GB2297557A - Solubilised essential oils - Google Patents

Solubilised essential oils Download PDF

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Publication number
GB2297557A
GB2297557A GB9601767A GB9601767A GB2297557A GB 2297557 A GB2297557 A GB 2297557A GB 9601767 A GB9601767 A GB 9601767A GB 9601767 A GB9601767 A GB 9601767A GB 2297557 A GB2297557 A GB 2297557A
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United Kingdom
Prior art keywords
acid
coreactant
essential oil
fatty acid
polyol
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.)
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GB9601767A
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GB9601767D0 (en
Inventor
David William Cowie
Keith Coupland
David Andrew Parker
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Croda International PLC
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Croda International PLC
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Publication date
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Publication of GB9601767D0 publication Critical patent/GB9601767D0/en
Publication of GB2297557A publication Critical patent/GB2297557A/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/75—Fixation, conservation, or encapsulation of flavouring agents the flavouring agents being bound to a host by chemical, electrical or like forces, e.g. use of precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
    • 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
    • C11B9/0003—Compounds of unspecified constitution defined by the chemical reaction for their preparation
    • 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
    • C11B9/0007—Aliphatic compounds

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Fats And Perfumes (AREA)

Abstract

A method of treating an essential oil to render it water soluble or water dispersible, comprises reacting the oil with ethylene oxide. A polyol or partial fatty acid ester can be added as a coreactant in order to improve the water solubility or dispersibility.

