JPH09217085A - Modified mint oils and the production of the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a modified mint oil useful as food and drink, medicine, etc., capable of easy preparation of desired flavor composition free from depleted material, unpleasant odor or unpleasant taste, flavor like a hogweed, resinous material, etc., by carrying out the contact and extraction of a specific crude mint oil with super critical carbon dioxide at a specific temperature and pressure. SOLUTION: This modified mint oil is obtained by carrying out the contact of (A) the crude mint oil obtained by steam distillation of mints with (B) super critical carbon dioxide at 35-100 deg.C, under pressure of 76-350kg/cm<2> , in some cases the continuos contact is repeated under the combination of the same temperature and pressure, to remove (C) the unpleasant odor or unpleasant taste, unstable terpene hydrocarbon, hogweed flavor, resinous material by fractional extraction.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to jelly, extracts, beverages and foods such as beverages, chewing gum, jelly confectionery and other confectionery, toothpaste, refreshing agent, mouthwash, oral drug and topical drug. TECHNICAL FIELD The present invention relates to a mint flavoring as a flavoring material used for general chemicals such as and the like and favorite products such as tobacco, and a manufacturing method thereof.

[0002]

2. Description of the Related Art As a method for modifying the flavor of mint oils such as peppermint oil, peppermint oil and spearmint oil,
Previously, the following methods were known.

(1) Mint oils are subjected to fractional distillation under reduced pressure or steam distillation to remove malodorous substances and high-boiling pitch present in the low-boiling portion, or to mint oils to obtain their acid value. A method of adding steam in excess of the amount necessary for neutralization and steam-distilling to neutralize, hydrolyze or polymerize malodorous and bitter substances to remove them.

(2) A method of adsorbing malodorous substances and resinous substances by adding powdered activated carbon to mint oils and stirring, or passing mint oils through a layer of granular activated carbons to remove them.

(3) A method of reacting mint oil with sodium hydrogen sulfite or an aqueous solution of sodium sulfite to form an addition compound with aldehyde and α, β-unsaturated ketones in the oil and removing it.

(4) A method of reacting mint oil with maleic anhydride to form an adduct with mentofuran in the oil and removing the adduct.

(5) A method in which mint oils are reacted with an oxidizing agent or a Fehling's reagent to oxidatively decompose unsaturated compounds and aldehydes in the oil.

(6) A method of adding a photosensitizer to mint oils and oxidizing and removing mentofuran by light irradiation.

(7) A method of reducing a malodorous substance by causing a small amount of a metal hydrogen complex compound (sodium borohydride) to act on mint oils.

(8) A method of reducing odorous substances by causing mint oils to act on aluminum powder or nickel-aluminum powder in an aqueous sodium hydroxide solution.

On the other hand, as a reforming method related to the supercritical extraction method, which is a key technique in the present invention, (9) use supercritical carbon dioxide from fresh or dried mint plant raw material A method for producing a mint type flavor oil improved by an extraction method.

The above-mentioned conventional techniques described as a method for modifying the flavor of mint oils are functionally characterized by fractionation, neutralization reaction,
It is classified into adsorption, addition reaction, oxidation reaction and reduction reaction.
These means often require separation fractionation by vacuum distillation or steam distillation after the reaction treatment, or often use some of these methods together.

Therefore, in these reforming methods, it was necessary to consider the following points in actual implementation.

1. Do not impair the natural flavor of mint oils due to by-products associated with the reaction or changes in heat during the process.

2. There should be no risk in applying reagents or methods.

3. Being able to do it with simple equipment and operation.

4. Manage the process so that it does not cost much.

And the like.

However, even with the conventional means and conditions for implementation in consideration of such points, there are still the following defects and problems.

In the method of passing through the vacuum distillation and steam distillation steps, certain components in mint oils tend to be oxidized or hydrolyzed due to the high temperature required for distillation, so-called heating odor is generated. Therefore, the flavor of the mint oils, which is the object of acquisition, will be significantly adversely affected, and the method that requires a large amount of deodorant and adsorbent, and the method that uses sulfite and heavy metals, Would increase production costs, and it was hard to say that it was eligible.

