CN86102952A - Remove the method for assorted peculiar smell hot puckery in the volatile oil - Google Patents

Remove the method for assorted peculiar smell hot puckery in the volatile oil Download PDF

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Publication number
CN86102952A
CN86102952A CN86102952.6A CN86102952A CN86102952A CN 86102952 A CN86102952 A CN 86102952A CN 86102952 A CN86102952 A CN 86102952A CN 86102952 A CN86102952 A CN 86102952A
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CN
China
Prior art keywords
oil
superoxide
volatile oil
acid
peculiar smell
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Pending
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CN86102952.6A
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Chinese (zh)
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CN1006553B (en
Inventor
马蒙·M·侯赛因
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Nabisco Brands Inc
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Nabisco Brands Inc
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Publication date
Application filed by Nabisco Brands Inc filed Critical Nabisco Brands Inc
Publication of CN86102952A publication Critical patent/CN86102952A/en
Publication of CN1006553B publication Critical patent/CN1006553B/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, 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
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C11B9/022—Refining

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  • 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)
  • Fats And Perfumes (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Preparation Of Fruits And Vegetables (AREA)

Abstract

By the volatile oil that vegetable matter extracts, handle to remove the hot puckery assorted peculiar smell that it gives out with peroxide-acid reagent.

Description

Remove the method for assorted peculiar smell hot puckery in the volatile oil
The present invention relates to superoxide one sour agent treated by the volatile oil that extracts in the vegetable matter to remove the method for hot puckery smell wherein.
The new system volatile oil that has just distilled from vegetable matter has a kind of hot puckery smell of called optical imaging usually.These hot puckery smells also are called underdone, burn and steam peculiar smell.For the spearmint oil or the Spearmint Oil 56 that extract with distillation method with former vegetable matter, this kind interest is especially serious.The conventional process of removing the hot puckery smell that the new system fry dried food ingredients goes out is to allow these oil be about 6 to 24 months oxygen being arranged and be not subjected to carry out old slaking in the full packaging container of actinic radiation.This old maturing process loses incentive economically naturally, because this needs the storage facilities of careful management and control, and a long process time and be subjected to the professional's of good technique training supervision.Requirement in all these storage work all can cause very heavy economical load.
Find that by the present invention the new volatile oil that extracts contains hot puckery peculiar smell from vegetable matter, when handling with superoxide one sour reagent, can remove the hot puckery assorted peculiar smell in the oil.
By of the present invention, the superoxide one sour reagent that is used for handling volatile oil is the mixture of one or more water-soluble inorganic peroxide such as hydrogen peroxide and/or ozone and one or more water-soluble inorganics acid example hydrochloric acid, sulfuric acid and phosphoric acid.Superoxide is a promoting agent in reagent system of the present invention.Acids wherein just is used for the acidifying superoxide.
Superoxide is used with the water-soluble solution form with acid, and wherein the concentration of superoxide or acid is about 30 to 40 weight percents.Superoxide and/or acid with higher or low concentration also can be used.
As following announcement, superoxide in the reagent and acid are to join pending oil together
By of the present invention, the volatile oil that needs to handle with superoxide one acid-respons agent is those volatile oil that newly extract from vegetable matter.These oil can be used as spices in food, lamb are ordered candy, perfume or makeup industry.They comprise the oils of being extracted by the following plants raw material, star anise, sweet basil, dill grass, camomile, eucalyptus, fennel, Flos Pelargonii, hops, Bay leaf, lemongrass, nine rare look wood, coriander, amber, camphor, Asiatic sweet leaf, galbanum, Davana, peppermint section (spearmint and peppermint).
The volatile oil of handling with superoxide one acid-respons agent by need of the present invention can be extracted by its former vegetable matter (be leaf, fruit, bark, root, grass, wood, heartwood, glue, cream liquid, berry, seed, spend assorted, sprig and bud), and its extracting method is that common technology is a distillation method.
United States Patent (USP) 4,478,864 disclose with maleic anhydride and have handled the new system spearmint oil, reach the purpose that prevents that in ageing process certain assorted different smell from forming.This method is with the form of menthofuran maleic anhydride complex compound most of menthofuran in the new system spearmint oil to be removed.Therefore in the ageing process, have only the existence of muttering of the peppermint piperazine of minute quantity, it carries out oxygenizement and produces undesirable smell.Yet this method can not solve the assorted peculiar smell problem of inherent in the new system spearmint oil fully.With United States Patent (USP) 4,478, the volatile oil that the method described in 864 was handled, still must carry out ageing process so that remove and remain the assorted peculiar smell that is in the new system volatile oil.
Therefore, before present inventor work, unprecedented usefulness extremely is easy to method and handles new system volatile oil removing its hot puckery assorted peculiar smell, and used reagent can be stored to change places and separated from oil very much.
The present invention relates to handle with acidifying superoxide and/or ozone, from the volatile oil that vegetable matter extracts, the hot puckery assorted peculiar smell that it distributed is removed.The present invention also relates to the method for the hot puckery assorted peculiar smell that removing distributes from the volatile oil that vegetable matter extracts, this method comprises with acidifying superoxide and/or ozone handles described oil.
