CN103342684A - 2-(2'-hydroxyl-ethoxyl-ethoxyl)-2H-benzotriazole as well as synthesis and corrosion inhibition application thereof - Google Patents
2-(2'-hydroxyl-ethoxyl-ethoxyl)-2H-benzotriazole as well as synthesis and corrosion inhibition application thereof Download PDFInfo
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- CN103342684A CN103342684A CN2013103256335A CN201310325633A CN103342684A CN 103342684 A CN103342684 A CN 103342684A CN 2013103256335 A CN2013103256335 A CN 2013103256335A CN 201310325633 A CN201310325633 A CN 201310325633A CN 103342684 A CN103342684 A CN 103342684A
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- YDTGHXWCYDAQKX-UHFFFAOYSA-N BrCCOc1ccccc1-[n]1nc(cccc2)c2n1 Chemical compound BrCCOc1ccccc1-[n]1nc(cccc2)c2n1 YDTGHXWCYDAQKX-UHFFFAOYSA-N 0.000 description 1
- QQHMTRNYUORQPT-CYVLTUHYSA-N C=C(C=CC=C1)/C1=N\N(c(cccc1)c1OCCOCCO)N Chemical compound C=C(C=CC=C1)/C1=N\N(c(cccc1)c1OCCOCCO)N QQHMTRNYUORQPT-CYVLTUHYSA-N 0.000 description 1
- UWDTUHBPZIVKEB-UHFFFAOYSA-N OCCOCCOc(cccc1)c1-[n]1nc(cccc2)c2n1 Chemical compound OCCOCCOc(cccc1)c1-[n]1nc(cccc2)c2n1 UWDTUHBPZIVKEB-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to 2-(2'-hydroxyl-ethoxyl-ethoxyl)-2H-benzotriazole with the chemical structural formula shown in the specification. The synthetic steps are as follows: 1, synthesis of 2-(2'-bromoethoxyl)-2H-benzotriazole; 2, synthesis of 2-(2'-hydroxyl-ethoxyl-ethoxyl)-2H-benzotriazole. The 2-(2'-hydroxyl-ethoxyl-ethoxyl)-2H-benzotriazole provided by the invention has a corrosion inhibition effect to copper in 3.5% sodium chloride liquor. The number of heteroatoms in the molecular structure is increased to the benefit of improving the corrosion inhibition efficiency. The synthesizing and separating methods are simple, and raw materials are convenient and easy to obtain.
Description
Technical field
The invention belongs to benzotriazole inhibiter and synthesis technical field thereof, particularly contain a plurality of heteroatomic benzotriazole derivative inhibiter and synthetic and inhibition application thereof.
Background technology
Existing benzotriazole analog derivative has certain corrosion inhibition to metallic copper in salt brine solution, but corrosion mitigating effect is undesirable, and there is certain difficulty in modification to benzotriazole.
Summary of the invention
Purpose of the present invention is exactly in order to overcome the deficiency of above-mentioned background technology, to contain a plurality of heteroatomic benzotriazole derivatives and synthesize, as the inhibiter of metallic copper.
2-involved in the present invention (2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole, its chemical structural formula is as follows:
The synthetic method of above-mentioned 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole, step is as follows:
Synthesizing of the first step: 2-(2 '-bromine oxethyl)-2H-benzotriazole
Reaction equation is:
2-(2 '-hydroxyl)-2H-benzotriazole is joined in the Wolff bottle, add 1 of equimolar amount, the 2-ethylene dibromide, with the volume be 30～60 times acetone of glycol dibromide volume as solvent, add salt of wormwood then, its molar weight is 2～4 times of glycol dibromide; Room temperature lower magnetic force stirring reaction 24 hours, the reaction after-filtration is removed solid matter, and removal of solvent under reduced pressure obtains thick product; Be developping agent with the cyclohexane give, use the silica gel chromatography column separating purification, obtaining white solid after the vacuum-drying is 2-(2 '-bromine oxethyl)-2H-benzotriazole;
Second step: 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole synthetic
Reaction equation is:
2-(2 '-bromine oxethyl)-2H-benzotriazole being added in the Wolff bottle, add the ethylene glycol of equimolar amount then, is that 80～100 times acetone of ethylene glycol volume is made solvent with the volume, adds salt of wormwood, and its molar weight is 1～3 times of ethylene glycol; Room temperature lower magnetic force stirring reaction 18 hours obtains thick product after the removal of solvent under reduced pressure of reaction back; As developping agent, use the silica gel chromatography column separating purification with methylene dichloride, obtain 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole after the vacuum-drying.
2-of the present invention (2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole has corrosion inhibition to metallic copper in 3.5% sodium chloride solution; Owing to increased heteroatomic number in the benzotriazole category copper inhibitor compound, improved the inhibition efficiency of inhibiter; Synthetic and the separation method of 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole is simple, and raw material conveniently is easy to get.
Description of drawings
Fig. 1. the 1H nmr spectrum of the 2-in the embodiment of the invention 1 (2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole.
Fig. 2. the surface topography map of uncorroded red copper sample after the polishing in the embodiment of the invention 2.
