CN105859572A - New synthesis method of capsaicin - Google Patents
New synthesis method of capsaicin Download PDFInfo
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- CN105859572A CN105859572A CN201610273708.3A CN201610273708A CN105859572A CN 105859572 A CN105859572 A CN 105859572A CN 201610273708 A CN201610273708 A CN 201610273708A CN 105859572 A CN105859572 A CN 105859572A
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- capsaicin
- crystallization
- novel synthesis
- dichloromethane
- synthesis
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- C—CHEMISTRY; METALLURGY
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
Abstract
The invention belongs to the field of organic synthesis, and particularly relates to a new synthesis method of capsaicin. The synthesis method comprises the following steps: by using vanillylamine hydrochloride and pelargonyl chloride as raw materials and a mixed solution of low-toxicity dichloromethane and water as a solvent, heating to react to obtain a crude product, and cooling for crystallization and purification, thereby obtaining the solid synthetic capsaicin. The method is simple to operate, has high controllability, can implement synthesis only by using a conventional reactor, and thus, can easily implement industrial production. The dichloromethane used as the solvent has lower toxicity than benzene, methylbenzene and other organic solvents, and thus, has lower hazards for workers in production. Brine wastewater and organic waste liquor generated in the production process can be recycled, so the whole technique has the advantages of zero discharge of waste liquor and no environment pollution. Sodium bicarbonate is adopted to remove the hydrochloric acid component in the raw materials and enhance the reaction temperature to 38-45 DEG C; and the method has the advantages of higher synthesis speed and higher yield (up to 90% or above). The cooling crystallization process is adopted to purify the product, so that the purity of the obtained capsaicin can reach 99% or above.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to the novel synthesis of a kind of capsaicin.
Background technology
Synthetic capsaicin, has another name called N-vanillin base-n-pelargonamide, or Vanillyl pelargonic amide.
Molecular formula is C17H27NO3；
Structural formula:
Purity: >=99% (HPLC)；
Outward appearance: white or pale yellow powder；
Fusing point: 56～58 DEG C；
Along with the numerous effect of synthetic capsaicin is the most recognized, compared to the extraction of natural capsicum element,
Its cost performance exceeds much, and therefore, it is applied the fields such as Biological control, health care, military affairs
To paying attention to the most widely.
Biological control: research shows that the repellent of murine with capsaicin as main component is to farm storage bandicoot
Having good repellent effect, the repellant repellent effect containing l% capsaicin keeps more than 5 months.
Protection cable and optical cable: the zest of capsaicin can produce repellent action to animal, for cable, light
Cable industry raised path between farm fields is as the functional additive of rodent-resistant cable sheathed plastic；In the plastics such as PVC, PE with
Prevent mouse, Coptotermes formosanus Shtrari. from the food of product is lost injury.Develop the micro-glue of the compositions based on capsaicin
Capsule ant-proof mouse-proof repellent, its strong acid can make the oral mucosa of murine and olfactory nerves be subject to
Detest and reject to intense stimulus to chew and cut, can hit again simultaneously and kill Coptotermes formosanus Shtrari., be a kind of novel-section with dual-use function
Material.Through the use for many years of Chinese big-and-middle-sized cable manufacturing enterprise, have confirmed that product have nontoxic, efficient,
Lasting premium properties.This product is used for buried cable, is possible to prevent the erosion of the insecticides such as Coptotermes formosanus Shtrari., and makees
With persistently.
Antifouling paint: in the process of moving, some algae, shellfish and software are often adhered in bottom to boats and ships
The marine organisms such as animal, these halobiontic attachments not only affect the speed of vessel motion, also can be to ship
Body causes certain infringement.Solution before is to use poisonous Organotin antifouling paints alow,
This coating in action while also water body is caused pollution.And utilize the repellent characteristics system of capsaicin
The biological anti-fouling paint become.It is applied to the part of boats and ships and marine structure and contact with sea water, can effectively prevent
Halobiontic attachment and aquatile are in the gathering of shell.Capsaicin instead of organotin conduct at present
Novel ship antifouling paint, is applied to boats and ships and marine structure antifouling field mouth.
Biological pesticide: capsaicin can have good touching as novel green pesticide in field of biological pesticide
Kill, repellent action, crop pest preventing and treating be can reach that drug effect is high, holding effect length and degradable feature, is
Novel environment-friendly biological pesticide.Capsaicin and goods thereof were just defined as by EPA as far back as 1991
Biochemical pesticide, and exempt it in water fruits and vegetables and corn, remain quantitative limitation.
