CN104649926B - Two asparatate of a kind of N, N '-decanedioyl base and preparation method thereof - Google Patents
Two asparatate of a kind of N, N '-decanedioyl base and preparation method thereof Download PDFInfo
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- CN104649926B CN104649926B CN201310597962.5A CN201310597962A CN104649926B CN 104649926 B CN104649926 B CN 104649926B CN 201310597962 A CN201310597962 A CN 201310597962A CN 104649926 B CN104649926 B CN 104649926B
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- asparatate
- base
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- water
- sodium
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- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 24
- 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 claims abstract description 21
- 239000011734 sodium Substances 0.000 claims abstract description 21
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 21
- 244000248539 Asparagus cochinchinensis Species 0.000 claims abstract description 19
- 235000009292 Asparagus cochinchinensis Nutrition 0.000 claims abstract description 19
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000005457 ice water Substances 0.000 claims abstract description 11
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006386 neutralization reaction Methods 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
- 239000011230 binding agent Substances 0.000 claims abstract description 7
- 238000006467 substitution reaction Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims 6
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 1
- 229960001230 asparagine Drugs 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 3
- 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
- 229910001424 calcium ion Inorganic materials 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 229910001425 magnesium ion Inorganic materials 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 decanedioyl Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005555 metalworking Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kind of N, two asparatate of N ' decanedioyls base and preparation method thereof, it is characterized in that：Using water as solvent, asparatate carries out acid-base neutralization reaction with sodium hydroxide, produce Asparagus cochinchinensis ammonia acid sodium, in the presence of acid binding agent, sebacoyl chloride and Asparagus cochinchinensis ammonia acid sodium, substitution reaction is carried out in ice-water bath, generate N, two Asparagus cochinchinensis ammonia acid sodium of N ' decanedioyls base, reaction mass is diluted with water, it is slowly added to acid solution, adjust PH to 1.0 or so, solid product is precipitated, with water washed product repeatedly, obtain N, two asparatate of N ' decanedioyls base, synthetic is a kind of organic polycarboxylic acid, the characteristic combined with metal with multiple carboxyls, excellent anti-rust action can be played；Synthetic has the function of the stable comple formed with calcium and magnesium ion.
Description
Technical field
The present invention relates to rust-inhibiting additive synthesis technical field, espespecially a kind of N, two asparatate of N '-decanedioyls base and
Preparation method.
Background technology
Rust-inhibiting additive is a kind of important additives in metal working fluid, and being played in process of metal working prevents from corroding
Effect, the polar group in rust-inhibiting additive molecule can be adsorbed in metal surface, and hydrophobic alkyl is formed in metal surface
Protective film plays rust-proof effect, and the dissolubility of organic molecule in water is related with the hydrophilic radical of alkyl chain, as water solubility
Rust-inhibiting additive, not only to have the polar group for playing anti-rust action in molecule, and to have certain water solubility.
With the continuous improvement of modern machinery and equipment performance, environmental requirement is increasingly harsh, is needed using height in production, life
The rust-inhibiting additive of performance not only has higher requirements to rust-preventing characteristic, water solubility, also has requirements at the higher level to lubricity, stability in hard water.
Invention content
The purpose of the present invention is to provide a kind of N, two asparatates of N '-decanedioyls base and preparation method thereof.
Technical solution of the invention is：Using water as solvent, asparatate and sodium hydroxide progress acid-base neutralization are anti-
It answers, produces Asparagus cochinchinensis ammonia acid sodium, in the presence of acid binding agent, sebacoyl chloride and Asparagus cochinchinensis ammonia acid sodium are replaced in ice-water bath
Reaction generates N, two Asparagus cochinchinensis ammonia acid sodium of N '-decanedioyls base, and reaction mass is diluted with water, is slowly added to acid solution, adjusts pH extremely
1.0 or so, solid product is precipitated, with water washed product repeatedly, obtains N, two asparatate of N '-decanedioyls base, it is specific comprising with
Lower step：
1) is using water as solvent, asparatate（Ⅰ）Acid-base neutralization reaction is carried out with sodium hydroxide, produces asparatate
Sodium（Ⅱ）Solution, main chemical reactions are：
2) is in the presence of acid binding agent, sebacoyl chloride（Ⅲ）With Asparagus cochinchinensis ammonia acid sodium（Ⅱ）Solution, 5 DEG C in ice-water bath~
Substitution reaction 2~3 hours is carried out at 15 DEG C, generates N, two Asparagus cochinchinensis ammonia acid sodium of N '-decanedioyls base（Ⅳ）, main chemical reactions
For：
3) reaction masses are diluted with water, are slowly added to acid solution, adjust pH to 1.0 or so, and solid product is precipitated, uses water
Washed product repeatedly obtains N, two asparatate of N '-decanedioyls base（Ⅴ）, main chemical reactions are：
Further, the molar ratio of the asparatate and sodium hydroxide is 1 ﹕ 2~2.5.