Description

SOLUBILISED ESSENTIAL OILS The present invention relates to solubilised essential oils and to a method of making essential oils water soluble or water dispersible. In particular, it relates to a procedure for chemical modification of an essential oil to render it water soluble or water dispersible whilst effectively retaining the original odour and flavour characteristics of the unmodified oil.
Essential oils can be defined as the predominantly volatile materials isolated by some physical process from an odorous single species botanical. Over 3000 oils have been identified from the vast number of plant species and several hundred have been commercialised. Essential oils are isolated from various plant parts, such as leaves (patchouli), fruit (mandarin), bark (cinnamon), root (ginger), grass (citronella), wood (amyris) , heartwood (cedar), gum (myrrh), balsam (tolu balsam oil), berries (pimenta), seed (caraway), flowers (rose), twigs (clove stems), and buds (cloves).
The most important method of isolating essential oils from the botanical is steam or hydrodistillation employing either dry steam, wet steam, or water. The most common procedure iswet steam distillation. For essential oils that are sensitive to heat, eg jasmine or tuberose, or which contain an essentially nonvolatile constituent, eg piperine in black pepper, solvent extraction processes are employed. Yet other essential oils may be extracted using special pressing equipment.
Essential oils are composed of a wide variety of natural organic components and chemicals of many functional groups and molecular structures. The volatile components of essential oils usually contain fifteen carbon atoms or iess.
However, seed oils can contain long chain fatty acids or esters and even glycerides that are carried over in distillation. Essential oils are basically made up of carbon, hydrogen and oxygen and occasionally nitrogen and sulphur. The largest class of components present in essential oils is the terpenes. These may be aliphatic, alicyclic, or bi and tricyclic of varying degrees of unsaturation up to three double bonds. Also present are aromatic and heterocyclic compounds, in addition to linear and branched chain structures up to large ring compounds.
It is not uncommon for an essential oil to contain over two hundred components and often the trace impurities are essential to the odour and flavour. Many types of functional groups may be present including alcohol, aldehyde, ketone, acid, ester and ether substituents.
Essential oils are used as flavouring and fragrance agents in many applications. They are utilised extensively in personal care products such as bath oils and aromatherapy formulations. Essential oils are key components in toothpaste, mouthwash and lozenges.
Combinations can be found in almost every fragranced product, such as room fresheners, paper, printing ink, paint, candles, soap, polish, insect repellants, etc.
Essential oils used for flavouring are encountered in baked goods, snack food, soft drinks, liqueurs, tobacco, sauces, gravies, salad dressings and other food products.
Most, if sot all, essential oils are insoluble or exhibit very low solubility in water. This poses problems when the oil needs to be incorporated in an aqueous based formulation. Several methods of solubilising or dispersing essential oils in an aqueous medium have therefore been developed. For example a second solvent may be employed to effect dissolution, or a surfactant may be used to solubilise the oil or produce a dispersion of the essential oil in water. However, relatively large amounts of surfactant (1 to 8 parts surfactant for each part of essential oil) are frequently necessary to achieve the required level of aqueous solubility, and the use of such large amounts clearly has an impact on the overall balance and cost of the formulation. Improved processes for solubilising essential oils are therefore desirable.
It has now been discovered that by reaction of an essential oil with ethylene oxide, the oil can be rendered water soluble or autodispersible whilst still retaining much of the original odour and flavour characteristics of the unmodified starting material.
In one aspect, the present invention thus provides a method of treating an essential oil to render it water soluble or water dispersible, which method comprises reacting the oil with ethylene oxide.
The essential oils so modified are themselves novel and constitute a further aspect of the present invention.
The following list gives examples of some essential oils that may be made water soluble or water dispersible using the method of the present invention: allspice (pimenta berry), almond, amyris, anise, aniseed, basil, bay, bergamot, birch, bois de rose (rosewood).
camphor, canaga, caraway, cardamon, cassia, cedarwood, cinnamon, citronella, clove, coriander, coumarin, cumin seed, eucalyptus, geranium, ginger, grapefruit, heliotropin, jasmine, juniper, labdanum, lavandin, lavender, lemon, lemongrass, lime, iitsea cubeba, menthol/mint, musks, neroli, nutmeg, ocotea orange-bitter, orange-sweet, origanum, orris root, palmarosa, patchouli, pepper-black, peppermint, petitgrain bigarde, pimento, pine, pinus pumilo, rose, rosemary, sage dalmation, sage clary, sandalwood, spearmint, spike lavender, thuja (cedarleaf), thyme, turpentine. vanillin, vetivert, wintergreen, ylang ylang.
It will be appreciated that in view of the range and complexity of essential oils and the large variation in the number and type of nucleophilic centres potentially available for ethoxylation, the level of ethylene oxide addition required to effect water solubility will vary depending on the specific essential oil being considered.
Generally, the modified essential oil would contain from 20% to 90% by weight of ethylene oxide, and preferably from 40% to 80% by weight (although amounts outside these ranges can be used). As a generality, the degree of ethoxylation will be limited to that required for the desired solubility, but this is not essential. It can, however, assist in ensuring maximum retention of flavour and odour qualities.