The new oil that extracts can carry out rectifying (redistillation) earlier to promote the discrete characteristic properties before or after handling with superoxide one acid-respons agent.For example, peppermint is carried out the dimethyl thioether that rectifying then can be removed its underdone weedy character of sending.
To handle the hot puckery assorted peculiar smell of removing with superoxide one acid-respons agent in the new system volatile oil, can determine its feature to sense influence from it, these hot puckery assorted peculiar smell can by the sense influence determine to it is characterized by smelly mouse hot puckery, underdone, that give birth to, weeds by mouse with empyreumatic.
Believe the chemical ingredients that plays hot puckery assorted peculiar smell in the new system volatile oil, still fail so far to determine with analytical procedure.In oil, they are to occur with micro-concentrations at the most.No matter be that volatile oil is carried out before or after the handling procedure of the present invention, the chemical ingredients of when analyzing this oil with gas-chromatography, can not observing the volatility part in (analytical) oil has any variation.
So-called herein volatility partly is meant those abundant volatile parts in the oil so that observe and analyze with the gas chromatograph that a Carbowax-20 post (maximum operating temperature is 230 ℃) and an injector (maximum operating temperature is 250 ℃) are housed.
When handling volatile oil, can adopt liquid phase/liquid-phase extraction method to extract volatile oil, or this oil can contact with the immobilized superoxide one sour reagent on the solid carrier with superoxide one sour reagent of the present invention.
When handling volatile oil, as used water-soluble solution is 30% to 40%(by weight) superoxide and during acid, the superoxide in the used reagent and the amount of acid constituents, by volume, respectively being 0.005% to 2% of handled oil approximately, serves as better with 0.01% to 0.03%.
In the present invention, adding superoxide is for volatile oil is handled with sour purpose.Both add simultaneously, and acid wherein is to be used to form the acidifying superoxide.
When coming handling oil, can carry out being about under 20 ℃ to 25 ℃ the room temperature, and temperature extracts faster and better effects if when higher with superoxide one sour reagent.Can be for realizing that the mixture that shakes volatile oil and superoxide one sour reagent in the equipment that shakes commonly used that effective liquid phase/liquid-phase extraction system designs carries out the liquid phase extraction.According to the amount of the amount of superoxide one sour reagent, the volatile oil sample that is extracted, initially be present in the content of assorted peculiar smell hot puckery in this sample and the difference of shaking the situation of equipment, required time of extraction process is different, may only need 1 to 10 minute.
Only need to carry out primary treatment and can enough finish the work of removing hot puckery assorted peculiar smell with superoxide one sour reagent.With such treatment process, all hot puckery assorted peculiar smell can eliminate fully.
In liquid phase/liquid-phase extraction method, once be used to handle the superoxide one sour reagent of volatile oil, no matter use in advance or without whizzer, all available oil/water separation equipment such as separating funnel one class is separated superoxide one sour reagent from mixture.The superoxide one sour reagent of remaining trace also can further be removed from oil, and its treatment process is to use Na 2CO 3After (playing antacid effect) solution-treated, wash with distilled water again, carry out drying with supercentrifuge then.
At United States Patent (USP) 4,478, the Substrate that in 864 the narration, wherein causes (in oily ageing process) to produce assorted peculiar smell is to have disposed from new system oil really with menthofuran one maleic anhydride complex compound.In contrast, by of the present invention, the different chemicals that cause assorted flavor are handled with superoxide one sour reagent in new system oil, it are not disposed after this processing.Superoxide one sour reagent may be oxidation by this way those cause producing the Substrate of assorted peculiar smell, promptly from the angle of assorted peculiar smell, it is harmless that foot becomes those Substrates.Thereby, now again new system oil has been carried out ageing with regard to not needing for to obtain the effect the same with common method.
Can press United States Patent (USP) 4,478,864 described methods are handled before or after the new system volatile oil, handle this freshly prepd volatile oil with superoxide one sour reagent.
The volatile oil of handling by the present invention can be added in the various products as food flavouring or spices, these products draw together food, lamb order candy such as chewing gum and peppermint (compressing tablet) sugar, perfume, makeup, reach products such as watch box health product or medicine.
Following example scope of the present invention for illustrative purposes only but do not limit the scope of the invention.
Example 1
In 250 milliliters separatory funnel, 100 milliliters new distillatory spearmint oil sample, with respectively be 0.02 gram be 30% H by weight 2O 2Shook 1 to 2 minute with 12NHCl.After being separated into two liquid layers, the aqueous layer that is positioned at the bottom is discharged.The peppermint oil reservoir is respectively extracted and clean twice with 50 milliliters 5% sodium carbonate solutions and 50 ml distilled waters, then the separated aqueous solution is fully drained.In being 2000 rev/mins to 3000 rev/mins whizzer, rotating speed carries out drying with anhydrous sodium sulphate then.
The oil that is obtained is the top quality ageing spearmint oil of the clean ripe fragrance characteristic of no crystalline.Just the puckery fragrance of the sort of suffering is disposed fully in the oil plant.The taste of treated oil is assessed with the soft sweets of the handling oil that is added with 0.2% weight and with the chewing gum of the handling oil of 0.05% to 1.5% weight, and the taste of these two kinds of food is equally all good than the food that is added with untreated oil.
Example 2
Freshly prepd spearmint oil samples is handled with the method steps of example 1, and observing treated oil has same improvement.
The improved qualitatively degree of handling oil, depend on the quality of oil plant just: first oil plant quality is poor more, and taste is hot more puckery, and it is also just good more then to handle the obtained improvement in back through the method for the invention.

