CN106748871A - 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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- CN106748871A CN106748871A CN201611072368.4A CN201611072368A CN106748871A CN 106748871 A CN106748871 A CN 106748871A CN 201611072368 A CN201611072368 A CN 201611072368A CN 106748871 A CN106748871 A CN 106748871A
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
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- C07C231/24—Separation; Purification
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Abstract
The present invention discloses a kind of green circulatory industrial production process of amino acid surfactant, comprises the following steps：1) fat acyl chloride and amino acid carry out amidation process；2) after amidation process, acidifying 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 of regulation, obtains the second waste water；5) and then by the second waste water adsorbed by storng-acid cation exchange resin again, elute, reclaim, obtain amino acid and the 3rd waste water, amino acid recovery is entered into step 1) in；6) desalting processing is carried out to the 3rd waste water again, obtains dissolving water；7) during dissolving water flows into sour water recovery storage tank, step 1 is entered back into) middle re-using.Amino acid starting material high usage that preparation method of the invention is obtained, product free acid are low, realize waste acid water recycled, and using water wisely does not produce 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 technology
Surfactant is a kind of important feature fine chemicals, is widely used in each industrial department and field.
Amino acid surfactant be with mild anion surfactant, it except the emulsification with surfactant, wash
Wash, disperse, foaming, permeating, outside the key property such as solubilising, due to having amide group and amino acid structure in design feature, making
The advantages of 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, surfactant product is increasingly paid close attention to people
The security of product, mildness and the raising to environmental protection requirement, such surfactant will increasingly by the weight 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, acidifying layering, is obtained
Oil reservoir-fat amic acid, then salt is neutralized into, amino acid surfactant, the general blowdown of water layer can be produced substantial amounts of useless
Acid, also content 5% or more amino-acid salt in waste acid water, portioned product in order to improve acyl chlorides conversion ratio, using 1.1 equivalents
Amino acid, the COD in such waste acid water is even more considerably beyond water discharge standard, if but acyl chlorides excess, product middle reaches can be caused again
It is higher from acid content, influence products application；Furthermore, as amino acid surfactant is more and more widely used in recent years, give up
The discharge of sour water is to bring serious environmental problem, if waste acid water is directly used directly as amidated solvent can cause again
The salt content of reaction is too high so that reaction system is sticky, influences reaction conversion ratio.
The content of the invention
In order to overcome the deficiencies in the prior art, made the invention provides a kind of industry of amino acid surfactant green circulatory
Preparation Method, the amino acid starting material high usage of the preparation method, product free acid are low, realize waste acid water recycled, economize on
Water, pollution environment is not produced, and green environment is friendly.
Realize that the purpose of the present invention can reach by adopting the following technical scheme that：
1) in the basic conditions, fat acyl chloride and amino acid carry out amidation process；
2) after amidation process, acidifying layering, upper strata obtains oil reservoir, and lower floor 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 of regulation, makes the pH of waste water less 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 adsorb, wash-out, reclaim, obtain amino acid and
3rd waste water, amino acid is recovered in recovery amino acid storage tank, and the amino acid reclaimed in amino acid storage tank enters back into step 1)
In carry out amidation process；
6) desalting processing is carried out to the 3rd waste water again, the 3rd waste water dissolves water by being obtained after desalting processing；
7) dissolving water flow into sour water reclaim storage tank in, enter back into step 1) in it is molten as amidating solvent and amino-acid salt
Xie Shui is re-used.
Preferably, step 1) in fat acyl chloride and amino acid mol ratio be 1：(1.2-2), the temperature of amidation process
It is 5-45 DEG C.
Preferably, step 1) in fat acyl chloride and amino acid mol ratio be 1：(1.2-1.5), the temperature of amidation process
Spend is 5-35 DEG C.
Preferably, step 1) in amino acid be methyl amimoacetic acid, glutamic acid, alanine, glycine, asparatate, silk
One kind in propylhomoserin.
Preferably, step 1) in aliphatic acid for oleic acid, linoleic acid, leukotrienes, isooctyl acid, isostearic acid, coconut oil,
One kind in palmitoleic acid, behenic acid, erucic acid；Or, fatty acid carbon chain is C8-C18, or their arbitrary mixture.
