CN109796364A - A kind of preparation method of low viscosity amphoteric surfactant - Google Patents
A kind of preparation method of low viscosity amphoteric surfactant Download PDFInfo
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- CN109796364A CN109796364A CN201811624753.4A CN201811624753A CN109796364A CN 109796364 A CN109796364 A CN 109796364A CN 201811624753 A CN201811624753 A CN 201811624753A CN 109796364 A CN109796364 A CN 109796364A
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Abstract
The invention discloses a kind of preparation methods of low viscosity amphoteric surfactant; using fatty acid as raw material; by carrying out regioselectivity hydrolysis with the acylated cyclization of hydroxyethyl ethylenediamine, control pH value, being reacted under alkaline condition with monoxone, so that obtaining branch accounts for the lower amphoteric surfactant of leading viscosity.
Description
Technical field
The present invention relates to technical field of surfactant more particularly to a kind of preparation sides of low viscosity amphoteric surfactant
Method.
Background technique
Amphoteric surfactant is the not only table containing anionic hydrophilic base but also containing cationic hydrophilic base in same molecule
Face activating agent.Maximum is characterized in that it can provide proton but also receive proton.It is had the following characteristics that in use to knitting
Object has excellent flexible smooth and antistatic property;There are certain bactericidal properties and mildew resistance;There are good emulsibility and dispersibility.
Hydroxyethyl ethylenediamine is the synthesis material of common amphoteric surfactant, contains a primary amine and one in molecule
A secondary amine obtains amphoteric surfactant again by reacting with sodium chloroacetate after acylation reaction occurs with long chain fatty acids
4 are roughly divided by the synthesis process of the fatty acid amide amphoteric surfactant of representative of lauroyl both sexes sodium acetate
Step:
1) lauric acid is reacted with hydroxyethyl ethylenediamine (AEEA) generates cyclic intermediate;
2) (pH > 12) open loop is hydrolyzed in cyclic intermediate;
3) substitution reaction is carried out with sodium chloroacetate again after open loop;
4) remaining sodium chloroacetate is hydrolyzed to quench the reaction
ClCH2COONa+NaOH→OHCH2COONa+NaCl。
The viscosity that process above is produced is 10000-20000mPas, and solid content 35%-40% can not be produced dense
Degree is higher than 40% product, and otherwise the hydroxy acid sodium in product remains excessively high (typically larger than 7%), and product viscosity will be more than
30000mPas brings very big obstruction to the application of product.
Summary of the invention
For overcome the deficiencies in the prior art, make to control by control reaction condition the purpose of the present invention is to provide one kind
System reaction generates the preparation method of mobile low viscosity amphoteric surfactant to specified direction.
The purpose of the present invention adopts the following technical scheme that realization:
A kind of preparation method of low viscosity amphoteric surfactant, comprising the following steps:
1) fatty acid and hydroxyethyl ethylenediamine are put into reaction kettle by the molar ratio of 1:1.1-1.3, it is anti-in 160-180 DEG C
It answers, is evaporated under reduced pressure, is cooled to 70-100 DEG C;
2) material of step 1) is diluted with water, and it is 30-40% sodium hydrate aqueous solution that concentration, which is added dropwise, regulation system
PH value is 9.0-10.0, and temperature control hydrolyzes 1-3h to 60-70 DEG C;
3) by chloroethene acid dissolution, and the 30-40% sodium hydroxide solution mixing of 0.5-0.6 molar ratio is added, control is added
The speed of sodium hydroxide is to control temperature no more than 50 DEG C;
4) sodium hydroxide solution of the material of step 3) and 30-40% are added dropwise in the material of step 2) simultaneously, are controlled
The pH value of rate of addition to system is 9.5-10.5, after being added dropwise, in 80-90 DEG C of reaction 1-5h;
5) it continuously adds sodium hydroxide and adjusts pH to more than 13, in 100-130 DEG C of reaction 2-7h, citric acid is added in cooling
PH to 8.5-9.5 is adjusted, obtains active matter content not less than 50% low viscosity amphoteric surfactant.
Further, in step 1), the fatty acid is one in capric acid, lauric acid, tetradecylic acid, hexadecylic acid or stearic acid
Kind, the purity of the fatty acid is greater than 99%.The product of the fatty acid production high-concentration low-viscosity of single is more difficult, if it is mixed
Acid, such as cocinic acid, palmitinic acid etc. are closed, the product viscosity that fatty acid mixed produces under same process only has single fat acid
1/2-1/5.
