WO2021050000A1 - Procédé de préparation d'un extrait de patchouli - Google Patents

Procédé de préparation d'un extrait de patchouli Download PDF

Info

Publication number
WO2021050000A1
WO2021050000A1 PCT/SG2019/050457 SG2019050457W WO2021050000A1 WO 2021050000 A1 WO2021050000 A1 WO 2021050000A1 SG 2019050457 W SG2019050457 W SG 2019050457W WO 2021050000 A1 WO2021050000 A1 WO 2021050000A1
Authority
WO
WIPO (PCT)
Prior art keywords
patchouli
extract
oil
carbon dioxide
extraction
Prior art date
Application number
PCT/SG2019/050457
Other languages
English (en)
Inventor
Ming-Tsai Liang
Original Assignee
Crop Protection (Singapore) Pte. Ltd.
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 Crop Protection (Singapore) Pte. Ltd. filed Critical Crop Protection (Singapore) Pte. Ltd.
Priority to PCT/SG2019/050457 priority Critical patent/WO2021050000A1/fr
Priority to SG11202113342PA priority patent/SG11202113342PA/en
Priority to CN201980100106.XA priority patent/CN114341324A/zh
Publication of WO2021050000A1 publication Critical patent/WO2021050000A1/fr

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0203—Solvent extraction of solids with a supercritical fluid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/028—Flow sheets

