CN108912008A - A method of N- fatty acid acylamino acid amide is prepared by fatty acid methyl ester - Google Patents
A method of N- fatty acid acylamino acid amide is prepared by fatty acid methyl ester Download PDFInfo
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- CN108912008A CN108912008A CN201810647899.4A CN201810647899A CN108912008A CN 108912008 A CN108912008 A CN 108912008A CN 201810647899 A CN201810647899 A CN 201810647899A CN 108912008 A CN108912008 A CN 108912008A
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- fatty acid
- amide
- amino acid
- acid
- methyl ester
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
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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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of methods that fatty acid methyl ester prepares N- fatty acid acylamino acid amide.This method is to react to obtain amide with amine after amino acid alkalizes, and then amide reacts to obtain N- fatty acid acylamino acid amide with the fatty acid methyl ester of alkalization.N- fatty acid acylamino acid amide Method provided by the invention, preparation is simple, and step is few, and it is not necessary that boride catalyst, organic solvent and cosolvent etc. is added, and purification of products is easy and high income.
Description
Technical field
A kind of preparation method of N- fatty acid acylamino acid amide, specifically with fatty acid methyl ester, amino acid and amine
For the preparation method of Material synthesis N- fatty acid acylamino acid amide, belong to technical field of fine.
Background technique
N- fatty acid acylamino acid amide is the derivative of N- fatty acid acylamino acid surfactant, special because having
Property is applied to the multiple fields such as processing oil spilling, oily waste water, liquid explosives, medicine and household chemicals, can be used as antioxygen
Agent, antibacterial agent, cosmetic additive agent and antistatic agent, especially its gelling properties are increasingly paid close attention to by industry in recent years.
The preparation method of N- fatty acid acylamino acid amide, currently used is that N- fatty acid acylamino acid is reacted with amine,
There are two types of modes for its reaction：First is that heating N- fatty acid acylamino acid together with amine under dehydration conditions, acyl is directly formed
Amine；Another kind is the active carboxylic acid derivative that the carboxyl in N- fatty acid acylamino acid is changed into high reaction, be such as changed into carboxylic acid halides,
Then ester or acid anhydrides react resulting derivative with amine, carboxyl is changed into the method for the active carboxylic acid derivative of high reaction.Two
Kind method has drawback, and first method Direct Dehydration needs higher temperature or water entrainer is added, and often because of temperature mistake
Height keeps by-product more and influences yield, and second method reaction step is more, cumbersome, and needs more excess amine anti-
It answers.
A kind of method for producing N- fatty acid acylamino acid amine has been invented by Japanese Ajincomoto Co., Inc, i.e., in N- fatty acyl
When base amino acid is reacted with amine, catalyst boron compound and cosolvent alcohol is added, keeps reaction yield high, the reaction time is short, but closes
At when catalyst, cosolvent and dehydrating agent etc. is added.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of N- fatty acid acylamino acid amide, this N-
Fatty acid acylamino acid amide preparation method first reacts amino acid with amine to obtain amide, and then amide and fatty acid methyl ester are anti-
N- fatty acid acylamino acid amide should be obtained, preparation is simple, and step is few, it is not necessary that catalyst and organic solvent is added, and produces
Produce rate is up to 76-95%.
The present invention provides the preparation method of N- fatty acid acylamino acid amide, reaction route is as follows：(1) by amino acid
It reacts to obtain amide with amine after alkalization；(2) after alkali and fatty acid methyl ester reaction are added in the amide after separating-purifying, separation is mentioned
It is pure to obtain N- fatty acid acylamino acid amide.
Specific step is as follows for the preparation method of the amide of fatty acid acylamino acid containing N- of the invention：Amino acid is put into reaction
In device, be added dropwise amine after stirring under alkaline condition, reaction temperature is 50-250 DEG C, preferably 70-150 DEG C, wherein amino acid with
The molar ratio of amine is 0.5-1: 1-3, preferably 1: 1-2, and the molar ratio of alkali and amino acid is 0.5-3: 1-3, preferably 1-2: 1,
Reaction 2-15 hours, preferably 4-10 hours, after the reaction was completed, separating-purifying obtained amide.Then fat is added in amide
Sour methyl esters and lye, reaction generates N- fatty acid acylamino acid amide under alkaline condition, and reaction temperature is 40-200 DEG C, best
It is to be reacted at 60-150 DEG C, the molar ratio of amide and grease is 0.5-2: 1-3, preferably 1: 1-2, and the molar ratio of alkali and grease is
0.5-4: 1-2, preferably 1-2: 1, it reacts 2-20 hours, preferably 3-8 hours, then separating-purifying obtained target product, received
Rate is 70-90%.
