CN103664679A - Synthetic method of N-acetyl-beta-alanine nitrate - Google Patents
Synthetic method of N-acetyl-beta-alanine nitrate Download PDFInfo
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- CN103664679A CN103664679A CN201310685234.XA CN201310685234A CN103664679A CN 103664679 A CN103664679 A CN 103664679A CN 201310685234 A CN201310685234 A CN 201310685234A CN 103664679 A CN103664679 A CN 103664679A
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Abstract
The invention discloses a synthetic method of N-acetyl-beta-alanine nitrate and belongs to acylation of amido. The synthetic method specifically comprises the following steps: beta-alanine and acetic anhydride are used as raw materials, glacial acetic acid is used as a reaction medium, and a white crystal N- N-acetyl-beta-alanine is obtained through steps of stirring, heating, thermostatic reaction, distillation under reduced pressure, cooling, devitrification and the like; then, the N-acetyl-beta-alanine reacts with nitric acid, and the N-acetyl-beta-alanine nitrate is obtained through steps of heating, thermostatic reaction, distillation under reduced pressure, cooling and devitrification. According to the synthetic method, the product yield is high, the purity is high, the reaction condition is moderate, and the acetic acid and the filtrate generated through distillation during the preparation process can be used indiscriminately, so that the purpose of environmental protection can be achieved.
Description
Technical field
The invention belongs to the acidylate of amido, be specifically related to a kind of synthetic method of N-acetyl-Beta-alanine nitrate.
Background technology
L-Ala is the fundamental unit that forms protein, is one of 21 seed amino acids that form human body protein.The amino acid of constitutive protein matter molecule is all L-amino acid.Because they are in same pH environment, all kinds of amino acid whose electriferous states are different, and they have different iso-electric points, and this is the principle of electrophoretic method and chromatography amino acid separation.L-Ala has α-alanine and two kinds of isomerss of Beta-alanine.α-alanine also claims 2-alanine.200 ℃ of above distillations, decompose between 264～296 ℃ with rate of heating difference, are a kind of compositions of constitutive protein matter, belong to the nonessential amino acid of human body in trophology, how from fermentation method and natural product, to extract at present.Beta-alanine also claims 3-alanine, clear crystal.198 ℃ of fusing points, water-soluble, be slightly soluble in ethanol, be insoluble to ether, for the synthesis of pantothenic acid and plating, also for the research of microbiology and biological chemistry etc., can be by the proteolysis such as silk gum, gelatin, zein refining forming, also available chemical process is synthetic.
L-Ala is for manufacturing vitamin B6, synthetic pantothenic acid calcium and other organic compound raw materials.Make an addition to the seasoning effect that can strengthen chemical seasoning in food, improve sense of taste and the organic acid tart flavour of sweeting agent, improve the quality containing alcoholic beverage, prevent oils oxidation and improve infusion of food local flavor etc.Also can be used as biochemical reagents, for biological chemistry and microbe research aspect.
Current amino acid whose acetylize technology mainly adopts alkaline process acidylate.Concrete grammar is: amino acid is dissolved in aqueous sodium hydroxide solution, then adds at a certain temperature diacetyl oxide, after acylation reaction finishes, reaction solution is concentrated, last low temperature crystallization obtains product.Alkaline process acidylate transformation efficiency is high; reaction conditions gentleness is easy to control, but in production process, reagent consumption is large, and in actual production, its mol ratio is amino acid: NaOH: join=1:5:1.4 ~ 1.5 of acetic acid; can produce a large amount of sodium acetates simultaneously and be difficult to effective separation, cause N-second phthalein amino acid yield lower.And the existence meeting of sodium acetate is to the subsequent process in L-amino acids production as split in system, racemization brings very large difficulty.
Summary of the invention
The present invention proposes in order to overcome the shortcoming existing in prior art, its objective is the synthetic method that a kind of N-acetyl-Beta-alanine nitrate is provided.
Chemical equation of the present invention is as follows:
Technical scheme of the present invention is:
A synthetic method for N-acetyl-Beta-alanine nitrate, comprises the steps:
A. Beta-alanine is added in reaction vessel, then add glacial acetic acid, stir;
While being b. heated to 30 ℃ ~ 90 ℃, in reaction vessel, drip acid anhydrides;
C. isothermal reaction 1 ~ 5 hour at 30 ℃ ~ 90 ℃ after being added dropwise to complete;
D. after reaction finishes, underpressure distillation, the Glacial acetic acid distilling out recycles;
E. be cooled to 5 ℃ ~ 25 ℃, in reaction vessel, add solvent crystallize out;
F. the crystal of separating out is mixed with nitric acid, stir, be heated to 30 ℃ ~ 80 ℃, isothermal reaction 1 ~ 5 hour;
G. isothermal reaction finishes, and underpressure distillation is cooled to 5 ℃ ~ 15 ℃, adds solvent crystallize out;
H. freeze overnight, filters, dry, can obtain N-acetyl-Beta-alanine nitrate finished product;
I. the mother liquor that filters gained substitutes solvent and recycles.
The glacial acetic acid adding in described step a and the mass ratio of Beta-alanine are 1 ~ 5:1.
