CN104649927A - N-undecane diacyl diglutamic acid triethanolamine salt and preparation method thereof - Google Patents
N-undecane diacyl diglutamic acid triethanolamine salt and preparation method thereof Download PDFInfo
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- CN104649927A CN104649927A CN201310598571.5A CN201310598571A CN104649927A CN 104649927 A CN104649927 A CN 104649927A CN 201310598571 A CN201310598571 A CN 201310598571A CN 104649927 A CN104649927 A CN 104649927A
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- undecane
- diacyl
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- acid
- glutamic acid
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- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 239000002253 acid Substances 0.000 title claims abstract description 23
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 claims abstract description 15
- 235000013923 monosodium glutamate Nutrition 0.000 claims abstract description 14
- 229940073490 sodium glutamate Drugs 0.000 claims abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000012046 mixed solvent Substances 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 claims abstract description 8
- 239000012265 solid product Substances 0.000 claims abstract description 8
- 238000006467 substitution reaction Methods 0.000 claims abstract description 8
- 239000011230 binding agent Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 229960002989 glutamic acid Drugs 0.000 claims description 14
- TUBPSFQENHCYBW-HVDRVSQOSA-N (2s)-2-aminopentanedioic acid;2-[bis(2-hydroxyethyl)amino]ethanol Chemical compound OC(=O)[C@@H](N)CCC(O)=O.OCCN(CCO)CCO TUBPSFQENHCYBW-HVDRVSQOSA-N 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000005457 ice water Substances 0.000 claims description 10
- 229960004418 trolamine Drugs 0.000 claims description 9
- 230000003252 repetitive effect Effects 0.000 claims description 7
- 238000005201 scrubbing Methods 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000010790 dilution Methods 0.000 claims description 5
- 239000012895 dilution Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011575 calcium Substances 0.000 abstract description 2
- 229910001425 magnesium ion Inorganic materials 0.000 abstract description 2
- 229910001424 calcium ion Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000008233 hard water Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 244000248539 Asparagus cochinchinensis Species 0.000 description 3
- 235000009292 Asparagus cochinchinensis Nutrition 0.000 description 3
- 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 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 238000005555 metalworking Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- -1 alcohol amine salt Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses an n-undecane diacyl diglutamic acid triethanolamine salt and its preparation method. The preparation method is characterized by comprising the following steps: with water and acetone used as a mixed solvent and in the presence of an acid-binding agent, n-undecane diacid chloride and sodium glutamate undergo a substitution reaction by cold water bath so as to generate n-undecane diacyl disodium glutamate; reaction materials are diluted with water, acid liquor is slowly added to adjust pH to about 1.0, a solid product is precipitated out, and the product is repeatedly washed with water so as to obtain n-undecane diacyl diglutamic acid; with a few amount of water used as a solvent, n-undecane diacyl diglutamic acid reacts with triethanolamine; and after a solution is transparent, distillation is carried out to remove moisture so as to prepare the n-undecane diacyl diglutamic acid triethanolamine salt. The compound has an effect of forming a stable complex with calcium and magnesium ion and can soften hard water.
Description
Technical field
The present invention relates to rust-inhibiting additive synthesis technical field, espespecially a kind of n-undecane diacyl two L-glutamic acid triethanolamine salt and preparation method thereof.
Background technology
Water-based metal working fluid is because having the advantages such as excellent cooling, cleaning, rust-preventing characteristic, economy and security, be developed rapidly, and be widely used in the metal processing sectors such as cutting, grinding, calendering, punching press and tapping, rust-inhibiting additive is the important component part of water-based metal working fluid, along with the development and application of organic rust preventing additive, inorganic salts rust-inhibiting additive is substituted gradually, and carboxyl is the essential groups of natural organic ligand and melts combine.Rust-inhibiting additive plays the effect preventing from corroding in process of metal working; polar group in rust-inhibiting additive molecule can be adsorbed in metallic surface; and hydrophobic alkyl forms protective membrane in metallic surface; play rust-proof effect; the solvability of organic molecule in water is relevant with the hydrophilic radical of alkyl chain; as water miscible rust-inhibiting additive, in molecule, not only to there is the polar group playing rust inhibition, and will have certain water-soluble.Along with improving constantly of modern machinery and equipment performance, environmental requirement is increasingly harsh, needs to use high performance rust-inhibiting additive in production, life.
Summary of the invention
The object of the present invention is to provide a kind of n-undecane diacyl two L-glutamic acid triethanolamine salt and preparation method thereof.
