CN104649915A - Polyhydroxyl undecanedioic acid ester amino compound and preparation method thereof - Google Patents
Polyhydroxyl undecanedioic acid ester amino compound and preparation method thereof Download PDFInfo
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- CN104649915A CN104649915A CN201310602794.4A CN201310602794A CN104649915A CN 104649915 A CN104649915 A CN 104649915A CN 201310602794 A CN201310602794 A CN 201310602794A CN 104649915 A CN104649915 A CN 104649915A
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Abstract
The invention discloses a polyhydroxyl undecanedioic acid ester amino compound and a preparation method thereof. The preparation method is characterized by comprising the following steps: by taking a small amount of water as a solvent, performing neutralization reaction on undecanedioic acid and trihydroxyalkyl tertiary amine so as to prepare a solution of an undecanedioic acid trihydroxyalkyl tertiary ammonium salt; under the action of a catalyst, by taking methylbenzene as a water-carrying agent, performing refuxing esterification reaction, and distilling to remove methylbenzene, thereby preparing the polyhydroxyl undecanedioic acid ester amino compound. The synthesized compound is an organic polyhydroxyl undecanedioic acid ester amino compound which has the characteristic that two carbonyl groups and amino groups are bonded with metals, so that an anti-rusting function can be achieved; with multiple hydroxyalkyl groups, the compound is good in water solubility; the compound is a diester with certain lubricating property.
Description
Technical field
The present invention relates to rust-inhibiting additive synthesis technical field, espespecially a kind of poly-hydroxy undecane diacid ester amine compound 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 poly-hydroxy undecane diacid ester amine compound and preparation method thereof.
To achieve these goals, technical solution of the present invention is: with a small amount of water for solvent, undecane diprotic acid and three tertiary amines carry out neutralization reaction, producing the aqueous solution of undecane diprotic acid three tertiary amines salt, under catalyst action, then is water entrainer with toluene, carry out refuxing esterification reaction, distillation removing toluene, obtained poly-hydroxy undecane diacid ester amine compound, specifically comprises following steps:
1). with a small amount of water for solvent, undecane diprotic acid (I) and three tertiary amines (II), stirring reaction 1 ~ 2 hour at 50 DEG C ~ 70 DEG C, produce the aqueous solution of undecane diacid three tertiary amines salt (III), its main chemical reactions is:
2). take toluene as water entrainer, under catalyst action, the aqueous solution of undecane diacid three tertiary amines salt (III) is at 140 DEG C ~ 170 DEG C, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, reacted after 4 ~ 6 hours, distillation removing toluene, obtained poly-hydroxy undecane diacid ester amine compound (IV), its main chemical reactions is:
In formula, R
1, R
2and R
3it is the one in the lower alkylene such as ethylidene independent of each other, propylidene, isopropylidene, butylidene or isobutylidene.
Further, described undecane diprotic acid and the mol ratio of three tertiary amines are 1 ﹕ 2 ~ 3.
Described catalyzer is the metal ammonium salt of sulfuric acid or the metal-salt of thionamic acid, and its consumption is 0.5% ~ 2% of three tertiary amines consumptions.
A kind of poly-hydroxy undecane diacid of the present invention ester amine compound and preparation method thereof, its feature and advantage are: raw material undecane diprotic acid is through biological fermentation, and source is sufficient, environmental protection, and cost is lower; Synthetics is a kind of organic polyhydroxy undecane diacid ester amine compound, has two carbonyls and characteristic that is amino and melts combine, can play rust inhibition; There is multiple hydroxyalkyl, good water solubility; Synthetics is a kind of dibasic acid esters, has certain oilness; Operation is simple, is applicable to suitability for industrialized production.
Embodiment
Embodiment 1
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add 15 grams of water, add 69 grams of trihydroxyethyl tertiary amines, add 50 grams of undecane diacids in batches, at 50 DEG C ~ 70 DEG C, stirring reaction is after 1 ~ 2 hour, produce the aqueous solution of undecane diacid trihydroxyethyl tertiary ammonium salt, add 100mL methylbenzene water-taking agent again, add the amino sodium sulfonate of 1.3 grams of catalyzer, under being heated to 150 DEG C ~ 170 DEG C temperature, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, react after 4 ~ 6 hours, distillation removing toluene, obtained poly-hydroxy undecane diacid ester amine compound.
Embodiment 2
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add 15 grams of water, add 32 gram of three hydroxyl sec.-propyl tertiary amine, add 55 grams of undecane diacids in batches, at 50 DEG C ~ 60 DEG C, stirring reaction is after 1 ~ 2 hour, produce the aqueous solution of undecane diacid three hydroxyl sec.-propyl tertiary ammonium salt, add 120mL methylbenzene water-taking agent again, add 1 gram of catalyst sulfuric acid iron ammonium, under being heated to 140 DEG C ~ 160 DEG C temperature, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, react after 4 ~ 6 hours, distillation removing toluene, obtained poly-hydroxy undecane diacid ester amine compound.
Embodiment 3
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add 20 grams of water, add 82 grams of trihydroxyethyl tertiary amines and 53 gram of three hydroxyl sec.-propyl tertiary amine, add 60 grams of undecane diacids in batches, at 60 DEG C ~ 70 DEG C, stirring reaction is after 1 ~ 2 hour, produce the aqueous solution of undecane diacid three tertiary amines salt, add 150mL methylbenzene water-taking agent again, add 0.7 gram of catalyst sulfuric acid ammonium, under being heated to 140 DEG C ~ 170 DEG C temperature, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, react after 4 ~ 6 hours, distillation removing toluene, obtained poly-hydroxy undecane diacid ester amine compound.
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. poly-hydroxy undecane diacid ester amine compound and preparation method thereof, it is characterized in that: with a small amount of water for solvent, undecane diprotic acid and three tertiary amines carry out neutralization reaction, producing the aqueous solution of undecane diprotic acid three tertiary amines salt, under catalyst action, then is water entrainer with toluene, carry out refuxing esterification reaction, distillation removing toluene, obtained poly-hydroxy undecane diacid ester amine compound, specifically comprises following steps:
1). with a small amount of water for solvent, undecane diprotic acid and three tertiary amines, stirring reaction 1 ~ 2 hour at 50 DEG C ~ 70 DEG C, produces the aqueous solution of undecane diacid three tertiary amines salt;
2). take toluene as water entrainer, under catalyst action, the aqueous solution of undecane diacid three tertiary amines salt is at 140 DEG C ~ 170 DEG C, carry out refuxing esterification reaction, the water that water-and-oil separator separating reaction generates, react after 4 ~ 6 hours, distillation removing toluene, obtained poly-hydroxy undecane diacid ester amine compound.
2. a kind of poly-hydroxy undecane diacid ester amine compound according to claim 1 and preparation method thereof, is characterized in that: described undecane diprotic acid and the mol ratio of three tertiary amines are 1 ﹕ 2 ~ 3; Described catalyzer is the metal ammonium salt of sulfuric acid or the metal-salt of thionamic acid, and its consumption is 0.5% ~ 2% of three tertiary amines consumptions.
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| CN201310602794.4A CN104649915A (en) | 2013-11-26 | 2013-11-26 | Polyhydroxyl undecanedioic acid ester amino compound and preparation method thereof |
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| CN201310602794.4A CN104649915A (en) | 2013-11-26 | 2013-11-26 | Polyhydroxyl undecanedioic acid ester amino compound and preparation method thereof |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1030750A (en) * | 1987-06-19 | 1989-02-01 | 阿托化学公司 | Multi-fluoro amino-alchol and ester class thereof, their preparation method and as the application of lubricant additive |
| EP0664331A1 (en) * | 1994-01-20 | 1995-07-26 | Shell Internationale Researchmaatschappij B.V. | Substituted polyoxyalkylene compounds |
| CN1127292A (en) * | 1995-01-16 | 1996-07-24 | 中国石油化工总公司 | Ashless stain-resistant additive of lubricating oil |
| CN102002415A (en) * | 2009-09-02 | 2011-04-06 | 中国石油天然气股份有限公司 | Ash-free antirust additive for industrial lubricant and preparation method thereof |
-
2013
- 2013-11-26 CN CN201310602794.4A patent/CN104649915A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1030750A (en) * | 1987-06-19 | 1989-02-01 | 阿托化学公司 | Multi-fluoro amino-alchol and ester class thereof, their preparation method and as the application of lubricant additive |
| EP0664331A1 (en) * | 1994-01-20 | 1995-07-26 | Shell Internationale Researchmaatschappij B.V. | Substituted polyoxyalkylene compounds |
| CN1127292A (en) * | 1995-01-16 | 1996-07-24 | 中国石油化工总公司 | Ashless stain-resistant additive of lubricating oil |
| CN102002415A (en) * | 2009-09-02 | 2011-04-06 | 中国石油天然气股份有限公司 | Ash-free antirust additive for industrial lubricant and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| 刘毅飞 等: "固体超强酸催化合成季戊四醇油酸酯及其防锈性能研究", 《润滑油》 * |
| 李久盛 等: "一种酯类防锈剂的性能及应用", 《润滑油与燃料》 * |
| 李志林 等: "水基防锈剂的研究进展", 《表面技术》 * |
| 王亚杰 等: "三乙醇胺硼酸酯的合成及其防锈性能", 《材料保护》 * |
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Application publication date: 20150527 |
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