Some essential oils possess a low or nondetectable level of nucleophilic centres for direct reaction with ethylene oxide. According to a further aspect of the present invention, we have found that such oils can be rendered water soluble or water dispersible by adding a coreactant which can be ethoxylated in admixture with the essential oil. Thus, a polyol or partial fatty acid ester of a polyol is added as a coreactant to the essential oil, and the resultant mixture is ethoxylated as described previously.
Suitable polyols include, for example: glycerol; polyglycerol (formed by self condensation of the glycerol unit-typically 2 to 6 monomeric glycerol units would be utilised; ethylene glycol; poly(ethylene glycol); propylene glycol; poly(propylene glycol); sorbitol; trimethylolpropane; di(trimethylolpropane); pentaerythritol; and di(pentaerythri,tol7.
The partial fatty acid ester is a compound formed by the reaction of a polyol and a fatty acid, in which not all of the hydroxyl groups in the polyol have been esterified with the fatty acid reactant. Thus the partial fatty acid ester includes both ester and hydroxyl functional groups.
The fatty acid that is reacted with the polyol is desirably a fatty acid derived from animal fats or oil.
Preferably, the fatty acid is a straight or branched chain carboxylic acid having between 6 and 24 carbon atoms.
Examples of suitable fatty acids are: caproic (6:0); caprylic (8:0); capric (10:0); lauric (12:0); myristic (14:0); palmitic (16:0); stearic (18:0); arachidic (20:0); behinic (22:0); lignoceric (24:0); oleic (18:1); erucic (22:1); nervonic (24:1); linoleic (18:2); linolenic (18:3); and ricinoleic acid. The first number in brackets after the name of the fatty acid refers to the number of carbon atoms in the acid, while the second number refers to the number of double bonds.
The partial fatty acid ester may be formed by reacting any one of the above polyols with any of the above fatty acids. Suitable, partial fatty acid esters include: glycerol monostearate; glycerol distearate; ethylene glycol monooleate; diglycerol monooleate; and ethylene glycol mono palpitate.
In practice the coreactant can be selected on the basis of low toxicity and cost, together with the ability to achieve good solubility or dispersibility of the essential oil, and to maintain the desirable odour and flavour characteristics of the unmodified oil. Glycerol and polyglycerol, formed by self condensation of the glycerol unit, or partial fatty acid esters thereof, are preferred as coreactants in view of their natural sourcing and low toxicity profile.
The polyol or partial fatty acid ester would comprise typically J% to 10% by weight of the reaction mixture, preferably 2%. to 8% w/w (although amounts outside these ranges can be used).
It will be appreciated that, where a coreactant is employed, a number of ethoxylated end-products is possible.
Ethoxylation can occur at suitable nucleophilic centres on the essential oil, at the hydroxyl groups on the glycerol or glycerol derivative and at any new nucleophilic centres arising from reaction of glycerol or glycerol derivative with the essential oil, eg through transesterification.
In cases where a coreactant is employed, the resulting reaction mixture is rendered water soluble or water dispersible by the presence of ethoxylated species acting as autodispersants. In addition, the odour and flavour characteristics of the unmodified essential oils are substantially maintained.
The invention also includes essential oils which have been ethoxylated in admixture with a coreactant.
In order that the invention may be more fully understood, the following Examples are given by way of illustration only.
Example 1 Geraniol (3,7-dimethyl-2,6-octadiene-l-ol) (50% by weight of charge), and ethylene oxide (50% by weight) were reacted in a 600ml capacity reactor at a temperature of 150 to 160 deg C and a pressure of 2 to 3 bar, using 50% potassium hydroxide as catalyst (0.2% by weight on total reactants). The rate of ethylene oxide addition was 1.7 to 3.3 g/min.
Residual catalyst in the ethoxylated product was neutralised with lactic acid.
The ethoxy (50%) geraniol reaction product was added to water at both 1% and 10% by weight. In each case, a dispersion of oil in water was produced which slowly separated in to separate layers at the 10% concentration.
Example 2 Geraniol yasreacted as in Example 1 but the level of ethoxylation was increased to 60% by weight.
The ethoxy (60%) geraniol reaction product produced a clear colourless solution when added to distilled water at both 1% and 10% by weight.
Example 3 Linalool (3,7-dimethyl-1,6-octadiene-3-ol) (40% by weight of charge), and ethylene oxide (60% by weight of charge) were reacted together using the procedure described in Example 1.
The resulting ethoxy (60%) linalool produced a stable white dispersion when added to distilled water at 1% by weight. When incorporated into distilled water at a level of 10% by weight, a clear yellow solution was obtained from which a small amount of colourless oil eventually separated on the surface.
The strong odour of the unmodified linalool was retained in the ethoxylated derivative.
Example 4 Lemon oil (26% by weight), glycerol (4% by weight) and ethylene oxide (70% by weight) were reacted together in a 600ml reactor at a temperature of 150 deg C to 160 deg C and a pressure of 2 to 3 bar in the presence of 50% potassium hydroxide solution as catalyst (0.2% by weight of total charge).
Residual catalyst in the ethoxylated product was neutralised with lactic acid.
The ethoxylated product formed a stable dispersion when added to distilled water at 1% and 10% by weight.
The characteristic odour of the lemon oil was retained in the ethoxylated product.
Example 5 Eucalyptus oil (26% by weight), glycerol (4% by weight), and ethylene oxide (70% by weight) were reacted together using the procedure described in Example 4.
The ethoxylated product produced stable dispersions in distilled water at 1% and 10% by weight.
The strong characteristic odour of eucalyptus oil was retained in the ethoxylated variant.
Example 6 Thyme oil (26% by weight), glycerol (4% by weight) and ethylene oxide (70% by weight) were reacted together using the procedure described in Example 5.
The resulting ethoxylated product afforded a stable dispersion in distilled water at a level of 1% by weight.