Further, in step 1), 1-4h is reacted after material is first warming up to 160-180 DEG C, opens vacuum to vacuum degree
For -0.095MPa, it is continuously heating to 190-210 DEG C of vacuum distillation.
Further, in step 2), the concentration of sodium hydroxide is 32-35wt%.
Further, in step 2), the concentration of sodium hydroxide is 32-35wt%.
Further, the molar ratio of monoxone and the fatty acid in step 1) is 1.8-2.2:1 in step 3).
Further, in step 3), the molar ratio of monoxone and sodium hydroxide is 2:1.
Further, the molar ratio of the sodium hydroxide of chloroacetic mole and step 4) is 1:1.0-1.3 in step 3).
Further, in step 5), after 100-130 DEG C of reaction 2-7h, 60 DEG C are cooled to hereinafter, neutralizing using citric acid
It is 8.5-9.5 to pH.
Further, in 5), after 100-130 DEG C of reaction 2-7h, 60 DEG C are cooled to hereinafter, being neutralized to pH using citric acid
For 8.5-9.5.
Compared with prior art, the beneficial effects of the present invention are:
1) present invention carries out position by being acylated cyclization with hydroxyethyl ethylenediamine, controlling pH value again using fatty acid as raw material
Selective hydrolysis, by comparing hydroxyacetic acid and the remaining chloroacetic amount for the monoxone, generation being added in system it is found that control
When pH processed is hydrolyzed, the chloroethene acid content of one mole of fatty acid consumption increases substantially, while the viscosity of system declines to a great extent, this can
Can obtain branched product B due to open loop to account for leading intermediate and viscosity is caused to decline;
2) present invention after chloroethene acid dissolution by will use insufficient amount of sodium hydroxide to be neutralized to obtain under acid condition
Sodium chloroacetate, so that effectively reducing monoxone is hydrolyzed into hydroxyacetic acid, to improve monoxone and intermediate product A or B
Reaction efficiency;
3) present invention is added drop-wise in hydrolysate simultaneously by the chloroacetic acid solution and sodium hydroxide solution for neutralizing part,
By controlling the pH value of the rate of addition solution easier to control of two kinds of solution, hydroxyacetic acid is hydrolyzed into reduce sodium chloroacetate
Sodium improves its reaction efficiency with intermediate product;
4) the obtained amphoteric surfactant viscosity of the present invention is lower, solid content may be up to 50% transparency liquid system
Stablize.
Specific embodiment
In the following, being described further in conjunction with specific embodiment to the present invention, it should be noted that is do not collided
Under the premise of, new embodiment can be formed between various embodiments described below or between each technical characteristic in any combination.
The present invention provides a kind of preparation method of low viscosity amphoteric surfactant, comprising the following steps:
1) fatty acid and hydroxyethyl ethylenediamine are put into reaction kettle by the molar ratio of 1:1.1-1.3, it is anti-in 160-180 DEG C
It answers, is evaporated under reduced pressure, is cooled to 70-100 DEG C;
2) material of step 1) is diluted with water, and it is 30-40% sodium hydrate aqueous solution that concentration, which is added dropwise, regulation system
PH value is 9.0-10.0, and temperature control hydrolyzes 1-3h to 60-70 DEG C;
3) will be with water chloroethene acid dissolution by chloroethene acid dissolution, and the 30-40% sodium hydroxide that 0.5-0.6 molar ratio is added is molten
The speed of sodium hydroxide is added to control temperature no more than 50 DEG C in liquid mixing, control;
4) sodium hydroxide solution that the material of step 3) and concentration are 30-40% is added dropwise to the material of step 2) simultaneously
In, the pH value of control rate of addition to system is 9.5-10.5, after being added dropwise, in 80-90 DEG C of reaction 1-5h;
5) it continuously adds sodium hydroxide and adjusts pH to more than 13, in 100-130 DEG C of reaction 2-7h, citric acid is added in cooling
PH to 8.5-9.5 is adjusted, obtains active matter content not less than 50% low viscosity amphoteric surfactant.
