CN102241595A - Photocatalytic method for preparing 3,4-dichloroaniline - Google Patents
Photocatalytic method for preparing 3,4-dichloroaniline Download PDFInfo
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- CN102241595A CN102241595A CN2011101151518A CN201110115151A CN102241595A CN 102241595 A CN102241595 A CN 102241595A CN 2011101151518 A CN2011101151518 A CN 2011101151518A CN 201110115151 A CN201110115151 A CN 201110115151A CN 102241595 A CN102241595 A CN 102241595A
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- dichloronitrobenzene
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Abstract
The invention provides a method for preparing 3,4-dichloroaniline by photocatalytic reduction, which comprises the following steps: selecting a photocatalytic reactor which is required to have a gas inlet, a gas outlet and a cooling water feeding and discharging system and of which the wall is required to allow ultraviolet light with a wavelength of less than 387.5 nanometers to transmit, filling an organic solvent into the photocatalytic reactor and dissolving 3,4-dichloronitrobenzene in the organic solvent; adding solid powdered TiO2 into the 3,4-dichloronitrobenzene containing solvent as a catalyst, and also adding a surfactant subwet159 as an additive; in an atmosphere of inert nitrogen, performing the dark absorption of the 3,4-dichloronitrobenzene and solid powdered TiO2, which are dissolved in the organic solvent, for 10 minutes; and in the atmosphere of inert nitrogen, irradiating the transparent reactor containing the 3,4-dichloronitrobenzene and solid powdered TiO2 to obtain 3,4-dichloroaniline. The preparation method provided by the invention is green, environment-friendly, safe and nontoxic, the product yield of the preparation method is high, and the cost of the preparation method is low.
Description
Technical field
The present invention relates to the organism synthetic process, particularly a kind of photo catalytic reduction preparation 3, the method for 4-dichlorphenamide bulk powder.
Background technology
3, and the 4-dichlorphenamide bulk powder (3,4-Dichloroaniline) be the important intermediate of Multiple Pesticides, medicine, dyestuff, pigment, fine chemical product, also be the biological activity intermediate, purposes is very extensive.A large amount of raw materials requirement in China weedicide market are 3, and the widely-used of 4-dichlorphenamide bulk powder laid a good foundation, thereby develop this product and have good market outlook.
3, the synthetic method that the 4-dichlorphenamide bulk powder is commonly used is 3, and 4-dichloronitrobenzene reduction method generally can adopt iron powder reducing, catalytic hydrogenating reduction, sodium sulfide reducing.It is big, seriously polluted that the iron powder reducing method produces quantity of three wastes; The catalytic hydrogenating reduction method need high temperature, high-tension apparatus, to resistance to pressure, the erosion resistance of equipment require high, the operation unsafe factor is more; Sodium sulfide reducing method cost height, yield be low, it is big, seriously polluted to produce quantity of three wastes.
Summary of the invention
At having problems in the above-mentioned technology, the purpose of this invention is to provide a kind of photo catalytic reduction preparation 3, the method for 4-dichlorphenamide bulk powder is to reach environmental protection, safety, high yield, target cheaply.
For realizing above-mentioned target, the technical solution used in the present invention has provided a kind of photo catalytic reduction preparation 3, the method for 4-dichlorphenamide bulk powder, and this method may further comprise the steps:
(1) selective light catalyticreactor, reactor need be provided with air inlet, gives vent to anger and pass in and out cooling water system, and reactor wall needs wavelength is seen through less than the UV-light of 387.5nm, in described photo catalysis reactor, the organic solvent of packing into, and with 3, the 4-dichloronitrobenzene is dissolved in this organic solvent;
(2) be dissolved with 3 to what step (1) obtained, add solid powdery TiO in the organic solvent of 4-dichloronitrobenzene
2As catalyzer, add tensio-active agent subwet159 simultaneously as additive;
(3) in the inert nitrogen gas atmosphere, step (2) obtains is dissolved in 3 in the organic solvent, 4-dichloronitrobenzene and solid powdery TiO
2Catalyzer secretly adsorbs, and the time of dark absorption is 10min;
(4) in the inert nitrogen gas atmosphere, be equipped with 3 with ultraviolet irradiation step (3), 4-dichloronitrobenzene and solid powdery TiO
2The printing opacity reactor of catalyzer obtains 3, the 4-dichlorphenamide bulk powder.
