CN103951581A - Synthesis of n-undecane diacyl diaspartic acid-bis-diglycolamine salt - Google Patents
Synthesis of n-undecane diacyl diaspartic acid-bis-diglycolamine salt Download PDFInfo
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- CN103951581A CN103951581A CN201410135965.1A CN201410135965A CN103951581A CN 103951581 A CN103951581 A CN 103951581A CN 201410135965 A CN201410135965 A CN 201410135965A CN 103951581 A CN103951581 A CN 103951581A
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Abstract
The invention discloses synthesis of an n-undecane diacyl diaspartic acid-bis-diglycolamine salt. The synthesis is characterized by comprising the steps: with ethyl acetate as a solvent, carrying out a reflux reaction of n-undecane dibasic acid with new-steamed thionyl chloride under the action of a catalyst, and generating a mixture of n-undecane diacyl chloride and n-undecane dianhydride; in the presence of an acid-binding agent, carrying out a reaction of the mixture of n-undecane diacyl chloride and n-undecane dianhydride with sodium aspartate in a mixed solvent of acetone and water, and generating n-undecane diacyl sodium bisaspartate; diluting the reaction product with water, pickling, washing with water to obtain n-undecane diacyl bisaspartic acid, then adding into diglycolamine, stirring to dissolve, and thus obtaining the n-undecane diacyl diaspartic acid-bis-diglycolamine salt. The n-undecane diacyl diaspartic acid-bis-diglycolamine salt has an excellent antirust effect, has an effect of forming stable complexes with calcium ions and magnesium ions, is simple and practicable in reaction operations, and is suitable for industrialized production.
Description
Technical field
The present invention relates to rust-inhibiting additive synthesis technical field, espespecially a kind of positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt synthetic.
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Background technology
Inhibiter is as a kind of additive; in metal processing, play the effect that prevents corrosion and wearing and tearing; inhibiter is owing to containing one or more slowly-releasing group in molecule; by physical adsorption or be chemisorbed on metallic surface form molecular orientation arrange protective membrane; thereby slow down or suppressed the corrosion of metallic matrix, receive much concern.The alcohol amine salt of carboxylic acid and derivative all has certain rust-preventing characteristic, resistance to abrasion and antifriction quality, major cause is the carboxyl all in the hydramine molecules of salt of carboxylic acid and derivative with strong polarity, their molecular adsorption is in the surface of iron, form firmly chemisorbed layer, play antirust effect, in addition, be chemisorbed on friction under high load condition and react, generate high-intensity friction chemical reaction film, this is the major cause that they have better wear-resistant, antifriction and supporting capacity.
When working fluid preparation is used, generally adopt under normal circumstances tap water, underground water banned adopting just gradually now, due to contacted surrounding environment and medium different, therefore impurity liquid contained in water is not quite similar, water hardness is also different, surface water impurities comprises oxygen, nitrogen, carbonic acid gas, dust, microorganism, solubility salt, suspended substance and erosion etc., in the time that the alcohol amine salt of aliphatic carboxylic acid and derivative contacts with hard water, calcium ion and magnesium ion form insoluble calcium soap and magnesium soap with the effect of aliphatic carboxylic acid radical ion, thereby cause too much consumption, water hardness is higher, the consumption of lipid acid also just the more, therefore, water hardness has a strong impact on the rustless property of inhibiter.
Summary of the invention
The object of the present invention is to provide the synthetic of a kind of positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt.
