CN114989030A - Preparation method of N-lauroyl sarcosine sodium - Google Patents
Preparation method of N-lauroyl sarcosine sodium Download PDFInfo
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- CN114989030A CN114989030A CN202210797984.5A CN202210797984A CN114989030A CN 114989030 A CN114989030 A CN 114989030A CN 202210797984 A CN202210797984 A CN 202210797984A CN 114989030 A CN114989030 A CN 114989030A
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- methyl laurate
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 title claims abstract description 30
- 108700004121 sarkosyl Proteins 0.000 title claims abstract description 30
- 239000011734 sodium Substances 0.000 title claims abstract description 30
- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 108
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 99
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims abstract description 84
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 48
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000005639 Lauric acid Substances 0.000 claims abstract description 24
- 108010077895 Sarcosine Proteins 0.000 claims abstract description 20
- 229940048098 sodium sarcosinate Drugs 0.000 claims abstract description 18
- JXHZRQHZVYDRGX-UHFFFAOYSA-M sodium;hydrogen sulfate;hydrate Chemical compound [OH-].[Na+].OS(O)(=O)=O JXHZRQHZVYDRGX-UHFFFAOYSA-M 0.000 claims abstract description 17
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 claims abstract description 16
- 238000006482 condensation reaction Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims description 11
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 28
- 239000003054 catalyst Substances 0.000 abstract description 17
- 239000013067 intermediate product Substances 0.000 abstract description 13
- 238000007086 side reaction Methods 0.000 abstract description 12
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000000344 soap Substances 0.000 abstract description 5
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 29
- 239000007787 solid Substances 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 10
- 235000011187 glycerol Nutrition 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910021536 Zeolite Inorganic materials 0.000 description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000010457 zeolite Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002190 fatty acyls Chemical group 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229940043230 sarcosine Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of N-lauroyl sarcosine sodium, which takes lauric acid and methanol as raw materials and sodium bisulfate monohydrate as a catalyst to prepare an intermediate product methyl laurate, does not need to add a solvent, avoids using virulent reaction materials, and has mild reaction conditions and less side reactions; the obtained intermediate product is subjected to condensation reaction with sodium sarcosinate and sodium methoxide serving as a catalyst to obtain N-sodium lauroyl sarcosinate, no inorganic salt is generated in the whole reaction process, the soap content in the product is reduced, the possibility of side reaction is reduced, the yield and the purity of the product are high, the yield of each step reaches about 90%, the viscosity of a reaction system is moderate, the difficulty of the post-treatment process is reduced, and the current situation that the reaction rate is greatly reduced due to overlarge viscosity in the reaction process is overcome; the whole reaction process only needs two steps, the reaction condition is mild, the reaction steps are few, and the preparation method is simple.
Description
Technical Field
The invention belongs to the technical field of surfactants, and particularly relates to a preparation method of N-lauroyl sarcosine sodium.
Background
N-sodium lauroyl sarcosinate, also known as sodium lauroyl sarcosinate, is a good detergent and foaming agent, can be used as a foaming agent of cosmetics and toothpaste, has small irritation to skin, is used as a detergent, has weak degreasing property, and is valued.
Chinese patents CN 113651714A and CN 111333531A both report methods for preparing N-lauroyl sarcosine sodium, but both of the patents use fatty acyl chloride as a reaction raw material, so that a large amount of NaCl cannot be introduced into a product, the viscosity of the whole reaction later stage is increased due to accumulation of NaCl and increase of the concentration of a surfactant in the reaction later stage, and the N-lauroyl sarcosine sodium has excellent foaming performance, so that mass transfer and heat transfer difficulties in the whole reaction later stage are comprehensively caused, thereby further increasing the hydrolysis probability of the fatty acyl chloride, increasing the soap content in the product, and reducing the yield. Meanwhile, due to the use of phosphorus trichloride and thionyl chloride, the pollution caused by the reaction is also large.
Therefore, there is a need for new methods of preparation which, while increasing the yield, reduce the difficulty of the post-treatment and minimize the contamination of the reaction.
Disclosure of Invention
The invention aims to provide a preparation method of N-lauroyl sarcosine sodium on the basis of the prior art, which takes lauric acid and methanol as raw materials, sodium bisulfate monohydrate as a catalyst to prepare an intermediate product of methyl laurate, and then the methyl laurate is subjected to condensation reaction with sodium sarcosine and a catalyst of sodium methoxide to obtain a product of N-lauroyl sarcosine sodium, so that the use of highly toxic reaction materials is avoided, the reaction conditions are mild, no inorganic salt is generated in the whole reaction process, the soap content in the product is reduced, the possibility of side reaction is reduced, the yield and the purity of the product are high, the yield of each step reaches about 90 percent, the viscosity of a reaction system is moderate, the difficulty of the post-treatment process is reduced, and the current situation that the reaction rate is greatly reduced due to overlarge viscosity in the reaction process is overcome.
