CN108084000A - A kind of preparation method of isovanillin - Google Patents
A kind of preparation method of isovanillin Download PDFInfo
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- CN108084000A CN108084000A CN201711442415.4A CN201711442415A CN108084000A CN 108084000 A CN108084000 A CN 108084000A CN 201711442415 A CN201711442415 A CN 201711442415A CN 108084000 A CN108084000 A CN 108084000A
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
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Abstract
The present invention provides a kind of preparation method of isovanillin, belongs to the production technical field of isovanillin.The preparation method of isovanillin, includes the following steps：4~8h is reacted in the alkaline environment that dimethyl suflfate is 5~40 DEG C with Ethyl vanillin solution in temperature, filtering takes filter residue to obtain intermediate.Intermediate and the concentrated sulfuric acid react 2~7h under atmosphere of inert gases that temperature is 40~70 DEG C, condition of negative pressure.This preparation method is easy to get using raw materials, raw materials such as Ethyl vanillin, dimethyl suflfate and the concentrated sulfuric acids, and at low cost, process control is simple, easy to operate, easily forms industrialized production, yield is high, and wastewater flow rate is few, beneficial to environmental protection.
Description
Technical field
The present invention relates to the production technical field of isovanillin, in particular to a kind of preparation method of isovanillin.
Background technology
Isovanillin is also referred to as different 4-hydroxyl-3-methoxylbenxaldehyde or isovanillin, chemical name 3- hydroxyls -4-methoxybenzaldehyde.Isovanillin has
There are olive sample fragrance and strong milk, be a kind of important raw material in food additives industry, as fumet and sweetener,
It should be in sugaring, ice lolly, beverage, sweets and cigarette alcohol industry by extensive use.One kind in isovanillin or fine chemical industry
Staple product is widely used in coordinate plant growth, as additive of cosmetics and skin care products etc..There are one isovanillin tools
Unique property：With the variation of environment temperature, its fragrance also changes, and is therefore particularly suitable for some particular perfumes, essence
Industry, while also act as the smelly aromatizing agent of dispelling of the products such as soap, toothpaste and rubber, plastics.
Isovanillin has active hydroxyl and aldehyde radical, is synthesis various active drug, organic polymer acetal resin, answers
Miscellaneous natural products, such as coumarin derivatives, alkaloid, flavanones, the important intermediate of heterocyclic active compound.In recent years
Constantly there is report of the domestic and international scientific research institutions using isovanillin synthesis medicine intermediate.Isovanillin is synthesis the second states of PDE4
The important module and synthesis antidepressants rolipram of inhibitor and renin inhibitor Aliskiren and the different cigarette of isovanillin
The important source material of acylhydrazone complex.Some researches show that with the substance C A-4 of efficient anti-vascular cancer effect, its synthesis material is exactly
Isovanillin.Antibiotic santiagonamine of new generation is also using isovanillin as Material synthesis.Liu Tao etc. is blue using an unusually sweet smell
Element and tyrasamine are initial material, synthesize racemic galanthamine, which is that clinic is used for treating senile dementia and note in recent years
Recall the good drug of obstacle.It is rich to wait with the bromo- isovanillin of the 2- that isovanillin is Material synthesis, in anticancer and radioresistance, change
It treats and has a wide range of applications in hypersitization medicine.Isovanillin still synthesize anticancer drug NSC 817373, Gefitinib, it is non-wake up etc.
The starting material of biological medicament.Isovanillin is not only a kind of important pharmaceutical intermediate, itself can also be used for as drug
Release spasm.
Isovanillin is extracted from plant, isolate and purify it is difficult and of high cost, it is uneconomical.So acquisition of isovanillin
Use chemical synthesis more.But many chemical synthesis process are during the reaction among the inherently expensive drug of raw material
Body, and many process byproducts pollution environment.
The content of the invention
It is an object of the invention to provide a kind of preparation methods of isovanillin, and raw material is easy to get, at low cost, process control
Simply, it is easy to operate, industrialized production is easily formed, yield is high, and wastewater flow rate is few, beneficial to environmental protection.
Realization that the present invention adopts the following technical solutions：
A kind of preparation method of isovanillin, includes the following steps：
(1), 4~8h, mistake are reacted in the alkaline environment that dimethyl suflfate and Ethyl vanillin solution are 5~40 DEG C in temperature
Filter, takes filter residue to obtain intermediate.
(2), intermediate and the concentrated sulfuric acid react 2~7h under atmosphere of inert gases that temperature is 40~70 DEG C, condition of negative pressure.
