EP0199354B1 - Essentielle Öle, die behandelt sind zum Ausscheiden von harten Noten daraus - Google Patents

Essentielle Öle, die behandelt sind zum Ausscheiden von harten Noten daraus Download PDF

Info

Publication number
EP0199354B1
EP0199354B1 EP86105661A EP86105661A EP0199354B1 EP 0199354 B1 EP0199354 B1 EP 0199354B1 EP 86105661 A EP86105661 A EP 86105661A EP 86105661 A EP86105661 A EP 86105661A EP 0199354 B1 EP0199354 B1 EP 0199354B1
Authority
EP
European Patent Office
Prior art keywords
oil
peroxide
acid
notes
essential oils
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP86105661A
Other languages
English (en)
French (fr)
Other versions
EP0199354A3 (en
EP0199354A2 (de
Inventor
Mamoun M. Hussein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nabisco Brands Inc
Original Assignee
Nabisco Brands Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nabisco Brands Inc filed Critical Nabisco Brands Inc
Publication of EP0199354A2 publication Critical patent/EP0199354A2/de
Publication of EP0199354A3 publication Critical patent/EP0199354A3/en
Application granted granted Critical
Publication of EP0199354B1 publication Critical patent/EP0199354B1/de
Expired legal-status Critical Current

Links

Classifications

    • 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

Definitions

  • the peroxide-acid reagent which is used to treat the essential oils in accordance with the present invention is a combination of one or more water soluble inorganic peroxides such as hydrogen peroxide and/or ozone and one or more water soluble inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid.
  • the peroxide is the active agent in the reagent system of the present invention.
  • the acid is merely used to acidify the peroxide.
  • the peroxides and the acids are preferably employed as aqueous solutions having a peroxide or acid concentration of about 30 to 40 weight percent.
  • Aqueous solutions of the peroxides and/ or acids having higher or lower concentrations may also be used.
  • the essential oils which are to be treated with the peroxide-acid reagent in accordance with the present invention are the freshly extracted essential oils of botanical matter. These oils are used as flavorants in the food, confectionary, perfume and cosmetic industries. These oils would include those obtained from the following botanical materials: anise, basil, dill weed, chamomile, eucalyptus, fennel, geranium, hop, laurel leaf, lemongrass, bois de rose, caraway, amber, camphor, amyris, galbanum, davana, mentha (spearmint and peppermint).
  • the harsh flavor off-notes in the fresh essential oils, which are to be removed by treatment with the peroxide-acid reagent may be characterized, as such, organoleptically. Organoleptically these harsh off-flavor notes may be characterized as: harsh, green, raw, weedy, skunky and burnt.
  • volatile components those components of the oil which are volatile enough as to be capable of being detected by gas chromatography analysis using a Carbowax@-20M column operated at a maximum temperature of 230°C and with an injector temperature of a maximum of 250°C.
  • the oil may be extracted in a liquid/liquid extraction with the peroxide-acid reagent, or it may be contacted with the peroxide-acid reagent immobilized on a solid support.
  • the treatment with the peroxide-acid reagent may be conducted at room temperature, of about 20-25°C, although at higher temperatures a more rapid/efficient extraction may be effected.
  • the liquid/liquid extraction may be done by vigorously shaking a mixture of the oil and the peroxide-acid reagent in commonly employed shaking devices designed to effect efficient liquid/liquid extraction systems.
  • the extraction time required may be about one to ten minutes.
  • aqueous peroxide-acid reagent is used to treat the essential oil in the liquid/liquid extraction process, it is readily moved therefrom by the use of oil/water separating devices such as a separatory funnel, with or without prior centrifuging. Residual traces of the peroxide-acid reagent can be further readily extracted from the oil by treatment with a solution of Na 2 CO 3 (to neutralize the acid) followed by washing with distilled water. The oil is then dried by high speed centrifugation.
  • a 100 ml sample of freshly distilled peppermint oil is shaken, in a 250 ml separatory funnel, with 0.02 grams each of 30% by weight aqueous H 2 0 2 and 12 N HCI for 1 to 2 minutes.
  • the aqueous (bottom) layer is discarded after complete separation of the layers.
  • the peppermint oil layer is washed by extraction with 2x50 ml 5% sodium carbonate solution and 2x50 ml distilled water, and the completely separated aqueous layer is then discarded.
  • the oil is dried with 4 g anhydrous sodium sulfate and by centrifucation at 2000 to 3000 rpm.
  • a sample of freshly distilled spearmint oil is also treated according to the procedure of Example 1. A similar improvement of the treated oil is noted.