Further, the method using a metal-hydrogen complex compound has a problem that the reagent is expensive and is likely to change during storage.

In the method for directly producing mint oils from a raw material plant by supercritical carbon dioxide extraction, the cost of transporting a bulky raw material having a small oil content and the quality control during the transportation of a plant raw material which is easily altered are appropriately controlled. Due to the complexity of performing it, from such a viewpoint, its usefulness was evaluated only when it was carried out in the vicinity of the plant production site, and it was not suitable for purifying and producing only the required amount when necessary.

In addition, in the method for directly producing mint oils by supercritical carbon dioxide extraction from a plant raw material having a low oil content, the yield is low and continuous extraction is difficult. However, the manufacturing cost was high.

[0024]

The present invention provides a crude natural mint oil produced by steam distillation from mint plants,
The mint plant used as a raw material for modifying the flavor of the product for use as a food flavor is Mentha piperita (Mentha piperita).
), Mentha spicata and Mentha arvensis, and the natural mint oils extracted from them are peppermint oil, spearmint oil and mint oil, respectively.

In contrast to these mint oils, the present invention removes unpleasant odor or unpleasant taste (flavor), bitter substances, weed-like aroma, and resinous substances, thereby providing a cooler, cleaner and natural flavor and aroma. In order to obtain a product that does not have deterioration due to oxidation or heat deterioration, it is possible to fractionally concentrate flavor components suitable for flavoring, thereby flavoring foods, chewing gum, confectionery. Kind,
Toothpaste, jelly, extract, beverage, mouthwash and medicine,
It is intended to be modified into a more excellent fragrance when adding flavor to tobacco and the like.

In this case, it is intended to improve the defects and problems found in the above-mentioned conventional example, and more specifically, the separation of the solvent and the extract is easy, and the product is also used. The solvent does not remain, and unpleasant odor or unpleasant taste (flavor) in crude natural mint oil produced by steam distillation of plants, unstable terpene hydrocarbons, weedy aroma, and resinous substances are removed. It does not contain odor caused by heating.
It seeks to obtain flavors with a cooler, cleaner, natural flavor and aroma.

[0027]

[Means for Solving the Problems] Crude mint oils at a temperature of 35
By contacting with supercritical carbon dioxide in the pressure range of 76 to 350 kg / cm ² in the range of 〜 100 ℃, unpleasant odor or taste in crude mint oils, unstable terpene hydrocarbons, weedy aroma The resinous substance is fractionated and removed.
As a result, the extracted refined mint oil can have a cooler, cleaner and natural flavor and aroma, and can be prevented from deterioration due to oxidation and deterioration due to heating.

The carbon dioxide used in the present invention has a temperature of 35 to
It is in a supercritical state at 100 ℃ and a pressure of 76 to 350 kg / cm ² , and the extraction fraction consists of selectively extracting volatile unpleasant odor components and unstable monoterpenes under initial extraction conditions. After removal, mint oils with a more refined flavor are extracted under the latter extraction conditions. At the time of this extraction, the unextracted nonvolatile unpleasant flavor component and the resinous substance are removed as an extraction residue.

Under the above extraction initial conditions, carbon dioxide is used in a state of achieving selective extraction of components. That is, in this case, the supercritical carbon dioxide has a larger dissolving power as the pressure increases, but in the case of the other-side mint oils, the supercritical carbon dioxide phase and the oil phase become one phase at high pressure, and the selective two-phase Separation becomes impossible. Therefore, in using supercritical carbon dioxide, in order to classify into two-phase state, the extraction conditions are, for example, 76 to 80 kg / cm ² at 35 ° C. and 76 to 9 at 40 ° C.
3kg / cm ² , 76-103kg / cm ² at 50 ° C, 85-150kg / at 100 ° C
Use temperature and pressure stepwise, such as cm ² . To avoid thermal deterioration, temperature 35 ~ 70 ℃, pressure 76 ~ 120kg / cm
It is preferable to carry out in the range of ² .