Alkali as described above can be NaOH, KOH or Na2CO3Or any one in sodium methoxide.
Amino acid as described above can be any acidic amino acid, neutral amino acid or basic amino acid, be also possible to
Any a-amino acid, beta-amino acids and gamma-amino acid, such as alanine, valine, phenylalanine, arginine, histidine, paddy ammonia
Acid, lysine, aspartic acid, tryptophan, serine etc..
Amine as described above can be straight chain, branch, saturation, unsaturated primary amine or the secondary amine of any 1-40 carbon atom,
Such as methylamine, ethamine, propylamine, butylamine, octylame, decyl amine, lauryl amine, stearylamine, benzene methanamine, cyclohexylamine, aniline, dilaurylamine (DLA).
Fatty acid methyl ester as described above can be the fatty acid methyl ester for various natural oil sources or the fat of synthesis
Dialkylaminobenzoic acid carbon number is the fatty acid methyl ester of 2-25, such as coconut oil fatty acid methyl ester, palm kernel fatty acid methyl esters, palm oil fat
Sour methyl esters, cottonseed oil fatty acid methyl esters, olive soyate, Rice oil methyl esters, rapeseed oil fatty acid methyl esters, soybean grease
Fatty acid methyl esters, corn oil fatty acid methyl esters, peanut oil fatty acid methyl esters, tallow acid methyl esters, hydrogenated tallow methyl esters,
Lard fatty acid methyl ester, methyl laurate, methyl oleate, methyl myristate, methyl caprate, methyl stearate etc..
The preparation method of N- fatty acid acylamino acid amide of the invention, with the preparation N- fatty acid acylamino acid that there is now
Amide Method comparison, effect is positive and apparent.Its advantage is that the use of fatty acid methyl ester, amino acid and amine being raw material, rouge
Fatty acid methyl esters are handled without carboxylic acid halides or acid anhydridesization, reduce reaction step, and it is not necessary that boride catalyst, organic solvent is added
With cosolvent alcohol etc., purification of products is easy and high income.
Specific embodiment
It makes an explanation below with reference to embodiment to the present invention.
Embodiment 1
45g lysine is put into reactor, decyl amine is added dropwise after 30% sodium hydrate aqueous solution 39.21g stirring is added
58.11g, reaction temperature are 90 DEG C, are reacted 5 hours, after the reaction was completed, separating-purifying obtains 82.61g amide.Then in amide
The middle sodium hydrate aqueous solution that 93.90g methyl hexadecanoate is added and 47.64g 30% is added, reacts 5 hours at 140 DEG C, point
140.09g N- palmityl lysine acyl group decyl amine is obtained from purification.
Embodiment 2
30g glutamic acid is put into reactor, octylame is added dropwise after 30% sodium hydrate aqueous solution 26g stirring is added
31.65g, reaction temperature are 80 DEG C, are reacted 5 hours, after the reaction was completed, separating-purifying obtains 51.78g amide.Then in amide
The middle sodium hydrate aqueous solution that 51.56g methyl laurate is added and 33.20g 30% is added, reacts 7 hours at 135 DEG C, point
82.10g N- lauroyl glutamate acyl group octylame is obtained from purification.
Embodiment 3
50g histidine is put into reactor, cyclohexylamine is added dropwise after 30% sodium hydrate aqueous solution 41.10g stirring is added
38.39g, reaction temperature are 75 DEG C, are reacted 5 hours, after the reaction was completed, separating-purifying obtains 71.61g amide.Then in amide
The middle sodium hydrate aqueous solution that 108.62g methyl stearate is added and 49.92g 30% is added, reacts 6 hours at 140 DEG C,
Separating-purifying obtains 141.01g N- stearyl histidine acyl group cyclohexylamine.
Embodiment 4
50g tryptophan is put into reactor, propylamine is added dropwise after 30% sodium hydrate aqueous solution 31.19g stirring is added
17.34g, reaction temperature are 90 DEG C, are reacted 6 hours, after the reaction was completed, separating-purifying obtains 57.06g amide.Then in amide
The middle sodium hydrate aqueous solution that 230.55g peanut oil fatty acid methyl esters is added and 38.30g 30% is added, reacts 6 at 145 DEG C
Hour, separating-purifying obtains 220.50g N- peanut oleoyl tryptophan acyl group propylamine.
