CN103740782B - The preparation method of C5 fatty acid monosaccharide ester and the application in Medicated cigarette and Medicated cigarette - Google Patents
The preparation method of C5 fatty acid monosaccharide ester and the application in Medicated cigarette and Medicated cigarette Download PDFInfo
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Abstract
The invention discloses the preparation method of a kind of C5 fatty acid monosaccharide ester and the application in Medicated cigarette and Medicated cigarette, described preparation method comprises the steps: that (1) prepares mixed ionic liquid, in mixed ionic liquid, hydrophilic ionic-liquid is 1:0.1～1:10 with the volume ratio of hydrophobic ionic liquid；(2) the monosaccharide aqueous solution of mixed ionic liquid volume 0.1～10 times being added mix homogeneously in mixed ionic liquid, at 50 DEG C～60 DEG C, concentrating under reduced pressure is except removing undissolved monosaccharide after water, obtains over-saturation monosaccharide ionic liquid；(3) in over-saturation monosaccharide ionic liquid, C5 fatty acid is added, in over-saturation monosaccharide ionic liquid, the mass concentration of C5 fatty acid is 10～1000g/L, add lipase in the ratio that ratio is 5～500U/g of lipase with C5 fatty acid consumption again and form reaction system, desiccant is added except water in reaction system, under the reaction temperature of 40～55 DEG C, under lipase-catalyzed, C5 fatty acid and monosaccharide reaction generate C5 fatty acid monosaccharide ester；(4) extract and purification C5 fatty acid monosaccharide ester.
Description
Technical field
The present invention relates to the preparation of fatty acid monosaccharide ester, particularly relate to the preparation of a kind of C5 fatty acid monosaccharide ester
Method and the application in Medicated cigarette and Medicated cigarette.
Background technology
Fatty acid, especially C5 carbon chain lengths fatty acid is the fragrance matter that in Nicotiana tabacum L., a class is important, can be Nicotiana tabacum L.
Goods increase vinosity, fruit and the note of cheese sample sweet taste, makes flue gas strengthen.But low carbon chain fat in these
Fat acid has volatile characteristic, can gradually volatilize, owing to Medicated cigarette is when burning and sucking with when depositing at Cigarette processing
Not only combustion zone has high temperature, and is pyrolyzed distillation zone and also has at a relatively high temperature, therefore, burns and sucks
Time these acid can drastically volatilize, thus have impact on the quality of cigarette smoke and inhale before and after taste inconsistent.Therefore,
How to improve low carbon chain fatty acid stability in aspiration procedure, be the hot topic of current Nicotiana tabacum L. scientific and technical personnel research
Field.
Summary of the invention
The technical problem to be solved is: make up above-mentioned the deficiencies in the prior art, proposes a kind of C5 fat
The preparation method of fat acid monosaccharide ester and the application in Medicated cigarette and Medicated cigarette, can improve C5 fatty acid and aspirate
Stability in journey.
The technical problem of the present invention is solved by following technical scheme: a kind of satisfied fatty acid monosaccharide ester
Preparation method, comprises the steps:
(1) preparation mixed ionic liquid, in described mixed ionic liquid, hydrophilic ionic-liquid and hydrophobicity
The volume ratio of ionic liquid is 1:0.1～1:10；
(2) the monosaccharide aqueous solution of described mixed ionic liquid volume 0.1～10 times is added described hybrid ionic liquid
Mix homogeneously in body, at 50 DEG C～60 DEG C, concentrating under reduced pressure is except removing undissolved monosaccharide after water, obtains over-saturation
Monosaccharide ionic liquid；
(3) in described over-saturation monosaccharide ionic liquid add C5 fatty acid, described over-saturation monosaccharide from
The mass concentration of C5 fatty acid described in sub-liquid is 10～1000g/L, then presses lipase and described C5 fat
The ratio that ratio is 5～500U/g of acid consumption adds lipase and forms reaction system, adds in described reaction system
Enter desiccant except water, under the reaction temperature of 40～55 DEG C, described lipase-catalyzed under, described C5 fat
Acid and monosaccharide reaction generate C5 fatty acid monosaccharide ester；
(4) extract and C5 fatty acid monosaccharide ester described in purification.