Claims (22)

CLAIMS:
1. A method of treating an essential oil to render it water soluble or water dispersible, comprising reacting the oil with ethylene oxide.
2. A method according to claim 1, wherein 10 to 80 wt % of the essential oil is reacted with 20 to 90 wt % of ethylene oxide.
3. A method according to claim 1 or 2, wherein 20 to 60 wt % of the essential oil is reacted with 40 to 80 wt % of ethylene oxide.
4. A method according to claim 1, 2 or 3, further comprising adding a coreactant that can be ethoxylated by ethylene oxide.
5. A method according to claim 4, wherein the coreactant comprises 1 to 10 wt 7. of the total reaction mixture.
6. A method according to claim 4 or 5, wherein the coreactant comprises 2 to 8 wt % of the total reaction mixture.
7. A method according to claim 4, 5 or 6, wherein the coreactant is a polyol.
8. A method according to claim 7, wherein the polyol is one or more of glycerol, polyglycerol, ethylene glycol, poly(ethylene glycol),.propylene glycol, poly(propylene glycol), sorbitol, trimethylolpropane, di(trimethylolpropane), pentaerythritol and di(pentaerythritol).
9. A method according to any one of claims 4 to 8, wherein the coreactant is glycerol.
10. A method according to claim 4, 5 or 6, wherein the coreactant is a partial fatty acid ester formed by reaction of a polyol and a fatty acid.
11. A method according to claim 10, wherein the polyol is one or more of glycerol, polyglycerol, ethylene glycol, poly(ethylene glycol), propylene glycol, poly(propylene glycol), sorbitol, trimethylolpropane, di(trimethylolpropane), pentaerythritol and di(pentaerythritol).
12. A method according to claim 10 or 11, wherein the fatty acid is a straight or branched chain carboxylic acid having between 6 and 24 carbon atoms.
13. A method according to claim 10, 11 or 12, wherein the fatty acid is one or more of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behinic acid, lignoceric acid, oleic acid, erucic acid, nervonic acid, linoleic acid, linolenic acid and ricinoleic acid.
14. A method according to any one of claims 10 to 13, wherein the partial fatty acid ester is glycerol distearate.
diglycerol monooleate, or ethylene glycol monopalmitate.
15. A method according to any preceding claim, wherein the essential oil comprises an essential oil as hereinbefore described.
16. A water soluble or water dispersible composition comprising an ethoxylated essential oil.
17. A composition according to claim 16, wherein the essential oil comprises an essential oil as hereinbefore described.
18. A composition according to claim 16 or 17, further comprising an ethoxylated coreactant.
19. A composition according to claim 18, wherein the coreactant is a polyol.
20. A composition according to claim 18, wherein the coreactant is a partial fatty acid ester.
21. A method of treating an essential oil to render it water soluble or water dispersible, substantially as herein described with reference to the Examples.
22. A water soluble or water dispersible composition substantially as herein described with reference to the Examples.
GB9601767A 1995-01-31 1996-01-30 Solubilised essential oils Withdrawn GB2297557A (en)

