Process for producing purified essential oil

Abstract

It is provided a process for producing a purified essential oil excellent in safety and quality with high productivity from an essential oil comprising a harmful contaminant such as an agricultural chemical by simply and smoothly removing the contaminant with high removal rate without causing poor balance of flavor which the essential oil originally has, decrease of flavor strength and the like. It relates to a process for producing a purified essential oil by treating an essential oil comprising a contaminant with an active carbon to remove the contaminant and the removal rate of the contaminant is further improved by using an active carbon activated with a chemical, particularly an active carbon activated with zinc chloride, in the treatment, or by conducting the treatment at a low temperature of room temperature or lower, particularly at 25 C. to 5 C.

Claims

1. A process for producing a purified citrus oil, comprising a) contacting a citrus oil comprising a contaminant with an active carbon to prepare a suspension; b) stirring the suspension at a temperature of from 30 C. to 5 C. for 10 minutes to 2 hours; and c) recovering the purified citrus oil from which the contaminant is removed, wherein the active carbon is an activated active carbon activated with zinc chloride, wherein the contaminant is a residual agricultural chemical which is one kind or a mixture of two or more kinds selected from ortho-phenyl phenol, chloroneb, simazine, carbaryl, chlorpyrifos, imazalil, thiabendazole and diphenyl, wherein the active carbon is added in an amount of 0.5 to 10% by mass, based on the mass of the citrus oil comprising a contaminant, and wherein flavor and odor components of the citrus oil, selected from the group consisting of nootkatone, octanal, nonanal, decanal, dodecanal and linalool, remain unchanged in the obtained purified citrus oil.

2. The process for producing a purified citrus oil according to claim 1, wherein the citrus oil is one kind or a mixture of two or more kinds selected from lemon oil, sweet orange oil, bitter orange oil, lime oil, grapefruit oil, bergamot oil, mandarin oil, Yuzu oil (Citrus junos oil) and Sudachi oil (Citrus sudachi oil).

Description

MODE FOR CARRYING OUT THE INVENTION

(1) The present invention is described in detail below.

(2) The present invention relates to a process for producing a purified essential oil, comprising treating an essential oil comprising a contaminant with an active carbon, thereby removing the contaminant.

(3) The term contaminant used in the present description means substances that do not correspond to substances constituting a plant itself which is a raw material of an essential oil and substances derived from the substances (for example, substances formed by chemical change and alternation of substances constituting a plant), and is a generic name of substances that are harmful to humans and animals or substances that have a concern to be harmful.

(4) The kind of the contaminant contained in the essential oil is not particularly limited. Representative examples of the contaminant include agricultural chemicals, heavy metals, fungi, and toxins derived from fungus. Of those, the present invention is suitable for the removal of agricultural chemicals from the essential oil in which the agricultural chemicals remain therein.

(5) The kind of agricultural chemicals contained in the essential oil is not particularly limited, and can be any agricultural chemicals so long as it is agricultural chemicals capable of being removed by the process of the present invention. Examples of the agricultural chemicals include ortho-phenyl phenol, chloroneb, simazine, carbaryl, chlorpyrifos, imazalil, thiabendazole, diphenyl, trichlorfon, fenitrothion, prothiofos and methidathion. The agricultural chemicals contained in the essential oil may be any one kind of those, or may be two or more kinds of those.

(6) Of those, the process of the present invention is effective to the removal of agricultural chemicals such as ortho-phenyl phenol, chloroneb, simazine, carbaryl, chlorpyrifos, imazalil, thiabendazole and diphenyl, the residual agricultural chemicals thereof becoming the problem in the citrus oil, from the citrus oil comprising those agricultural chemicals, and is particularly suitable to the removal of ortho-phenyl phenol from the citrus oil comprising the ortho-phenyl phenol as residual agricultural chemicals.

(7) The kind of the essential oil used in the process of the present invention is not particularly limited, and any essential oil can be used so long as it is an essential oil that can achieve the object of the present invention. Above all, one kind or a mixture of two or more kinds of citrus oil, spice oil and herb oil is preferably used.

(8) More specifically, examples of the citrus oil include lemon oil, sweet orange oil, bitter orange oil, lime oil, grapefruit oil, bergamot oil, mandarin oil, Yuzu oil (Citrus junos oil) and Sudachi oil (Citrus sudachi oil).

(9) Examples of the spice oil include allspice, anise oil, star anise oil, bitter almond oil, blackcurrant oil, cinnamon oil, clove oil, ginger oil, mustard oil and pepper oil.

(10) Examples of the herb oil include sweet basil oil, celery oil, clary sage oil, eucalyptus oil, peppermint oil, mint oil and spearmint oil.