In the subsequent extraction late conditions, carbon dioxide is used in a state having a higher dissolving power than the initial conditions. That is,
Use temperature in the range of 35 to 100 ° C and pressure in the range of 150 to 350 kg / cm ² . At this time, in order to avoid thermal deterioration, it is preferable that the temperature is 35 to 70 ° C. and the pressure is 150 to 350 kg / cm ² .

The reason is that the extraction temperature is 35 ° C. and the extraction pressure is 76 kg /
Under conditions up to the critical point below cm, the solubility of crude menthol in carbon dioxide is extremely low, the efficiency of selective two-phase separation is extremely poor, and it is not preferable as an extraction condition. Further, in any temperature range below the critical point, carbon dioxide and crude mint oil become one phase at any pressure, and the selective two-phase separation action itself, which is the object of the present invention, cannot be performed. On the other hand, the extraction temperature is 1
Above 00 ° C., too, the solubility of crude mint oils in carbon dioxide is low, but in this case high pressures cannot be used to increase the efficiency of the selective two-phase separation. However, although it is not impossible to create this condition in the implementation room, it is considered to be extremely unpractical when considering the excessive capital investment in the pressure resistance device and the operational complexity. However, it cannot be said that the extraction conditions are preferable for carrying out the present invention.

[0032]

EXAMPLES The present invention will be described below by exemplifying an embodiment carried out by using the apparatus shown in the drawings. However, the apparatus of the present invention is not limited to this, and a continuous extraction apparatus can be used. It can also be implemented in an embodiment.

FIG. 1 shows an example of a device for implementing the invention. In the figure, 10 and 11 are water baths, and mint oil as a raw material is charged into the extraction tank 4 housed in the water bath 10 heated to the extraction temperature. Carbon dioxide to carbon dioxide cylinder 1
To the liquid coal supply pump 3 through the subcooler 2 to increase the extraction pressure to a required level, and then to the raw material mint oil from the sintering filter 9 in the lower part of the extraction tank 4 through the conduit in the water bath 10. . By introducing carbon dioxide gas, the carbon dioxide gas is released upward while bubbling the raw mint oil from the lower part of the extraction tank 4, but the carbon dioxide solution in which the extract is dissolved is separated from the upper part of the extraction tank 4 by the separation tank. Sent to 5. The pressure in the extraction tank 4 is adjusted by the pressure-holding valve 6 and the pressure in the separation tank 5 is adjusted by the pressure-holding valve 7, and each of the pressure-holding valves is heated by an embedded heater in order to avoid cooling due to expansion heat during depressurization. Supply. The carbon dioxide decompressed in the separation tank 5 flows out to the outside via the flow meter 8, and the extract in the separation tank 5 is collected from the extract withdrawal valve 13. At the end of the extraction, the residue in the extraction tank 4 is decompressed to normal pressure and then extracted.
From the withdrawal valve 12. In the illustrated apparatus, the water baths 10 and 11 and the pressure-holding valves 6 and 7 are in the middle of extraction, and their temperatures and pressures and the separation temperature and pressure are changed during the extraction work by adjusting the water baths 10 and 11, respectively. Is possible.

An actual example of the manufacturing method of the present invention carried out using the above apparatus will be specifically described below.

Example 1 Raw material Madras crude peppermint oil (250 g) was charged into the extraction tank 4, and a mixture of the raw crude mint oil and carbon dioxide existed in a two-phase state at 40 ° C. under a condition of 83 kg / cm ² . While supplying carbon dioxide at a rate of 600 g / h, the extraction operation was continued until the weight ratio of carbon dioxide to the raw crude mint oil was 0.3. In addition, while the extraction operation is being performed,
The separation tank 5 was kept under the conditions of 14 ° C. and 40 kg / cm ² . As a result of such an extraction operation, 2 g of a volatile unpleasant odor component and a weed-like aroma component portion extracted from the raw crude mint oil were obtained in the separation tank 5, and the extraction tank 4 was refined as an extraction residue portion. 245 g of the modified peppermint oil thus obtained was obtained.

