CN114262276A - Method for directly synthesizing fatty acyl alanine salt from fatty acid - Google Patents
Method for directly synthesizing fatty acyl alanine salt from fatty acid Download PDFInfo
- Publication number
- CN114262276A CN114262276A CN202111630178.0A CN202111630178A CN114262276A CN 114262276 A CN114262276 A CN 114262276A CN 202111630178 A CN202111630178 A CN 202111630178A CN 114262276 A CN114262276 A CN 114262276A
- Authority
- CN
- China
- Prior art keywords
- fatty acid
- fatty
- reaction
- acid
- alanine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 60
- 239000000194 fatty acid Substances 0.000 title claims abstract description 60
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 60
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 52
- -1 fatty acyl alanine salt Chemical class 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 44
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 60
- 239000007787 solid Substances 0.000 claims abstract description 32
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims abstract description 26
- 235000004279 alanine Nutrition 0.000 claims abstract description 23
- 239000003513 alkali Substances 0.000 claims abstract description 20
- 238000010438 heat treatment Methods 0.000 claims abstract description 20
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 238000007789 sealing Methods 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000005639 Lauric acid Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- 238000010979 pH adjustment Methods 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 235000019864 coconut oil Nutrition 0.000 claims description 4
- 239000003240 coconut oil Substances 0.000 claims description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229960002446 octanoic acid Drugs 0.000 claims description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 2
- 239000003712 decolorant Substances 0.000 claims 1
- 238000004042 decolorization Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 35
- 239000006227 byproduct Substances 0.000 abstract description 12
- 238000007127 saponification reaction Methods 0.000 abstract description 6
- 238000007086 side reaction Methods 0.000 abstract description 6
- 239000007791 liquid phase Substances 0.000 abstract description 3
- 239000012466 permeate Substances 0.000 abstract description 3
- 230000005501 phase interface Effects 0.000 abstract description 3
- 229960003767 alanine Drugs 0.000 description 20
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 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 description 11
- 229940024606 amino acid Drugs 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 11
- 239000002994 raw material Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 9
- 150000002190 fatty acyls Chemical group 0.000 description 8
- 238000007112 amidation reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000004321 preservation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UYTOHYBIBPDOKX-ZDUSSCGKSA-N (2s)-2-(dodecanoylamino)propanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](C)C(O)=O UYTOHYBIBPDOKX-ZDUSSCGKSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- NRBFOSKZAWRBJI-KRWDZBQOSA-N N-Palmitoyl alanine Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(O)=O NRBFOSKZAWRBJI-KRWDZBQOSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000005202 decontamination Methods 0.000 description 2
- 230000003588 decontaminative effect Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940104261 taurate Drugs 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- SZCFGVHVAMAMQP-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)C[Na] Chemical compound C(CCCCCCCCCCC)(=O)C[Na] SZCFGVHVAMAMQP-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 238000005844 autocatalytic reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 150000002196 fatty nitriles Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010641 nitrile hydrolysis reaction Methods 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 229940104256 sodium taurate Drugs 0.000 description 1
- KKDONKAYVYTWGY-UHFFFAOYSA-M sodium;2-(methylamino)ethanesulfonate Chemical compound [Na+].CNCCS([O-])(=O)=O KKDONKAYVYTWGY-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Abstract
The invention discloses a method for directly synthesizing fatty acyl alanine salt by fatty acid, which comprises the steps of sequentially adding solid alkali, alanine and fatty acid into a reactor, sealing the reactor, replacing gas in the reactor, and maintaining the pressure in the reactor; heating step by step and reacting; and carrying out post-treatment on the obtained product to obtain the finished product of fatty acyl alanine salt. According to the invention, a specific feeding sequence and a specific reaction form are adopted, so that in the reaction process, the alanine and the fatty acid are in contact reaction at a solid-liquid phase interface, and the solid alkali permeates to the reaction interface through the alanine to catalyze and participate in the reaction; the alanine separates the fatty acid from the solid alkali, avoids the direct contact and saponification of the fatty acid and the alkali into by-product fatty acid salt, reduces the saponification side reaction of the fatty acid, and obtains a high-quality fatty acyl alanine salt product.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, relates to synthesis of fatty acyl alanine salt, and particularly relates to a method for directly synthesizing fatty acyl alanine salt by fatty acid, which can improve the product quality, reduce the production cost and eliminate the potential safety hazard of production.
