CN103833512B - Method of synthesizing o-dibromobenzene by diazotization in one step at high temperature - Google Patents
Method of synthesizing o-dibromobenzene by diazotization in one step at high temperature Download PDFInfo
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- CN103833512B CN103833512B CN201410058576.3A CN201410058576A CN103833512B CN 103833512 B CN103833512 B CN 103833512B CN 201410058576 A CN201410058576 A CN 201410058576A CN 103833512 B CN103833512 B CN 103833512B
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Abstract
The invention relates to the technical field of preparation of o-dibromobenzene, and particularly relates to a method of synthesizing o-dibromobenzene by diazotization in one step at high temperature. The method comprises the following steps: sequentially adding hydrobromic acid, cuprous oxide and bromaniline into a reactor with a stirrer, a condenser and a thermometer; heating to over 80 DEG C; maintaining the temperature within 80-100 DEG C; dropping aqueous solution of sodium nitrite under liquid level; after dropping, distilling with steam to obtain the product, and separating out the oil layer; washing once by thermonatrite; after washing once, distilling under reduced pressure to obtain a product. According to the preparation method of o-dibromobenzene provided by the invention, diazotization and decomposition reaction are carried out by using a one-step method, so that the energy consumption and investment on freezing equipment are greatly reduced, and the product is stable in yield, and yield fluctuation caused by refrigeration of a two-step method is avoided. The continuous production capacity is greatly improved, the quality of the product is consistent with that of the two-step method, the yield is slightly higher, the preparation process is simple, convenient and feasible, the product is good in quality, and the technical demand is low, so that the method is a method suitable for industrialized production.
Description
Technical field
The present invention relates to the preparing technical field of o-dibromobenzene, especially relate to the method for diazotization one-step synthesis o-dibromobenzene under a kind of high temperature.
Background technology
O-dibromobenzene is a kind of colourless or weak yellow liquid, is commonly used for medicine intermediate.The production method of traditional o-dibromobenzene is produced by diazotization Sum decomposition reaction two-step approach, and when two-step approach produces o-dibromobenzene, diazonium salt is easily coupled, and makes product yield low.
Summary of the invention
The invention provides the method for diazotization one-step synthesis o-dibromobenzene under a kind of high temperature, single stage method is used to carry out diazotization and decomposition reaction, greatly reduce energy consumption and refrigerating apparatus investment, and product yield is stablized, yield will be caused to fluctuate because of the refrigeration reason of two-step approach, continuous seepage ability improves greatly, and the quality of product is consistent with two-step approach, and yield is slightly high.
The technical solution adopted for the present invention to solve the technical problems is: a kind of method of diazotization one-step synthesis o-dibromobenzene under high temperature, and preparation process is as follows:
Hydrogen bromide, Red copper oxide, o-bromoaniline are added successively in the reactor with agitator, condenser, thermometer, be heated to more than 80 DEG C, between keeping 80-100 DEG C, from liquid level, drip the aqueous solution of Sodium Nitrite, after dripping off, steam distillation goes out product, divide oil-yielding stratum, scale washing once, is washed once, underpressure distillation product.
Particularly, be in 48% Hydrogen bromide, 10g Red copper oxide, the four-hole boiling flask of 172g o-bromoaniline input with agitator, condenser, thermometer by 500g massfraction, stirring is warming up to more than 80 DEG C, the solution that 72g Sodium Nitrite is dissolved in 100g water is dripped under liquid level, after dripping off, change water distilling apparatus band water and distill out product, divide oil-yielding stratum, be that 5% liquid caustic soda is washed once with 100mL massfraction, again with after 100mL washing once, point oil-yielding stratum, steams product 194g under decompression, content 99.2%, yield 82%.