The acid binding agent is sodium bicarbonate solution or sodium carbonate liquor.
The sebacoyl chloride is 1 ﹕ 2 with asparatate molar ratio.
The acid solution is sulfuric acid solution or hydrochloric acid solution.
A kind of N of the present invention, two asparatate of N '-decanedioyls base and preparation method thereof, features and advantages are：Raw material comes
Source is sufficient, and cost is relatively low；Synthetic is a kind of organic polycarboxylic acid, with the characteristic that multiple carboxyls are combined with metal, can be played
Excellent anti-rust action；Synthetic has the function of the stable comple formed with calcium and magnesium ion, can be with softening of water；Reaction
Operation is simple, is suitble to industrialized production.
Specific implementation mode
Embodiment 1
In the four-hole bottle equipped with agitating device, reflux condensate device and thermometer, 100mL water is added, 60 grams of days are added
L-aminobutanedioic acid and 36 grams of sodium hydroxides carry out acid-base neutralization reaction, produce Asparagus cochinchinensis ammonia acid sodium, 0 DEG C~10 are cooled to ice-water bath
DEG C, 54 grams of sebacoyl chlorides are added dropwise, while 8~10 are maintained at sodium carbonate liquor regulation system pH, after dripping sebacoyl chloride,
In ice-water bath at a temperature of being kept for 5 DEG C~10 DEG C, continues stirring and carry out substitution reaction 2~3 hours, generate N, N '-decanedioyls
Two Asparagus cochinchinensis ammonia acid sodium of base；100mL water is added into four-hole bottle makes reaction mass dilute, and is slowly added to sulfuric acid solution, adjusts pH extremely
1.0 or so, solid product is precipitated, with water washed product repeatedly, obtains N, N, the N '-last of the ten Heavenly stems is made in two asparatate of N '-decanedioyls base
Two asparatate of diacyl.
Embodiment 2
In the four-hole bottle equipped with agitating device, reflux condensate device and thermometer, 150mL water is added, 65 grams of days are added
L-aminobutanedioic acid and 44 grams of sodium hydroxides carry out acid-base neutralization reaction, produce Asparagus cochinchinensis ammonia acid sodium, 5 DEG C~15 are cooled to ice-water bath
DEG C, 58 grams of sebacoyl chlorides are added dropwise, while 8~10 are maintained at sodium bicarbonate solution regulation system pH, after dripping sebacoyl chloride,
In ice-water bath at a temperature of being kept for 5 DEG C~15 DEG C, continues stirring and carry out substitution reaction 2~3 hours, generate N, the N '-last of the ten Heavenly stems two
Two Asparagus cochinchinensis ammonia acid sodium of acyl group；100mL water is added into four-hole bottle makes reaction mass dilute, and is slowly added to sulfuric acid solution, adjusts pH
To 1.0 or so, solid product is precipitated, with water washed product repeatedly, obtains N, N, N '-is made in two asparatate of N '-decanedioyls base
Two asparatate of decanedioyl base.
Embodiment 3
In the four-hole bottle equipped with agitating device, reflux condensate device and thermometer, 200mL water is added, 70 grams of days are added
L-aminobutanedioic acid and 52 grams of sodium hydroxides carry out acid-base neutralization reaction, produce Asparagus cochinchinensis ammonia acid sodium, 5 DEG C~10 are cooled to ice-water bath
DEG C, 62 grams of sebacoyl chlorides are added dropwise, while 8~10 are maintained at sodium bicarbonate solution regulation system pH, after dripping sebacoyl chloride,
In ice-water bath at a temperature of being kept for 5 DEG C~15 DEG C, continues stirring and carry out substitution reaction 2~3 hours, generate N, the N '-last of the ten Heavenly stems two
Two Asparagus cochinchinensis ammonia acid sodium of acyl group；150mL water is added into four-hole bottle makes reaction mass dilute, and is slowly added to hydrochloric acid solution, adjusts pH
To 1.0 or so, solid product is precipitated, with water washed product repeatedly, obtains N, N, N '-is made in two asparatate of N '-decanedioyls base
Two asparatate of decanedioyl base.