Embodiment 5
60g serine is put into reactor, aniline is added dropwise after 30% sodium hydrate aqueous solution 72.74g stirring is added
63.81g, reaction temperature are 90 DEG C, are reacted 5 hours, after the reaction was completed, separating-purifying obtains 97.76g amide.Then in amide
The middle sodium hydrate aqueous solution that 528.51g methyl soyate is added and 89.30g 30% is added, reacts 7 at 130 DEG C
Hour, separating-purifying obtains 475.58g N- soybean oleoyl serine anilid.
Claims (7)
1. a kind of method that fatty acid methyl ester prepares N- fatty acid acylamino acid amide, it is characterised in that reaction route is as follows：
(1) it reacts to obtain amide with amine after amino acid alkalizing；
(2) after alkali and fatty acid methyl ester reaction are added in the amide after separating-purifying, purification & isolation obtains N- fatty acyl group ammonia
Base acid amide.
2. according to the method described in claim 1, it is characterized in that the amino acid is any acidic amino acid, neutral amino
Acid or basic amino acid, are also possible to any a-amino acid, beta-amino acids and gamma-amino acid.
3. according to the method described in claim 1, it is characterized in that the amine is the straight chain of any 1-40 carbon atom, branch
Chain, saturation, unsaturated primary amine or secondary amine.
4. according to the method described in claim 1, it is characterized in that the alkali is NaOH, KOH or Na2CO3Or methanol
Any one in sodium.
5. according to the method described in claim 1, it is characterized in that fatty acid methyl ester is the fatty acid in various natural oil sources
The fatty acid methyl ester that methyl esters or the fatty acid alkyl carbon number of synthesis are 2-25.
6. according to the method described in claim 1, amino acid and amine rub it is characterized in that (1) reaction temperature is 50-250 DEG C
, than being 0.5-1: 1-3, the molar ratio of alkali and amino acid is 0.5-3: 1-3 for you, is reacted 2-15 hours.
7. according to the method described in claim 1, amide and grease rub it is characterized in that (2) reaction temperature is 40-200 DEG C
, than being 0.5-2: 1-3, the molar ratio of alkali and grease is 0.5-4: 1-2 for you, is reacted 2-20 hours.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810647899.4A CN108912008A (en) | 2018-06-22 | 2018-06-22 | A method of N- fatty acid acylamino acid amide is prepared by fatty acid methyl ester |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810647899.4A CN108912008A (en) | 2018-06-22 | 2018-06-22 | A method of N- fatty acid acylamino acid amide is prepared by fatty acid methyl ester |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1294121A (en) * | 1999-10-20 | 2001-05-09 | 味之素株式会社 | N-acyl amino-acid amide prodn. process |
| CN101597247A (en) * | 2008-06-06 | 2009-12-09 | 中国科学院成都生物研究所 | N-sulfinyl amino acid amide compound and application thereof |
| CN102311359A (en) * | 2011-06-16 | 2012-01-11 | 北京工商大学 | Method for preparing N-fatty acyl amino acid surfactant from methyl ester |
| CN104693061A (en) * | 2015-03-26 | 2015-06-10 | 南通市明建生物科技有限公司 | Method for preparing N-fatty acyl group amino acid compound |
-
2018
- 2018-06-22 CN CN201810647899.4A patent/CN108912008A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1294121A (en) * | 1999-10-20 | 2001-05-09 | 味之素株式会社 | N-acyl amino-acid amide prodn. process |
| CN101597247A (en) * | 2008-06-06 | 2009-12-09 | 中国科学院成都生物研究所 | N-sulfinyl amino acid amide compound and application thereof |
| CN102311359A (en) * | 2011-06-16 | 2012-01-11 | 北京工商大学 | Method for preparing N-fatty acyl amino acid surfactant from methyl ester |
| CN104693061A (en) * | 2015-03-26 | 2015-06-10 | 南通市明建生物科技有限公司 | Method for preparing N-fatty acyl group amino acid compound |
Non-Patent Citations (5)
| Title |
|---|
| RACHEL M. LANIGAN，等: "Direct amidation of unprotected amino acids using B(OCH2CF3)3", 《CHEM.COMMUN.,》 * |
| 刘军 等: "《有机化学（第2版）》", 31 August 2014, 武汉理工大学出版社 * |
| 唐婷婷: "油脂酰肌氨酸类表面活性剂的设计、合成与性能研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
| 姚其正 等: "《药物合成反应》", 1 September 2012, 中国医药科技出版社 * |
| 徐宝财 等: "酰基氨基酸型表面活性剂", 《2006（第九届）国际表面活性剂/洗涤剂会议》 * |
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