CN103033583A - Method for enriching and measuring ester components in natural perfume by using ionic liquid - Google Patents
Method for enriching and measuring ester components in natural perfume by using ionic liquid Download PDFInfo
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- CN103033583A CN103033583A CN2012105383275A CN201210538327A CN103033583A CN 103033583 A CN103033583 A CN 103033583A CN 2012105383275 A CN2012105383275 A CN 2012105383275A CN 201210538327 A CN201210538327 A CN 201210538327A CN 103033583 A CN103033583 A CN 103033583A
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Abstract
The invention relates to a method for enriching and measuring ester components in natural perfume by using an ionic liquid, belonging to the field of chemical industry. The method comprises the following steps: (1) inserting a needle point of a trace sampler to below an ionic liquid level, slowly extracting a certain volume of ionic liquid, fixing the trace sampler above an extraction flask, and slowly lowering a piston to form an ionic liquid hanging drop at the needle point of the trace sampler; (2) adding a solvent and a solution ionic strength regulator into the extraction flask, adding a mixed ester compound standard solution or a natural perfume solution, putting the ionic liquid hanging drop prepared in the step (1) at the headspace of the extraction flask, extracting at a certain temperature and a certain stirring speed for some time, and recovering the ionic liquid; and (3) immediately inserting the trace sampler into an injection port of a gas chromatography or gas chromatography-massspectrometer to carry out detection. The method provided by the invention is green and environment-friendly, greatly enhances the extraction efficiency, has the advantages of high sensitivity and high accuracy, and is obviously superior to the prior art.
Description
Technical field
The present invention relates to the method that a kind of ionic liquid is used for natural perfume material ester constituents Enrichment and determination, belong to chemical field.
Background technology
Ester type compound is the important component part of fresh flower, the fragrant composition of fruit, and they mostly have the fragrance of a flower, fruital, aroma or sweet fragrance.Ester perfume occupies the status of particular importance in perfume industry, be preparation daily chemical essence, food flavor and the indispensable raw material of tobacco and wine essence.At present, the spices and essence analytical approach mainly is gas chromatography, gas chromatography mass spectrometry and high performance liquid chromatography (Bicchi C, Rubiolo P, Cordero C.
Analytical and Bioanalytical Chemistry, 2006,384:53-56).But said method is still sensitive not, and the compound that some threshold values are lower, aroma strength is very large is difficult to direct mensuration owing to content is very low, accurately very necessary to guaranteeing analysis result to pre-separation and the enrichment of sample.
Liquid-phase micro-extraction is a kind of novel Sample Pretreatment Technique (the Liu H that grows up in 1996, Dasgupta P K. Anal. Chem., 1996,68:1817-1821), head space-single micro-extraction (headspace single drop microextraction, HS-SDME) namely is wherein a kind of (Przyjazny A, Kokosa J M. J. Chromatography A, 2002,977:143-153).HS-SDME is mainly by hanging on the microsyringe syringe needle with an organic solvent, and places the air at solution to be measured top, the volatile matter in the separation and concentration solution.This technical operation is simple, convenient, centralized procurement sample, extraction and simmer down to one, and also cost is low more than solid-phase microextraction, thereby be widely used in the analysis fields such as environment, food, medicine and biological sample.But the employed extractant of HS-SDME is generally volatile organic solvent, and the extraction droplet volume is little, and extraction time is shorter, is difficult for high-temperature extraction, causes the multiple of enrichment and reappearance all not ideal enough.
In recent years, the sample pre-treatments that is applied in single dropping liquid-phase microextraction of ionic liquid (Ionic Liquids, ILs) has been received better effects.It has not only eliminated many drawbacks that organic solvent brings, and extraction efficiency improves (Aguilera-Herrador E, Lucena R greatly, Cardenas S, Valcarcel M. J. Chromatography A, 2009,1201:106-111).ILs has the characteristics such as extremely low vapour pressure, non-volatile, good thermal stability, viscosity and density be large, can also regulate character (the Anderson J L such as its polarity, dissolubility by the combination that changes the yin, yang ion, Armstrong D W, Wei G T. Anal. Chem., 2006,78:2892 – 2902).At present, most widely used ionic liquid be 1-alkyl-3-methylimidazole hexafluorophosphate (Zhao F Q, Li J, Zeng B Z. Chin. J Anal. Chem., 2009,37:939-942).Yet, this type of ionic liquid only can change the alkyl chain length on the imidazole ring 1-position N, be subjected to the carbon number of the little restriction alkyl chain of liquid journey scope usually less than 8, the designability of ionic liquid is poor, gives and to want that the ester perfume analysis that improves enrichment times by being increased in level of dissolution in the ionic liquid brings larger difficulty.Therefore set up more sensitive, reliable and green, easy analytical approach and seem particularly important for Enrichment and determination natural perfume material ester constituents.