The above, embodiment is only that the preferred embodiment of the present invention is described, not to the present invention's
Range is defined, under the premise of not departing from the spirit of the technology of the present invention, skill of this field engineers and technicians to the present invention
The various modifications and improvement that art scheme is made should all be fallen into the protection domain of claims of the present invention determination.
Claims (2)
1. a kind of preparation method of two asparatate of N, N '-decanedioyl base, it is characterized in that：Using water as solvent, asparatate
Acid-base neutralization reaction is carried out with sodium hydroxide, produces Asparagus cochinchinensis ammonia acid sodium, in the presence of acid binding agent, sebacoyl chloride and asparagine
Sour sodium carries out substitution reaction in ice-water bath, generates N, two Asparagus cochinchinensis ammonia acid sodium of N '-decanedioyls base, and reaction mass is carried out with water
Dilution, is slowly added to acid solution, adjusts pH to 1.0 or so, and solid product is precipitated, and with water washed product repeatedly, obtains N, N '-decanedioyl bases
Two asparatates, specifically comprise the steps of：
1) is using water as solvent, asparatate（Ⅰ）Acid-base neutralization reaction is carried out with sodium hydroxide, produces Asparagus cochinchinensis ammonia acid sodium
（Ⅱ）Solution, chemical reaction are：
；
2) is in the presence of acid binding agent, sebacoyl chloride（Ⅲ）With Asparagus cochinchinensis ammonia acid sodium（Ⅱ）Solution, 5 DEG C~15 DEG C in ice-water bath
Lower progress substitution reaction 2~3 hours generates N, two Asparagus cochinchinensis ammonia acid sodium of N '-decanedioyls base（Ⅳ）, chemical reaction be：
；
3) reaction masses are diluted with water, are slowly added to acid solution, adjust pH to 1.0 or so, solid product are precipitated, repeatedly with water
Washed product obtains N, two asparatate of N '-decanedioyls base（Ⅴ）, chemical reaction be：
。
2. a kind of N according to claim 1, the preparation method of two asparatate of N '-decanedioyls base, it is characterized in that：Institute
The molar ratio of the asparatate and sodium hydroxide stated is 1 ﹕ 2~2.5；The acid binding agent is sodium bicarbonate solution or sodium carbonate
Solution；The sebacoyl chloride is 1 ﹕ 2 with asparatate molar ratio.
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| CN201310597962.5A CN104649926B (en) | 2013-11-25 | 2013-11-25 | Two asparatate of a kind of N, N '-decanedioyl base and preparation method thereof |
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| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993021913A1 (en) * | 1992-04-28 | 1993-11-11 | Senyorina Ltd. | Anti-obesity drugs |
| WO2007127198A2 (en) * | 2006-04-24 | 2007-11-08 | Incept, Llc | Protein crosslinkers, crosslinking methods and applications thereof |
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- 2013-11-25 CN CN201310597962.5A patent/CN104649926B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993021913A1 (en) * | 1992-04-28 | 1993-11-11 | Senyorina Ltd. | Anti-obesity drugs |
| WO2007127198A2 (en) * | 2006-04-24 | 2007-11-08 | Incept, Llc | Protein crosslinkers, crosslinking methods and applications thereof |
Non-Patent Citations (1)
| Title |
|---|
| N-十二酰基天冬氨酸及其钠盐的合成与性能;王军 等;《精细石油化工》;20100930;第27卷(第5期);44-48 * |
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Effective date of registration: 20201201 Address after: Tao Yuan Ji Zhen Tao Yuan Hou Dong Jie Cun, Cao County, Heze City, Shandong Province Patentee after: Caoxian runran Wood Industry Co., Ltd Address before: 264006 No. 3, building 18, Fengtai District, Yantai Development Zone, Shandong 8, China Patentee before: Liu Xianmei |
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