CN105646266A - Method for synthesizing N-vanillylnonanamide - Google Patents
Method for synthesizing N-vanillylnonanamide Download PDFInfo
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- CN105646266A CN105646266A CN201610075394.6A CN201610075394A CN105646266A CN 105646266 A CN105646266 A CN 105646266A CN 201610075394 A CN201610075394 A CN 201610075394A CN 105646266 A CN105646266 A CN 105646266A
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- aqueous solution
- pelargonic amide
- vanillyl pelargonic
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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Abstract
The invention discloses a method for synthesizing N-vanillylnonanamide. The method for synthesizing the N-vanillylnonanamide is characterized by including the following steps that vanillylamine hydrochloride is taken and dissolved in water, an organic phase solvent and nonanoyl chloride are added, then an alkaline aqueous solution is added to regulate the pH to 7.5-8.5, stirring reaction is performed at the temperature of 15-30 DEG C, standing for layering is performed after the full reaction is completed, and the N-vanillylnonanamide is separated out after organic phase distillation, wherein the organic phase solvent is prepared from, by weight, one or combination 1 of isopropyl acetate and ethyl acetate and 0.2-1.4 parts of N-hexane. The one-time synthetic yield of the method for synthesizing the N-vanillylnonanamide can be up to 97% or above, the purity of the product can be up to 95% or above, and recrystallization for purification is not needed.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to a kind of method synthesizing n-Vanillyl pelargonic amide.
Background technology
Pungency component in Fructus Capsici is a kind of mixture, and wherein the most pungent composition is capsaicin, and chemical name is n-Vanillyl pelargonic amide, as shown in Equation 1, molecular weight is 293.4 to its molecular formula, and fusing point is 56 ~ 58 DEG C, decomposition temperature is 340 DEG C, and water solublity is 27ppm when 25 DEG C. The capsaicin application in fields such as biological medicine, pesticide and functional paints is very extensive. In medicine, capsaicin can as the composition of the treatment medicine such as rheumatic arthritis, neuralgia, and owing to it has effect antibacterial, antiinflammatory, it can be additionally used in department of dermatologry clinic. Additionally, capsaicin can as the primary raw material of the main component of novel biopesticide and nuisanceless antifouling paint peculiar to vessel, it may also be used for prevent the food erosion injury of worm, Mus in the plastics such as polyethylene, polrvinyl chloride.
Formula 1
In prior art, capsaicin extracts mostly from natural capsicum, and production cost is higher. And, the method of current published synthetic capsaicin (n-Vanillyl pelargonic amide), there is the shortcomings such as severe reaction conditions, by-product is many, complex process, energy consumption are big, the most important thing is, the n-Vanillyl pelargonic amide purity that existing synthetic method prepares is all relatively low, it is necessary to by recrystallization so that product to be purified, therefore, add processing step, and introduce consumption and the recovery problem of organic solvent.
Summary of the invention
The technical problem to be solved in the present invention is that the n-Vanillyl pelargonic amide purity that existing artificial synthesis prepares is relatively low.
In order to solve above-mentioned technical problem, the invention discloses a kind of method synthesizing n-Vanillyl pelargonic amide, comprise the steps:
Taking Vanillylamine hydrochlorate soluble in water, add organic phase solvent and pelargonyl chloride, adding alkaline aqueous solution adjustment pH is 7.5 ~ 8.5, (it is preferably 18 ~ 30 DEG C) at 15 ~ 30 DEG C, stirring reaction, stratification after reacting completely, organic facies isolates n-Vanillyl pelargonic amide after distillation;
Wherein, described organic phase solvent is made up of the solvent of following parts by weight:
One of them or its combination 1 of isopropyl acetate or ethyl acetate;
Normal hexane 0.2 ~ 1.4.
Preferably, described organic phase solvent is made up of the solvent of following parts by weight:
One of them or its combination 1 of isopropyl acetate or ethyl acetate;
Normal hexane 0.2 ~ 0.4.
Preferably, described organic phase solvent is isopropyl acetate is the mixture of 1:0.2 ~ 0.4 with normal hexane weight ratio.