The technical scheme of the invention is as follows:
a preparation method of N-lauroyl sarcosine sodium comprises the following steps:
(1) uniformly mixing lauric acid, methanol and sodium bisulfate monohydrate, and reacting at 75-85 ℃ to prepare methyl laurate;
(2) carrying out condensation reaction on the methyl laurate, the sodium sarcosinate and the sodium methoxide prepared in the step (1) at the temperature of 130-140 ℃ under the protection of nitrogen to prepare N-lauroyl sodium sarcosinate;
the specific synthetic route is as follows:
in the step (1), when preparing methyl laurate from lauric acid and methanol, the reaction temperature needs to be strictly controlled, and is too low, so that the reaction is incomplete, the smooth proceeding of the reaction is not facilitated, and the yield of intermediate products is low; the reaction temperature is too high, side reactions are liable to occur, and the yield and purity of the intermediate product are lowered. For the present invention, the reaction temperature is 75 to 85 ℃, and may be, but not limited to, 75 ℃, 78 ℃, 80 ℃, 82 ℃, 85 ℃, 88 ℃ or 90 ℃, and for better effect, the reaction temperature is 80 ℃.
The reaction time is 4 to 10 hours, but not limited to 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, or 10 hours, preferably 5 hours.
In the step (1), in the preparation of methyl laurate from lauric acid and methanol, even if the reaction temperature during the reaction is strictly controlled, the addition amount of methanol needs to be strictly controlled, and the yield and purity of the intermediate methyl laurate are reduced by over-high or under-low. Specifically, the molar ratio of lauric acid to methanol is 1: 8-10, but not limited to 1:8, 1:8.2, 1:8.5, 1:8.7, 1:9, 1:9.2, 1:9.5, 1:9.7 or 1:10, preferably, the molar ratio of lauric acid to methanol is 1: 8.5-9.5; more preferably, the molar ratio of lauric acid to methanol is 1:9.
In the step (1), in the process of preparing methyl laurate from lauric acid and methanol, even if the reaction temperature and the addition amount of methanol during the reaction are strictly controlled, the addition amount of sodium bisulfate monohydrate as a catalyst needs to be strictly controlled, and the addition amount is low, which is not favorable for smooth reaction and results in low yield of intermediate products; the addition amount is higher, other side reactions are easy to catalyze, the content of by-products is higher, and the yield and the purity of the intermediate product are reduced. Specifically, the molar ratio of lauric acid to sodium bisulfate monohydrate is 1:0.1 to 0.2, but may be, but not limited to, 1:0.1, 1:0.11, 1:0.12, 1:0.13, 1:0.14, 1:0.15, 1:0.1, 1:0.17, 1:0.18, 1:0.19 or 1:0.2, preferably the molar ratio of lauric acid to sodium bisulfate monohydrate is 1:0.13 to 0.17, more preferably the molar ratio of lauric acid to sodium bisulfate monohydrate is 1: 0.15.
In the step (1), a water separator is installed in the reaction process to reduce the moisture in the reaction process.
In the step (1), in the process of preparing the intermediate product methyl laurate, methanol is used as a raw material, a solvent is not required to be added, the use of highly toxic reaction materials is avoided, the reaction conditions are mild, the side reactions are few, the yield and the purity are high, the harm to people and the environment is small, and the method is suitable for industrial large-scale production.
In the step (2), methyl laurate is used as a reaction material, and in the process of preparing N-lauroyl sarcosine sodium, the reaction temperature needs to be strictly controlled, and is too low, so that the reaction is incomplete, the smooth proceeding of the reaction is not facilitated, and the yield of an intermediate product is low; the reaction temperature is too high, side reactions are liable to occur, and the yield and purity of the intermediate product are lowered. For the present invention, the reaction temperature is 130 to 140 ℃, but not limited to 130 ℃, 132 ℃, 135 ℃, 137 ℃, or 140 ℃, and for better effect, the reaction temperature is 135 ℃.
The reaction time is 3 to 8 hours, but not limited to 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, or 8 hours, preferably 4 hours.