(11) The essential oil used in the present invention may consist of any one kind of the above-described oils, and may be a mixture of two or more kinds of those.

(12) The kind of a contaminant, particularly the kind of agricultural chemicals, contained in the essential oil, and the content of the contaminant vary depending on the kind of a plant which is a raw material of an essential oil, production area of a plant, cultivation method of plant, storage/distribution methods, a preparation method of an essential oil from a plant, and the like. For example, in the citrus oil obtained by a cold press method, ortho-phenol which is one kind of agricultural chemicals frequently remains in an amount of a range of from 0.01 to 70 ppm when measured with gas chromatograph/mass spectrometry-mass spectrometry (GC/MS-MS). The process of the present invention is extremely effective to the removal of ortho-phenyl phenol from citrus oil in which the ortho-phenyl phenol remains, obtained by the cold press method.

(13) In the process of the present invention, for example, powdery active carbon, granular active carbon (crushed carbon, granulate carbon, pelletized carbon), spherical active carbon and fibrous active carbon can be used as the active carbon. Of those, the powdery active carbon and/or the granular active carbon are preferably used from the points that the removal effect of a contaminant from an essential oil is high, and handling property, adsorption efficiency and economical efficiency are excellent.

(14) The origin of the active carbon used in the process of the present invention is not particularly limited. For example, active carbon produced using palm shell, woody material (sawdust, wood chip and the like), coal or petroleum can be used. Of those, the active carbon using palm shell or woody material as a raw material is preferably used from the viewpoints of safety and environmental pollution prevention when the purified essential oil is used in food uses.

(15) The active carbon used in the process of the present invention may be activated active carbon or may be non-activated active carbon. Of those, the activated active carbon shows high removal rate of a contaminant from the essential oil, and is therefore preferably used. Active carbon activated with a gas such as steam and active carbon activated with a chemical (zinc chloride, phosphoric acid or the like) can be used as the activated active carbon. Of those, the active carbon activated with a chemical, particularly, the active carbon activated with zinc chloride, shows higher removal rate of contaminant, particularly residual agricultural chemicals, from the essential oil, and is therefore preferably used.

(16) Although not limited, examples of the active carbon that can be used in the process of the present invention include Kyouryoku Shirasagi, Seisei Shirasagi and Tokusei Shirasagi (each is zinc chloride-activated powdery active carbon), manufactured by Japan EnviroChemicals, Ltd.; Shirasagi A, Shirasagi M, Shirasagi C and Shirasagi P (each is steam-activated powdery active carbon), manufactured by the same company; Shirasagi WH.sub.2c (steam-activated granular active carbon) manufactured by the same company; Kuraray Coal GL and Kuraray Coal GW (steam-activated active carbon: powdery and granular), manufactured by Kurary Chemical Co., Ltd.; Taiko S, Taiko SG and Taiko SGP (each is zinc chloride-activated powder active carbon), manufactured by Futamura Chemical Co., Ltd.; and Diahope S80S, manufactured by Calgon Mitsubishi Chemical Corporation.

(17) In producing a purified essential oil by removing a contaminant such as agricultural chemicals, contained in the essential oil with the active carbon, the following methods can be employed: a method for recovering a purified essential oil by adding active carbon to an essential oil comprising a contaminant, followed by stirring for a given time, and then separating the active carbon (batch method); and a method for recovering a purified essential oil by passing an essential oil comprising a contaminant through a column filled with the active carbon, thereby adsorbing the contaminant on the column (column method).

(18) In the case of producing the purified essential oil by the batch method, the active carbon is generally added in an amount of preferably 0.1% by mass or more, and more preferably from 0.5 to 20% by mass, based on the mass of the essential oil comprising a contaminant, although varying depending on the kind of the essential oil, the kind and the content of the contaminant in the essential oil, the kind of the active carbon, and the like. In the case where the content of the contaminant contained in the essential oil is the basis, it is preferred that the active carbon is added in an amount of from 20 to 3,000 parts by mass, particularly from about 50 to 1,500 parts by mass, per 1 part by mass of the contaminant.

(19) In the case of producing the purified essential oil by the column method, flow down rate and the like of the essential oil in the active carbon-filled column are adjusted according to the kind of the essential oil, the kind and the content of the contaminant in the essential oil, the kind of the active carbon, the filling amount of the active carbon in the column, and the like, so that the contaminant in the essential oil is sufficiently removed.

(20) In any of the batch method and the column method, the treatment time by the active carbon is preferably from 10 minutes to 5 hours.