Medical treatment: capsaicin application in terms of health care is just being recognized by people and is being gradually available for clinic
In the middle of practice.Capsaicin is fresh to neuropathic pain, rheumatic arthritis, Corii Bovis seu Bubali, psoriasis, acne,
Bald etc. have significant curative effect.Wherein analgesia is the application that the research of current capsaicin is the most ripe, Fructus Capsici
The analgesic activity of element is equal to morphine, but its analgesia time is 30～40 times of morphine.Fructus Capsici rope also may be used
Applying in terms of preventing and treating cardiovascular and cerebrovascular disease, capsaicin has the work adjusting blood fat to utilize rat test to show
With.This has great meaning to prevention cardiovascular disease and other diseases relevant with lipid oxidation.And it is peppery
The research in terms of anti-curing oncoma of the green pepper element is also a current hot topic, and most document shows that Fructus Capsici rope has very
Good function of tumor inhibition, also there are some researches show that Fructus Capsici rigging has anticancer and carcinogenic double effects, as anti-
Cancer and which aspect carcinogenic account for mastery reaction and also need to study further.Disappear additionally, capsaicin can also be prevented and treated
Peptic-ulcer and respiratory tract disease, and there is fat-reducing, resisting fatigue and the special efficacy of aiding drug rehabilitation.
Beauty treatment: capsaicin contributes to relaxing smooth muscle, causes cutaneous vasodilation, improves microcirculation, rises
To crease-resistant, improve the beautification function of the colour of skin and skin quality.Thus can as produce cosmetics and skincare product raw material,
For face, the improvement of arm part skin quality, but different parts is it is noted that the difference of concentration.
Military: capsaicin has good lacrimation, can cause the physiological reaction that human body is strong, make
People produce cough, vomit, the symptom, even disorientation such as shed tears, but have no side effect, therefore in army
To manufacture tear bombnoun, tear-gas rifle and the primary raw material of defensive weapon in thing, the U.S., Japan, Germany with
And the country such as Southeast Asia all has been widely used.Capsaicin is also used for individual's weapons for self-defense and uniform is disobeyed simultaneously
The instrument of method person.
Food additive: pungent, as one of basic five tastes, is peculiar wind indispensable in numerous food product
Taste.Extremely important effect is had in foodstuff flavouring.The pungent of appropriateness can increase appetite, facilitating digestion.
The people according to the different regions hobby to pungent, has formed four big local flavors: spicy, fragrant peppery, fresh peppery and sour
Peppery.Traditional chilli products such as processing technology such as Fructus Capsici sauce, Fructus Capsici powder, chilli oil is simple but has pungent
Not enough, easily go mouldy, preserve the shortcoming difficult, utilization rate of active components is low；And make with capsaicin sterling
Disadvantage mentioned above can be overcome for food pungent additive, have easy to use, be prone to preserve and control etc. is excellent
Point, can be used for the processing of various pungent foods in food industry.Including various pungent fatty foods, daily
Flavoring agent, pungent sauce, baked goods etc..Additionally, capsaicin has stronger antibacterial, sterilization idiocratic,
Antibacterial, fungi and yeasts are all had certain inhibitory action, can be as potential food preservative.
The bacteriostasis of capsaicin is by weak being by force: antibacterial > yeast > mycete, and become in wider temperature and pH
Good bacteriostatic activity can be kept in the range of change.
Summary of the invention
The technical problem to be solved is to provide the novel synthesis of a kind of capsaicin, overcomes existing
The deficiencies such as present in synthetic method synthetic method capsaicin purity complicated, synthesis is relatively low.
The technical scheme is that the novel synthesis of a kind of capsaicin,
It is characterized in that, step is as follows:
(1) preparation of crude product mixed liquor: by Vanillylamine hydrochlorate adds by sodium bicarbonate, two
Chloromethanes and water composition mixture in, described Vanillylamine hydrochlorate, sodium bicarbonate, dichloromethane and
The amount ratio of water is 1g:1-3g:4-6mL:4-8mL, after being sufficiently stirred for, at room temperature continues to described mixed
Dripping the dichloromethane solution of pelargonyl chloride in compound, 1-2h dropping is complete, and the quality of the pelargonyl chloride of instillation is
1-1.5 times of described Vanillylamine hydrochlorate quality, after dropping, is warming up to 38～45 DEG C and maintains
This thermotonus 1～2 hours, obtain crude product mixed liquor；
(2) crystallization and purification: described crude product mixed liquor is cooled to room temperature, successively it is carried out inorganic
Pickling stratification, inorganic alkali cleaning stratification, washing stratification, after washing, separatory retains organic
Phase, is evaporated off q. s. methylene chloride and obtains concentrating organic facies, after adding appropriate petroleum ether in concentration organic facies
Carrying out decrease temperature crystalline, crystallization final temperature controls ,-10～-20 DEG C, after crystallization terminates, to terminate temperature in crystallization
Degree is lower to be filtered, and washs, is dried, obtains solid synthetic capsaicin.Wherein, wash, being dried generally can be
Carry out under room temperature.