Fig. 3. the surface topography map that in 3.5% sodium chloride solution, soaks red copper sample after 9 days in the embodiment of the invention 2.
Fig. 4. the surface topography map that in 3.5% sodium chloride solution that is dissolved with 5mg/L2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole, soaks red copper sample after 9 days in the embodiment of the invention 2.
Embodiment
Further specify the present invention below in conjunction with embodiment and accompanying drawing:
Embodiment 1
Synthesizing of 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole
Synthesize and carry out in two steps:
Synthesizing of the first step: 2-(2 '-bromine oxethyl)-2H-benzotriazole
Respectively with 2-(2 '-hydroxyl)-2H-benzotriazole (2.11g, 0.01mol), glycol dibromide (1.82g 0.01mol) joins in the 100ml Wolff bottle, adds 50ml acetone and makes solvent, add salt of wormwood (4.14g, 0.03mol); Room temperature lower magnetic force stirring reaction 24 hours, the reaction after-filtration is removed solid matter, and removal of solvent under reduced pressure obtains thick product; Be developping agent with the cyclohexane give, use the silica gel chromatography column separating purification, obtain 2-(2 '-bromine oxethyl)-2H-benzotriazole of white solid after the vacuum-drying.Fusing point: 102.0～103.0 ° of C, productive rate 68%.
1H-NMR(CDCl
3,500MHz)δ(ppm):3.618-3.702(t,2H,-CH
2-),4.368-4.393(t,2H,-CH
2-),7.066-7.085(d,2H,Ar-H),7.406-7.425(m,2H,Ar-H),7.914-7.933(m,2H,Ar-H),8.279-8.297(d,2H,Ar-H)。
Second step: 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole synthetic
With 2-(2 '-bromine oxethyl)-2H-benzotriazole (3.18g, 0.01mol), ethylene glycol (0.62g 0.01mol) joins in the Wolff bottle of 100ml successively, adds 50ml acetone and makes solvent, add then salt of wormwood (2.76g, 0.02mol); Room temperature lower magnetic force stirring reaction 18 hours, reaction back removal of solvent under reduced pressure; Again with methylene dichloride as developping agent, use the silica gel chromatography column separating purification, obtain product after the vacuum-drying.Fusing point: 107.7～108.1 ° of C, productive rate 45%.Its
1The H nmr spectrum as shown in Figure 1,
1H-NMR (CDCl
3, 500MHz) δ (ppm): 1.783 (s, 1H ,-OH), 3.702-3.720 (t, 2H ,-CH
2-), 3.789-3.807 (t, 2H ,-CH
2-), 3.916-3.934 (t, 2H ,-CH
2-), 4.225-4.243 (t, 2H ,-OCH
2-), 7.076-7.094 (d, 2H, Ar-H), 7.403-7.422 (m, 2H, Ar-H), 7.913-7.933 (m, 2H, Ar-H), 8.267-8.283 (d, 2H, Ar-H).
For the corrosion mitigating effect of The compounds of this invention is described, has prepared the uncorroded red copper sample in polishing back respectively, in 3.5% sodium chloride solution, soaked the red copper sample after 9 days and be dissolved with the red copper sample that soaks in 3.5% sodium chloride solution of 5mg/L2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole after 9 days.
Uncorroded its surface topography of red copper sample in polishing back as shown in Figure 2.Concrete operations: the specification that the red copper sample is processed in advance 20mm * 20mm * 10mm, polish step by step with 280#, 400#, 800#, 1200#, 2000# silicon carbide paper successively then, make the red copper specimen surface smooth smooth, then by distilled water and ethanol ultrasonic cleaning five minutes, oven dry, with its surface topography of TESCAN VEGA III type scanning electron microscopic observation, the acceleration voltage of scanning electron microscope is 20KV, and the scanning multiple is 2000.The surface ratio of red copper sample is more smooth among Fig. 2, and the vestige of sand papering is high-visible.
In 3.5% sodium chloride solution, soak after 9 days its surface topography of red copper sample as shown in Figure 3.Concrete operations: the specification that the red copper sample is processed in advance 20mm * 20mm * 10mm, use 280# then successively, 400#, 800#, 1200#, the 2000# silicon carbide paper is polished step by step, make the red copper specimen surface smooth smooth, then by distilled water and ethanol ultrasonic cleaning five minutes, after the taking-up red copper sample is immersed in 3.5% sodium chloride solution, soak and take out sample after 9 days, dry then with the distilled water flushing specimen surface earlier, with its surface topography of TESCAN VEGA III type scanning electron microscopic observation, the acceleration voltage of scanning electron microscope is 20KV, and the scanning multiple is 2000.The red copper specimen surface can not recognized the vestige of sand papering fully among Fig. 3.