(21) In removing the contaminant contained in the essential oil with the active carbon, the following methods can be employed. () A method of directly using the essential oil comprising the contaminant without diluting with a solvent and treating the same with the active carbon; () a method of mixing an edible solvent with the essential oil comprising the contaminant to dilute the essential oil, and treating the resulting dilute liquid with the active carbon; () a method of adding a non-edible solvent to the essential oil comprising the contaminant to dilute the essential oil, and treating the resulting dilute liquid with the active carbon; and () a method of diluting the essential oil comprising the contaminant with an essential oil free of a contaminant, and treating the resulting dilute liquid with the active carbon.

(22) In the case of employing the methods () and (), the purified essential oil obtained by the removal treatment of the contaminant with the active carbon can be directly used in the respective uses, or as may be necessary, the edible solvent as used in the method () is added to the essential oil, and the resulting dilute liquid can be used in the respective uses.

(23) Examples of the edible solvent used in the method () include ethanol, water, glycerin, medium-chain triglyceride and vegetable fat or oil. One kind or two or more kinds of those can be used. The edible solvent used here may be used in the respective uses in the form of an edible solvent solution of the purified essential oil without separating from the purified essential oil after completion of the removal treatment of the contaminant with the active carbon, or may be distilled away from the purified essential oil by distillation under reduced pressure, or the like.

(24) Examples of the non-edible solvent used in the method () include organic solvents such as hexane, ethyl acetate, acetone, butanol, propanol and methanol. One kind or two or more kinds of those solvents can be used. The non-edible solvent used here is distilled away by distillation under reduced pressure or the like after completion of the removal treatment of the contaminant with active carbon.

(25) In removing the contaminant by treating the essential oil comprising a contaminant with active carbon, the removal treatment is conducted in a range of a temperature that the temperature (liquid temperature) of an essential oil liquid comprising a contaminant or a diluted essential oil solution is higher than the coagulation point of the essential oil and volatilization of the essential oil is small, regardless as to whether the treatment is conducted by the batch method or the column method, and regardless as to whether the treatment is conducted by any one of the above () to (). Above all, the treatment with active carbon is conducted at a temperature such that the temperature (liquid temperature) of the essential oil or the essential oil solution, comprising a contaminant is a range of from 30 C. to 5 C., preferably from 25 C. to 5 C., and particularly preferably from 25 C. to 2 C. By employing the temperature, the contaminant can be smoothly removed with higher removal rate.

(26) The purified essential oil obtained by the process of the present invention does not have poor balance of flavor and decrease in flavor strength, maintains flavor and flavor strength that the essential oil originally has, has excellent flavor, does not contain contaminant or if contained, contains an extremely slight amount to an extent of not impairing humans and animals. Therefore, the purified essential oil has excellent safety.

(27) The purified essential oil obtained by the process of the present invention may be used as a flavor material without any modification, or may be used in the form of a flavor composition by appropriately combining with the conventional other flavor materials. The kind and the blending ratio of the other flavor material in the combination are not particularly limited, and in response to the kind and the like of the purified essential oil obtained by the process of the present invention, other flavor materials adapting thereto can be appropriately selected and used.

(28) Various foods, drinks, and oral care products can be prepared using the purified essential oil obtained by the process of the present invention and/or a flavor composition obtained by blending the purified essential oil with the other flavor materials. Examples of the food or drink include drinks such as fruit juice drink, sports drink, carbonated drink, milk beverage, teas drink, alcoholic drinks and health drink; frozen sweets such as ice creams, sherbets and ice candies; favorite foods such as Japanese and western confectioneries, chewing gums, chocolates, breads, coffee and tea; foods or drinks such as various snacks; and candies, although not limiting thereto. Examples of the oral care products include dentifrice, dental rinse, gingival massage cream, local endermic liniment, lozenge and chewing gum.

EXAMPLES

(29) The present invention is described specifically below by Examples and the like, but it should be understood that the invention is not limited to the following Examples and the like.

(30) In the following Examples and Comparative Examples, quantitative determination of residual agricultural chemicals (ortho-phenyl phenol) in the essential oil (various citrus oils) and quantitative determination of each ingredient contained in the essential oil (each flavor ingredient) were conducted by gas chromatograph/mass spectrometry-mass spectroscopy (GC/MS-MS) employing the following apparatus and conditions.

