TWI691355B - Method for extracting cinnamaldehyde-rich composition from cinnamon - Google Patents

Abstract

A method for extracting a cinnamaldehyde-rich composition from cinnamon, comprising: washing, drying, and then crushing cinnamon into pieces; pouring the pieces of cinnamon into an extraction tank of a subcritical propane fluid extraction device to perform subcritical propane fluid extraction; The obtained extraction fluid is introduced into a separation tank; the propane in the separation tank is removed to obtain a cinnamaldehyde-rich composition; wherein the extraction conditions of the subcritical propane fluid are: propane flow rate 8-15 liters/hour, extraction tank pressure 30 ~55 bar, extraction tank temperature 40~75℃.

Description

Method for extracting cinnamaldehyde-rich composition from cinnamon

The invention relates to a method for extracting a composition rich in cinnamaldehyde (Cinnamaldehyde), in particular to a method for extracting a composition rich in cinnamaldehyde from Cinnamomum wilfordii leaves.

Cinnamon root/bark/branch/leaf contains cinnamaldehyde, known extraction methods, nothing more than water extraction method, organic solvent extraction method, supercritical fluid extraction method.

Take the water extraction method as an example, for example: Taiwan Patent Application No. 099114436, which is extracted with distilled water in a boiling state; Taiwan Patent No. I463988, which is added with secondary water and boiled at a temperature range of 180 ℃ to 220 ℃ Cinnamon leaves to obtain extract; Taiwan patent No. I494117, continuous distillation by steam distillation method to obtain water extract containing cinnamaldehyde component; CN-201610660116.7 is extracted by steam; but because cinnamaldehyde is a hydrophobic substance, so These methods are not high in extraction efficiency, and the content of cinnamaldehyde in the extracted components is not high. CN-201210518917.1, CN-102964228B, CN-102964229B, CN-201210518899.7, CN-201210518963.1, CN-201220666255.8, CN-201220666403.6 use complex steam distillation equipment to extract cinnamaldehyde to improve yield, but the efficiency is still insufficient.

Take the solvent extraction method as an example, for example: Taiwan Patent No. 401394, extraction with methanol, CH ₂ N ₂ solution containing ether and the like, followed by chloroform distribution extraction; Taiwan Patent No. I495487, selected from ethanol , Propylene glycol, 1,3-butanediol, chloroform, dichloroethane, carbon tetrachloride, acetone, ethyl acetate, hexane, one or more extraction solvents for extraction; Taiwan Patent No. I549686, Cinnamon cinnamon is continuously extracted with methanol, and after three consecutive extractions, a methanol extract is obtained, and the methanol extract is distributed and extracted with methanol, water and n-hexane; CN-201710245493.9 extracts cinnamon with n-hexane as a solvent; but these organic The disadvantage of the solvent extraction method is that it is difficult to completely remove harmful organic solvents after extraction.

Take supercritical carbon dioxide extraction as an example, for example: Taiwan Patent No. I352611, which uses supercritical carbon dioxide to extract the fat-soluble essential oil components in the ground cinnamon leaf fragments; but the main component of the extract obtained by supercritical carbon dioxide extraction is essential oil The low content of cinnamaldehyde is not easy to separate from essential oils.

An object of the present invention is to provide a method for extracting a cinnamaldehyde-rich composition from cinnamon.

Another object of the present invention is to provide a method for extracting a cinnamaldehyde-rich composition from cinnamon leaves.

Another object of the present invention is to provide a method for extracting a cinnamaldehyde-rich composition from cinnamon using a subcritical propane fluid extraction method.

Another object of the present invention is to provide a method for extracting a cinnamaldehyde-rich composition from cinnamon leaves by using a subcritical propane fluid extraction method.

In the present invention, the subcritical propane fluid extraction method is first used to extract cinnamon to obtain a composition rich in cinnamaldehyde. The technical features of this method are: (1) subcritical propane fluid extraction of cinnamon (especially jade laurel leaves), which can efficiently obtain the composition of cinnamaldehyde; (2) subcritical propane fluid extraction of cinnamon (especially jade laurel leaves), which can be obtained A composition rich in cinnamaldehyde; (3) Extracting cinnamon (especially jade laurel leaves) with subcritical propane fluid at a specific temperature and pressure to recover propane, achieving low cost and environmental protection.

The present invention refers to a method for extracting a cinnamaldehyde-rich composition from cinnamon, which includes: Wash, dry and crush the cinnamon into pieces; Pour the cinnamon pieces into the extraction tank of the subcritical propane fluid extraction equipment to perform subcritical propane fluid extraction to obtain an extraction fluid; Lead the obtained extraction fluid into a separation tank; The propane in the separation tank is removed to obtain a cinnamaldehyde-rich composition; Its characteristics are as follows: the extraction conditions of subcritical propane fluid are: propane flow rate 8-15 liters/hour, extraction tank pressure 30-55 bar, extraction tank temperature 40-75°C.