Claims (8)

1. Verfahren zum Entfernen von strengen unangehmen Geschmacksnoten aus dem essentiellen 01 eines botanischen Materials durch Oxidation, dadurch gekennzeichnet, daß man das Öl mit einem angesäuerten Peroxid und/oder Ozon behandelt.
2. Verfahren gemäß Anspruch 1, dadurch gekennzeichnet, daß das angesäuerte Peroxid und/oder Ozon in Gegenwart wenigstens einer wasserlöslichen Säure vorliegt, und daß das Peroxid ein anorganisches Peroxid ist.
3. Verfahren gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, daß das Peroxid Wasserstoffperoxid ist.
4. Verfahren gemäß einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß die Säure Salzsäure, Schwefelsäure oder Phosphorsäure ist.
5. Verfahren gemäß einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß das angesäuerte Peroxid Wasserstoffperoxid und die Säure Salzsäure ist.
6. Verfahren gemäß einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß das essentielle Öl ein Minzöl, ein Pfefferminzöl, ein Spermintöl oder ein destilliertes Öl ist.
7. Verwendung eines gemäß einem der Ansprüche 1 bis 6 behandelten essentiellen Öls für Süßwaren, Nahrungsmittel, Kosmetika, Parfums, Körperhygieneprodukte oder medizinische Produkte.
8. Verwendung gemäß Anspruch 7, bei welcher die Süßware Kaugummi, ein Bonbon oder eine gepreßte Minze ist.
EP86105661A 1985-04-26 1986-04-24 Essentielle Öle, die behandelt sind zum Ausscheiden von harten Noten daraus Expired EP0199354B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US72764685A 1985-04-26 1985-04-26
US727646 2000-11-30

Publications (3)

Publication Number Publication Date
EP0199354A2 EP0199354A2 (de) 1986-10-29
EP0199354A3 EP0199354A3 (en) 1987-05-06
EP0199354B1 true EP0199354B1 (de) 1989-07-19

Family

ID=24923444

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86105661A Expired EP0199354B1 (de) 1985-04-26 1986-04-24 Essentielle Öle, die behandelt sind zum Ausscheiden von harten Noten daraus

Country Status (9)

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

Families Citing this family (7)

* 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
CN107653064A (zh) * 2017-09-27 2018-02-02 湖北中烟工业有限责任公司 一种抗氧化性强、高香气罗马春黄菊发酵净油的制备方法及其应用
CN107699352A (zh) * 2017-09-27 2018-02-16 湖北中烟工业有限责任公司 一种提高罗马春黄菊油香气品质的方法及其应用
CN109601821A (zh) * 2018-12-29 2019-04-12 珠海市自然之旅生物技术有限公司 一种具有抗菌性能精油气味去除方法
CN113403147A (zh) * 2021-07-21 2021-09-17 广州丽悦香精香料有限公司 一种雪层杜鹃精油及其提取方法和应用
CN114854495B (zh) * 2022-06-16 2023-11-03 银谷芳香科技有限公司 一种分段式蒸馏提取大马士革玫瑰精油的工艺方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE334274C (de) * 1917-10-18 1921-03-10 Hugo Bruen Verfahren zur Verbesserung des Geschmackes und Geruches von Gemuese- und Futterpflanzen aus der Familie der Kruziferen sowie aus verwandten Familien

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE334374C (de) * 1918-06-18 1921-03-12 Rudolf Schmidtmann Bombenvisier fuer Luftfahrzeuge
FR1131573A (fr) * 1954-07-16 1957-02-25 Dragoco Gerberding Co Gmbh Procédé de préparation de produits oxygénés à odeur musquée et produits conformes à ceux obtenus
IT1056707B (it) * 1966-09-29 1982-02-20 Corvi E Dott Fardeco Spa Procedimento per la preparazione di un olio essenziale di trementina
US4440790A (en) * 1982-12-20 1984-04-03 Warner-Lambert Company Process for stabilizing peppermint oil

