CN116621738A - Fatty amide propyl amine oxide and synthesis method thereof - Google Patents
Fatty amide propyl amine oxide and synthesis method thereof Download PDFInfo
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- CN116621738A CN116621738A CN202310557975.3A CN202310557975A CN116621738A CN 116621738 A CN116621738 A CN 116621738A CN 202310557975 A CN202310557975 A CN 202310557975A CN 116621738 A CN116621738 A CN 116621738A
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- amide propyl
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 150000002193 fatty amides Chemical class 0.000 title claims abstract description 48
- 238000001308 synthesis method Methods 0.000 title claims abstract description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 72
- 150000001412 amines Chemical class 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims abstract description 22
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 13
- 239000000194 fatty acid Substances 0.000 claims abstract description 13
- 229930195729 fatty acid Natural products 0.000 claims abstract description 13
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 20
- 238000001816 cooling Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 12
- 239000005639 Lauric acid Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 238000005070 sampling Methods 0.000 claims description 8
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 235000021314 Palmitic acid Nutrition 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 6
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 5
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 4
- -1 fatty amide propyl dimethylamine oxide Chemical class 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 230000002860 competitive effect Effects 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 239000003599 detergent Substances 0.000 description 22
- 238000004851 dishwashing Methods 0.000 description 13
- 238000001514 detection method Methods 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 5
- 230000008719 thickening Effects 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- LXAHHHIGZXPRKQ-UHFFFAOYSA-N 5-fluoro-2-methylpyridine Chemical compound CC1=CC=C(F)C=N1 LXAHHHIGZXPRKQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 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
- HSEMFIZWXHQJAE-UHFFFAOYSA-N Amide-Hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/75—Amino oxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides fatty amide propyl amine oxide and a synthesis method thereof, wherein the synthesis of the fatty amide propyl amine oxide is completed in two steps: the first step is to synthesize fatty acid amide propyl dimethylamine by fatty acid and N, N-dimethyl-1, 3-propane diamine; the second step is that fatty amide propyl dimethylamine reacts with hydrogen peroxide to prepare the fatty amide propyl dimethylamine oxide, wherein the fatty amide propyl dimethylamine oxide has light color, high active matter, low content of free amine and hydrogen peroxide and no inorganic salt; the method does not use an alkaline catalyst in the synthesis process, is simple and convenient to operate, does not use an organic solvent in the reaction process, and recycles unreacted N, N-dimethyl-1, 3-propanediamine, so that the method does not pollute the environment, effectively reduces the cost, simultaneously obtains fatty amide propyl amine oxide with the active matter higher than 35%, has the residual amounts of free amine and hydrogen peroxide lower than 0.1%, does not contain inorganic salt, and has a great competitive advantage compared with the products of the same type in the market.
Description
Technical Field
The invention relates to the technical field of surfactants, in particular to fatty amide propyl amine oxide and a synthesis method thereof.
Background
Fatty amidopropyl amine oxide is a surfactant with excellent performance, and the aqueous solution of the fatty amidopropyl amine oxide is nonionic under neutral or alkaline conditions and is weakly cationic in an acidic medium. Has excellent surface properties such as thickening, foam stabilizing, emulsifying, antistatic and the like, has good synergistic effect with anionic, cationic and nonionic surfactants, and has the functions of softening, moisturizing, sterilizing and mildew-proofing skin and hair.
At present, fatty amide propyl amine oxide is mainly prepared by carrying out amidation reaction on grease or fatty acid and N, N-dimethyl-1, 3-propylene diamine serving as raw materials to obtain fatty amide propyl dimethylamine; then the fatty amide propyl dimethylamine reacts with hydrogen peroxide with proper concentration to prepare the catalyst. In the synthesis process of the fatty amidopropyl dimethylamine, a single or mixed alkaline catalyst is generally used for accelerating the reaction rate and shortening the reaction time, but in the reaction process, the grease or fatty acid and the alkaline catalyst are easy to carry out saponification reaction, so that not only is the purity of the fatty amidopropyl dimethylamine reduced, but also the color of the generated fatty amidopropyl dimethylamine is deepened due to exothermic reaction of the saponification reaction, and the color of the fatty amidopropyl amine oxide obtained by subsequent synthesis is yellow. In the synthesis process of fatty amide propyl amine oxide, hydrogen peroxide is generally taken as an oxidant, and a complex catalyst is adopted to improve the stability of the hydrogen peroxide in order to prevent the hydrogen peroxide from being decomposed due to the influence of temperature in the reaction process.
