CN104496894A - Preparation method of high purity nicotinamide and nicotinic acid - Google Patents
Preparation method of high purity nicotinamide and nicotinic acid Download PDFInfo
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- CN104496894A CN104496894A CN201410672124.4A CN201410672124A CN104496894A CN 104496894 A CN104496894 A CN 104496894A CN 201410672124 A CN201410672124 A CN 201410672124A CN 104496894 A CN104496894 A CN 104496894A
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- water
- nicotinic acid
- nicotinonitrile
- ethanol
- high purity
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
Abstract
The invention provides a preparation method of high purity nicotinamide and nicotinic acid. In an ethanol and water system and in the presence of NaOH and MnO2, 3-cyanopyridine hydrolyzes to obtain high content of nicotinamide and nicotinic acid by adjusting the ratio of ethanol and water. When ethanol and water are in the weight ratio of 19:1, 3-cyanopyridine hydrolyzes to obtain is 99.5% of nicotinamide, and the yield is higher than 95%; and when the ethanol and water are in the weight ratio of 1:9, the 3-cyanopyridine hydrolyzes to obtain 99.5% of nicotinic acid, and the yield is more than 95%. The method has the characteristics of mild reaction conditions, high product purity and high yield; and only by adjusting the content of ethanol, high purity nicotinamide and nicotinic acid are obtained. At the same time, the method has less waste and less pollution, and is beneficial for industrialized production.
Description
Technical field
The present invention relates to field of fine chemical, be specifically related to a kind of high purity niacinamide and nicotinic acid preparation method.
Background technology
Niacinamide is vitamin B group; formal name used at school is pyridine-3-carboxamide (nicotinamide, niacinamide), VITAMIN PP; be called for short VB3 or NSA; it is one of integral part of coenzyme and coenzyme etc.; participate in the multiple redox reaction of body, be medically used for the treatment of pellagra, stomatitis, glossitis, hepatic diseases and sunburn etc.; Heavy dose can reduce cholesterol and triglyceride level, its physiological action and nicotinic acid similar, but better water-soluble, without obvious vasodilation effect.
Nicotinic acid belongs to vitamin B complex compound, is indispensable nutritive ingredient in human body.Nicotinic acid as pharmaceutical intermediate, can also synthesize the multiple amides and the ester derivative medicine that have important use; Nicotinic acid or a kind of very important fodder additives and foodstuff additive; Also a small amount of for dyestuff, household chemicals, brightener etc.
The industrial method being generated niacinamide by catalytic hydrolysis nicotinonitrile, its catalyzer mainly contains acid, alkali and a few class water-insoluble catalyzer, as: nickel oxide, Manganse Dioxide, magnesium oxide etc.; Mainly prepare nicotinic acid by enzymic hydrolysis nicotinonitrile at present.At present in the method for traditional synthesis niacinamide, always with the generation of by product nicotinic acid, thus the problem causing niacinamide, nicotinic acid and catalyzer difficulty to be separated, be separated and obtain highly purified niacinamide product needed and carry out a large amount of aftertreatment work.
This method reaction conditions provided by the invention is gentle, environmental friendliness, and by changing the volume ratio of ethanol and water, obtain highly purified product, this kind of method is simple to operate, is convenient to suitability for industrialized production.
Summary of the invention
The object of the invention is improved on the basis of traditional technology synthesis niacinamide and nicotinic acid and optimize, obtain niacinamide and the nicotinic acid product of high-content height yield.
The object of the invention is to be realized by following technical scheme:
A preparation method for high purity niacinamide, is characterized in that: in ethanol and aqueous systems, at NaOH solution and MnO
2under existent condition, nicotinonitrile is hydrolyzed, by regulating the ratio of second alcohol and water, obtain the niacinamide of high-content, the mass ratio of described second alcohol and water is (2-20): 1, nicotinonitrile and MnO
2mass ratio be (4-6): 1, the mass ratio of nicotinonitrile and NaOH is (16-100): 1, and the concentration of described NaOH solution is 5%, and hydrolysising reacting temperature is 85 ~ 100 DEG C.
The preparation method of described high purity niacinamide, is characterized in that: the mass ratio of described second alcohol and water is 19:1.
A preparation method for high purity nicotinoyl, is characterized in that: in ethanol and aqueous systems, at NaOH solution and MnO
2under existent condition, nicotinonitrile is hydrolyzed, by regulating the ratio of second alcohol and water, obtain the nicotinoyl of high-content, the mass ratio of described second alcohol and water is 1:(2-12), nicotinonitrile and MnO
2mass ratio be (4-6): 1, the mass ratio of nicotinonitrile and NaOH is (5-6): 1, and the concentration of described NaOH solution is 5%, and hydrolysising reacting temperature is 85 ~ 100 DEG C.
The preparation method of described high purity nicotinic acid, is characterized in that: the mass ratio of described second alcohol and water is 1:9.
The preparation of described a kind of high purity niacinamide, is characterized in that: described hydrolysising reacting temperature is 95 DEG C.
Advantage of the present invention:
1) reaction conditions is gentle, simple to operate.
2) reacted ethanol can recovery.
3) this kind of method only needs, by the ratio of adjustment second alcohol and water, just can obtain the product of high purity high-content.
4) raw material and solvent are easy to get, and the three wastes are few, pollute few, are easy to suitability for industrialized production.