Preferably, described alkaline aqueous solution is the aqueous solution that potassium carbonate and potassium ethoxide are dissolved in water, and in aqueous solution, the weight of potassium ethoxide is the 6.0% ~ 14.0% of potassium carbonate and potassium ethoxide gross weight.
Preferably, reaction temperature is 23-25 DEG C.
Preferably, regulating pH is 8.0.
Preferably, the weight ratio of Vanillylamine hydrochlorate, organic phase solvent and pelargonyl chloride is 100:100 ~ 300:90 ~ 110.
Preferably, organic facies isolates n-Vanillyl pelargonic amide after decompression distillation, and the vacuum of decompression distillation is 0.1MPa.
Preferably, pelargonyl chloride and alkaline aqueous solution all add in the way of dropping.
The present invention can reach following effect:
1, the present invention adopts the method at the interfacial condensation of aqueous phase-organic facies to prepare n-Vanillyl pelargonic amide, organic phase solution used reclaims reusable completely, alkaline solution is neutralized by the hydrochloric acid generated in course of reaction, technique is simply discharged without any harmful gas or waste liquid, and whole process is in room temperature scope, equipment requirements is relatively low, be conducive to environmental protection and reduce cost and investment reduction.
2, the method synthesizing n-Vanillyl pelargonic amide of the present invention, single sintering yield is up to more than 97%, and the purity of product is up to more than 95%, does not need recrystallization to purify.
Detailed description of the invention
Below in conjunction with specific embodiment, the invention will be further described, so that those skilled in the art can be better understood from the present invention and can be practiced, but illustrated embodiment is not as a limitation of the invention.
The method of the n-Vanillyl pelargonic amide of synthesis provided by the invention, comprises the steps:
Taking Vanillylamine hydrochlorate soluble in water, add organic phase solvent and pelargonyl chloride, adding alkaline aqueous solution adjustment pH is 7.5 ~ 8.5, at 15 ~ 30 DEG C, and stirring reaction, stratification after reacting completely, organic facies isolates n-Vanillyl pelargonic amide after distillation;
Wherein, described organic phase solvent is made up of the solvent of following parts by weight:
One of them or its combination 1 of isopropyl acetate or ethyl acetate;
Normal hexane 0.2 ~ 1.4.
Reaction equation is as follows:
The present invention adopts the method at the interfacial condensation of aqueous phase-organic facies to prepare n-Vanillyl pelargonic amide, wherein organic facies selects one of them or its combination of isopropyl acetate or ethyl acetate and the mixture of normal hexane, wherein one of them or its of isopropyl acetate or ethyl acetate is combined as the good solvent of solvable n-Vanillyl pelargonic amide, it promotes that the forward of reaction carries out, normal hexane is the non-benign solvent of soluble n-Vanillyl pelargonic amide, product can be purified by it while reaction, with the purity of this conversion ratio that can ensure reaction and product.
It is exemplified below specific embodiment to illustrate:
Embodiment 1
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 150g organic phase solvent (isopropyl acetate 120g, normal hexane 30g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 8.0 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, room temperature it is cooled to after discharging, strong stirring obtains the n-Vanillyl pelargonic amide white crystals of 154.7g for 10 minutes, product purity is 99.2%, yield is 99.2%.
Embodiment 2
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 240g organic phase solvent (isopropyl acetate 200g, normal hexane 40g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 8.0 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, room temperature it is cooled to after discharging, strong stirring obtains the n-Vanillyl pelargonic amide white crystals of 155.8g for 10 minutes, product purity is 98.1%, yield is 98.8%.
Embodiment 3
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 280g organic phase solvent (isopropyl acetate 200g, normal hexane 80g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 8.0 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, room temperature it is cooled to after discharging, strong stirring obtains the n-Vanillyl pelargonic amide white crystals of 154.4g for 10 minutes, product purity is 98.2%, yield is 98.0%.