Based on the above method, the present invention can also have and embodies further below or optimize.
Concrete, in step (1), the dichloromethane solution union acyl chlorides of pelargonyl chloride and dichloromethane are according to 1:
1-1.2 volume ratio mix.
Preferably, the volume of the dichloromethane being evaporated off in step (2) accounts for the 1/5～1/3 of organic facies cumulative volume.
Preferably, the volume of the petroleum ether added in step (2) is concentrate organic facies cumulative volume 1.2～2
Times.
Concrete, the hydrochloric acid that mineral acid is mass fraction 15-37% of inorganic pickling use in step (2)
Or mass fraction is the sulphuric acid of 35-50%.
Concrete, the hydrogen-oxygen that inorganic base is mass fraction 10-30% of inorganic alkali cleaning use in step (2)
Change sodium solution.
Preferably, when inorganic pickling in step (2), inorganic alkali cleaning and washing, the consumption of cleaning mixture is respectively
For treating wash liq long-pending 1/10～1/5.
Preferably, described in step (2), the cooling rate of decrease temperature crystalline is 0.15-0.25 DEG C/min.
Preferably, be down to crystallize after final temperature, maintain the time of crystallization final temperature at more than 30min,
Filter under crystallization final temperature.
Compared with prior art, the invention have the benefit that
(1) one-step synthesis method, simple to operate, controllability is strong, and reaction condition is gentle, only needs to use
Popular response device can complete synthesis, it is easy to industrialized production；
(2) with dichloromethane as flux, raw material pelargonyl chloride and product capsaicin dissolubility wherein are good,
Ensureing that reaction can be smoothed out and be favorably improved yield, its toxicity is organic compared to benzene, toluene etc. molten
Agent is little, and during production, the harm to workman is little, and the brine waste that production process produces can follow with organic liquid waste
Ring uses, whole process waste liquor zero-emission, environmentally safe.
(3) sodium bicarbonate is selected to remove the salt acid constituents in raw material and promote reaction temperature to 38-45 DEG C,
Aggregate velocity faster, yield higher, can reach more than 90%.
(4) use decrease temperature crystalline method product is purified, the pure rate of the capsaicin obtained up to
To more than 99%.
Detailed description of the invention
Being described in more detail the present invention below in conjunction with specific embodiment, example is served only for explaining
The present invention, is not intended to limit the scope of the present invention.
Method used in the present invention, if no special requirements, is conventional method, used herein
Reagent, if no special requirements, be commercially available prod.
Embodiment 1
(1) preparation of crude product mixed liquor: will add by 140g carbon in 105g Vanillylamine hydrochlorate
In the mixture of acid hydrogen sodium, 600mL dichloromethane and 800mL water composition, after being sufficiently stirred for, in room
Temperature is lower continues the dropping dichloromethane solution (two containing 105g (110.4mL) pelargonyl chloride in described mixture
The volume of chloromethanes is 110.4mL), 1h dropping is complete, after dropping, is warming up to 38 DEG C and maintains
This thermotonus 2 hours, obtains crude product mixed liquor (about 1680mL)；
(2) crystallization and purification: described crude product mixed liquor is cooled to room temperature, first by 200mL 37%
Hydrochloric acid solution vibration washing and stratification, separatory obtains organic facies (about 800mL), uses 200mL 30%
Sodium hydroxide solution vibration wash above-mentioned organic facies stratification, separatory again organic facies (about
800mL), using 200mL to wash stratification, after washing, separatory retains organic facies (about 800mL),
260mL dichloromethane is evaporated off obtain concentrating organic facies (about 540mL), adds to concentrating in organic facies
Carrying out decrease temperature crystalline after 648mL petroleum ether, rate of temperature fall is 0.15 DEG C/min, and crystallization final temperature is about
-20 DEG C, maintain crystallization final temperature at least 30min, filter under crystallization final temperature, washing afterwards,
Being dried, obtain solid synthetic capsaicin 147.4g, yield is 90.8%, through efficient liquid phase chromatographic analysis
(HPLC) measuring its purity is 99.3%.
