CN110396456B - Extraction additive and method for extracting plant essential oil by using supercritical extraction method - Google Patents

Extraction additive and method for extracting plant essential oil by using supercritical extraction method Download PDF

Info

Publication number
CN110396456B
CN110396456B CN201910640326.3A CN201910640326A CN110396456B CN 110396456 B CN110396456 B CN 110396456B CN 201910640326 A CN201910640326 A CN 201910640326A CN 110396456 B CN110396456 B CN 110396456B
Authority
CN
China
Prior art keywords
extraction
essential oil
carbon dioxide
additive
plant essential
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.)
Active
Application number
CN201910640326.3A
Other languages
Chinese (zh)
Other versions
CN110396456A (en
Inventor
史清照
徐秀娟
刘珊
张启东
柴国璧
席辉
毛健
范武
刘俊辉
宋瑜冰
张文娟
胡军
屈展
杨伟平
姬凌波
霍现宽
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.)
Zhengzhou Tobacco Research Institute of CNTC
Original Assignee
Zhengzhou Tobacco Research Institute of CNTC
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 Zhengzhou Tobacco Research Institute of CNTC filed Critical Zhengzhou Tobacco Research Institute of CNTC
Priority to CN201910640326.3A priority Critical patent/CN110396456B/en
Publication of CN110396456A publication Critical patent/CN110396456A/en
Application granted granted Critical
Publication of CN110396456B publication Critical patent/CN110396456B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B9/00Essential oils; Perfumes
    • C11B9/02Recovery or refining of essential oils from raw materials
    • C11B9/025Recovery by solvent extraction
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/54Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

The invention provides an extraction additive, which is a siloxane polyoxyethylene ether compound used for extracting plant essential oil, wherein the siloxane polyoxyethylene isThe vinyl ether compound has the structural general formula

