CN104418752A - Method for synthesizing single nitro-o-xylene employing catalytic nitration in micro-reactor - Google Patents
Method for synthesizing single nitro-o-xylene employing catalytic nitration in micro-reactor Download PDFInfo
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Abstract
The invention discloses a method for synthesizing single nitro-o-xylene employing catalytic nitration in a micro-reactor. The used catalyst is a rare-earth metal salt; the raw materials are o-xylene and nitric acid; and the raw materials are injected into a micro-channel reactor to be nitrified by a high-pressure constant flow pump at ordinary pressure. The method is free of a solvent; and the reinforcing action of the micro-channel reactor on quality and heat transfer processes is well utilized.
Description
Technical field
The invention belongs to organic synthesis field, relate to the synthesis of single nitro o-Xylol, specifically one utilizes HNO
3make nitrating agent, trifluoromethanesulfonic acid rare earth metal salt makees catalyzer, and catalysis o-Xylol generation nitration reaction, in micro passage reaction, catalytic nitration synthesizes the method for single nitro o-Xylol.
Background technology
O-Xylol can obtain two kind of one nitration product through nitrated, and be 3-nitro o-Xylol (3-NOX) and 4-nitro o-Xylol (4-NOX), wherein 4-nitro o-Xylol is new herbicides pendimethalin and vitamins B
2intermediate, it also has on agricultural chemicals, medicine and dyestuff applies quite widely.
Most nitric-sulfuric acid nitrofication process synthesis adopting o-Xylol traditionally, before there is nitrification ability in this method, speed is fast, etc. feature, but the method regioselectivity is poor, 4-nitro o-Xylol only accounts for 31% ~ 55% of total nitration product, and by product 3-nitro o-Xylol accounts for 55% ~ 69%, and produce a large amount of spent acid, contaminate environment; The severe corrosive of nitric-sulfuric acid can badly damaged equipment, and the side reactions such as the polynitration occurred in reaction process, oxidation also can produce serious potential safety hazard.
Therefore, many researchists have carried out a large amount of research work, mainly comprise the research of the nitrated new catalyst of o-Xylol and nitrating agent.(the Smith K. J.Org.Chem.1998 such as Smith; 23:8448-845) under mild conditions; be catalyzer with H beta-zeolite molecular sieve; nitric acid stoichiometrically and acetic anhydride catalytic nitration o-Xylol; total recovery reaches more than 99%; 4-NOX accounts for 44% of total nitration product, and by product also generates the 4-acyl group o-Xylol of 23% except generating 32% 3-NOX, and in product, the overall selectivity of 4-NOX is not very very high.(the Olah G. A. Communications such as Olah, 1978,9:690-691) research finds, take perfluorinated sulfonic resin as catalyzer, consumption is 10% ~ 25%, Butylnitrate ester is under the condition of nitrating agent, and obtaining optimal yield is that 98%, 4-NOX accounts for 53% of total nitration product, 3-NOX accounts for 47%, this product isomer ratio and nitric-sulfuric acid system are more or less the same, and perfluorinated sulfonic resin price costly, and economic serviceability is not high.Jing Dan etc. (Jing Dan. modern chemical industry. 2010,20 (2), 223-225) investigate P
2o
5the selectivity that under effect, o-Xylol is nitrated is at P
2o
5massfraction 4.5%, nitric acid and o-Xylol mol ratio 1.15, dehydrating value of sulfuric acid (D.V.S) are 3.16, temperature of reaction 20 DEG C, reaction times 4 h time, in nitration product, 3-NOX and 4-NOX mol ratio reaches 0.94, significantly reduce compared with 1.35 of nitric-sulfuric acid, o-xylene conversion reaches 97.6%; But P
2o
5comparatively large to the corrodibility of equipment, be not suitable for large-scale industrial production.
Summary of the invention
The object of the invention is to utilize HNO
3make nitrating agent, trifluoromethanesulfonic acid rare earth metal salt makees catalyzer, and catalysis o-Xylol generation nitration reaction, in micro passage reaction, catalytic nitration synthesizes the method for single nitro o-Xylol.