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE334274C (de) * 1917-10-18 1921-03-10 Hugo Bruen Verfahren zur Verbesserung des Geschmackes und Geruches von Gemuese- und Futterpflanzen aus der Familie der Kruziferen sowie aus verwandten Familien

Also Published As

Publication number Publication date
EP0199354A3 (en) 1987-05-06
DE3664478D1 (en) 1989-08-24
ES8802367A1 (es) 1988-06-01
CN1006553B (zh) 1990-01-24
ES554260A0 (es) 1988-06-01
NZ215941A (en) 1988-08-30
ZA863080B (en) 1986-12-30
AU5681186A (en) 1986-10-30
AU583915B2 (en) 1989-05-11
CN86102952A (zh) 1987-11-04
CA1285175C (en) 1991-06-25
JPS61258899A (ja) 1986-11-17
EP0199354A2 (de) 1986-10-29

Similar Documents

Publication Publication Date Title
EP0198262B1 (de) Essenzielle Öle, die behandelt sind zum Ausscheiden von harten Noten daraus
US4708880A (en) Essential oils treated to remove harsh notes therefrom
DE2808710B2 (de) 1- [3-(Methylthio)- butyryl] -2,6,6trimethylcyclohexen und das 13-Cyclohexadien-Analoge, Verfahren zu deren Herstellung und deren Verwendung
EP0199354B1 (de) Essentielle Öle, die behandelt sind zum Ausscheiden von harten Noten daraus
SU988175A3 (ru) Способ изменени , модифицировани и усилени аромата и /или вкуса пищевых продуктов
SU585799A3 (ru) Способ изменени органолептических свойств изделий
AU2007235073B2 (en) Methods for removing contaminants from essential oils
JPH02182789A (ja) 香味物質及び芳香物質の製造方法
DE2540624C3 (de) Würz- und Aromastoff und Verfahren zu dessen Herstellung
EP0363971B1 (de) Verfahren zur Entfernung von Terpenen aus etherischen Ölen
JP6052556B2 (ja) 従来溶剤の代替溶剤によって臭気抽出物を抽出する方法
US5296461A (en) Diterpenoid alcohols for flavouring purposes
JPH0155318B2 (de)
DE2840823A1 (de) Trans, trans- delta -damascon und dessen verwendung als wuerzstoff
JPS641146B2 (de)
DE2065324C3 (de) 2,6,6-Trimethyl-Miydroxy-lcrotonoyl-cyclohexen-Q), seine Verwendung als Riech- und Geschmacksstoff und Verfahren zu seiner Herstellung
JPH0816048B2 (ja) 口腔用組成物
JPS61223097A (ja) 精油
DE2634077A1 (de) Als riech- und geschmacksstoff verwendbares spiranderivat
DE60006822T2 (de) Herstellung eines gamma-ungesättigten beta-lactons und seine verwendung als aromatisierender und parfümisierender bestandteil
US3440183A (en) 2-ethylpyromeconic acid as an aroma enhancer for perfumes
JPH0450295B2 (de)
JPS596057A (ja) 消臭物質の製造方法
US133322A (en) Oscae loew and julius e
DE2418335C2 (de) Neue Cyclohexen-keto-Derivate und deren Verwendung zur Geruchs- und Aromamodifizierung

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): BE DE FR GB IT SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): BE DE FR GB IT SE

17P Request for examination filed

Effective date: 19870702

17Q First examination report despatched

Effective date: 19880114

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR GB IT SE

REF Corresponds to:

Ref document number: 3664478

Country of ref document: DE

Date of ref document: 19890824

ET Fr: translation filed
ITF It: translation for a ep patent filed

Owner name: MODIANO & ASSOCIATI S.R.L.

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19900424

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19900425

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19900430

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
BERE Be: lapsed

Owner name: NABISCO BRANDS INC.

Effective date: 19900430

GBPC Gb: european patent ceased through non-payment of renewal fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19901228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19910101

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

EUG Se: european patent has lapsed

Ref document number: 86105661.2

Effective date: 19910116

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050424