Summary of the invention
The technical problem to be solved in the present invention is that the extraction efficiency that exists for the method for terpene ester class in the existing natural perfume material and aromatic ester composition Enrichment and determination is not high, enrichment times is low and the deficiency of poor reproducibility, provide a kind of new from natural perfume material the method for Enrichment and determination ester constituents, the method is simple to operate, sensitivity and enrichment times high, favorable reproducibility, environmental protection, can not cause environmental pollution.
The inventor finds through widely research and test repeatedly, adopt the novel imidazole ionic liquid to substitute effumability organic solvent or the 1-alkyl-3-methylimidazole hexafluorophosphate ionic liquid that uses in traditional liquid-phase micro-extraction, not only can eliminate the environmental pollution that causes because of the organic solvent volatilization, and new ion liquid abstraction system has than organic solvent and 1-alkyl-higher percentage extraction of 3-methylimidazole hexafluorophosphate ion liquid system.The inventor further is in optimized selection extraction conditionss such as extractant volume, ionic strength, extraction temperature, extraction times, has finally realized efficiently concentrating and the mensuration of ester constituents in the natural perfume material, thereby has finished the present invention.
The present invention solves the problems of the technologies described above the technical scheme that adopts: a kind of ionic liquid is used for the method for natural perfume material ester constituents Enrichment and determination, comprises
(1) the microsyringe needle point is inserted under the ionic liquid liquid level, slowly extract the ionic liquid of certain volume, then microsyringe is fixed in the extraction flask top, slowly reduce piston, form the ionic liquid hanging drop at the needle point place of microsyringe;
(2) in extraction flask, add solvent and solution ion strength correctives, add again mixed ester compounds standard solution or natural perfume material solution, the ionic liquid hanging drop that step (1) is prepared places the head space place of extraction flask, after extraction a period of time under uniform temperature and the stirring rate, regain ionic liquid;
(3) microsyringe is inserted immediately the injection port of gas chromatography or gas chromatograph-mass spectrometer (GCMS), detect.
Wherein, the kation of ionic liquid is to be selected from 1 of Chemical formula 1,3-two R base glyoxaline cation.
Wherein, R is substituting group, and R can represent independently of one another:
The straight or branched alkyl of-carbon number between 1 ~ 10,
The straight or branched thiazolinyl with one or more pair keys of-carbon number between 2 ~ 10,
The straight or branched alkynyl with one or more three keys of-carbon number between 2 ~ 10,
Saturated, fractional saturation or the complete undersaturated naphthenic base of-carbon number between 5 ~ 7, it is had 1 ~ 6 alkyl and is replaced.
And negative ion comprises hexafluorophosphoricacid acid ions (PF
6 -), bis trifluoromethyl sulfimide ion (NTf
2 -), four cyano borate ion (B (CN)
4 –), trifluoromethane sulfonic acid radical ion (CF
3SO
3 –) or methoxyl sulfonate ion (CH
3OSO
3 –).
Described ionic liquid is any kation and the compound that is selected from above-mentioned any negative ion composition that is selected from the Chemical formula 1, or its potpourri.
The extraction volume of the ionic liquid (extractant) described in the step (1) is 0.5 ~ 2.5 μ L.
Solvent described in the step (2) is ddH
2O water 6-12mL.
Solution ion strength correctives described in the step (2) is sodium chloride, and its concentration is 0.1 ~ 0.36 g/mL.
Ester type compound described in the step (2) has the structure of Chemical formula 2, wherein, and R
1, R
2Substituting group, R
1The straight or branched alkyl of carbon number between 1 ~ 20; R
2Being the terpene base of straight chain, side chain or the band of carbon number between 6 ~ 20, also can be the aromatic radical of carbon number between 6 ~ 20.
Chemical formula 2
Mixed ester compounds standard solution described in the step (2) or natural perfume material solution 1 μ L, concentration are 0.0001 ~ 0.1 g/mL, and this solution solvent for use is absolute ethyl alcohol.
Extraction temperature described in the step (2) is 20 ~ 60 ℃.
Stirring rate described in the step (2) is 200 ~ 2000 r/mim.