The technical solution realizing the object of the invention is:
In microreactor, catalytic nitration synthesizes a method for single nitro o-Xylol, and using trifluoromethanesulfonic acid rare earth metal salt as catalyzer, with o-Xylol, nitric acid is raw material, in micro passage reaction, carry out nitration reaction with normal pressure; Concrete steps are:
The first step, by nitric acid and the mixing of trifluoromethanesulfonic acid rare earth metal salt, respectively by this mixed solution and o-Xylol respectively via the high pressure constant flow pump of accurate flow control being delivered to two entrances of micro passage reaction;
Second step, two strands of liquid mixes and contacts and after reacting, flow out enter receiving tank from the exit of reactor in micro passage reaction;
3rd step, after completion of the reaction, uses CH
2cl
2extraction, by solution left standstill, reaction system is divided into liquid-liquid diphase, lower floor is the nitration product of o-Xylol, upper strata is the mixture of rare earth metal salt, water, nitric acid, uses separating funnel to be separated two-phase, and lower floor's product obtains single nitro o-Xylol after washing, neutralization, drying; Upper strata containing the aqueous phase of rare earth metal salt after underpressure distillation except anhydrating and nitric acid, then through oven drying, reclaim trifluoromethanesulfonic acid rare earth metal salt.
Wherein, micro passage reaction at least has two entrances, an outlet, formed by glass processing, the reactor good corrosion resistance of glass material, inlet microchannel size and microchannel size inconsistent, intake vent size is larger, be conducive to like this improving microring array efficiency, in the microchannel that micro passage reaction has, it contains thousands of cylindricality hybrid channels, and large drop can be made to be dispersed into uniform milk sap, enhance mixed effect, be conducive to the carrying out of two phase reaction.
Control the volumetric flow rate of o-Xylol, nitric acid in the first step, make used molar ratio of material for n(nitric acid): n(o-Xylol)=1.0 ~ 3.0:1, n (o-Xylol): n ([Re (OTf)
3)=5 ~ 20:1.
In second step, temperature of reaction is 20 DEG C ~ 80 DEG C.In second step, the reaction times is 30s ~ 300s.
The preparation method of catalyzer trifluoromethanesulfonic acid rare earth metal salt:
The method prepared according to document of trifluoromethanesulfonic acid rare earth metal salt, adopts trifluoromethanesulfonic acid and excessive lanthanide metal oxide reflux in aqueous, and almost quantitative completing is reacted and obtain product.Reaction equation is as follows:
Typical preparation process is as follows: excessive metal oxide is joined the trifluoromethanesulfonic acid aqueous solution (50%
v/
v) in, reflux in neutral, is cooled to room temperature to solution, and cross and filter unreacted soild oxide, filtrate rotary evaporation, obtains pressed powder.
The present invention compared with prior art, its remarkable advantage is: the present invention adopts the technique utilizing trifluoromethanesulfonic acid rare earth metal salt catalysis o-Xylol nitrated in micro passage reaction, compared with the prior art, its gordian technique is to have employed the micro passage reaction different from conventional reactor, employing trifluoromethanesulfonic acid rare earth metal salt replaces sulfuric acid to carry out catalysis o-Xylol as catalyzer and react, and it is advantageous that:
(1) temperature of reaction is lower than industrial temperature of carrying out methylbenzene nitration reaction, and due to the specific surface area that microreactor is larger, reaction system heat exchange is fast, which reduces the possibility accidents caused because of misoperation;
(2) owing to not adding sulfuric acid in nitrifying process, use rare earth metal salt catalysis instead, decrease the generation of spent acid, 4-nitro o-Xylol in the product ratio improves greatly;
(3) micro-reaction can make material mix fast, can complete reaction in the short period of time, and can obtain nearly higher yield, has saved raw materials cost;
(4) trifluoromethanesulfonic acid rare earth metal salt is easy to prepare, moisture-stable, and catalyzer non-inactivation, can be recycled;
(5) this technique can continuous prodution, is easy to integrated and amplifies, having good prospects for commercial application.
Below in conjunction with accompanying drawing, the present invention is described in further detail.
Accompanying drawing explanation
Fig. 1 be the present invention a kind of in microreactor catalytic nitration synthesize the schema of the method for single nitro o-Xylol.
Fig. 2 is the structural representation of microreactor device of the present invention.
Embodiment
The following examples can make the present invention of those skilled in the art comprehend.
Embodiment 1
A certain amount of trifluoromethanesulfonic acid rare earth metal salt is dissolved in 95% nitrosonitric acid at normal temperature, under 80 DEG C of water bath with thermostatic control conditions, acid phase and organic phase solution are injected micro passage reaction by high pressure constant flow pump react, the mol ratio controlling nitric acid and o-Xylol is 2:1, o-Xylol and trifluoromethanesulfonic acid rare earth metal salt (Y (OTf)
3) mol ratio is 10:1, after 180s reaction, the continuous outflow reactor of reaction product, in collector, normal temperature is collected, and uses CH
2cl
2extraction, stratification, after separatory, organic layer is extremely neutral after alkali cleaning, washing and the washing of saturated NaCl solution, then through Mg
2sO
4drying, through by gas chromatographic detection, the ratio 1.98 of reaction conversion ratio reaches 90.1%, 3-NOX ratio to be 33.53%, 4-NOX proportion be 66.47%, 4-NOX/3-NOX.Aqueous phase except anhydrating and nitric acid, then through oven drying, reclaims trifluoromethanesulfonic acid rare earth metal salt after underpressure distillation.