Further, in preferred embodiments of the present invention, the preparation method of above-mentioned Ethyl vanillin solution is：Ethyl is fragrant
Lan Su is added in the aqueous slkali that pH is 12~14.
Further, in preferred embodiments of the present invention, above-mentioned aqueous slkali is sodium hydroxide solution, Ethyl vanillin and hydrogen
The mass ratio of sodium hydroxide solution is 1：2.5~4.
Further, in preferred embodiments of the present invention, in above-mentioned steps (1), Ethyl vanillin and dimethyl suflfate
Mass ratio is 1：0.8~1.2.
Further, in preferred embodiments of the present invention, in above-mentioned steps (1), after filtering, washing, drying are further included
The step of.
Further, in preferred embodiments of the present invention, in above-mentioned steps (2), the mass concentration of the concentrated sulfuric acid for 90~
98%.
Further, in preferred embodiments of the present invention, the mass ratio of above-mentioned intermediate and the concentrated sulfuric acid is 1：1.5~5.
Further, in preferred embodiments of the present invention, in above-mentioned steps (2), negative pressure is -90~-98Kpa.
Further, in preferred embodiments of the present invention, after above-mentioned steps (2), further include the isovanillin after reaction
The step of crude product is purified.
Further, in preferred embodiments of the present invention, above-mentioned purifying carries out as follows：By an unusually sweet smell after reaction
Blue element crude product is transferred in water to be extracted after dilution using ethyl acetate.
The advantageous effect of preparation method for the isovanillin that presently preferred embodiments of the present invention provides is：First make Ethyl vanillin
3- ethyoxyls -4-methoxybenzaldehyde intermediate is obtained by the reaction with dimethyl suflfate, then makes 3- ethyoxyls -4-methoxybenzaldehyde
Isovanillin is obtained by the reaction with the concentrated sulfuric acid in intermediate under inert gas, condition of negative pressure, and reaction equation is：
The first step：
Second step：
Wherein：First step reaction temperature is controlled at 5~40 DEG C, and temperature is too low, and reaction speed is slow, and reacts incomplete；Temperature
Height is spent, dimethyl suflfate can be rapidly decomposed into sulfuric acid and methanol, and materials conversion rate is low.Second step reacts, in inert gas atmosphere
It is reacted under enclosing, 3- ethyoxyls -4-methoxybenzaldehyde intermediate is avoided to be carbonized under the action of the concentrated sulfuric acid, and
It is reacted under condition of negative pressure, the low-boiling-point substances such as water can be removed, be conducive to improve reaction rate and conversion ratio.Second step reaction temperature
Degree control is at 40~70 DEG C, and reaction temperature is too low, and reaction speed is slow, and reaction is incomplete；Reaction temperature is excessively high impurity to be caused to be given birth to
Into.This preparation method uses Ethyl vanillin, dimethyl suflfate and the concentrated sulfuric acid, and raw material is easy to get, at low cost, process control letter
It is single, it is easy to operate, industrialized production is easily formed, yield is high, and wastewater flow rate is few, beneficial to environmental protection.
Specific embodiment
It, below will be in the embodiment of the present invention to make the purpose, technical scheme and advantage of the embodiment of the present invention clearer
Technical solution be clearly and completely described.The person that is not specified actual conditions in embodiment, builds according to normal condition or manufacturer
The condition of view carries out.Reagents or instruments used without specified manufacturer is the conventional production that can be obtained by commercially available purchase
Product.
The preparation method of the isovanillin of the embodiment of the present invention is specifically described below.
A kind of preparation method of isovanillin, includes the following steps：
(1), Ethyl vanillin solution is prepared：Ethyl vanillin is added in the aqueous slkali that pH is 12~14.In the present invention,
It is 12~14 to control pH, is conducive to subsequent reaction, aqueous slkali can be sodium hydroxide solution or potassium hydroxide solution.Preferably
Sodium hydroxide solution.
The preparation method of sodium hydroxide solution is：Sodium hydroxide, which is dissolved in the water, controls the mass concentration of sodium hydroxide
It is preferably 10-15% in 8-20%.Naoh concentration is too low, causes reaction speed slow；Excessive concentration, reaction speed is too fast,
It is not easy to control.
In the present invention, the mass ratio of Ethyl vanillin and sodium hydroxide solution is 1：2.5~4, so as to control ethyl chinese cymbidium
The concentration of Ethyl vanillin in plain solution.
(2), 4~8h, mistake are reacted in the alkaline environment that dimethyl suflfate and Ethyl vanillin solution are 5~40 DEG C in temperature
Filter, takes filter residue to obtain intermediate.