Example 2 250 g of crude raw peppermint oil from Madras as a raw material was charged into an extraction tank 4, and a mixture of the raw crude mint oil and carbon dioxide existed in a one-phase state at 40 ° C. and 250 kg / cm ² conditions. While supplying carbon dioxide at a rate of 700 g / h, the extraction operation was continued until the weight ratio of carbon dioxide to the raw crude mint oil was 13. Separation tank 5 during the extraction operation
Was kept under the conditions of 14 ° C. and 40 kg / cm ² . As a result of such an extraction operation, 240 g of refined modified peppermint oil was obtained as an extract in the separation tank 5, and in the extraction tank 4,
As an extraction residue, 4 g of a high boiling resinous material in raw mint oil and an unpleasant taste component portion were obtained.

Example 3 Raw material Madras crude peppermint oil (250 g) was charged into the extraction tank 4, and a mixture of the raw crude mint oil and carbon dioxide existed in a two-phase state at 40 ° C. under a condition of 83 kg / cm ² . While supplying carbon dioxide at a rate of 600 g / hour, the extraction operation was continued until the weight ratio of carbon dioxide to the raw crude mint oil was 0.2. The separation tank 5 was kept under the conditions of 14 ° C. and 40 kg / cm ² during the extraction operation. As a result of such an extraction operation, as the first extract, in the separation tank 5,
1.7 g of volatile unpleasant odor components and weed-like aroma components extracted from raw mint oil were obtained. This first from the separation tank 5
After extracting and discarding the extract, subsequently, in order to efficiently operate the step of separating the high boiling point resinous substance and the unpleasant taste component from the raw crude mint oil, the extraction conditions of the extraction tank are mint oil and carbon dioxide. The mixture exists in a single-phase state at 40 ° C, 250k
While changing to g / cm ² and supplying carbon dioxide at a rate of 700 g / h, the weight ratio of carbon dioxide to the raw crude mint oil is 13.7.
The extraction operation was continued until. During this extraction operation, the separation tank 5 kept it under the conditions of 14 ° C. and 40 kg / cm ² . As a result of such an extraction operation, the refined modified mint oil 23 in the separation tank 5 is obtained as the second extract.
7 g was obtained, and from the extraction tank 4, 6 g of a high-boiling resinous substance in the raw material crude mint oil and an unpleasant taste component portion were obtained as an extraction residue.

Example 4 Raw crude spearmint oil (Midwest Scotch)
250 g was charged into the extraction tank 4, and a mixture of this raw material crude mint oil and carbon dioxide exists in a two-phase state at 40 ° C. and 83 kg / cm ²
Under the conditions of, while supplying carbon dioxide at a rate of 500 g per hour, the weight ratio of carbon dioxide and raw crude mint oil is 0.
The extraction operation was continued until it reached 15. During this extraction operation, the separation tank 5 was kept under the conditions of 14 ° C. and 40 kg / cm ² . As a result of such an extraction operation, 3.0 g of a volatile unpleasant odor component and a weed-like aroma component portion extracted from the raw crude mint oil were obtained in the separation tank 5 as the first extract. After extracting the first extract from the separation tank 5 and discarding it, subsequently, in order to efficiently operate the step of separating the high boiling point resinous substance and the unpleasant taste component from the raw crude mint oil, the extraction conditions of the extraction tank are set. A mixture of mint oil and carbon dioxide exists in a one-phase state. At 40 ° C, change to 150 kg / cm ^2, and change carbon dioxide to 5 per hour.
While supplying at a rate of 70 g, the extraction operation was continued until the weight ratio of carbon dioxide and raw crude mint oil was 16.4. During this extraction operation, the temperature of the separation tank 5 is 14 ° C,
It was kept under the condition of 40 kg / cm ² . As a result of such an extraction operation, 227 g of refined modified spearmint oil was obtained in the separation tank 5 as the second extract, and from the extraction tank 4, as the extraction residue, the high boiling point resinous material in the raw crude mint oil was extracted. 13 g of the substance and the unpleasant taste component part were obtained.