The above-mentioned cinnamon refers to the cinnamon root/branch/bark/leaf of the genus Cinnamomum, especially the cinnamon leaf. The above-mentioned cinnamons are Cinnamomum cassia, Cinnamomum burmannii, Cinnamomum tamala, Cinnamomum pedunculatum, Cinnamomum osmophloeum, Cinnamomum subavenium, Ceylon cinnamon (Cinnamomum verum), Cinnamomum iners, Yunnan cinnamon (Cinnamomum glanduliferum), Philippine cinnamon (Cinnamomum philippinense), etc. are preferred, Cinnamomum cassia, Cinnamomum cassia, Cinnamomum burmannii are more preferred. Cinnamomum cassia is the best.

The so-called fragments mentioned above are just to improve the extraction effect. The fragments are too large and the extraction effect is poor. Generally speaking, 1-100 square millimeters (mm ² ) is better.

The pressure of the extraction tank is preferably 30 to 55 bar, preferably 35 to 50 bar, and more preferably 40 to 47 bar.

The so-called extraction tank temperature is 40 to 75°C, preferably 45 to 70°C, and more preferably 55 to 65°C.

The flow rate of propane is preferably 8 to 15 liters/hour, preferably 9 to 13 liters/hour, and more preferably 11.5 to 12.5 liters/hour.

The pressure of the separation tank may be not lower than the pressure of the propane storage tank, and generally 8 to 10 bar.

The temperature of the separation tank may be higher than the boiling point of propane. Generally, a temperature above room temperature is used, preferably 45 to 60°C.

The subcritical extraction equipment of the present invention is slightly as shown in FIG. 1a, where 100 is a propane storage tank for storing propane; 200 is an extraction tank for placing cinnamon (especially jade cassia) to be extracted, After the critical propane fluid, subcritical propane fluid extraction is performed to extract the cinnamaldehyde-rich composition to form a cinnamaldehyde-rich propane (subcritical fluid) solution; 500 is the propane between the propane storage tank 100 and the extraction tank 200 For the further description of the conveying device, please refer to the description of FIG. 1b; 300 is a separation tank for removing propane in the extract of cinnamon-rich cinnamaldehyde (especially jade laurel) to form a cinnamaldehyde-rich composition; 600 is The controller between the extraction tank 200 and the separation tank 300 is generally a control valve to introduce the extraction liquid in the extraction tank 200 into the separation tank 300; 400 is a propane recovery device between the propane storage tank 100 and the separation tank 300. The propane discharged from the separation tank 300 is recovered, and the recovered propane is introduced into the propane storage tank 100.

FIG. 1b is a preferred example of a propane delivery device 500, which includes a check valve 510, a booster pump 520, and a preheater 530, wherein the booster pump 520 is used to pressure the propane storage tank 100 (generally 8 ~10 bar), pressurized to the pressure of extraction tank 200; check valve 510 is used to prevent propane from rushing to propane storage tank 100; preheater 530 is used to preheat propane to increase its temperature to extraction tank 200 temperature. The preheater 530 can also be changed into a hot water jacket, which surrounds the periphery of the extraction tank 200 to achieve the purpose of controlling the temperature of the extraction tank 200. In the same way, a hot water jacket can be added around the separation tank 300 to achieve the purpose of controlling the temperature of the separation tank 300.

The extraction tank 200 preferably has a discharge valve (not shown) at the top to remove the existing air. It is better to add a pressure detector, a temperature detector, a propane concentration detector, a safety valve, an electric water microcomputer controller (none of which are marked in the figure), etc., to control the pressure/temperature and separation of the extraction tank 200 Pressure/temperature of tank 300, pressure of propane storage tank 100, and prevent gas explosion. Preliminary examples:

Extract 350 grams (g) of Cinnamon leaves for 3 hours using traditional hexane extraction to ensure that cinnamaldehyde is completely extracted. After removing hexane, the cinnamaldehyde content was measured to be 1.8 g. Example 1:

The leaves of Cinnamomum cassia are washed, dried, and then crushed into pieces of 1-10 mm.

實施例2~14 Weigh 350 grams of laurel leaf fragments and pour into the extraction tank of the subcritical propane fluid extraction equipment, and then in sequence: determine the raw air evacuation of the pump, extraction tank, separation tank and other paths; inject propane at the same pressure as the propane storage tank ( 8 bar); set the extraction conditions as follows: propane flow rate 12 liters/hour, extraction tank pressure 45 bar/temperature 60°C, separation tank pressure 8-10 bar/temperature 50°C. Propane subcritical extraction was carried out under the above conditions for 2 hours to obtain 3.7 g of product. The GC-MS spectrum is shown in Figure 2. The main components are: cinnamaldehyde content about 42%, extraction rate 86.3% (3.7x0.42/1.8); Main ingredients: o-methoxycinnamic aldehyde (o-methoxycinnamic aldehyde) is about 11.2%, methyl stearate (Methyl stearate) is about 14.9%, coumarin (coumarin) is about 7.9%; other ingredients are shown in Table 1. Table 1: Composition data table of supercritical fluid extract of Cinnamon Leaf

Example 2~14

Similar to Example 1, except that the subcritical extraction conditions are slightly different, see Table 2, and the amount of product obtained also see the table below. The GC-MS spectra of Examples 8, 9, 12, and 13 are shown in Figs. 3, 4, 5, and 6, respectively, in which the cinnamaldehyde content is about 36-42%, and the yield is about 2.5-3.5 g. Table 2: Propane flow rate (L/hr), extraction tank pressure (bar), extraction tank temperature (°C), and product weight (g) in Examples 1 to 13.