3- ethyoxyls -4-methoxybenzaldehyde intermediate, step hair is obtained by the reaction with dimethyl suflfate in Ethyl vanillin
Raw reaction equation is：
The reaction temperature is controlled at 5~40 DEG C, and temperature is too low, and reaction speed is slow, and reacts incomplete；Temperature is excessively high, sulphur
Dimethyl phthalate can be rapidly decomposed into sulfuric acid and methanol, and materials conversion rate is low.
Preferably, the mass ratio of Ethyl vanillin and dimethyl suflfate is 1：0.8~1.2.Dimethyl suflfate dosage is too low,
Cause Ethyl vanillin reaction incomplete；Dimethyl suflfate dosage is excessive, remains excessive dimethyl suflfate and adds follow-up place
The difficulty of reason, the dimethyl suflfate contained in the solution after reaction are not easy to remove.
More preferably, the mode for adding in dimethyl suflfate can be disposable all additions, can also be added with the mode of dropwise addition
Enter, the mode being preferably added dropwise, be so conducive to control reaction rate.
Preferably, dimethyl suflfate is added in Ethyl vanillin solution, in the case where temperature is 5~40 DEG C of alkaline condition
4~8h is reacted, filters, wash, be dried to obtain intermediate.4~8h is reacted under conditions of 5~40 DEG C, in reaction process slowly
3- ethyoxyls -4-methoxybenzaldehyde crystalline intermediates are precipitated.After the completion of reaction, filtering, washing, drying are obtained among synthesis
Body, the net content of intermediate is more than 99.1%, and yield is more than 95%, and reaction temperature is low, the reaction time is short, high income.
(3), intermediate and the concentrated sulfuric acid react 2~7h under atmosphere of inert gases that temperature is 40~70 DEG C, condition of negative pressure
Obtain isovanillin crude product.
3- ethyoxyls -4-methoxybenzaldehyde intermediate reacts generation isovanillin, step hair under the conditions of the concentrated sulfuric acid
Raw reaction equation is：
It is reacted under atmosphere of inert gases, avoids 3- ethyoxyls -4-methoxybenzaldehyde intermediate in the concentrated sulfuric acid
Effect is lower to be carbonized, and is reacted under condition of negative pressure, can remove the low-boiling-point substances such as water, be conducive to improve reaction rate
And conversion ratio.
In the present invention, inert gas can be nitrogen or argon gas etc., as long as 3- ethyoxyl -4- methoxybenzene first can be avoided
The gas that aldehyde intermediate is carbonized under the action of the concentrated sulfuric acid is all protection scope of the present invention.
In detail, intermediate is added in into enamel reaction still, avoids follow-up concentrated sulfuric acid corrosion container, then excluded using nitrogen
Oxygen in enamel reaction still, then adds in the concentrated sulfuric acid in confined conditions, and further deoxygenation ensures that oxygen content is small in reaction kettle
In 50ppm, 3- ethyoxyls -4-methoxybenzaldehyde intermediate is further avoided to be carbonized.
Preferably, the mass concentration of the concentrated sulfuric acid is 90~98%, and the mass ratio of intermediate and the concentrated sulfuric acid is 1：1.5~5.It is dense
Spend low, reaction is incomplete, and reaction speed is slow.It measures very few also result in and reacts incomplete, yield is relatively low, product content deficiency.
Sulfuric acid dosage is excessive, causes wastewater flow rate excessive, is unfavorable for environmental protection.
Second step reaction temperature is controlled at 40~70 DEG C, and reaction temperature is too low, and reaction speed is slow, and reaction is incomplete；Reaction
Temperature is excessively high impurity to be caused to generate.It is reacted under condition of negative pressure, pressure control turns in -90~-98Kpa, 2~7h of reaction
Rate is more than 98%, and high conversion rate is conducive to industrial production.
(4), the isovanillin crude product after reaction is purified.Specifically, the isovanillin crude product after reaction is transferred to
After diluting in water carry out that pure isovanillin is obtained by extraction using ethyl acetate.Due to containing the concentrated sulfuric acid in isovanillin crude product
Impurity, so, it is first passed through ice water and is diluted, i.e., isovanillin crude product is transferred in ice water, prevent bumping.The concentrated sulfuric acid with
The mass ratio of water is 1：2~4.Water is few, and sulfuric acid concentration is high, and product solubility is caused to increase, and product yield reduces.Water mistake
More, wastewater flow rate increases.
It is extracted after dilution using solvent ethyl acetate, the mass ratio of ethyl acetate and water is 0.5~1.5：1, extraction times
For 3~5 times, the product in reaction solution has been extracted, ethyl acetate is recovered by distillation, an unusually sweet smell orchid is slowly precipitated in distillation process
Element, color are rufous, the purified product by way of vacuum distillation, and obtained isovanillin is white crystal, and content is
More than 98.5%, yield 92%.