(31) Apparatus and Condition Relating to GC/MS-MS

(32) GC model name: Agilent Technologies HP6890N, manufactured by Agilent Technologies

(33) GC column name: DB-5MS (30 m0.25 mm I.D., thickness: 0.25 m), manufactured by Agilent Technologies

(34) MS model name: Quatro micro GC, manufactured by Micromass

(35) GC Conditions Injection method: Splitless Injection amount: 2 L Injection inlet temperature: 250 C. Column temperature: 50 C. for 1 minute.fwdarw.Heating to 125 C. at 15 C./min.fwdarw.Heating to 300 C. at 5 C./min, and then maintaining at 300 C. for 9 minutes Flow rate: 1.0 ml/min

(36) MS-MS Conditions Ion source temperature: 180 C. Ionization method: EI+ mode Ionization voltage: 70 eV

(37) In the following Examples and Comparative Examples, the removal rate of ortho-phenyl phenol from the essential oil (each citrus oil) was obtained by the following mathematical formula (1):
Ortho-phenyl phenol removal rate (%)={(A.sub.0A.sub.1)/A.sub.0}100(1)
wherein A.sub.0 is the content (ppm) of ortho-phenyl phenol in an essential oil (citrus oil) before purification treatment, and A.sub.1 is the content (ppm) of ortho-phenyl phenol in an essential oil (citrus oil) after purification treatment.

Examples 1 to 3 and Comparative Examples 1 and 2

(38) (1) Five kinds of adsorbents shown in Table 1 were added to 5 g of grapefruit cold press oil in which ortho-phenyl phenol remains (ortho-phenyl phenol concentration=49.1 ppm) respectively in an amount of 1% by mass, 2% by mass, 4% by mass or 8% by mass, based on the mass of the grapefruit cold press oil, followed by well suspending and then stirring at room temperature (25 C.) for 1 hour. The adsorbent was filtered to recover the grapefruit cold press oil.

(39) (2) The content of ortho-phenyl phenol in the grapefruit cold press oil after the treatment with the adsorbent, recovered in (1) above was analyzed with GC/MS-MS by the method described above, and removal rate (%) of the ortho-phenyl phenol was obtained according to the mathematical formula (1) above. The results obtained are shown in Table 1.

(40) TABLE-US-00001 TABLE 1 Removal Rate (%) of Ortho-Phenyl Phenol Comparative Comparative Example 1 Example 2 Example 3 Example 1 Example 2 Kind of adsorbent Seisei Shirasagi.sup.1) Shirasagi A.sup.2) Kuraray Coal Silica gel 3A.sup.4) POLYCLAR (Active carbon) (Active carbon) GM.sup.3) (Silica gel) PLUS 730.sup.5) (Active carbon) (Polyvinyl pyrrolidone) Amount of adsorbent added 1% by mass 14 11 14 13 11 2% by mass 33 25 22 2 10 4% by mass 47 33 37 0 14 8% by mass 69 44 53 0 27 .sup.1)Manufactured by Japan EnviroChemcials, Ltd. (Zinc chloride-activated powdery active carbon) .sup.2)Manufactured by Japan EnviroChemcials, Ltd. (Steam-activated powdery active carbon) .sup.3)Manufactured by Kuraray Chemical Co., Ltd. (Steam-activated powdery active carbon) .sup.4)Manufactured by Fuji Silysia Chemical Ltd. (Crushed silica gel) .sup.5)Manufactured by ISP Japan Ltd. (Polyvinyl pyrrolidone)

(41) (3) As shown in Table 1, in Examples 1 to 3, by treating the grapefruit cold oil in which ortho-phenyl phenol (agricultural chemical) remained therein with active carbon, the removal rate of the ortho-phenyl phenol was greatly increased as compared with Comparative Examples 1 and 2 in which the grapefruit cold press oil was treated with other adsorbent comprising silica gel or polyvinyl pyrrolidone.

(42) Above all, in Example 1, by using Seisei Shirasagi which is active carbon activated with zinc chloride, as the active carbon, the ortho-phenyl phenol was efficiently removed with higher removal rate.

Example 4

(43) (1) Zinc chloride-activated powdery active carbon (Seisei Shirasagi, manufactured by Japan EnviroChemicals, Ltd.) as an adsorbent was added to 5 g of grapefruit cold press oil in which ortho-phenyl phenol remained therein (ortho-phenyl phenol concentration=49.1 ppm) in an amount of 1% by mass, 2% by mass, 4% by mass or 8% by mass, based on the mass of the grapefruit cold press oil, followed by well suspending and stirring at the respective temperatures for 1 hour as shown in Table 2. Then, the adsorbent was filtered to recover the grapefruit cold press oil.

(44) (2) The content of ortho-phenyl phenol in the grapefruit cold press oil after the treatment with the zinc chloride-activated powdery active carbon, recovered in (1) above was analyzed with GC/MS-MS by the method described above, and the removal rate (%) of the ortho-phenyl phenol was obtained according to the mathematical formula (1) above. The results obtained are shown in Table 2.