Effect of the present invention is that this preparation method has following advantage:
(1) this preparation method's environmental protection has good benefits in environment, meets the fundamental principle of Green Chemistry.Present method prevents and has reduced the generation of pollutent from the source, catalyzer that uses in the technology and organic solvent can both recycling uses, and use catalyzer of the same race after changing reaction conditions, can remove the pollutent that produces among this preparation technology, therefore the pollutent of this preparation method generation and discharging is few, sees table 1 for details.
Table 1 environmental pollution assessment item result
(2) this preparation method is safe and harmless.Present method adopts highly active catalyzer, and reaction conditions gentleness, whole process of preparation have reduced the generation of mishap to greatest extent.
(3) this preparation method's product yield height meets the fundamental principle of cleaner production.The catalyzer that present method is used has highly selective, and byproduct of reaction is less, final product 3, and the yield of 4-dichlorphenamide bulk powder is up to 71.30%.
(4) this preparation method is energy source with luminous energy, and the units of product cost is low, has good economic benefit.
Description of drawings
Fig. 1 is photo catalytic reduction preparation 3 of the present invention, the Experimental equipment of 4-dichlorphenamide bulk powder;
Fig. 2 is the high performance liquid phase figure of the embodiment of the invention 1.
Among the figure: 1, light source 2, magnetic stirring apparatus
Embodiment
To photo catalytic reduction preparation 3 of the present invention, the method for 4-dichlorphenamide bulk powder is illustrated in conjunction with the embodiments.
Photo catalytic reduction preparation 3 of the present invention, the method of 4-dichlorphenamide bulk powder is based on following invention thought: when with wavelength less than the rayed of semi-conductor energy gap during as the semi-conductor of catalyzer, electronics on the semi-conductor valence band is stimulated and transits to conduction band, produces the hole on valence band.Conduction band electron has very strong reducing power, and the electron acceptor(EA) that is adsorbed on semiconductor surface is reduced, and as conduction band electron the aromatic nitro compound that is adsorbed on semiconductor surface is reduced, and specifically is to make to be adsorbed on TiO in the present invention
23 of catalyst surface, the 4-dichloronitrobenzene is reduced to 3, the 4-dichlorphenamide bulk powder.
Photo catalytic reduction preparation 3 of the present invention, the reaction scheme of the method for 4-dichlorphenamide bulk powder is:
Photo catalytic reduction preparation 3 of the present invention among Fig. 1, the Experimental equipment of 4-dichlorphenamide bulk powder, wherein light source 1 is the UV-light of wavelength less than 387.5nm, air inlet is a nitrogen, and is stable for guaranteeing the reactor internal gas pressure, is provided with escape pipe, because of can discharging heat energy, reaction cause reactor awfully hot, so reactor adopts the cooling of turnover water quench, this has guaranteed that also this reaction energy source is a luminous energy, and non-thermal energy.The high performance liquid phase figure of embodiment 1 among Fig. 2 in the inert nitrogen gas atmosphere, is equipped with less than the UV-irradiation of 387.5nm with wavelength and is dissolved in 3 in the anhydrous methanol, 4-dichloronitrobenzene and solid powdery TiO
2The transparent reaction container of catalyzer, total irradiation time are 20h, and wherein the irradiation time of a～d is respectively 4,8,12,16h.
A kind of photo catalytic reduction preparation 3 of the present invention, the concrete steps of the method for 4-dichlorphenamide bulk powder are as follows:
Be provided with air inlet, giving vent to anger and passing in and out cooling water system, and reactor wall can make in the photo catalysis reactor that wavelength sees through less than the 387.5nm UV-light, with 3 of different concns, the 4-dichloronitrobenzene is dissolved in the organic solvent of anhydrous methanol, Virahol, dehydrated alcohol or acetonitrile; To being dissolved with 3, add the solid powdery TiO of different amounts in the organic solvent of 4-dichloronitrobenzene
2, solid powdery TiO
2The TiO that comprises doped with non-metals N
2, doping metals Ag TiO
2, doping metals La TiO
2, doping metals Fe TiO
2, porous TiO
2Or commercially available P25 type TiO
2As catalyzer, add tensio-active agent subwet159 simultaneously as additive; In the inert nitrogen gas atmosphere, under the stirring of magnetic stirring apparatus 2, be dissolved in 3 in the organic solvent, 4-dichloronitrobenzene and as the solid powdery TiO of catalyzer
2Carrying out 10min earlier and secretly adsorb, is 3360 μ W/cm with yield of radiation subsequently
2Or 4120 μ W/cm
2UV-irradiation be equipped with 3,4-dichloronitrobenzene and solid powdery TiO
2The transparent reaction container time of catalyzer is 12～20h, obtains 3, the 4-dichlorphenamide bulk powder.