Embodiment 4
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 240g organic phase solvent (isopropyl acetate 100g, normal hexane 140g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 8.0 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, room temperature it is cooled to after discharging, strong stirring obtains the n-Vanillyl pelargonic amide white crystals of 156.3g for 10 minutes, product purity is 96.5%, yield is 97.5%.
Embodiment 5
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 240g organic phase solvent (isopropyl acetate 180g, normal hexane 60g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 110g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 8.2 that alkaline aqueous solution regulates pH after adding, after dropwising, at 24 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 20 DEG C it are cooled to after discharging, white crystals 156.8g is obtained through strong agitation, it is n-Vanillyl pelargonic amide, product purity is 97.4% after measured, yield is 98.7%.
Embodiment 6
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 150g organic phase solvent (isopropyl acetate 120g, normal hexane 30g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 0.68wt%, namely the weight of potassium ethoxide is the 6.4% of potassium carbonate and potassium ethoxide gross weight), it is 8.0 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 15 DEG C it are cooled to after discharging, after strong agitation 10min, obtain n-Vanillyl pelargonic amide white crystals 155.8g, product purity is 98.9% after measured, yield is 99.6%.
Embodiment 7
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 150g organic phase solvent (isopropyl acetate 120g, normal hexane 30g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.75wt%, namely the weight of potassium ethoxide is the 14.9% of potassium carbonate and potassium ethoxide gross weight), it is 8.3 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 18 DEG C it are cooled to after discharging, n-Vanillyl pelargonic amide white crystals 154.56g is obtained through strong agitation, product purity is 98.1%, yield is 98.0%.
Embodiment 8
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 180g organic phase solvent (isopropyl acetate 100g, normal hexane 80g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 105g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 5wt%, namely the weight of potassium ethoxide is the 33.3% of potassium carbonate and potassium ethoxide gross weight), it is 8.5 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 22 DEG C it are cooled to after discharging, n-Vanillyl pelargonic amide 160.1g is obtained through strong agitation, after measured, yield is 98.5%, product purity is 95.2%.
Embodiment 9
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 280g organic phase solvent (ethyl acetate 200g, normal hexane 80g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 90g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 8.0 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 15 DEG C it are cooled to after discharging, obtain n-Vanillyl pelargonic amide white crystals 158.8g through strong agitation and be n-Vanillyl pelargonic amide, yield is 98.22%, product purity is 95.7% after measured.
Embodiment 10
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 240g organic phase solvent (ethyl acetate 100g, normal hexane 140g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 7.9 that alkaline aqueous solution regulates pH after adding, after dropwising, at 23 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 15 DEG C it are cooled to after discharging, n-Vanillyl pelargonic amide white crystals 158.8g is obtained through strong agitation, product purity is 96.0% after measured, yield is 98.5%.
Embodiment 11
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 150g organic phase solvent (ethyl acetate 120g, normal hexane 30g), after stirring 30min, (potassium carbonate is dissolved in the aqueous solution of water to be slowly added dropwise 105g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%), it is 8.5 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 22 DEG C it are cooled to after discharging, n-Vanillyl pelargonic amide 157.7g is obtained through strong agitation, after measured, product purity is 94.9%, yield is 96.7%.
Embodiment 12
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 300g organic phase solvent (ethyl acetate 240g, normal hexane 60g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 7.5 that alkaline aqueous solution regulates pH after adding, after dropwising, at 15 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 22 DEG C it are cooled to after discharging, n-Vanillyl pelargonic amide 156.0g is obtained through strong agitation, after measured, yield is 96.8%, product purity is 96%.
Embodiment 13
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 100g organic phase solvent (ethyl acetate 80g, normal hexane 20g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 7.5 that alkaline aqueous solution regulates pH after adding, after dropwising, at 15 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 25 DEG C it are cooled to after discharging, n-Vanillyl pelargonic amide 156.0g is obtained through strong agitation, yield is 97.1%, product purity is 96.3%.