(45) TABLE-US-00002 TABLE 2 Removal rate (%) of Ortho-Phenyl Phenol Treatment temperature ( C.) Amount of active 50 25 5 2 25 40 60 carbon.sup.1) added C. C. C. C. C..sup.2) C. C. 1% by mass 20 23 23 18 14 9 8 2% by mass .sup.3) 40 37 37 33 23 .sup.3) 4% by mass .sup.3) 63 48 58 47 40 .sup.3) 8% by mass .sup.3) 86 77 80 69 61 .sup.3) .sup.1)Zinc chloride-activated powdery active carbon (Seisei Shirasagi, manufactured by Japan EnviroChemicals Ltd. .sup.2)Room temperature .sup.3)Not conducted

(46) (3) As shown in Table 2, in removing the contaminant (residual agricultural chemicals and the like) contained in the essential oil (grapefruit cold press oil) by treating with active carbon, the contaminant (residual agricultural chemicals) can be effectively removed at a temperature in a range of from 25 C. to 40 C. Above all, it was found that when the treatment is conducted at a temperature of room temperature or lower, particularly from 25 C. to 5 C., the removal rate of ortho-phenyl phenol (agricultural chemical) is improved, and particularly, the removal rate in a temperature range of from 25 C. to 2 C. is high.

Test Example 1

(47) (1) Ingredients of the grapefruit cold press oil in which ortho-phenyl phenol remained therein (oil before subjecting to the treatment with active carbon) used in Example 4 were analyzed (analysis of flavor ingredients) with GC/MS-MS by the method described above, and additionally, in Example 4 (1), components of:

(48) (A) purified grapefruit cold press oil obtained by the treatment of adding zinc chloride-activated powdery active carbon (Seisei Shirasagi) in an amount of 8% by mass, followed by stirring at room temperature (25 C.) for 1 hour (hereinafter referred to as purified grapefruit oil (A)), and

(49) (B) purified grapefruit cold press oil obtained by the treatment of adding zinc chloride-activated powdery active carbon (Seisei Shirasagi) in an amount of 8% by mass, followed by stirring at a temperature of 25 C. for 1 hour (hereinafter referred to as purified grapefruit oil (B)),

(50) were analyzed (analysis of flavor ingredients) with GC/MS-MS by the method described above, and the residual ratio of each main flavor ingredient contained in the purified grapefruit oils (A) and (B) was obtained. The results obtained are shown in Table 3.

(51) The residual ratio of each ingredient (each flavor ingredient or ortho-phenyl phenol) in Table 3 was obtained by the following mathematical formula (2).
Residual ratio of each ingredient (%)=(C.sub.1/C.sub.0)100(2)
wherein C.sub.0 is the content (ppm) of each ingredient in the essential oil (grapefruit oil) before subjecting to purification treatment, and C.sub.1 is the content (ppm) of each ingredient in the essential oil (purified grapefruit oil) after conducting purification treatment.

(52) (2) (i) 30 g of the same grapefruit cold press oil in which ortho-phenyl phenol remained therein (oil before subjecting to purification treatment) as used in Example 4 was passed through a column (inner diameter of column: 15 mm, length of silica gel filled portion: 120 mm) filled with 15 g of silica gel (crushed silica gel Silica Gel 3A, manufactured by Fiji Silysia Chemical Ltd.) at 25 C., thereby obtaining purified grapefruit oil having the residual ratio of ortho-phenyl phenol of 23% (removal rate of ortho-phenyl phenol: 77%) (hereinafter referred to as purified grapefruit oil (C)) as shown in Table 3 below.

(53) (ii) The purified grapefruit oil (C) obtained in (i) above was analyzed (analysis of flavor ingredients) with GC/MS-MS by the method described above, and the residual ratio of each main flavor ingredient contained in the purified grapefruit oil (C) was obtained by the mathematical formula (2) above. The results obtained are shown in Table 3.