The invention has the beneficial effects as follows, the method of diazotization one-step synthesis o-dibromobenzene under a kind of high temperature provided by the invention, single stage method is used to carry out diazotization and decomposition reaction, greatly reduce energy consumption and refrigerating apparatus investment, and product yield is stablized, yield will be caused to fluctuate because of the refrigeration reason of two-step approach, continuous seepage ability improves greatly, the quality of product is consistent with two-step approach, and yield is slightly high, and preparation process is simple and easy to do, reduce the danger of diazonium salt, good product quality, processing requirement is low, is a kind of applicable industrial method.
Accompanying drawing explanation
Below in conjunction with drawings and Examples, the present invention is further described.
Fig. 1 is the nuclear magnetic spectrogram of the o-dibromobenzene that embodiment 1 is synthesized;
Fig. 2 is the infrared spectra spectrogram of the o-dibromobenzene that embodiment 1 is synthesized.
Embodiment
Below in conjunction with specific embodiment, further the present invention is set forth, should be understood that and quote embodiment only for illustration of the present invention, and be not used in and limit the scope of the invention.
Embodiment 1
Be in 48% Hydrogen bromide, 10g Red copper oxide, the four-hole boiling flask of 172g o-bromoaniline input with agitator, condenser, thermometer by 500g massfraction, stirring is warming up to more than 80 DEG C, drips the solution that 72g Sodium Nitrite is dissolved in 100g water, after dripping off under liquid level, change water distilling apparatus band water and distill out product, dividing oil-yielding stratum, is that 5% liquid caustic soda is washed once with 100mL massfraction, then with after 100mL washing once, divide oil-yielding stratum, product 194g is steamed, content 99.2%, yield 82% under decompression.Can confirm that the product that embodiment finally obtains is o-dibromobenzene from Fig. 1 and Fig. 2.
With above-mentioned according to desirable embodiment of the present invention for enlightenment, by above-mentioned description, relevant staff in the scope not departing from this invention technological thought, can carry out various change and amendment completely.The technical scope of this invention is not limited to the content on specification sheets, must determine its technical scope according to right.
Claims (1)
1. the method for diazotization one-step synthesis o-dibromobenzene under high temperature, is characterized in that:
Be in 48% Hydrogen bromide, 10g Red copper oxide, the four-hole boiling flask of 172g o-bromoaniline input with agitator, condenser, thermometer by 500g massfraction, stirring is warming up between 80-100 DEG C, the solution that 72g Sodium Nitrite is dissolved in 100g water is dripped under liquid level, after dripping off, change water distilling apparatus band water and distill out product, divide oil-yielding stratum, be that 5% liquid caustic soda is washed once with 100mL massfraction, again with after 100mL washing once, divide oil-yielding stratum, product 194g is steamed, content 99.2%, yield 82% under decompression.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410058576.3A CN103833512B (en) | 2014-02-20 | 2014-02-20 | Method of synthesizing o-dibromobenzene by diazotization in one step at high temperature |
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| CN201410058576.3A CN103833512B (en) | 2014-02-20 | 2014-02-20 | Method of synthesizing o-dibromobenzene by diazotization in one step at high temperature |
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| CN103833512A CN103833512A (en) | 2014-06-04 |
| CN103833512B true CN103833512B (en) | 2015-07-01 |
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| CN106905105A (en) * | 2017-02-16 | 2017-06-30 | 盐城市龙升化工有限公司 | A kind of preparation method of o-dibromobenzene |
| CN108947765A (en) * | 2018-08-15 | 2018-12-07 | 江苏常源新材料科技有限公司 | A kind of method of bis-diazotized reaction one-step synthesis o-dibromobenzene |
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| GB426403A (en) * | 1933-10-03 | 1935-04-03 | Ig Farbenindustrie Ag | Process for the manufacture of hydroxydiphenylene compounds and derivatives thereof |
| CN101302190B (en) * | 2008-06-30 | 2011-07-27 | 河北亚诺化工有限公司 | Method for preparing 2,3-dichloropyridine |
| CN101898976B (en) * | 2010-07-23 | 2013-06-19 | 常州大学 | Preparation method of 2-fluoro-5-bromoxynil |
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