Definitions

  • the present disclosure relates to a method for preparing a patchouli extract, and in particular to a method for extracting a patchouli extract having patchouli alcohol.
  • Patchouli oil is the main medicinal ingredient of patchouli. With the increase of research in pharmacological activity and chemical composition of patchouli oil, the value of patchouli oil has received increasing attention. Patchouli oil has good effects in terms of anti-inflammatory, antibacterial activity, anti-oxidation and analgesic effects.
  • Patchouli alcohol is a natural monomer compound with a special aromatic odor extracted from patchouli. Patchouli alcohol can be used in the fragrance or perfume industry. In addition, patchouli alcohol can be used to treat fungal skin diseases, and can also be used as a base material synthesized through other compounds, and therefore the commercial value of patchouli alcohol is increased.
  • the present disclosure provides a method for preparing a patchouli extract, which can effectively obtain a patchouli extract having high-purity patchouli alcohol.
  • Embodiments of the present disclosure provide a method of preparing a patchouli extract.
  • the method includes the following steps. First, a patchouli material is grounded into patchouli powder and pelleted to obtain patchouli granules. Then, liquid carbon dioxide is introduced to perform a supercritical carbon dioxide extraction process on the patchouli granules, wherein the extraction pressure is about 110 bar to 180 bar and the extraction temperature is about 40°C to 60°C. During the supercritical carbon dioxide extraction process, the extracted product obtained, based on the total weight of the introduced liquid carbon dioxide not exceeding 10 times the weight of the patchouli granules, is collected as the first patchouli extract, wherein the first patchouli extract includes the first patchouli oil.
  • the extracted product obtained based on the total weight of the introduced liquid carbon dioxide exceeding 10 times the weight of the patchouli granules but not exceeding 15 times the weight of the patchouli granules, is collected as the second patchouli extract, wherein the second patchouli extract includes the second patchouli oil.
  • the method further includes drying the patchouli material, such that the moisture content of the dried patchouli material is about 15% or less.
  • the patchouli material includes a patchouli leaf, a patchouli stem, or a combination thereof.
  • the size of the patchouli powder is about 140 mesh or less.
  • the patchouli granules have a diameter of about 2 mm to 10 mm, and the thickness of the patchouli granules is about 2.0 mm to 4.5. mm.
  • the extraction pressure is about 120 bar to 150 bar.
  • the first patchouli oil has a melting point of about 10°C to 40°C
  • the second patchouli oil has a melting point of about 40°C to 70°C.
  • the amount of the patchouli alcohol in the first patchouli oil is about 10 wt% to 40 wt%, and the amount of the patchouli alcohol in the second patchouli oil is about 10 wt% to 30 wt%.
  • the method further includes centrifuging the first patchouli extract to separate the first patchouli oil from the patchouli wax in the first patchouli extract.
  • the amount of the patchouli alcohol in the patchouli wax is about 10 wt% to 30 wt%.
  • Embodiments of the present disclosure provide a method of preparing a patchouli extract.
  • the method includes the following steps. First, a patchouli material is grounded into patchouli powder and pelleted to obtain patchouli granules. Then, liquid carbon dioxide is introduced to perform a supercritical carbon dioxide extraction process on the patchouli granules, wherein the extraction pressure is about 110 bar to 180 bar and the extraction temperature is about 40°C to 60°C. The flow rate of the liquid carbon dioxide is 15 kg/hour. During the supercritical carbon dioxide extraction process, the extracted product obtained within an extraction time not exceeding 0.5 hour is collected as the first patchouli extract, wherein the first patchouli extract includes the first patchouli oil.
  • the method further includes drying the patchouli material, such that the moisture content of the dried patchouli material is about 15% or less.
  • the patchouli material includes a patchouli leaf, a patchouli stem, or a combination thereof.
  • the size of the patchouli powder is about 140 mesh or less.
  • the patchouli granules have a diameter of about 2 mm to 10 mm, and the thickness of the patchouli granules is about 2.0 mm to 4.5. mm.
  • the extraction pressure is about 120 bar to 150 bar.
  • the first patchouli oil has a melting point of about 10°C to 40°C
  • the second patchouli oil has a melting point of about 40°C to 70°C.
  • the amount of the patchouli alcohol in the first patchouli oil is about 10 wt% to 40 wt%, and the amount of the patchouli alcohol in the second patchouli oil is about 10 wt% to 30 wt%.