By using excessive hydroxyethyl ethylenediamine and fatty acid acylated annulation occurs for this method, then is removed by vacuum
Go most hydroxyethyl ethylenediamine, obtain cyclic intermediate, sodium hydroxide solution is added dropwise at the pH of control, be hydrolyzed with
The mix products of B product dominance are obtained, finally nucleophilic displacement of fluorine are carried out with sodium chloroacetate, to obtain viscosity sharp fall
Low viscosity amphoteric surfactant.
Step 3) is configured to acid sodium chloroacetate solution using insufficient amount of sodium hydroxide and monoxone, so that preferably
It controls temperature and is no more than 50 DEG C, also effectively reduce the risk that monoxone is hydrolyzed to hydroxyacetic acid;
Step 4) is by the way that sodium hydroxide and sodium chloroacetate solution are added dropwise to simultaneously in reaction system, so as to be based on monoxone
Mole and sodium hydroxide molar ratio close to 1:2 because product is alkalinity, 1 mole of monoxone needs to neutralize a moles of hydrogen
Sodium oxide molybdena, and after monoxone and intermediate are quaternary ammoniated, about 1 mole of chloride ion of formation is also required to 1 mole of sodium hydroxide shape
At 1 mole nacl.
Further, in step 1), one of capric acid, lauric acid, tetradecylic acid, hexadecylic acid or stearic acid, the fat
The purity of acid is greater than 99%.The fatty acid of the chain length has convenient lipophilicity.
In step 1), after material is first warming up to 160-180 DEG C of reaction 1-4h, it being then turned on vacuum, control vacuum degree is-
0.9MPa is continuously heating to 190-210 DEG C of vacuum distillation.It is preferably that first the dehydration of progress a period of time is anti-at high temperature for material
It answers, then is reacted at vacuum, relatively higher temperature to remove remaining water and make fully reacting, and remove extra ethoxy
Ethylenediamine.
Embodiment 1:
A kind of preparation method of low viscosity amphoteric surfactant, comprising the following steps:
1) 1mol lauric acid and 1.2mol hydroxyethyl ethylenediamine are put into reaction kettle, in 170 DEG C of reaction 2.5h, opens vacuum
To vacuum degree be -0.095MPa, be warming up to 200 DEG C of vacuum distillation 3h, be cooled to 90 DEG C it is spare;
2) material of step 1) is diluted with water, the sodium hydroxide solution of 32wt% is added dropwise, control rate of addition so that body
The pH value of system is 9.0-9.5, and temperature control hydrolyzes 2h to 65 DEG C;
3) by 2mol chloroethene acid dissolution, and the 32% sodium hydroxide solution mixing of 1mol is added, sodium hydroxide is added in control
Speed to control temperature no more than 50 DEG C;
4) sodium hydroxide solution of the material of step 3) and 2.2mol 32% are added dropwise in the material of step 2) simultaneously,
The pH value for controlling rate of addition to system is 9.5-10.5, after being added dropwise, in 85 DEG C of reaction 3h;
5) 32% sodium hydroxide solution is added and adjusts pH to more than 13, in 120 DEG C of reaction 5h, be cooled to 60 DEG C hereinafter, plus
Enter lemon acid for adjusting pH to 8.5-9.5, obtains low viscosity amphoteric surfactant.
Embodiment 2:
A kind of preparation method of low viscosity amphoteric surfactant, comprising the following steps:
1) 1mol fatty acid and hydroxyl 1.3mol ethylethylenediamine are put into reaction kettle, in 160 DEG C of reaction 4h, opens vacuum extremely
Vacuum degree be -0.095MPa, be warming up to 180 DEG C of vacuum distillation 3h, be cooled to 80 DEG C it is spare;
2) material of step 1) is diluted with water, the sodium hydroxide solution of 35wt% is added dropwise, control rate of addition so that body
The pH value of system is 9.5-10.0, and temperature control hydrolyzes 2h to 65 DEG C;
3) by 2mol chloroethene acid dissolution, and the 35% sodium hydroxide solution mixing of 1mol is added, sodium hydroxide is added in control
Speed to control temperature no more than 50 DEG C;
4) sodium hydroxide solution of the material of step 3) and 2.5mol 35% are added dropwise in the material of step 2) simultaneously,
The pH value for controlling rate of addition to system is 9.5-10.5, after being added dropwise, in 85 DEG C of reaction 3h;
5) 35% sodium hydroxide solution is added and adjusts pH to more than 13, in 120 DEG C of reaction 5h, be cooled to 60 DEG C hereinafter, plus
Enter lemon acid for adjusting pH to 8.5-9.5, obtains low viscosity amphoteric surfactant.