Background
The surfactant has a series of physicochemical properties such as wetting, emulsifying, foaming, solubilizing, decontamination and the like and related applications. The development of the field of surfactants at home and abroad always takes the direction of greening and functionalization as development, the safety of product processes and raw materials and the high-efficiency and high-quality development of products are emphasized, the amino acid type surfactant is a product adapting to the development of times, and the fatty acyl amino acid salt is an amino acid type anionic surfactant and has good performances of wetting, emulsifying, foaming, decontamination, corrosion inhibition and the like; the participating reactants are all the components of organisms, are easy to biodegrade, have good product safety and accord with the development direction of times.
At present, the synthesis methods of fatty acyl amino acid salts mainly comprise a chemical synthesis method, an enzymatic synthesis method and a chemical-enzymatic synthesis method, the enzymatic method is not suitable for large-scale production, and the chemical synthesis method is still the main idea for synthesizing fatty acyl amino acid salts. The chemical synthesis method mainly comprises a fatty acid direct dehydration condensation method, a fatty acid anhydride amidation method, a fatty nitrile hydrolysis acylation method, a fatty amide carbonyl addition method, an ester compound amidation method and a fatty acyl chloride amidation reaction, namely a Showden-Bowman condensation process. At present, the fatty acyl amino acid salt is industrially produced mainly by adopting a Showden-Bowman condensation process, namely, the fatty acyl chloride is taken as a raw material to carry out amidation reaction with the amino acid salt in a mixed solvent of water and an organic solvent under an alkaline condition. The use of organic solvent and the raw material fatty acyl chloride in the process bring equimolar sodium chloride byproducts, so that the process needs complicated post-treatment to remove the solvent and the byproducts, thereby bringing high economic cost and a large amount of industrial wastewater, and simultaneously, the easy hydrolysis of the fatty acyl chloride can increase the fatty acid salt byproducts of the product. The process has various defects including high byproduct content, high economic cost, production safety problem caused by organic solvent and the like, solves the problems by improving a synthesis method or a process route, and has important practical significance for the development of fatty acyl amino acid salt products.
Research on synthesis of fatty acyl amino acid salts by using fatty acids as raw materials instead of fatty acyl chloride has been reported in a small number. The lauroyl methyl sodium taurate is synthesized by taking lauric acid and sodium methyl taurate as raw materials and boric acid as a catalyst in liquid paraffin, and the high proportion of the liquid paraffin and the use amount of the boric acid need to be removed by complex post-treatment, thereby bringing high economic cost and not being popularized. The patent CN106588710A adopts a special synthesis mode, namely microwave heating to synthesize the fatty acyl methyl taurate. At present, reports of directly synthesizing fatty acyl amino acid salt by taking fatty acid as raw material are only found in the synthesis of acyl methyl taurate products, and the synthesis of other amino acid salts is not reported.
Disclosure of Invention
The invention aims to provide a method for directly synthesizing fatty acyl alanine salt from fatty acid, which avoids the side reaction of direct contact saponification of fatty acid and alkali through a specific charging sequence, obtains a high-quality product, directly uses solid alkali for reaction, does not need to remove a solvent, obtains a product through reaction under the condition of no solvent, can adjust the pH and the solid content according to the requirements of customers, and ensures that the product is more convenient to apply.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for directly synthesizing fatty acyl alaninate from fatty acid comprises the following steps:
1) sequentially adding solid alkali, alanine and fatty acid into a reactor;
2) sealing the reactor, replacing gas in the reactor, and maintaining the pressure in the reactor;
3) heating step by step and reacting;
4) and carrying out post-treatment on the obtained product to obtain the finished product of fatty acyl alanine salt.
In the invention, solid alkali, alanine and fatty acid are used as raw materials, the reaction is carried out by means of the solid alkali osmosis autocatalysis reaction, fatty acyl alanine salt is prepared through amidation, and the reaction equation is shown in figure 2 by taking the reaction of lauric acid, L-alanine and sodium hydroxide as an example.