Embodiment 3 is except replacing anhydrous methanol to do the solvent with dehydrated alcohol, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 13.04%.
Embodiment 4 is except replacing anhydrous methanol to do the solvent with acetonitrile, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 1.10%.
Embodiment 5 is except with porous TiO
2The quality of powder becomes 0.1g by 0.3g, and promptly catalyst concentration is become outside the 2g/L by 6g/L, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 41.85%.
Embodiment 6 is except with porous TiO
2The quality of powder becomes 0.2g by 0.3g, and promptly catalyst concentration is become outside the 4g/L by 6g/L, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 53.82%.
Embodiment 7 is except with porous TiO
2The quality of powder becomes 0.4g by 0.3g, and promptly catalyst concentration is become outside the 8g/L by 6g/L, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 31.24%.
Embodiment 8 is except with porous TiO
2The quality of powder becomes 0.5g by 0.3g, and promptly catalyst concentration is become outside the 10g/L by 6g/L, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 10.32%.
Embodiment 9 is except using yield of radiation 3360 μ W/cm
2The 150W ultraviolet lamp replace yield of radiation 4120 μ W/cm
2The ultraviolet lamp of 250W, the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 56.02%.
Embodiment 10 is except with 3, and the quality of 4-dichloronitrobenzene becomes 0.1g by 0.5g, and promptly its concentration becomes 2g/L by 10g/L, and the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 23.56%.
Embodiment 11 is except with 3, and the quality of 4-dichloronitrobenzene becomes 0.3g by 0.5g, and promptly its concentration becomes 6g/L by 10g/L, and the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 61.15%.
Embodiment 12 is except the TiO with doping 20%N
2Powder replaces porous TiO
2Powder, the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 58.50%.
Embodiment 13 is except the TiO with doping 1%Ag
2Powder replaces porous TiO
2Powder, the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 23.15%.
Embodiment 14 is except the TiO with doping 0.1%Ag
2Powder replaces porous TiO
2Powder, the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 21.23%.
Embodiment 15 is except the TiO with doping 5%Ag
2Powder replaces porous TiO
2Powder, the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 19.86%.
Embodiment 16 is except the TiO with doping 5%La
2Powder replaces porous TiO
2Powder, 16～22 medium ultraviolet light irradiation times of embodiment become outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 13.57%.
Embodiment 17 is except the TiO with doping 5%Fe
2Powder replaces porous TiO
2Powder, the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 10.20%.
Embodiment 18 is except with commercially available P25 type TiO
2Powder replaces porous TiO
2Powder, the ultra violet lamp time becomes outside the 12h simultaneously, and other reaction conditionss are with embodiment 1, and the result obtains 3, and 4-dichlorphenamide bulk powder productive rate is 9.75%.
By embodiment 1～4 as can be seen, under the same reaction conditions, different solvents has a significant impact the preparation productive rate, in used anhydrous methanol, Virahol, dehydrated alcohol, four kinds of organic solvents of acetonitrile, obtain 3 when making solvent with anhydrous methanol, the productive rate of 4-dichlorphenamide bulk powder is the highest.
By embodiment 1,5～8 as can be seen, under the same reaction conditions, different catalyst concns has a significant impact the preparation productive rate, in the catalyst concn of used 2g/L, 4g/L, 6g/L, 8g/L and 10g/L, obtain 3 under the catalyst concn condition of 6g/L, the productive rate of 4-dichlorphenamide bulk powder is the highest.
By embodiment 1,9 as can be seen, under the same reaction conditions, different light sources has a significant impact the preparation productive rate, and the ultraviolet lamp yield of radiation is big more, and reaction yield is high more.
By embodiment 1,10～11 as can be seen, under the same reaction conditions, different 3,4-dichloronitrobenzene concentration has a significant impact the preparation productive rate, in used 2g/L, 6g/L and 10g/L concentration, obtain 3 under the concentration conditions of 10g/L, the productive rate of 4-dichlorphenamide bulk powder is the highest, and this shows along with 3, the rising of 4-dichloronitrobenzene concentration, 3, the productive rate of 4-dichlorphenamide bulk powder increases.