However, the fatty amide propyl amine oxide synthesized by the prior art has the following problems: (1) The fatty acid content is high, and the fatty acid is easy to separate out when the fatty acid is used at low temperature in a formula system; (2) The residual content of free amine and hydrogen peroxide is high, and the product has certain irritation to human bodies; the residual quantity of hydrogen peroxide is high, and the stability of a formula system is easily damaged; (3) In the production process, residual hydrogen peroxide in the product is treated by reducing agents such as sodium sulfite, sodium bisulphite and the like, so that the product contains inorganic salts such as sodium sulfate, sodium bisulphite and the like, the fluidity of the product is easily reduced, the irritation of the product in a formula system is increased, and the product is easily subjected to yellowing; (4) low active content, increasing transportation costs; the active matter content is high, and the product is easy to form gel and the like.
Disclosure of Invention
The invention aims to provide high-activity fatty amide propyl amine oxide and a synthesis method and application thereof. The fatty amide propyl amine oxide has light color, high active matter content, low free amine and hydrogen peroxide content, and no inorganic salt.
In order to achieve the above purpose, the present invention provides the following technical solutions: the structural formula of the fatty amide propyl amine oxide is shown as formula (1):
wherein R is C 11 H 23 、C 13 H 27 、C 15 H 31 And C 17 H 35 One or more of the following.
Preferably, the C 11 H 23 、C 13 H 27 、C 15 H 31 And C 17 H 35 The composition in the fatty amidopropyl amine oxide is C respectively 11 H 23 The proportion of (C) is 55-100 wt% 13 H 27 The proportion of (C) is 0-20wt% 15 H 31 The proportion of (C) is 0-15 wt% 17 H 35 The proportion of (C) is 0-10 wt%.
A synthesis method of fatty amide propyl amine oxide comprises the following steps:
step 1: adding fatty acid into a reaction kettle, dissolving at 60-80 ℃, heating to 160-200 ℃, dropwise adding N, N-dimethyl-1, 3-propanediamine, reacting for 2-4 hours at constant temperature after the dropwise adding is finished, stopping the reaction according to the water outlet condition, cooling, vacuumizing, recovering unreacted N, N-dimethyl-1, 3-propanediamine, and cooling to obtain light yellow fatty amide propyl dimethylamine;
step 2: adding a proper amount of water and a complex catalyst into the reaction kettle, stirring and mixing uniformly at 60-90 ℃, then dripping a proper amount of hydrogen peroxide, reacting for 2-3 hours after dripping, sampling and detecting the content of free amine and hydrogen peroxide, cooling after the free amine and the hydrogen peroxide are qualified, and obtaining a light yellow transparent liquid, namely the target product fatty amide propyl amine oxide.
Preferably, in step 1, the fatty acid is selected from the group consisting of 55 to 100wt% of lauric acid, 0 to 20wt% of myristic acid, 0 to 15wt% of palmitic acid and 0 to 10wt% of stearic acid.
Preferably, in step 1, the molar ratio of fatty acid to N, N-dimethyl-1, 3-propanediamine is 1:1 to 1.1.
Preferably, in the step 2, the molar ratio of the fatty amide propyl dimethylamine to the hydrogen peroxide is 1:1 to 1.1.
Preferably, in step 2, the complex catalyst is one of EDTA and disodium EDTA.
Preferably, in step 2, the amount of the complex catalyst is 0.1 to 1.0wt% based on the total mass.
Preferably, in step 2, the fatty amidopropyl amine oxide is used in a dishwashing detergent.
Compared with the prior art, the invention has the beneficial effects that:
(1) The invention does not use alkaline catalyst in the synthesis process, and has simple synthesis method and convenient operation;
(2) The invention belongs to a green synthesis process, does not use an organic solvent in the reaction process, and recycles unreacted N, N-dimethyl-1, 3-propylene diamine, thereby not generating pollution to the environment and effectively reducing the cost;
(3) The active matter of the fatty amide propyl amine oxide obtained by the invention is higher than 35%, the residual amounts of the free amine and the hydrogen peroxide are all lower than 0.1%, and the fatty amide propyl amine oxide does not contain inorganic salt, and compared with the products of the same type on the market, the fatty amide propyl amine oxide has great competitive advantage;
(4) The fatty amide propyl amine oxide obtained by the invention is applied to a tableware detergent, and has good thickening and decontamination effects.
Detailed Description
The invention will now be described in more detail by way of examples which are illustrative only and are not intended to limit the scope of the invention in any way.
The invention provides a technical scheme that: the present invention will be described in detail with reference to examples. The examples are only preferred embodiments of the present invention and are not limiting of the present invention.