This preparation method is easy using raw materials, raw materials such as Ethyl vanillin, sodium hydroxide, dimethyl suflfate and the concentrated sulfuric acids
, at low cost, process control is simple, easy to operate, easily forms industrialized production, and yield is high, and product purity is high, and wastewater flow rate is few, profit
In environmental protection.
Embodiment 1
A kind of preparation method of isovanillin, includes the following steps：
(1), 6h is reacted in the alkaline environment that dimethyl suflfate and Ethyl vanillin solution are 20 DEG C in temperature, filters, take
Filter residue obtains intermediate.
(2), intermediate and the concentrated sulfuric acid react 5h under atmosphere of inert gases that temperature is 50 DEG C, condition of negative pressure.
Embodiment 2
A kind of preparation method of isovanillin, includes the following steps：
(1), Ethyl vanillin is added in the potassium hydroxide solution that pH is 12 and obtains Ethyl vanillin solution.
(2), 6h is reacted in the alkaline environment that dimethyl suflfate and Ethyl vanillin solution are 30 DEG C in temperature, filters, washes
It washs, be dried to obtain intermediate.Wherein, the mass ratio of Ethyl vanillin and dimethyl suflfate is 1：1.
(3), intermediate is added in into enamel reaction still, and the concentrated sulfuric acid that mass concentration is 92% is added in after being passed through nitrogen,
Temperature is 60 DEG C, pressure obtains isovanillin crude product to carry out reaction 3h under conditions of -92Kpa.Wherein, intermediate and the concentrated sulfuric acid
Mass ratio be 1：2.
(4), the isovanillin crude product after reaction is transferred to after being diluted in water and carries out that an unusually sweet smell is obtained by extraction using ethyl acetate
Lan Su, wherein, the mass ratio of the concentrated sulfuric acid and water is 1：3；The mass ratio of ethyl acetate and water is 1：1, the yield of isovanillin is
92%.
Embodiment 3
A kind of preparation method of isovanillin, includes the following steps：
(1), Ethyl vanillin is added in the sodium hydroxide solution that mass concentration is 8% to obtain Ethyl vanillin molten
Liquid.
(2), 4h is reacted in the alkaline environment that dimethyl suflfate and Ethyl vanillin solution are 5 DEG C in temperature, filters, washes
It washs, be dried to obtain intermediate.Wherein, the mass ratio of Ethyl vanillin and dimethyl suflfate is 1：0.8.
(3), intermediate is added in into enamel reaction still, and the concentrated sulfuric acid that mass concentration is 90% is added in after being passed through nitrogen,
Temperature is 40 DEG C, pressure obtains isovanillin crude product to carry out reaction 2h under conditions of -90Kpa.Wherein, intermediate and the concentrated sulfuric acid
Mass ratio be 1：1.5.
(4), the isovanillin crude product after reaction is transferred to after being diluted in ice water and is extracted using ethyl acetate, depressurizes steaming
It evaporates to obtain pure isovanillin, wherein, the mass ratio of the concentrated sulfuric acid and ice water is 1：2；The mass ratio of ethyl acetate and ice water is
0.5：1, the yield of isovanillin is 91%.
Embodiment 4
A kind of preparation method of isovanillin, includes the following steps：
(1), Ethyl vanillin is added in the sodium hydroxide solution that mass concentration is 20% to obtain Ethyl vanillin molten
Liquid.
(2), 8h is reacted in the alkaline environment that dimethyl suflfate and Ethyl vanillin solution are 40 DEG C in temperature, filters, washes
It washs, be dried to obtain intermediate.Wherein, the mass ratio of Ethyl vanillin and dimethyl suflfate is 1：1.2.
(3), intermediate is added in into enamel reaction still, and the concentrated sulfuric acid that mass concentration is 98% is added in after being passed through nitrogen,
Temperature is 70 DEG C, pressure obtains isovanillin crude product to carry out reaction 7h under conditions of -98Kpa.Wherein, intermediate and the concentrated sulfuric acid
Mass ratio be 1：5.
(4), the isovanillin crude product after reaction is transferred to after being diluted in ice water and is extracted using ethyl acetate, depressurizes steaming
It evaporates to obtain pure isovanillin, wherein, the mass ratio of the concentrated sulfuric acid and ice water is 1：4；The mass ratio of ethyl acetate and ice water is
1.5：1, the yield of isovanillin is 94%.