The method is characterized in that a specific feeding sequence is adopted, solid alkali is firstly added at the bottom of a reaction kettle, alanine is added, and fatty acid is finally added, wherein the reaction condition is gradual temperature rise, so that the alanine and the fatty acid are in contact reaction at a solid-liquid phase interface in the reaction process, and the solid alkali permeates to the reaction interface through the alanine to catalyze and participate in the reaction; the alanine separates the fatty acid from the solid alkali, so that the fatty acid is prevented from directly contacting with the alkali to be saponified into a byproduct fatty acid salt, and the saponification side reaction of the fatty acid is reduced, thereby obtaining a high-quality fatty acyl alanine salt product; the reaction is slowly carried out by gradually increasing the temperature, so that the amidation reaction rate is adapted to the permeation rate of solid alkali, other side reactions caused by overhigh temperature are prevented, and the color and luster of the product are deepened.
In a preferable embodiment of the invention, the molar ratio of the fatty acid, the alanine and the solid base in the step 1) is 1.0: 1.0-1.5.
As a preferred embodiment of the present invention, the fatty acid includes C8～C18Or a mixture thereof.
As a preferred embodiment of the present invention, the fatty acid comprises one or more of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid or coconut oil acid.
In a preferred embodiment of the present invention, the solid base is solid sodium hydroxide or solid potassium hydroxide in the form of tablet or granule.
As a preferable mode of the present invention, in the step 2), nitrogen is introduced to replace the gas in the reactor, and the pressure in the reactor is maintained at 0.01 to 0.05 MPa.
Introducing nitrogen gas for replacement to ensure that the interior of the reactor is in an oxygen-free environment so as to prevent the color of the raw material from being darkened due to high temperature; the reaction was promoted by continuously removing water generated during the reaction by continuously introducing nitrogen.
As a preferable scheme of the invention, in the step 3), the step-by-step temperature rise is to heat to 100 ℃ for reaction for 2 hours, heat to 120 ℃ for reaction for 2 hours, heat to 140 ℃ for reaction for 2 hours, and finally heat to 160 ℃ for reaction for 10 hours until the reaction is complete.
As a preferable embodiment of the present invention, in step 4), the post-treatment includes decoloring, pH adjustment, and solid content adjustment.
The pH adjustment is performed by using hydrochloric acid, sulfuric acid, citric acid, sodium hydroxide or potassium hydroxide and the like, the pH of the final product can be adjusted to 6-12 according to customer requirements, and the solid content can be adjusted to 30-60% according to customer requirements.
As a preferable scheme of the invention, the decoloring agent used for decoloring is hydrogen peroxide.
In a preferred embodiment of the present invention, the pH adjusting agent used for pH adjustment includes one of hydrochloric acid, sulfuric acid, citric acid, sodium hydroxide, and potassium hydroxide.
Compared with the existing Showden-Bowman condensation process method for industrially synthesizing fatty acyl alanine salt, the invention has the following beneficial effects:
1) according to the invention, the fatty acid raw material with green source is adopted to replace fatty acyl chloride, so that the problem of poor environmental friendliness of acyl chloride source is solved, and the price of the fatty acid is far lower than that of the fatty acyl chloride;
2) the fatty acid is used as the raw material, so that a byproduct sodium chloride in the product is avoided, the product does not need to be subjected to multiple separation and purification treatments, and the industrial three wastes are not generated in the whole synthesis process;
3) the method adopts a specific feeding sequence and a specific reaction form, namely, the solid alkali is separated by the alanine, so that the saponification side reaction of the fatty acid and the alkali is prevented, the content of the fatty acid salt is only 0.2-0.4%, the yield of the fatty acyl alanine salt can reach 98%, and the product quality is far higher than that of a market product;
4) the invention adopts a solvent-free method to avoid the use of organic solvent, thereby not only improving the yield of a single kettle, but also improving the greenness and safety of the production process and saving the recovery cost of the solvent;
5) the fatty acyl alaninate solid product obtained by the solvent-free method can adjust the solid content according to the requirements of customers, and is convenient to apply to the formulas of products such as daily chemicals.
Drawings
FIG. 1 is an infrared spectrum of sodium lauroyl alanine synthesized in example 1 of the present invention.