Example 1
A fatty amidopropyl amine oxide having the structural formula:
wherein R is C 11 H 23 。
The synthesis method of the fatty amide propyl amine oxide comprises the following specific steps:
(1) Adding 200g of lauric acid into a reaction kettle, dissolving at 60 ℃, heating to 160 ℃, dropwise adding 105g of N, N-dimethyl-1, 3-propanediamine, reacting at constant temperature for 2.5 hours after the dropwise adding is finished, stopping the reaction according to the water outlet condition, cooling, vacuumizing after the reaction is finished, recovering unreacted N, N-dimethyl-1, 3-propanediamine, and cooling to obtain light yellow fatty amide propyl dimethylamine;
(2) 242g of water and 1.8g of EDTA are added into the reaction kettle, the mixture is stirred and mixed uniformly at 70 ℃, 35g of 50% hydrogen peroxide is added dropwise, the reaction is carried out for 3 hours after the dropwise addition is finished, the contents of free amine and hydrogen peroxide are detected by sampling, and after the contents of free amine and hydrogen peroxide are qualified, the temperature is reduced, and light yellow transparent liquid is obtained, namely the target product fatty amide propyl amine oxide.
The detection results of the products are shown in Table 1
TABLE 1 detection results of fatty amidopropyl amine oxide synthesized in example 1
Example 2
A fatty amidopropyl amine oxide having the structural formula:
wherein R is C 11 H 23 、C 13 H 27 、C 15 H 31 And C 17 H 35 。
The synthesis method of the fatty amide propyl amine oxide comprises the following specific steps:
(1) 130g of lauric acid, 30g of myristic acid, 24g of palmitic acid and 16g of stearic acid are added into a reaction kettle, after dissolution at 60 ℃, the mixture is heated to 180 ℃, 100g of N, N-dimethyl-1, 3-propanediamine is dropwise added, the reaction is stopped at a constant temperature for 3 hours after the dropwise addition, the reaction is stopped according to the water outlet condition, after the reaction is finished, the mixture is cooled and vacuumized, unreacted N, N-dimethyl-1, 3-propanediamine is recovered, and the mixture is cooled to obtain pale yellow fatty amide propyl dimethylamine;
(2) Adding 462 water and 3.2g EDTA into the reaction kettle, stirring and mixing uniformly at 75 ℃, then dripping 66g of 50% hydrogen peroxide, reacting for 2.5h after dripping, sampling and detecting the content of free amine and hydrogen peroxide, cooling after passing, and obtaining light yellow transparent liquid, namely the target product fatty amide propyl amine oxide.
The detection results of the products are shown in Table 2
TABLE 2 detection results of fatty amidopropyl amine oxide synthesized in example 2
Example 3
A fatty amidopropyl amine oxide having the structural formula:
wherein R is C 11 H 23 、C 13 H 27 、C 15 H 31 And C 17 H 35 。
The synthesis method of the fatty amide propyl amine oxide comprises the following specific steps:
(1) 120g of lauric acid, 30g of myristic acid, 30g of palmitic acid and 20g of stearic acid are added into a reaction kettle, after dissolution at 70 ℃, the mixture is heated to 175 ℃, 102g of N, N-dimethyl-1, 3-propanediamine is dropwise added, the reaction is stopped at a constant temperature for 4 hours after the dropwise addition, the reaction is stopped according to the water outlet condition, after the reaction is finished, the mixture is cooled and vacuumized, unreacted N, N-dimethyl-1, 3-propanediamine is recovered, and the mixture is cooled to obtain pale yellow fatty amide propyl dimethylamine;
(2) Adding 419 water and 3.5g of EDTA disodium into the reaction kettle, stirring and mixing uniformly at 80 ℃, dropwise adding 117g of 27.5% hydrogen peroxide, reacting for 2.5 hours after the dropwise adding is finished, sampling and detecting the content of free amine and hydrogen peroxide, cooling after the free amine and the hydrogen peroxide are qualified, and obtaining a light yellow transparent liquid, namely the target product palmitoyl amide propyl amine oxide.
