CN107793325A - A kind of new method for preparing synthetic capsaicin - Google Patents
A kind of new method for preparing synthetic capsaicin Download PDFInfo
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- CN107793325A CN107793325A CN201711106546.5A CN201711106546A CN107793325A CN 107793325 A CN107793325 A CN 107793325A CN 201711106546 A CN201711106546 A CN 201711106546A CN 107793325 A CN107793325 A CN 107793325A
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- toluene
- synthetic capsaicin
- vanillylamine
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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 present invention relates to a kind of new method for preparing synthetic capsaicin；This method is using Vanillylamine, pelargonic acid as raw material, using toluene as solvent, the dehydration under boric acid catalysis effect, prepares synthetic capsaicin；Vanillylamine, the mol ratio of pelargonic acid are 1：1；The mol ratio of Vanillylamine and boric acid is 1：0.05‑0.20；The dosage of toluene is to add 8 10 mL toluene per 1g Vanillylamines；The temperature of dehydration is 120 130 DEG C, the h of reaction time 8 10；This method is cooled to room temperature after also terminating including dehydration, adds water washing, after anhydrous sodium sulfate drying, toluene is recovered under reduced pressure using Rotary Evaporators, remaining liq stirred crystallization, obtains synthetic capsaicin.Present invention process is simple, cost is low, high income, reaction condition is low, product purity is high, green, solve the method for synthetic capsaicin in the prior art not environmentally, the problems such as yield is not high, post processing is complicated.
Description
Technical field
The present invention relates to a kind of new method for preparing synthetic capsaicin, more particularly, to use boric acid as catalyst preparation
The new method of synthetic capsaicin.
Background technology
Synthetic capsaicin (pelargonic acid vanilla acid amides Nonylic acid vanillyamid) is a kind of acid amides containing vanilla
Alkaloid, it is natural capsicum element analog, for white or light yellow solid, structural formula C17H27NO3, molecular weight 293.4, melt
56-58 DEG C of point.
Synthetic capsaicin serves many purposes；1st, police control is sudden and violent, and capsaicine has a strong impulse, meeting after human contact
Occur violent eye ache, shed tears, coughing, the symptom such as sneeze, pectoralgia.Its steam or micro mist have strong to eyes and the upper respiratory tract
Stimulation.And due to stimulus salve is low, symptom appearing and subsiding is fast, safety ratio is high, can be discharged with number of ways the features such as,
It is widely used in terms of police control is sudden and violent；2nd, there is the effect of a variety of efficacy of a drug：Such as analgesia, anti-inflammatory, frostbite is treated, be antipruritic, is killed
Bacterium, drug rehabilitation and wind-damp dispelling etc., clinically it is mainly used in treating the refractory diseases such as diabetic nerve pain, severe psoriasis；3、
It is used as nuisanceless pungent anti-fouling paint additive in marine paint production；4th, it is used as environment-friendly biology agriculture in agricultural production
Medicine；5th, be added to make in electric wire, cable, cable jacket termite-proof coating can prevent mouse, termite food erosion wound.
Synthetic capsaicin structural formula is：
The synthetic method of presently commercially available synthetic capsaicin mainly by Vanillylamine hydrochloride and positive pelargonyl chloride reaction prepare or
Person's Vanillylamine is prepared with the reaction of positive pelargonyl chloride, and both approaches are required for that first prepared by pelargonic acid and thionyl chloride reaction into positive nonyl
Acyl chlorides, the environmentally hazardous pernicious gas such as substantial amounts of hydrogen chloride, sulfur dioxide is generated, and yield is not high, due to neutralize
Hydrochloric acid in reaction, sodium chloride can be also generated during post processing, substantial amounts of waste water is generated again in order to remove sodium chloride,
These waste water are not disposable due to causing excitant very big containing a small amount of capsaicine, therefore existing synthetic capsaicin method
Post-process complicated and not environmentally friendly enough.
The content of the invention
The technical problems to be solved by the invention are that a kind of technique is simple, cost is low, high income, reaction condition are low, product
High, the green new method for preparing synthetic capsaicin of purity, to solve the method for synthetic capsaicin in the prior art not ring
Protect, yield is not high, post-processes the problems such as complicated.
To achieve these goals, the technical solution adopted in the present invention is：
A kind of new method for preparing synthetic capsaicin, be using Vanillylamine, pelargonic acid as raw material, using toluene as solvent,
The lower dehydration of boric acid catalysis effect, prepares synthetic capsaicin.
Vanillylamine, the mol ratio of pelargonic acid are 1：1.
The mol ratio of Vanillylamine and boric acid is 1：0.05-0.20.