Embodiment 2
(1) preparation of crude product mixed liquor: will add by 200g carbon in 105g Vanillylamine hydrochlorate
In the mixture of acid hydrogen sodium, 500mL dichloromethane and 600mL water composition, after being sufficiently stirred for, in room
Temperature is lower continues the dropping dichloromethane solution (two containing 116 (122.0mL) pelargonyl chloride in described mixture
The volume of chloromethanes is 146.4mL), 1h dropping is complete, after dropping, is warming up to 42 DEG C and maintains
This thermotonus 1.5 hours, obtains crude product mixed liquor (1420mL)；
(2) crystallization and purification: described crude product mixed liquor is cooled to room temperature, first by 200mL 25%
Hydrochloric acid solution vibration washing and stratification, separatory obtains organic facies (about 750mL), uses 150mL 20%
Sodium hydroxide solution vibration wash above-mentioned organic facies stratification, separatory again organic facies (about
750mL), using 200mL to wash stratification, after washing, separatory retains organic facies (about 750mL),
150mL dichloromethane is evaporated off obtain concentrating organic facies (about 600mL), adds to concentrating in organic facies
Carrying out decrease temperature crystalline after 1080mL petroleum ether, rate of temperature fall is 0.25 DEG C/min, and crystallization final temperature is about
For-10 DEG C, maintain crystallization final temperature at least 30min, filter under crystallization final temperature, washing afterwards,
Being dried, obtain solid synthetic capsaicin 148.6g, yield is 91.5%, through efficient liquid phase chromatographic analysis
(HPLC) measuring its purity is 99.5%.
Embodiment 3
(1) preparation of crude product mixed liquor: will add by 300g carbon in 105g Vanillylamine hydrochlorate
In the mixture of acid hydrogen sodium, 400mL dichloromethane and 500mL water composition, after being sufficiently stirred for, in room
Temperature is lower continues the dropping dichloromethane solution containing 157.5g (165.6mL) pelargonyl chloride in described mixture
(volume of dichloromethane is 165.6mL), 1h dropping is complete, after dropping, is warming up to 45 DEG C also
Maintain this thermotonus 1 hour, obtain crude product mixed liquor (1300mL)；
(2) crystallization and purification: described crude product mixed liquor is cooled to room temperature, first by 200mL 15%
Hydrochloric acid solution vibration washing and stratification, separatory obtains organic facies (about 750mL), uses 200mL 10%
Sodium hydroxide solution vibration wash above-mentioned organic facies stratification, separatory again organic facies (about
750mL), using 200mL to wash stratification, after washing, separatory retains organic facies (about 750mL),
250mL dichloromethane is evaporated off obtain concentrating organic facies (about 500mL), adds to concentrating in organic facies
Carrying out decrease temperature crystalline after 600mL petroleum ether, rate of temperature fall is 0.21 DEG C/min, and crystallization final temperature is about
-15 DEG C, maintain crystallization final temperature at least 30min, filter under crystallization final temperature, washing afterwards,
Being dried, obtain solid synthetic capsaicin 146.4g, yield is 90.1%, through efficient liquid phase chromatographic analysis
(HPLC) measuring its purity is 99.2%.
Comparative example
(1) preparation of crude product mixed liquor: will add by 140g carbon in 105g Vanillylamine hydrochlorate
In the mixture of acid hydrogen sodium, 600mL dichloromethane and 800mL water composition, after being sufficiently stirred for, in room
Temperature is lower continues the dropping dichloromethane solution (two containing 105g (110.4mL) pelargonyl chloride in described mixture
The volume of chloromethanes is 110.4mL), 1h dropping is complete, after dropping, is warming up to 38 DEG C and maintains
This thermotonus 1 hour, obtains crude product mixed liquor (1680mL)；
(2) decompression distilation: wash above-mentioned crude product with soft water (1800mL × 5) the most neutral, subtract
Pressure distillation is removed solvent (vapor (steam) temperature 21 DEG C, pressure-0.1MPa) and is crystallized afterwards and be dried, it is thus achieved that solid
Synthetic capsaicin 141.2g, yield is 86.9%, measures its purity through efficient liquid phase chromatographic analysis (HPLC)
It is 92%.