The detection results of the products are shown in Table 3
TABLE 3 detection results of fatty amidopropyl amine oxide synthesized in example 3
Example 4
A fatty amidopropyl amine oxide having the structural formula:
wherein R is C 11 H 23 、C 13 H 27 、C 15 H 31 And C 17 H 35 。
The synthesis method of the fatty amide propyl amine oxide comprises the following specific steps:
(1) 120g of lauric acid, 40g of myristic acid, 30g of palmitic acid and 10g of stearic acid are added into a reaction kettle, after dissolution at 65 ℃, heating is carried out to 185 ℃, 99g of N, N-dimethyl-1, 3-propanediamine is dropwise added, constant temperature reaction is carried out for 3 hours after the dropwise addition is finished, the reaction is stopped according to the water outlet condition, after the reaction is finished, cooling and vacuumizing are carried out, unreacted N, N-dimethyl-1, 3-propanediamine is recovered, and cooling is carried out, thus obtaining pale yellow fatty amide propyl dimethylamine;
(2) Adding 457 g of water and 4.8g of EDTA into the reaction kettle, stirring and mixing uniformly at 80 ℃, dropwise adding 65g of 50% hydrogen peroxide, reacting for 2.5h after the dropwise adding is finished, sampling and detecting the content of free amine and hydrogen peroxide, cooling after the free amine and the hydrogen peroxide are qualified, and obtaining light yellow transparent liquid, namely the target product fatty amide propyl amine oxide.
The detection results of the products are shown in Table 4
TABLE 4 detection results of fatty amidopropyl amine oxide synthesized in example 4
Example 5
A fatty amidopropyl amine oxide having the structural formula:
wherein R is C 11 H 23 、C 15 H 31 And C 17 H 35 。
The synthesis method of the fatty amide propyl amine oxide comprises the following specific steps:
(1) Adding 150g of lauric acid, 30g of palmitic acid and 20g of stearic acid into a reaction kettle, heating to 185 ℃ after dissolution at 80 ℃, dropwise adding 107g of N, N-dimethyl-1, 3-propanediamine, reacting at constant temperature for 3.5 hours after dropwise adding, stopping the reaction according to the water outlet condition, cooling and vacuumizing after the reaction is finished, recovering unreacted N, N-dimethyl-1, 3-propanediamine, and cooling to obtain pale yellow fatty amide propyl dimethylamine;
(2) Adding 408 water and 4.0g of EDTA disodium into a reaction kettle, stirring and mixing uniformly at 85 ℃, dropwise adding 120g of 27.5% hydrogen peroxide, reacting for 2.5 hours after the dropwise adding is finished, sampling and detecting the content of free amine and hydrogen peroxide, cooling after the free amine and the hydrogen peroxide are qualified, and obtaining light yellow transparent liquid, namely the target product fatty amide propyl amine oxide.
The detection results of the products are shown in Table 5
TABLE 5 detection results of fatty amidopropyl amine oxide synthesized in example 5
Example 6
A fatty amidopropyl amine oxide having the structural formula:
wherein R is C 11 H 23 、C 13 H 27 And C 17 H 35 。
The synthesis method of the fatty amide propyl amine oxide comprises the following specific steps:
(1) Adding 150g of lauric acid, 30g of myristic acid and 20g of stearic acid into a reaction kettle, heating to 190 ℃ after dissolution at 75 ℃, dropwise adding 104g of N, N-dimethyl-1, 3-propanediamine, reacting at constant temperature for 3 hours after dropwise adding, stopping the reaction according to the water outlet condition, cooling, vacuumizing, recovering unreacted N, N-dimethyl-1, 3-propanediamine, and cooling to obtain pale yellow fatty amide propyl dimethylamine;
(2) Adding 420g of water and 4.2g of EDTA disodium into a reaction kettle, stirring and mixing uniformly at 90 ℃, then dripping 121g of 27.5% hydrogen peroxide, reacting for 2 hours after dripping, sampling and detecting the content of free amine and hydrogen peroxide, cooling after passing, and obtaining light yellow transparent liquid, namely the target product fatty amide propyl amine oxide.
The detection results of the products are shown in Table 6
TABLE 6 detection results of fatty amidopropyl amine oxide synthesized in example 6
The fatty amidopropyl amine oxides synthesized in examples 1-6 above were compared for use in dishwashing detergent formulations. The fatty amidopropyl amine oxides synthesized in example 1, example 2, example 3, example 4, example 5 and example 6 were designated A, B, C, D, E and F, respectively. The formulation of a specific self-made dishwashing detergent is shown in table 7.
Table 7 homemade dishwashing detergent formulations
The formulation of the standard dishwashing detergent is shown in table 8.