  • the method further includes centrifuging the first patchouli extract to separate the first patchouli oil from the patchouli wax in the first patchouli extract.
  • the amount of the patchouli alcohol in the patchouli wax is about 10 wt% to 30 wt%.
  • the method for preparing the patchouli extract of the present disclosure extracts the patchouli extract having patchouli alcohol from the patchouli granules by using supercritical carbon dioxide, which not only can effectively improve the extraction efficiency, but also can obtain the patchouli oil with high-purity patchouli alcohol.
  • FIG. 1 is a pipeline flow diagram of a supercritical fluid extraction device according to an embodiment of the present disclosure.
  • FIG. 2 is a gas chromatography-mass spectrometry diagram of patchouli oil.
  • FIG. 3 shows the normalized extraction curves of Example 12, Example 13, Comparative Example 1 and Comparative Example 2.
  • a method for preparing a patchouli extract according to an embodiment of the present disclosure can be used for extracting a patchouli extract having the ingredient of patchouli alcohol. In this manner, a patchouli extract having high-purity patchouli alcohol can be obtained.
  • FIG. 1 is a pipeline flow diagram of a supercritical fluid extraction device according to an embodiment of the present disclosure.
  • a patchouli material is dried (for example, by using an oven) so that the moisture content of the dried patchouli material is about 15% or less. In an embodiment, the moisture content of the dried patchouli material is about 12% or less.
  • the patchouli material is, for example, a patchouli leaf, a patchouli stem, or a combination thereof.
  • the patchouli material is grounded and/or cut through a mechanical or physical process until the patchouli powder having a size of about 200 mesh or less is obtained.
  • the size of the patchouli powder is about 40 mesh to 200 mesh. In an embodiment, the size of the patchouli powder is about 40 mesh to 140 mesh.
  • the patchouli powder may be further pelleted to obtain patchouli granules or pellets.
  • the patchouli granules have a diameter of about 2 mm to 10 mm, and the patchouli granules have a thickness of about 2.0 mm to 4.5 mm. In an embodiment, the patchouli granules have a thickness of about 2.5 mm to 3.5 mm. In an embodiment, the patchouli granules have a thickness less than 2.7 mm. If the thickness of the patchouli granules is greater than 5 mm, it will cause difficulty in permeation of carbon dioxide and a problem of lower mass transfer rate.
  • performing extraction by using the patchouli granules can prevent occurrence of channeling during extraction.
  • the patchouli powder is pelleted to form the patchouli granules, the bulk density of the patchouli granules can be significantly increased from 0.3-0.4 to 0.5-0.6, which increases the production rate of the supercritical fluid extraction device.
  • the patchouli granules are placed in an extractor 30 of 5L and subjected to a supercritical carbon dioxide extraction process.
  • liquid carbon dioxide is pumped into the extractor 30 from a working tank 40 through a high pressure pump 12.
  • the extraction pressure is about 110 bar to 180 bar
  • the extraction temperature is about 40°C to 60°C.
  • the extraction pressure is 120 bar -150 bar.
  • the flow rate of carbon dioxide is about 10 kg/hour to 40 kg/hour.
  • the flow rate of carbon dioxide is from about 15 kg/hour to about 30 kg/hour.
  • the flow rate of carbon dioxide is measured by a coriolis flow meter 20.
  • the temperature of the extractor 30 is controlled by a circulating water heater 35, and the pressure of the extractor 30 is controlled by a back pressure regulator 37.
  • the mixture of the extracted carbon dioxide fluid and the patchouli extract enters a separator 10 for decompression separation.
  • the pressure in the separator 10 is about 45 bar to 65 bar, and the temperature in the separator 10 is about 40°C to 60°C.
  • the temperature of the separator 10 is controlled by the circulating water heater 15.
  • the carbon dioxide fluid is heated and gasified, thereby reducing the solubility of the patchouli extract, leaving the patchouli extract in the separator 10 and achieving gas-liquid separation.
  • the gasified carbon dioxide is cooled by a condenser 50 to be liquefied and sent back to the working tank 40 to achieve recirculation of carbon dioxide.
  • the patchouli extract at different time points is collected by opening the valve at the bottom of separator 10.
  • the first patchouli extract is obtained and collected.
  • the second patchouli extract is obtained and collected.
  • the flow rate of the carbon dioxide is 15 kg/hour, and during the supercritical carbon dioxide extraction process, when the extraction time does not exceed 0.5 hour, the first patchouli extract is obtained and collected. In an embodiment, the flow rate of the carbon dioxide is 15 kg/hour, and during the supercritical carbon dioxide extraction process, when the extraction time exceeds 0.5 hour but not exceed 1 hour, the second patchouli extract is obtained and collected.