Extraction time described in the step (2) is 5 ~ 90 min.
Beneficial effect of the present invention: studies show that resulting method has very high sensitivity, the detection limit of ester perfume reaches 0.20 ~ 6.0 μ g/L, and enrichment times is 500 ~ 1500.
The raw material that the present invention is used or reagent except specifying, equal commercially available getting.
Each preferred version of the present invention can be used in combination mutually.
Embodiment
The below further specifies the present invention with embodiment, but the present invention is not limited.
Embodiment 1
Extract 0.5 μ L ionic liquid 1 with microsyringe, 3-di-n-hexyl imidazoles hexafluorophosphate, in 15 mL extraction flasks, add 10 mL distilled waters and 0.36 g/mL sodium chloride, the standard solution 1.0 μ L that add again the mixed ester compounds of 0.01 g/mL geranyl acetate, benzyl acetate and phenethyl acetate, extraction flask is sealed, passing rubber cushion with microsyringe inserts in the bottle, release drop and carry out headspace extraction, be that 40 ℃, stirring rate are under 1000 r/min in extraction temperature, after extracting 30 min the ionic liquid drop is regained, carried out Gc-ms.The detection limit of 3 kinds of ester perfumes reaches 0.50 ~ 5.5 μ g/L, and enrichment times is 480 ~ 1410.
Embodiment 2
Extract 1.0 μ L ionic liquids 1 with microsyringe, 3-diisobutyl imidazoles bis trifluoromethyl sulfimide salt, in 15 mL extraction flasks, add 6 mL distilled waters and 0.30 g/mL sodium chloride, add again 0.001 g/mL neryl propionate, the standard solution 1.0 μ L of phenylpropyl acetate and 2-Methyl Butyric Acid phenethyl ester mixed ester compounds, extraction flask is sealed, passing rubber cushion with microsyringe inserts in the bottle, release drop and carry out headspace extraction, it is 30 ℃ in extraction temperature, stirring rate is under 500 r/min, after extracting 25 min the ionic liquid drop is regained, carried out Gc-ms.The detection limit of 3 kinds of ester perfumes reaches 0.26 ~ 4.9 μ g/L, and enrichment times is 760 ~ 1450.
Embodiment 3
Extract 1.5 μ L ionic liquids 1 with microsyringe, 3-diallyl imidazoles four cyano borate, in 15 mL extraction flasks, add 12 mL distilled waters, 0.20 g/mL sodium chloride and stirrer, add again 0.005 g/mL citronellyl acetate, the standard solution 1.0 μ L of neopentanoic acid phenethyl ester and acetic acid trimethylbenzene propyl ester mixed ester compounds, extraction flask is sealed, passing rubber cushion with microsyringe inserts in the bottle, release drop and carry out headspace extraction, it is 20 ℃ in extraction temperature, stirring rate is under 1500 r/min, after extracting 20 min the ionic liquid drop is regained, carried out Gc-ms.The detection limit of 3 kinds of ester perfumes reaches 0.73 ~ 5.8 μ g/L, and enrichment times is 520 ~ 1369.
Embodiment 4
Extract 2.0 μ L ionic liquids 1 with microsyringe, 3-dicyclohexyl imidazoles hexafluorophosphate, in 15 mL extraction flasks, add 10 mL distilled waters, 0.10 g/mL sodium chloride and stirrer, add again 0.1 g/mL bergamio, menthyl acetate, the standard solution 1.0 μ L of citronellyl isobutyrate and sad paracresol mixed ester compounds, extraction flask is sealed, passing rubber cushion with microsyringe inserts in the bottle, release drop and carry out headspace extraction, it is 40 ℃ in extraction temperature, stirring rate is under 800 r/min, after extracting 15 min the ionic liquid drop is regained, carried out Gc-ms.The detection limit of 4 kinds of ester perfumes reaches 0.44 ~ 3.2 μ g/L, and enrichment times is 650 ~ 1216.
Embodiment 5
Extract 1.0 μ L ionic liquids 1 with microsyringe, 3-di-n-butyl imidazoles trifluoromethyl sulfonic acid, in 15 mL extraction flasks, add 10 mL distilled waters, 0.36 g/mL sodium chloride and stirrer, add again 0.01 g/mL Rosa Damascana solution, 1.0 μ L, extraction flask is sealed, passing rubber cushion with microsyringe inserts in the bottle, release drop and carry out headspace extraction, be that 30 ℃, stirring rate are under 1000 r/min in extraction temperature, after extracting 30 min the ionic liquid drop is regained, carried out Gc-ms.The content that records geranyl acetate in the Rosa Damascana, neryl propionate, benzyl acetate, phenethyl acetate is respectively 0.116 mg/mL, 0.024 mg/mL, 0.003 mg/mL and 0.389 mg/mL, and recovery of standard addition is between 96.7 % ~ 103.8 %.