There are 16 main components, minor components, and other detected components in Examples 2-13, all of which are the same as those in Example 1, and the ratios are similar. Compare Figures 3, 4, 5, and 6 with Figure 2 respectively. Can be confirmed. In addition, Example 8 has a cinnamaldehyde content of 36% and a yield of 2.5; Example 9 has a cinnamaldehyde content of 39% and a yield of 2.7 g; Example 12 has a cinnamaldehyde content of 40% and a yield of 2.9 g; Example 13 has a cinnamaldehyde content of 42%, The yield is 3.3g; compared with the cinnamaldehyde content of Example 1, 42%, and the yield of 3.7g, although it is slightly inferior, it still has industrial value. Comparative example:

Similar to Example 1, except that the extraction tank has a pressure of 15 bar and a temperature of 40°C, and the separation tank has a pressure of 8 to 10 bar and a temperature of 40°C. The extraction result yielded only 1.8 grams of product, and the cinnamaldehyde content was only 16%. The GC-MS spectrum is shown in FIG. 7. The main components, minor components, and other detected components are very different from those in Example 1. The yield and cinnamaldehyde content of the comparative examples are also significantly lower than those of examples 1 to 13.

100: Propane storage tank 200: extraction tank 300: separation tank 400: Propane recovery unit 500: propane delivery device 510: Check valve 520: Supercharged pump 530: Preheater 600: control valve

FIG. 1a is a schematic block diagram of the subcritical fluid extraction device of the present invention. FIG. 1b is a further block diagram of the propane delivery device 500 in FIG. 1a. 2 is a GCMS chart of the cinnamaldehyde-rich composition extracted in Example 1. FIG. FIG. 3 is a GCMS chart of the cinnamaldehyde-rich composition extracted in Example 8. FIG. 4 is a GCMS chart of the cinnamaldehyde-rich composition extracted in Example 9. FIG. 5 is a GCMS spectrum of the cinnamaldehyde-rich composition extracted in Example 12. FIG. 6 is a GCMS spectrum of the cinnamaldehyde-rich composition extracted in Example 13. FIG. 7 is a GCMS chart of the cinnamaldehyde-rich composition extracted in the comparative example.

100: Propane storage tank

200: extraction tank

300: separation tank

400: Propane recovery unit

500: propane delivery device

600: control valve

Claims (14)

A method for extracting a cinnamaldehyde-rich composition from cinnamon, which includes: Wash, dry and crush the cinnamon into pieces; Pour the cinnamon pieces into the extraction tank of the subcritical propane fluid extraction equipment to perform subcritical propane fluid extraction to obtain an extraction fluid; Lead the obtained extraction fluid into a separation tank; The propane in the separation tank is removed to obtain a cinnamaldehyde-rich composition; Its characteristics are as follows: the extraction conditions of subcritical propane fluid are: propane flow rate 8-15 liters/hour, extraction tank pressure 30-55 bar, extraction tank temperature 40-75°C. The extraction method as described in item 1 of the patent application scope, wherein the propane flow rate is 9 to 13 liters/hour. The extraction method as described in item 2 of the patent application scope, wherein the propane flow rate is 11.5 to 12.5 liters/hour. The extraction method as described in item 1 of the patent application scope, wherein the extraction tank pressure is 35-50 bar. The extraction method as described in item 4 of the patent application range, wherein the extraction tank pressure is 40 to 47 bar. The extraction method as described in item 1 of the patent application, wherein the temperature of the extraction tank is 45 to 70°C. The extraction method as described in item 6 of the patent application scope, wherein the temperature of the extraction tank is 55~65°C. The extraction method as described in item 1 of the patent application scope, wherein the size of the cinnamon pieces is 1-100 mm ² . The extraction method as described in item 1 of the patent application, wherein the part of the cinnamon is the leaf. The extraction method as described in item 1 of the patent application, wherein the cinnamon is selected from Cinnamomum cassia, Cinnamomum burmannii, Cinnamomum tamala, Cinnamomum pedunculatum, Cinnamomum osmophloeum, Cinnamomum subavenium, Cinnamomum verum, Cinnamomum iners, Cinnamomum iners, Cinnamomum glanduliferum, and Cinnamomum philippinense By. The extraction method as described in item 10 of the patent application scope, wherein the cinnamon is at least one selected from the group consisting of Cinnamomum cassia and Cinnamomum burmannii. The extraction method as described in item 11 of the patent application scope, wherein the cinnamon refers to Cinnamomum cassia. The extraction method as described in item 1 of the patent application, wherein the pressure of the separation tank is 8-10 bar. The extraction method as described in item 1 of the patent application scope, wherein the temperature of the separation tank is 45-60°C.

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