In the step (2), in the process of preparing the product N-lauroyl sarcosine sodium from methyl laurate, even if the reaction temperature in the reaction process is strictly controlled, the adding amount of the sarcosine sodium needs to be strictly controlled, and the yield and the purity of the product N-lauroyl sarcosine sodium are reduced when the adding amount is too high or too low. Specifically, the molar ratio of methyl laurate to sodium sarcosinate is 1: 2.3-2.8, but the molar ratio is not limited to 1:2.3, 1:2.4, 1:2.5, 1:2.6, 1:2.7 or 1:2.8, and preferably the molar ratio of methyl laurate to sodium sarcosinate is 1: 2.5.
In the step (2), in the process of preparing the product N-sodium lauroyl sarcosinate from methyl laurate, a specific catalyst needs to be selected so as to improve the yield and the purity of the product N-sodium lauroyl sarcosinate. In the experimental process of exploring the catalyst, the application discovers that the reaction rate can be improved and the possibility of side reaction can be reduced by adopting sodium methoxide as the catalyst and strictly controlling the adding amount of the sodium methoxide, so that the yield and the purity of the product are high, and the yield reaches over 90 percent. And other similar catalysts, such as calcium oxide, sodium hydroxide and potassium hydroxide, are adopted, and the yield and the purity of the product N-lauroyl sarcosine sodium are low under the same reaction conditions.
Even if sodium methoxide is selected as the catalyst in step (2), the amount of sodium methoxide to be added must be strictly controlled. The adding amount is low, which is not beneficial to the smooth reaction and leads to low yield of the product; the dosage is higher, which is easy to catalyze other side reactions, so that the content of the by-product is higher, and the yield and the purity of the product are reduced. Specifically, the molar ratio of methyl laurate to sodium methoxide is 1:0.015 to 0.025, but the molar ratio is not limited to 1:0.015, 1:0.016, 1:0.017, 1:0.018, 1:0.019, 1:0.02, 1:0.021, 1:0.022, 1:0.023, 1:0.024 or 1:0.025, and preferably the molar ratio of methyl laurate to sodium methoxide is 1: 0.02.
In the step (2), in the process of preparing the product N-sodium lauroyl sarcosinate from methyl laurate, no inorganic salt is generated in the whole reaction process, the soap content in the product is reduced, the possibility of side reaction is reduced, the yield and the purity of the product are high, and the yield of each step reaches about 90 percent.
Furthermore, methyl laurate is used as an intermediate product, and the viscosity of a reaction system is moderate in the process of preparing N-lauroyl sarcosine sodium, so that the difficulty of the post-treatment process is reduced, and the current situation that the reaction rate is greatly reduced due to overlarge viscosity in the reaction process is overcome.
By adopting the technical scheme of the invention, the advantages are as follows:
(1) in the process of preparing the intermediate product methyl laurate, methanol is used as a raw material, a solvent is not required to be added, highly toxic reaction materials are avoided, the reaction condition is mild, side reactions are few, harm to people and the environment is small, and the method is suitable for industrial large-scale production.
(2) No inorganic salt is generated in the whole reaction process, the soap content in the product is reduced, the possibility of side reaction is reduced, the yield and the purity of the product are high, and the yield of each step reaches about 90 percent.
(3) Methyl laurate is used as an intermediate product, and the viscosity of a reaction system is moderate in the process of preparing N-lauroyl sarcosine sodium, so that the difficulty of the post-treatment process is reduced, and the current situation that the reaction rate is greatly reduced due to overlarge viscosity in the reaction process is overcome.
(4) The whole reaction process only needs two steps, the reaction condition is mild, the reaction steps are few, and the preparation method is simple.
Drawings
FIG. 1 is the NMR spectrum of N-lauroyl sarcosine sodium of example 1.
FIG. 2 is the MS spectrum of the product N-lauroyl sarcosine sodium in example 1.
Detailed Description
The present invention is further illustrated by the following examples, which are illustrative of the present invention and are not to be construed as being limited thereto.
EXAMPLE 1 preparation of sodium N-lauroyl sarcosinate
(1) Preparation of methyl laurate:
in a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1mol) of lauric acid, 36ml (0.9mol) of anhydrous methanol and 2.07g (0.015mol) of sodium bisulfate monohydrate were added as catalysts, and after stirring sufficiently and uniformly, zeolite was added, and the flask was equipped with a water separator and heated in a water bath at 80 ℃ for 5 hours. After the reaction, the organic layers were combined, allowed to stand, the reaction solution was decanted, the reaction solution was distilled under normal pressure, washed once with water, neutralized with an aqueous sodium carbonate solution to neutrality, then washed once with saturated sodium chloride, dried with anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 19.28g of a colorless transparent liquid with a yield of 89.95%.
(2) Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 27.75g (0.25mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.108g (0.002mol) of sodium methoxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 135 ℃, and stirred and reacted for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the mixture was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 27.09g of a pale yellow solid with a yield of 92.34%.
