CN106748871B - A kind of green circulatory industrial production process of amino acid surfactant - Google Patents
A kind of green circulatory industrial production process of amino acid surfactant Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of 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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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
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Abstract
The present invention discloses a kind of green circulatory industrial production process of amino acid surfactant, comprising the following steps: 1) fat acyl chloride and amino acid carry out amidation process；2) after amidation process, acidification layering obtains oil reservoir and the first waste water；3) add alkali to oil reservoir, obtain amino acid surfactant；4) pH in the first waste water is adjusted, the second waste water is obtained；5) then by the second waste water again by storng-acid cation exchange resin absorption, elution, recycling, amino acid and third waste water is obtained, amino acid recovery is entered step in 1)；6) desalting processing is carried out to third waste water again, obtains dissolution water；7) dissolution water flows into sour water recycling storage tank, enters back into step 1) and re-uses.Amino acid starting material high usage that preparation method of the invention obtains, product free acid are low, realize waste acid water recycled, save water, and do not generate pollution environment, and green environment is friendly.
Description
Technical field
The present invention relates to a kind of green circulatory industrial production process of amino acid surfactant, belong to fine chemical technology
Field.
Background technique
Surfactant is a kind of important functional fine chemicals, is widely used in each industrial department and field.
Amino acid surfactant be with mild anionic surfactant, it in addition to surfactant emulsification, wash
It washs, disperse, foaming, permeating, outside the basic performances such as solubilising, due to having amide group and amino acid structure in design feature, making
The advantages that obtaining more excellent low irritant, hypotoxicity, good biodegradability properties and compatibility preferable to human body, can use extensively
In fields such as detergent, cosmetics, medicine, food, biology, material, environmental protection, produced as people increasingly pay close attention to surfactant
Safety, mildness and the raising to environmental protection requirement of product, such surfactant will be increasingly by the weights of people
Depending on application field can be more and more extensive.
The synthetic method of amino acid surfactant mainly has chloride method, fatty acid anhydride method, Arneel SD Hydrolyze method, enzyme process
Deng, but the method industrially applied at present is chloride method, is reacted using Schotten-Baumann, acidification layering, is obtained
Oil reservoir-fat amic acid, then it is neutralized into salt, amino acid surfactant, the general blowdown of water layer can generate a large amount of useless
Acid, also content 5% or more amino-acid salts in waste acid water, portioned product is in order to improve acyl chlorides conversion ratio, using 1.1 equivalents
Amino acid, the COD in such waste acid water be even more considerably beyond water discharge standard, if but acyl chlorides it is excessive, and product middle reaches can be made
It is higher from acid content, influence products application；Furthermore it with the more and more extensive use of amino acid surfactant in recent years, gives up
The discharge of sour water be can bring serious environmental problem, if waste acid water directly as amidated solvent directly using again will lead to
The salt content of reaction is excessively high, so that reaction system is sticky, influences reaction conversion ratio.
Summary of the invention
For overcome the deficiencies in the prior art, the present invention provides a kind of amino acid surfactant green circulatory industry systems
Preparation Method, amino acid starting material high usage, the product free acid of the preparation method are low, realize waste acid water recycled, save and use
Water, does not generate pollution environment, and green environment is friendly.
Achieving the object of the present invention can be reached by adopting the following technical scheme that:
1) under alkaline condition, fat acyl chloride and amino acid carry out amidation process；
2) after amidation process, acidification layering, upper layer obtains oil reservoir, and lower layer obtains the first waste water；
3) oil reservoir is isolated, to oil reservoir plus alkali, neutralization obtains amino acid surfactant；
4) pH in the first waste water is adjusted, so that the pH of waste water is lower than the isoelectric point of amino acid, obtains the second waste water；
5) then by the second waste water again by storng-acid cation exchange resin absorption, elution, recycling, obtain amino acid and
Amino acid is recovered in recycling amino acid storage tank by third waste water, and the amino acid recycled in amino acid storage tank enters back into step 1)
Middle carry out amidation process；
6) desalting processing is carried out to third waste water again, third waste water obtains dissolution water after desalting processing；
7) dissolution water flows into sour water recycling storage tank, enters back into molten as amidating solvent and amino-acid salt in step 1)
Xie Shui is re-used.