Technical solution of the present invention is: taking ethyl acetate as solvent, positive DC11 carries out back flow reaction with the new sulfur oxychloride steaming under catalyst action, generates positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydride mixtures; Under acid binding agent exists, the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides reacts with Asparagus cochinchinensis ammonia acid sodium in the mixed solvent of acetone and water, generates positive 11 carbon diacyls pair Asparagus cochinchinensis ammonia acid sodiums; After reaction mass dilute with water, pickling and washing, obtain the just two aspartic acids of 11 carbon diacyls, then join in diglycolamine, stirring and dissolving, makes positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt.Specifically comprise following steps:
1). taking ethyl acetate as solvent, positive DC11 (I) and the new sulfur oxychloride steaming in molar ratio 1 ﹕ 1.5～2.5 feed intake, N, dinethylformamide is catalyzer, under stirring 80 DEG C～85 DEG C back flow reaction 4～7 hours, tail gas alkali liquor absorption, generate positive 11 carbon diacid chlorides (II) and positive 11 carbon dicarboxylic anhydrides (III), after completion of the reaction, Distillation recovery ethyl acetate, its main chemical reactions is:
2). under acid binding agent exists, the mixture of positive 11 carbon diacid chlorides (II) and positive 11 carbon dicarboxylic anhydrides (III), slowly join in the acetone of Asparagus cochinchinensis ammonia acid sodium (IV) and the mixed solvent of water in batches, make temperature of reaction system be controlled at 5 DEG C～10 DEG C, after the mixture of positive 11 carbon diacid chlorides (II) and positive 11 carbon dicarboxylic anhydrides (III) adds, being warming up to 25 DEG C～35 DEG C reacts 2～3 hours, be warming up to 45 DEG C～65 DEG C continuation reactions 2～3 hours, generate the two Asparagus cochinchinensis ammonia acid sodiums (V) of positive 11 carbon diacyls, after completion of the reaction, Distillation recovery acetone, its main chemical reactions is:
3). resultant of reaction water dilutes, and slowly adds acid solution, adjusts PH to 1.0 left and right, separates out solid product, and water repetitive scrubbing product obtains the just two aspartic acids (VI) of 11 carbon diacyls, and its main chemical reactions is:
4). two positive 11 carbon diacyls aspartic acids are joined in diglycolamine, be heated to 40 DEG C～50 DEG C, stirring and dissolving, makes positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt (VII), and its main chemical reactions is:
Further, described ethyl acetate consumption is 100%～120% of positive DC11 consumption.
Described DMF catalyst levels is 1%～5% of positive DC11 consumption.
Described alkali lye is aqueous sodium carbonate.
Described acid binding agent is that concentration is 20% aqueous sodium hydroxide solution.
Described acetone and the volume ratio of water are 1 ﹕ 1.
Described Asparagus cochinchinensis ammonia acid sodium is 1 ﹕ 1.5～2 with the mol ratio of positive DC11.
Described acid solution is sulphuric acid soln or hydrochloric acid soln.
The mol ratio of the two aspartic acids of described positive 11 carbon diacyls and diglycolamine is 1 ﹕ 4～6.
The synthetic method of a kind of positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt of the present invention, its feature and advantage are: sufficient raw, cost is lower; Reduce the consumption of sulfur oxychloride, reduce the corrosion to equipment; Synthetics is a kind of organic polycarboxylic acid, has the characteristic of multiple carboxyls and melts combine, can play excellent rust inhibition, and has the effect of the stable comple forming with calcium, magnesium ion, can softening of water; Operation is simple, is applicable to suitability for industrialized production.
Embodiment
Embodiment 1
30 grams of positive DC11s and 36 grams of ethyl acetate are put in corrosion-resistant reactor, 0.3 gram of N, dinethylformamide, add 41 grams of new sulfur oxychlorides that steam, under stirring, 80 DEG C～85 DEG C back flow reaction 4 hours, tail gas alkali liquor absorption, generated positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides, after completion of the reaction, Distillation recovery ethyl acetate, whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the mixed solvent of 33 grams of Asparagus cochinchinensis ammonia acid sodiums and 50 milliliters of acetone and water, it is 10 that the sodium hydroxide solution that is 20% by concentration regulates PH, under fully stirring, slowly add again the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides and 20% sodium hydroxide solution in batches, make temperature of reaction system be controlled at 5 DEG C～10 DEG C, it is 9～10 that PH controls, after the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides adds, being warming up to 25 DEG C～35 DEG C reacts 2 hours, it is 9～10 that PH controls, be warming up to again 45 DEG C～65 DEG C and continue reaction 3 hours, it is 9～10 that PH controls, generate the two Asparagus cochinchinensis ammonia acid sodiums of positive 11 carbon diacyls, after completion of the reaction, Distillation recovery acetone, reaction mass water dilutes, and slowly adds acid solution, adjusts PH to 1.0 left and right, separates out solid product, and water repetitive scrubbing product obtains the just two aspartic acids of 11 carbon diacyls, two positive 11 carbon diacyls aspartic acids are joined in 45 grams of diglycolamines, and stirring and dissolving, makes positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt.