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GBGB9501861.0A GB9501861D0 (en) 1995-01-31 1995-01-31 Solubilised essential oils

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000017294A1 (en) * 1998-09-21 2000-03-30 Auberger Gerard Water-soluble concentrate obtained for an emulgator or water-solubilising phase and a complex of liquid lipophile substances of plant origin
DE10046432A1 (en) * 2000-09-20 2002-04-04 Henkel Kgaa New terpene alcohol ethers, used as oil component in skin care formulation, and adducts used in skin cleanser or shampoo, are reaction products of terpene alcohol and long-chain epoxide compound
EP1203589A1 (en) * 2000-10-27 2002-05-08 Basf Aktiengesellschaft Use of terpene alcohol ethoxylates as solubilizers in cosmetic or pharmaceutical formulations or in concentrates for food compositions
US20140271948A1 (en) * 2011-02-15 2014-09-18 Freshguard Defense Llc Antimicrobial solution for use with dental appliances
US10532124B2 (en) 2012-12-27 2020-01-14 Kimberly-Clark Worldwide, Inc. Water soluble farnesol analogs and their use
US10717946B2 (en) 2012-12-27 2020-07-21 Kimberly-Clark Worldside, Inc. Water soluble essential oils and their use

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112189875A (en) * 2020-10-23 2021-01-08 湖北中烟工业有限责任公司 Polysweet fruit refined extract for cigarettes as well as preparation method and application thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4975090A (en) * 1986-05-26 1990-12-04 Chemische Fabrik Stockhausen Gmbh Process for the preparation of room temperature flowable derivatives of natural fats and oils and their use

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4975090A (en) * 1986-05-26 1990-12-04 Chemische Fabrik Stockhausen Gmbh Process for the preparation of room temperature flowable derivatives of natural fats and oils and their use

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000017294A1 (en) * 1998-09-21 2000-03-30 Auberger Gerard Water-soluble concentrate obtained for an emulgator or water-solubilising phase and a complex of liquid lipophile substances of plant origin
FR2784601A1 (en) * 1998-09-21 2000-04-21 Gerard Auberger WATER-SOLUBLE CONCENTRATE OBTAINED FROM AN EMULGATOR OR WATER-SOLUBILIZING PHASE AND A COMPLEX OF LIQUID LIPOPHILIC MATERIALS OF PLANT ORIGIN
US6645516B2 (en) 1998-09-21 2003-11-11 Auberger Gerard Hydrosoluble composition comprising lipophilic vegetable material and at least two ecologically optimized surfactants
DE10046432A1 (en) * 2000-09-20 2002-04-04 Henkel Kgaa New terpene alcohol ethers, used as oil component in skin care formulation, and adducts used in skin cleanser or shampoo, are reaction products of terpene alcohol and long-chain epoxide compound
EP1203589A1 (en) * 2000-10-27 2002-05-08 Basf Aktiengesellschaft Use of terpene alcohol ethoxylates as solubilizers in cosmetic or pharmaceutical formulations or in concentrates for food compositions
US20140271948A1 (en) * 2011-02-15 2014-09-18 Freshguard Defense Llc Antimicrobial solution for use with dental appliances
US10182573B2 (en) * 2011-02-15 2019-01-22 Freshguard Defense Llc Antimicrobial solution for use with dental appliances
US10532124B2 (en) 2012-12-27 2020-01-14 Kimberly-Clark Worldwide, Inc. Water soluble farnesol analogs and their use
US10717946B2 (en) 2012-12-27 2020-07-21 Kimberly-Clark Worldside, Inc. Water soluble essential oils and their use
US11383003B2 (en) 2012-12-27 2022-07-12 Kimberly-Clark Worldwide, Inc. Water soluble farnesol analogs and their use

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GB9601767D0 (en) 1996-04-03
GB9501861D0 (en) 1995-03-22

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