It has been investigated that fatty acid to be combined the stability that can be greatly improved fatty acid in Nicotiana tabacum L. with saccharide, profit
By the regioselectivity of lipase, can synthesize from saccharide and fatty acid easily and be esterified location-specific sugar
Ester, and reaction condition is gentle, easy to operate；Inventor studies discovery, although ionic liquid is to monosaccharide, many
Sugar has certain dissolubility, if glucose is at hydrophilic ionic-liquid such as [Bmim] [TfO]
(1-butyl-3-methylimidazoium trifluoromethanesulfonate, 1-butyl-3-Methylimidazole. trifluoro
Mesylate) in dissolubility be 4.8g/L(25 DEG C), but with traditional method by monosaccharide crystal add hydrophilic
In property ionic liquid, its dissolubility is the lowest, it is difficult to meet the needs of high conversion, and inventor also finds
When carrying out enzymatic clarification C5 fatty acid monosaccharide ester in single ionic liquid such as [Bmim] [TfO], enzyme reduction alive is fast
Speed thus cause the recycling rate variance of immobilized enzyme, cost raises, is unfavorable for commercial production, and hydrophobicity from
Sub-liquid such as [Bmim] [Tf2N] (1-butyl-3-methylimidazolium
Bis [(trifluoromethyl) sulfonyl] amide, 1-butyl-3-Methylimidazole. bis-trifluoromethylsulfoandimide salt) in,
The dissolubility of monosaccharide is the least, but the stability of enzyme is higher.Inventor also has surprisingly found that, if using tradition side
Method is prepared over-saturation monosaccharide ionic liquid and (will be added and rise high-temperature in ionic liquid and the most slowly drop by monosaccharide crystal
Wen Hou, removes undissolved monosaccharide) time, the dissolubility of monosaccharide is the most relatively low, and monosaccharide is in ionic liquid
Dissolubility is unstable, and crystal easily separates out, and should not be used in the preparation of the C5 fatty acid monosaccharide ester of the present invention, and
Use the method in step of the present invention (2) to prepare over-saturation monosaccharide ionic liquid, monosaccharide can be significantly improved and exist
Dissolubility in ionic liquid, and crystal be difficult to separate out.
Satisfied fatty acid monosaccharide ester prepared by a kind of described preparation method application in Medicated cigarette, by described C5
The independent wiring solution-forming of fatty acid monosaccharide ester or allocate in conventional tobacco spice sprays in the way of perfuming or charging
In tobacco, based on the weight of tobacco, the addition weight of described C5 fatty acid monosaccharide ester is
0.0005%-0.05%。
The C5 fatty acid monosaccharide ester that the present invention is obtained by said method has typical fruit flavouring, can be used for
In perfume industry, above-mentioned C5 fatty acid monosaccharide ester is added to cigarette shreds and is found by test of smokeing panel test, its
There is obvious soft flue gas, improve flue gas drying sense, promote the effect of flue gas quality.
A kind of Medicated cigarette, is added with the C5 fatty acid monosaccharide ester that described method obtains in described Medicated cigarette.
The present invention has the further advantage that the present invention calculates with C5 fatty acid substrate, C5 fatty acid monosaccharide ester
Conversion ratio is 20% to 95%, in over-saturation monosaccharide ionic liquid prepared by the present invention, is urged by lipase
Changing prepared C5 fatty acid monosaccharide ester is that C5 fatty acid monosaccharide ester provides a kind of new and effective biocatalytic reaction
Method.
Detailed description of the invention
Below in conjunction with preferred embodiment the invention will be further described.
The present invention provides the preparation method of a kind of satisfied fatty acid monosaccharide ester, in one embodiment, including as follows
Step:
(1) preparation mixed ionic liquid, in described mixed ionic liquid, hydrophilic ionic-liquid and hydrophobicity
The volume ratio of ionic liquid is 1:0.1～1:10；
(2) the monosaccharide aqueous solution of described mixed ionic liquid volume 0.1～10 times is added described hybrid ionic liquid
Mix homogeneously in body, at 50 DEG C～60 DEG C, concentrating under reduced pressure is except removing undissolved monosaccharide after water, obtains over-saturation
Monosaccharide ionic liquid；
(3) in described over-saturation monosaccharide ionic liquid add C5 fatty acid, described over-saturation monosaccharide from
The mass concentration of C5 fatty acid described in sub-liquid is 10～1000g/L, then presses lipase and described C5 fat
The ratio that ratio is 5～500U/g of acid consumption adds lipase and forms reaction system, adds in described reaction system
Enter desiccant except water, under the reaction temperature of 40～55 DEG C, described lipase-catalyzed under, described C5 fat
Acid and monosaccharide reaction generate C5 fatty acid monosaccharide ester；
(4) extract and C5 fatty acid monosaccharide ester described in purification.
In some preferred embodiments, under conditions of above-described embodiment, can use in following optimum condition
At least one:
Described in step (1), volume ratio is 1:1～1:3, and under this volume ratio, the conversion ratio of reaction is higher, and
Enzyme reduction alive is less, again reacts with the enzyme reclaimed, and conversion ratio is the highest.
Described hydrophilic ionic-liquid be anion be TfO-、BF4 -、Cl-、Br-、HSO4 -、CF3CO2 -、
DMP-、DEP-、DBP-、AC-、NO3 -And ES-Hydrophilic ionic-liquid at least one；Described thin
Aqueous ionic liquid be anion be Tf2N-And PF6 -Hydrophobic ionic liquid at least one.
Preferably, described hydrophilic ionic-liquid is selected from:
1-alkyl-3-Methylimidazole. fluoroform sulphonate [Cnmim] [TfO], n=0, during 2,4,6,8(such as n=4
1-ethyl-3-methylimidazole trifluoro when 1-butyl-3-Methylimidazole. fluoroform sulphonate [Bmim] [TfO], n=2
Mesylate [Emim] [TfO])；
1-alkyl-3-methyl imidazolium tetrafluoroborate [Cnmim] [BF4], n=0,2,4,6,8；
1-alkyl-3-Methylimidazole. villaumite [Cnmim] [Cl], n=0,2,4,6,8；
3-methyl isophthalic acid-allyl imidazole villaumite [Amim] [Cl]；
Diethanolamine hydrochlorate [Hdea] [Cl]；
Different alkyl substituted bromination 1-alkyl-3-Methylimidazole. salt ionic liquid [Rmim] [Br] (R=E, B,
H；E represents that ethyl, B represent 1-butyl, and H represents 1-heptyl),
Acidic ion liquid 1-alkyl-3-methylimidazolium hydrogen sulphate salt [Cnmim] [HSO4], n=0,2,4,6,8,
1-alkyl-3-methylimidazolium nitrate ([Cnmim] [NO3], n=0,2,4,6,8,
1-alkyl-3-Methylimidazole. trifluoroacetate [Cnmim] [CF3CO2], n=0,2,4,6,8,
1-ethyl-3-methylimidazole dimethyl phosphate salt [Emim] [DMP],
1,3-methylimidazole dimethyl phosphate salt [Mmim] [DMP],
1,3-diethyl imidazolium diethyl phosphate salt [Eeim] [DEP],
1-ethyl-3-methylimidazole diethyl phosphate salt [Emim] [DEP],
1-butyl-3-Methylimidazole. dibutylphosphoric acid ester salt [Bmim] [DBP],
1-ethyl-3-methylimidazole ethyl-sulfate salt [Emim] [ES],
Diethanolamine villaumite [Hdea] [Cl]
Monoethanolamine acetate [Hmea] [Ac],
Diethanolamine acetate [Hdea] [Ac],
Triethanolamine acetate [Htea] [Ac]；
Described hydrophobic ionic liquid is selected from:
1-butyl-3-Methylimidazole. bis-trifluoromethylsulfoandimide salt [Bmim] [Tf2N], 1-alkyl-3-Methylimidazole. six
Fluorophosphate [Cnmim] [PF6],n=0,2,4,6,8,10。
Described in step (2) in monosaccharide aqueous solution, the mass concentration of monosaccharide is 50g/L～500g/L, further
Preferably monosaccharide mass concentration is 100g/L～400g/L, the over-saturation monosaccharide prepared under this preferred concentration
In ionic liquid, monosaccharide dissolubility in ionic liquid and stability of solution improve further.
By concentrating under reduced pressure except water so that the quality of water in over-saturation monosaccharide ionic liquid described in step (2)
Mark≤10%, more preferably≤2%.In over-saturation monosaccharide ionic liquid, too much moisture is unfavorable for C5 fat
The generation of fat acid monosaccharide ester, under the mass fraction of preferred water, the conversion ratio of C5 fatty acid monosaccharide ester is higher.
Described C5 fatty acid can be positive valeric acid, 2-Methyl Butyric Acid, 3 Methylbutanoic acid, 2-penetenoic acid, 3-amylene
Acid, 4-penetenoic acid, 2-methyl-3-butenoic acid, 2-methyl-2-butenoic acid, 2-ethyl-2-acrylic acid, 2,4-diamyl
One in olefin(e) acid.
Described monosaccharide can be glucose, fructose, galactose, mannose, ribose, deoxyribose, xylose,
One in arabinose.
In step (3), the addition of desiccant is relevant with the water-taking efficiency of desiccant, more preferably, described dry
Drying prescription can use 4A molecular sieve, and the addition quality of 4A molecular sieve can be the volume of described reaction system
5-15%。
Described lipase can be selected for commercialization or self-control lipase, and lipase state can be free or immobilization.
The microbe-derived of lipase is selected from Candida Antarctica(antarctic candida), Thermomyces
Lanuginosus aspergillus oryzae, Rhizomucor miehei rhizomucor miehei or Mucor miehei rice black wool are mould, relatively
Excellently, the immobilized enzyme using source to be antarctic candida, so that conversion ratio raises further.
Extraction described in step (4) is the extracting method that this area is conventional, such as can be molten by adding
Agent is extracted and is obtained C5 fatty acid monosaccharide ester, and described solvent can be ethyl acetate, the tert-butyl alcohol, ethanol etc., institute
State the purification process that purification is this area routine, such as, can be to be washed by silica gel column chromatography or macroporous resin adsorption
De-method, purification is so that the quality purity of C5 fatty acid monosaccharide ester is more than 95%.
The present invention also provides for C5 fatty acid monosaccharide ester prepared by the preparation method of a kind of any of the above-described embodiment at volume
Application in cigarette, by the described C5 fatty acid independent wiring solution-forming of monosaccharide ester or allocate in conventional tobacco spice with
The mode of perfuming or charging is sprayed in tobacco, based on the weight of tobacco, and described C5 fatty acid list
The addition weight of sugar ester is 0.0005%-0.05%, preferably, and the addition weight of described C5 fatty acid monosaccharide ester
For 0.001%-0.008%.Preferably, described C5 fatty acid monosaccharide ester is positive valeric acid glucose ester, 2-methyl
At least one in butanoic acid glucose ester and 3 Methylbutanoic acid glucose ester.
The present invention also provides for a kind of Medicated cigarette, and the preparation method being added with any of the above-described embodiment in described Medicated cigarette obtains
C5 fatty acid monosaccharide ester, the most preferably, described C5 fatty acid monosaccharide ester be positive valeric acid glucose ester,
At least one in 2-Methyl Butyric Acid glucose ester and 3 Methylbutanoic acid glucose ester.
With specific embodiment, the invention will be further described below.
Embodiment one
By 50mL hydrophilic ionic-liquid [Bmim] [TfO] and 50mL hydrophobic ionic liquid [Bmim] [Tf2N]
Mix homogeneously.400g/L D/W 50g is added in mixed ionic liquid.By glucose ion liquid
Body mixture concentrates the water content anhydrated to mixing liquid under 50 DEG C of rotating conditions of Rotary Evaporators and is less than
10%(mass fraction) (measuring with Karl_Fischer method), then by undissolved dextran particles and ionic liquid
Separating, collection of ions liquid level obtains over-saturation glucose ion liquid mixture.In 500ml tool plug triangular flask
Add above-mentioned glucose ion liquid, 3 Methylbutanoic acid 8.2g, Novozyme435(derive from Candida
Antarctica) 410U, 4A molecular sieve 10g, 40 DEG C of constant-temperature table reaction 20h, calculated by 3 Methylbutanoic acid,
Reaction conversion ratio is 82%.Add 500mL ethyl acetate to extract 3 times, collect ethyl acetate, decompression distillation
Go ethyl acetate, collect and obtain 18.4g mixture.By silicagel column on mixture with toluene: ethyl acetate: second
Alcohol: water=40:30:25:1 (V/V) is that eluant carries out eluting, obtains the 3 Methylbutanoic acid glucose of purification
Ester 4.2g.Collect reacted immobilized enzyme, after adding water and oxolane flushing, treat after 45 DEG C of vacuum drying
With.By the most identical method, carrying out second time with the enzyme reclaimed and react, conversion ratio 77%(presses 3-methyl
Butanoic acid meter), reaction conversion ratio is 72% for the third time.
Embodiment two
By 90mL hydrophilic ionic-liquid [Bmim] [TfO] and 10mL hydrophobic ionic liquid [Bmim] [Tf2N]
Mix homogeneously.500g/L D/W 40g is added in mixed ionic liquid.By glucose ion liquid
Body mixture concentrates the water content anhydrated to mixing liquid less than 2% under 50 DEG C of rotating conditions of Rotary Evaporators
(measuring with Karl_Fischer method), then separates undissolved dextran particles with ionic liquid, collection of ions
Liquid level obtains over-saturation glucose ion liquid mixture.Above-mentioned glucose is added in 500ml tool plug triangular flask
Ionic liquid, 3 Methylbutanoic acid 8.2g, Novozyme435(derive from Candida Antarctica) 410U,
4A molecular sieve 15g, 40 DEG C of constant-temperature table reaction 20h, calculated by 3 Methylbutanoic acid, and reaction conversion ratio is 80%.
Adding 500mL ethyl acetate to extract 3 times, collect ethyl acetate, decompression distillation is gone ethyl acetate, is collected
To 19.4g mixture.By silicagel column on mixture with toluene: ethyl acetate: ethanol: water=40:30:25:
1 (V/V) is that eluant carries out eluting, obtains the 3 Methylbutanoic acid glucose ester 4.1g of purification.Collect reacted
Immobilized enzyme, after adding water and oxolane flushing, stand-by after 45 DEG C of vacuum drying.By the most identical method,
Carrying out second time with the enzyme reclaimed to react, conversion ratio 42%(is based on 3 Methylbutanoic acid), third time reaction converts
Rate is 18%.
From embodiment two it can be seen that when hydrophilic ionic-liquid amount more than hydrophobic ionic liquid time, first
Secondary reaction conversion ratio can reach 80%, but enzyme is lived by such mixed ionic liquid, damage is relatively big, thus
When making to carry out second time, third time reaction with the enzyme reclaimed, conversion ratio is relatively low.
Embodiment three
By 10mL hydrophilic ionic-liquid [Bmim] [TfO] and 90mL hydrophobic ionic liquid [Bmim] [Tf2N]
Mix homogeneously.50g/L D/W 400g is added in mixed ionic liquid.By glucose ion liquid
Body mixture concentrates the water content anhydrated to mixing liquid less than 5% under 50 DEG C of rotating conditions of Rotary Evaporators
(measuring with Karl_Fischer method), then separates undissolved dextran particles with ionic liquid, collection of ions
Liquid level obtains over-saturation glucose ion liquid mixture.Above-mentioned glucose is added in 500ml tool plug triangular flask
Ionic liquid, 3 Methylbutanoic acid 8.2g, Novozyme435(derive from Candida Antarctica) 410U,
4A molecular sieve 10g, 40 DEG C of constant-temperature table reaction 20h, calculated by 3 Methylbutanoic acid, and reaction conversion ratio is 50%.
Adding 500mL ethyl acetate to extract 3 times, collect ethyl acetate, decompression distillation is gone ethyl acetate, is collected
To 14.4g mixture.By silicagel column on mixture with toluene: ethyl acetate: ethanol: water=40:30:25:
1 (V/V) is that eluant carries out eluting, obtains the 3 Methylbutanoic acid glucose ester 3.2g of purification.Collect reacted
Immobilized enzyme, after adding water and oxolane flushing, stand-by after 45 DEG C of vacuum drying.By the most identical method,
Carrying out second time with the enzyme reclaimed to react, conversion ratio 48%(is based on 3 Methylbutanoic acid), third time reaction converts
Rate is 47%.
Embodiment four
By 25mL hydrophilic ionic-liquid [Bmim] [TfO] and 75mL hydrophobic ionic liquid [Bmim] [Tf2N]
Mix homogeneously.400g/L D/W 50g is added in mixed ionic liquid.By glucose ion liquid
Body mixture concentrates the water content anhydrated to mixing liquid under 50 DEG C of rotating conditions of Rotary Evaporators and is less than
10%(measures with Karl_Fischer method), then undissolved dextran particles is separated with ionic liquid, collect
Ionic liquid layer obtains over-saturation glucose ion liquid mixture.Above-mentioned Portugal is added in 500ml tool plug triangular flask
Grape sugar ionic liquid, 3 Methylbutanoic acid 22g, Novozyme435(derive from Candida Antarctica) 410U,
4A molecular sieve 10g, 40 DEG C of constant-temperature table reaction 24h, calculated by 3 Methylbutanoic acid, and reaction conversion ratio is 85%.
Adding 500mL ethyl acetate to extract 3 times, collect ethyl acetate, decompression distillation is gone ethyl acetate, is collected
To 28.6g mixture.By silicagel column on mixture with toluene: ethyl acetate: ethanol: water=40:30:25:
1 (V/V) is that eluant carries out eluting, obtains the 3 Methylbutanoic acid glucose ester 6.9g of purification.Collect reacted
Immobilized enzyme, after adding water and oxolane flushing, stand-by after 45 DEG C of vacuum drying.By the most identical method,
Carrying out second time with the enzyme reclaimed to react, conversion ratio 81%(is based on 3 Methylbutanoic acid), third time reaction converts
Rate is 78%.
Embodiment five
Enzyme catalysis is carried out with Thermomyces lanuginosus source Lipase TLIM.With 2-Methyl Butyric Acid
Replace 3 Methylbutanoic acid by the reaction condition of embodiment one, add Lipase TLIM1000U 45 DEG C of reactions
Under the conditions of prepare 2-Methyl Butyric Acid glucose ester, conversion ratio (based on 2-Methyl Butyric Acid) is 58%.Add 500mL
The tert-butyl alcohol extracts 3 times, collects tert-butyl alcohol layer, and decompression distillation is removed the tert-butyl alcohol, collected and obtain 14.7g mixture.
By silicagel column in the method for embodiment one, mixture is carried out column chromatography be further purified, obtain the 2-methyl of purification
Butanoic acid glucose ester 3.3g.Reclaiming immobilized enzyme by the method for embodiment one, the enzyme of recovery carries out second time and reacts,
Conversion ratio 52%(is based on 2-Methyl Butyric Acid), reaction conversion ratio is 47% for the third time.
Embodiment six
By 50mL ionic liquid [Bmim] [TfO] and 50mL ionic liquid [Bmim] [Tf2N] mix homogeneously.
400g/L fructose water solution 50g is added in mixed ionic liquid.Fructose ionic liquid mixture is being rotated
Under 55 DEG C of rotating conditions of evaporimeter concentrate anhydrate to water content less than 2%(with Karl_Fischer method measure), then
Being separated with ionic liquid by undissolved fructose granule, collection of ions liquid level obtains over-saturation fructose ionic liquid and mixes
Compound.Above-mentioned fructose ionic liquid, positive valeric acid 22g, Novozyme is added in 500ml tool plug triangular flask
4351000U, 4A molecular sieve 15g, 50 DEG C of constant-temperature table reaction 20h, calculated by positive valeric acid, and conversion ratio is
62%.Adding 500mL ethyl acetate to extract 3 times, collect ethyl acetate, ethyl acetate is gone in decompression distillation,
Collection obtains 26.9g mixture.Mixture is carried out column chromatography by silicagel column in the method for embodiment one further
Purification, obtains the positive valeric acid fructose ester 7.8g of purification.
Embodiment seven
By 50mL ionic liquid [Bmim] [BF4] and 50mL ionic liquid [Bmim] [PF6] mix homogeneously.?
Mixed ionic liquid adds 400g/L fructose water solution 50g.Fructose ionic liquid mixture is being rotated steaming
Send out that concentrating under 55 DEG C of rotating conditions of instrument anhydrates to water content measures with Karl_Fischer method less than 2%(), then will
Undissolved fructose granule separates with ionic liquid, and collection of ions liquid level obtains the mixing of over-saturation fructose ionic liquid
Thing.500ml tool plug triangular flask in add above-mentioned fructose ionic liquid, 2,4-pentadienoic acid 22g, Novozyme
4351000U, 4A molecular sieve 15g, 50 DEG C of constant-temperature table reaction 20h, by 2,4-pentadienoic acid calculates, and turns
Rate is 58%.Adding 500mL ethyl acetate to extract 3 times, collect ethyl acetate, acetic acid is removed in decompression distillation
Ethyl ester, collects and obtains 25.8g mixture.Mixture is carried out column chromatography by silicagel column in the method for embodiment one
It is further purified, obtains the 2 of purification, 4-pentadienoic acid fructose ester 7.5g.
Embodiment eight
Embodiment one 3 Methylbutanoic acid glucose ester after purification is made into the ethanol that mass concentration is 0.5% molten
Liquid, uses cigarette automatic perfume adding machine to be uniformly injected into by 3 Methylbutanoic acid glucose ester solution to blank Medicated cigarette,
Based on cigarette quality, the addition of 3 Methylbutanoic acid glucose ester is 0.001%-0.008%(mass fraction).Will
The test Medicated cigarette of blank Medicated cigarette and sample-adding is positioned over relative humidity (60 ± 3) %, flat in the environment of temperature (22 ± 2) DEG C
Weighing apparatus more than 48h, is smoked panel test, with blank coil to 3 Methylbutanoic acid glucose ester perfuming Medicated cigarette by the group of smokeing panel test
Cigarette, as blank sample, evaluates different the cigarette sample aroma quality of perfuming amount, humectation, zest.Smoking result
As shown in the table.
3 Methylbutanoic acid glucose ester perfuming Medicated cigarette is smoked panel test table
| Consumption | Smoking result |
| Blank | Flue gas is coarse, and dried-up miscellaneous QI is heavier, and flue gas has dry sensation |
| 0.001% | The soft degree of flue gas slightly improves, and cigarette perfume (or spice) richness promotes, and dry sensation makes moderate progress |
| 0.003% | The soft degree of flue gas improves substantially, and cigarette perfume (or spice) enriches, and dry sensation improves substantially |
| 0.005% | The soft degree of flue gas improves substantially, and cigarette perfume (or spice) enriches, and dry sensation improves substantially |
| 0.008% | The soft degree of flue gas improves substantially, but slightly owes clear, and flue gas is sweet |
Above content is to combine concrete preferred implementation further description made for the present invention, it is impossible to
Assert the present invention be embodied as be confined to these explanations.For those skilled in the art
For, without departing from the inventive concept of the premise, it is also possible to make some equivalents and substitute or obvious modification, and
And performance or purposes identical, all should be considered as belonging to protection scope of the present invention.
Claims (2)
1. the preparation method of a C5 fatty acid monosaccharide ester, it is characterised in that comprise the steps:
(1) preparation mixed ionic liquid, in described mixed ionic liquid, hydrophilic ionic-liquid [Bmim] [TfO]
For 25mL, hydrophobic ionic liquid [Bmim] [Tf2N] it is 75mL；
(2) in described mixed ionic liquid, 400g/L D/W 50g mix homogeneously is added,
At 50 DEG C, concentrating under reduced pressure is except removing undissolved glucose after water, obtains over-saturation glucose ion liquid；
(3) in described over-saturation glucose ion liquid, add the 3 Methylbutanoic acid of 22g, 410U
The 4A molecular sieve of Novozyme 435 and 10g, reacts 24h, described under the reaction temperature of 40 DEG C
Under the catalysis of Novozyme 435, described 3 Methylbutanoic acid and glucose response generate 3 Methylbutanoic acid glucose
Ester；
(4) extract and 3 Methylbutanoic acid glucose ester described in purification.
2. preparation method as claimed in claim 1, it is characterised in that: over-saturation Portugal described in step (2)
Mass fraction≤10% of water in grape sugar ionic liquid.
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| CN103966022A (en) * | 2014-05-20 | 2014-08-06 | 河北中烟工业有限责任公司 | Mellow-sweet type spice for cigarettes |
| CN104593445B (en) * | 2015-01-21 | 2018-07-06 | 深圳大学 | A kind of synthetic method of sucrose fatty acid ester |
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| CN102423114A (en) * | 2011-07-25 | 2012-04-25 | 红塔烟草(集团)有限责任公司 | Low-tar cigarette aroma compensation method |
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