From embodiment 1 to 3, the novel synthesis of the capsaicin of present invention offer is used to carry out Fructus Capsici
Element synthesis yield is all more than 90%, and purity can reach more than 99%.By comparative example and the number of embodiment 1
According to contrast it is recognized that while synthesis step is identical, but owing to the difference of method of purification causes productivity and pure
The difference of degree, reduce pressure in comparative example distilation, does not uses decrease temperature crystalline, but disposable concentrated by rotary evaporation
Crystallizing, it makes more impurity together crystallize out, causes purity to decline, and additionally its washing process uses
A large amount of water liquid repeatedly wash, and easily take away target product, cause yield to reduce.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all in the present invention
Spirit and principle within, any modification, equivalent substitution and improvement etc. made, should be included in this
Within bright protection domain.
Claims (10)
1. the novel synthesis of a capsaicin, it is characterised in that step is as follows:
(1) preparation of crude product mixed liquor: Vanillylamine hydrochlorate is added by sodium bicarbonate, dichloro
In the mixture of methane and water composition, described Vanillylamine hydrochlorate, sodium bicarbonate, dichloromethane and water
Amount ratio be 1g:1-3g:4-6mL:4-8mL, after being sufficiently stirred for, at room temperature continue to described mixing
Dripping the dichloromethane solution of pelargonyl chloride in thing, 1-2h dropping is complete, and the quality of the pelargonyl chloride of instillation is institute
State Vanillylamine hydrochlorate quality 1-1.5 times, after dropping, is warming up to 38～45 DEG C and maintenance should
Thermotonus 1～2 hours, obtain crude product mixed liquor；
(2) crystallization and purification: described crude product mixed liquor is cooled to room temperature, successively it is carried out inorganic
Pickling stratification, inorganic alkali cleaning stratification, washing stratification, after washing, separatory retains organic
Phase, is evaporated off q. s. methylene chloride and obtains concentrating organic facies, after adding appropriate petroleum ether in concentration organic facies
Carrying out decrease temperature crystalline, crystallization final temperature controls ,-10～-20 DEG C, after crystallization terminates, to terminate temperature in crystallization
Degree is lower to be filtered, and is washed out, is dried, obtains solid synthetic capsaicin.
The novel synthesis of a kind of capsaicin the most according to claim 1, it is characterised in that step
(1) in, the dichloromethane solution union acyl chlorides of pelargonyl chloride and dichloromethane are according to the volume ratio of 1:1-1.2
Mix.
The novel synthesis of a kind of capsaicin the most according to claim 1, it is characterised in that step
(2) volume of the dichloromethane being evaporated off in accounts for the 1/5～1/3 of organic facies cumulative volume.
The novel synthesis of a kind of capsaicin the most according to claim 1, it is characterised in that step
(2) volume of the petroleum ether added in is concentrate organic facies cumulative volume 1.2～2 times.
The novel synthesis of a kind of capsaicin the most according to claim 1, it is characterised in that step
(2) hydrochloric acid that mineral acid is mass fraction 15-37% or mass fraction that in, inorganic pickling uses are
The sulphuric acid of 35-50%.
The novel synthesis of a kind of capsaicin the most according to claim 1, it is characterised in that step
(2) sodium hydroxide solution that inorganic base is mass fraction 10-30% that in, inorganic alkali cleaning uses.
The novel synthesis of a kind of capsaicin the most according to claim 1, it is characterised in that step
(2) when inorganic pickling in, inorganic alkali cleaning and washing, the consumption of cleaning mixture respectively treats what wash liq amassed
1/9～1/4.
The novel synthesis of a kind of capsaicin the most according to claim 1, it is characterised in that will step
Suddenly the aqueous phase obtained after washing separatory in (2) is evaporated crystallization, obtains sodium salt solid and condensed water,
Condensed water can recycle in step (1).
9. according to the novel synthesis of a kind of capsaicin described in any one of claim 1 to 8, its feature
Being, described in step (2), the cooling rate of decrease temperature crystalline is 0.15-0.25 DEG C/min.
The novel synthesis of a kind of capsaicin the most according to claim 9, it is characterised in that step
Suddenly (2) are down to crystallize after final temperature, maintain the time of crystallization final temperature at more than 30min,
Filter under crystallization final temperature.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107173433A (en) * | 2017-07-04 | 2017-09-19 | 苏州农业职业技术学院 | A kind of fruit antistaling agent containing capsaicine |
| 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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| 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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Application publication date: 20160817 |