  • the melting point of the first patchouli extract is lower than the melting point of the second patchouli extract.
  • the first patchouli extract has a melting point not higher than room temperature, and therefore the first patchouli extract is an oily extract at room temperature.
  • the first patchouli extract is orange.
  • the second patchouli extract has a melting point higher than room temperature, and therefore the second patchouli extract is a paste extract at room temperature.
  • the second patchouli extract is dark green.
  • the first patchouli extract includes the first patchouli oil and the second patchouli extract includes the second patchouli oil.
  • the melting point of the first patchouli oil is lower than the melting point of the second patchouli oil.
  • the second patchouli oil has a melting point higher than room temperature. The second patchouli extract can be melted by heating, and the melted product is the second patchouli oil. Therefore, the second patchouli extract can be heated at different temperatures to obtain second patchouli oil of different melting points.
  • the first patchouli oil has a melting point of about 10°C to 40°C
  • the second patchouli oil has a melting point of about 40°C to 70°C.
  • the amount of the patchouli alcohol in the first patchouli oil is about 10 wt% to 40 wt%, and the amount of the patchouli alcohol in the second patchouli oil is about 10 wt% to 30 wt%.
  • the first patchouli extract further includes patchouli wax, wherein the patchouli wax has a melting point higher than 80°C.
  • the first patchouli extract may be further centrifuged to separate the first patchouli oil from the patchouli wax.
  • the amount of the patchouli alcohol in the patchouli wax is about 10 wt% to 30 wt%.
  • the main ingredient in the patchouli oil was analyzed through GC/MS.
  • the column adopted was a DB-5MS capillary column (30 m x 0.250 mm, 0.25 pm, Agilent, USA) installed on the gas chromatography-mass spectrometry (Agilent, 7890B GC/5977A MSD).
  • the temperature of the injector and detector are set at 250°C.
  • a sample of patchouli oil is prepared in the following manner: the stem and the leaf of the patchouli are grounded by using a grinder, respectively, and the same weight of the stem powder and the leaf powder are mixed to obtain the patchouli powder.
  • FIG. 2 is a gas chromatography-mass spectrometry diagram of patchouli oil.
  • pentadecane No. 6
  • the GC/MS spectrum clearly shows the peak position of each of the main ingredients in the patchouli oil, and the result is used as a standard for analysis.
  • the main ingredients of the patchouli oil include: caryophyllene (No. 1), alpha-Guaiene (No. 2), seychellene (No. 3), a-patchoulene (No. 4), beta-maaliene (No. 5), Aciphyllene (No. 7), a-Bulnesene (No. 8) and patchouli alcohol (No. 9).
  • Table 1 lists the nine ingredients of FIG. 2 and their area fractions.
  • the weight fraction of the patchouli alcohol in the obtained patchouli oil can be calculated through the following Equation 1 (calibration curve).
  • the concentration (represented by mg/L) of the patchouli alcohol in the patchouli oil can be obtained through the calibration curve.
  • the total weight of the patchouli oil in 1L solution can be calculated when preparing samples. Therefore, by dividing the concentration of the patchouli alcohol by the total weight of the patchouli oil, the weight fraction of the patchouli alcohol in the patchouli oil can be obtained.
  • a normalized extraction curve is established.
  • the typical extraction curve is a curve diagram of E vs. q, where E is defined as the weight ratio of the patchouli oil to the loaded material, and q is the weight ratio of the accumulated weight of CO2 to the loaded material.
  • E can be used as the extraction yield of the patchouli oil.
  • E is divided by total extractable oil X 0 .
  • the normalized extraction curve means (E/X 0 ). After E is divided by X 0 , the extraction yield is normalized, so it is called the normalized extraction curve.
  • the stems and leaves of the patchouli are grounded, respectively, and the same weight of the stem powder and the leaf powder are mixed to obtain the patchouli powder.
  • 1 kg of the patchouli powder was extracted by using a supercritical fluid extraction device similar to that of FIG. 1 to obtain the patchouli oil.
  • the extraction conditions are: extraction pressure is 140 bar, extraction temperature is 40°C, flow rate of carbon dioxide is 15 kg/hour, extraction time is 0.5 hour.
  • the patchouli oil was prepared in a manner similar to that of Example 1, except that the extraction temperature of Example 2 was 50°C.
  • the patchouli oil was prepared in a manner similar to that of Example 1, except that the flow rate of carbon dioxide of Example 3 was 30 kg/hour.