Preferably, the molar ratio of fat acyl chloride and amino acid is 1:(1.2-2 in step 1)), the temperature of amidation process
It is 5-45 DEG C.
Preferably, the molar ratio of fat acyl chloride and amino acid is 1:(1.2-1.5 in step 1)), the temperature of amidation process
Degree is 5-35 DEG C.
Preferably, the amino acid in step 1) is sarcosine, glutamic acid, alanine, glycine, asparatate, silk
One of propylhomoserin.
Preferably, fatty acid in step 1) be oleic acid, linoleic acid, linolenic acid, isooctyl acid, isostearic acid, coconut oil,
One of palmitoleic acid, behenic acid, erucic acid；Alternatively, fatty acid carbon chain is C8-C18 or their arbitrary mixture.
Preferably, the storng-acid cation exchange resin in step 5) is the exchange of polystyrene macroporous type strong-acid cation
One of resin, polystyrene gel-type strong-acid cation-exchange resin.
Preferably, the flow velocity that the second waste water passes through storng-acid cation exchange resin in step 5) is 1-3L/min.
Preferably, the specific steps eluted in step 5) are as follows: the ammonium hydroxide that concentration is 0.1-1mol/L is added and is eluted.
Preferably, in step 6) desalting processing method be crystallisation by cooling desalination, electrodialysis, reverse osmosis, ion exchange,
One of multiple-effect evaporation or its any tandem compound method.
Preferably, further including step 8), step 8) between step 6) and step 7) specifically: dissolution is water-cooled to 5-20
DEG C, the inorganic salt crystal of precipitation is filtered, the salt content in filtrate is measured, deionized water is supplemented, so that the salt content in filtrate
Less than 5%.
Compared with prior art, the beneficial effects of the present invention are:
1, the amino acid starting material high usage of the green circulatory industrial production process of amino acid surfactant of the invention,
Product free acid is low, realizes waste acid water recycled, saves water, and does not generate pollution environment, and green environment is friendly；
2, the green circulatory industrial production process of amino acid surfactant of the invention is with fat acyl chloride, amino acid
Material synthesis propylhomoserin sodium class surfactant, prepares amino acid surfactant using Schotten-Baumann reaction, acidification
After generate waste acid water, sour water recycles unreacted amino acid using resin adsorption, after desalting processing, directly with being used further to
Acylation reaction, this method realize that amino acid starting material high usage, low free acid, waste acid water recycled do not generate pollution simultaneously
Environment is a kind of industrial production technology of cleaning green.
Detailed description of the invention
Fig. 1 is the flow chart of the green circulatory industrial production process of amino acid surfactant of the invention.
Specific embodiment
In the following, being described further in conjunction with attached drawing and specific embodiment to the present invention:
Embodiment 1
Initial reaction:
250kg Sodium Glycinate is added in 5000L reaction kettle, cocounut oil acyl chlorides is added dropwise in 2000kg water respectively under stiring
553Kg and 30% sodium hydroxide solution, keeping kettle interior reaction temperature is 10-15 DEG C, and pH value 8-11,3h material dropping finishes,
0.5h is kept the temperature at a temperature of this, reaction terminates, and phosphoric acid, layering is added, and upper layer obtains oil reservoir, and lower layer obtains the first waste water, oil
Water is added in layer, sodium hydroxide neutralizes, and obtains sodium cocoyl glycinate.
First waste water is adjusted into pH to 2.0, obtains the second waste water, the second waste water is passed through into activated polystyrene macropore
Type strong-acid cation-exchange resin, flow velocity 2L/min is complete to loading, is eluted with the ammonium hydroxide of 0.1moL/L, to appear
Amino acid detection signal starts to collect eluent, and gained eluent obtains amino acid and third waste water by concentration, admittedly contain
50%, it measures amino acid content (Sodium Glycinate containing 45kg, the rate of recovery 85%), amino acid enters recycling amino acid storage tank.Third
Waste water is cooled to 5 DEG C after polystyrene macroporous type strong-acid cation-exchange resin, filters away the inorganic salt crystal being precipitated
295kg (contains the crystallization water), measures salt content, supplements fresh water, so that salt content less than 5%, obtains dissolution water, dissolution water enters
Sour water recycles storage tank, is re-used as amidating solvent.