Example 5 Raw crude spearmint oil (Midwest Scotch)
250 g was charged into the extraction tank 4, and a mixture of this raw material crude mint oil and carbon dioxide exists in a two-phase state at 40 ° C. and 83 kg / cm ²
Under the conditions of, while supplying carbon dioxide at a rate of 570 g / h, the weight ratio of carbon dioxide and raw crude mint oil is 0.
The extraction operation was continued until it reached 1. During this extraction operation, the separation tank 5 was kept under the conditions of 14 ° C. and 40 kg / cm ² . As a result of such an extraction operation, 5.4 g of a volatile unpleasant odor component and a weed-like aroma component portion extracted from the raw material crude mint oil were obtained in the separation tank 5 as the first extract. After extracting the first extract from the separation tank 5 and discarding it, the step of separating the high boiling point resinous material and the unpleasant taste component from the raw crude mint oil is efficiently operated to obtain the high boiling aroma of the raw crude mint oil. In order to extract the components more efficiently than in Example 4, the extraction conditions in the extraction tank were changed to 250 ° C., 250 kg / cm ² at 40 ° C. where the mixture of mint oil and carbon dioxide was present in a single phase,
While supplying carbon dioxide at a rate of 570 g / h, the extraction operation was continued until the weight ratio of carbon dioxide to the raw crude mint oil was 14.5. During the extraction operation, the separation tank 5
It was kept under the conditions of 14 ° C. and 40 kg / cm ² . As a result of such an extraction operation, 225 g of refined modified spearmint oil was obtained in the separation tank 5 as the second extract, and as the extraction residue from the extraction tank 4, the high-boiling resinous material in the raw crude mint oil was obtained. And 12 g of an unpleasant taste ingredient part were obtained.

An actual example of the manufacturing method of the present invention carried out by the countercurrent extraction method will be specifically described.

FIG. 2 shows an apparatus adapted to this countercurrent extraction method, and its embodiment is shown in the following embodiments 6, 7, and 8.
Will be described in detail.

In the first extraction, the raw material crude mint oil is supplied from the raw material container 20 to the extraction tower 15 in which the packing having the rectification effect is filled, by operating the raw material supply pump 16. Carbon dioxide passes from the carbon dioxide cylinder 1 through the supercooler 2,
The liquid is fed to the liquid coal supply pump 3 and the extraction pressure is increased, the temperature is raised to the extraction temperature by the heat exchanger 14, and the liquid is supplied to the extraction tower 15. The inside of the extraction column 15 is pre-filled with the extraction pressure of the first extraction condition and the supercritical carbon dioxide of the extraction temperature adjusted by the pressure maintaining valve 6 and the heater on the outer periphery of the column, and the extraction is started at the same time as the supply of the raw material. . Volatile unpleasant flavor components, terpene hydrocarbons, etc., which are components that are easily dissolved, are dissolved in supercritical carbon dioxide and transferred to the separation tank 19 through the pressure holding valve 6. Separation tank
The pressure inside 19 is adjusted to the separation condition pressure by the pressure holding valve 7.
In order to avoid cooling due to thermal expansion during depressurization, heat is supplied to the pressure-holding valves 6 and 7 by an embedded heater, and a heat exchanger is used.
Adjust to separation temperature with 18. The extract in the separation tank 19 is
Withdraw from the withdrawal valve 13. The extraction residue of the extraction tower 15 is extracted from the extraction residue extraction valve 12 and used for the next second extraction. If the flavor of the extraction residue matches the flavoring purpose, a second extraction is not performed and the extraction residue is used as a refined modified mint oil.

In the second extraction, instead of the raw crude mint oils, the extraction residue of the first extraction is used, the extraction pressure and the extraction temperature of the second extraction conditions are set, and the extraction is performed in the same manner as the first extraction. The extract in the separation tank 19 is extracted from the extraction valve 13 and used as a refined modified mint oil.