Embodiment 2
36 grams of positive DC11s and 36 grams of ethyl acetate are put in corrosion-resistant reactor, add 1.8 grams of N, dinethylformamide, add again 30 grams of new sulfur oxychlorides that steam, under stirring, 80 DEG C～85 DEG C back flow reaction 7 hours, tail gas alkali liquor absorption, generated positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides, after completion of the reaction, Distillation recovery ethyl acetate, whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the mixed solvent of 50 grams of Asparagus cochinchinensis ammonia acid sodiums and 60 milliliters of acetone and water, it is 10 that the sodium hydroxide solution that is 20% by concentration regulates PH, under fully stirring, slowly add again the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides and 20% sodium hydroxide solution in batches, make temperature of reaction system be controlled at 5 DEG C～10 DEG C, it is 9～10 that PH controls, after the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides adds, being warming up to 25 DEG C～35 DEG C reacts 3 hours, it is 9～10 that PH controls, be warming up to again 45 DEG C～65 DEG C and continue reaction 2 hours, it is 9～10 that PH controls, generate the two Asparagus cochinchinensis ammonia acid sodiums of positive 11 carbon diacyls, after completion of the reaction, Distillation recovery acetone, reaction mass water dilutes, and slowly adds acid solution, adjusts PH to 1.0 left and right, separates out solid product, and water repetitive scrubbing product obtains the just two aspartic acids of 11 carbon diacyls, two positive 11 carbon diacyls aspartic acids are joined in 80 grams of diglycolamines, and stirring and dissolving, makes positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt.
Embodiment 3
40 grams of positive DC11s and 44 grams of ethyl acetate are put in corrosion-resistant reactor, add 1.2 grams of N, dinethylformamide, add 44 grams of new sulfur oxychlorides that steam, under stirring, 80 DEG C～85 DEG C back flow reaction 5 hours, tail gas alkali liquor absorption, generated positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides, after completion of the reaction, Distillation recovery ethyl acetate, whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the mixed solvent of 45 grams of Asparagus cochinchinensis ammonia acid sodiums and 55 milliliters of acetone and water, it is 10 that the sodium hydroxide solution that is 20% by concentration regulates PH, under fully stirring, slowly add again the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides and 20% sodium hydroxide solution in batches, make temperature of reaction system be controlled at 5 DEG C～10 DEG C, it is 9～10 that PH controls, after the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides adds, being warming up to 25 DEG C～35 DEG C reacts 3 hours, it is 9～10 that PH controls, be warming up to again 45 DEG C～65 DEG C and continue reaction 3 hours, it is 9～10 that PH controls, generate the two Asparagus cochinchinensis ammonia acid sodiums of positive 11 carbon diacyls, after completion of the reaction, Distillation recovery acetone, reaction mass water dilutes, and slowly adds acid solution, adjusts PH to 1.0 left and right, separates out solid product, and water repetitive scrubbing product obtains the just two aspartic acids of 11 carbon diacyls, two positive 11 carbon diacyls aspartic acids are joined in 78 grams of diglycolamines, and stirring and dissolving, makes positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt.
The above; embodiment is only that the preferred embodiment of the present invention is described; not scope of the present invention is limited; under the prerequisite of spirit that does not depart from the technology of the present invention; various distortion and improvement that this area engineering technical personnel make technical scheme of the present invention, all should fall in the definite protection domain of claims of the present invention.