Circulation is realized:
The fresh glycine of 205kg is added in 5000L reaction kettle, 45kg recycles glycine (coming from amino acid storage tank),
2000 dissolution water (recycle storage tank from sour water), and acyl chlorides 553kg and 30% sodium hydroxide solution is added dropwise respectively under stiring, keeps
Kettle interior reaction temperature is 10-15 DEG C, and pH value 8-11,3h material dropping finishes, and keeps the temperature 0.5h at this temperature, and reaction terminates, and adds
Enter phosphoric acid, be layered, upper layer obtains oil reservoir, and lower layer obtains the first waste water, and water is added in oil reservoir, sodium hydroxide neutralizes, and obtains coconut palm
Oleoyl Sodium Glycinate, by HPLC, (ODS2C18 column, mobile phase: 85% methanol, flow: column temperature: 1mL/min 30 DEG C, is detected
Device: UV254nm) external standard method, measure free acid 6.5%.
First waste water is adjusted into pH to 2.0, obtains the second waste water, the second waste water is passed through into activated polystyrene macropore
Type strong-acid cation-exchange resin, flow velocity 2L/min is complete to loading, is eluted with the ammonium hydroxide of 0.1moL/L, to appear
Amino acid detection signal starts to collect eluent, and gained eluent obtains amino acid and third waste water by concentration, admittedly contain
50%, it measures amino acid content (Sodium Glycinate containing 46kg, the rate of recovery 86%), amino acid enters recycling amino acid storage tank.Third
Waste water is cooled to 5 DEG C after polystyrene macroporous type strong-acid cation-exchange resin, filters away the inorganic salt crystal being precipitated
310kg (contains the crystallization water), and filtrate measures salt content, supplements fresh water, so that salt content less than 5%, obtains dissolution water, dissolves water
Storage tank is recycled into sour water, is re-used as amidating solvent.
Embodiment 2
Initial reaction:
In 5000L reaction kettle be added 250kg Sodium L-alaninate, 2000kg water, under stiring respectively be added dropwise acyl chlorides 303Kg and
30% sodium hydroxide solution, keeping kettle interior reaction temperature is 36-40 DEG C, and pH value 8-11,2h material dropping finishes, at this temperature
1h is kept the temperature, reaction terminates, and phosphoric acid, layering is added, and upper layer obtains oil reservoir, and lower layer obtains the first waste water, and hydrogen-oxygen is added in oil reservoir
Change sodium to neutralize, obtains cocounut oil acyl Sodium L-alaninate.
First waste water is adjusted into pH to 2.0, obtains the second waste water, the second waste water is passed through into activated polystyrene macropore
Type strong-acid cation-exchange resin, flow velocity 1L/min is complete to loading, is eluted with the ammonium hydroxide of 0.15moL/L, to appear
Amino acid detection signal starts to collect eluent, and gained eluent obtains amino acid and third waste water by concentration, admittedly contain
50%, it measures amino acid content (Sodium L-alaninate containing 88kg, the rate of recovery 83%), amino acid enters recycling amino acid storage tank.Third
Waste water is cooled to 5 DEG C after polystyrene macroporous type strong-acid cation-exchange resin, filters away the inorganic salt crystal being precipitated
280kg (contains the crystallization water), and filtrate measures salt content, supplements fresh water, so that salt content less than 5%, obtains dissolution water, dissolves water
Storage tank is recycled into sour water, is re-used as amidating solvent.