Embodiment 14
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add 150g organic phase solvent (ethyl acetate 60g, isopropyl acetate 60g, normal hexane 30g), after stirring 30min, (potassium carbonate and potassium ethoxide are dissolved in the aqueous solution of water to be slowly added dropwise 104g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%, the concentration of potassium ethoxide is 1.1wt%, namely the weight of potassium ethoxide is the 10% of potassium carbonate and potassium ethoxide gross weight), it is 8.0 that alkaline aqueous solution regulates pH after adding, after dropwising, at 24 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 20 DEG C it are cooled to after discharging, white crystals 156.6g is obtained through strong agitation, it is n-Vanillyl pelargonic amide, product purity is 97.5% after measured, yield is 98.7%.
Comparative example 1
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add ethyl acetate 150g, after stirring 30min, (potassium carbonate is dissolved in the aqueous solution of water to be slowly added dropwise 105g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%), it is 8.5 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 15 DEG C it are cooled to after discharging, n-Vanillyl pelargonic amide white crystals 159.8g is obtained through strong agitation, product purity is 87.2% after measured, yield is 90.1%.
Comparative example 2
By 100g Vanillylamine hydrochlorate with 350g water dissolution, add organic phase solvent 250g(isopropyl acetate 100g, normal hexane 150g), after stirring 30min, (potassium carbonate is dissolved in the aqueous solution of water to be slowly added dropwise 105g pelargonyl chloride and alkaline aqueous solution, in aqueous solution, the concentration of potassium carbonate is 10wt%), it is 8.5 that alkaline aqueous solution regulates pH after adding, after dropwising, at 25 DEG C, react 2 ~ 4 hours, stratification, take upper strata oily solution, decompression distillation under 0.1MPa, obtain slightly yellow transparency liquid, 15 DEG C it are cooled to after discharging, n-Vanillyl pelargonic amide white crystals 153.9g is obtained through strong agitation, product purity is 93.5% after measured, yield is 93.0%.
Embodiment described above is only the preferred embodiment lifted for absolutely proving the present invention, and protection scope of the present invention is not limited to this. Equivalent replacement that those skilled in the art make on basis of the present invention or conversion, all within protection scope of the present invention. Protection scope of the present invention is as the criterion with claims.
Claims (9)
1. the method synthesizing n-Vanillyl pelargonic amide, it is characterised in that comprise the steps:
Taking Vanillylamine hydrochlorate soluble in water, add organic phase solvent and pelargonyl chloride, adding alkaline aqueous solution adjustment pH is 7.5 ~ 8.5, at 15 ~ 30 DEG C, and stirring reaction, stratification after reacting completely, organic facies isolates n-Vanillyl pelargonic amide after distillation;
Wherein, described organic phase solvent is made up of the solvent of following parts by weight:
One of them or its combination 1 of isopropyl acetate or ethyl acetate;
Normal hexane 0.2 ~ 1.4.
2. the method for the n-Vanillyl pelargonic amide of synthesis according to claim 1, it is characterised in that described organic phase solvent is made up of the solvent of following parts by weight:
One of them or its combination 1 of isopropyl acetate or ethyl acetate;
Normal hexane 0.2 ~ 0.4.
3. the method for the n-Vanillyl pelargonic amide of synthesis according to claim 2, it is characterised in that described organic phase solvent is isopropyl acetate is the mixture of 1:0.2 ~ 0.4 with normal hexane weight ratio.
4. the method for the n-Vanillyl pelargonic amide of synthesis according to claim 1, it is characterized in that, described alkaline aqueous solution is the aqueous solution that potassium carbonate and potassium ethoxide are dissolved in water, and in aqueous solution, the weight of potassium ethoxide is the 6.0% ~ 14.0% of potassium carbonate and potassium ethoxide gross weight.
5. the method for the n-Vanillyl pelargonic amide of synthesis according to claim 1, it is characterised in that reaction temperature is 23-25 DEG C.
6. the method for the n-Vanillyl pelargonic amide of synthesis according to claim 1, it is characterised in that regulating pH is 8.0.
7. the method for the n-Vanillyl pelargonic amide of synthesis according to claim 1, it is characterised in that the weight ratio of Vanillylamine hydrochlorate, organic phase solvent and pelargonyl chloride is 100:100 ~ 300:90 ~ 110.