Technical solution of the present invention is: with water and acetone for mixed solvent, under acid binding agent exists, n-undecane diacid chloride and Sodium Glutamate, substitution reaction is carried out in ice-water bath, generate n-undecane diacyl two Sodium Glutamate, reaction mass water dilutes, slowly add acid solution, adjust about PH to 1.0, separate out solid product, with water repetitive scrubbing product, obtain n-undecane diacyl two L-glutamic acid, with a small amount of water for solvent, n-undecane diacyl two L-glutamic acid and trolamine react again, after solution is transparent, carry out dephlegmate again to divide, obtained n-undecane diacyl two L-glutamic acid triethanolamine salt, specifically comprise following steps:
1). with water and acetone for mixed solvent; under acid binding agent exists; PH remains on 8 ~ 10; n-undecane diacid chloride (I) and Sodium Glutamate (II) in ice-water bath at the temperature of 5 DEG C ~ 15 DEG C; carry out substitution reaction 2 ~ 3 hours; generate n-undecane diacyl two Sodium Glutamate (III), its main chemical reactions is:
2). reaction mass water dilutes, and slowly adds acid solution, adjusts about PH to 1.0, and separate out solid product, with water repetitive scrubbing product, obtain n-undecane diacyl two L-glutamic acid (IV), its main chemical reactions is:
3). with a small amount of water for solvent; n-undecane diacyl two L-glutamic acid (IV) and trolamine; stirring reaction 1 ~ 2 hour at 40 DEG C ~ 60 DEG C temperature; after solution is transparent; carry out dephlegmate again to divide; obtained n-undecane diacyl two L-glutamic acid triethanolamine salt (V), its main chemical reactions is:
Further, described water and the volume ratio of acetone are 1 ﹕ 1 ~ 1.5.
The mol ratio of described n-undecane diacid chloride, Sodium Glutamate and trolamine is 1 ﹕ 1 ﹕ 2 ~ 2.4.
Described acid binding agent is one or more in sodium bicarbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, saleratus, salt of wormwood and sodium hydroxide and saturated solution thereof.
Described acid solution is dilution heat of sulfuric acid or dilute hydrochloric acid solution.
A kind of n-undecane diacyl two of the present invention L-glutamic acid triethanolamine salt and preparation method thereof, its feature and advantage are: sufficient raw, and cost is lower; Synthetics is a kind of alcohol amine salt of organic heterocyclic polycarboxylic acid, has the characteristic of multiple carboxyl and melts combine, can play excellent rust inhibition; Synthetics has the effect of the stable comple formed with calcium, magnesium ion, can softening of water; Operation is simple, is applicable to suitability for industrialized production.
Embodiment
Embodiment 1
In the four-hole bottle that whipping appts, reflux condensate device and thermometer are housed, add 80mL water and 80mL acetone mixed solvent, add the Sodium Glutamate of 14.7 grams, stirring makes it to dissolve completely, 0 DEG C ~ 10 DEG C are cooled to ice-water bath, drip 22 grams of n-undecane diacid chlorides, remain on 8 ~ 10 with sodium hydroxide solution regulation system PH simultaneously, after dripping n-undecane diacid chloride, in ice-water bath at the temperature of maintenance 5 DEG C ~ 15 DEG C, continue stirring and carry out substitution reaction 2 ~ 3 hours, generate n-undecane diacyl two Asparagus cochinchinensis ammonia acid sodium; In four-hole bottle, add 100mL water makes reaction mass dilute, and slowly adds dilution heat of sulfuric acid, adjusts about PH to 1.0, separates out solid product, with water repetitive scrubbing product, obtains n-undecane diacyl two L-glutamic acid; The trolamine of 100mL water, obtained n-undecane diacyl two L-glutamic acid and 26 grams is added in four-hole bottle; stirring reaction 1 ~ 2 hour at 45 DEG C ~ 55 DEG C temperature; after solution is transparent, then carries out dephlegmate and divide, obtained n-undecane diacyl two L-glutamic acid triethanolamine salt.
Embodiment 2
In the four-hole bottle that whipping appts, reflux condensate device and thermometer are housed, add 80mL water and 90mL acetone mixed solvent, add the Sodium Glutamate of 16 grams, stirring makes it to dissolve completely, 0 DEG C ~ 10 DEG C are cooled to ice-water bath, drip 24 grams of n-undecane diacid chlorides, remain on 8 ~ 10 with saturated sodium carbonate solution regulation system PH simultaneously, after dripping n-undecane diacid chloride, in ice-water bath at the temperature of maintenance 5 DEG C ~ 15 DEG C, continue stirring and carry out substitution reaction 2 ~ 3 hours, generate n-undecane diacyl two Asparagus cochinchinensis ammonia acid sodium; In four-hole bottle, add 100mL water makes reaction mass dilute, and slowly adds dilution heat of sulfuric acid, adjusts about PH to 1.0, separates out solid product, with water repetitive scrubbing product, obtains n-undecane diacyl two L-glutamic acid; The trolamine of 100mL water, obtained n-undecane diacyl two L-glutamic acid and 31 grams is added in four-hole bottle; stirring reaction 1 ~ 2 hour at 40 DEG C ~ 50 DEG C temperature; after solution is transparent, then carries out dephlegmate and divide, obtained n-undecane diacyl two L-glutamic acid triethanolamine salt.
