CN107353223A - A kind of manufacture craft of fatty acid acylamino acid - Google Patents
A kind of manufacture craft of fatty acid acylamino acid Download PDFInfo
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- CN107353223A CN107353223A CN201710750248.3A CN201710750248A CN107353223A CN 107353223 A CN107353223 A CN 107353223A CN 201710750248 A CN201710750248 A CN 201710750248A CN 107353223 A CN107353223 A CN 107353223A
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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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of manufacture craft of fatty acid acylamino acid, its innovative point is：Using fatty acid methyl ester and amino acid sodium as raw material, in the presence of metal oxide catalyst, using one-step synthesis, N fatty acid acylamino acid natrium surfactants are synthesized, the mol ratio of the raw fatty acid methyl esters and amino acid sodium is 1.2~1.8：0.7~1.Ratio is suitable between raw material, is produced substantially without accessory substance, and Product formation rate is up to more than 87%, and purity is high, overcomes and the problems such as a large amount of spent acid need processing, operating procedure is complicated, raw material PCl3 excitants are big is produced in traditional chloride method, meet Green Chemistry principle.Catalyst amount is reasonable, utilizes the catalyst so that production efficiency is substantially increased in preparation process, production procedure is shortened, and is improved product quality, and good product even can be directly used for making pharmaceuticals industry raw material.
Description
Technical field
The present invention relates to a kind of manufacture craft of fatty acid acylamino acid, belong to organic compound synthesis technical field.
Background technology
In recent years, with the idea of sustainable development deeply and human environment protection realize enhancing, part corrosion inhibiter by
It is big in its toxicity, the reason such as biodegradability difference, it can have become increasingly limited when in use, therefore, research and development are high
Effect, less toxic, environment-friendly corrosion inhibiter are a urgent problems.Amino acids have wide material sources, it is nontoxic,
The characteristics of degradable, it has also become the important directions of corrosion inhibiter research and development.
With the fast development of science and technology, research, production and the application of surfactant deepen continuously and expanded, new
Surfactant constantly comes out.Amino acid surfactant is mainly the N- acylamino acids synthesized by amino acid with aliphatic acid
The surfactant of series.Due to the surfactant that amino acid type surfactant belongs to based on biological substance, except
Outside with excellent surface property, preservative is also used as, and there is preferable antibacterial, antiviral property.Therefore to ammonia
Base acid series of surfactants, which carries out research and development tool, to have very important significance.
At present, the synthetic method of N- fatty acid acylamino acids series of surfactants has chloride method, fatty acid anhydride method, fat
Fat nitrile Hydrolyze method, amide carbonylation method, enzyme process etc..Fatty acid anhydride method, Arneel SD Hydrolyze method, amide carbonylation method, enzyme process this four
Although kind of method proposition is more early, industrial application is not obtained for various reasons.Wherein, most commonly chloride method synthesizes
Method, first the bromo aliphatic acid of different chain length is esterified in its synthesis, to prevent in etherification procedure of the next step with phenol it
Itself react generation accessory substance.Then the phenol of the bromo fatty acid ester of different chain length and different substituents is etherified,
Then it is hydrolyzed and prepares a series of aliphatic acid with different rigidity structure and chain length.It is anti-by Schotten-Baumann again
N- acylamino acids should be prepared.Synthesized compound passes through HNMR, the checking such as MS, IR.In the N- acylation process of amino acid
In, by attempting different experiment conditions, more satisfactory synthetic route is finally determined：Using water and THF mixed solvent methods：
By the way of acyl chlorides is added dropwise, so as to allow the acyl chlorides that is just added dropwise can fully, in time with amino acid reaction, avoid acyl chlorides as far as possible
The side reaction such as hydrolysis；Reaction temperature will be controlled in zero degree or so.Simultaneously in order to avoid the hydrolysis of acyl chlorides as far as possible, by dripping simultaneously
Add the mode of the 10%KOH aqueous solution, maintenance reaction liquid pH value is 10 or so.