Example 6 Carbon dioxide was supplied from the lower part of the extraction column 15 packed with Dickson packing every hour under conditions of 40 ° C. and 83 kg / cm ² in which a mixture of crude mint oil and carbon dioxide was present in a two-phase state. While supplying at a flow rate of 7 kg, after the inside of the extraction tower 15 became stable, a raw material supply pump 16 was used to supply raw material Madras crude peppermint oil at a rate of 2 kg per hour to produce carbon dioxide and raw crude mint oil. Continuous countercurrent extraction was performed.
The separation tank 19 was kept under the conditions of 14 ° C. and 40 kg / cm ² , and the volatile unpleasant odor and the weed-like aroma component extracted from the crude mint oil were extracted from the lower extraction valve 13 of the separation tank 19 and discarded.
The extraction residue remaining at the bottom of the extraction tower 15 was extracted from the extraction valve 17 at the bottom to obtain a purified modified peppermint oil.

Example 7 A mixture of mint oil and carbon dioxide exists in a one-phase state.
Under the conditions of 40 ° C. and 150 kg / cm ² , while supplying carbon dioxide from the lower part of the extraction column 15 filled with Dickson packing at a rate of 7 kg / h, after the inside of the extraction column 15 became stable, the raw material supply pump 16 The raw material Madras crude peppermint oil was fed at a rate of 2 kg / hr to perform continuous countercurrent extraction of carbon dioxide and the raw crude mint oil. Keep the separation tank 19 under the conditions of 14 ° C and 40 kg / cm ²
The extract separated from the carbon dioxide inside was extracted as a purified modified peppermint oil from an extraction valve 13 provided at the bottom of the separation tank 19. At the bottom of the extraction tower 15, the high-boiling resinous material separated from the raw crude mint oil and the unpleasant taste component remain as the extraction residue, but this extraction residue is
It was removed from the bottom extraction valve 17 of 15 and discarded.

Example 8 In the first extraction, the mixture of crude mint oil and carbon dioxide was 2
Under the conditions of 40 ° C and 83 kg / cm ² existing in a phase state,
While supplying carbon dioxide from the lower part of the extraction tower 15 filled with Dickson packing at a flow rate of 7 kg / hour, the inside of the extraction tower 15 was stabilized, and then 2 kg / hour of crude Madras crude peppermint oil as a raw material was supplied from the raw material supply pump 16. Was supplied at a rate of 10 to carry out continuous countercurrent extraction of carbon dioxide and the crude crude mint oil. The separation tank 19 was kept under the conditions of 14 ° C. and 40 kg / cm ² , and the volatile unpleasant odor and the weedy aroma component portion extracted from the crude mint oil were extracted from the lower extraction valve 13 of the separation tank 19 and discarded. The extraction residue remaining at the bottom of the extraction tower 15 was extracted from the extraction valve 12 into the extraction residue container 21.

In the subsequent second extraction, in order to efficiently extract the target modified mint oil, the extraction conditions are as follows: a mixture of mint oil and carbon dioxide is present in a one-phase state at 40 ° C., 150 kg /
The extraction was performed in the same manner as in the first extraction, except that the feedstock was the extraction residue obtained in the first extraction under this condition in place of cm ² . The extract separated from carbon dioxide in the separation tank 19 is a refined modified peppermint oil,
It was withdrawn from the withdrawal valve 13 at the bottom of the separation tank 19. At the bottom of the extraction tower 15, the high-boiling resinous material separated from the raw crude mint oil and the unpleasant taste component remain as the extraction residue, but this extraction residue was extracted from the extraction valve 17 and discarded.

In order to compare the extract of the present invention according to the above example with the conventional example, the following three experiments were conducted as comparative examples.

COMPARATIVE EXAMPLE 1 The same crude peppermint oil from Madras was steam-distilled according to a conventional method to remove the initially distilled portion (the yield of the oil portion was 3% based on the raw material), and the water portion and the oil of the subsequent distilled portion were removed. The oil portion (90% of the raw material ratio) was dehydrated with magnesium sulfate, and then filtered with filter paper to obtain a filtrate portion, which was used as a test peppermint oil.

Comparative Example 2 The same crude peppermint oil from Madras was rectified using a rectification column under a reduced pressure of 20 mmHg to remove the initial distillate part (ratio of raw material to 3%), and the subsequent distillate part (to 90% of the raw material) was used as the test peppermint oil.