Preferably, step 5) in storng-acid cation exchange resin be polystyrene macroporous type strong-acid cation exchange
One kind in resin, polystyrene gel-type strong-acid cation-exchange resin.
Preferably, step 5) in the second waste water be 1-3L/min by the flow velocity of storng-acid cation exchange resin.
Preferably, step 5) in wash-out concretely comprise the following steps：Concentration is added to be eluted for the ammoniacal liquor of 0.1-1mol/L.
Preferably, step 6) in desalting processing method for crystallisation by cooling desalination, electrodialysis, counter-infiltration, ion exchange,
One kind or its any tandem compound method in multiple-effect evaporation.
Preferably, step 6) and step 7) between also include step 8), step 8) be specially：Dissolving is water-cooled to 5-20
DEG C, the inorganic salt crystal filtering that will be separated out determines the salt content in filtrate, supplements deionized water so that the salt content in filtrate
Less than 5%.
Compared to existing technology, the beneficial effects of the present invention are：
1st, 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, and using water wisely does not produce pollution environment, and green environment is friendly；
2nd, the green circulatory industrial production process of amino acid surfactant of the invention, be with fat acyl chloride, amino acid
Material synthesis propylhomoserin sodium class surfactant, amino acid surfactant is prepared using Schotten-Baumann reactions, acidifying
After produce waste acid water, sour water reclaims unreacted amino acid using resin adsorption, then by after desalting processing, directly with being used further to
Acylation reaction, the method realizes amino acid starting material high usage, while low free acid, waste acid water recycled, pollution is not produced
Environment, is a kind of industrial production technology for cleaning green.
Brief description of the drawings
Fig. 1 is the flow chart of the green circulatory industrial production process of amino acid surfactant of the invention.
Specific embodiment
Below, with reference to accompanying drawing and specific embodiment, the present invention is described further：
Embodiment 1
Initial reaction：
Add 250kg Sodium Glycinates, 2000kg water that cocounut oil acyl chlorides is added dropwise respectively under agitation in 5000L reactors
553Kg and 30% sodium hydroxide solution, it is 10-15 DEG C to keep kettle interior reaction temperature, and pH value 8-11,3h material dropping is finished,
0.5h is incubated at a temperature of this, reaction terminates, adds phosphoric acid, layering, upper strata obtains oil reservoir, and lower floor obtains the first waste water, oil
Layer adds water, NaOH to neutralize, and obtains sodium cocoyl glycinate.
First waste water is adjusted into pH to 2.0, the second waste water is obtained, the polystyrene macropore that the second waste water is passed through to have activated
Type strong-acid cation-exchange resin, flow velocity is 2L/min, treats that loading completely, is eluted with the ammoniacal liquor of 0.1moL/L, to appear
Amino acid detection signal starts to collect eluent, and gained eluent obtains amino acid and the 3rd waste water by concentration, admittedly contain
50%, amino acid content (Sodium Glycinate containing 45kg, the rate of recovery 85%) is determined, amino acid enters recovery amino acid storage tank.3rd
Waste water filters away the inorganic salt crystal for separating out by after polystyrene macroporous type strong-acid cation-exchange resin, being cooled to 5 DEG C
295kg (contains the crystallization water), determines salt content, supplements fresh water so that salt content is less than 5%, obtains dissolving water, and dissolving water enters
Sour water reclaims storage tank, again as amidating solvent.
Circulation is realized：
The fresh glycine of 205kg, 45kg is added to reclaim glycine (coming from amino acid storage tank) in 5000L reactors,
2000 dissolving water (reclaiming storage tank from sour water), are added dropwise acyl chlorides 553kg and 30% sodium hydroxide solution respectively under agitation, keep
Kettle interior reaction temperature is 10-15 DEG C, and pH value 8-11,3h material dropping is finished, and 0.5h is incubated at this temperature, and reaction terminates, plus
Enter phosphoric acid, be layered, upper strata obtains oil reservoir, lower floor obtains the first waste water, and oil reservoir adds water, NaOH to neutralize, obtains coconut palm
Oleoyl Sodium Glycinate, by HPLC (ODS2C18 posts, mobile phase：85% methyl alcohol, flow：1mL/min, column temperature：30 DEG C, detection
Device：UV254nm) external standard method, determines free acid 6.5%.