Description

Extraction additive and method for extracting plant essential oil by using supercritical extraction method
Technical Field
The invention belongs to the field of preparation of essences and spices, and particularly relates to an extraction additive and a method for extracting plant essential oil by using a supercritical extraction method.
Background
The plant essential oil is a volatile oily liquid which exists in leaves, roots, peels, flowers and fruits of aromatic plants, can be distilled with water vapor and has certain smell. At present, methods for obtaining plant essential oil mainly include extrusion method, steam distillation method, organic solvent extraction method and the like. The extraction efficiency of the extrusion method and the steam distillation method is low, the organic solvent extraction method not only needs a large amount of organic solvent and is easy to pollute the environment, but also needs operations such as freezing dewaxing, distillation and the like in the post-treatment process, and the process is complex. In recent years, the supercritical carbon dioxide extraction technology shows good development momentum in the aspect of essential oil preparation, and is a method for extracting raw materials by utilizing the characteristics of high permeability, fluidity, low viscosity, no toxicity, no odor and no solvent residue of carbon dioxide in a supercritical state. For example, Dulijun et al, published in the academic paper of analytical tests, 2019,38(1), entitled "steam distillation and supercritical CO2The paper of the extraction method combined with the gas chromatography-mass spectrometry for analyzing the essential oil components of the piper nigrum describes the adoption of supercritical CO2The method has less damage to natural components of essential oil, retains a large amount of active components, and has high essential oil yield.
Although supercritical carbon dioxide has many advantages, carbon dioxide is always a low-polarity solvent, has poor solvating power and has low extraction efficiency for aroma components (alcohols, ketones, acids and the like) with high polarity in plants. Ethanol and methanol are reported as entrainers and added into supercritical carbon dioxide, so that the extraction efficiency of the supercritical carbon dioxide can be improved (the technology for extracting and separating the supercritical carbon dioxide fluid [ J ]. fine and special chemicals, 2002, 10(6): 17-19.; research on process for extracting onion skin flavone from supercritical carbon dioxide, Song-Ruoqin, Yinghua, Wuhuachang, et al. [ J ]. agricultural product processing, 2018,465(19): 39-41.). However, the addition amount of the entrainer is often large, so that the macromolecular substances such as protein and polysaccharide are dissolved out while the aroma components are extracted, although the extraction efficiency is improved to a certain extent, the macromolecular substances are further removed by post-treatment, and meanwhile, in the process of removing the entrainer, the loss of volatile and easily oxidized aroma substances is caused by long-time heating, so that the sensory style characteristics of the product are not outstanding.
Disclosure of Invention
In view of the above, the present invention provides an extraction additive and a method for extracting plant essential oil by supercritical extraction, so as to solve the above problems.
Therefore, the technical scheme provided by the invention is as follows: an extraction additive is a siloxane polyoxyethylene ether compound used for extracting plant essential oil, and the structural general formula of the siloxane polyoxyethylene ether compound is as follows:
Figure BDA0002131630200000021
the value of the polymerization degree n in the structural general formula is 5-10. The value of the degree of polymerization "n" is a positive integer, and can be 5, 6, 7, 8, 9 or 10.
That is, the silicone polyoxyethylene ether compound is 3-propyl- (methylpentanoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane, 3-propyl- (methylhexaoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane, 3-propyl- (methylheptoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane, 3-propyl- (methyloctapolyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane, 3-propyl- (methylnonapolyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane or 3-propyl- (methyldecapolyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane.
The invention also provides a method for extracting plant essential oil by using a supercritical extraction method, which comprises the following steps: adding the extraction additive and a supercritical carbon dioxide solvent into plant raw materials to perform plant essential oil extraction treatment, wherein the addition amount of the additive is 0.02-1% of the mass of the supercritical carbon dioxide solvent. The amount of the additive added may be, according to the actual conditions, 0.02%, 0.05%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1% or the like of the mass of the supercritical carbon dioxide solvent.
Based on the above, the feed-liquid ratio of the plant raw material to the supercritical carbon dioxide solvent is 1: 8-1: 12 g/mL. Preferably, the feed-liquid ratio is 1: 9-1: 11 g/mL.
Based on the method for extracting the plant essential oil by using the supercritical extraction method, the plant raw materials and the additive are placed in an extraction kettle, then the supercritical carbon dioxide solvent is injected into the extraction kettle for extraction for 2-4 hours under the conditions of 40-60 ℃ and 20-35 MPa to obtain an extract, and the extract is separated and purified to obtain the plant essential oil. Wherein, the extraction liquid can be obtained by adopting a static extraction method or a dynamic circulation extraction method. Preferably, in the process of obtaining the extract, the extract is obtained by dynamic circulation extraction for 2-4 h at the flow rate of 20-30L/h under the conditions of the temperature and the pressure.
Based on the above, the step of performing separation and purification treatment on the extract liquid comprises: and the extract enters a first-stage separator for cooling treatment, and then enters a second-stage separator for removing carbon dioxide to prepare the plant essential oil. Specifically, the extract enters the first-stage separator, macromolecular substances with low solubility are removed through temperature reduction and pressure reduction treatment, and then the extract enters the second-stage separator, wherein a carbon dioxide solvent is discharged in a gas form, and finally the plant essential oil is obtained.