Embodiment 6
Extract 1.0 μ L ionic liquids 1 with microsyringe, 3-two n-pentyl imidazoles methoxyl sulfonate, in 15 mL extraction flasks, add 8 mL distilled waters, 0.30 g/mL sodium chloride and stirrer, add again 0.01 g/mL white orchid essential oil solution, 1.0 μ L, extraction flask is sealed, passing rubber cushion with microsyringe inserts in the bottle, release drop and carry out headspace extraction, be that 35 ℃, stirring rate are under 800 r/min in extraction temperature, after extracting 25 min the ionic liquid drop is regained, carried out Gc-ms.The content that records phenethyl acetate in the white orchid essential oil, phenylethyl propionate, 2-Methyl Butyric Acid phenethyl ester, farnesyl acetate is respectively 0.006 mg/mL, 0.008 mg/mL, 0.042 mg/mL and 0.198 mg/mL, and recovery of standard addition is between 95.3 % ~ 104.5 %.
Claims (1)
1. an ionic liquid is used for the method for natural perfume material ester constituents Enrichment and determination, it is characterized in that
Described ionic liquid is:
Kation is 1,3-, two R base glyoxaline cation, has the structure of Chemical formula 1,
Chemical formula 1
Wherein, R is substituting group, and R represents independently of one another:
The straight or branched alkyl of-carbon number between 1 ~ 10,
The straight or branched thiazolinyl with one or more pair keys of-carbon number between 2 ~ 10,
The straight or branched alkynyl with one or more three keys of-carbon number between 2 ~ 10,
Saturated, fractional saturation or the complete undersaturated naphthenic base of-carbon number between 5 ~ 7, it is had 1 ~ 6 alkyl and is replaced;
And negative ion comprises hexafluorophosphoricacid acid ions PF
6 -, bis trifluoromethyl sulfimide ion NTf
2 -, four cyano borate ion B (CN)
4 –, trifluoromethane sulfonic acid radical ion CF
3SO
3 –Or methoxyl sulfonate ion CH
3OSO
3 –
Described ionic liquid is any kation and the compound that is selected from above-mentioned any negative ion composition that is selected from the Chemical formula 1, or its potpourri;
This method step is:
(1) the microsyringe needle point is inserted under the ionic liquid liquid level, slowly extract the ionic liquid of 0.5 ~ 2.5 μ L, then microsyringe is fixed in the extraction flask top, slowly reduce piston, form the ionic liquid hanging drop at the needle point place of microsyringe;
(2) in the 15mL extraction flask, add ddH
2O 6-12mL and solution ion strength correctives, add again mixed ester compounds standard solution or natural perfume material solution 1 μ L, concentration is 0.0001 ~ 0.1 g/mL, the ionic liquid hanging drop that step (1) is prepared places the head space place of extraction flask, after under 20 ~ 60 ℃ and 200 ~ 2000 r/min stirring rates, extracting 5 ~ 90 min, regain ionic liquid;
Described solution ion strength correctives is sodium chloride, and its concentration is 0.1 ~ 0.36 g/mL;
Described ester type compound has the structure of Chemical formula 2, wherein, and R
1, R
2Substituting group, R
1The straight or branched alkyl of carbon number between 1 ~ 20; R
2The terpene base of straight chain, side chain or the band of carbon number between 6 ~ 20, or R
2The aromatic radical of carbon number between 6 ~ 20;
Chemical formula 2
The concentration of mixed ester compounds standard solution or natural perfume material solution is 0.0001 ~ 0.1 g/mL, and this solution solvent for use is absolute ethyl alcohol;
(3) microsyringe is inserted immediately the injection port of gas chromatography or gas chromatograph-mass spectrometer (GCMS), detect.
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| CN103656721A (en) * | 2013-12-10 | 2014-03-26 | 江南大学 | Long-acting fragrance fixing agent |
| CN104531823A (en) * | 2014-12-18 | 2015-04-22 | 江南大学 | Method for carrying out enzymatic resolution on DL-menthol by taking ionic liquid as environment-friendly medium |
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Application publication date: 20130410 |