CN104649989A - Tri(aspartic acid amido)-s-triazine and preparation method thereof - Google Patents
Tri(aspartic acid amido)-s-triazine and preparation method thereof Download PDFInfo
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- CN104649989A CN104649989A CN201310598146.6A CN201310598146A CN104649989A CN 104649989 A CN104649989 A CN 104649989A CN 201310598146 A CN201310598146 A CN 201310598146A CN 104649989 A CN104649989 A CN 104649989A
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- Prior art keywords
- triazine
- amino
- succinic acid
- alkali
- aspartic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Catalysts (AREA)
Abstract
The invention discloses tri(aspartic acid amido)-s-triazine and its preparation method. The preparation method is characterized in that aspartic acid and hydroxide of alkali metal undergo acid-base neutralization to prepare aspartate; aspartate and cyanuric chloride reacts under the catalytic action of alkali metal hydroxide to generate a tri(aminosuccinate)-s-triazine compound; and after the tri(aminosuccinate)-s-triazine compound undergoes acidification, the acidized compound reacts with hydroxyalkyl secondary amine under the action of a catalyst to generate a tri(aspartic acid amido)-s-triazine rust-inhibiting additive. Sources of raw materials are sufficient, and costs are low. The composition is an organic heterocyclic multi-amide, has high resistance to hard water, has characteristics of multiple amino groups and amide groups binding to metal, and has an excellent rust-inhibiting effect. Reaction operation is simple and feasible. The preparation method is suitable for industrial production.
Description
Technical field
The present invention relates to organic rust preventing additive synthesis technical field, espespecially a kind of three (amino-succinic acid amide group) – s-triazine and preparation method thereof.
Background technology
Water-based metal working fluid is because having excellent cooling, cleaning, rust-preventing characteristic, the advantage such as economy and security, be developed rapidly, and be widely used in cutting, grinding, calendering, the metal processing sectors such as 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, carboxyl is the essential groups of natural organic ligand and melts combine, the size of its corrosion inhibition, depend primarily on molecular structure, in metallic surface, keying action is played to molecular adsorption.
Cyanuric chloride is a kind of abundance of originating, has the industrial chemicals of stable triazine chemical structure, by functional group and reaction, by functional group and reaction, can synthesize outstanding rust-inhibiting additive.
Summary of the invention
The object of the present invention is to provide a kind of three (amino-succinic acid amide group) – s-triazine rust-inhibiting additives and preparation method thereof.
Technical solution of the present invention is: aspartic acid and alkali-metal oxyhydroxide carry out acid-base neutralisation reaction, produce aspartate, aspartate and cyanuric chloride, under alkali-metal hydroxide-catalyzed effect, its reaction generate three (amino-succinic acid alkali) – s-triazine is after acidifying, react under catalyst action with hydroxy-alkyl secondary again, generate three (amino-succinic acid amide group) – s-triazine rust-inhibiting additive, specifically comprises following steps:
1). take water as solvent, aspartic acid (I) and alkali-metal oxyhydroxide carry out acid-base neutralisation reaction, and produce aspartic acid salts solution (II), its main chemical reactions is:
Described alkali-metal oxyhydroxide MOH be selected from sodium hydroxide and potassium hydroxide one or both.
2). cyanuric chloride (III) and aspartic acid salts solution (II) are under alkali-metal hydroxide-catalyzed effect, react 3 ~ 5 hours at 60 DEG C ~ 80 DEG C, generate intermediate compound three (amino-succinic acid alkali) – s-triazine (IV), its main chemical reactions is:
3). three (amino-succinic acid alkali) – s-triazine (IV) in acid condition, at 20 ~ 40 DEG C, carry out acidification reaction 1 ~ 2 hour, filter, get filter cake, obtained three (amino-succinic acid) – s-triazine (V), its main chemical reactions is:
4). three (amino-succinic acid) – s-triazine (V) and hydroxy-alkyl secondary (VI), a small amount of water is solvent, under ammonium ferric sulfate catalyst effect, react 5 ~ 7 hours at 140 DEG C ~ 160 DEG C temperature, slowly be cooled to 70 ~ 80 DEG C, continue stirring 1 ~ 2 hour, remove moisture under reduced pressure, obtained three (amino-succinic acid amide group) – s-triazine rust-inhibiting additive (VII), its main chemical reactions is:
In formula, R
1and R
2the short chain hydroxyalkyls such as hydroxyethyl independent of each other, hydroxypropyl, hydroxyl sec.-propyl, hydroxyl butyl or hydroxyl isobutyl-.
Further: the mol ratio of described cyanuric chloride, aspartic acid, alkali-metal oxyhydroxide and hydroxy-alkyl secondary is 1 ﹕ 3 ~ 4 ﹕ 5 ~ 7 ﹕ 6 ~ 8.