  • Example 4 [0063] The patchouli oil was prepared in a manner similar to that of Example 1, except that the extraction pressure of Example 4 was 150 bar.
  • Example 6 The patchouli oil was prepared in a manner similar to that of Example 1, except that the extraction temperature of Example 5 was 50°C and the extraction pressure was 150 bar. [0066] [Example 6]
  • the patchouli oil was prepared in a manner similar to that of Example 1, except that the extraction pressure of Example 6 was 150 bar, and the flow rate of carbon dioxide was 30 kg/hour.
  • the stems and leaves of the patchouli were separately grounded until the powder at a size of 140 mesh was obtained, and the same weight of the stem powder and the leaf powder were mixed to obtain the patchouli powder.
  • the patchouli powder was pelleted to obtain thick pressed pellets.
  • the thick pressed pellets have a bulk density of 0.63 (g/mL).
  • 1.28 kg of the thick pressed pellets were extracted by using a supercritical fluid extraction device similar to that of FIG. 1 to obtain the patchouli oil.
  • the extraction conditions are: extraction pressure is 150 bar, extraction temperature is 50°C, flow rate of carbon dioxide is 15 kg/hour, extraction time is 0.5 hour.
  • the stems and leaves of the patchouli were separately grounded until the powder at a size of 150 mesh was obtained, and the same weight of the stem powder and the leaf powder were mixed to obtain the patchouli powder.
  • the patchouli powder was pelleted to obtain thin pressed pellets.
  • the thin pressed pellets have a bulk density of 0.562 (g/mL).
  • 2.155 kg of the thin pressed pellets were extracted by using a supercritical fluid extraction device similar to that of FIG. 1 to obtain the patchouli oil.
  • the extraction conditions are the same as in Example 7.
  • Example 11 [0081] By using a grinder, the leaves of the patchouli were grounded until the leaf powder at a size of 150 mesh was obtained. Next, the leaf powder was pelleted to obtain thin pressed pellets. The thin pressed pellets have a bulk density of 0.578 (g/mL). Then, 1.516 kg of the thin pressed pellets were extracted by using a supercritical fluid extraction device similar to that of FIG. 1 to obtain the patchouli oil. The extraction conditions are the same as in Example 7. [0082] Then, the amount of the patchouli alcohol, the moisture, the acidic value and the ester value of the patchouli oil in the patchouli oil collected in Examples 7 to 11 were measured, and the measurement results are shown in Table 3.
  • Example 8 and Example 11 are prepared by using the leaf powder alone, and the extraction yield of the pellets in Example 8 and Example 11 was significantly higher than Examples 7, 9, and 10.
  • the stems and leaves of the patchouli were separately grounded, and the same weight of the stem powder and the leaf powder were mixed to obtain the patchouli powder.
  • the patchouli powder was pelleted to obtain pellets having a diameter of 5.3 mm and a thickness of 2.7 mm.
  • the patchouli pellets were extracted by using a supercritical fluid extraction device similar to that of FIG. 1 to obtain the patchouli oil.
  • the extraction conditions are: extraction pressure is 150 bar, extraction temperature is 50°C, flow rate of carbon dioxide is 15 kg/hour, and the patchouli extract is collected every 20 minutes.
  • the stems and leaves of the patchouli were separately grounded, and the same weight of the stem powder and the leaf powder were mixed to obtain the patchouli powder.
  • the patchouli powder was pelleted to obtain pellets having a diameter of 5.3 mm and a thickness of 4.7 mm.
  • the patchouli pellets were extracted by using a supercritical fluid extraction device similar to that of FIG. 1 to obtain the patchouli oil.
  • the extraction conditions are: extraction pressure is 150 bar, extraction temperature is 50°C, flow rate of carbon dioxide is 15 kg/hour, and the patchouli extract is collected every 20 minutes.
  • Example 13 By using a grinder, the leaves of the patchouli were grounded to obtain the patchouli powder. Next, the patchouli powder was pelleted to obtain pellets having a diameter of 5.3 mm and a thickness of 2.7 mm. Then, the patchouli pellets were extracted by using a supercritical fluid extraction device similar to that of FIG. 1 to obtain the patchouli oil. The patchouli extract is collected every 20 minutes. [0091] [Comparative Example 2]
  • the stems and leaves of the patchouli were separately grounded until the powder having a size of 140 mesh was obtained, and the same weight of the stem powder and the leaf powder were mixed to obtain the patchouli powder. Then, the patchouli powder is extracted by using a supercritical fluid extraction device similar to that of FIG. 1 to obtain the patchouli oil.