Embodiment
Below by example, the present invention is described, but the present invention is not limited to these embodiments.
embodiment 1:
In the four-hole boiling flask of 1000ml, add 121g nicotinonitrile and 339.5g ethanol, stir 30min, nicotinonitrile is dissolved completely.Then get 7.275g sodium hydroxide and be dissolved in 145.5g water the NaOH solution preparing 5%.Under whipped state, add the sodium hydroxide solution prepared, add 24.2gMnO afterwards
2, be warmed up to 95 DEG C of reaction 8h.After reaction terminates, filter, removing catalyzer MnO
2, then heat up and take off solvent, filter and obtain niacinamide.The content of product is 85%, and yield is 82%.
embodiment 2:
In the four-hole boiling flask of 1000ml, add 121g nicotinonitrile and 412g ethanol, stir 30min, nicotinonitrile is dissolved completely.Then get 3.83g sodium hydroxide and be dissolved in 72.8g water the NaOH solution preparing 5%.Under whipped state, add the sodium hydroxide solution prepared, add 24.2gMnO afterwards
2, be warmed up to 95 DEG C of reaction 8h.After reaction terminates, filter, removing catalyzer MnO
2, then heat up and take off solvent, filter and obtain niacinamide.The content of product is 95%, and yield is 90%.
embodiment 3:
In the four-hole boiling flask of 1000ml, add 121g nicotinonitrile and 460.8g ethanol, stir 30min, nicotinonitrile is dissolved completely.Then get 1.21g sodium hydroxide and be dissolved in 24.2g water the NaOH solution preparing 5%.Under whipped state, add the sodium hydroxide solution prepared, add 24.2gMnO afterwards
2, be warmed up to 95 DEG C of reaction 8h.After reaction terminates, filter, removing catalyzer MnO
2, then heat up and take off solvent, filter and obtain niacinamide.The content of product is 99.5%, and yield is 96%.
embodiment 4:
In the four-hole boiling flask of 1000ml, add 121g nicotinonitrile and 38.8g ethanol, stir 30min, nicotinonitrile is dissolved completely.Then get 22.3g sodium hydroxide and be dissolved in 446.2g water the NaOH solution preparing 5%.Under whipped state, add the sodium hydroxide solution prepared, add 24.2gMnO afterwards
2, be warmed up to 95 DEG C of reaction 8h.After reaction terminates, filter, removing catalyzer MnO
2, then heat up and take off solvent, filter and obtain nicotinic acid.The content of product is 90%, and yield is 85%.
embodiment 5:
In the four-hole boiling flask of 1000ml, add 121g nicotinonitrile and 48.5g ethanol, stir 30min, nicotinonitrile is dissolved completely.Then get 21.8g sodium hydroxide and be dissolved in 436.5g water the NaOH solution preparing 5%.Under whipped state, add the sodium hydroxide solution prepared, add 24.2g MnO afterwards
2, be warmed up to 95 DEG C of reaction 8h.After reaction terminates, filter, removing catalyzer MnO
2, then heat up and take off solvent, filter and obtain nicotinic acid.The content of product is 99.5%, and yield is 96%.
embodiment 6:
In the four-hole boiling flask of 1000ml, add 121g nicotinonitrile and 126.1g ethanol, stir 30min, nicotinonitrile is dissolved completely.Then get 21.8g sodium hydroxide and be dissolved in 358.9g water the NaOH solution preparing 5%.Under whipped state, add the sodium hydroxide solution prepared, add 24.2g MnO afterwards
2, be warmed up to 95 DEG C of reaction 8h.After reaction terminates, filter, removing catalyzer MnO
2, then heat up and take off solvent, filter and obtain nicotinic acid.The content of product is 87%, and yield is 83%.
Claims (5)
1. a preparation method for high purity niacinamide, is characterized in that: in ethanol and aqueous systems, at NaOH solution and MnO
2under existent condition, nicotinonitrile is hydrolyzed, by regulating the ratio of second alcohol and water, obtain the niacinamide of high-content, the mass ratio of described second alcohol and water is (2-20): 1, nicotinonitrile and MnO
2mass ratio be (4-6): 1, the mass ratio of nicotinonitrile and NaOH is (16-100): 1, and the concentration of described NaOH solution is 5%, and hydrolysising reacting temperature is 85 ~ 100 DEG C.
2. the preparation method of high purity niacinamide according to claim 1, is characterized in that: the mass ratio of described second alcohol and water is 19:1.
3. a preparation method for high purity nicotinoyl, is characterized in that: in ethanol and aqueous systems, at NaOH solution and MnO
2under existent condition, nicotinonitrile is hydrolyzed, by regulating the ratio of second alcohol and water, obtain the nicotinoyl of high-content, the mass ratio of described second alcohol and water is 1:(2-12), nicotinonitrile and MnO
2mass ratio be (4-6): 1, the mass ratio of nicotinonitrile and NaOH is (5-6): 1, and the concentration of described NaOH solution is 5%, and hydrolysising reacting temperature is 85 ~ 100 DEG C.
4. the preparation method of high purity nicotinic acid according to claim 3, is characterized in that: the mass ratio of described second alcohol and water is 1:9.
5. the preparation of a kind of high purity niacinamide according to claim 1, is characterized in that: described hydrolysising reacting temperature is 95 DEG C.
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| CN201410672124.4A CN104496894A (en) | 2014-11-22 | 2014-11-22 | Preparation method of high purity nicotinamide and nicotinic acid |
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| CN201410672124.4A CN104496894A (en) | 2014-11-22 | 2014-11-22 | Preparation method of high purity nicotinamide and nicotinic acid |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107488143A (en) * | 2017-08-17 | 2017-12-19 | 北京贝丽莱斯生物化学有限公司 | A kind of niacinamide and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107488143A (en) * | 2017-08-17 | 2017-12-19 | 北京贝丽莱斯生物化学有限公司 | A kind of niacinamide and preparation method thereof |
| CN107488143B (en) * | 2017-08-17 | 2020-09-18 | 北京贝丽莱斯生物科技有限公司 | Nicotinamide and preparation method thereof |
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Application publication date: 20150408 |