(54) TABLE-US-00003 TABLE 3 Residual Ratio of Flavor Component and Ortho-Phenyl Phenol Kind of Citrus Oil Non-purified Purified Purified Purified grapefruit grapefruit grapefruit grapefruit oil.sup.1) oil.sup.2) oil.sup.3) oil.sup.4) Flavor ingredient Nootkatone 100% 100% 82% 7% Octanal 100% 100% 100% 79% Nonanal 100% 100% 100% 69% Decanal 100% 100% 100% 77% Dodecanal 100% 100% 100% 100% Linalool 100% 100% 93.5% 100% Agricultural chemical: 100% 31% 14% 23% Ortho-phenyl phenol (Removal (Removal (Removal rate: 69%) rate: 86%) rate: 77%) .sup.1)Grapefruit cold press oil before subjecting to the treatment with active carbon .sup.2)Purified grapefruit cold press oil obtained by adding zinc chloride-activated active carbon powder in an amount of 8% by mass, and stirring at room temperature (25 C.) for 1 hour .sup.3)Purified grapefruit cold press oil obtained by adding zinc chloride-activated active carbon powder in an amount of 8% by mass, and stirring at 25 C. for 1 hour .sup.4)Purified grapefruit cold press oil obtained by passing through a silica gel column at 25 C.

(55) (3) As shown in Table 3, in the purified citrus oils (purified grapefruit oil (A) and purified grapefruit oil (B)) obtained by treating citrus oil (grapefruit cold press oil) in which agricultural chemical (ortho-phenyl phenol) remained therein with active carbon, the agricultural chemical (ortho-phenyl phenol) is smoothly removed with high removal rate. Additionally, decrease in flavor ingredients contained in the citrus oil (purified grapefruit oils (A) and (B)) is extremely small (residual ratio of flavor ingredients is extremely high), and poor balance of flavor and decrease in flavor strength did not almost occur.

(56) Contrary to this, in the purified citrus oil (purified grapefruit oil (C)) obtained by treating the citrus oil (grapefruit cold press oil) in which agricultural chemical (ortho-phenyl phenol) remained therein with silica gel, in the case of increasing the removal rate of the agricultural chemical (ortho-phenyl phenol) (in the case where the residual ratio of ortho-phenyl phenol was low as 23%), of the flavor ingredients contained in the citrus oil (purified grapefruit oil (C)), the residual ratio of nootkatone was extremely low, and almost all of nootkatone was lost. Additionally, octanal, nonanal and decanal were lost in considerable amounts, causing poor balance of flavor, and decrease of flavor strength.

(57) (4) Ten skilled panelists conducted functional evaluation on flavor strength and odor quality of grapefruit cold press oil before subjecting to the treatment with active carbon, and flavor strength and odor quality of the purified grapefruit oil (B) obtained by adding active carbon (Seisei Shirasagi) in an amount of 8% by mass and adsorption-treating at 25 C. for 1 hour under stirring. As a result, nine panelists of ten panelists judged that there is no great difference between the grapefruit oil before subjecting to the treatment with active carbon and the purified grapefruit oil (B) treated with active carbon.

(58) Furthermore, the same ten panelists conducted functional evaluation on flavor strength and odor quality of the purified grapefruit oil (C) obtained by purification-treating with silica gel. As a result, all the ten panelists judged that poor balance of flavor caused, flavor inherent in the grapefruit oil was lost, and flavor strength was greatly decreased.

Example 5

Preparation of Lemon Flavor Composition

(59) (1) 80 g of steam-activated powdery active carbon (Shirasagi A, manufactured by Japan EnviroChemicals, Ltd.) was added to 1 kg of lemon cold press oil, and suspended therein, followed by stirring at 25 C. for 30 minutes. 20 g of diatomaceous earth filter aid (Celite 545, manufactured by Showa Chemical Industry Co., Ltd.) was then added, and the solid contents were removed by pressure filtration, thereby obtaining 900 g of purified lemon cold press oil.

(60) (2) 100 g of a 60% ethanol aqueous solution was mixed with 100 g of the purified lemon oil obtained in (1) above, followed by liquid separation, and an ethanol layer was recovered. The ethanol layer recovered was used as a lemon flavor composition.

Example 6

Recovery of Limonene and Preparation of Orange Flavor Composition

(61) (1) 50 g of steam-activated powdery active carbon (Shirasagi A, manufactured by Japan EnviroChemicals, Ltd.) was added to 1 kg of orange cold press oil, and suspended therein, followed by stirring at 5 C. for 1 hour. 30 g of diatomaceous earth filter aid (Celite 545, manufactured by Showa Chemical Industry Co., Ltd.) was then added, and the solid contents were removed by pressure filtration, thereby obtaining 900 g of purified orange oil.

(62) (2) 100 g of the purified orange oil obtained in (1) above was distilled under reduced pressure, thereby recovering 50 g of limonene.

(63) (3) Distillation reside after recovering the limonene in (2) above was extracted with 80 g of a 60% ethanol aqueous solution, followed by liquid separation, and an ethanol layer was recovered. The ethanol layer recovered was used as an orange flavor composition.