  • the extraction conditions are: extraction pressure is 150 bar, extraction temperature is 50°C, flow rate of carbon dioxide is 15 kg/hour, and the patchouli extract is collected every 20 minutes.
  • FIG. 3 shows the normalized extraction curves of Example 12, Example 13, Comparative Example 1 and Comparative Example 2.
  • the initial slope of the normalized extraction curve of Example 12 i.e., thin pellets
  • Comparative Example 1 i.e., thick pellets
  • the thinner pellets reduce the diffusion distance and thus the mass transfer rate in the flow phase is increased, thus reducing the solvent to feed ratio.
  • the solvent to feed ratio is related to the extraction time of the material. Therefore, the lower the solvent to feed ratio, the shorter the extraction time and the less electricity consumed for the circulation of carbon dioxide.
  • the initial slope of the normalized extraction curve of Comparative Example 2 is smaller than the initial slope of the normalized extraction curve of Example 12 and Example 13 (i.e., pelleted pellets). This is because mass transfer resistance in supercritical fluids for packed beds with pellets can be significantly reduced due to increased flow rates. In addition, for packed beds with abrasive powder, short paths called channels might occur.
  • Example 13 pellets made of leaf powder only
  • Example 12 pellets made of leaf powder and stem powder
  • the stems and leaves of the patchouli were separately grounded, and the same weight of the stem powder and the leaf powder were mixed to obtain the patchouli powder.
  • the patchouli powder was pelleted to obtain patchouli pellets having a diameter of 5.3 mm and a thickness of 2.7 mm.
  • a supercritical fluid extraction device similar to that of FIG. 1 was used to extract the patchouli pellets.
  • the extraction conditions are: extraction pressure is 150 bar, extraction temperature is 50°C, flow rate of carbon dioxide is 15 kg/hour.
  • the extract (referred to as the first patchouli extract) with an extraction time of 0.5 hour was collected, the extract (referred to as the second patchouli extract) with an extraction time of 0.5 hour to 1 hour was collected, and the extract (referred to as the third patchouli extract) with an extraction time of 1 hour -1.5 hours was collected.
  • the first patchouli extract is an oily extract, and the oily extract maintains oiliness at room temperature.
  • the second patchouli extract and the third patchouli extract are paste extracts.
  • the first patchouli extract was further centrifuged at a speed of not less than 2000 rpm by using a centrifuge to separate the patchouli oil from the patchouli wax in the first patchouli extract.
  • About 68.7 wt% of patchouli oil can be obtained from the oily extract, and the patchouli oil contains about 30.7 wt% of patchouli alcohol.
  • the amount of the patchouli alcohol in the patchouli wax is about 23.4 wt%, and the melting point of the patchouli wax is higher than 80°C.
  • the second patchouli extract was heated and the patchouli oil was collected at different temperatures (50°C, 60°C, 70°C, 80°C, above 80°C), that is, the patchouli oil of different melting points was collected.
  • Table 4 lists the weight fraction of patchouli oil of different melting points in the second patchouli extract and the amount of patchouli alcohol in the patchouli oil.
  • the third patchouli extract was heated and the patchouli oil was collected at different temperatures (50°C, 60°C, 70°C, 80°C, above 80°C), that is, the patchouli oil of different melting points was collected.
  • Table 5 lists the weight fraction of patchouli oil of different melting points in the third patchouli extract and the amount of patchouli alcohol in the patchouli oil.
  • the amount of patchouli alcohol in the patchouli extract decreases with extraction time. Most of the patchouli alcohol in the pellets will be extracted in the first hour. If the extraction is interrupted after collecting the patchouli extract with an extraction time of 0.5 hour and the patchouli extract with an extraction time of 0.5 hour to 1 hour, three different products can be obtained: (1) patchouli oil containing 30.7 wt% of patchouli alcohol; (2) patchouli wax containing 23.4 wt% of patchouli alcohol; (3) patchouli paste containing 28.6 wt% of patchouli alcohol.
  • the method for preparing the patchouli extract of the present disclosure has simple operation steps, good stability, and uses only non-toxic carbon dioxide during the entire purification process, and has the advantages of realizing automation, low consumption of solvent, being environment, high production rate and so on as compared with conventional preparation methods. Further, the method for preparing a patchouli extract of the present disclosure extracts a patchouli extract having patchouli alcohol from the patchouli pellets by using supercritical carbon dioxide, which not only can effectively improve the extraction efficiency, but also can obtain patchouli oil with high-purity patchouli alcohol.

