in this invention, is dissolved in ethanol.
  • This invention still refers to a process for enrichment of safrole which comprises the use of the enrichment process previously described containing the steps of adsorption and desorption.
  • the enrichment of safrole was carried out obtained with a mixture containing essential oil from long pepper provided from distillation mills located in the State of Acre.
  • the embodiment of the invention here demonstrated should be used as one form of carrying out the present invention, and should not be done to diminish its scope of protection.
  • the samples were obtained by applying the steam distillation method to leaves and thin branches.
  • the essential oil sample was conveyed by air to the "Faculdade de Engenharia Quimica, Laborat ⁇ rio de Processus em Meios Porosos" (LPMP) and, immediately upon arriving, was stored in a fridge at a temperature of approximately 5 0 C (41 0 F). On average, 30 compounds were detected by chromatographic assay.
  • the prevailing compounds in the mixture extracted from long pepper were safrole and terpinolene.
  • the purity of safrole and terpinolene in the extracted essential oil is shown in Table 2 below.
  • Activated charcoal obtained from bone matter and used as an adsorbent, was acquired in BONECHAR - "Carvao ativado do Brasil" - having a carbon content of 9 to 1 1%.
  • This adsorbent exhibited, as its characteristics: mean particle size, obtained by granulometric assay, equal to 0.0495 mm; specific mass equal to 1 190 kg/m 3 (obtained by gas pycnometry); specific area of 96300 m 2 /kg (obtained by BET), mean pore size of 22 nm and particle porosity of 0.153, both obtained by mercury intrusion porosimetry.
  • Figure 2 was comprised of a stainless steel column 4 packed with activated charcoal, wherein column 4 has 1.04 cm in diameter and 20.0 cm in length, whose void fraction, taking into account the presence of the adsorbent, was of 0.364.
  • a peristaltic pump 3 model BP-HL 2, trademark NOVA was used, which allows for a flow rate range from 1.2 to 6.4 cmVmin.
  • safrole and terpinolene For the characterization of the components (safrole and terpinolene) and the concentrations thereof following the adsorption, safrole (CAS 94-59-7) and terpinolene (CAS 586- 62-9) chromatographic patterns were utilized. Such products were acquired with Aldrich having contents of 99 % and 90 %.
  • the chromatographic assay of the essential oil was carried out in a gas chromatograph from trademark HP5890 II, in a capillary column HP-20M (Carbovax 20M) with 50 meters in length, in order to determinate the fractions from the main components contained in the essential oil.
  • the detector used in this equipment was the flame ionization detector (FID).
  • the heating was of 6 °C/minute (42.8 0 C), starting at 75 0 C (167 0 F) and ending at 210 0 C (410 0 F).
  • the carrier gas, helium was injected in a flow of 1 mL/minute.
  • the volume of oil used for the assay was of 0.5 microliters.
  • the duration time of the assay for the essential oil was of 28.5 minutes.
  • Essential oil was injected by a microsyringe and the results were obtained in a HP printer.
  • the programming for carrying out the assay used the procedure described by Santos et al. (Santos e col., Process Biochemistry, 39, 2269-2275, 2004).
  • the standard compound and, subsequently, the sample possibly containing the compound to be determined were injected.
  • the quantitative assay the external standard methodology was used, in which a solution having a known concentration of the reference compound was injected. Then, the corresponding peak area was measured in the chromatogram. Without changing assay conditions, an equal volume of the sample containing the analyte of unknown concentration was injected in the gas chromatograph. The corresponding peak area was determined in the chromatogram. Because of the identical injected volume, the ratio of the areas is proportional to the concentration.
  • the concentration of safrole in the essential oil occurred by adsorption in the following manner:
  • the adsorbent was taken to an oven at 104 0 C during 24 hours.
  • the adsorbent was placed on a tray for 12 hours.
  • the adsorption column was packed with the dried adsorbent and cooled.
  • the column was installed in the adsorption system.
  • the flow rate of the solution of the mixture containing safrole was set (1.2 mL/min; 3.4 niL/min; 6.4 mL/min).
  • Adsorption time was set to 60 minutes. 8. The mixture containing safrole was pumped in the column.
  • the adsorption operation was interrupted after 60 minutes.
  • the feed flow rate of the solvent was set (1.2 mL/min; 3.4 mL/min; 6.4 mL/min).
  • Desorption time was set to 60 minutes.
  • Table 3 shows the concentrations, in g/ml, of the main components present in the mixture containing safrole before adsorption, while Table 4 shows the purity (in %) of each specie for this situation.
  • Table 5 is shown containing the concentration values, in g/ml, of the main components present in the adsorbent after adsorption.
  • Table 6 shows the purity (in %) of each specie for this situation.
  • adsorption was carried out by using flow rates of the mixture containing safrole from 1.2 ml/min, 3.4 ml/min, and 6.4 ml/min.
  • the enrichment of safrole in the mixture containing safrole can also be tracked by viewing one of the chromatograms obtained in this proposal, as shown in Figure 3.
  • the chromatograms show the concentration of Safrole in the mixture containing Safrole before adsorption (a) and after adsorption (b).
  • the essential oil feeding was changed to solvent feeding (ethanol, HPLC grade) for removing the adsorbed compounds by passing the solvent through the column.
  • solvent feeding ethanol, HPLC grade
  • the amount of solvent used for each assay ranging the feed flow rate from 1.2 mL/min; 3.4 mL/min; 6.4 mL/min, was of 80 mL. It should be pointed out that a higher volume of ethanol was used in the feeding of 6.4 mL/min due to the high ethanol feeding flow rate.
  • Table 7 shows the concentrations of the main components present in the alcohol solution (ethanol) after desorption carried out in three different flow rates (1.2 mL/min, 3.4 mL/min, 6.4 mL/min), while the Table 8 shows the purity (%) of each specie after desorption with ethanol.
  • the values of the concentrations of the main components present in the adsorbent after desorption were zero, which represents a 100 % recovery of the compounds adsorbed by the activated charcoal contained in the column.
  • the results obtained in the adsorption may be compared with the results obtained in the redistillation of essential' oil carried out by Pimentel, F.A. (Pimentel, F.A., Consicado tecnico n.148, Embrapa / AC, 2001).
  • the results obtained by the adsorption and the redistillation of the essential oil from long pepper are compared (Piper hispidinervium C. DC).