In described step b, acid anhydrides is diacetyl oxide.
The acid anhydrides adding in described step b and the mol ratio of Beta-alanine are 0.95 ~ 2:1.
Solvent in described step e, step g and step I is acetone or ethyl acetate.
The solvent adding in described step e and step g and the mass ratio of Beta-alanine are 1 ~ 5:1.
The mol ratio of the nitric acid adding in described step f and N-acetyl-Beta-alanine crystal is 1 ~ 1.5:1.
The invention has the beneficial effects as follows:
Synthetic method product yield of the present invention is high, purity is high, reaction conditions is gentle, and the distillation gained acetic acid in preparation process can be applied mechanically, and filtrate can be applied mechanically, so can reach the object of environmental protection.
Embodiment
Below in conjunction with embodiment, the present invention is described in detail:
A synthetic method for N-acetyl-Beta-alanine nitrate, comprises the steps:
A. Beta-alanine is added in reaction vessel, then add glacial acetic acid, stir;
While being b. heated to 30 ℃ ~ 90 ℃, in reaction vessel, drip acid anhydrides;
C. isothermal reaction 1 ~ 5 hour at 30 ℃ ~ 90 ℃ after being added dropwise to complete;
D. after reaction finishes, underpressure distillation, the Glacial acetic acid distilling out recycles;
E. be cooled to 5 ℃ ~ 25 ℃, in reaction vessel, add solvent crystallize out;
F. the crystal of separating out is mixed with nitric acid, stir, be heated to 30 ℃ ~ 80 ℃, isothermal reaction 1 ~ 5 hour;
G. isothermal reaction finishes, and underpressure distillation is cooled to 5 ℃ ~ 15 ℃, adds solvent crystallize out;
H. freeze overnight, filters, dry, can obtain N-acetyl-Beta-alanine nitrate finished product;
I. the mother liquor that filters gained substitutes solvent and recycles.
The glacial acetic acid adding in described step a and the mass ratio of Beta-alanine are 1 ~ 5:1.
In described step b, acid anhydrides is diacetyl oxide.
The acid anhydrides adding in described step b and the mol ratio of Beta-alanine are 0.95 ~ 2:1.
Solvent in described step e, step g and step I is acetone or ethyl acetate.
The solvent adding in described step e and step g and the mass ratio of Beta-alanine are 1 ~ 5:1.
The mol ratio of the nitric acid adding in described step f and N-acetyl-Beta-alanine crystal is 1 ~ 1.5:1.
Embodiment 1
A synthetic method for N-acetyl-Beta-alanine nitrate, comprises the steps:
A. by 89g(1mol) Beta-alanine adds in reaction vessel, then add 89g glacial acetic acid, stir
While being b. heated to 90 ℃, in reaction vessel, drip 204g(2mol) diacetyl oxide;
C. isothermal reaction 1 hour at 90 ℃ after being added dropwise to complete;
D. after reaction finishes, underpressure distillation, the Glacial acetic acid distilling out recycles;
E. be cooled to 5 ℃, in reaction vessel, add ethyl acetate 445g crystallize out, suction filtration, dry, obtain white crystal N-acetyl-Beta-alanine 115g, yield is 88%, purity is 98.65%;
F. by the N-acetyl-Beta-alanine crystal 115g(0.88mol separating out) be that 65% nitric acid 0.88mol mixes with massfraction, stir, be heated to 80 ℃, isothermal reaction 1 hour;
G. isothermal reaction finishes, and underpressure distillation is cooled to 5 ℃, adds ethyl acetate 250mL crystallize out;
H. freeze overnight, filters, dry, can obtain N-acetyl-Beta-alanine nitrate finished product 155g, and yield is 80%, and purity is 98.70%;
I. the mother liquor that filters gained substitutes solvent and recycles.
Embodiment 2
A synthetic method for N-acetyl-Beta-alanine nitrate, comprises the steps:
A. by 89g(1mol) Beta-alanine adds in reaction vessel, then add 445g glacial acetic acid, stir
While being b. heated to 30 ℃, in reaction vessel, drip 96.9g(0.95mol) diacetyl oxide;
C. isothermal reaction 5 hours at 30 ℃ after being added dropwise to complete;
D. after reaction finishes, underpressure distillation, the Glacial acetic acid distilling out recycles;
E. be cooled to 25 ℃, in reaction vessel, add b acetone 89g crystallize out, suction filtration, dry, obtain white crystal N-acetyl-Beta-alanine 113g, yield is 87%, purity is 98.52%;
F. by the N-acetyl-Beta-alanine crystal 113g(0.86mol separating out) be that 65% nitric acid 1.29mol mixes with massfraction, stir, be heated to 30 ℃, isothermal reaction 5 hours;
G. isothermal reaction finishes, and underpressure distillation is cooled to 15 ℃, adds ethyl acetate 250mL crystallize out;
H. freeze overnight, filters, dry, can obtain N-acetyl-Beta-alanine nitrate finished product 151g, and yield is 78%, and purity is 98.67%;