Based on the above, the plant raw material is derived from one or any combination of roots, stems, leaves, flowers, fruits or fruit peels of fresh plants. Wherein, the plant raw material can be pretreated into granules, sheets or threads according to actual requirements.
Compared with the prior art, the extraction additive siloxane polyoxyethylene ether compound provided by the invention has lower polarity of siloxane groups, and has better affinity with solvents for extracting plant essential oil, such as butane and carbon dioxide; meanwhile, the polyoxyethylene ether group in the siloxane polyoxyethylene ether compound can increase the solvating capacity of the solvent for extracting the plant essential oil and promote the dissolution of medium and high polarity components in the plant raw materials, so that the siloxane polyoxyethylene ether compound serving as an additive of the solvent for extracting the plant essential oil can assist the solvent for extracting the plant essential oil to extract the plant essential oil, and the extraction efficiency of the plant essential oil is improved. The siloxane polyoxyethylene ether compound as the additive can be used as an additive for extraction technologies such as a supercritical extraction technology, a subcritical extraction technology and the like, for example, as an additive for a subcritical butane extraction technology, an additive for a supercritical carbon dioxide extraction technology and the like.
The invention also provides a method for extracting plant essential oil by using a supercritical extraction method, which mainly uses a supercritical extraction technology, takes carbon dioxide as an extraction solvent, and adds the siloxane polyoxyethylene ether compound as an additive to extract the plant essential oil from plant raw materials; the siloxane polyoxyethylene ether compound serving as the carbon dioxide additive has good affinity with carbon dioxide, can improve the solvation capacity of the carbon dioxide and promotes the dissolution of high-polarity essential oil components in the plant raw materials, so that the method for extracting the plant essential oil can realize more efficient extraction of fragrant substances of natural plant raw materials and effectively improve the extraction efficiency of the plant essential oil. In addition, because the addition amount of the siloxane polyoxyethylene ether compound in the method for extracting the plant essential oil provided by the invention is relatively low, the plant essential oil with high quality can be obtained without removing the siloxane polyoxyethylene ether compound serving as the additive after the supercritical carbon dioxide extraction, and the method can also avoid the loss of aroma substances caused by removing the additive. Therefore, the plant essential oil prepared by the method provided by the invention has full and vivid fragrance and can be used in the fields of tobacco, daily chemicals, food, medicine, agriculture and the like.
Detailed Description
The technical solution of the present invention is further described in detail by the following embodiments.
Example 1
This example provides an extraction additive that is 3-propyl- (methylpenta-polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane.
The embodiment provides a method for extracting rose essential oil by using a supercritical extraction method, which comprises the following steps: 100g of dried fresh rose petals were placed in a supercritical extraction kettle, followed by 2.67g (i.e., 0.3%, carbon dioxide density of 890.92kg/m under the experimental conditions)3) Starting a supply valve of a carbon dioxide storage tank, injecting 1000mL of supercritical carbon dioxide solvent (namely the feed-liquid ratio is 1:10g/mL), and dynamically extracting for 4h under the conditions of 45 ℃, 30MPa of pressure and 25L/h of flow rate to obtain rose extract; the rose extract enters a first-stage separator for temperature reduction and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, wherein a carbon dioxide solvent is changed into a gas state, and is separated from an extract to release carbon dioxide gas, so that rose essential oil is obtained, and the yield is 0.94%.
Comparative example 1
The comparative example 1 provides a method for extracting rose essential oil by using a supercritical extraction method, which is mainly different from the method in the example 1 in that: in comparative example 1, 3-propyl- (methylpenta-polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane was not added, and specifically, the method provided in comparative example 1 included: transferring 100g of dried fresh rose petals to a supercritical extraction kettle, then adding 10mL of ethanol with the volume fraction of 10%, starting a supply valve of a carbon dioxide storage tank, injecting 1000mL of supercritical carbon dioxide solvent, and dynamically extracting for 4h under the conditions of 45 ℃, pressure of 30MPa and flow rate of 25L/h to obtain a rose extraction stock solution; the rose extract enters a first-stage separator for temperature reduction and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, and carbon dioxide is evaporated in a gas form; then removing the ethanol entrainer by rotary evaporation treatment to obtain a rose extract with the yield of 1.05 percent; the obtained rose extract is subjected to freezing dewaxing at-10 deg.C for 2 times by using 95% ethanol to remove waxiness, and the ethanol-removed solvent is removed by rotary evaporation under reduced pressure to obtain 0.32g of rose essential oil with high content of aroma components, with a yield of 0.32%.
Analysis of Rose essential oil
300mg of the rose essential oils obtained in example 1 and comparative example 1 were accurately weighed, dissolved in dichloromethane, and then an internal standard (phenethylacetate) was added, and the components of the two were analyzed by GC-MS, respectively, and the analysis results are shown in Table 1. Wherein, the component analysis adopts the following instrument conditions:
a chromatographic column: DB-5MS capillary column (30m 0.25mm 0.25 μm); sample inlet temperature: 250 ℃; carrier gas: high purity helium gas; the flow rate is 1.0 mL/min; sample introduction amount: 1 mu L of the solution; the split ratio is 10: 1; temperature programming: keeping the temperature at 60 deg.C for 1min, heating to 260 deg.C at a heating rate of 5 deg.C/min, and keeping for 5 min.