Embodiment 3
In the four-hole bottle that whipping appts, reflux condensate device and thermometer are housed, add 70mL water and 100mL acetone mixed solvent, add the Sodium Glutamate of 14.7 grams, stirring makes it to dissolve completely, 0 DEG C ~ 10 DEG C are cooled to ice-water bath, drip 22 grams of n-undecane diacid chlorides, remain on 8 ~ 10 with saturated sodium carbonate solution regulation system PH simultaneously, after dripping n-undecane diacid chloride, in ice-water bath at the temperature of maintenance 5 DEG C ~ 15 DEG C, continue stirring and carry out substitution reaction 2 ~ 3 hours, generate n-undecane diacyl two Asparagus cochinchinensis ammonia acid sodium; In four-hole bottle, add 100mL water makes reaction mass dilute, and slowly adds dilution heat of sulfuric acid, adjusts about PH to 1.0, separates out solid product, with water repetitive scrubbing product, obtains n-undecane diacyl two L-glutamic acid; The trolamine of 100mL water, obtained n-undecane diacyl two L-glutamic acid and 36.5 grams is added in four-hole bottle; stirring reaction 1 ~ 2 hour at 50 DEG C ~ 60 DEG C temperature; after solution is transparent, then carries out dephlegmate and divide, obtained n-undecane diacyl two L-glutamic acid triethanolamine salt.
The above; embodiment is only be described the preferred embodiment of the present invention; not scope of the present invention is limited; under the prerequisite of spirit not departing from the technology of the present invention; the various distortion that this area engineering technical personnel make technical scheme of the present invention and improvement, all should fall in protection domain that claims of the present invention determine.
Claims (2)
1. n-undecane diacyl two L-glutamic acid triethanolamine salt and preparation method thereof, it is characterized in that: with water and acetone for mixed solvent, under acid binding agent exists, n-undecane diacid chloride and Sodium Glutamate, substitution reaction is carried out in ice-water bath, generate n-undecane diacyl two Sodium Glutamate, reaction mass water dilutes, slowly add acid solution, adjust about PH to 1.0, separate out solid product, with water repetitive scrubbing product, obtain n-undecane diacyl two L-glutamic acid, with a small amount of water for solvent, n-undecane diacyl two L-glutamic acid and trolamine react again, after solution is transparent, carry out dephlegmate again to divide, obtained n-undecane diacyl two L-glutamic acid triethanolamine salt, specifically comprise following steps:
1). with water and acetone for mixed solvent, acid binding agent exist under, PH remains on 8 ~ 10, n-undecane diacid chloride and Sodium Glutamate in ice-water bath at the temperature of 5 DEG C ~ 15 DEG C, carry out substitution reaction 2 ~ 3 hours, generate n-undecane diacyl two Sodium Glutamate;
2). reaction mass water dilutes, and slowly adds acid solution, adjusts about PH to 1.0, separates out solid product, with water repetitive scrubbing product, obtains n-undecane diacyl two L-glutamic acid;
3). with a small amount of water for solvent; n-undecane diacyl two L-glutamic acid and trolamine, stirring reaction 1 ~ 2 hour at 40 DEG C ~ 60 DEG C temperature, after solution is transparent; carry out dephlegmate again to divide, obtained n-undecane diacyl two L-glutamic acid triethanolamine salt.
2. a kind of n-undecane diacyl two L-glutamic acid triethanolamine salt according to claim 1 and preparation method thereof, is characterized in that: the mol ratio of described n-undecane diacid chloride, Sodium Glutamate and trolamine is 1 ﹕ 1 ﹕ 2 ~ 2.4; Described acid binding agent is one or more in sodium bicarbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, saleratus, salt of wormwood and sodium hydroxide and saturated solution thereof; Described acid solution is dilution heat of sulfuric acid or dilute hydrochloric acid solution.
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| CN201310598571.5A CN104649927B (en) | 2013-11-25 | 2013-11-25 | A kind of glutamic acid triethanolamine salt of n-undecane diacyl two and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111099A (en) * | 2015-08-24 | 2015-12-02 | 长沙普济生物科技有限公司 | Solid and liquid synthesis method of N-lauroyl glycine triethanolamine salt solution |
| CN109942450A (en) * | 2019-03-27 | 2019-06-28 | 南京华狮新材料有限公司 | It is amino acid type chelated dose a kind of and its preparation method and application |
| 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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Cited By (3)
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| CN105111099A (en) * | 2015-08-24 | 2015-12-02 | 长沙普济生物科技有限公司 | Solid and liquid synthesis method of N-lauroyl glycine triethanolamine salt solution |
| CN109942450A (en) * | 2019-03-27 | 2019-06-28 | 南京华狮新材料有限公司 | It is amino acid type chelated dose a kind of and its preparation method and application |
| 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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Inventor after: Wang Liwei Inventor after: Wang Ying Inventor after: Wang Lufei Inventor before: Liu Xianmei |
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Effective date of registration: 20170925 Address after: Baiding town Haian County 226600 Jiangsu city of Nantong Province Liu Jicun happy group Applicant after: Jiangsu Sixin Surfactant Technology Co., Ltd. Address before: 510640 Guangdong City, Tianhe District Province, No. five, road, public education building, unit 371-1, unit 2401 Applicant before: Guangdong Gaohang Intellectual Property Operation Co., Ltd. |
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Granted publication date: 20171031 Termination date: 20171125 |