In 3.5% sodium chloride solution that is dissolved with 5mg/L2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole, soak the surface topography of red copper sample after 9 days as shown in Figure 4.Concrete operations: the specification that the red copper sample is processed in advance 20mm * 20mm * 10mm, use 280# then successively, 400#, 800#, 1200#, the 2000# silicon carbide paper is polished step by step, make the red copper specimen surface smooth smooth, then by distilled water and ethanol ultrasonic cleaning five minutes, after the taking-up red copper sample is immersed in the 3.5% sodium-chlor etchant solution that contains 5mg/L2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole, soak and take out sample after 9 days, dry then with the distilled water flushing specimen surface earlier, with its surface topography of TESCAN VEGA III type scanning electron microscopic observation, the acceleration voltage of scanning electron microscope is 20KV, and the scanning multiple is 2000.The red copper specimen surface becomes more coarse and loose among Fig. 4, but the vestige of sand papering also exists.Proved that 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole has good corrosion inhibition to copper.
Claims (3)
1. a 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole, its chemical structural formula is as follows:
2. the synthetic method of 2-as claimed in claim 1 (2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole is characterized in that step is as follows:
Synthesizing of the first step: 2-(2 '-bromine oxethyl)-2H-benzotriazole
Reaction equation is:
Concrete steps:
2-(2 '-hydroxyl)-2H-benzotriazole is joined in the Wolff bottle, add the glycol dibromide of equimolar amount, with the volume be 30～60 times acetone of glycol dibromide volume as solvent, add salt of wormwood then, its molar weight is 2～4 times of glycol dibromide; Room temperature lower magnetic force stirring reaction 24 hours, the reaction after-filtration is removed solid matter, and removal of solvent under reduced pressure obtains thick product; Be developping agent with the cyclohexane give, use the silica gel chromatography column separating purification, obtaining white solid after the vacuum-drying is 2-(2 '-bromine oxethyl)-2H-benzotriazole;
Second step: 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole synthetic
Reaction equation is:
Concrete steps:
2-(2 '-bromine oxethyl)-2H-benzotriazole being added in the Wolff bottle, add the ethylene glycol of equimolar amount then, is that the 80-100 acetone doubly of ethylene glycol volume is made solvent with the volume, adds salt of wormwood, and its molar weight is 1-3 times of ethylene glycol; Room temperature lower magnetic force stirring reaction 18 hours obtains thick product after the removal of solvent under reduced pressure of reaction back; As developping agent, use the silica gel chromatography column separating purification with methylene dichloride, obtain 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole after the vacuum-drying.
3. the purposes of claims 1 described 2-(2 '-hydroxyl-oxyethyl group-oxyethyl group)-2H-benzotriazole is the inhibiter as copper.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106146420A (en) * | 2016-08-11 | 2016-11-23 | 重庆大学 | The synthesis of the water miscible potassium salt derivant containing two or three BTA rings of one class and application |
| CN106279050A (en) * | 2016-08-11 | 2017-01-04 | 重庆大学 | The synthesis of organic sulfonic acid salt derivative and the application of one class water solublity containing double benzene triazole chalcone dyad |
| CN115291483A (en) * | 2022-09-02 | 2022-11-04 | 昆山晶科微电子材料有限公司 | Semiconductor stripping liquid and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0376752A (en) * | 1989-08-17 | 1991-04-02 | Toray Ind Inc | Polyamide resin composition |
| TW200634138A (en) * | 2005-03-23 | 2006-10-01 | Dupont Air Products Nano Materials Llc | Low-dishing composition and method for chemical-mechanical planarization with branched-alkylphenol-substituted benzotriazole |
| CN101885924A (en) * | 2010-06-21 | 2010-11-17 | 重庆大学 | Benzotriazole dye as well as synthesis and application thereof |
-
2013
- 2013-07-30 CN CN2013103256335A patent/CN103342684A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0376752A (en) * | 1989-08-17 | 1991-04-02 | Toray Ind Inc | Polyamide resin composition |
| TW200634138A (en) * | 2005-03-23 | 2006-10-01 | Dupont Air Products Nano Materials Llc | Low-dishing composition and method for chemical-mechanical planarization with branched-alkylphenol-substituted benzotriazole |
| CN101885924A (en) * | 2010-06-21 | 2010-11-17 | 重庆大学 | Benzotriazole dye as well as synthesis and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| D. FROMAGEOT等: "Photodecarboxylation of 2-(2"-carboxymethoxy-5"-methylphenyl)benzotriazole", 《JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY, A》, vol. 44, no. 1, 31 July 1988 (1988-07-31), pages 93 - 98 * |
| 徐群杰等: "苯并三氮唑及其衍生物在硫酸溶液中对铜的缓蚀作用", 《中国腐蚀与防护学报》, vol. 21, no. 3, 30 June 2001 (2001-06-30), pages 172 - 176 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106146420A (en) * | 2016-08-11 | 2016-11-23 | 重庆大学 | The synthesis of the water miscible potassium salt derivant containing two or three BTA rings of one class and application |
| CN106279050A (en) * | 2016-08-11 | 2017-01-04 | 重庆大学 | The synthesis of organic sulfonic acid salt derivative and the application of one class water solublity containing double benzene triazole chalcone dyad |
| CN115291483A (en) * | 2022-09-02 | 2022-11-04 | 昆山晶科微电子材料有限公司 | Semiconductor stripping liquid and preparation method thereof |
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Application publication date: 20131009 |