Claims (15)

1, the volatile oil that extracts from vegetable matter is characterized in superoxide and/or ozonize with acidifying, thereby removes the hot puckery assorted peculiar smell that gives out.
By the desired volatile oil of claim 1, it is characterized in that 2, acidifying superoxide wherein and/or ozone are the inorganic peroxides in the presence of at least a water-soluble inorganic acid.
3, by claim 1 or 2 desired volatile oil, it is characterized in that wherein used superoxide is a hydrogen peroxide.
4, by any one desired volatile oil in the claim 1 to 3, it is characterized in that wherein used acid is hydrochloric acid, sulfuric acid or phosphoric acid.
5, by any one desired volatile oil in the claim 2 to 4, it is characterized in that wherein used superoxide is a hydrogen peroxide, used acid then is hydrochloric acid.
By any one desired volatile oil in the claim 1 to 5, it is characterized in that 6, it is pennyroyal oil, spearmint oil, Spearmint Oil 56 or the oil that distills.
7, flavouring agent or the spice product made from any one the described volatile oil in the claim 1 to 6.
8, the lamb made from any one the described volatile oil in the claim 1 to 6 is ordered candy, food, makeup, perfume, watch box health product or medicine.
9, order candy by the described lamb of claim 8, it is characterized in that they are chewing gums, candy or peppermint compressing tablet sugar.
10, remove the method for the hot puckery assorted peculiar smell of vegetalitas volatile oil ox, it is characterized in that, this method comprises the step with acidifying superoxide and/or the said volatile oil of ozonize.
11, by the desired method of claim 10, it is characterized in that wherein used acidifying superoxide and/or ozone are the inorganic peroxides in the presence of at least a water soluble acid.
12, by claim 10 or 11 desired methods, it is characterized in that wherein used superoxide is a hydrogen peroxide.
13, by any one desired method in the claim 10 to 12, it is characterized in that wherein used acid is hydrochloric acid, sulfuric acid or phosphoric acid.
14, by any one desired method in the claim 10 to 13, it is characterized in that wherein used acidifying superoxide is a hydrogen peroxide, used acid then is hydrochloric acid.
By any one desired method in the claim 10 to 14, it is characterized in that 15, described oil is pennyroyal oil, spearmint oil, Spearmint Oil 56 or the oil that distills.
CN86102952A 1985-04-26 1986-04-26 Remove the method for assorted peculiar smell hot puckery in the volatile oil Expired CN1006553B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US72764685A 1985-04-26 1985-04-26
US727,646 1985-04-26