An ionization mode: EI; ion source temperature: 230 ℃; electron energy: 70 eV; quadrupole temperature: 150 ℃; electron multiplier voltage: 1.89 kV; the mass scanning range is 33-500 amu; the scanning mode comprises the following steps: full scanning; solvent retardation: 7.0 min.
TABLE 1 analysis table of essential oil components of rose
Figure BDA0002131630200000061
Figure BDA0002131630200000071
Note: "-" indicates no detection
As can be seen from table 1: under the same detection conditions, 31 components can be detected in the rose essential oil obtained in example 1 by a GC-MS method, and 25 components can be detected in the rose essential oil obtained in comparative example 1; in addition, the content of the active ingredients of the rose essential oil obtained in example 1 is significantly higher than that of the rose essential oil obtained in comparative example 1, so that, compared with the extraction method of the rose essential oil provided in comparative example 1, the extraction method of the rose essential oil provided in example 1 is capable of extracting more active ingredients from roses by adding the additive 3-propyl- (methyl penta polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyl trisiloxane, thereby fully explaining that the extraction efficiency of supercritical carbon dioxide on the active ingredients of roses can be improved by adding the extraction additive 3-propyl- (methyl penta polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyl trisiloxane in example 1.
Example 2
This example provides an extraction additive that is 3-propyl- (methylnonapolyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane.
The embodiment provides a method for extracting rose essential oil by using a supercritical extraction method, which comprises the following steps: 100g of dried fresh rose petals are placed in a supercritical extraction kettle, and 4.81g (namely 0.6 percent) of the dried fresh rose petals are added, wherein the density of carbon dioxide is 890.92kg/m under the experimental condition3) 3-propyl- (methyl nonapolyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane, opening a supply valve of a carbon dioxide storage tank, injecting 900mL (namely the feed-liquid ratio is 1:9g/mL) of supercritical carbon dioxide solvent, and dynamically extracting for 4h under the conditions of 45 ℃, the pressure of 30MPa and the flow rate of 25L/h to obtain rose extract; the rose extract enters a first-stage separator for temperature reduction and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, wherein a carbon dioxide solvent is changed into a gas state, and is separated from an extract to release carbon dioxide gas, so that rose essential oil is obtained, and the yield is 1.22%.
From examples 1 and 2 and comparative example 1, it can be seen that: in the method for extracting rose essential oil provided in embodiments 1 and 2, the extraction additive siloxane polyoxyethylene ether compounds are added while the supercritical carbon dioxide extraction technology is utilized, and the rose essential oil can be directly obtained after the two-stage separation treatment of the rose extract without additionally removing the corresponding extraction additive; in the method for extracting rose essential oil provided in comparative example 1, the supercritical carbon dioxide extraction technology is utilized, and the entrainer ethanol solution is added at the same time, and the rose extraction stock solution obtained by the method needs to be subjected to two-stage separation treatment, then subjected to rotary evaporation treatment to remove the ethanol entrainer therein, and then subjected to dewaxing treatment to obtain the rose essential oil. The yield of the rose essential oil obtained in examples 1, 2 and 3 was higher than that of the rose extract obtained in comparative example 1, and was much higher than that of the rose essential oil obtained in comparative example 1. It can be seen that the addition of the siloxane polyoxyethylene ether compound as an extraction additive in the method for extracting rose essential oil provided in examples 1 and 2 can effectively promote the extraction of the aroma components in rose petals, and compared with the addition of ethanol in the method provided in comparative example 1, the method omits a step of removing an ethanol entrainer in post-treatment, and simplifies the preparation process.
Example 3
This example provides an extraction additive that is 3-propyl- (methylpentaoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane.
The embodiment provides a method for extracting tobacco essential oil by using a supercritical extraction method, which comprises the following steps: 100g of fresh tobacco was charged into a supercritical carbon dioxide extraction vessel, followed by the addition of 0.83g (i.e. 0.1%, carbon dioxide having a density of 834.89kg/m under the experimental conditions3) 3-propyl- (methyl penta-polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyl trisiloxane, opening a supply valve of a carbon dioxide storage tank, injecting 1000mL of supercritical carbon dioxide solvent (namely the material-liquid ratio is 1:10g/mL), and dynamically extracting for 2h under the conditions of 50 ℃, 25MPa of pressure and 30L/h of flow rate to obtain tobacco extract; the tobacco extract enters a first-stage separator for cooling and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, wherein a carbon dioxide solvent is changed into a gas state, and is separated from an extract to release carbon dioxide gas, so that tobacco essential oil is obtained, and the yield of the tobacco essential oil is 1.94%.
Example 4
This example provides an extraction additive that is 3-propyl- (methyldiethoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane.
The embodiment provides a method for extracting tobacco essential oil by using a supercritical extraction method, which comprises the following steps: 100g of fresh tobacco was charged into a supercritical carbon dioxide extraction vessel, followed by addition of 1.00g (i.e. 0.15%, carbon dioxide having a density of 834.89kg/m under the experimental conditions)3) 3-propyl- (methyl deca-polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyl trisiloxane, opening a supply valve of a carbon dioxide storage tank, injecting 800mL of supercritical carbon dioxide solvent (namely the feed-liquid ratio is 1:8g/mL), and dynamically extracting for 2h under the conditions of 50 ℃, 25MPa of pressure and 30L/h of flow rate to obtain tobacco extract; the tobacco extract enters a first-stage separator for cooling and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, wherein carbon dioxide is changed into a gas state, and is separated from an extract to release carbon dioxide gas, so that tobacco essential oil is obtained, and the yield of the tobacco essential oil is 2.04%.