Embodiment 3:
A kind of preparation method of low viscosity amphoteric surfactant, comprising the following steps:
1) 1mol coconut oil and 1.1mol hydroxyethyl ethylenediamine are put into reaction kettle, in 180 DEG C of reaction 1h, opens vacuum extremely
Vacuum degree be -0.095MPa, be warming up to 190 DEG C of vacuum distillation 3h, be cooled to 70 DEG C it is spare;
2) material of step 1) is diluted with water, the sodium hydroxide solution of 32wt% is added dropwise, control rate of addition so that body
The pH value of system is 9.0-9.5, and temperature control hydrolyzes 2h to 65 DEG C;
3) by 2mol chloroethene acid dissolution, and the 32% sodium hydroxide solution mixing of 1mol is added, sodium hydroxide is added in control
Speed to control temperature no more than 50 DEG C;
4) sodium hydroxide solution of the material of step 3) and 2.6mol 32% are added dropwise in the material of step 2) simultaneously,
The pH value for controlling rate of addition to system is 9.5-10.5, after being added dropwise, in 85 DEG C of reaction 3h;
5) 32% sodium hydroxide solution is added and adjusts pH to more than 13, in 120 DEG C of reaction 5h, be cooled to 60 DEG C hereinafter, plus
Enter lemon acid for adjusting pH to 8.5-9.5, obtains low viscosity amphoteric surfactant.
Comparative example 1:
A kind of preparation method of amphoteric surfactant, comprising the following steps:
1) 1mol coconut oil and 1.1mol hydroxyethyl ethylenediamine are put into reaction kettle, in 180 DEG C of reaction 1h, opens vacuum extremely
Vacuum degree be -0.095MPa, be warming up to 190 DEG C of vacuum distillation 3h, be cooled to 70 DEG C it is spare;
2) material of step 1) is poured into the sodium hydroxide solution of 32wt%, pH > 12, temperature control hydrolyzes 2h to 65 DEG C;
3) it by 2mol chloroethene acid dissolution, is added dropwise in the material of step 2) simultaneously with the sodium hydroxide solution of 3mol 32%,
The pH value for controlling rate of addition to system is 9.5-10.5, after being added dropwise, in 85 DEG C of reaction 3h;
4) 32% sodium hydroxide solution is added and adjusts pH to more than 13, in 120 DEG C of reaction 5h, be cooled to 60 DEG C hereinafter, plus
Enter lemon acid for adjusting pH to 8.5-9.5, obtains low viscosity amphoteric surfactant.
Performance detection and effect assessment
1. viscosity test
The low viscosity surface amphoteric surfactant that embodiment 1-3 is obtained uses DV-C viscosity test viscosity, in method
Solid content is tested, result is as shown in the table:
1 viscosity of table and solid content test mPas
Embodiment 1 | Embodiment 2 | Embodiment 3 | Comparative example 1 | |
Viscosity [mPas] | 2534 | 3023 | 3750 | 13560 |
Solid content [%] | 50.2% | 50.6% | 51.4% | 40.1% |
As seen from the above table, under the mol ratio of identical monoxone and fatty acid, using technique system provided by the invention
The viscosity of surfactant will reduce to original 1/3 to 1/4, and solid content can accomplish 50% or more.
2. residue test
Using ion chromatography hydroxyacetic acid and chloroacetic content, as a result as shown in the table.
2 residue test of table
Content | Embodiment 1 | Embodiment 2 | Embodiment 3 | Comparative example 1 |
Hydroxyacetic acid [%] | 3.6% | 3.5% | 3.7% | 8.7% |
Monoxone [ppm] | 12ppm | 10ppm | 10ppm | 105ppm |
As seen from the above table, for comparative example 1 compared with embodiment 1-3, chloroacetic mole is identical, but hydroxyacetic acid contains
Amount is obvious to be risen, i.e., the midbody product generated with identical fatty acid replaces, and chloroacetic consumption is bigger, in ring-type
In the product of mesosome open loop, the accounting amount of B is big, meanwhile, the viscosity of obtained surfactant is relatively low.