Example 7

Preparation of Grapefruit Flavor Composition

(64) (1) 300 g of ethanol and 40 g of zinc chloride-activated powdery active carbon (Seisei Shirasagi, manufactured by Japan EnviroChemicals, Ltd.) were added to 500 g of grapefruit oil, and the resulting mixture was stirred at 10 C. for 1 hour. 40 g of diatomaceous earth filter aid (Celite 545, manufactured by Showa Chemical Industry Co., Ltd.) was then added, and the solid contents were removed by pressure filtration, thereby obtaining purified grapefruit oil.

(65) (2) 200 g of ion-exchanged water was added to the purified grapefruit oil obtained in (1) above, and then allowed to stand. Ethanol layer was recovered, and the ethanol layer recovered was used as a grapefruit flavor composition.

Example 8

Preparation of Fruit Juice Drink

(66) Using the orange flavor composition prepared in Example 6, fruit juice drink was prepared by using the ingredients shown in Table 4 below in amounts of the formulation shown in Table 4, uniformly mixing at 25 C., and then cooling to 5 C. The drink obtained had good orange flavor.

(67) TABLE-US-00004 TABLE 4 Formulation (g) of Fruit Juice Drink High-fructose glucose syrup 107.0 Citric acid 1.0 Sodium citrate 0.3 Orange-concentrated juice 51.8 Water-soluble orange flavor 1.0 Orange flavor composition prepared in 0.15 Example 6 Water Remainder Total 1000.0

Example 9

Preparation of Sports Drink

(68) Using the lemon flavor composition prepared in Example 5, sports drink was prepared by using the ingredients shown in Table 5 below in amounts of the formulation shown in Table 5, uniformly mixing at 25 C., and then cooling to 5 C. The drink thus obtained had lemon flavored fresh aroma.

(69) TABLE-US-00005 TABLE 5 Formulation (g) of Sports Drink Sugar 31.0 Glucose 15.7 Citric acid 1.0 Calcium Lactate 0.679 Sodium citrate 0.3 Sodium chloride 0.28 Potassium chloride 0.22 Vitamin C 0.864 Sodium L-glutamate 0.03 Niacin 0.013 Calcium pantothenate 0.007 Vitamin B6 0.022 Vitamin B12 0.00006 Lemon flavor 1.0 Lemon Flavor composition prepared in Example 5 0.1 Purified water Remainder Total 1000.0

Example 10

Preparation of Carbonated Drink

(70) Using the lemon flavor composition prepared in Example 5, carbonated drink was prepared by using the ingredients shown in Table 6 below in amounts of the formulation shown in Table 6, uniformly mixing at 15 C. under pressure, and then cooling to 5 C. The carbonated drink thus obtained had good taste and aroma since carboxylic acid was matched up with lemon flavor.

(71) TABLE-US-00006 TABLE 6 Formulation (g) of Carbonated Drink High-fructose glucose syrup 127.0 Citric acid 1.24 Purified water 200.0 Lemon flavor 1.0 Lemon flavor composition prepared in 0.1 Example 5 Carbonated water Remainder Total 1000.0

Example 11

Preparation of Health Drink

(72) Using the grapefruit flavor composition prepared in Example 7, health drink was prepared by using the ingredients shown in Table 7 below in amounts of the formulation shown in Table 7, uniformly mixing at 25 C., and then cooling to 5 C. The health drink thus obtained had good grapefruit flavor.

(73) TABLE-US-00007 TABLE 7 Formulation (g) of Health Drink White sugar 20.0 Sorbit 3.0 Citric acid 0.25 DL-malic acid 0.05 Aminoethylsulfonic acid 0.50 Glucuronolactone 0.50 Thiamine chloride 0.002 Riboflavin 0.005 Pyridoxine chloride 0.005 Caffeine 0.05 Nicotinic-acid amide 0.02 Purified honey 2.0 Grapefruit flavor 1.0 Grapefruit flavor composition prepared in 0.1 Example 7 Purified water Remainder Total 1000.0

Example 12

Preparation of Dentifrice

(74) Using the lemon flavor composition prepared in Example 5, dentifrice was prepared by using the ingredients shown in Table 8 below in amounts of the formulation shown in Table 8, uniformly mixing at 25 C., and then cooling to room temperature. The dentifrice thus obtained had lemon flavor.

(75) TABLE-US-00008 TABLE 8 Formulation (g) of Dentifrice Dicalcium phosphate 10.0 Sodium lauryl sulfate 2.0 Sodium carboxymethyl cellulose 0.5 Saccharine sodium 0.02 Mint flavoring agent 1.0 Citrus mint flavor 5.0 Flavor composition described in Example 4 0.5 Glycerin Remainder Total 100

Example 13

Preparation of Dental Rinse

(76) Using the orange flavor composition prepared in Example 6, dental rinse was prepared by using the ingredients shown in Table 9 below in amounts of the formulation shown in Table 9, uniformly mixing at 25 C., and then cooling to 5 C. The dental rinse thus obtained had orange flavor.