Claims (2)
1. positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt is synthetic, it is characterized in that: taking ethyl acetate as solvent, positive DC11 carries out back flow reaction with the new sulfur oxychloride steaming under catalyst action, generates positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydride mixtures; Under acid binding agent exists, the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides reacts with Asparagus cochinchinensis ammonia acid sodium in the mixed solvent of acetone and water, generates positive 11 carbon diacyls pair Asparagus cochinchinensis ammonia acid sodiums; After reaction mass dilute with water, pickling and washing, obtain the just two aspartic acids of 11 carbon diacyls, then join in diglycolamine, stirring and dissolving, makes positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt; Specifically comprise following steps:
1). taking ethyl acetate as solvent, positive DC11 and the new sulfur oxychloride steaming in molar ratio 1 ﹕ 1.5～2.5 feed intake, N, dinethylformamide is catalyzer, under stirring, 80 DEG C～85 DEG C back flow reaction 4～7 hours, tail gas alkali liquor absorption, generated positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides, after completion of the reaction, Distillation recovery ethyl acetate;
2). under acid binding agent exists, the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides, slowly join in the acetone of Asparagus cochinchinensis ammonia acid sodium and the mixed solvent of water in batches, make temperature of reaction system be controlled at 5 DEG C～10 DEG C, after the mixture of positive 11 carbon diacid chlorides and positive 11 carbon dicarboxylic anhydrides adds, being warming up to 25 DEG C～35 DEG C reacts 2～3 hours, be warming up to 45 DEG C～65 DEG C continuation reactions 2～3 hours, generate the two Asparagus cochinchinensis ammonia acid sodiums of positive 11 carbon diacyls, after completion of the reaction, Distillation recovery acetone;
3). resultant of reaction water dilutes, and slowly adds acid solution, adjusts PH to 1.0 left and right, separates out solid product, and water repetitive scrubbing product obtains the just two aspartic acids of 11 carbon diacyls;
4). two positive 11 carbon diacyls aspartic acids are joined in diglycolamine, be heated to 40 DEG C～50 DEG C, stirring and dissolving, makes positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt.
2. a kind of positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt according to claim 1 is synthetic, it is characterized in that: described ethyl acetate consumption is 100%～120% of positive DC11 consumption; Described DMF catalyst levels is 1%～5% of positive DC11 consumption; Described alkali lye is aqueous sodium carbonate; Described acetone and the volume ratio of water are 1 ﹕ 1; Described Asparagus cochinchinensis ammonia acid sodium is 1 ﹕ 1.5～2 with the mol ratio of positive DC11; Described acid solution is sulphuric acid soln or hydrochloric acid soln; The mol ratio of the two aspartic acids of described positive 11 carbon diacyls and diglycolamine is 1 ﹕ 4～6.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111039811A (en) * | 2019-12-23 | 2020-04-21 | 四川欣美加生物医药有限公司 | Process for preparing nonane diacyl amino acid salt |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101903336A (en) * | 2007-11-20 | 2010-12-01 | 科莱恩金融(Bvi)有限公司 | Method for producing acylglycinates |
| CN102863348A (en) * | 2012-09-05 | 2013-01-09 | 长沙普济生物科技有限公司 | Synthesis method of palmitoyl amino acid sodium |
| CN103130675A (en) * | 2011-11-23 | 2013-06-05 | 苏州维美生物科技有限公司 | Industrial production method of high-purity N-lauroyl-L-alanine surfactant |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101903336A (en) * | 2007-11-20 | 2010-12-01 | 科莱恩金融(Bvi)有限公司 | Method for producing acylglycinates |
| CN103130675A (en) * | 2011-11-23 | 2013-06-05 | 苏州维美生物科技有限公司 | Industrial production method of high-purity N-lauroyl-L-alanine surfactant |
| CN102863348A (en) * | 2012-09-05 | 2013-01-09 | 长沙普济生物科技有限公司 | Synthesis method of palmitoyl amino acid sodium |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111039811A (en) * | 2019-12-23 | 2020-04-21 | 四川欣美加生物医药有限公司 | Process for preparing nonane diacyl amino acid salt |
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