Comparative example 1
Preparation of methyl laurate:
in a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1mol) of lauric acid, 20ml (0.5mol) of anhydrous methanol and 2.07g (0.015mol) of sodium bisulfate monohydrate were added as catalysts, and after stirring sufficiently and uniformly, zeolite was added, and the flask was equipped with a water separator and heated in a water bath at 80 ℃ for a reaction of 5 hours. After the reaction, the organic layers were combined, allowed to stand, the reaction solution was decanted, the reaction solution was distilled under normal pressure, washed once with water, neutralized with an aqueous sodium carbonate solution to neutrality, then washed once with saturated sodium chloride, dried with anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 7.89g of a colorless transparent liquid with a yield of 36.81%.
Comparative example 2
Preparation of methyl laurate:
in a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1mol) of lauric acid, 61ml (1.5mol) of anhydrous methanol and 2.07g (0.015mol) of sodium bisulfate monohydrate were added as catalysts, and after stirring sufficiently and uniformly, zeolite was added, and the flask was equipped with a water separator and heated in a water bath at 80 ℃ for a reaction of 5 hours. After the reaction, the organic layers were combined, allowed to stand, the reaction solution was decanted, distilled under normal pressure, washed once with water, neutralized with an aqueous sodium carbonate solution to neutrality, then washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to obtain 14.28g of a colorless transparent liquid with a yield of 66.62%.
Comparative example 3
Preparation of methyl laurate:
in a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1mol) of lauric acid, 36ml (0.9mol) of anhydrous methanol and 0.69g (0.005mol) of sodium bisulfate monohydrate were added as catalysts, and after stirring sufficiently and uniformly, zeolite was added, and the flask was equipped with a water separator and heated in a water bath at 80 ℃ for a reaction of 5 hours. After the reaction, the organic layers were combined, allowed to stand, the reaction solution was decanted, distilled under normal pressure, washed once with water, neutralized with an aqueous sodium carbonate solution to neutrality, then washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to obtain 11.22g of a colorless transparent liquid with a yield of 52.35%.
Comparative example 4
Preparation of methyl laurate:
in a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1mol) of lauric acid, 36ml (0.9mol) of anhydrous methanol and 4.14g (0.03mol) of sodium bisulfate monohydrate were added as catalysts, and after stirring sufficiently and uniformly, zeolite was added, and the flask was equipped with a water separator and heated in a water bath at 80 ℃ for a reaction of 5 hours. After the reaction, the organic layers were combined, allowed to stand, the reaction solution was decanted, distilled under normal pressure, washed once with water, neutralized with an aqueous sodium carbonate solution to neutrality, then washed once with saturated sodium chloride, dried with anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to obtain 13.58g of a colorless transparent liquid with a yield of 63.36%.
Comparative example 5
Preparation of methyl laurate:
in a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1mol) of lauric acid, 36ml (0.9mol) of anhydrous methanol and 2.07g (0.015mol) of sodium bisulfate monohydrate were added as catalysts, and after stirring sufficiently and uniformly, zeolite was added, and the flask was equipped with a water separator and heated in a water bath at 70 ℃ for a reaction of 5 hours. After the reaction, the organic layers were combined, allowed to stand, the reaction solution was decanted, distilled under normal pressure, washed once with water, neutralized with an aqueous sodium carbonate solution to neutrality, then washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to obtain 16.22g of a colorless transparent liquid with a yield of 75.67%.
Comparative example 6
Preparation of methyl laurate:
20.4g (0.1mol) of lauric acid, 36ml (0.9mol) of anhydrous methanol and 2.07g (0.015mol) of sodium bisulfate monohydrate are added into a four-neck flask provided with a thermometer, a stirrer, a dropping funnel and a spherical condenser as catalysts, zeolite is added after the mixture is fully stirred uniformly, a water separator is arranged, and the mixture is heated and reacted for 5 hours in a water bath at the temperature of 90 ℃. After the reaction, the organic layers were combined, allowed to stand, the reaction solution was decanted, distilled under normal pressure, washed once with water, neutralized with an aqueous sodium carbonate solution to neutrality, then washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to obtain 15.89g of a colorless transparent liquid with a yield of 74.13%.
Comparative example 7
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 16.65g (0.15mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.108g (0.002mol) of sodium methoxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 135 ℃, and stirred and reacted for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the reaction was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 16.32g of a pale yellow solid with a yield of 55.63%.
Comparative example 8
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 38.85g (0.35mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.108g (0.002mol) of sodium methoxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 135 ℃, and stirred and reacted for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the mixture was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 20.89g of a pale yellow solid with a yield of 71.20%.