But the method subject matter is using having severe corrosive and irritating raw material in synthesis, in condensation to acyl chlorides quality
It is it is required that very high, it is necessary to completely cut off moisture storage, to reduce its hydrolysis, after otherwise hydrolysate introduces product, removing is extremely difficult, and
And there are other more accessory substances, product color difference and have the shortcomings that peculiar smell.
The content of the invention
It is an object of the invention to for deficiency of the prior art, there is provided a kind of making work of fatty acid acylamino acid
Skill, ratio is suitable between raw material, is produced substantially without accessory substance, and Product formation rate is up to more than 87%, and purity is high, overcomes biography
The problem of in system chloride method, meet Green Chemistry principle.
In order to solve the above technical problems, the technical solution adopted by the present invention is：A kind of making work of fatty acid acylamino acid
Skill, its innovative point are：Using fatty acid methyl ester and amino acid sodium as raw material, in the presence of metal oxide catalyst, use
One-step synthesis, synthesis N- fatty acid acylamino acid natrium surfactants, the raw fatty acid methyl esters and amino acid sodium are rubbed
You are than being 1.2~1.8：0.7~1.
Further, the metal oxide catalyst is the mixture of potassium oxide and magnesia, potassium oxide and magnesia
Mixing molar ratio be 1~2：1.
Further, the addition of the catalyst is 0.05~0.08wt% of reaction-ure mixture.
Further, the one-step synthesis concretely comprise the following steps by amino acid sodium from amino acid sodium storage tank be continuously introduced into by
In the mixed reactor that firsts and seconds blender is composed in series, fatty acid methyl ester is continuously added according to the raw material ratio of proportional quantity
Enter in firsts and seconds blender, after reaction mass is first heated to 20~40 degree in a mixer, add the metal oxygen of proportional quantity
Compound catalyst, hybrid reaction is finally carried out, the reaction time is 2~4h.
Further, the reaction temperature of the one-level blender is controlled between 20~30 degree, the reaction of secondary mixer
Temperature control is between 30~40 degree.
Further, one-level blender inlet temperature control is at 20~25 degree, one-level blender discharging opening temperature
Control is at 25~30 degree.
Further, secondary mixer inlet temperature control is at 30~35 degree, secondary mixer discharging opening temperature
Control is at 35~40 degree.
Further, the pH values in the one-level blender maintain 8~10；PH values in secondary mixer maintain
10~13.
Advantages of the present invention：
（1）The method for preparing fatty acid acylamino acid class compound of the present invention, using fatty acid methyl ester and amino acid sodium as raw material,
In the presence of metal oxide catalyst, using one-step synthesis, the mol ratio of raw fatty acid methyl esters and amino acid sodium is
1.2~1.8：0.7~1, ratio is suitable between raw material, is produced substantially without accessory substance, and Product formation rate is up to more than 87%, pure
Degree is high, overcomes and produces that a large amount of spent acid need processing, operating procedure is complicated, raw material PCl3 excitants are big in traditional chloride method etc. and ask
Topic, meets Green Chemistry principle.
（2）The method for preparing fatty acid acylamino acid class compound of the present invention, metal oxide catalyst is from oxidation
The mixture of potassium and magnesia, and the control of the mixing molar ratio of potassium oxide and magnesia is 1~2：1, the addition of catalyst
For 0.05~0.08wt% of reaction-ure mixture, catalyst amount is reasonable, utilizes the catalyst so that carried significantly in preparation process
High production efficiency, production procedure is shortened, and is improved product quality, and good product even can be directly used for making pharmacy
The raw material of industry.
（3）The method for preparing fatty acid acylamino acid class compound of the present invention, concretely comprising the following steps for one-step synthesis will
Amino acid sodium is continuously introduced into the mixed reactor being composed in series by firsts and seconds blender from amino acid sodium storage tank, according to
Fatty acid methyl ester is continuously added in firsts and seconds blender by the raw material ratio of proportional quantity, and reaction mass is first heated to 20~40 degree
Afterwards, the metal oxide catalyst of proportional quantity is added, finally carries out hybrid reaction, whole course of reaction is simple and reliable, reacts bar
Part parameter is gently easy to control, and the safe of product, mildness are good.