3. storage stability is tested
The low viscosity surface amphoteric surfactant that embodiment 1-3 and comparative example 1 are obtained is respectively placed in PE bottles of cappings
Storage 28 days in 50 ± 2 DEG C of baking oven, 0-4 DEG C of refrigerator, the variation of observed content object, as a result as shown in the table.
The test of 3 storage stability of table
50±2℃ | 0-4℃ | |
Embodiment 1 | Colorless transparent viscous liquid, no precipitating | Colorless transparent viscous liquid, no precipitating |
Embodiment 2 | Colorless transparent viscous liquid, no precipitating | Colorless transparent viscous liquid, no precipitating |
Embodiment 3 | Colorless transparent viscous liquid, no precipitating | Colorless transparent viscous liquid, no precipitating |
Comparative example 1 | Colorless transparent viscous liquid, no precipitating | Colorless transparent viscous liquid, no precipitating |
As seen from the above table, surfactant is obtained by embodiment 1-3, hydrophobic oleophobic system is under different temperature environments
Equally there is preferable stability.
The above embodiment is only the preferred embodiment of the present invention, and the scope of protection of the present invention is not limited thereto,
The variation and replacement for any unsubstantiality that those skilled in the art is done on the basis of the present invention belong to institute of the present invention
Claimed range.
Claims (8)
1. a kind of preparation method of low viscosity amphoteric surfactant, comprising the following steps:
1) fatty acid and hydroxyethyl ethylenediamine are put into reaction kettle by the molar ratio of 1:1.1-1.3, reacts, subtracts in 160-180 DEG C
Pressure distillation, is cooled to 70-100 DEG C;
2) material of step 1) is diluted with water, and it is 30-40% sodium hydrate aqueous solution, the pH value of regulation system that concentration, which is added dropwise,
For 9.0-10.0, temperature control hydrolyzes 1-3h to 60-70 DEG C;
3) by chloroethene acid dissolution, and the 30-40% sodium hydroxide solution mixing of 0.5-0.6 molar ratio is added, hydrogen-oxygen is added in control
Change the speed of sodium to control temperature no more than 50 DEG C;
4) sodium hydroxide solution that the material of step 3) and concentration are 30-40% is added dropwise in the material of step 2) simultaneously, is controlled
The pH value of rate of addition processed to system is 9.5-10.5, after being added dropwise, in 80-90 DEG C of reaction 1-5h;
5) it continuously adds sodium hydroxide and adjusts pH to more than 13, in 100-130 DEG C of reaction 2-7h, cooling is added citric acid and adjusts
PH to 8.5-9.5 obtains active matter content not less than 50% low viscosity amphoteric surfactant.
2. the preparation method of low viscosity amphoteric surfactant as described in claim 1, which is characterized in that in step 1), institute
Stating fatty acid is one of capric acid, lauric acid, tetradecylic acid, hexadecylic acid or stearic acid, and the purity of the fatty acid is greater than 99%.
3. the preparation method of low viscosity amphoteric surfactant as described in claim 1, which is characterized in that in step 1), first
1-4h is reacted after material is warming up to 160-180 DEG C, opening vacuum to vacuum degree is -0.095MPa, is continuously heating to 190-210
DEG C vacuum distillation.
4. the preparation method of low viscosity amphoteric surfactant as described in claim 1, which is characterized in that in step 2), hydrogen
The concentration of sodium oxide molybdena is 32-35wt%.
5. the preparation method of low viscosity amphoteric surfactant as described in claim 1, which is characterized in that chloroethene in step 3)
The molar ratio of acid and the fatty acid in step 1) is 1.8-2.2:1.
6. the preparation method of low viscosity amphoteric surfactant as described in claim 1, which is characterized in that in step 3), chlorine
The molar ratio of acetic acid and sodium hydroxide is 2:1.
7. the preparation method of low viscosity amphoteric surfactant as described in claim 1, which is characterized in that chloroethene in step 3)
The molar ratio of the sodium hydroxide of the mole and step 4) of acid is 1:1.0-1.3.
8. the preparation method of low viscosity amphoteric surfactant as described in claim 1, which is characterized in that in step 5),
After 100-130 DEG C of reaction 2-7h, 60 DEG C are cooled to hereinafter, being neutralized to pH using citric acid is 8.5-9.5.
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