CN105566390A - Water-soluble 2,5-dimercapto thiadiazole phosphate organic corrosion inhibitor - Google Patents
Water-soluble 2,5-dimercapto thiadiazole phosphate organic corrosion inhibitor Download PDFInfo
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- CN105566390A CN105566390A CN201410518845.XA CN201410518845A CN105566390A CN 105566390 A CN105566390 A CN 105566390A CN 201410518845 A CN201410518845 A CN 201410518845A CN 105566390 A CN105566390 A CN 105566390A
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- dimercaptothiodiazole
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Abstract
The present invention discloses a water-soluble 2,5-dimercapto thiadiazole phosphate organic corrosion inhibitor. According to the present invention, a sulfuric acid solution is adopted as a solvent, 2,5-dimercapto thiadiazole and alpha-alkenyl acid are subjected to a reaction, the compound generated from the reaction is subjected to suction filtration, the filter cake is dissolved with a potassium hydroxide aqueous solution, suction filtration is performed again, filtrate acidification is performed, other purification methods are performed, the obtained material reacts with hydroxyalkyl secondary amine, the filtrate cake is subjected to alkali dissolving, filtrate acidification is performed, other purification methods are performed, the obtained material reacts with hydroxyalkyl secondary amine, and the diamidation product generated from the reaction and phosphorus pentoxide are further subjected to an esterification reaction; the synthesized product has good water solubility; the water-soluble 2,5-dimercapto thiadiazole phosphate organic corrosion inhibitor is an organic heterocyclic dicarboxylic acid amide phosphate, has the multiple slow-release group and metal combining characteristic, and further has characteristics of excellent rust resistance, hard water resistance and extreme pressure property; and the yield is high, the process is simple, and the production is easy.
Description
Technical field
The present invention relates to organic inhibitor synthesis technical field, espespecially a kind of water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors.
Background technology
Inhibiter is a kind of important additive in intermetallic composite coating, in the process of metal working such as metal cutting, grinding, calendering, punching press and tapping, adding of inhibiter not only can make workpiece not corrode at inter process, and the equipment such as lathe, cutter that simultaneously workpiece can be made again to contact with it in the course of processing does not produce corrosion.Along with the development and application of organic rust preventing additive; inorganic salts rust-inhibiting additive is substituted gradually; 2; 5-dimercaptothiodiazole is a kind of five-membered heterocycles, by functional group and reaction, and synthesis 2; the phosphate derivative of 5-dimercaptothiodiazole; add water-soluble, and by physical adsorption be chemisorbed on metallic surface and form the protective membrane aligned, thus more effectively slow down and inhibit corrosion of metal.
Summary of the invention
The object of the present invention is to provide a kind of water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors and preparation method thereof.
Technical solution of the present invention is: to achieve these goals, technical solution of the present invention is: take sulphuric acid soln as solvent, 2, 5-dimercaptothiodiazole and α-thiazolinyl acid are reacted, the compound that its reaction generates is through suction filtration, filter cake potassium hydroxide aqueous solution dissolves, suction filtration again, after acidification of filtrate etc. are purified, react with hydroxy-alkyl secondary again, filter cake alkali dissolution, after acidification of filtrate etc. are purified, react with hydroxy-alkyl secondary again, the diamide product that its reaction generates, esterification is carried out further again with Vanadium Pentoxide in FLAKES, specifically comprise following steps:
1). take sulphuric acid soln as solvent, 2,5-dimercaptothiodiazole (I) is dissolved in sulphuric acid soln, at 45 DEG C ~ 55 DEG C, add α-thiazolinyl acid (II) in batches, react 3 ~ 4 hours, be cooled to less than 30 DEG C, generate intermediate compound (III), its main chemical reactions is:
2). the above-mentioned reaction mass of thin up, suction filtration, the filter cake potassium hydroxide aqueous solution of 5% ~ 10% dissolves, suction filtration removing insolubles again, it is 1 ~ 2 that filtrate acid solution is acidified to PH, and object is separated out again, suction filtration, washing, obtain the intermediate compound (III) of purification;
3). take toluene as solvent, the intermediate compound (III) of purifying and hydroxy-alkyl secondary (VI) react, at 110 ~ 130 DEG C, carry out back flow reaction 3 ~ 5 hours, reaction mixture is lowered the temperature, distillation removing toluene, obtained 2,5-dimercaptothiodiazole diamide derivatives (V), its main chemical reactions is:
4) .2; 5-dimercaptothiodiazole diamide derivatives (V) and the Vanadium Pentoxide in FLAKES be dissolved in sherwood oil react; under 70 ~ 80 DEG C and nitrogen protection; carry out back flow reaction 3 ~ 4 hours, after completion of the reaction, reaction mixture is lowered the temperature; distillation removing sherwood oil; obtained water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors (VI), its main chemical reactions is:
In formula, R
1and R
2separate hydrogen atom, methyl, ethyl, propyl group, sec.-propyl, butyl or isobutyl-, R
3and R
4separate ethylidene, propylidene, isopropylidene or butylidene.