Example 5
This example provides an extraction additive that is 3-propyl- (methylhexa-polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane.
The embodiment provides a method for extracting tobacco essential oil by using a supercritical extraction method, which comprises the following steps: 100g of fresh tobacco was charged into a supercritical carbon dioxide extraction vessel, followed by addition of 1.00g (i.e. 0.1%, carbon dioxide having a density of 834.89kg/m under the experimental conditions)3) 3-propyl- (methyl hexa-polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyl trisiloxane, opening a supply valve of a carbon dioxide storage tank, injecting 1200mL (namely the feed-liquid ratio is 1:12g/mL) of supercritical carbon dioxide solvent, and dynamically extracting for 2h under the conditions of 50 ℃, 25MPa of pressure and 30L/h of flow rate to obtain tobacco extract; the tobacco extract liquid enters a first-stage separator for cooling and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, wherein carbon dioxide is changed into a gas state, and is separated from the extract to release carbon dioxide gas to obtain tobacco essential oil, and the yield of the tobacco essential oil is1.73%。
Comparative example 2
The comparison example provides a method for extracting tobacco essential oil by using a supercritical extraction method, and the method is mainly different from the method in the examples 3 to 5 in that no siloxane polyoxyethylene ether compound as an extraction additive is added in the comparison example 2. Specifically, the method for extracting tobacco essential oil by using the supercritical extraction method provided by the comparative example comprises the following steps: filling 100g of fresh tobacco shreds into a supercritical carbon dioxide extraction kettle, opening a supply valve of a carbon dioxide storage tank, injecting 1000mL of supercritical carbon dioxide solvent (namely the material-liquid ratio is 1:10g/mL), and dynamically extracting for 2h under the conditions of 50 ℃, 25MPa of pressure and 30L/h of flow rate to obtain an extraction stock solution; the extraction stock solution enters a first-stage separator for cooling and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, wherein carbon dioxide is changed into a gas state, and is separated from an extract to release carbon dioxide gas, so that the tobacco essential oil is obtained, and the yield of the tobacco essential oil is 0.96%.
Example 6
This example provides an extraction additive that is 3-propyl- (methyloctapolyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane.
The embodiment provides a method for extracting tea essential oil by using a supercritical extraction method, which comprises the following steps: 100g of fresh tea leaves were transferred to a supercritical extraction kettle, followed by the addition of 4.29g (i.e. 0.5%, under the experimental conditions carbon dioxide has a density of 857.82kg/m3) 3-propyl- (methyloctapolyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane, opening a supply valve of a carbon dioxide storage tank, injecting 1000mL (namely the feed-liquid ratio is 1:10g/mL) of supercritical carbon dioxide solvent, and dynamically extracting for 3h under the conditions of 45 ℃, 25MPa of pressure and 20L/h of flow rate to obtain tea extract; the tea extract liquid enters a first-stage separator and is subjected to temperature reduction and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, carbon dioxide is evaporated in a gas form to directly obtain tea essential oil, wherein the yield of the tea essential oil is 0.92%.
Comparative example 3
This comparative example provides a method for extracting tea leaf essential oil, which is different from example 6 mainly in that 3-propyl- (methylpenta-polyoxyethylene) -1,1,1,3,5,5, 5-heptamethyltrisiloxane was not added in this comparative example 3. Specifically, the method for extracting tobacco essential oil by using the supercritical extraction method provided by the comparative example comprises the following steps: transferring 100g of fresh tea leaves into a supercritical extraction kettle, opening a supply valve of a carbon dioxide storage tank, injecting 1000mL of supercritical carbon dioxide solvent (namely the material-liquid ratio is 1:10g/mL), and dynamically extracting for 3h under the conditions of 45 ℃, 25MPa of pressure and 20L/h of flow rate to obtain an extraction stock solution; the extraction stock solution firstly enters a first-stage separator for cooling and pressure reduction treatment to remove macromolecular substances with low solubility, and then is treated by a second-stage separator, carbon dioxide is evaporated in a gas form to directly obtain the tea essential oil, and the yield of the tea essential oil is 0.65%.
Therefore, when the method for extracting the plant essential oil provided by the embodiment of the invention is used for preparing the plant essential oil, a small amount of siloxane polyoxyethylene ether compound serving as an extraction additive is added, so that the extraction efficiency of the supercritical carbon dioxide on the plant essential oil can be effectively improved; compared with common extraction additives such as methanol, ethanol and the like, the proportion of the added siloxane polyoxyethylene ether compounds is lower, the process of removing the extraction additives is omitted, the preparation steps are saved, and the loss of aroma substances caused by the process of removing the extraction additives is reduced.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention and not to limit it; although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art will understand that: modifications to the specific embodiments of the invention or equivalent substitutions for parts of the technical features may be made; without departing from the spirit of the present invention, it is intended to cover all aspects of the invention as defined by the appended claims.