The dosage of toluene is to add 8-10mL toluene per 1g Vanillylamines.
The temperature of dehydration is 120-130 DEG C, reaction time 8-10h.
Prepare the new method of synthetic capsaicin, in addition to dehydration terminate after be cooled to room temperature, add water washing, anhydrous sulphur
After sour sodium is dried, toluene is recovered under reduced pressure using Rotary Evaporators, remaining liq stirred crystallization, obtains synthetic capsaicin.
The new method for preparing synthetic capsaicin specifically includes following steps：Vanillylamine, pelargonic acid, toluene and boric acid are mixed
Close, be warming up to 120-130 DEG C under agitation, react 8-10h, reaction is cooled to room temperature after terminating, adds water washing, anhydrous sulphur
After sour sodium is dried, toluene is recovered under reduced pressure, remaining liq stirred crystallization, obtains synthetic capsaicin；
Vanillylamine, the mol ratio of pelargonic acid are 1：1；
The mol ratio of Vanillylamine and boric acid is 1：0.05-0.20；
The dosage of toluene is to add 8-10mL toluene per 1g Vanillylamines.
The volume of toluene being recovered under reduced pressure is that toluene adds the 2/3 of volume.
The temperature of stirred crystallization is -20 DEG C, time 3h.
The reaction equation of the present invention is as follows：
The beneficial effect of the present invention compared with prior art：
The present invention directly prepares synthetic capsaicin using catalyst boric acid catalysis Vanillylamine, pelargonic acid dehydration, without entering
(substantial amounts of hydrogen chloride, sulfur dioxide etc. can be generated using thionyl chloride etc. by, which so avoiding, endangers for the preparation of the positive pelargonyl chloride of row
The solvent of the pernicious gas of environment), and product and water are obtained after reacting, hydrogen chloride is not produced, post processing need not add
The alkaloids such as sodium hydroxide adjust pH numerical value, have prevented the possibility of a large amount of sodium chloride salts of generation, processing method is also relative
It is simple easy.
The present invention efficiently solves prior art increase environmental pressure, post-processes the problem of complicated, and significantly reduce life
Produce cost.Operating process of the present invention is simple, and reaction condition is gentle, and obtained synthetic capsaicin product, purity is good, steady quality,
It is suitable for industrialized production.After testing, for the synthetic capsaicin purity that the inventive method obtains up to more than 99%, yield is reachable
More than 87%.
Embodiment
The embodiment of the present invention is described in further detail with reference to embodiments.
Embodiment 1
In three mouthfuls of 500mL flasks, Vanillylamine 30.0g (0.196mol) is added, pelargonic acid 31.0g (0.196mol), is added
Enter toluene 300mL, boric acid 0.6g (9.8mmol), three-necked flask fills thermometer, a bite charge of oil separator+reflux condensation mode flatly
Oil water separator (is loaded reaction bulb, then reflux condensing tube is arranged on above oil water separator) by pipe, is closed flatly in addition,
Stirring to be opened, is warming up to 130 DEG C of reaction 8h, reaction is cooled to room temperature, adds 50mL water washings 2 times (extraction boric acid) after terminating,
After anhydrous sodium sulfate drying, toluene is recovered under reduced pressure at 60 DEG C using Rotary Evaporators, the toluene to distillation is the 2/ of original volume
3, stop being recovered under reduced pressure, remaining liq is transferred to cryogenic thermostat reactor, the stirred crystallization 3h under the conditions of -20 DEG C, and filtering, toluene is washed
Gained crystal is washed, drains to obtain white powder solid 50.3g, yield 87.4%, HPLC purity 99.1%.
White powder solid is analyzed：
Fourier's IR Characterization：IR(KBr,cm-1):3506(m),3446(w),3286(s),3062(w),2949(s),
2922(s),2848(s),1639(s),1544(s),1517(s),1429(m),1273(s),1031(m),850(m)。
NMR spectrum characterizes：1H NMR(CDCl3,T MS,400MHz)δ(ppm):6.87-6.75(m,3H,ArH),
5.67-5.65 (br+s, 2H, PhOH ,-CONH-), 4.35 (d, 2H, J=6Hz, PhCH2),3.88(s,3H,CH3O-),2.19
(t, 2H, J=7.6Hz ,-COCH2-),1.67-1.61(m,2H,-COCH2CH2-),1.33-1.26(m,10H),0.87(t,
3H, J=7 ,-CH2CH3)。
As a result prove, what the present invention was prepared is synthetic capsaicin.
Embodiment 2
In three mouthfuls of 500mL flasks, Vanillylamine 30.0g (0.196mol) is added, pelargonic acid 31.0g (0.196mol), is added
Enter toluene 300mL, boric acid 1.2g (19.6mmol), three-necked flask fills thermometer, a bite charge of oil separator+reflux condensation mode flatly
Pipe, close flatly in addition, open stirring, be warming up to 130 DEG C of reaction 8h, reaction is cooled to room temperature after terminating, add 50mL washings
Wash 2 times, after anhydrous sodium sulfate drying, toluene is recovered under reduced pressure at 60 DEG C using Rotary Evaporators, the toluene to distillation is substance
Long-pending 2/3, stopping being recovered under reduced pressure, remaining liq is transferred to cryogenic thermostat reactor, the stirred crystallization 3h under the conditions of -20 DEG C, filtering,
Toluene washing gained crystal, drains to obtain white powder solid (synthetic capsaicin) 48.0g, yield 83.4%, HPLC purity
98.7%.
Embodiment 3
In three mouthfuls of 500mL flasks, Vanillylamine 30.0g (0.196mol) is added, pelargonic acid 31.0g (0.196mol), is added
Enter toluene 240mL, boric acid 0.6g (9.8mmol), three-necked flask fills thermometer, a bite charge of oil separator+reflux condensation mode flatly
Pipe, close flatly in addition, open stirring, be warming up to 130 DEG C of reaction 8h, reaction is cooled to room temperature after terminating, add 50mL washings
Wash 2 times, after anhydrous sodium sulfate drying, toluene is recovered under reduced pressure at 60 DEG C using Rotary Evaporators, the toluene to distillation is substance
Long-pending 2/3, stopping being recovered under reduced pressure, remaining liq is transferred to cryogenic thermostat reactor, the stirred crystallization 3h under the conditions of -20 DEG C, filtering,
Toluene washing gained crystal, drains to obtain white powder solid (synthetic capsaicin) 46.8g, yield 81.5%, HPLC purity
98.5%.
Embodiment 4
In three mouthfuls of 500mL flasks, Vanillylamine 30.0g (0.196mol) is added, pelargonic acid 31.0g (0.196mol), is added
Enter toluene 240mL, boric acid 1.2g (19.6mmol), three-necked flask fills thermometer, a bite charge of oil separator+reflux condensation mode flatly
Pipe, close flatly in addition, open stirring, be warming up to 130 DEG C of reaction 8h, reaction is cooled to room temperature after terminating, add 50mL washings
Wash 2 times, after anhydrous sodium sulfate drying, toluene is recovered under reduced pressure at 60 DEG C using Rotary Evaporators, the toluene to distillation is substance
Long-pending 2/3, stopping being recovered under reduced pressure, remaining liq is transferred to cryogenic thermostat reactor, the stirred crystallization 3h under the conditions of -20 DEG C, filtering,
Toluene washs crystal, drains to obtain white powder solid (synthetic capsaicin) 45.9g, yield 79.8%, HPLC purity 98.3%.
Embodiment 5
In three mouthfuls of 500mL flasks, Vanillylamine 30.0g (0.196mol) is added, pelargonic acid 31.0g (0.196mol), is added
Enter toluene 240mL, boric acid 2.4g (39.2mmol), three-necked flask fills thermometer, a bite charge of oil separator+reflux condensation mode flatly
Pipe, close flatly in addition, open stirring, be warming up to 120 DEG C of reaction 10h, reaction is cooled to room temperature after terminating, add 50mL washings
Wash 2 times, after anhydrous sodium sulfate drying, toluene is recovered under reduced pressure at 60 DEG C using Rotary Evaporators, the toluene to distillation is substance
Long-pending 2/3, stopping being recovered under reduced pressure, remaining liq is transferred to cryogenic thermostat reactor, the stirred crystallization 3h under the conditions of -20 DEG C, filtering,
Toluene washs crystal, drains to obtain white powder solid (synthetic capsaicin) 44.2g, yield 76.9%, HPLC purity 98.2%.
Claims (9)
1. a kind of new method for preparing synthetic capsaicin, it is characterised in that be using Vanillylamine, pelargonic acid as raw material, with toluene
For solvent, the dehydration under boric acid catalysis effect, synthetic capsaicin is prepared.
2. the new method according to claim 1 for preparing synthetic capsaicin, it is characterised in that described Vanillylamine, just
The mol ratio of n-nonanoic acid is 1：1.
3. the new method according to claim 1 for preparing synthetic capsaicin, it is characterised in that described Vanillylamine and boron
The mol ratio of acid is 1：0.05-0.20.