Further, the mol ratio of 2,5-described dimercaptothiodiazoles, α-thiazolinyl acid, hydroxy-alkyl secondary and Vanadium Pentoxide in FLAKES is 1 ﹕ 2 ~ 2.3 ﹕ 2 ~ 2.7 ﹕ 2 ~ 2.5.
Described acid solution is dilution heat of sulfuric acid or dilute hydrochloric acid solution.
A kind of water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors of the present invention, its feature and advantage are: synthetics good water solubility; Be a kind of phosphoric acid ester of organic heterocyclic di-carboxylic acid acid amides, there is the characteristic of multiple eluting group and melts combine, excellent rust inhibition can be played; Synthetics has resistance to hard water and extreme pressure property; Productive rate is high, and technique is simple, easy to make.
Embodiment
Embodiment 1
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the sulfuric acid of 160 gram 70%, add 38 grams 2, 5-dimercaptothiodiazole, it is made to dissolve in sulphuric acid soln, add 57.8 grams of strawberriffs on a small quantity in batches, at 45 DEG C ~ 55 DEG C, react 3 ~ 4 hours, be cooled to less than 30 DEG C, generate intermediate compound, the above-mentioned reaction mass of thin up, suction filtration, the filter cake potassium hydroxide aqueous solution of 10% dissolves, suction filtration removing insolubles again, it is 1 ~ 2 that filtrate dilute hydrochloric acid solution is acidified to PH, object is separated out again, suction filtration, washing, the intermediate compound that must purify, the intermediate compound of purifying loads in four-hole bottle, add 150 grams of toluene solvants, 79 grams of diisopropanolamine (DIPA), at 100 ~ 110 DEG C, carry out back flow reaction 3 ~ 4 hours, reaction mixture is lowered the temperature, distillation removing toluene, obtained 2, 5-dimercaptothiodiazole diamide derivatives, 200 grams of sherwood oils and 89.9 grams of Vanadium Pentoxide in FLAKESs are added in four-hole bottle, dissolve, under 70 ~ 80 DEG C and nitrogen protection, carry out back flow reaction 3 ~ 4 hours, after completion of the reaction, reaction mixture is lowered the temperature, distillation removing sherwood oil, obtained water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors.
Embodiment 2
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the sulfuric acid of 125 gram 70%, add 34 grams 2, 5-dimercaptothiodiazole, it is made to dissolve in sulphuric acid soln, add 42 grams of β-crotonic acids on a small quantity in batches, at 45 DEG C ~ 55 DEG C, react 3 ~ 4 hours, be cooled to less than 30 DEG C, generate intermediate compound, the above-mentioned reaction mass of thin up, suction filtration, the filter cake potassium hydroxide aqueous solution of 6% dissolves, suction filtration removing insolubles again, it is 1 ~ 2 that filtrate dilute hydrochloric acid solution is acidified to PH, object is separated out again, suction filtration, washing, the intermediate compound that must purify, the intermediate compound of purifying loads in four-hole bottle, add 130 grams of toluene solvants and 47.8 grams of diethanolamine, at 100 ~ 110 DEG C, carry out back flow reaction 3 ~ 4 hours, reaction mixture is lowered the temperature, distillation removing toluene, obtained 2, 5-dimercaptothiodiazole diamide derivatives, 180 grams of sherwood oils and 72.4 grams of Vanadium Pentoxide in FLAKESs are added in four-hole bottle, dissolve, under 70 ~ 80 DEG C and nitrogen protection, carry out back flow reaction 3 ~ 4 hours, after completion of the reaction, reaction mixture is lowered the temperature, distillation removing sherwood oil, obtained water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors.
Embodiment 3
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add the sulfuric acid of 150 gram 70%, add 30 grams 2, 5-dimercaptothiodiazole, it is made to dissolve in sulphuric acid soln, add 46.9 grams of α-pentenoic acids on a small quantity in batches, at 45 DEG C ~ 55 DEG C, react 3 ~ 4 hours, be cooled to less than 30 DEG C, generate intermediate compound, the above-mentioned reaction mass of thin up, suction filtration, the filter cake potassium hydroxide aqueous solution of 5% dissolves, suction filtration removing insolubles again, it is 1 ~ 2 that filtrate dilution heat of sulfuric acid is acidified to PH, object is separated out again, suction filtration, washing, the intermediate compound that must purify, the intermediate compound of purifying loads in four-hole bottle, add 130 grams of toluene solvants, 28 grams of diethanolamine, 36 grams of diisopropanolamine (DIPA), at 100 ~ 110 DEG C, carry out back flow reaction 3 ~ 4 hours, reaction mixture is lowered the temperature, distillation removing toluene, obtained 2, 5-dimercaptothiodiazole diamide derivatives, 100 grams of sherwood oils and 57 grams of Vanadium Pentoxide in FLAKESs are added in four-hole bottle, dissolve, under 70 ~ 80 DEG C and nitrogen protection, carry out back flow reaction 3 ~ 4 hours, after completion of the reaction, reaction mixture is lowered the temperature, distillation removing sherwood oil, obtained water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors.
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 (3)
1. water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors, is characterized in that: described water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors are the compounds with following structure:
In formula, R
1and R
2separate hydrogen atom, methyl, ethyl, propyl group, sec.-propyl, butyl or isobutyl-, R
3and R
4separate ethylidene, propylidene, isopropylidene or butylidene.
2. one according to claim 1 water-soluble 2, 5-dimercaptothiodiazole phosphoric acid ester organic inhibitor, it is characterized in that: described water-soluble 2, the preparation method of 5-dimercaptothiodiazole phosphoric acid ester organic inhibitor is: take sulphuric acid soln as solvent, 2, 5-dimercaptothiodiazole and α-thiazolinyl acid are reacted, the compound that its reaction generates is through suction filtration, filter cake potassium hydroxide aqueous solution dissolves, suction filtration again, after acidification of filtrate etc. are purified, react with hydroxy-alkyl secondary again, filter cake alkali dissolution, after acidification of filtrate etc. are purified, react with hydroxy-alkyl secondary again, the diamide product that its reaction generates, esterification is carried out further again with Vanadium Pentoxide in FLAKES, specifically comprise following steps:
1). take sulphuric acid soln as solvent, 2,5-dimercaptothiodiazole is dissolved in sulphuric acid soln, at 45 DEG C ~ 55 DEG C, adds α-thiazolinyl acid in batches, reacts 3 ~ 4 hours, be cooled to less than 30 DEG C, generate intermediate compound;
2). the above-mentioned reaction mass of thin up, suction filtration, the filter cake potassium hydroxide aqueous solution of 5% ~ 10% dissolves, again suction filtration removing insolubles, and it is 1 ~ 2 that filtrate acid solution is acidified to PH, and object is separated out again, suction filtration, washing, obtains the intermediate compound of purification;
3). take toluene as solvent, the intermediate compound of purification and hydroxy-alkyl secondary react, and at 110 ~ 130 DEG C, carry out back flow reaction 3 ~ 5 hours, are lowered the temperature by reaction mixture, distillation removing toluene, obtained 2,5-dimercaptothiodiazole diamide derivatives;
4) .2; 5-dimercaptothiodiazole diamide derivatives and the Vanadium Pentoxide in FLAKES be dissolved in sherwood oil react; under 70 ~ 80 DEG C and nitrogen protection; carry out back flow reaction 3 ~ 4 hours; after completion of the reaction, reaction mixture is lowered the temperature, distillation removing sherwood oil; obtained water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitors.
3. one according to claim 1 water-soluble 2,5-dimercaptothiodiazole phosphoric acid ester organic inhibitor, it is characterized in that: the mol ratio of 2,5-described dimercaptothiodiazoles, α-thiazolinyl acid, hydroxy-alkyl secondary and Vanadium Pentoxide in FLAKES is 1 ﹕ 2 ~ 2.3 ﹕ 2 ~ 2.7 ﹕ 2 ~ 2.5; Described acid solution is dilution heat of sulfuric acid or dilute hydrochloric acid solution.
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| CN201410518845.XA CN105566390A (en) | 2014-10-05 | 2014-10-05 | Water-soluble 2,5-dimercapto thiadiazole phosphate organic corrosion inhibitor |
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| CN201410518845.XA CN105566390A (en) | 2014-10-05 | 2014-10-05 | Water-soluble 2,5-dimercapto thiadiazole phosphate organic corrosion inhibitor |
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| CN201410518845.XA Pending CN105566390A (en) | 2014-10-05 | 2014-10-05 | Water-soluble 2,5-dimercapto thiadiazole phosphate organic corrosion inhibitor |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107747085A (en) * | 2017-10-20 | 2018-03-02 | 鞍钢未来钢铁研究院有限公司 | A kind of hot rolling and cold-rolled steel sheet water-based antirust and preparation method thereof |
| CN114106916A (en) * | 2021-11-19 | 2022-03-01 | 珠海格力电器股份有限公司 | Refrigerating machine oil composition, refrigerant and refrigerating machine oil composition and air conditioning system |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107168A (en) * | 1975-07-24 | 1978-08-15 | Mobil Oil Corporation | Phosphorus substituted dimercapto thiadiazoles |
-
2014
- 2014-10-05 CN CN201410518845.XA patent/CN105566390A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107168A (en) * | 1975-07-24 | 1978-08-15 | Mobil Oil Corporation | Phosphorus substituted dimercapto thiadiazoles |
Non-Patent Citations (2)
| Title |
|---|
| 胡海蓉等: ""含噻二唑膦酸的合成及对铜缓蚀性能研究"", 《化学试剂》 * |
| 薛守庆: ""环保型磷酸酯型水基防锈剂的研制"", 《科学技术与工程》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107747085A (en) * | 2017-10-20 | 2018-03-02 | 鞍钢未来钢铁研究院有限公司 | A kind of hot rolling and cold-rolled steel sheet water-based antirust and preparation method thereof |
| CN107747085B (en) * | 2017-10-20 | 2019-11-01 | 鞍钢未来钢铁研究院有限公司 | A kind of hot rolling and cold-rolled steel sheet water-based antirust and preparation method thereof |
| CN114106916A (en) * | 2021-11-19 | 2022-03-01 | 珠海格力电器股份有限公司 | Refrigerating machine oil composition, refrigerant and refrigerating machine oil composition and air conditioning system |
| CN114106916B (en) * | 2021-11-19 | 2023-01-06 | 珠海格力电器股份有限公司 | Refrigerating machine oil composition, refrigerant and refrigerating machine oil composition and air conditioning system |
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Application publication date: 20160511 |