（4）The method for preparing fatty acid acylamino acid class compound of the present invention, the reaction temperature control of one-level blender
Between 20~30 degree, the reaction temperature of secondary mixer is controlled between 30~40 degree, specifically, one-level blender charging aperture
Temperature control is at 20~25 degree, and one-level blender discharging opening temperature control is at 25~30 degree；Secondary mixer inlet temperature control
System is at 30~35 degree, and secondary mixer discharging opening temperature control is at 35~40 degree, the strict reaction temperature controlled in blender, especially
It is the temperature of charging aperture and discharging opening, can effectively reduce accessory substance generation, and it is preferable make it that reacted product has
Surface-active and excellent foaming foam stability energy.
（5）The method for preparing fatty acid acylamino acid class compound of the present invention, it is also noted that by the pH in one-level blender
Value maintains 8~10；PH values in secondary mixer maintain 10~13, effectively control the reaction solution table in course of reaction
The size of face tension force, excellent prerequisite is provided for the outstanding performance of product.
Embodiment
Technical scheme is elaborated with reference to specific embodiment.
Embodiment 1
The mol ratio for selecting raw material methyl laurate and Sodium Glycinate is 1.2：0.7, to mix molar ratio as 1：1 potassium oxide
Mixture with magnesia is metal oxide catalyst, and the addition of catalyst is the 0.05wt% of reaction-ure mixture.
One-step synthesis is synthetically prepared：Sodium Glycinate is continuously introduced into by firsts and seconds blender from Sodium Glycinate storage tank
In the mixed reactor being composed in series, methyl laurate is continuously added to firsts and seconds according to the raw material ratio of proportional quantity and mixed
In device, after reaction mass is first heated to 20~40 degree in a mixer, the metal oxide catalyst of proportional quantity is added, it is most laggard
Row hybrid reaction, reaction time 3h.
Wherein, the reaction temperature overall control of one-level blender is between 20~30 degree, specifically, one-level blender is fed
Mouth temperature control is at 20 degree, and one-level blender discharging opening temperature control is at 30 degree；PH values maintain 8.The reaction of secondary mixer
Temperature overall control is between 30~40 degree, specifically, the control of secondary mixer inlet temperature, at 30 degree, secondary mixer goes out
Material mouth temperature control is at 40 degree；PH values maintain 13.
After reaction terminates, after isolating 0.083% methanol, the lauroyl glycine of active matter content 94.56% is obtained
Sodium, purity is up to 98%.
Embodiment 2
The mol ratio for selecting raw material methyl laurate and Sodium L-alaninate is 1.2：0.7, to mix molar ratio as 1：1 potassium oxide
Mixture with magnesia is metal oxide catalyst, and the addition of catalyst is the 0.08wt% of reaction-ure mixture.
It is synthetically prepared according to the one-step synthesis in embodiment 1, wherein, the reaction temperature overall control of one-level blender exists
Between 20~30 degree, specifically, the control of one-level blender inlet temperature, at 20 degree, one-level blender discharging opening temperature control exists
25 degree；PH values maintain 10.The reaction temperature overall control of secondary mixer is between 30~40 degree, specifically, two level mixes
Device inlet temperature is controlled at 30 degree, and secondary mixer discharging opening temperature control is at 35 degree；PH values maintain 10.
After reaction terminates, after isolating 0.078% methanol, the lauroyl alanine of active matter content 90.33% is obtained
Sodium, purity is up to 98%.
Embodiment 3
The mol ratio for selecting raw material methyl laurate and sodium glutamate is 1.8：0.7, to mix molar ratio as 2：1 potassium oxide
Mixture with magnesia is metal oxide catalyst, and the addition of catalyst is the 0.05wt% of reaction-ure mixture.
It is synthetically prepared according to the one-step synthesis in embodiment 1, wherein, the reaction temperature overall control of one-level blender exists
Between 20~30 degree, specifically, the control of one-level blender inlet temperature, at 25 degree, one-level blender discharging opening temperature control exists
25 degree；PH values maintain 10.The reaction temperature overall control of secondary mixer is between 30~40 degree, specifically, two level mixes
Device inlet temperature controls 35 degree, and secondary mixer discharging opening temperature control is at 35 degree；PH values maintain 13.