FIG. 2 is a reaction equation of the reaction of lauric acid, L-alanine and sodium hydroxide according to the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The embodiment provides a method for directly synthesizing fatty acyl alanine salt from fatty acid, which comprises the steps of sequentially adding 0.1mol of granular sodium hydroxide, 0.105mol of alanine and 0.1mol of lauric acid into a reactor, introducing nitrogen for 3 times of replacement, keeping the micro-positive pressure of a system at 0.01-0.05MPa, starting heating to 100 ℃ for reaction for 2 hours, then heating to 120 ℃ for reaction for 2 hours, then heating to 140 ℃ for reaction for 2 hours, finally heating to 160 ℃, and carrying out heat preservation reaction for 10 hours until the reaction is complete to obtain a crude product of sodium lauroyl alanine. Adding 10g of 2 wt.% hydrogen peroxide, carrying out heat preservation and decoloration treatment at 65 ℃, adding a small amount of citric acid, adjusting the pH to 7.5-8.5, adding water to adjust the solid content, obtaining a 50% aqueous solution product of sodium lauroyl alanine, wherein the color of the product is 38 ℃, the content of the by-product sodium fatty acid is only 0.42%, and the infrared spectrum of the sodium lauroyl alanine is shown in figure 1.
Example 2
The embodiment provides a method for directly synthesizing fatty acyl alanine salt from fatty acid, which comprises the steps of sequentially adding 0.1mol of flaky potassium hydroxide, 0.105mol of alanine and 0.1mol of coconut oil acid into a reactor, introducing nitrogen for 3 times of replacement, keeping the micro-positive pressure of a system at 0.01-0.05MPa, starting to heat to 100 ℃ for reaction for 2 hours, then heating to 120 ℃ for reaction for 2 hours, then heating to 140 ℃ for reaction for 2 hours, finally heating to 160 ℃, and carrying out heat preservation reaction for 10 hours until the reaction is complete, thus obtaining a crude product of the coconut oil acyl alanine potassium salt. Adding 10g of 2 wt.% hydrogen peroxide, carrying out heat preservation and decoloration treatment at 65 ℃, adding a small amount of hydrochloric acid, adjusting the pH to 8.0-9.0, adding water to adjust the solid content, obtaining a cocoyl potassium alanine 40% aqueous solution product, wherein the color of the product is 32 ℃, and the content of the byproduct potassium fatty acid is only 0.53%.
Example 3
The embodiment provides a method for directly synthesizing fatty acyl alanine salt from fatty acid, which comprises the steps of sequentially adding 0.1mol of flaky sodium hydroxide, 0.108mol of alanine and 0.1mol of myristic acid into a reactor, introducing nitrogen for 3 times of replacement, keeping the micro-positive pressure of a system at 0.01-0.05MPa, starting heating to 120 ℃ for reaction for 2 hours, then heating to 140 ℃ for reaction for 2 hours, then heating to 160 ℃ for reaction for 2 hours, finally heating to 180 ℃, and keeping the temperature for reaction for 10 hours until the reaction is complete, thereby obtaining a crude product of myristoyl alanine sodium. Adding 10g of 2 wt.% hydrogen peroxide, carrying out heat preservation and decoloration treatment at 65 ℃, adding a small amount of sodium hydroxide, adjusting the pH to 10.5-11.5, adding water to adjust the solid content, obtaining a 30% aqueous solution product of sodium lauroyl alanine, wherein the color of the product is 28 ℃, and the content of the by-product sodium aliphatate is only 0.58%.
Example 4
The embodiment provides a method for directly synthesizing fatty acyl alanine salt from fatty acid, which comprises the steps of sequentially adding 0.1mol of flaky sodium hydroxide, 0.110mol of alanine and 0.1mol of palmitic acid into a reactor, introducing nitrogen for replacement for 3 times, keeping the micro-positive pressure of a system at 0.01-0.05MPa, starting heating to 130 ℃ for reaction for 2 hours, then heating to 150 ℃ for reaction for 2 hours, then heating to 170 ℃ for reaction for 2 hours, finally heating to 190 ℃, and keeping the temperature for reaction for 10 hours until the reaction is complete to obtain a crude product of palmitoyl alanine sodium. Adding 10g of 2 wt.% hydrogen peroxide, carrying out heat preservation and decoloration treatment at 65 ℃, adding a small amount of sodium hydroxide, adjusting the pH to 10.5-11.5, adding water to adjust the solid content, obtaining a palmitoyl alanine sodium 30% aqueous solution product, wherein the color of the product is 36 degrees, and the content of the by-product sodium aliphatate is only 0.62%.
Comparative example 1
Changing the feeding sequence, sequentially adding 0.105mol of L-alanine, 0.1mol of granular sodium hydroxide and 0.1mol of lauric acid into a reactor, introducing nitrogen for 3 times of replacement, keeping the micro-positive pressure of the system at 0.01-0.05MPa, gradually heating to 130 ℃, keeping the temperature for reaction for 10 hours until the reaction is complete, and determining that the content of the sodium aliphatate is more than 60 percent, namely most of the lauric acid is converted into the sodium laurate, thereby indicating that the feeding sequence is not feasible.