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CN86102952A true CN86102952A (en) 1987-11-04
CN1006553B CN1006553B (en) 1990-01-24

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EP (1) EP0199354B1 (en)
JP (1) JPS61258899A (en)
CN (1) CN1006553B (en)
AU (1) AU583915B2 (en)
CA (1) CA1285175C (en)
DE (1) DE3664478D1 (en)
ES (1) ES8802367A1 (en)
NZ (1) NZ215941A (en)
ZA (1) ZA863080B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107653064A (en) * 2017-09-27 2018-02-02 湖北中烟工业有限责任公司 A kind of inoxidizability is strong, the preparation method and applications of high fragrance Rome yellow chamomile fermentation absolute oil
CN107699352A (en) * 2017-09-27 2018-02-16 湖北中烟工业有限责任公司 A kind of method and its application for improving Roman chamomille oil flavouring essence quality
WO2020135896A1 (en) * 2018-12-29 2020-07-02 珠海市自然之旅生物技术有限公司 Antimicrobial essential oil smell removal method

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4613513A (en) * 1985-03-20 1986-09-23 Nabisco Brands, Inc. Essential oils treatment to remove harsh notes therefrom
US8865192B2 (en) * 2006-07-07 2014-10-21 The Procter & Gamble Co Flavor oils with reduced sulfur content and use in oral care compositions
CN113403147A (en) * 2021-07-21 2021-09-17 广州丽悦香精香料有限公司 Snow rhododendron essential oil and extraction method and application thereof
CN114854495B (en) * 2022-06-16 2023-11-03 银谷芳香科技有限公司 Technological method for extracting Damascus rose essential oil through sectional distillation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE334274C (en) * 1917-10-18 1921-03-10 Hugo Bruen Process for improving the taste and smell of vegetables and fodder plants from the crucifer family and from related families
DE334374C (en) * 1918-06-18 1921-03-12 Rudolf Schmidtmann Aircraft bomb sights
FR1131573A (en) * 1954-07-16 1957-02-25 Dragoco Gerberding Co Gmbh Process for preparing oxygenated products with a musky odor and products conforming to those obtained
IT1056707B (en) * 1966-09-29 1982-02-20 Corvi E Dott Fardeco Spa PROCEDURE FOR THE PREPARATION OF AN ESPENTIAL OIL OF TURPINE
US4440790A (en) * 1982-12-20 1984-04-03 Warner-Lambert Company Process for stabilizing peppermint oil

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107653064A (en) * 2017-09-27 2018-02-02 湖北中烟工业有限责任公司 A kind of inoxidizability is strong, the preparation method and applications of high fragrance Rome yellow chamomile fermentation absolute oil
CN107699352A (en) * 2017-09-27 2018-02-16 湖北中烟工业有限责任公司 A kind of method and its application for improving Roman chamomille oil flavouring essence quality
WO2020135896A1 (en) * 2018-12-29 2020-07-02 珠海市自然之旅生物技术有限公司 Antimicrobial essential oil smell removal method

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Publication number Publication date
EP0199354A2 (en) 1986-10-29
JPS61258899A (en) 1986-11-17
ES8802367A1 (en) 1988-06-01
AU583915B2 (en) 1989-05-11
CA1285175C (en) 1991-06-25
DE3664478D1 (en) 1989-08-24
ES554260A0 (en) 1988-06-01
NZ215941A (en) 1988-08-30
CN1006553B (en) 1990-01-24
EP0199354A3 (en) 1987-05-06
EP0199354B1 (en) 1989-07-19
AU5681186A (en) 1986-10-30
ZA863080B (en) 1986-12-30

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