After reaction terminates, after isolating 0.069% methanol, the lauroyl glutamate of active matter content 88.67% is obtained
Sodium, purity is up to 98%.
Embodiment 4
The mol ratio for selecting raw material methyl hexadecanoate and sodium glutamate is 1.8：1, to mix molar ratio as 2：1 potassium oxide and
The mixture of magnesia is metal oxide catalyst, and the addition of catalyst is the 0.08wt% of reaction-ure mixture.
It is synthetically prepared according to the one-step synthesis in embodiment 1, wherein, the reaction temperature overall control of one-level blender exists
Between 20~30 degree, specifically, the control of one-level blender inlet temperature, at 25 degree, one-level blender discharging opening temperature control exists
30 degree；PH values maintain 9.The reaction temperature overall control of secondary mixer is between 30~40 degree, specifically, two level mixes
Device inlet temperature is controlled at 35 degree, and secondary mixer discharging opening temperature control is at 40 degree；PH values maintain 12.
After reaction terminates, after isolating 0.085% methanol, the palmityl glutamic acid of active matter content 90.56% is obtained
Sodium, purity is up to 98%.
Claims (8)
- A kind of 1. manufacture craft of fatty acid acylamino acid, it is characterised in that：Using fatty acid methyl ester and amino acid sodium as raw material, In the presence of metal oxide catalyst, using one-step synthesis, N- fatty acid acylamino acid natrium surfactants are synthesized, it is described The mol ratio of raw fatty acid methyl esters and amino acid sodium is 1.2~1.8：0.7~1.
- 2. the method according to claim 1 for preparing fatty acid acylamino acid class compound, it is characterised in that：The metal Oxide catalyst is the mixture of potassium oxide and magnesia, and the mixing molar ratio of potassium oxide and magnesia is 1~2：1.
- 3. the method according to claim 1 or 2 for preparing fatty acid acylamino acid class compound, it is characterised in that：It is described The addition of catalyst is 0.05~0.08wt% of reaction-ure mixture.
- 4. the method according to claim 1 for preparing fatty acid acylamino acid class compound, it is characterised in that：One step The concretely comprising the following steps amino acid sodium being continuously introduced into from amino acid sodium storage tank of synthetic method is composed in series by firsts and seconds blender Mixed reactor in, fatty acid methyl ester is continuously added in firsts and seconds blender according to the raw material ratio of proportional quantity, instead After answering material to be first heated to 20~40 degree in a mixer, the metal oxide catalyst of proportional quantity is added, is finally mixed Reaction, the reaction time is 2~4h.
- 5. the method according to claim 4 for preparing fatty acid acylamino acid class compound, it is characterised in that：The one-level The reaction temperature of blender is controlled between 20~30 degree, and the reaction temperature of secondary mixer is controlled between 30~40 degree.
- 6. the method according to claim 4 for preparing fatty acid acylamino acid class compound, it is characterised in that：The one-level Blender inlet temperature is controlled at 20~25 degree, and one-level blender discharging opening temperature control is at 25~30 degree.
- 7. the method according to claim 4 for preparing fatty acid acylamino acid class compound, it is characterised in that：The two level Blender inlet temperature is controlled at 30~35 degree, and secondary mixer discharging opening temperature control is at 35~40 degree.
- 8. the method according to claim 4 for preparing fatty acid acylamino acid class compound, it is characterised in that：The one-level PH values in blender maintain 8~10；PH values in secondary mixer maintain 10~13.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710750248.3A CN107353223A (en) | 2017-08-28 | 2017-08-28 | A kind of manufacture craft of fatty acid acylamino acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710750248.3A CN107353223A (en) | 2017-08-28 | 2017-08-28 | A kind of manufacture craft of fatty acid acylamino acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107353223A true CN107353223A (en) | 2017-11-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710750248.3A Withdrawn CN107353223A (en) | 2017-08-28 | 2017-08-28 | A kind of manufacture craft of fatty acid acylamino acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107353223A (en) |
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2017
- 2017-08-28 CN CN201710750248.3A patent/CN107353223A/en not_active Withdrawn
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Application publication date: 20171117 |
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| WW01 | Invention patent application withdrawn after publication |