Table 8 Standard dishwashing detergent formulations
| Material name | Proportion/wt% |
| Sodium alkylbenzenesulfonate | 14.0 |
| Ethoxylated alkyl sodium sulfate | 1.0 |
| Absolute ethyl alcohol | 5.0 |
| Urea | 5.0 |
| Hydrochloric acid/sodium hydroxide | Proper amount of |
| Deionized water | Allowance of |
Table 7 shows a self-made dishwashing detergent and Table 8 shows a standard dishwashing detergent. The viscosity of the dish detergents prepared with the fatty amidopropyl amine oxides prepared in examples 1 to 6 of Table 7 was measured and the detergency of the home-made dish detergents was compared with that of a standard dish detergent. The viscosity is measured by using an NDJ rotary viscometer at room temperature, and the higher the viscosity of the self-made tableware detergent product is, the better the thickening performance of the synthesized fatty amidopropyl amine oxide is shown; detergency was measured by the oil removal method according to the specification of the method B of the appendix GB 9985-2000. The determination of detergency is based on the fact that if the measured oil removal rate of the dishwashing detergent is not less than the oil removal rate of a standard dishwashing detergent, the detergency of the dishwashing detergent is determined to be acceptable. The results are shown in Table 9.
TABLE 9 viscosity and detergency of dishwashing detergents
| Tableware detergent | Viscosity (mPa. S) | Oil removal rate/% |
| Formulation 1 | 2200 | 43.87 |
| Formulation 2 | 2350 | 41.94 |
| Formulation 3 | 2520 | 40.75 |
| Formulation 4 | 2380 | 42.18 |
| Formulation 5 | 2480 | 42.58 |
| Formulation 6 | 2240 | 43.32 |
| Standard tableware detergent | — | 38.49 |
As can be seen from table 9: fatty amidopropyl amine oxides have excellent thickening and soil release properties for dishwashing detergent products. Thickening properties (">" means "relatively thick") of the fatty amidopropyl amine oxides synthesized in the examples were compared: example 3 > example 5 > example 4 > example 2 > example 6 > example 1. The detergency of the dish detergents prepared from the fatty amidopropyl amine oxides synthesized in examples 1 to 6 was superior to that of the standard dish detergents, and the detergency of the fatty amidopropyl amine oxides synthesized in each example (">" means "superior") was compared: example 1 > example 6 > example 5 > example 2 > example 4 > example 3.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (6)
1. The fatty amide propyl amine oxide is characterized by having a structural formula shown in a formula (1):
wherein R is C 11 H 23 、C 13 H 27 、C 15 H 31 And C 17 H 35 One or more of the following.
2. The fatty amidopropyl amine oxide of claim 1, wherein: the C is 11 H 23 、C 13 H 27 、C 15 H 31 And C 17 H 35 The composition in the fatty amidopropyl amine oxide is C respectively 11 H 23 Is in a ratio of 55～100wt％，C 13 H 27 The proportion of (C) is 0-20wt% 15 H 31 The proportion of (C) is 0-15 wt% 17 H 35 The proportion of (C) is 0-10 wt%.
3. The synthesis method of the fatty amide propyl amine oxide is characterized by comprising the following steps:
step 1: adding fatty acid into a reaction kettle, dissolving at 60-80 ℃, heating to 160-200 ℃, dropwise adding N, N-dimethyl-1, 3-propanediamine, reacting for 2-4 hours at constant temperature after the dropwise adding is finished, stopping the reaction according to the water outlet condition, cooling, vacuumizing, recovering unreacted N, N-dimethyl-1, 3-propanediamine, and cooling to obtain light yellow fatty amide propyl dimethylamine;
step 2: adding a proper amount of water and a complex catalyst into the reaction kettle, stirring and mixing uniformly at 60-90 ℃, then dripping a proper amount of hydrogen peroxide, reacting for 2-3 hours after dripping, sampling and detecting the content of free amine and hydrogen peroxide, cooling after the free amine and the hydrogen peroxide are qualified, and obtaining a light yellow transparent liquid, namely the target product fatty amide propyl amine oxide.
4. A method for synthesizing fatty amide propyl amine oxide according to claim 3, characterized in that: in step 1, the fatty acid is selected from the group consisting of 55 to 100wt% of lauric acid, 0 to 20wt% of myristic acid, 0 to 15wt% of palmitic acid and 0 to 10wt% of stearic acid.
5. A method for synthesizing fatty amide propyl amine oxide according to claim 3, characterized in that: in step 1, the molar ratio of fatty acid to N, N-dimethyl-1, 3-propanediamine was 1:1 to 1.1.
6. A method for synthesizing fatty amide propyl amine oxide according to claim 3, characterized in that: in the step 2, the mole ratio of the fatty amide propyl dimethylamine to the hydrogen peroxide is 1:1 to 1.1.
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