Comparative example 9
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 27.75g (0.25mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.108g (0.002mol) of sodium methoxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 120 ℃ and stirred for reaction for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the reaction was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 21.22g of pale yellow solid with a yield of 72.33%.
Comparative example 10
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 27.75g (0.25mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.108g (0.002mol) of sodium methoxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 150 ℃ and stirred for reaction for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the mixture was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 20.26g of a pale yellow solid with a yield of 69.06%.
Comparative example 11
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 27.75g (0.25mol) of sodium sarcosinate, 92g (1mol) of glycerin and 0.112g (0.002mol) of calcium oxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 135 ℃, and stirred and reacted for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the reaction was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 18.45g of a pale yellow solid with a yield of 62.89%.
Comparative example 12
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 27.75g (0.25mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.08g (0.002mol) of sodium hydroxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 135 ℃, and stirred and reacted for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the mixture was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 23.46g of a pale yellow solid with a yield of 79.96%.
Comparative example 13
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 27.75g (0.25mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.12g (0.002mol) of potassium hydroxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 135 ℃, and stirred and reacted for 4 hours under the protection of nitrogen. After the reaction was completed, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the mixture was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 21.53g of a pale yellow solid with a yield of 73.39%.
Comparative example 14
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 27.75g (0.25mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.054g (0.001mol) of sodium methoxide are added into a four-neck flask with a mechanical stirrer, a thermometer, a spherical condenser and a water separator, stirred uniformly, heated to 135 ℃, and stirred and reacted for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the reaction was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 12.36g of pale yellow solid with a yield of 42.13%.
Comparative example 15
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1mol) of methyl laurate prepared in the step (1), 27.75g (0.25mol) of sodium sarcosinate, 92g (1mol) of glycerol and 0.162g (0.003mol) of sodium methoxide are added into a four-necked flask with a mechanical stirrer, a thermometer, a spherical condenser and a water knockout drum, stirred uniformly, heated to 135 ℃, and stirred and reacted for 4 hours under the protection of nitrogen. After the reaction, ethyl acetate was added to the obtained reaction solution to extract the upper white solid, and the mixture was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 21.56g of a pale yellow solid with a yield of 73.49%.
The above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: modifications may be made to the technical solutions described in the foregoing embodiments, or equivalents may be substituted for some of the technical features; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. A preparation method of N-lauroyl sarcosine sodium is characterized by comprising the following steps:
(1) uniformly mixing lauric acid, methanol and sodium bisulfate monohydrate, and reacting at 75-85 ℃ to prepare methyl laurate;
(2) under the protection of nitrogen, carrying out condensation reaction on the methyl laurate, the sodium sarcosinate and the sodium methoxide prepared in the step (1) at the temperature of 130-140 ℃ to prepare N-lauroyl sodium sarcosinate;
the specific synthetic route is as follows:
2. the method for preparing sodium N-lauroylsarcosine according to claim 1, wherein in the step (1), the reaction temperature is 80 ℃; the reaction time is 4 to 10 hours, preferably 5 hours.
3. The method for preparing sodium N-lauroylsarcosine according to claim 1, wherein a molar ratio of lauric acid to methanol in step (1) is 1:8 to 10.
4. The method for preparing sodium N-lauroylsarcosine according to claim 3, wherein in the step (1), the molar ratio of lauric acid to methanol is 1:8.5 to 9.5; preferably 1:9.
5. The method for preparing sodium N-lauroylsarcosine according to claim 1, wherein in the step (1), the molar ratio of lauric acid to sodium bisulfate monohydrate is 1:0.1 to 0.2.
6. The method for preparing sodium N-lauroylsarcosine according to claim 5, wherein in the step (1), the molar ratio of lauric acid to sodium hydrogensulfate monohydrate is 1:0.13 to 0.17; preferably 1: 0.15.
7. The method for preparing sodium N-lauroylsarcosine according to claim 1, wherein in the step (2), the condensation reaction temperature is 135 ℃; the reaction time is 3 to 8 hours, preferably 4 hours.
8. The method for preparing sodium N-lauroylsarcosine according to claim 1, wherein in the step (2), the molar ratio of methyl laurate to sodium sarcosinate is 1:2.3 to 2.8; preferably 1: 2.5.
9. The method for producing sodium N-lauroylsarcosine according to claim 1, wherein in the step (2), the molar ratio of methyl laurate to sodium methoxide is 1:0.015 to 0.025; preferably 1: 0.02.
10. The method for preparing sodium N-lauroylsarcosine according to claim 1, wherein in the step (1), a water separator is installed during the reaction to reduce moisture during the reaction.
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