CN107445901A - The purification process of 2- substituent benzimidazoles - Google Patents
The purification process of 2- substituent benzimidazoles Download PDFInfo
- Publication number
- CN107445901A CN107445901A CN201610380831.5A CN201610380831A CN107445901A CN 107445901 A CN107445901 A CN 107445901A CN 201610380831 A CN201610380831 A CN 201610380831A CN 107445901 A CN107445901 A CN 107445901A
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- substituent
- benzimidazole
- minutes
- activated carbon
- purification process
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Abstract
The present invention relates to the purification process of 2 substituent benzimidazoles, for printed wiring board copper face antioxidant OSP.It discloses 2 substituent benzimidazole crude products, in 1000ml conical flasks, dissolved by heating with 300ml 95% ethanol, maintain the temperature at 65 70 DEG C, with 40 watts of ultra violet lamps 10 120 minutes, solution is by there is miscellaneous purple to gradate to be faint yellow in bottle, solution adds 1 10 grams of activated carbon, flow back 10 60 minutes, it is filtered to remove activated carbon, 200ml is added in system to 250ml water, let cool after boiling, 18 DEG C of bad border left overnights, filter, crystal is washed with a small amount of 50% frozen ethanol, it is dried to obtain pure white flat crystal, yield 78% 81.3%, HPLC examines its content up to 98.6% 99.2%.After 2 substituent benzimidazole products are dissolved with organic solvent, ultraviolet light, the color of system can decorporate the present invention, can obtain pure white by conventional recrystallization processing, a step, purity reaches more than 98% product.
Description
Technical field
The present invention relates to the OSP fields of printed wiring board copper face antioxidant.
Background technology
2- substituent benzimidazoles are a kind of copper face antioxidants for printed wiring board, prevent the oxidation stain in atmosphere of wiring board copper face, and the wiring board for entering processing does not influence follow-up electronic welding performance, and the handling process is OSP by PCB industries.
OSP techniques are chemically, one layer of anti-oxidation film is formed on naked copper surface, the film has the advantages that impact resistance, moisture-proof, the main component of OSP films is to be entrained with the organometallic polymer of aliphatic acid and azole derivative small molecule, and this organometallic polymer provides required heat/corrosion resistance, copper tack and case hardness.In order to bear the temperature conditionss of lead free manufacture technique, the decomposition temperature of organometallic polymer necessarily be greater than the melting temperature of lead-free solder, and otherwise the principal component of OSP films is decomposed after lead free manufacture technique.The key factor that protect copper face is not influenceed by oxidation is the volatility of azole derivative, and during Lead-free Reflow Soldering, the inoxidizability of copper is significantly reduced because of the volatilization of OSP film small moleculars.Therefore high performance OSP raw materials are the trend of industry development.
The OSP series of products that we develop include 2- heptyl benzimidazole, 2- p-chlorobenzyls benzimidazole, 2-（2,4- dichloro benzyls）High performance OSP raw materials in-benzimidazole etc., there is the advantages that heat-resist, welding rate is high and cheap, and technique simply waits.Therefore the welcome of wiring board manufacturing enterprise is obtained.But production process is organic synthesis process, more accessory substance can be produced, the presence of these accessory substances can largely effect on the heat resistance of product, the problems such as causing downstream product to crystallize, so the purifying of product is extremely important.
The content of the invention
It is an object of the invention to provide a kind of purification process of 2- substituents benzimidazole, the synthetic method of usual 2- substituted benzimidazoles class compound has several:O-phenylenediamine reacts in a solvent with organic acid direct polycondensation, o-phenylenediamine and organic aldehyde, oxidized production 2- substituted benzimidazoles etc..During surface treatment, especially to the 2- substituted benzimidazole used for wiring board processing, higher requirement is had.Common product requirement is pure white colourless, and content reaches more than 98%.
The technical solution of the present invention is 2- substituent benzimidazole crude products, in 1000ml conical flasks, dissolved by heating with 300ml 95% ethanol, maintain the temperature at 65-70 DEG C, with 40 watts of ultra violet lamp 10-120 minutes, solution is by there is miscellaneous purple to gradate to be faint yellow in bottle, solution adds 1-10 grams of activated carbon, flow back 10-60 minutes, it is filtered to remove activated carbon, 200ml is added in system to 250ml water, let cool after boiling, -18 DEG C of bad border left overnights, filter, crystal is washed with a small amount of 50% frozen ethanol, it is dried to obtain pure white flat crystal, yield 78%-81.3%, HPLC examines its content to reach 98.6%--99.2%.
The substituent of 2- substituents benzimidazole crude product described above have heptyl, p-chlorobenzyl,（2,4- dichloro benzyls）.
Impurity color of the present invention is reddish violet, bluish violet.
The present invention is applied to purify with decolouring of the corresponding organic acid through the generated 2- substitutions-benzimidazole of following reaction through o-phenylenediamine.
With the synthesized benzimidazole crude product of o-phenylenediamine and organic acid condensation, often with deeper red to bluish violet.It is to recrystallize in organic solvent in general industrialized production, in order to remove coloring matter, it is necessary to add more decolorising agent, recrystallize ability repeatedly arrives qualified compound.
The beneficial effects of the invention are as follows：Simplify the method for such compound purge process.Its core is：After 2- substituted benzimidazole crude products are dissolved with organic solvent, ultraviolet to carry out illumination to purification system to visible ray, the color of system can decorporate, and can obtain pure white by conventional recrystallization processing, a step, purity reaches more than 98% product.
Embodiment
Embodiment 1
2- heptyl benzimidazole purifies
100 grams are taken with o-phenylenediamine and 2- heptyl benzimidazole crude products made from octanoic acid reaction, in 1000 milliliters of conical flasks, dissolved by heating with 300 milliliter of 95% ethanol, maintain the temperature at 65-70 °C, with 40 watts of ultra violet lamps 10 minutes, solution is gradually transformed into faint yellow by reddish violet in bottle, solution adds 1 gram of activated carbon, flow back 10-60 minutes, it is filtered to remove activated carbon, 200 milliliters of water are added in system, let cool after boiling, -18 DEG C of environment left overnights, filter, crystal is washed with a small amount of 50% frozen ethanol, it is dried to obtain pure white flat crystal, yield 81.3%, HPLC examines its content to reach 98.8%.
Embodiment 2
The purifying of 2- p-chlorobenzyl benzimidazoles
100 grams of 2- p-chlorobenzyl benzimidazole crude products made from o-phenylenediamine and the reaction of 2- 4-Chlorophenylacetic acids are taken in 1000 milliliters of conical flasks, dissolved by heating with 300 milliliter of 95% ethanol, maintain the temperature at 65-70 °C, with 40 watts of ultra violet lamps 60 minutes, solution is gradually transformed into faint yellow by bluish violet in bottle, solution adds 5 grams of activated carbons, flow back 10-60 minutes, it is filtered to remove activated carbon, 250 milliliters of water are added in system, let cool after boiling, -18 DEG C of environment left overnights, filter, crystal is washed with a small amount of 50% frozen ethanol, it is dried to obtain pure white pin Like crystal, yield 78%, HPLC examines its content to reach 98.6%.The requirement for preparing wiring board protection liquid medicine is fully achieved in product quality.
Embodiment 3
2-（2,4- dichloro benzyls）Benzimidazole purifies
100 grams are taken with o-phenylenediamine and 2,2- made from the reaction of 4- fenacs（2,4- dichloro benzyls）Benzimidazole crude product is in 1000 milliliters of conical flasks, dissolved by heating with 300 milliliter of 95% ethanol, maintain the temperature at 65-70 °C, with 40 watts of ultra violet lamps 120 minutes, solution is gradually transformed into faint yellow by bluish violet in bottle, solution adds 10 grams of activated carbons, flows back 10-60 minutes, is filtered to remove activated carbon, 250 milliliters of water are added in system, let cool, -18 DEG C of environment left overnights, filter after boiling, crystal is washed with a small amount of 50% frozen ethanol, pure white pin Like crystal, yield 78% are dried to obtain, HPLC examines its content to reach 99.2%.The requirement for preparing wiring board protection liquid medicine is fully achieved in product quality.
In order to prove important function of the ultra violet lamp to decolouring, we have done next experiment, are not have to ultra violet lamp.
Embodiment 4
2-（2,4- dichloro benzyls）Benzimidazole purifies
100 grams are taken with o-phenylenediamine and 2,2- made from the reaction of 4- fenacs（2,4- dichloros
Benzyl）Benzimidazole crude product is dissolved by heating in 1000 milliliters of conical flasks with 300 milliliter of 95% ethanol, maintains temperature at 65-70 °C, solution adds 1-10 grams of activated carbon, flows back 10-60 minutes, is filtered to remove activated carbon, 250 milliliters of water are added in system, let cool, -18 DEG C of environment left overnights, filter after boiling, crystal is washed with a small amount of 50% frozen ethanol, pink pin Like crystal, yield 77% are dried to obtain, HPLC examines its content to reach 98.5%.
Example 3 and the contrast of example 4 find that the system of no ultra violet lamp, color is difficult to slough, stoste can be caused to darken during for preparing OSP solution, judgement of the operating personnel to quality on line is influenceed, through customers' responsiveness, purple removing is incomplete, is more easily caused downstream product crystallization situation and protrudes.
Claims (3)
- The purification process of 1.2- substituent benzimidazoles, it is characterized in that 2- substituent benzimidazole crude products, in 1000ml conical flasks, dissolved by heating with 300ml 95% ethanol, maintain the temperature at 65-70 DEG C, with 40 watts of ultra violet lamp 10-120 minutes, solution is by there is miscellaneous purple to gradate to be faint yellow in bottle, solution adds 1-10 grams of activated carbon, flow back 10-60 minutes, it is filtered to remove activated carbon, 200ml is added in system to 250ml water, let cool after boiling, -18 DEG C of environment left overnights, filter, crystal is washed with a small amount of 50% frozen ethanol, it is dried to obtain pure white flat crystal, yield 78%-81.3%, HPLC examines its content to reach 98.6%--99.2%.
- 2. the purification process of the 2- substituent benzimidazoles according to claims 1, it is characterized in that the substituent of the 2- substituents benzimidazole crude product has a heptyl, p-chlorobenzyl,（2nd, 4- dichloro benzyls）.
- 3. the purification process of 2- substituents benzimidazole according to claim 1, it is characterized in that impure product is reddish violet or bluish violet.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610380831.5A CN107445901A (en) | 2016-06-01 | 2016-06-01 | The purification process of 2- substituent benzimidazoles |
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| CN201610380831.5A CN107445901A (en) | 2016-06-01 | 2016-06-01 | The purification process of 2- substituent benzimidazoles |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114656405A (en) * | 2020-12-22 | 2022-06-24 | 广州和为医药科技有限公司 | Preparation method of difluoromethylbenzimidazole |
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2016
- 2016-06-01 CN CN201610380831.5A patent/CN107445901A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114656405A (en) * | 2020-12-22 | 2022-06-24 | 广州和为医药科技有限公司 | Preparation method of difluoromethylbenzimidazole |
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| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20171208 |
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| WD01 | Invention patent application deemed withdrawn after publication |