8. the method for the n-Vanillyl pelargonic amide of synthesis according to claim 1, it is characterised in that organic facies isolates n-Vanillyl pelargonic amide after decompression distillation, and the vacuum of decompression distillation is 0.1MPa.
9. the method for the n-Vanillyl pelargonic amide of synthesis according to claim 1, it is characterised in that pelargonyl chloride and alkaline aqueous solution all add in the way of dropping.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113105354A (en) * | 2021-03-05 | 2021-07-13 | 河南省化工研究所有限责任公司 | Novel method for preparing N- (4-hydroxy-3-methoxybenzyl) nonanamine without catalyst |
| CN115160175A (en) * | 2022-07-13 | 2022-10-11 | 遂宁晶安科技有限公司 | Preparation method of capsaicin salt |
| CN116003276A (en) * | 2022-12-22 | 2023-04-25 | 上海化学试剂研究所有限公司 | Method for synthesizing capsaicin by utilizing micro-reaction chip |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2168976A (en) * | 1984-12-20 | 1986-07-02 | Procter & Gamble | Amides and compositions thereof having anti-inflammatory activity |
| JPH069308A (en) * | 1992-06-19 | 1994-01-18 | Nippon Kayaku Co Ltd | Production of synthetic capsaicin and its microcapsule agent in the same reactor |
| RU2072985C1 (en) * | 1992-07-28 | 1997-02-10 | Государственный научно-исследовательский институт "Кристалл" | Method of synthesis of pelargonic acid vanilyl amide |
| CN1526699A (en) * | 2003-09-22 | 2004-09-08 | 朱松年 | Synthesis of n-nonanoic vanilloylamine |
| CN1982287A (en) * | 2005-12-14 | 2007-06-20 | 上海工程技术大学 | Capsicine synthesis |
| CN103288665A (en) * | 2013-06-27 | 2013-09-11 | 上海化学试剂研究所有限公司 | Preparation method of capsaicine |
-
2016
- 2016-02-03 CN CN201610075394.6A patent/CN105646266A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2168976A (en) * | 1984-12-20 | 1986-07-02 | Procter & Gamble | Amides and compositions thereof having anti-inflammatory activity |
| JPH069308A (en) * | 1992-06-19 | 1994-01-18 | Nippon Kayaku Co Ltd | Production of synthetic capsaicin and its microcapsule agent in the same reactor |
| RU2072985C1 (en) * | 1992-07-28 | 1997-02-10 | Государственный научно-исследовательский институт "Кристалл" | Method of synthesis of pelargonic acid vanilyl amide |
| CN1526699A (en) * | 2003-09-22 | 2004-09-08 | 朱松年 | Synthesis of n-nonanoic vanilloylamine |
| CN1982287A (en) * | 2005-12-14 | 2007-06-20 | 上海工程技术大学 | Capsicine synthesis |
| CN103288665A (en) * | 2013-06-27 | 2013-09-11 | 上海化学试剂研究所有限公司 | Preparation method of capsaicine |
Non-Patent Citations (2)
| Title |
|---|
| 袁余斌 等: "辣椒素正壬酸香草酰胺的合成", 《武汉工程大学学报》 * |
| 陈思浩，赵伟: "合成辣素的制备与应用", 《农药》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113105354A (en) * | 2021-03-05 | 2021-07-13 | 河南省化工研究所有限责任公司 | Novel method for preparing N- (4-hydroxy-3-methoxybenzyl) nonanamine without catalyst |
| CN113105354B (en) * | 2021-03-05 | 2023-07-21 | 河南省化工研究所有限责任公司 | Method for preparing N- (4-hydroxy-3-methoxybenzyl) nonanamide without catalyst |
| CN115160175A (en) * | 2022-07-13 | 2022-10-11 | 遂宁晶安科技有限公司 | Preparation method of capsaicin salt |
| CN116003276A (en) * | 2022-12-22 | 2023-04-25 | 上海化学试剂研究所有限公司 | Method for synthesizing capsaicin by utilizing micro-reaction chip |
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