Comparative Example 3 Purified spearmint oil was obtained in the same manner as in Comparative Example 1 using the same crude spearmint oil (Midwest Scotch) as the raw material.

In order to compare the product obtained by each of the above-mentioned examples according to the method of the present invention with the product obtained by each of the above-mentioned comparative examples, each sample was subjected to sensory test and determination by gas chromatography. It was

In the sensory evaluation, the raw material oil, the refined and refined oil by supercritical carbon dioxide extraction, the steam distillation treated oil and the vacuum distillation treated oil were evaluated by a flavoring agent to gum and water.

The evaluation was carried out by 10 trained sensory panelists.

A refreshing feeling, a good flavor, and a raw oil as a reference,
The strength and the degree of taste were evaluated. Overall score (maximum 7 points)
The results are shown in Table 1 below.

[0056]

[Table 1]

Using gas chromatography, dimethyl sulfide which is an offensive odor component, limonene which is an unstable monoterpene hydrocarbon component, 1,8-cineole, 3-octanol which is a bitter or unpleasant odor component, As a result of analyzing and comparing the content and compositional balance of mentofuran, menthol and menthol isomers, etc., it was found that there is a considerable correlation with the sensory test results.

[0058]

EFFECTS OF THE INVENTION According to the present invention, (1) because of low temperature treatment in carbon dioxide, deterioration due to oxidation or heating deterioration does not occur in the process.

(2) By selecting conditions for extraction and separation (temperature, pressure, amount of carbon dioxide, speed, etc.) and ratio of fractionation, any flavor component composition suitable for flavoring can be fractionally concentrated. it can.

(3) Removes unpleasant odor or unpleasant taste (flavor) in crude mint oil, unstable terpene hydrocarbons, weed-like aroma, resinous substances, does not contain heat-deteriorated odor, and is cooler and cleaner It is possible to obtain a flavor having a natural flavor and aroma.

(4) easy separation of solvent and extract,
It can be carried out without using any solvent which is not allowed to be used as a food, and carbon dioxide which is a solvent used in the practice of the present invention does not remain in the product at all and is safer.

[Brief description of drawings]

FIG. 1 shows an example of a product extracting device suitable for carrying out the manufacturing method of the present invention.

FIG. 2 shows an actual example of an apparatus in which the manufacturing method of the present invention is carried out by a countercurrent extraction method.

[Explanation of symbols]

 1 Carbon dioxide cylinder 2 Supercooler 3 Liquid coal supply pump 4 Extraction tank 5 Separation tank 6 Pressure-holding valve 7 Pressure-holding valve 8 Flow meter 9 Sintering filter 10 Water bath 11 Water bath 12 Extraction valve 13 Extraction residue discharge valve 14 Heat exchanger 15 Extraction tower 16 Raw material supply pump 17 Extraction valve 18 Heat exchanger 19 Separation tank 20 Raw material container 21 Extraction residue container

Claims (3)

[Claims] 1. A crude mint oil obtained by steam distillation of a mint plant is used at a temperature of 35 to 100 ° C. and a pressure of 76.
Modified mint oils extracted by contact with supercritical carbon dioxide in the region of ~ 350 kg / cm ² . 2. A crude mint oil obtained by steam distillation of a mint plant is used at a temperature of 35 to 100 ° C. and a pressure of 76.
Characteristic for removing unpleasant odor or taste in crude mint oils, unstable terpene hydrocarbons, weedy aroma, and resinous substances by contacting with supercritical carbon dioxide in the range of ~ 350 kg / cm ^2. A method for producing a modified mint oil. 3. A crude mint oil obtained by steam distillation of a mint plant is used at a temperature of 35 to 100 ° C. and a pressure of 76.
Contact with supercritical carbon dioxide in the range of ~ 350 kg / cm ² to remove unpleasant odor or taste in crude mint oils, unstable terpene hydrocarbons, weedy aroma, resinous substances at the above temperature. A method for producing a modified mint oil, which comprises fractionating and extracting refined mint oil in each step by changing combination conditions of a range and a pressure region in two or more extraction steps.