Therefore, the specific feeding sequence and reaction form are adopted, so that in the reaction process, the alanine and the fatty acid are in contact reaction at a solid-liquid phase interface, and the solid alkali permeates to the reaction interface through the alanine to catalyze and participate in the reaction; the alanine separates the fatty acid from the solid alkali, so that the fatty acid is prevented from directly contacting with the alkali to be saponified into a byproduct fatty acid salt, and the saponification side reaction of the fatty acid is reduced, thereby obtaining a high-quality fatty acyl alanine salt product; the content of the fatty acid salt in the product prepared by the method is only 0.2-0.4%, the yield of the fatty acyl alanine salt can reach 98%, and the product quality is far higher than that of the product in the market.
While the invention has been described with respect to a preferred embodiment, it will be understood by those skilled in the art that the foregoing and other changes, omissions and deviations in the form and detail thereof may be made without departing from the scope of this invention. Those skilled in the art can make various changes, modifications and equivalent arrangements, which are equivalent to the embodiments of the present invention, without departing from the spirit and scope of the present invention, and which may be made by utilizing the techniques disclosed above; meanwhile, any changes, modifications and variations of the above-described embodiments, which are equivalent to those of the technical spirit of the present invention, are within the scope of the technical solution of the present invention.
Claims (10)
1. A method for directly synthesizing fatty acyl alanine salt from fatty acid is characterized by comprising the following steps:
1) sequentially adding solid alkali, alanine and fatty acid into a reactor;
2) sealing the reactor, replacing gas in the reactor, and maintaining the pressure in the reactor;
3) heating step by step and reacting;
4) and carrying out post-treatment on the obtained product to obtain the finished product of fatty acyl alanine salt.
2. The method for directly synthesizing fatty acyl alanine salt from fatty acid according to claim 1, wherein the molar ratio of fatty acid, alanine and solid base in step 1) is 1.0: 1.0-1.5.
3. The method for directly synthesizing fatty acyl alaninate by fatty acid according to claim 1, wherein the fatty acid comprises C8～C18Or a mixture thereof.
4. The method for directly synthesizing fatty acyl alaninate from fatty acids according to claim 3, wherein the fatty acids comprise one or more of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid or coconut oil acid.
5. The method for directly synthesizing fatty acyl alaninate from fatty acid according to claim 1, wherein the solid base is solid sodium hydroxide or solid potassium hydroxide in a flake or granular shape.
6. The method for directly synthesizing fatty acyl alanine salt from fatty acid according to claim 1, wherein in the step 2), nitrogen is introduced to replace the gas in the reactor, and the pressure in the reactor is maintained to be 0.01-0.05 MPa.
7. The method for directly synthesizing fatty acyl alanine salt from fatty acid according to claim 1, wherein in the step 3), the temperature is raised to 100 ℃ for reaction for 2h, raised to 120 ℃ for reaction for 2h, raised to 140 ℃ for reaction for 2h, and finally raised to 160 ℃ for reaction for 10h until the reaction is complete.
8. The method for directly synthesizing fatty acyl alaninate from fatty acid according to claim 1, wherein in the step 4), the post-treatment comprises decolorization, pH adjustment and solid content adjustment.
9. The method for directly synthesizing fatty acyl alaninate from fatty acid according to claim 8, wherein the decolorant used for decoloring is hydrogen peroxide.