Embodiment 5
A kind of preparation method of isovanillin, includes the following steps：
(1), Ethyl vanillin is added in the sodium hydroxide solution that mass concentration is 10% to obtain Ethyl vanillin molten
Liquid.
(2), 6h is reacted in the alkaline environment that dimethyl suflfate and Ethyl vanillin solution are 20 DEG C in temperature, filters, washes
It washs, be dried to obtain intermediate.Wherein, the mass ratio of Ethyl vanillin and dimethyl suflfate is 1：1.
(3), intermediate is added in into enamel reaction still, and the concentrated sulfuric acid that mass concentration is 96% is added in after being passed through nitrogen,
Temperature is 60 DEG C, pressure obtains isovanillin crude product to carry out reaction 5h under conditions of -96Kpa.Wherein, intermediate and the concentrated sulfuric acid
Mass ratio be 1：4.
(4), the isovanillin crude product after reaction is transferred to after being diluted in ice water and is extracted using ethyl acetate, depressurizes steaming
It evaporates to obtain pure isovanillin, wherein, the mass ratio of the concentrated sulfuric acid and ice water is 1：3；The mass ratio of ethyl acetate and ice water is
1：1, the yield of isovanillin is 95%.
Embodiments described above is part of the embodiment of the present invention, instead of all the embodiments.The reality of the present invention
The detailed description for applying example is not intended to limit the scope of claimed invention, but is merely representative of the selected implementation of the present invention
Example.Based on the embodiments of the present invention, those of ordinary skill in the art are obtained without creative efforts
Every other embodiment, belongs to the scope of protection of the invention.
Claims (10)
1. a kind of preparation method of isovanillin, which is characterized in that include the following steps：
(1), 4~8h is reacted in the alkaline environment that dimethyl suflfate and Ethyl vanillin solution are 5~40 DEG C in temperature, filtered,
Filter residue is taken to obtain intermediate；
(2), the intermediate and the concentrated sulfuric acid react 2~7h under atmosphere of inert gases that temperature is 40~70 DEG C, condition of negative pressure.
2. preparation method according to claim 1, which is characterized in that the preparation method of the Ethyl vanillin solution is：
Ethyl vanillin is added in the aqueous slkali that pH is 12~14.
3. preparation method according to claim 2, which is characterized in that the aqueous slkali be sodium hydroxide solution, the second
The mass ratio of base vanillic aldehyde and the sodium hydroxide solution is 1：2.5~4.
4. preparation method according to claim 1, which is characterized in that in the step (1), the Ethyl vanillin and institute
The mass ratio for stating dimethyl suflfate is 1：0.8~1.2.
5. preparation method according to claim 4, which is characterized in that in the step (1), after the filtering, also wrap
Include the step of washing, drying.
6. preparation method according to claim 1, which is characterized in that in the step (2), the quality of the concentrated sulfuric acid is dense
It spends for 90~98%.
7. preparation method according to claim 6, which is characterized in that the mass ratio of the intermediate and the concentrated sulfuric acid is
1：1.5~5.
8. preparation method according to claim 7, which is characterized in that in the step (2), the negative pressure for -90~-
98Kpa。
9. preparation method according to claim 1, which is characterized in that after the step (2), further including will be different after reaction
The step of crude vanillin is purified.
10. preparation method according to claim 9, which is characterized in that the purifying carries out as follows：It will reaction
Isovanillin crude product afterwards is transferred in water and is extracted after dilution using ethyl acetate.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113185391A (en) * | 2021-04-12 | 2021-07-30 | 浙江优创材料科技股份有限公司 | Method for synthesizing isovanillin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5786516A (en) * | 1994-10-24 | 1998-07-28 | Rhone-Poulenc Chimie | Process for the preparation of isovanillin |
| CN105439837A (en) * | 2016-01-15 | 2016-03-30 | 常州永和精细化学有限公司 | Synthetic method of 6-Bromoisovanillin |
-
2017
- 2017-12-27 CN CN201711442415.4A patent/CN108084000A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5786516A (en) * | 1994-10-24 | 1998-07-28 | Rhone-Poulenc Chimie | Process for the preparation of isovanillin |
| CN105439837A (en) * | 2016-01-15 | 2016-03-30 | 常州永和精细化学有限公司 | Synthetic method of 6-Bromoisovanillin |
Non-Patent Citations (1)
| Title |
|---|
| 李大伟等: "利用对羟基苯甲醛合成异香兰素", 《南昌大学学报（理科版）》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113185391A (en) * | 2021-04-12 | 2021-07-30 | 浙江优创材料科技股份有限公司 | Method for synthesizing isovanillin |
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Application publication date: 20180529 |