(77) TABLE-US-00009 TABLE 9 Formulation (part by mass) of Dental Rinse Ethyl alcohol 10.0 Polyoxyethylene hydrogenated castor oil 2.0 Mint flavoring agent 0.5 Saccharine sodium 0.02 Citrus flavor 0.25 Orange flavor composition prepared in 0.1 Example 6 Glycerin 10.0 Purified water Remainder Total 100.0

Example 14

Production of Candy

(78) Using the grapefruit flavor composition prepared in Example 7, candy was manufactured by using the ingredients shown in Table 10 below in amounts of the formulation shown in Table 10, melt kneading at 100 C., extruding into a rod shape having a diameter of about 1.5 cm, solidifying by cooling, and then cutting to a given length (about 2 cm). The candy thus obtained had grapefruit flavor, had good aroma and good taste.

(79) TABLE-US-00010 TABLE 10 Formulation (part by mass) of Candy Sugar powder 50 Starch syrup 33 Citric acid 1 Grapefruit flavor 0.25 Grapefruit flavor composition prepared in 0.01 Example 7 Purified water Remainder Total 100

Example 15

Preparation of Flavor Emulsion (Cloudy)

(80) (1) 5.0 g of sucrose acetate isobutylate (SAIB, manufactured by Eastman Kodak Company), 1.67 g of the orange flavor composition prepared in Example 6, 3.33 g of middle-chain triglyceride (MCT OIL) (PANACET 810, manufactured by Ougi Chemical Co., Ltd.) and 0.2 g of an elemi resin were placed in a 200 ml beaker, and dissolved by heating, thereby obtaining a mixture comprising the orange flavor composition.

(81) (2) 250 g gum arabic and 648 g of water were placed in a 1 liter beaker, and dissolved by heating, followed by sterilization. Thus, a gum arabic aqueous solution was prepared.

(82) (3) The mixture prepared in (1) above was added to the gum arabic aqueous solution prepared in (2) above, followed by stirring at 5,000 to 12,000 rpm for 30 minutes. The resulting mixture was further treated with a high pressure homogenizer under the condition of 100 to 300 kg/cm.sup.2, thereby preparing a flavor emulsion (cloudy).

Example 16

Preparation of Fruit Juice Drink Using Flavor Emulsion (Cloudy)

(83) Using the flavor emulsion (cloudy) prepared in Example 15, fruit juice drink was prepared by using the ingredients shown in Table 11 below in amounts of the formulation shown in Table 11, uniformly mixing at 25 C., and then cooling to 5 C. The drink thus obtained had orange flavor, and maintained high appearance of preference property.

(84) TABLE-US-00011 TABLE 11 Formulation (g) of Fruit Juice Drink Using Flavor Emulsion (Cloudy) High-fructose glucose syrup 107.0 Citric acid 1.0 Sodium citrate 0.3 Orange concentrated juice 51.8 Water-soluble orange flavor 1.0 Flavor emulsion (cloudy) prepared in 0.52 Example 15 Water Remainder Total 1000.0

Example 17

Preparation of Citrus Flavor Composition

(85) Citrus flavor composition was prepared by using the ingredients shown in Table 12 in the formulation shown in Table 12, and uniformly mixing at 25 C.

(86) TABLE-US-00012 TABLE 12 Formulation (g) of Citrus Flavor Composition Decanol 0.25 Dodecanol 0.25 Decanal 1.40 Dodecanal 0.75 Citral 1.85 Geranyl acetate 2.00 Terpenyl acetate 2.00 Linalyl acetate 2.50 Citronellol 2.00 Orange flavor composition prepared in Example 6 1000.00

INDUSTRIAL APPLICABILITY

(87) Agricultural chemicals and other contaminants, contained in an essential oil can be removed simply with high removal rate by the present invention, without causing poor balance of flavor and decrease in flavor strength, of the essential oil. Therefore, the present invention is extremely useful as a process for producing a purified essential oil having excellent safety and high quality.

(88) Although the present invention has been described in detail and by reference to the specific embodiments, it is apparent to one skilled in the art that various modifications or changes can be made without departing the spirit and scope of the present invention. The present application is based on Japanese Patent Application No. 2008-288699 filed Nov. 11, 2008, the disclosure of which is incorporated herein by reference in its entity.