I. the mother liquor that filters gained substitutes solvent and recycles.
Claims (6)
1. a synthetic method for N-acetyl-Beta-alanine nitrate, is characterized in that: comprise the steps:
A. Beta-alanine is added in reaction vessel, then add glacial acetic acid, stir;
While being b. heated to 30 ℃ ~ 90 ℃, in reaction vessel, drip acid anhydrides;
C. isothermal reaction 1 ~ 5 hour at 30 ℃ ~ 90 ℃ after being added dropwise to complete;
D. after reaction finishes, underpressure distillation, the Glacial acetic acid distilling out recycles;
E. be cooled to 5 ℃ ~ 25 ℃, in reaction vessel, add solvent crystallize out, be i.e. N-acetyl-Beta-alanine;
F. N-acetyl-Beta-alanine crystal of separating out is mixed with nitric acid, stir, be heated to 30 ℃ ~ 80 ℃, isothermal reaction 1 ~ 5 hour;
G. isothermal reaction finishes, and underpressure distillation is cooled to 5 ℃ ~ 15 ℃, adds solvent crystallize out;
H. freeze overnight, filters, dry, can obtain N-acetyl-Beta-alanine nitrate finished product;
I. the mother liquor that filters gained substitutes solvent and recycles.
2. the synthetic method of a kind of N-acetyl-Beta-alanine nitrate according to claim 1, is characterized in that: the glacial acetic acid adding in described step a and the mass ratio of Beta-alanine are 1 ~ 5:1.
The synthetic method of a kind of N-acetyl-Beta-alanine nitrate according to claim 1, is characterized in that: in described step b, acid anhydrides is diacetyl oxide.
3. the synthetic method of a kind of N-acetyl-Beta-alanine nitrate according to claim 1, is characterized in that: the acid anhydrides adding in described step b and the mol ratio of Beta-alanine are 0.95 ~ 2:1.
4. the synthetic method of a kind of N-acetyl-Beta-alanine nitrate according to claim 1, is characterized in that: the solvent in described step e, step g and step I is acetone or ethyl acetate.
5. the synthetic method of a kind of N-acetyl-Beta-alanine nitrate according to claim 1, is characterized in that: the solvent adding in described step e and step g and the mass ratio of Beta-alanine are 1 ~ 5:1.
6. the synthetic method of a kind of N-acetyl-Beta-alanine nitrate according to claim 1, is characterized in that: the mol ratio of the nitric acid adding in described step f and N-acetyl-Beta-alanine crystal is 1 ~ 1.5:1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105461632A (en) * | 2016-01-04 | 2016-04-06 | 湖北泓肽生物科技有限公司 | Preparing method for N-acetyl-L-carnosine |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB903431A (en) * | 1958-12-18 | 1962-08-15 | Hedley Thomas & Co Ltd | Process for producing acyl amides of amino acid salts |
| EP1314717A1 (en) * | 2001-11-26 | 2003-05-28 | Ajinomoto Co., Inc. | Method for preparing N-long chain acyl neutral amino acid |
| CN1569815A (en) * | 2004-04-29 | 2005-01-26 | 何佺 | Amino acid racemization method |
| CN101284798A (en) * | 2008-05-29 | 2008-10-15 | 重庆南松医药科技股份有限公司 | Environmental protection synthetic method of N-acetoglycocol |
| CN101723772A (en) * | 2009-11-27 | 2010-06-09 | 天津大学 | Method for preparing N-acetylamino acid |
-
2013
- 2013-12-16 CN CN201310685234.XA patent/CN103664679A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB903431A (en) * | 1958-12-18 | 1962-08-15 | Hedley Thomas & Co Ltd | Process for producing acyl amides of amino acid salts |
| EP1314717A1 (en) * | 2001-11-26 | 2003-05-28 | Ajinomoto Co., Inc. | Method for preparing N-long chain acyl neutral amino acid |
| CN1569815A (en) * | 2004-04-29 | 2005-01-26 | 何佺 | Amino acid racemization method |
| CN101284798A (en) * | 2008-05-29 | 2008-10-15 | 重庆南松医药科技股份有限公司 | Environmental protection synthetic method of N-acetoglycocol |
| CN101723772A (en) * | 2009-11-27 | 2010-06-09 | 天津大学 | Method for preparing N-acetylamino acid |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105461632A (en) * | 2016-01-04 | 2016-04-06 | 湖北泓肽生物科技有限公司 | Preparing method for N-acetyl-L-carnosine |
| CN105461632B (en) * | 2016-01-04 | 2018-01-09 | 湖北泓肽生物科技有限公司 | A kind of preparation method of N acetyl L carnosines |
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