Abstract

La présente invention concerne un procédé de préparation d'un extrait de patchouli, qui comprend les étapes suivantes. Un matériau de patchouli est broyé en poudre de patchouli puis granulé pour obtenir des granules de patchouli. Du dioxyde de carbone liquide est introduit pour effectuer un procédé d'extraction de dioxyde de carbone supercritique sur les granules de patchouli, la pression d'extraction étant d'environ 110 à 180 bars et la température d'extraction étant d'environ 40 à 60 °C. Pendant le processus d'extraction de dioxyde de carbone supercritique, le produit extrait obtenu, sur la base du poids total du dioxyde de carbone liquide introduit ne dépassant pas 10 fois le poids des granules de patchouli, est recueilli en tant que premier extrait de patchouli, qui comprend la première huile de patchouli. Le produit extrait obtenu, sur la base du poids total du dioxyde de carbone liquide introduit dépassant 10 fois mais ne dépassant pas 15 fois le poids des granules de patchouli, est recueilli en tant que second extrait de patchouli, qui comprend la seconde huile de patchouli.
PCT/SG2019/050457 2019-09-12 2019-09-12 Procédé de préparation d'un extrait de patchouli WO2021050000A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/SG2019/050457 WO2021050000A1 (fr) 2019-09-12 2019-09-12 Procédé de préparation d'un extrait de patchouli
SG11202113342PA SG11202113342PA (en) 2019-09-12 2019-09-12 Method of preparing patchouli extract
CN201980100106.XA CN114341324A (zh) 2019-09-12 2019-09-12 制备广藿香萃取物的方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/SG2019/050457 WO2021050000A1 (fr) 2019-09-12 2019-09-12 Procédé de préparation d'un extrait de patchouli

Publications (1)

Publication Number Publication Date
WO2021050000A1 true WO2021050000A1 (fr) 2021-03-18

Family

ID=74866353

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SG2019/050457 WO2021050000A1 (fr) 2019-09-12 2019-09-12 Procédé de préparation d'un extrait de patchouli

Country Status (3)

Country Link
CN (1) CN114341324A (fr)
SG (1) SG11202113342PA (fr)
WO (1) WO2021050000A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114814020A (zh) * 2022-04-20 2022-07-29 安康市农产品质量安全检验监测中心 一种农产品中残留有机磷农药的分析方法
WO2023204756A3 (fr) * 2022-04-20 2023-11-30 Crop Protection (Singapore) Pte Ltd Procédé et appareil de préparation d'un extrait botanique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101653518A (zh) * 2008-08-19 2010-02-24 长春国奥药业有限公司 一种治疗小儿腹泻及小儿感染性腹泻的药物组合及制备方法
CN104274634A (zh) * 2014-08-14 2015-01-14 杭州方回春堂国药馆有限公司 一种提神醒脑及消肿止痒的复方植物精油及其制备方法
KR20170109935A (ko) * 2016-03-22 2017-10-10 재단법인 전남생물산업진흥원 버즘나무 방패벌레 방제용 살충제 조성물

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5032249A (en) * 1990-08-28 1991-07-16 Conoco Inc. Fractionation process for petroleum wax
JP3935988B2 (ja) * 1996-02-09 2007-06-27 小川香料株式会社 改質されたミント油類とその製造方法
ES2300319T3 (es) * 2000-01-20 2008-06-16 Ciba Specialty Chemicals Holding Inc. Procedimiento para la obtencion de (-)-guaiol y uso de este.
EP1300375A4 (fr) * 2000-05-25 2006-09-06 Sumitomo Osaka Cement Co Ltd Composition hydraulique thermoplastique, produit fa onne fabrique a partir de cette composition par durcissement par hydratation, et procede de fabrication de produit fa onne
CN1234828C (zh) * 2002-11-21 2006-01-04 上海高科联合生物技术研发有限公司 超临界二氧化碳萃取薏苡仁油的方法
KR100763035B1 (ko) * 2006-03-02 2007-10-04 주식회사 래디안 선학초로부터 여드름 개선 유효성분물질의 추출분리방법과이로부터 얻어지는 유효성분물질을 포함하는 화장료 조성물
CN101485647B (zh) * 2009-02-27 2013-04-24 东莞广州中医药大学中医药数理工程研究院 百秋李醇在制备药物中的用途
TWI492755B (zh) * 2009-12-30 2015-07-21 Metal Ind Res & Dev Ct 抗糖尿病及抗新陳代謝疾病之香椿超臨界萃取物、製備方法及用途
CN102821771B (zh) * 2010-12-28 2015-01-14 高雄医学大学 抗糖尿病及抗新陈代谢疾病的香椿超临界萃取物、制备方法及用途
CN102807473B (zh) * 2012-03-16 2014-07-30 成都华神集团股份有限公司 广藿香醇的分离纯化方法
CN106398870A (zh) * 2016-08-28 2017-02-15 广西灏源盛世生物科技有限公司 一种广藿香精油的提取方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101653518A (zh) * 2008-08-19 2010-02-24 长春国奥药业有限公司 一种治疗小儿腹泻及小儿感染性腹泻的药物组合及制备方法
CN104274634A (zh) * 2014-08-14 2015-01-14 杭州方回春堂国药馆有限公司 一种提神醒脑及消肿止痒的复方植物精油及其制备方法
KR20170109935A (ko) * 2016-03-22 2017-10-10 재단법인 전남생물산업진흥원 버즘나무 방패벌레 방제용 살충제 조성물