Circulation is realized:
162kg Sodium L-alaninate is added in 5000L reaction kettle, 88kg recycles acid propyl (coming from amino acid storage tank),
2000kg water (recycles storage tank from sour water), and acyl chlorides 303kg and 30% sodium hydroxide solution is added dropwise respectively under stiring, keeps kettle
Interior reaction temperature is 5-35 DEG C, and pH value 8-11,2h material dropping finishes, and keeps the temperature 1h at this temperature, and reaction terminates, and phosphoric acid is added
Acidification, layering, upper layer obtain oil reservoir, and lower layer obtains the first waste water, and oil reservoir is added sodium hydroxide and neutralizes, and obtain cocounut oil acyl alanine
Sodium measures free acid 5.3% (measuring method is with embodiment 11).
First waste water is adjusted into pH to 2.0, obtains the second waste water, the second waste water is passed through into activated polystyrene macropore
Type strong-acid cation-exchange resin, flow velocity 1L/min is complete to loading, is eluted with the ammonium hydroxide of 0.2moL/L, to appear
Amino acid detection signal starts to collect eluent, and gained eluent obtains amino acid and third waste water by concentration, admittedly contain
50%, it measures amino acid content (Sodium L-alaninate containing 88kg, the rate of recovery 83%), amino acid enters recycling amino acid storage tank.Third
Waste water is cooled to 5 DEG C after polystyrene macroporous type strong-acid cation-exchange resin, filters away the inorganic salt crystal being precipitated
300kg (contains the crystallization water), and filtrate measures salt content, supplements fresh water, so that salt content less than 5%, obtains dissolution water, dissolves water
Storage tank is recycled into sour water, is re-used as amidating solvent.
Embodiment 3
Initial reaction:
In 5000L reaction kettle be added 250kg L-Serine sodium, 2000kg water, under stiring respectively be added dropwise acyl chlorides 238kg and
30% sodium hydroxide solution, keeping kettle interior reaction temperature is 40-45 DEG C, and pH value 8-11.5,3.5h material dropping finishes, warm herein
Degree is lower to keep the temperature 1h, and reaction terminates, and phosphoric acid, layering is added, and upper layer obtains oil reservoir, and lower layer obtains the first waste water, and oil reservoir is added
Sodium hydroxide neutralizes, and obtains cocounut oil acyl L-Serine sodium.
First waste water is adjusted into pH to 2.5, obtains the second waste water, the second waste water is passed through into activated polystyrene gel
Type strong-acid cation-exchange resin, flow velocity 3L/min is complete to loading, is eluted with the ammonium hydroxide of 1moL/L, ammonia to appear
Base acid detection signal starts to collect eluent, and gained eluent obtains amino acid and third waste water by concentration, admittedly contain 50%,
It measures amino acid content (L-Serine sodium containing 117kg, the rate of recovery 88%), amino acid enters recycling amino acid storage tank.Third waste water
After polystyrene gel-type strong-acid cation-exchange resin, 5 DEG C are cooled to, filters away the inorganic salt crystal being precipitated
249kg (contains the crystallization water), and filtrate measures salt content, supplements fresh water, so that salt content less than 5%, obtains dissolution water, dissolves water
Storage tank is recycled into sour water, is re-used as amidating solvent.
Circulation is realized:
133kg L-Serine sodium is added in 5000L reaction kettle, 117kg recycles L-Serine sodium (coming from amino acid storage tank),
2000kg water (recycles storage tank from sour water), and acyl chlorides 238kg and 30% sodium hydroxide solution is added dropwise respectively under stiring, keeps kettle
Interior reaction temperature is 40-45 DEG C, and pH value 8-11.5,3.5h material dropping finishes, and keeps the temperature 1h at this temperature, and reaction terminates, and adds
Enter phosphoric acid, be layered, upper layer obtains oil reservoir, and lower layer obtains the first waste water, and oil reservoir is added sodium hydroxide and neutralizes, and obtains cocounut oil acyl
L-Serine sodium.It measures free acid 7.3% (measuring method is with example 1)
First waste water is adjusted into pH to 2.0, obtains the second waste water, the second waste water is passed through into activated polystyrene gel
Type strong-acid cation-exchange resin, flow velocity 3L/min is complete to loading, is eluted with the ammonium hydroxide of 1moL/L, ammonia to appear
Base acid detection signal starts to collect eluent, and gained eluent obtains amino acid and third waste water by concentration, admittedly contain 50%,
It measures amino acid content (L-Serine sodium containing 113kg, the rate of recovery 85%), amino acid enters recycling amino acid storage tank.Third waste water
After polystyrene gel-type strong-acid cation-exchange resin, 5 DEG C are cooled to, filters away the inorganic salt crystal being precipitated
290kg (contains the crystallization water), and filtrate measures salt content, supplements fresh water, so that salt content less than 5%, obtains dissolution water, dissolves water
Storage tank is recycled into sour water, is re-used as amidating solvent.
For those skilled in the art, it can make other each according to the above description of the technical scheme and ideas
Kind is corresponding to be changed and deforms, and all these change and deform the protection model that all should belong to the claims in the present invention
Within enclosing.
Claims (6)
1. a kind of cycle industrial preparation method of amino acid surfactant, which comprises the following steps:
1) under alkaline condition, fat acyl chloride and amino acid carry out amidation process, and the molar ratio of fat acyl chloride and amino acid is
1:(1.2-2), the temperature of amidation process is 5-45 DEG C；Wherein, amino acid be sarcosine, glutamic acid, alanine, glycine,
One of asparatate, serine；Fatty acid be oleic acid, linoleic acid, linolenic acid, isooctyl acid, isostearic acid, coconut oil,
One of palmitoleic acid, behenic acid, erucic acid or their arbitrary mixture；
2) after amidation process, acidification layering, upper layer obtains oil reservoir, and lower layer obtains the first waste water；
3) oil reservoir is isolated, to oil reservoir plus alkali, neutralization obtains amino acid surfactant；
4) pH in the first waste water is adjusted, so that the pH of waste water is lower than the isoelectric point of amino acid, obtains the second waste water；
5) then by the second waste water again by storng-acid cation exchange resin absorption, elution, recycling, amino acid and third are obtained
Waste water, by amino acid be recovered to recycling amino acid storage tank in, recycle amino acid storage tank in amino acid enter back into step 1) into
Row amidation process；
6) desalting processing is carried out to third waste water again, third waste water obtains dissolution water after desalting processing；
7) dissolution is water-cooled to 5-20 DEG C, and the inorganic salt crystal of precipitation is filtered, and measures the salt content in filtrate, supplements deionization
Water, so that the salt content in filtrate is less than 5%；
8) dissolution water flows into sour water recycling storage tank, enters back into step 1) as amidating solvent and amino-acid salt dissolution water
It re-uses.
2. the cycle industrial preparation method of amino acid surfactant according to claim 1, which is characterized in that step 1)
The molar ratio of middle fat acyl chloride and amino acid is 1:(1.2-1.5), the temperature of amidation process is 5-35 DEG C.
3. the cycle industrial preparation method of amino acid surfactant according to claim 1, which is characterized in that step 5)
In storng-acid cation exchange resin be polystyrene macroporous type strong-acid cation-exchange resin, polystyrene gel-type strong acid
One of cation exchange resin.
4. the cycle industrial preparation method of amino acid surfactant according to claim 1, which is characterized in that step 5)
In the second waste water by the flow velocity of storng-acid cation exchange resin be 1-3L/min.
5. the cycle industrial preparation method of amino acid surfactant according to claim 1, which is characterized in that step 5)
The specific steps of middle elution are as follows: the ammonium hydroxide that concentration is 0.1-1mol/L is added and is eluted.
6. the cycle industrial preparation method of amino acid surfactant according to claim 1, which is characterized in that step 6)
The method of middle desalting processing be one of crystallisation by cooling desalination, electrodialysis, reverse osmosis, ion exchange, multiple-effect evaporation or its
Meaning tandem compound method.
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| CN114713152A (en) * | 2022-04-01 | 2022-07-08 | 岳阳科罗德联合化学工业有限公司 | Production system and preparation method for producing salt-free amino acid surfactant by continuous flow |
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