Described ammonium ferric sulfate catalyst, its consumption is 0.5% ~ 1.5% of hydroxy-alkyl secondary consumption.
One of the present invention three (amino-succinic acid amide group) – s-triazine and preparation method thereof, its feature and advantage are: sufficient raw, and cost is lower; Synthetics is the polynary acid amides of a kind of organic heterocyclic, and stability in hard water can be high; There is the characteristic of multiple amino and amide group and melts combine, excellent rust inhibition can be played; Operation is simple, is applicable to suitability for industrialized production.
Embodiment
Embodiment 1
In the there-necked flask that whipping appts and thermometer are housed, add 80mL water, the aspartic acid and the 20 grams of sodium hydroxide that add 100 grams carry out acid-base neutralisation reaction, after solution clarification, produce aspartic acid sodium solution, add 45.5 grams of cyanuric chlorides, add the sodium hydroxide of 30 grams, react 3 ~ 5 hours at 60 DEG C ~ 80 DEG C, generate intermediate compound three (amino-succinic acid sodium base) – s-triazine, dripping sulfuric acid adjusts pH value to be about 1, at 20 ~ 40 DEG C, carry out acidification reaction 1 ~ 2 hour, filter, get filter cake, obtained three (amino-succinic acid) – s-triazine, by obtained three, (amino-succinic acid) – s-triazine joins in the there-necked flask that whipping appts and thermometer are housed, add the dihydroxy ethyl secondary amine of 160 grams again, add the water of 20 grams, add the ammonium ferric sulfate catalyst of 0.8 gram, react 5 ~ 7 hours at 140 DEG C ~ 160 DEG C temperature, slowly be cooled to 70 ~ 80 DEG C, continue stirring 1 ~ 2 hour, remove moisture under reduced pressure, obtained three (amino-succinic acid amide group) – s-triazine rust-inhibiting additives.
Embodiment 2
In the there-necked flask that whipping appts and thermometer are housed, add 60mL water, the aspartic acid and the 20 grams of potassium hydroxide that add 78 grams carry out acid-base neutralisation reaction, after solution clarification, produce aspartic acid potassium solution, add 30.2 grams of cyanuric chlorides, add the potassium hydroxide of 36 grams, react 3 ~ 5 hours at 60 DEG C ~ 80 DEG C, generate intermediate compound three (Potassium Aminosuccinate base) – s-triazine, dripping sulfuric acid adjusts pH value to be about 1, at 20 ~ 40 DEG C, carry out acidification reaction 1 ~ 2 hour, filter, get filter cake, obtained three (amino-succinic acid) – s-triazine, by obtained three, (amino-succinic acid) – s-triazine joins in the there-necked flask that whipping appts and thermometer are housed, add the dihydroxy sec.-propyl secondary amine of 155 grams again, add the water of 18 grams, add the ammonium ferric sulfate catalyst of 1.6 grams, react 5 ~ 7 hours at 140 DEG C ~ 160 DEG C temperature, slowly be cooled to 70 ~ 80 DEG C, continue stirring 1 ~ 2 hour, remove moisture under reduced pressure, obtained three (amino-succinic acid amide group) – s-triazine rust-inhibiting additives.
Embodiment 3
In the there-necked flask that whipping appts and thermometer are housed, add 80mL water, the aspartic acid and the 28 grams of potassium hydroxide that add 89 grams carry out acid-base neutralisation reaction, after solution clarification, produce aspartic acid potassium solution, add 30.2 grams of cyanuric chlorides, add the sodium hydroxide of 26 grams, react 3 ~ 5 hours at 60 DEG C ~ 80 DEG C, generate intermediate compound three (amino-succinic acid alkali) – s-triazine, dripping sulfuric acid adjusts pH value to be about 1, at 20 ~ 40 DEG C, carry out acidification reaction 1 ~ 2 hour, filter, get filter cake, obtained three (amino-succinic acid) – s-triazine, by obtained three, (amino-succinic acid) – s-triazine joins in the there-necked flask that whipping appts and thermometer are housed, add the dihydroxy ethyl secondary amine of 70 grams and the dihydroxy sec.-propyl secondary amine of 88 grams again, add the water of 25 grams, add the ammonium ferric sulfate catalyst of 2.4 grams, react 5 ~ 7 hours at 140 DEG C ~ 160 DEG C temperature, slowly be cooled to 70 ~ 80 DEG C, continue stirring 1 ~ 2 hour, remove moisture under reduced pressure, obtained three (amino-succinic acid amide group) – s-triazine rust-inhibiting additives.
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. one kind three (amino-succinic acid amide group) – s-triazine and preparation method thereof, it is characterized in that: aspartic acid and alkali-metal oxyhydroxide carry out acid-base neutralisation reaction, produce aspartate, aspartate and cyanuric chloride, under alkali-metal hydroxide-catalyzed effect, its reaction generate three (amino-succinic acid alkali) – s-triazine is after acidifying, react under catalyst action with hydroxy-alkyl secondary again, generate three (amino-succinic acid amide group) – s-triazine rust-inhibiting additive, specifically comprises following steps:
1). take water as solvent, aspartic acid and alkali-metal oxyhydroxide carry out acid-base neutralisation reaction, produce aspartic acid salts solution;
2). cyanuric chloride and aspartic acid salts solution, under alkali-metal hydroxide-catalyzed effect, react 3 ~ 5 hours at 60 DEG C ~ 80 DEG C, generate intermediate compound three (amino-succinic acid alkali) – s-triazine;
3). three (amino-succinic acid alkali) – s-triazine in acid condition, at 20 ~ 40 DEG C, carries out acidification reaction 1 ~ 2 hour, filters, gets filter cake, obtained three (amino-succinic acid) – s-triazine;
4). three (amino-succinic acid) – s-triazine and hydroxy-alkyl secondary, a small amount of water is solvent, under ammonium ferric sulfate catalyst effect, react 5 ~ 7 hours at 140 DEG C ~ 160 DEG C temperature, slowly be cooled to 70 ~ 80 DEG C, continue stirring 1 ~ 2 hour, remove moisture under reduced pressure, obtained three (amino-succinic acid amide group) – s-triazine rust-inhibiting additives.
2. according to claim 1 a kind of three (amino-succinic acid amide group) – s-triazine and preparation method thereof, is characterized in that: the mol ratio of described described cyanuric chloride, aspartic acid, alkali-metal oxyhydroxide and hydroxy-alkyl secondary is 1 ﹕ 3 ~ 4 ﹕ 5 ~ 7 ﹕ 6 ~ 8; Described ammonium ferric sulfate catalyst, its consumption is 0.5% ~ 1.5% of hydroxy-alkyl secondary consumption.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0733766A (en) * | 1993-07-23 | 1995-02-03 | Shikoku Chem Corp | Diamino-s-triazine compound having imidazole ring and method for preventing copper from rusting using the same compound |
| JP2006241120A (en) * | 2005-03-07 | 2006-09-14 | Nippon Steel Chem Co Ltd | Triazine derivative and method for producing the same and metal surface treatment agent |
| CN102250029A (en) * | 2011-05-16 | 2011-11-23 | 修建东 | Preparation method of triazine hydroxyethyl ethylenediamine polycarboxylic acid |
| CN102250027A (en) * | 2011-05-16 | 2011-11-23 | 修建东 | Preparation method of 2,4,6-tri(caproyl aminomethyl sulfo)-s-triazine |
| CN102633737A (en) * | 2012-04-14 | 2012-08-15 | 修建东 | Synthesis of triazine amide organic acid |
| CN102643243A (en) * | 2012-04-14 | 2012-08-22 | 修建东 | Synthesis of triazine adipic acid diamide |
-
2013
- 2013-11-25 CN CN201310598146.6A patent/CN104649989A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0733766A (en) * | 1993-07-23 | 1995-02-03 | Shikoku Chem Corp | Diamino-s-triazine compound having imidazole ring and method for preventing copper from rusting using the same compound |
| JP2006241120A (en) * | 2005-03-07 | 2006-09-14 | Nippon Steel Chem Co Ltd | Triazine derivative and method for producing the same and metal surface treatment agent |
| CN102250029A (en) * | 2011-05-16 | 2011-11-23 | 修建东 | Preparation method of triazine hydroxyethyl ethylenediamine polycarboxylic acid |
| CN102250027A (en) * | 2011-05-16 | 2011-11-23 | 修建东 | Preparation method of 2,4,6-tri(caproyl aminomethyl sulfo)-s-triazine |
| CN102633737A (en) * | 2012-04-14 | 2012-08-15 | 修建东 | Synthesis of triazine amide organic acid |
| CN102643243A (en) * | 2012-04-14 | 2012-08-22 | 修建东 | Synthesis of triazine adipic acid diamide |
Non-Patent Citations (3)
| Title |
|---|
| WEERANUCH KARUEHANON,ET AL: "Microwave-assisted SNAr reaction of 2,4,6-trichloro-1,3,5-triazine for the rapid synthesis of C3-symmetrical polycarboxylate ligands", 《 TETRAHEDRON LETTERS》 * |
| 汪权 等: "2，4，6-三氨基酸取代-1，3，5-均三嗪衍生物的合成研究", 《化学试剂》 * |
| 薛守庆 等: "基于噻二唑型水基润滑油防锈剂的合成，表征和应用", 《渤海大学学报（自然科学版）》 * |
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