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DONELIAN, A. ET AL.: "Comparison of extraction of patchouli (Pogostemon cablin) essential oil with supercritical C02 and by steam distillation", J. OF SUPERCRITICAL FLUIDS, vol. 48, no. 1, 8 October 2008 (2008-10-08), pages 15 - 20, XP025924407, [retrieved on 20191101], DOI: 10.1016/J.SUPFLU. 2008.09.02 0 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114814020A (zh) * 2022-04-20 2022-07-29 安康市农产品质量安全检验监测中心 一种农产品中残留有机磷农药的分析方法
CN114814020B (zh) * 2022-04-20 2023-08-29 安康市农产品质量安全检验监测中心 一种农产品中残留有机磷农药的分析方法
WO2023204756A3 (fr) * 2022-04-20 2023-11-30 Crop Protection (Singapore) Pte Ltd Procédé et appareil de préparation d'un extrait botanique

Also Published As

Publication number Publication date
SG11202113342PA (en) 2021-12-30
CN114341324A (zh) 2022-04-12

Similar Documents

Publication Publication Date Title
Li et al. Extraction of Cuminum cyminum essential oil by combination technology of organic solvent with low boiling point and steam distillation
Peterson et al. Extraction of essential oil from geranium (Pelargonium graveolens) with supercritical carbon dioxide
CN101386566B (zh) 片状结晶体的天然冰片的制取方法
CN103789094A (zh) 一种从沉香木屑中提取沉香精油的方法
Ivanovic et al. The analysis of simultaneous clove/oregano and clove/thyme supercritical extraction
WO2021050000A1 (fr) Procédé de préparation d'un extrait de patchouli
CN103087828B (zh) 一种滇红精油及其制备方法
CN103266015A (zh) 一种天然花香精油采集装置及使用方法
CN101019909B (zh) 一种超临界萃取红花的方法
CN105713732A (zh) 一种八角茴香油的提取方法
Ruiz-Rodriguez et al. Supercritical fluid extraction of tobacco leaves: A preliminary study on the extraction of solanesol
CN105132182B (zh) 一种基于亚临界萃取制备高良姜挥发油的方法及其制得的产品
CN105669797A (zh) 一种从牛蒡子中分离牛蒡子油、牛蒡苷、牛蒡苷元、牛蒡酚e和牛蒡酚h的方法
JP6749649B2 (ja) 植物油の製造方法および製造装置
Micic et al. Supercritical extraction of Salvia officinalis L
CN102533446B (zh) 一种脱除柑橘属植物精油中呋喃香豆素类成分的方法
CN101318893B (zh) 一种从八角中同时提取莽草酸和香精油的工艺
TWI699232B (zh) 製備廣藿香萃取物的方法
CN110632216A (zh) 提取样品中矿物油的方法及检测方法
CN110684589A (zh) 一种大麻油的提取纯化方法
CN104083556A (zh) 一种从魔芋中提取魔芋神经酰胺的方法
CN107098838B (zh) 一种大蒜阿霍烯对照品的制备方法
CN111820449B (zh) 一种从工业大麻中提取挥发油的方法
WO2022018451A1 (fr) Isolement de cannabinoïdes à l'aide de matériaux mésoporeux
CN101904947A (zh) 一种蔓荆子提取物及其超临界制备工艺

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19945246

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19945246

Country of ref document: EP

Kind code of ref document: A1