By embodiment 1,12～18 as can be seen, under the same reaction conditions, different catalysts has a significant impact the preparation productive rate, in used catalyzer, obtains 3, and the productive rate of 4-dichlorphenamide bulk powder is followed successively by on earth by height: porous TiO
2The TiO of＞doping 20%N
2The TiO of＞doping 1%Ag
2The TiO of＞doping 0.1%Ag
2The TiO of＞doping 5%Ag
2The TiO of＞doping 5%La
2The TiO of＞doping 5%Fe
2＞commercially available P25 type TiO
2
Claims (5)
1. photo catalytic reduction preparation 3, the method for 4-dichlorphenamide bulk powder, this method may further comprise the steps:
(1) selective light catalyticreactor, reactor need be provided with air inlet, gives vent to anger and pass in and out cooling water system, and reactor wall needs wavelength is seen through less than the UV-light of 387.5nm, in described photo catalysis reactor, the organic solvent of packing into, and with 3, the 4-dichloronitrobenzene is dissolved in the organic solvent;
(2) be dissolved with 3 to what step (1) obtained, add solid powdery TiO in the organic solvent of 4-dichloronitrobenzene
2As catalyzer, add tensio-active agent subwet159 simultaneously as additive;
(3) in the inert nitrogen gas atmosphere, step (2) obtains is dissolved in 3 in the organic solvent, 4-dichloronitrobenzene and solid powdery TiO
2Catalyzer secretly adsorbs, and the time of dark absorption is 10min;
(4) in the inert nitrogen gas atmosphere, be equipped with 3 with ultraviolet irradiation step (3), 4-dichloronitrobenzene and solid powdery TiO
2The printing opacity reactor of catalyzer obtains 3, the 4-dichlorphenamide bulk powder.
2. method according to claim 1 is characterized in that: described organic solvent is methyl alcohol, ethanol, Virahol or acetonitrile.
3. method according to claim 1 is characterized in that: the described ultraviolet light wavelength of step (4) is less than 387.5nm, and irradiation time is 12～20h.
4. method according to claim 1 is characterized in that: described solid powdery TiO
2TiO in the catalyzer
2Be meant the TiO of doped with non-metals N
2, doping metals Ag TiO
2, doping metals La TiO
2, doping metals Fe TiO
2, porous TiO
2Or commercially available P25 type TiO
2, median size is at 10～15nm, TiO
2Crystal formation is Detitanium-ore-type.
5. method according to claim 1 is characterized in that: described 3, the 4-dichloronitrobenzene has following structure:
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106083732A (en) * | 2016-06-22 | 2016-11-09 | 袁氏(宿迁)生物技术有限公司 | A kind of preparation method of high yield different luminol luminescence reagent |
| CN112812027A (en) * | 2021-01-06 | 2021-05-18 | 湘潭大学 | Methoxyaniline compound and synthetic method thereof |
| WO2022032879A1 (en) * | 2020-08-10 | 2022-02-17 | 天津凯莱英制药有限公司 | Photochemical synthesis method for heteroaryl amine compound |
| CN115448843A (en) * | 2022-09-16 | 2022-12-09 | 中国科学技术大学 | Preparation method of aniline compound |
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| CN1634862A (en) * | 2004-10-25 | 2005-07-06 | 天津大学 | Process for photo catalytic reduction preparation of p-chloroaniline |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106083732A (en) * | 2016-06-22 | 2016-11-09 | 袁氏(宿迁)生物技术有限公司 | A kind of preparation method of high yield different luminol luminescence reagent |
| WO2022032879A1 (en) * | 2020-08-10 | 2022-02-17 | 天津凯莱英制药有限公司 | Photochemical synthesis method for heteroaryl amine compound |
| CN112812027A (en) * | 2021-01-06 | 2021-05-18 | 湘潭大学 | Methoxyaniline compound and synthetic method thereof |
| CN115448843A (en) * | 2022-09-16 | 2022-12-09 | 中国科学技术大学 | Preparation method of aniline compound |
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Address after: 300384 Xiqing District, Tianjin Jing Jing Road, No. 26 Patentee after: Tianjin Chengjian University Address before: 300384 Xiqing District, Tianjin Jing Jing Road, No. 26 Patentee before: Tianjin Institute of Urban Construction |
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Effective date of registration: 20160805 Address after: 334200, Dexing, Jiangxi province Tuen Industrial Park Patentee after: DEXING DEBANG CHEMICAL Co.,Ltd. Address before: 300384 Xiqing District, Tianjin Jing Jing Road, No. 26 Patentee before: Tianjin Chengjian University |