Claims (5)

1. A method for extracting plant essential oil by using a supercritical extraction method comprises the following steps: adding an extraction additive and a supercritical carbon dioxide solvent into plant raw materials to perform plant essential oil extraction treatment, wherein the addition amount of the extraction additive is 0.02-1% of the mass of the supercritical carbon dioxide solvent, the extraction additive is a siloxane polyoxyethylene ether compound used for extracting the plant essential oil, and the structural general formula of the siloxane polyoxyethylene ether compound is as follows:
Figure DEST_PATH_IMAGE002
the value of the polymerization degree n in the structural general formula is 5-10.
2. The method for extracting plant essential oil by using the supercritical extraction method as claimed in claim 1, wherein the feed-liquid ratio of the plant raw material to the supercritical carbon dioxide solvent is 1: 8-1: 12 g/mL.
3. The method for extracting plant essential oil by using the supercritical extraction method as claimed in claim 1 or 2, wherein the plant raw material and the extraction additive are placed in an extraction kettle, then the supercritical carbon dioxide solvent is injected for extraction for 2-4 hours at the temperature of 40-60 ℃ and the pressure of 20-35 MPa to obtain an extract, and the extract is subjected to separation and purification treatment to obtain the plant essential oil.
4. The method for extracting plant essential oil by using the supercritical extraction method as claimed in claim 3, wherein the step of separating and purifying the extract comprises the following steps: and the extract enters a first-stage separator for cooling treatment, and then enters a second-stage separator for removing carbon dioxide to prepare the plant essential oil.
5. The method for extracting plant essential oil by using the supercritical extraction method as claimed in claim 4, wherein the plant raw material is derived from one or any combination of roots, stems, leaves, flowers, fruits and peels of fresh plants.
CN201910640326.3A 2019-07-16 2019-07-16 Extraction additive and method for extracting plant essential oil by using supercritical extraction method Active CN110396456B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910640326.3A CN110396456B (en) 2019-07-16 2019-07-16 Extraction additive and method for extracting plant essential oil by using supercritical extraction method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910640326.3A CN110396456B (en) 2019-07-16 2019-07-16 Extraction additive and method for extracting plant essential oil by using supercritical extraction method