First waste water is adjusted into pH to 2.0, the second waste water is obtained, the polystyrene macropore that the second waste water is passed through to have activated
Type strong-acid cation-exchange resin, flow velocity is 2L/min, treats that loading completely, is eluted with the ammoniacal liquor of 0.1moL/L, to appear
Amino acid detection signal starts to collect eluent, and gained eluent obtains amino acid and the 3rd waste water by concentration, admittedly contain
50%, amino acid content (Sodium Glycinate containing 46kg, the rate of recovery 86%) is determined, amino acid enters recovery amino acid storage tank.3rd
Waste water filters away the inorganic salt crystal for separating out by after polystyrene macroporous type strong-acid cation-exchange resin, being cooled to 5 DEG C
310kg (contains the crystallization water), and filtrate determines salt content, supplements fresh water so that salt content is less than 5%, obtains dissolving water, dissolves water
Storage tank is reclaimed into sour water, again as amidating solvent.
Embodiment 2
Initial reaction：
In 5000L reactors add 250kg Sodium L-alaninates, 2000kg water, under agitation respectively be added dropwise acyl chlorides 303Kg and
30% sodium hydroxide solution, it is 36-40 DEG C to keep kettle interior reaction temperature, and pH value 8-11,2h material dropping is finished, at this temperature
Insulation 1h, reaction terminates, and adds phosphoric acid, layering, and upper strata obtains oil reservoir, and lower floor obtains the first waste water, and oil reservoir adds hydrogen-oxygen
Change sodium to neutralize, obtain cocounut oil acyl Sodium L-alaninate.
First waste water is adjusted into pH to 2.0, the second waste water is obtained, the polystyrene macropore that the second waste water is passed through to have activated
Type strong-acid cation-exchange resin, flow velocity is 1L/min, treats that loading completely, is eluted with the ammoniacal liquor of 0.15moL/L, to appear
Amino acid detection signal starts to collect eluent, and gained eluent obtains amino acid and the 3rd waste water by concentration, admittedly contain
50%, amino acid content (Sodium L-alaninate containing 88kg, the rate of recovery 83%) is determined, amino acid enters recovery amino acid storage tank.3rd
Waste water filters away the inorganic salt crystal for separating out by after polystyrene macroporous type strong-acid cation-exchange resin, being cooled to 5 DEG C
280kg (contains the crystallization water), and filtrate determines salt content, supplements fresh water so that salt content is less than 5%, obtains dissolving water, dissolves water
Storage tank is reclaimed into sour water, again as amidating solvent.
Circulation is realized：
162kg Sodium L-alaninates, 88kg is added to reclaim acid propyl (coming from amino acid storage tank) in 5000L reactors,
2000kg water (reclaims storage tank) from sour water, and acyl chlorides 303kg and 30% sodium hydroxide solution is added dropwise respectively under agitation, keeps kettle
Interior reaction temperature is 5-35 DEG C, and pH value 8-11,2h material dropping is finished, and 1h is incubated at this temperature, and reaction terminates, and adds phosphoric acid
Acidifying, layering, upper strata obtains oil reservoir, and lower floor obtains the first waste water, and oil reservoir adds NaOH to neutralize, obtains cocounut oil acyl alanine
Sodium, determines free acid 5.3% (assay method is with embodiment 11).
First waste water is adjusted into pH to 2.0, the second waste water is obtained, the polystyrene macropore that the second waste water is passed through to have activated
Type strong-acid cation-exchange resin, flow velocity is 1L/min, treats that loading completely, is eluted with the ammoniacal liquor of 0.2moL/L, to appear
Amino acid detection signal starts to collect eluent, and gained eluent obtains amino acid and the 3rd waste water by concentration, admittedly contain
50%, amino acid content (Sodium L-alaninate containing 88kg, the rate of recovery 83%) is determined, amino acid enters recovery amino acid storage tank.3rd
Waste water filters away the inorganic salt crystal for separating out by after polystyrene macroporous type strong-acid cation-exchange resin, being cooled to 5 DEG C
300kg (contains the crystallization water), and filtrate determines salt content, supplements fresh water so that salt content is less than 5%, obtains dissolving water, dissolves water
Storage tank is reclaimed into sour water, again as amidating solvent.
Embodiment 3
Initial reaction：
In 5000L reactors add 250kg L-Serine sodiums, 2000kg water, under agitation respectively be added dropwise acyl chlorides 238kg and
30% sodium hydroxide solution, it is 40-45 DEG C to keep kettle interior reaction temperature, and pH value 8-11.5,3.5h material dropping is finished, herein temperature
The lower insulation 1h of degree, reaction terminates, and adds phosphoric acid, layering, and upper strata obtains oil reservoir, and lower floor obtains the first waste water, and oil reservoir is added
NaOH is neutralized, and obtains cocounut oil acyl L-Serine sodium.
First waste water is adjusted into pH to 2.5, the second waste water is obtained, the polystyrene gel that the second waste water is passed through to have activated
Type strong-acid cation-exchange resin, flow velocity is 3L/min, treats that loading completely, is eluted, ammonia to appear with the ammoniacal liquor of 1moL/L
Base acid detection signal starts to collect eluent, and gained eluent obtains amino acid and the 3rd waste water by concentration, admittedly containing 50%,
Amino acid content (L-Serine sodium containing 117kg, the rate of recovery 88%) is determined, amino acid enters recovery amino acid storage tank.3rd waste water
By after polystyrene gel-type strong-acid cation-exchange resin, being cooled to 5 DEG C, the inorganic salt crystal for separating out is filtered away
249kg (contains the crystallization water), and filtrate determines salt content, supplements fresh water so that salt content is less than 5%, obtains dissolving water, dissolves water
Storage tank is reclaimed into sour water, again as amidating solvent.
Circulation is realized：
133kg L-Serine sodiums, 117kg is added to reclaim L-Serine sodium (coming from amino acid storage tank) in 5000L reactors,
2000kg water (reclaims storage tank) from sour water, and acyl chlorides 238kg and 30% sodium hydroxide solution is added dropwise respectively under agitation, keeps kettle
Interior reaction temperature is 40-45 DEG C, and pH value 8-11.5,3.5h material dropping is finished, and 1h is incubated at this temperature, and reaction terminates, plus
Enter phosphoric acid, be layered, upper strata obtains oil reservoir, lower floor obtains the first waste water, and oil reservoir adds NaOH to neutralize, obtains cocounut oil acyl
L-Serine sodium.Determine free acid 7.3% (assay method is with example 1)
First waste water is adjusted into pH to 2.0, the second waste water is obtained, the polystyrene gel that the second waste water is passed through to have activated
Type strong-acid cation-exchange resin, flow velocity is 3L/min, treats that loading completely, is eluted, ammonia to appear with the ammoniacal liquor of 1moL/L
Base acid detection signal starts to collect eluent, and gained eluent obtains amino acid and the 3rd waste water by concentration, admittedly containing 50%,
Amino acid content (L-Serine sodium containing 113kg, the rate of recovery 85%) is determined, amino acid enters recovery amino acid storage tank.3rd waste water
By after polystyrene gel-type strong-acid cation-exchange resin, being cooled to 5 DEG C, the inorganic salt crystal for separating out is filtered away
290kg (contains the crystallization water), and filtrate determines salt content, supplements fresh water so that salt content is less than 5%, obtains dissolving water, dissolves water
Storage tank is reclaimed into sour water, again as amidating solvent.
For a person skilled in the art, technical scheme that can be as described above and design, make other each
Plant corresponding change and deform, and all these changes and deforms the protection model that should all belong to the claims in the present invention
Within enclosing.
Claims (10)
1. the green circulatory industrial production process of a kind of amino acid surfactant, it is characterised in that comprise the following steps：
1) in the basic conditions, fat acyl chloride and amino acid carry out amidation process；
2) after amidation process, acidifying layering, upper strata obtains oil reservoir, and lower floor 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 of regulation, makes the pH of waste water less than the isoelectric point of amino acid, obtains the second waste water；
5) and then by the second waste water adsorbed by storng-acid cation exchange resin again, elute, reclaim, obtain amino acid and the 3rd
Waste water, by amino acid be recovered to recovery amino acid storage tank in, reclaim amino acid storage tank in amino acid enter back into step 1) in enter
Row amidation process；
6) desalting processing is carried out to the 3rd waste water again, the 3rd waste water dissolves water by being obtained after desalting processing；
7) dissolving water flow into sour water reclaim storage tank in, enter back into step 1) in as amidating solvent and amino-acid salt dissolving water
Re-use.
2. the green circulatory industrial production process of amino acid surfactant according to claim 1, it is characterised in that step
It is rapid 1) in fat acyl chloride and amino acid mol ratio be 1：(1.2-2), the temperature of amidation process is 5-45 DEG C.
3. the green circulatory industrial production process of amino acid surfactant according to claim 2, it is characterised in that step
It is rapid 1) in fat acyl chloride and amino acid mol ratio be 1：(1.2-1.5), the temperature of amidation process is 5-35 DEG C.
4. the green circulatory industrial production process of amino acid surfactant according to claim 1, it is characterised in that step
It is rapid 1) in amino acid be the one kind in methyl amimoacetic acid, glutamic acid, alanine, glycine, asparatate, serine.
5. the green circulatory industrial production process of amino acid surfactant according to claim 1, it is characterised in that step
It is rapid 1) in aliphatic acid be oleic acid, linoleic acid, leukotrienes, isooctyl acid, isostearic acid, coconut oil, palmitoleic acid, behenic acid, mustard
One kind in acid；Or, fatty acid carbon chain is C8-C18, or their arbitrary mixture.
6. the green circulatory industrial production process of amino acid surfactant according to claim 1, it is characterised in that step
It is rapid 5) in storng-acid cation exchange resin be polystyrene macroporous type strong-acid cation-exchange resin, polystyrene gel-type
One kind in strong-acid cation-exchange resin.
7. the green circulatory industrial production process of amino acid surfactant according to claim 1, it is characterised in that step
It is rapid 5) in the second waste water be 1-3L/min by the flow velocity of storng-acid cation exchange resin.
8. the green circulatory industrial production process of amino acid surfactant according to claim 1, it is characterised in that step
It is rapid 5) in wash-out concretely comprise the following steps：Concentration is added to be eluted for the ammoniacal liquor of 0.1-1mo l/L.
9. the green circulatory industrial production process of amino acid surfactant according to claim 1, it is characterised in that step
It is rapid 6) in desalting processing method for the one kind in crystallisation by cooling desalination, electrodialysis, counter-infiltration, ion exchange, multiple-effect evaporation or
Its any tandem compound method.
10. the green circulatory industrial production process of amino acid surfactant according to claim 1, it is characterised in that
Step 6) and step 7) between also include step 8), step 8) be specially：Dissolving is water-cooled to 5-20 DEG C, the inorganic salts that will be separated out
Crystal is filtered, and determines the salt content in filtrate, supplements deionized water so that the salt content in filtrate is less than 5%.
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| KR20220096902A (en) * | 2020-12-31 | 2022-07-07 | 노승호 | Alanine-based surfactant composition and human body cleaning composition comprising same |
| 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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Cited By (4)
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| KR20220096902A (en) * | 2020-12-31 | 2022-07-07 | 노승호 | Alanine-based surfactant composition and human body cleaning composition comprising same |
| KR102464655B1 (en) | 2020-12-31 | 2022-11-07 | 노승호 | Alanine-based surfactant composition and human body cleaning composition comprising same |
| 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 |
| WO2023184806A1 (en) * | 2022-04-01 | 2023-10-05 | 岳阳科罗德联合化学工业有限公司 | Production system and preparation method for continuous-flow production of salt-free amino acid surfactant |
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