4. the new method according to claim 1 for preparing synthetic capsaicin, it is characterised in that the dosage of described toluene is
Add 8-10 mL toluene per 1g Vanillylamines.
5. the new method according to claim 1 for preparing synthetic capsaicin, it is characterised in that the temperature of described dehydration
Spend for 120-130 DEG C, reaction time 8-10 h.
6. according to the new method for preparing synthetic capsaicin described in claim any one of 1-5, it is characterised in that also include dehydration
Reaction is cooled to room temperature after terminating, and adds water washing, and after anhydrous sodium sulfate drying, toluene is recovered under reduced pressure using Rotary Evaporators, remains
Extraction raffinate body stirred crystallization, obtains synthetic capsaicin.
7. the new method according to claim 6 for preparing synthetic capsaicin, it is characterised in that specifically include following steps：
Vanillylamine, pelargonic acid, toluene and boric acid are mixed, are warming up to 120-130 DEG C under agitation, reacts 8-10 h, reaction
Room temperature is cooled to after end, adds water washing, after anhydrous sodium sulfate drying, toluene is recovered under reduced pressure, remaining liq stirred crystallization, obtains
Synthetic capsaicin；
Described Vanillylamine, the mol ratio of pelargonic acid are 1：1；
Described Vanillylamine and the mol ratio of boric acid are 1：0.05-0.20；
The dosage of described toluene is to add 8-10 mL toluene per 1g Vanillylamines.
8. the new method according to claim 7 for preparing synthetic capsaicin, it is characterised in that the described first being recovered under reduced pressure
Benzene volume is that toluene adds the 2/3 of volume.
9. the new method according to claim 7 for preparing synthetic capsaicin, it is characterised in that the temperature of described stirred crystallization
Spend for -20 DEG C, time 3h.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109651222A (en) * | 2018-12-21 | 2019-04-19 | 上海昊航化工有限公司 | A kind of process for catalytic synthesis of Aniracetam |
| CN110305031A (en) * | 2019-07-03 | 2019-10-08 | 刘晓珍 | The preparation method of capsaicine and the capsaicine being prepared using this method |
| CN111875514A (en) * | 2020-08-24 | 2020-11-03 | 辽宁雷泰生物科技有限公司 | Method for preparing n-nonanoic vanilloylamine |
| CN112608247A (en) * | 2020-12-15 | 2021-04-06 | 遂宁晶安科技有限公司 | Preparation method of capsaicin and capsaicin prepared by using same |
| CN113024398A (en) * | 2021-03-15 | 2021-06-25 | 遂宁晶安科技有限公司 | Preparation method of capsaicin and capsaicin prepared by using same |
| CN113307759A (en) * | 2021-05-08 | 2021-08-27 | 青岛科技大学 | Cyanine near-infrared fluorescent probe and preparation method and application thereof |
| CN115160175A (en) * | 2022-07-13 | 2022-10-11 | 遂宁晶安科技有限公司 | Preparation method of capsaicin salt |
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| CN101155776A (en) * | 2005-04-07 | 2008-04-02 | 新日本理化株式会社 | Process for producing tricarboxylic acid tris(alkyl-substituted cyclohexylamide) |
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| CARLOS PALO-NIETO等: "Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis", 《ACS CATAL.》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109651222A (en) * | 2018-12-21 | 2019-04-19 | 上海昊航化工有限公司 | A kind of process for catalytic synthesis of Aniracetam |
| CN110305031A (en) * | 2019-07-03 | 2019-10-08 | 刘晓珍 | The preparation method of capsaicine and the capsaicine being prepared using this method |
| CN111875514A (en) * | 2020-08-24 | 2020-11-03 | 辽宁雷泰生物科技有限公司 | Method for preparing n-nonanoic vanilloylamine |
| CN112608247A (en) * | 2020-12-15 | 2021-04-06 | 遂宁晶安科技有限公司 | Preparation method of capsaicin and capsaicin prepared by using same |
| CN113024398A (en) * | 2021-03-15 | 2021-06-25 | 遂宁晶安科技有限公司 | Preparation method of capsaicin and capsaicin prepared by using same |
| CN113024398B (en) * | 2021-03-15 | 2023-12-19 | 遂宁晶安科技有限公司 | Preparation method of capsaicin and capsaicin prepared by using same |
| CN113307759A (en) * | 2021-05-08 | 2021-08-27 | 青岛科技大学 | Cyanine near-infrared fluorescent probe and preparation method and application thereof |
| CN115160175A (en) * | 2022-07-13 | 2022-10-11 | 遂宁晶安科技有限公司 | Preparation method of capsaicin salt |
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