Publications (2)

Publication Number Publication Date
CN110396456A CN110396456A (en) 2019-11-01
CN110396456B true CN110396456B (en) 2022-06-21

Family

ID=68325647

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910640326.3A Active CN110396456B (en) 2019-07-16 2019-07-16 Extraction additive and method for extracting plant essential oil by using supercritical extraction method

Country Status (1)

Country Link
CN (1) CN110396456B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116077551A (en) * 2023-02-24 2023-05-09 马鞍山市食品药品检验和药品不良反应监测中心 Supercritical fluid CO 2 Method for extracting senna leaf effective component

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0171079A2 (en) * 1984-08-09 1986-02-12 Siegfried Prof. Dr. Peter Process for extracting oil from oil-bearing vegetable products
CN104194762A (en) * 2014-08-04 2014-12-10 中国石油大学(北京) Supercritical CO2 microemulsion and method for improving oil recovery factor
CN109608595A (en) * 2018-12-21 2019-04-12 江苏海伦隐形眼镜有限公司 Silicon-containing surfactant, silicone-hydrogel treatment fluid and preparation, processing method

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5137538B1 (en) * 1971-03-31 1976-10-16
CN105257264A (en) * 2015-10-14 2016-01-20 中国石油天然气股份有限公司 Method for improving carbon dioxide flooding recovery ratio by using surfactant
CN108467789A (en) * 2018-05-16 2018-08-31 杭州更蓝生物科技有限公司 A kind of extraction process of Rosa Damascana

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0171079A2 (en) * 1984-08-09 1986-02-12 Siegfried Prof. Dr. Peter Process for extracting oil from oil-bearing vegetable products
CN104194762A (en) * 2014-08-04 2014-12-10 中国石油大学(北京) Supercritical CO2 microemulsion and method for improving oil recovery factor
CN109608595A (en) * 2018-12-21 2019-04-12 江苏海伦隐形眼镜有限公司 Silicon-containing surfactant, silicone-hydrogel treatment fluid and preparation, processing method

Also Published As

Publication number Publication date
CN110396456A (en) 2019-11-01

Similar Documents

Publication Publication Date Title
RU2566902C2 (en) Methods for extracting and isolating constituents of cellulose material
CN110373267B (en) Additive for extracting plant essential oil and extraction method of plant essential oil
CN112795430B (en) Extraction method for extracting Qilan agilawood essential oil
JP4424763B2 (en) Process for producing aromatic compounds by supercritical water treatment
Norkaew et al. Supercritical fluid extraction and gas chromatographic-mass spectrometric analysis of terpenoids in fresh kaffir lime leaf oil
CN110396456B (en) Extraction additive and method for extracting plant essential oil by using supercritical extraction method
CN106136302B (en) A kind of microcapsules aqueous two-phase purification process of cigarette caryophyllus oil and its application
CN111621365A (en) Zanthoxylum essential oil and extraction process thereof
Song et al. Meta‐analysis and review of cannabinoids extraction and purification techniques
CN103126062B (en) One grows tobacco composition extracting method
KR20110048401A (en) Method for preparing the extract fortified with chalcones from by-product of Angelica keiskei juice
CN110935191B (en) Method for extracting and purifying industrial hemp wax
CN110373270B (en) Additive for extracting plant essential oil and method for extracting plant essential oil
CN111303998A (en) Purification method of green pepper volatile oil
JP2010163363A (en) Method for producing extract containing apigenin in high concentration
CN111830145A (en) Method for determining feeding ratio and distillation time of black-branch rose hydrosol
CN111363626A (en) Holographic rose essential oil and green preparation method thereof
CN114041623B (en) Tobacco characteristic aroma component, preparation method and application thereof
Ramya et al. Process optimization of supercritical carbon dioxide (SC-CO2) extraction parameters for extraction of deoxynojirimycin (1-DNJ) from mulberry (Morus alba L.) leaves
CN109135927B (en) Flower essential oil extraction method
SI20143A (en) Procedure for the extraction of antioxidants from plants
Anuar et al. Production and extraction of Quercetin and (+)-Chatechin from Phyllanthus niruri callus culture
CN110373272B (en) Additive for removing plant wax and pretreatment method of plant raw material
CN111303997B (en) Green pepper extract and preparation method thereof
JP2006008552A (en) Method for producing flavanone compound

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant