CN106854225A - A kind of preparation method and applications of glucose ester - Google Patents
A kind of preparation method and applications of glucose ester Download PDFInfo
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- CN106854225A CN106854225A CN201611154730.2A CN201611154730A CN106854225A CN 106854225 A CN106854225 A CN 106854225A CN 201611154730 A CN201611154730 A CN 201611154730A CN 106854225 A CN106854225 A CN 106854225A
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- preparation
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- dichloromethane
- glucose
- water
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims abstract description 62
- 239000008103 glucose Substances 0.000 title claims abstract description 62
- -1 glucose ester Chemical class 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 134
- 238000006243 chemical reaction Methods 0.000 claims abstract description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000000243 solution Substances 0.000 claims abstract description 54
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 42
- 229920001184 polypeptide Polymers 0.000 claims abstract description 37
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 37
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 37
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 13
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000005406 washing Methods 0.000 claims abstract description 8
- 239000012074 organic phase Substances 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 238000002156 mixing Methods 0.000 claims description 28
- 241000208125 Nicotiana Species 0.000 claims description 26
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 26
- 239000008346 aqueous phase Substances 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 22
- 230000004913 activation Effects 0.000 claims description 18
- 238000012544 monitoring process Methods 0.000 claims description 17
- 239000012071 phase Substances 0.000 claims description 14
- 239000000284 extract Substances 0.000 claims description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- 102400000069 Activation peptide Human genes 0.000 claims description 8
- 101800001401 Activation peptide Proteins 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001718 carbodiimides Chemical class 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 235000009508 confectionery Nutrition 0.000 claims 1
- 235000019504 cigarettes Nutrition 0.000 abstract description 19
- 239000002994 raw material Substances 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 8
- 239000003205 fragrance Substances 0.000 abstract description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003546 flue gas Substances 0.000 abstract description 5
- 239000007789 gas Substances 0.000 abstract description 3
- 239000002304 perfume Substances 0.000 abstract description 3
- 230000035807 sensation Effects 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 7
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 235000019615 sensations Nutrition 0.000 description 2
- 230000000391 smoking effect Effects 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention relates to a kind of preparation method and applications of glucose ester.The inventive method is with glucose and n-butyric acie as raw material, polypeptide condensing agent is catalyst, dichloromethane is solvent, reacted under conditions of 20 25 DEG C, reaction solution is washed through extraction, water washing, saturated sodium bicarbonate solution washing, the saturated common salt aqueous solution, dry, be concentrated under reduced pressure, conventional silica gel column chromatography purifying obtains colourless to flaxen oily liquids：N-butyric acie glucose ester sterling；The n-butyric acie glucose ester prepared using the present invention, is applied in cigarette shreds, harmony fragrance soft with flue gas exquisiteness with certain concentration, increases perfume quantity, reduces miscellaneous gas, increases strength and soft degree, reduces dry sensation, improves the effect of pleasant impression.
Description
【Technical field】
The invention belongs to essence spice for cigarette technical field.More particularly it relates to a kind of preparation method of glucose ester
And its application.
【Background technology】
Latent Studies of The Aromatic Substances refers to that itself is without fragrance or little to fragrant sensation, but can degrade or split in ageing or burning
Produced after solution and cause fragrant material, be called and do fragrance presoma.By the application of Studies of The Aromatic Substances of diving, can not only eliminate the effects of the act essence matter
The change of the unstable compound of amount so that essence not only smells fragrant comfortable harmony, and composition can be made to possess certain
Secrecy effect.The latent Studies of The Aromatic Substances stage that also place is evolving at present of the application on the perfuming of cigarette, and due to each state-owned
The reason for closing enterprise's secrecy, the preparation and application of cigarette flavor precursors are rarely reported.
Glucose ester is the important fragrance presoma of a class in tobacco.Sugar ester can realize the uniform release of fragrance, reduce
The usage amount of spices.Sugar ester has coordinates fragrance, increases perfume quantity, reduces miscellaneous gas, increases strength and soft degree, reduces drying
Sense, increases Hui Tian, improves the effect of pleasant impression, while also a certain degree of humectation effect.During cigarette burns and sucks, glucose
The ester group cleavage of connection discharges the carboxylic acid for having positive role to flue gas suction taste, and wherein low-grade carboxylic acid assigns flue gas suction taste fragrance spy
Levy, can make flue gas become fine and smooth, alcohol and, higher fatty acids acid obtains cigarette odor-absorbing then more by the pH value of regulation tobacco
To improvement.Preparation and the report of application at present both at home and abroad on sugar ester is little.Therefore, artificial synthesized sugar esters compounds are simultaneously
Being applied to has foreseeable prospect in the flavouring of tobacco.
The present invention has searched out good selectivity, high conversion rate, the syntheti c route of the glucose ester of low cost.And pass through
The route, corresponding glucose ester is prepared for by raw material of glucose and various carboxylic acids, and should with certain concentration by them
For in cigarette shreds.The present inventor completes the present invention finally on the basis for summarizing prior art by lot of experiments.
【The content of the invention】
[technical problem to be solved]
It is an object of the invention to provide a kind of preparation method and applications of glucose ester.
Technical scheme]
The present invention is achieved through the following technical solutions.
The present invention relates to a kind of preparation method and applications of glucose ester.
The step of preparation method, is as follows：
1st, a kind of preparation method and applications of glucose ester, it is characterised in that the preparation method and application the step of it is as follows：
Glucose, n-butyric acie, polypeptide condensing agent and dichloromethane are by weight 1:2~5：1~5：10~25, first by n-butyric acie
With polypeptide condensing agent admixture activation 1 hour, while dichloromethane is cooled into 20~25 DEG C, after glucose be added to be cooled to
In 20~25 DEG C of dichloromethane, the mixed liquor of the slow n-butyric acie being added dropwise after activation and polypeptide condensing agent after stirring 30min,
React temperature control after dripping to be reacted 8~12 hours at 20~25 DEG C, real-time monitoring in course of reaction；
Reaction solution is cooled to 10~15 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.3~0.7 water
Extract reaction of going out.The organic layer of lower floor is separated, the water on upper strata is mutually extracted with dichloromethane again, and the weight of water and dichloromethane compares 1:
0.2~0.5, merge organic phase, organic phase washed with water, saturated sodium bicarbonate solution washing, the washing of the saturated common salt aqueous solution are done
It is dry, it is concentrated under reduced pressure, silica gel column chromatography purifying obtains colourless to flaxen oily liquids：Glucose ester sterling；
2nd, according to another preferred embodiment of the invention, the polypeptide condensing agent for being used is carbodiimide class condensing agent, will
N-butyric acie and polypeptide condensing agent mixing are, for activated polypeptides condensing agent, and to add a small amount of activator in the reaction；
3rd, according to another preferred embodiment of the invention, reaction temperature control is at 20~25 DEG C, and wants real-time monitoring；
4th, according to another preferred embodiment of the invention, it is by volume 1 by the water phase on upper strata and dichloromethane:0.2~
0.5 uniform hybrid extraction, extracts 2~3 times in the same way；
5th, according to another preferred embodiment of the invention, first by organic phase and water according to volume ratio 1:0.5~1 is uniform mixed
Close, separate upper strata aqueous phase, washed 2~3 times according to the same manner；Again by organic phase and saturated sodium bicarbonate solution according to volume ratio 1:
0.5~1 uniform mixing, separates upper strata aqueous phase, and PH=7 is washed till according to the same manner；Finally by organic phase and the saturated common salt aqueous solution
According to volume ratio 1:0.5~1 uniform mixing, separates upper strata aqueous phase, is washed 2~3 times according to the same manner；
6th, according to another preferred embodiment of the invention, described drying is to add anhydrous sodium sulfate to stir 4 hours
Under the conditions of be dried；
7th, preparation method according to claim 1, it is described it is concentrated under reduced pressure be in 0.01~0.08MPa of pressure and 25~35
Concentrated under conditions of DEG C；
8th, according to another preferred embodiment of the invention, it is 200 ~ 300 mesh silica gel that silica gel column chromatography purifying uses filler, molten
Petroleum ether, n-hexane, ethyl acetate are selected in agent；
9th, according to another preferred embodiment of the invention, solution glucose ester and alcohols solvent being made into, by 0.001-
1% tobacco percentage by weight is sprayed onto on leaf group pipe tobacco；
10th, according to another preferred embodiment of the invention, described alcohols solvent is 95% ethanol or propane diols or glycerine；
The present invention is described in more detail below.
The present invention relates to a kind of preparation method and applications of glucose ester.
The step of preparation method, is as follows：
Glucose, n-butyric acie, polypeptide condensing agent and dichloromethane are by weight 1:2~5：1~5：10~25, after by n-butyric acie
With polypeptide condensing agent admixture activation 1 hour, while dichloromethane is cooled into 20~25 DEG C, it is cooled to glucose is added to
In 20~25 DEG C of dichloromethane, the mixed liquor of the slow n-butyric acie being added dropwise after activation and polypeptide condensing agent after stirring 30min,
React temperature control after dripping to be reacted 8~12 hours at 20~25 DEG C, real-time monitoring in course of reaction；
Reaction solution is cooled to 10~15 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.3~0.7 water
Extract reaction of going out.The organic layer of lower floor is separated, the water on upper strata is mutually extracted with dichloromethane again, and the weight of water and dichloromethane compares 1:
0.2~0.5, merge organic phase, organic phase washed with water, saturated sodium bicarbonate solution washing, the washing of the saturated common salt aqueous solution are done
It is dry, it is concentrated under reduced pressure, silica gel column chromatography purifying obtains colourless to flaxen oily liquids：N-butyric acie glucose ester sterling；
In the present invention, the polypeptide condensing agent for being used is carbodiimide class condensing agent such as DCC, EDCl, DIC etc., due to this kind of
Comparatively the activity of condensing agent almost will carry out activated polypeptides condensing agent, it is necessary to n-butyric acie and polypeptide condensing agent are mixed, and
And activator such as DMAP, HOBt etc. are generally needed to be added using such condensing agent, it is primarily due to the first stage institute of reaction
The intermediate of production is unstable,
If being converted into corresponding active ester without activator, easily itself is into urea.
In the present invention, reaction temperature control is at 20~25 DEG C, and wants real-time monitoring；Reaction temperature must be controlled in 20-25
Degree, temperature is slower less than this thermotonus speed, and it is low that temperature increases reaction selectivity higher than the impurity of this thermotonus.Instead
Real-time monitoring is wanted during answering, the time of strict control reaction, the reaction time, oversize impurity was accordingly increased, and yield declines.More
Preferably, reaction temperature control is in 20-25 degree, and the real-time monitoring raw material reaction extraction that adds water immediately completely is gone out reaction.
In the present invention, the water phase that will be separated is by volume 1 with dichloromethane:0.2~1 uniform hybrid extraction, by same
The method of sample is extracted 2~3 times；Dichloromethane is 1 with water volume ratio:0.2~1 be it is rational, preferably 1：0.2~0.8, more
Preferably 1：0.2~0.5.
In the present invention, first by organic phase and water according to volume ratio 1:0.5~1 uniform mixing, separates upper strata aqueous phase, according to
The same manner is washed 2~3 times, and reaction solution is 1 with water volume ratio：0.5~1 be it is rational, preferably 1：0.5~0.8, more preferably
Ground is 1：0.5~0.6.
Again by organic phase and saturated sodium bicarbonate solution according to volume ratio 1:0.5~1 uniform mixing, separates upper strata aqueous phase,
PH=7 is washed till according to the same manner；
Finally by organic phase and the saturated common salt aqueous solution according to volume ratio 1:0.5~1 uniform mixing, separates upper strata aqueous phase, according to
The same manner is washed 2~3 times；Reaction solution is 1 with saturated common salt aqueous solution volume ratio：0.5~1 be it is rational, preferably 1：0.5
~0.8, more preferably 1：0.5~0.6.
In the present invention, described drying is dried under conditions of adding anhydrous sodium sulfate to stir 4 hours.As nothing
Solid drier as aqueous sodium persulfate also has anhydrous magnesium sulfate, anhydrous calcium chloride etc., but their post processing relative to nothing
Difficulty is wanted for aqueous sodium persulfate a bit.Meanwhile, these solid driers typically have two kinds of occupation modes one during use
Plant is to stand 12~24 hours after adding；Another kind is to stir 3~5 hours after adding.Stirring is greatly shortened for comparing
Dry time, the corresponding deadline for shortening technique.And the organic solvent used in the present invention is dichloromethane
Alkane density ratio water is big, water layer on upper strata, therefore, stirring drying effect is more preferable.
It is furthermore preferred that described drying is dried under conditions of adding anhydrous sodium sulfate to stir 4 hours.
In the present invention, it is described it is concentrated under reduced pressure be in the condition that 0.01~0.08MPa of pressure and temperature are 25~35 DEG C
Under concentrated.Concentrated under reduced pressure is that the equipment for using is the equipment being commonly used in current organic synthesis field, such as：Rotary evaporation
Instrument, vacuum-concentrcted device.
In the present invention, the conventional silicon of the mesh silica gel of filler 200 ~ 300, solvent petroleum ether, n-hexane or ethyl acetate is used
It is gel column chromatography eluting；Because glucose ester is oily liquids, and boiling point conventional vacuum distillation and recrystallization very high are not
The purpose of purifying can be reached, therefore, purified using conventional silica gel column chromatography.
In the present invention, application of the glucose ester in cigarette shreds be：Glucose ester and alcohols solvent are pressed into 0.001-
1%（Tobacco quality percentage）Wiring solution-forming is after-applied onto cigarette shreds, and applying method is to be sprayed on leaf group pipe tobacco in air
In dry.0.001-1%（Tobacco quality percentage）Addition is rational, preferably 0.001-0.006%, more preferably
Ground is 0.001-0.003%.
In the present invention, described alcohols solvent is a kind of organic solvent for being selected from 95% ethanol or propane diols or glycerine.
Preferably, described organic solvent is 95% ethanol or propane diols.
It is highly preferred that described organic solvent is 95% ethanol.
The glucose ester prepared using the present invention, is applied in cigarette shreds with certain concentration, soft with flue gas exquisiteness
With harmony fragrance increases perfume quantity, reduces miscellaneous gas, increases strength and soft degree, reduces dry sensation, improves the effect of pleasant impression.
In the present invention, detected using mass spectrum of nuclear magnetic resonance analysis method and determined, what conventional silica gel column chromatography purifying was obtained
Product is n-butyric acie glucose ester.
Use instrument：Bruck-400M NMRs
Instrument condition determination：With deuterated dimethyl sulfoxide as solvent, tetramethylsilane is internal standard.
Testing result,1H-NMR(400MHz,DMSO-d6) δ:0.96 (m, 15H), 1.46 (m, 10H), 1.44 (m,
10H), 3.35 (m, 10H), 3.31 ~ 3.36 (d, 2H), 3.50 (m, 1H), 3.80 (m, 2H), 4.00 (m, 1H), 5.60 ~ 5.90
(m,1H)。
Beneficial effect]
The beneficial effects of the invention are as follows：The present invention has searched out good selectivity, high conversion rate, the glucose ester of low cost
Syntheti c route.And by the route, corresponding glucose ester is prepared for by raw material of glucose and various carboxylic acids, and by they
It is applied in cigarette shreds with certain concentration.
【Specific embodiment】
The present invention is will be better understood that by following embodiments.
Embodiment 1：
Glucose, n-butyric acie, polypeptide condensing agent and dichloromethane are by weight:1:3：5：15, first n-butyric acie and polypeptide are contracted
Mixture admixture activation 1 hour, while dichloromethane is cooled into 20 DEG C, after glucose is added to the dichloromethane for being cooled to 20 DEG C
In alkane, the mixing of the slow n-butyric acie and polypeptide condensing agent being added dropwise after activation after stirring 30min is reacted temperature control and is existed after dripping
20~25 DEG C are reacted 8 hours, and raw material just reacts complete after real-time monitoring finds to react 8 hours in course of reaction；
Reaction solution is cooled to 10 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.5 water extracts reaction of going out.
The organic layer of lower floor is separated, is by volume 1 by the water phase on upper strata and dichloromethane:0.5 uniform hybrid extraction, by same side
Method is extracted 3 times, merges organic phase, first by organic phase and water according to volume ratio 1:0.5 uniform mixing, separates upper strata aqueous phase, according to
The same manner is washed 3 times, then by organic phase and saturated sodium bicarbonate solution according to volume ratio 1:0.5 uniform mixing, separates upper water
Phase, PH=7 is washed till according to the same manner；Finally by organic phase and the saturated common salt aqueous solution according to volume ratio 1:0.5 uniform mixing,
Upper strata aqueous phase is separated, is washed 3 times according to the same manner；Anhydrous sodium sulfate is added in organic phase to be carried out under conditions of stirring 4 hours
Dry, concentrated under conditions of being 30 DEG C in pressure 0.01MPa and temperature, silica gel column chromatography purifying obtains colourless to flaxen oil
Shape liquid：N-butyric acie glucose ester sterling；
Embodiment 2：
Glucose, palmitic acid, polypeptide condensing agent and dichloromethane are by weight 1:2：3：20, after palmitic acid and polypeptide are condensed
Agent admixture activation 1 hour, while dichloromethane is cooled into 23 DEG C, glucose is being added to the dichloromethane that is cooled to 23 DEG C
In, the mixed liquor of the slow palmitic acid being added dropwise after activation and polypeptide condensing agent after stirring 30min reacts temperature control and exists after dripping
20~25 DEG C are reacted 10 hours, and raw material just reacts complete after real-time monitoring is reacted 10 hours in course of reaction；
Reaction solution is cooled to 12 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.3 water extracts reaction of going out.
The organic layer of lower floor is separated, is by volume 1 by the water phase on upper strata and dichloromethane:0.8 uniform hybrid extraction, by same side
Method is extracted 2 times, merges organic phase, first by organic phase and water according to volume ratio 1:0.7 uniform mixing, separates upper strata aqueous phase, according to
The same manner is washed 3 times, then by organic phase and saturated sodium bicarbonate solution according to volume ratio 1:0.7 uniform mixing, separates upper water
Phase, PH=7 is washed till according to the same manner；Finally by organic phase and the saturated common salt aqueous solution according to volume ratio 1:0.7 uniform mixing,
Upper strata aqueous phase is separated, is washed 2 times according to the same manner；Anhydrous sodium sulfate is added in organic phase to be carried out under conditions of stirring 4 hours
Dry；Concentrated under conditions of being 35 DEG C in pressure 0.02MPa and temperature；Silica gel column chromatography purifying obtains colourless to flaxen oil
Shape liquid：Palmitic acid glucose ester sterling；
Embodiment 3：
Glucose, isobutyric acid, polypeptide condensing agent and dichloromethane are by weight 1:1：1：18, first isobutyric acid and polypeptide are condensed
Agent admixture activation 1 hour, while dichloromethane is cooled into 22 DEG C, after glucose is added to the dichloromethane for being cooled to 22 DEG C
In, the mixed liquor of the slow isobutyric acid being added dropwise after activation and polypeptide condensing agent after stirring 30min reacts temperature control and exists after dripping
20~25 DEG C are reacted 12 hours, real-time monitoring in course of reaction, raw material after real-time monitoring finds to react 12 hours in course of reaction
Just react complete；
Reaction solution is cooled to 14 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.6 water extracts reaction of going out.
The organic layer of lower floor is separated, is by volume 1 by the water phase on upper strata and dichloromethane:0.7 uniform hybrid extraction, by same side
Method is extracted 3 times, merges organic phase, first by organic phase and water according to volume ratio 1:0.8 uniform mixing, separates upper strata aqueous phase, according to
The same manner is washed 2 times, then by organic phase and saturated sodium bicarbonate solution according to volume ratio 1:0.8 uniform mixing, separates upper water
Phase, PH=7 is washed till according to the same manner；Finally by organic phase and the saturated common salt aqueous solution according to volume ratio 1:0.8 uniform mixing,
Upper strata aqueous phase is separated, is washed 3 times according to the same manner；Anhydrous sodium sulfate is added in organic phase to be carried out under conditions of stirring 5 hours
Dry；Concentrated under conditions of being 25 DEG C in pressure 0.04MPa and temperature；Silica gel column chromatography purifying obtains colourless to flaxen oil
Shape liquid：Isobutyric acid glucose ester sterling；
Embodiment 4：
Glucose, benzoic acid, polypeptide condensing agent and dichloromethane are by weight 1:4：3：22, first benzoic acid and polypeptide are condensed
Agent admixture activation 1 hour, while dichloromethane is cooled into 25 DEG C, after glucose is added to the dichloromethane for being cooled to 25 DEG C
In, the mixed liquor of the slow benzoic acid being added dropwise after activation and polypeptide condensing agent after stirring 30min reacts temperature control and exists after dripping
20~25 DEG C are reacted 9 hours, real-time monitoring in course of reaction, and raw material is firm after real-time monitoring finds to react 9 hours in course of reaction
Good reaction is complete；
Reaction solution is cooled to 13 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.7 water extracts reaction of going out.
The organic layer of lower floor is separated, is by volume 1 by the water phase on upper strata and dichloromethane:1 uniform hybrid extraction, in the same way
Extraction 2 times, merges organic phase, first by organic phase and water according to volume ratio 1:0.9 uniform mixing, separates upper strata aqueous phase, according to same
Sample loading mode is washed 3 times, then by organic phase and saturated sodium bicarbonate solution according to volume ratio 1:0.9 uniform mixing, separates upper strata aqueous phase,
PH=7 is washed till according to the same manner；Finally by organic phase and the saturated common salt aqueous solution according to volume ratio 1:0.9 uniform mixing, separates
Upper strata aqueous phase, washes 2 times according to the same manner；Anhydrous sodium sulfate is added to be dried under conditions of stirring 3 hours in organic phase；
Concentrated under conditions of being 33 DEG C in pressure 0.07MPa and temperature；Silica gel column chromatography purifying obtains colourless to flaxen oily liquid
Body：Benzoic acid glucose ester sterling；
Embodiment 5：
Glucose, oleic acid, polypeptide condensing agent and dichloromethane are by weight 1:3：2：16, first oleic acid and polypeptide condensing agent are mixed
Close activation 1 hour, while dichloromethane is cooled into 24 DEG C, after glucose be added to be cooled in 24 DEG C of dichloromethane,
The mixed liquor of the slow oleic acid being added dropwise after activation and polypeptide condensing agent after stirring 30min, reacted after dripping temperature control 20~
25 DEG C react 11 hours, real-time monitoring in course of reaction, in course of reaction real-time monitoring find reaction 11 hours after raw material just
Reaction is complete；
Reaction solution is cooled to 15 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.4 water extracts reaction of going out.
The organic layer of lower floor is separated, is by volume 1 by the water phase on upper strata and dichloromethane:0.3 uniform hybrid extraction, by same side
Method is extracted 2 times, merges organic phase, first by organic phase and water according to volume ratio 1:1 uniform mixing, separates upper strata aqueous phase, according to same
Sample loading mode is washed 3 times, then by organic phase and saturated sodium bicarbonate solution according to volume ratio 1:1 uniform mixing, separates upper strata aqueous phase, presses
PH=7 is washed till according to the same manner；Finally by organic phase and the saturated common salt aqueous solution according to volume ratio 1:1 uniform mixing, separates upper strata
Water phase, washes 3 times according to the same manner；Anhydrous sodium sulfate is added to be dried under conditions of stirring 3 hours in organic phase；In pressure
Power 0.05MPa and temperature are concentration under conditions of 32 DEG C；Silica gel column chromatography purifying obtains colourless to flaxen oily liquids：Oil
Sour grapes sugar ester sterling；
Embodiment 6：
Glucose, phenylacetic acid, polypeptide condensing agent and dichloromethane are by weight 1:5：3：24, first phenylacetic acid and polypeptide are condensed
Agent admixture activation 1 hour, while dichloromethane is cooled into 23 DEG C, after glucose is added to the dichloromethane for being cooled to 23 DEG C
In, the mixed liquor of the slow phenylacetic acid being added dropwise after activation and polypeptide condensing agent after stirring 30min reacts temperature control and exists after dripping
20~25 DEG C are reacted 12 hours, real-time monitoring in course of reaction, raw material after real-time monitoring finds to react 12 hours in course of reaction
Just react complete；
Reaction solution is cooled to 10 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.5 water extracts reaction of going out.
The organic layer of lower floor is separated, is by volume 1 by the water phase on upper strata and dichloromethane:0.6 uniform hybrid extraction, by same side
Method is extracted 3 times, merges organic phase, first by organic phase and water according to volume ratio 1:0.6 uniform mixing, separates upper strata aqueous phase, according to
The same manner is washed 2 times, then by organic phase and saturated sodium bicarbonate solution according to volume ratio 1:0.6 uniform mixing, separates upper water
Phase, PH=7 is washed till according to the same manner；Finally by organic phase and the saturated common salt aqueous solution according to volume ratio 1:0.6 uniform mixing,
Upper strata aqueous phase is separated, is washed 2 times according to the same manner；Anhydrous sodium sulfate is added in organic phase to be carried out under conditions of stirring 5 hours
Dry；Concentrated under conditions of being 27 DEG C in pressure 0.03MPa and temperature；Silica gel column chromatography purifying obtains colourless to flaxen oil
Shape liquid：Phenylacetic acid glucose ester is pure；
Embodiment 7：
95% ethanol solution is uniformly sprayed on pipe tobacco, is dried in atmosphere, manual cigarette is smoked panel test.
Embodiment 8：
The glucose ester of above-mentioned preparation is dissolved in wiring solution-forming in 95% ethanol solution, with 0.001%（Tobacco quality percentage）
Addition, solution is uniformly sprayed on pipe tobacco, is dried in atmosphere, and manual cigarette is smoked panel test.
Embodiment 9：
The glucose ester of above-mentioned preparation is dissolved in wiring solution-forming in 95% ethanol solution, with 0.002%（Tobacco quality percentage）
Addition, solution is uniformly sprayed on pipe tobacco, is dried in atmosphere, and manual cigarette is smoked panel test.
Embodiment 10：
The glucose ester of above-mentioned preparation is dissolved in wiring solution-forming in 95% ethanol solution, with 0.003%（Tobacco quality percentage）
Addition, solution is uniformly sprayed on pipe tobacco, is dried in atmosphere, and manual cigarette is smoked panel test.
Embodiment 11：
The glucose ester of above-mentioned preparation is dissolved in wiring solution-forming in 95% ethanol solution, with 0.004%（Tobacco quality percentage）
Addition, solution is uniformly sprayed on pipe tobacco, is dried in atmosphere, and manual cigarette is smoked panel test.
Embodiment 12：
The glucose ester of above-mentioned preparation is dissolved in wiring solution-forming in 95% ethanol solution, with 0.005%（Tobacco quality percentage）
Addition, solution is uniformly sprayed on pipe tobacco, is dried in atmosphere, and manual cigarette is smoked panel test.
Embodiment 13：
The glucose ester of above-mentioned preparation is dissolved in wiring solution-forming in 95% ethanol solution, with 0.05%（Tobacco quality percentage）Add
Dosage, solution is uniformly sprayed on pipe tobacco, is dried in atmosphere, and manual cigarette is smoked panel test.
Embodiment 14：
The glucose ester of above-mentioned preparation is dissolved in wiring solution-forming in 95% ethanol solution, with 0.1%（Tobacco quality percentage）Add
Dosage, solution is uniformly sprayed on pipe tobacco, is dried in atmosphere, and manual cigarette is smoked panel test.
The smoking result of various sugar esters prepared by table 1
Remarks：Above glucose ester is all dissolved in wiring solution-forming in 95% ethanol solution, with 0.003%（Tobacco quality percentage）
Addition.
Table 2 probes into the smoking result of application by taking n-butyric acie glucose ester as an example
Claims (10)
1. a kind of preparation method and applications of glucose ester, it is characterised in that as follows the step of the preparation method and applications：
Glucose, n-butyric acie, polypeptide condensing agent and dichloromethane are by weight 1:2~5：1~5：10~25, first by n-butyric acie
With polypeptide condensing agent admixture activation 1 hour, while dichloromethane is cooled into 20~25 DEG C, after glucose be added to be cooled to
In 20~25 DEG C of dichloromethane, the mixed liquor of the slow n-butyric acie being added dropwise after activation and polypeptide condensing agent after stirring 30min,
React temperature control after dripping to be reacted 8~12 hours at 20~25 DEG C, real-time monitoring in course of reaction；
Reaction solution is cooled to 10~15 DEG C after reaction completely, it is 1 to be slowly added to reaction solution with water volume ratio:0.3~0.7 water
Extract reaction of going out, separate the organic layer of lower floor, the water on upper strata is mutually extracted with dichloromethane again, and the weight of water and dichloromethane compares 1:
0.2~0.5, merge organic phase, organic phase washed with water, saturated sodium bicarbonate solution washing, the washing of the saturated common salt aqueous solution are done
It is dry, it is concentrated under reduced pressure, silica gel column chromatography purifying obtains colourless to flaxen oily liquids：N-butyric acie glucose ester sterling.
2. preparation method according to claim 1, it is characterised in that the polypeptide condensing agent for being used is the contracting of carbodiimide class
Mixture, it is, for activated polypeptides condensing agent, and to add a small amount of work in the reaction that n-butyric acie and polypeptide condensing agent are mixed
Agent.
3. preparation method according to claim 1, it is characterised in that reaction temperature control will be supervised in real time at 20~25 DEG C
Survey.
4. preparation method according to claim 1, it is characterised in that be by volume by water phase and the dichloromethane on upper strata
1:0.2~0.5 uniform hybrid extraction, extracts 2~3 times in the same way.
5. preparation method according to claim 1, it is characterised in that first by organic phase and water according to volume ratio 1:0.5~1
Uniform mixing, separates upper strata aqueous phase, is washed 2~3 times according to the same manner；Again by organic phase and saturated sodium bicarbonate solution according to body
Product compares 1:0.5~1 uniform mixing, separates upper strata aqueous phase, and PH=7 is washed till according to the same manner；Finally by organic phase and saturated common salt
The aqueous solution is according to volume ratio 1:0.5~1 uniform mixing, separates upper strata aqueous phase, is washed 2~3 times according to the same manner.
6. preparation method according to claim 1, it is characterised in that described drying is to add anhydrous sodium sulfate stirring 4
It is dried under conditions of hour.
7. preparation method according to claim 1, it is characterised in that it is described it is concentrated under reduced pressure be pressure 0.01~
0.08MPa with 25~35 DEG C under conditions of concentrated.
8. preparation method according to claim 1, it is characterised in that it is 200 ~ 300 mesh that silica gel column chromatography purifying uses filler
Silica gel, solvent selects petroleum ether, n-hexane, ethyl acetate.
9. application according to claim 1, it is characterised in that the solution for being made into glucose ester and alcohols solvent, presses
0.001-1% tobacco percentage by weights are sprayed onto on leaf group pipe tobacco.
10. application according to claim 9, it is characterised in that described alcohols solvent is 95% ethanol or propane diols or sweet
Oil.
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Application publication date: 20170616 |