10. The method for directly synthesizing fatty acyl alaninate by fatty acid according to claim 8, wherein the pH regulator used for pH adjustment comprises one of hydrochloric acid, sulfuric acid, citric acid, sodium hydroxide or potassium hydroxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111630178.0A CN114262276A (en) | 2021-12-28 | 2021-12-28 | Method for directly synthesizing fatty acyl alanine salt from fatty acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111630178.0A CN114262276A (en) | 2021-12-28 | 2021-12-28 | Method for directly synthesizing fatty acyl alanine salt from fatty acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114262276A true CN114262276A (en) | 2022-04-01 |
Family
ID=80831121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111630178.0A Pending CN114262276A (en) | 2021-12-28 | 2021-12-28 | Method for directly synthesizing fatty acyl alanine salt from fatty acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114262276A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1856565A (en) * | 2003-10-03 | 2006-11-01 | 味之素株式会社 | Detergent compositions and processes for the production thereof |
| CN108358802A (en) * | 2018-01-05 | 2018-08-03 | 石家庄菠莉亚日用化工有限公司 | A kind of preparation method of fat acidyl glycine salt surfactant |
| CN110809572A (en) * | 2017-05-12 | 2020-02-18 | 化工产品开发公司Seppic | Method for synthesizing N-acyl amino acid without using solvent or acyl chloride |
| WO2021254734A1 (en) * | 2020-06-16 | 2021-12-23 | Societe D'exploitation De Produits Pour Les Industries Chimiques - Seppic | Method for preparing an n-acyl amino acid by direct amidification of a fatty acid at high temperature |
-
2021
- 2021-12-28 CN CN202111630178.0A patent/CN114262276A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1856565A (en) * | 2003-10-03 | 2006-11-01 | 味之素株式会社 | Detergent compositions and processes for the production thereof |
| CN110809572A (en) * | 2017-05-12 | 2020-02-18 | 化工产品开发公司Seppic | Method for synthesizing N-acyl amino acid without using solvent or acyl chloride |
| CN108358802A (en) * | 2018-01-05 | 2018-08-03 | 石家庄菠莉亚日用化工有限公司 | A kind of preparation method of fat acidyl glycine salt surfactant |
| WO2021254734A1 (en) * | 2020-06-16 | 2021-12-23 | Societe D'exploitation De Produits Pour Les Industries Chimiques - Seppic | Method for preparing an n-acyl amino acid by direct amidification of a fatty acid at high temperature |
Non-Patent Citations (1)
| Title |
|---|
| 史立文等: "N-月桂酰基丙氨酸钠的绿色合成工艺研究", 《中国洗涤用品工业》, no. 7, 31 December 2023 (2023-12-31), pages 23 - 28 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2888226B2 (en) | Method to produce n-acyl amino acid surfactants using n-acyl amino acid surfactants or the corresponding anhydrides as catalysts | |
| CN105152957B (en) | The synthetic method of laurel acyl amino acid sodium | |
| CN103664665A (en) | Solid sodium sarcosine preparation method | |
| CN111004156A (en) | Method for synthesizing fatty acyl amino acid surfactant by direct method | |
| CN113698320A (en) | Preparation method of L-Carlactonitrile | |
| CN102557952B (en) | Method for preparing di-tert-butyl dicarbonate | |
| CN113493428A (en) | Method for synthesizing vitamin C tetraisopalmitate | |
| CN114262276A (en) | Method for directly synthesizing fatty acyl alanine salt from fatty acid | |
| CN108530301B (en) | Synthetic method of 2,4, 6-trifluorobenzylamine | |
| CN110981758A (en) | Synthetic method of fatty acyl amino acid surfactant | |
| CN114031516B (en) | Method for synthesizing N-acyl amino acid surfactant based on zirconium catalyst catalysis | |
| CN112812031B (en) | Preparation method of N-acyl amino acid type surfactant | |
| CN112661676B (en) | Method for preparing methanesulfonyl fluoride from methanesulfonyl chloride | |
| CN115197085B (en) | Preparation method of 2-amino-5-chloro-N, 3-dimethylbenzamide | |
| CN111196766A (en) | Purification and desalination method of L-carnitine crude product | |
| CN101492348A (en) | Method for producing 1-adamantane ethanol | |
| KR100261015B1 (en) | Method for preparing calsium gluconate using glucose oxidase under the pressurized condition | |
| CN110577467A (en) | Synthetic method of 3-hydroxypropionic acid | |
| CN111039811A (en) | Process for preparing nonane diacyl amino acid salt | |
| CN112174801B (en) | Method for coproducing glycolic acid and 1,1,1, 2-tetrafluoroethane by one-pot method | |
| CN110511134B (en) | Preparation method of 3-hydroxypropionic acid | |
| CN110684056B (en) | Chemical synthesis method of azithromycin intermediate | |
| CN109206331A (en) | A kind of preparation method of 2- methyl serine | |
| CN108084064B (en) | Novel preparation method of D- (-) -tartaric acid | |
| CN117567304A (en) | Hydrolysis method of (L) -3-cyano-2-hydroxypropyl trimethylammonium chloride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |