CN104030933A - Method for synthesizing beta-isoalkanol amino valeric acid cyclohexylamine - Google Patents
Method for synthesizing beta-isoalkanol amino valeric acid cyclohexylamine Download PDFInfo
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- CN104030933A CN104030933A CN201410205315.XA CN201410205315A CN104030933A CN 104030933 A CN104030933 A CN 104030933A CN 201410205315 A CN201410205315 A CN 201410205315A CN 104030933 A CN104030933 A CN 104030933A
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- alcohol base
- silane alcohol
- different silane
- aminovaleric acid
- valerolactim
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- LBOGZEQDXVHCJL-UHFFFAOYSA-N NC1=CCCCCC1 Chemical compound NC1=CCCCCC1 LBOGZEQDXVHCJL-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses a method for synthesizing beta-isoalkanol amino valeric acid cyclohexylamine. The method comprises the steps: with toluene as a solvent and zinc chloride as a catalyst, after a reaction of epoxyalkane and valerolactam is completed under a stirring condition, carrying out reduced pressure distillation to remove the solvent and unreacted materials, and thus obtaining a colorless liquid beta-isoalkanol valerolactam; adding a sodium hydroxide solution, carrying out a hydrolysis reaction, and thus obtaining a beta-isoalkanol amino sodium valerate solution; and then slowly adding an acid solution, adjusting the pH to about 1.0, adding the precipitated beta-isoalkanol amino valeric acid into cyclohexylamine, and thus obtaining beta-isoalkanol amino valeric acid cyclohexylamine, wherein the reaction is easily carried out. The synthetic product has multiple active adsorption centers, can improve the anode polarization performance, and inhibits corrosion; and the synthetic product also has characteristics of binding amino, carboxyl and cyclohexylamine salt with metals, and has a strong rust prevention effect.
Description
Technical field
The present invention relates to volatile rust prevention additive synthesis technical field, the synthetic method of espespecially a kind of β-different silane alcohol base aminovaleric acid hexahydroaniline.
?
Background technology
Corrosion is metallic substance and surrounding environment generation chemistry or electrochemical reaction and destroyed phenomenon is a kind of inverse process of smelting, and physical environment and industrial media can cause the corrosion of metallic substance.Metal and goods thereof are in transportation and storage process, and especially antirust problem is transported, inevitably needed to relate in the wet land route of sea transport and high upsurge.
Vapor phase inhibitor technology is to apply a kind of antirust technology that vapor phase inhibitor is basis, solid-state vapor phase inhibitor has volatility at normal temperatures, can constantly volatilize constantly, be full of whole packaging vessel, volatile rust preventive material is by vapor phase inhibitor performance rust inhibition wherein, vapor phase inhibitor continues at normal temperatures, gasification lentamente, finally can be all the time in " saturated " state in enclosed space, the rust-preventive agent steam evaporating is adsorbed on exposed metallic surface, thereby form the thick stable protective membrane of a Ge Daoliangge branch, this protective membrane can prevent oxygen effectively, the ambiances such as moisture are to corrosion of metal, thereby play outstanding rust inhibition, can reach long-term, stable rust-proof effect.Simultaneously; the steam of this vapor phase inhibitor can also be by reacting, form passive film complex compound, change the acid or alkali environment of metallic surface and forming the form passivating metallic surfaces such as hydrophobic film in metallic surface with metal ion; due to its adhering in metallic surface; play the effect of protection metal, thereby prevent or delay the corrosion of metal.
Although volatile rust prevention erosion technology enters, China's time is short, and tempo is very fast, yet Chinese vapor phase inhibitor technology is compared with advanced country, also exists that range of product is few, the wideless problem of application coverage rate.Therefore, should strengthen Resource by Utilizing Advanced Technologies, strengthen the research and development of vapor phase inhibitor simultaneously.
Summary of the invention
The object of the present invention is to provide the synthetic method of a kind of β-different silane alcohol base aminovaleric acid hexahydroaniline.
Technical solution of the present invention is: take toluene as solvent, zinc chloride is catalyzer, epoxy alkane and Valerolactim are under agitation condition, after having reacted, underpressure distillation is except desolventizing and unreacted reactant, and the colourless liquid β obtaining-different silane alcohol base Valerolactim, adds sodium hydroxide solution wherein, the reaction that is hydrolyzed, obtains β-different silane alcohol base aminovaleric acid sodium solution; Slowly add acid solution again, adjust PH to 1.0 left and right, the β separating out-different silane alcohol base aminovaleric acid joins in hexahydroaniline, makes β-different silane alcohol base aminovaleric acid hexahydroaniline.Specifically comprise following steps:
1). take toluene as solvent, zinc chloride is catalyzer, epoxy alkane (I) and Valerolactim (II) in molar ratio 1 ﹕ 2～3 feed intake, under agitation condition, 70 ℃～80 ℃ back flow reaction 8～10 hours, after having reacted, underpressure distillation is except desolventizing and unreacted reactant, the colourless liquid β obtaining-different silane alcohol base Valerolactim (III).Its main chemical reactions is:
2). to adding the reaction that is hydrolyzed of 20% sodium hydroxide solution in β-different silane alcohol base Valerolactim (III), obtain β-different silane alcohol base aminovaleric acid sodium (IV) solution, its main chemical reactions is:
3). in β-different silane alcohol base aminovaleric acid sodium (IV) solution, slowly add dilute hydrochloric acid solution, adjust PH to 1.0 left and right, separate out solid product, water backwash is washed, and obtains β-different silane alcohol base aminovaleric acid (V), and its main chemical reactions is:
4). β-different silane alcohol base aminovaleric acid (V) is joined in hexahydroaniline (VI), under stirring, heating for dissolving, cooling, make β-different silane alcohol base aminovaleric acid hexahydroaniline (VII), its main chemical reactions is:
Wherein, in reaction formula, R is that hydrogen atom or carbonatoms are 1
~4 alkyl, preferably hydrogen atom and methyl.
Further, described toluene consumption is 2～3 times of Valerolactim consumption
.
Described catalyzer zinc chloride consumption is 4%～8% of epoxy alkane quality
.
Described epoxy alkane
,the mol ratio of Valerolactim and hexahydroaniline is 1 ﹕ 1～1.2 ﹕ 1～1.3.
The synthetic method of a kind of β of the present invention-different silane alcohol base aminovaleric acid hexahydroaniline, its feature and advantage are: adopt epoxy alkane and Valerolactim to react, control the open loop of epoxy alkane by adding catalyzer zinc chloride, reaction is easily carried out; Synthetics has many activated adsorption center, can improve anodic polarization performance, inhibition of corrosion; Synthetics also has the characteristic of amido, carboxyl and cyclohexylamine salt and melts combine, and rust inhibition is strong; 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 120 grams of toluene, add 1.12 grams of zinc chloride and 48 grams of Valerolactims, slowly add 28 grams of epoxy alkane, under agitation condition, 70 ℃～75 ℃ back flow reaction 10 hours, after having reacted, underpressure distillation is except desolventizing and unreacted reactant, the colourless liquid β obtaining-different silane alcohol base Valerolactim, to adding the reaction that is hydrolyzed of 178 grams of 20% sodium hydroxide solutions in β-different silane alcohol base Valerolactim, obtain β-different silane alcohol base aminovaleric acid sodium solution, in β-different silane alcohol base aminovaleric acid sodium solution, slowly add dilute hydrochloric acid solution again, adjust PH to 1.0 left and right, separate out solid product, water backwash is washed, obtain β-different silane alcohol base aminovaleric acid, β-different silane alcohol base aminovaleric acid is joined in 47.8 grams of hexahydroaniline, under stirring, heating for dissolving, cooling, make β-different silane alcohol base aminovaleric acid hexahydroaniline.
Embodiment 2
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add 145 grams of toluene, add 1.32 grams of zinc chloride and 48.4 grams of Valerolactims, slowly add 32 grams of epoxy alkane, under agitation condition, 70 ℃～80 ℃ back flow reaction 8 hours, after having reacted, underpressure distillation is except desolventizing and unreacted reactant, the colourless liquid β obtaining-different silane alcohol base Valerolactim, to adding the reaction that is hydrolyzed of 178 grams of 20% sodium hydroxide solutions in β-different silane alcohol base Valerolactim, obtain β-different silane alcohol base aminovaleric acid sodium solution, in β-different silane alcohol base aminovaleric acid sodium solution, slowly add dilute hydrochloric acid solution again, adjust PH to 1.0 left and right, separate out solid product, water backwash is washed, obtain β-different silane alcohol base aminovaleric acid, β-different silane alcohol base aminovaleric acid is joined in 50.5 grams of hexahydroaniline, under stirring, heating for dissolving, cooling, make β-different silane alcohol base aminovaleric acid hexahydroaniline.
Embodiment 3
Whipping appts is being housed, in the four-hole bottle of reflux condensate device and thermometer, add 123 grams of toluene, add 2.4 grams of zinc chloride and 61.4 grams of Valerolactims, slowly add 30 grams of epoxy alkane, under agitation condition, 75 ℃～80 ℃ back flow reaction 9 hours, after having reacted, underpressure distillation is except desolventizing and unreacted reactant, the colourless liquid β obtaining-different silane alcohol base Valerolactim, to adding the reaction that is hydrolyzed of 178 grams of 20% sodium hydroxide solutions in β-different silane alcohol base Valerolactim, obtain β-different silane alcohol base aminovaleric acid sodium solution, in β-different silane alcohol base aminovaleric acid sodium solution, slowly add dilute hydrochloric acid solution again, adjust PH to 1.0 left and right, separate out solid product, water backwash is washed, obtain β-different silane alcohol base aminovaleric acid, β-different silane alcohol base aminovaleric acid is joined in 66.5 grams of hexahydroaniline, under stirring, heating for dissolving, cooling, make β-different silane alcohol base aminovaleric acid hexahydroaniline.
The above; embodiment is only that the preferred embodiment of the present invention is described; not scope of the present invention is limited; under the prerequisite of spirit that does not depart from the technology of the present invention; various distortion and improvement that this area engineering technical personnel make technical scheme of the present invention, all should fall in the definite protection domain of claims of the present invention.
Claims (2)
1. the synthetic method of β-different silane alcohol base aminovaleric acid hexahydroaniline, it is characterized in that: take toluene as solvent, zinc chloride is catalyzer, epoxy alkane and Valerolactim are under agitation condition, and after having reacted, underpressure distillation is except desolventizing and unreacted reactant, the colourless liquid β obtaining-different silane alcohol base Valerolactim, add wherein sodium hydroxide solution, the reaction that is hydrolyzed, obtains β-different silane alcohol base aminovaleric acid sodium solution; Slowly add acid solution again, adjust PH to 1.0 left and right, the β separating out-different silane alcohol base aminovaleric acid joins in hexahydroaniline, makes β-different silane alcohol base aminovaleric acid hexahydroaniline, specifically comprises following steps:
1). take toluene as solvent, zinc chloride is catalyzer, epoxy alkane and Valerolactim in molar ratio 1 ﹕ 2～3 feed intake, under agitation condition, 70 ℃～80 ℃ back flow reaction 8～10 hours, after having reacted, underpressure distillation is except desolventizing and unreacted reactant, the colourless liquid β obtaining-different silane alcohol base Valerolactim;
2). to adding the reaction that is hydrolyzed of 20% sodium hydroxide solution in β-different silane alcohol base Valerolactim, obtain β-different silane alcohol base aminovaleric acid sodium solution;
3). in β-different silane alcohol base aminovaleric acid sodium solution, slowly add dilute hydrochloric acid solution, adjust PH to 1.0 left and right, separate out solid product, water backwash is washed, and obtains β-different silane alcohol base aminovaleric acid;
4). β-different silane alcohol base aminovaleric acid is joined in hexahydroaniline, under stirring, heating for dissolving, cooling, make β-different silane alcohol base aminovaleric acid hexahydroaniline.
2. the synthetic method of a kind of β according to claim 1-different silane alcohol base aminovaleric acid hexahydroaniline, is characterized in that: described toluene consumption is 2～3 times of Valerolactim consumption
;described catalyzer zinc chloride consumption is 4%～8% of epoxy alkane quality
;described epoxy alkane
,the mol ratio of Valerolactim and hexahydroaniline is 1 ﹕ 1～1.2 ﹕ 1～1.3.
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Citations (7)
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| WO2005018643A1 (en) * | 2003-08-25 | 2005-03-03 | Ranbaxy Laboratories Limited | Metabolites of 1-{3-4`4-(2-methoxyphenyl) piperazin-1-yl!-propyl}-piperidine-2, 6-dione for use in the treatment of benign prostatic hyperplasia |
| CN100390169C (en) * | 2003-03-01 | 2008-05-28 | 阿斯利康(瑞典)有限公司 | Hydroxymethyl substituted dihydroisoxazole derivatives useful as antibiotic agents |
| WO2009059225A2 (en) * | 2007-11-02 | 2009-05-07 | Pain Therapeutics, Inc. | Analgesia with minimal tolerance and dependence by a mu opioid receptor agonist that also binds filamin a |
| CN101717341A (en) * | 2009-08-26 | 2010-06-02 | 凯莱英生命科学技术(天津)有限公司 | Synthesizing method, partial intermediate products and final products of chiral beta-alkamine derivative |
| CN102405218A (en) * | 2009-04-23 | 2012-04-04 | 施万制药 | Diamide compounds having muscarinic receptor antagonist and ss2 adrenergic receptor agonist activity |
| CN103140485A (en) * | 2010-09-30 | 2013-06-05 | 施万制药 | Crystalline oxalate salts of a diamide compound |
| US20140018341A1 (en) * | 2012-07-13 | 2014-01-16 | Hoau-Yan Wang | Method of inhibiting tau phosphorylation |
-
2014
- 2014-05-16 CN CN201410205315.XA patent/CN104030933A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100390169C (en) * | 2003-03-01 | 2008-05-28 | 阿斯利康(瑞典)有限公司 | Hydroxymethyl substituted dihydroisoxazole derivatives useful as antibiotic agents |
| WO2005018643A1 (en) * | 2003-08-25 | 2005-03-03 | Ranbaxy Laboratories Limited | Metabolites of 1-{3-4`4-(2-methoxyphenyl) piperazin-1-yl!-propyl}-piperidine-2, 6-dione for use in the treatment of benign prostatic hyperplasia |
| WO2009059225A2 (en) * | 2007-11-02 | 2009-05-07 | Pain Therapeutics, Inc. | Analgesia with minimal tolerance and dependence by a mu opioid receptor agonist that also binds filamin a |
| CN102405218A (en) * | 2009-04-23 | 2012-04-04 | 施万制药 | Diamide compounds having muscarinic receptor antagonist and ss2 adrenergic receptor agonist activity |
| CN101717341A (en) * | 2009-08-26 | 2010-06-02 | 凯莱英生命科学技术(天津)有限公司 | Synthesizing method, partial intermediate products and final products of chiral beta-alkamine derivative |
| CN103140485A (en) * | 2010-09-30 | 2013-06-05 | 施万制药 | Crystalline oxalate salts of a diamide compound |
| US20140018341A1 (en) * | 2012-07-13 | 2014-01-16 | Hoau-Yan Wang | Method of inhibiting tau phosphorylation |
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