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Abstract

La présente invention concerne une étape importante dans le traitement de produits biologiques, comme dans le cas d'huiles essentielles riches en safrole. La présente invention concerne l'enrichissement du safrole à partir de mélanges contenant du safrole résultant de l'extraction du safrole de plantes qui sont riches en ce composant. Le procédé d'enrichissement met en oeuvre des opérations d'adsorption et de désorption dans un lit de charbon actif. L'opération d'adsorption est suivie d'une désorption utilisant un solvant alcoolique qui contient alors l'huile essentielle désorbée enrichie. Ce procédé emploie du matériel simple et facile à manipuler, de même qu'il permet, du fait d'une faible durée et d'un faible coût, à l'enrichissement d'atteindre une teneur en safrole plus élevée que les procédés actuellement employés.
PCT/BR2008/000133 2007-05-10 2008-05-09 Procédé d'enrichissement du safrole Ceased WO2008138084A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BRPI0701772-3 2007-05-10
BRPI0701772-3A BRPI0701772A2 (pt) 2007-05-10 2007-05-10 processo de enriquecimento de safrol

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WO2008138084A2 true WO2008138084A2 (fr) 2008-11-20
WO2008138084A3 WO2008138084A3 (fr) 2008-12-31

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102749395A (zh) * 2012-06-28 2012-10-24 广东省中药研究所 广东海风藤挥发油gc-ms指纹图谱的构建方法及其指纹图谱
CN109060979A (zh) * 2018-08-02 2018-12-21 成都中医药大学 一种亚甲二氧苯丙烯类毒素的测定方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5104810A (en) * 1990-06-27 1992-04-14 United Technologies Corporation Zero gravity purge and trap for monitoring volatile organic compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102749395A (zh) * 2012-06-28 2012-10-24 广东省中药研究所 广东海风藤挥发油gc-ms指纹图谱的构建方法及其指纹图谱
CN109060979A (zh) * 2018-08-02 2018-12-21 成都中医药大学 一种亚甲二氧苯丙烯类毒素的测定方法

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WO2008138084A3 (fr) 2008-12-31

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