Embodiment 2
Process is with embodiment 1, do not change the mol ratio of nitric acid and o-Xylol, the mol ratio changing o-Xylol and rare earth metal salt is 20:1, react by this charging, through vapor detection, reaction conversion ratio is 83.1%, 3-NOX ratio is 35.49%, 4-NOX proportion is the ratio 1.82 of 64.51%, 4-NOX/3-NOX.
Embodiment 3
Process is with embodiment 1, and only change the mol ratio of nitric acid and o-Xylol, the mol ratio of nitric acid and o-Xylol is 1:1, react by this charging, through vapor detection, reaction conversion ratio is 54.3%, the ratio 1.70 of 3-NOX ratio to be 37.03%, 4-NOX proportion be 62.97%, 4-NOX/3-NOX.
Embodiment 4
Process is with embodiment 1, and only change the mol ratio of nitric acid and o-Xylol, the mol ratio of nitric acid and toluene is 1.5:1, react by this charging, through vapor detection, reaction conversion ratio is 67.6%, the ratio 1.73 of 3-NOX ratio to be 36.59%, 4-NOX proportion be 63.41%, 4-NOX/3-NOX.
Embodiment 5
Process is with embodiment 1, and only change the mol ratio of nitric acid and o-Xylol, the mol ratio of nitric acid and toluene is 3:1, react by this charging, through vapor detection, reaction conversion ratio is 92.5%, the ratio 2.05 of 3-NOX ratio to be 32.69%, 4-NOX proportion be 67.31%, 4-NOX/3-NOX.
Embodiment 6
Process, with embodiment 1, only changes temperature of reaction, and temperature of reaction becomes 20 DEG C, through vapor detection, and the ratio 1.95 of reaction conversion ratio is 61.7%, 3-NOX ratio to be 35.25%, 4-NOX proportion be 64.75%, 4-NOX/3-NOX.
Embodiment 7
Process, with embodiment 1, only changes temperature of reaction, and temperature of reaction becomes 70 DEG C, through vapor detection, and the ratio 1.98 of reaction conversion ratio is 83.5%, 3-NOX ratio to be 33.88%, 4-NOX proportion be 66.12%, 4-NOX/3-NOX.
Embodiment 8
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses La (OTf) instead
3, through vapor detection, the ratio 2.05 of reaction conversion ratio reaches 89.4%, 3-NOX ratio to be 32.82%, 4-NOX proportion be 67.18%, 4-NOX/3-NOX.
Embodiment 9
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Pr (OTf) instead
3, through vapor detection, the ratio 2.00 of reaction conversion ratio reaches 88.6%, 3-NOX ratio to be 33.32%, 4-NOX proportion be 66.68%, 4-NOX/3-NOX.
Embodiment 10
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Nd (OTf) instead
3, through vapor detection, the ratio 2.06 of reaction conversion ratio reaches 90.4%, 3-NOX ratio to be 32.64%, 4-NOX proportion be 67.36%, 4-NOX/3-NOX.
Embodiment 11
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Sm (OTf) instead
3, through vapor detection, the ratio 1.94 of reaction conversion ratio reaches 87.6%, 3-NOX ratio to be 33.96%, 4-NOX proportion be 66.04%, 4-NOX/3-NOX.
Embodiment 12
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Eu (OTf) instead
3, through vapor detection, the ratio 1.92 of reaction conversion ratio reaches 89.4%, 3-NOX ratio to be 34.19%, 4-NOX proportion be 65.81%, 4-NOX/3-NOX.
Embodiment 13
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Gd (OTf) instead
3, through vapor detection, the ratio 1.94 of reaction conversion ratio reaches 87.1%, 3-NOX ratio to be 34.04%, 4-NOX proportion be 65.96%, 4-NOX/3-NOX.
Embodiment 14
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Tb (OTf) instead
3, through vapor detection, the ratio 2.02 of reaction conversion ratio reaches 90.4%, 3-NOX ratio to be 33.13%, 4-NOX proportion be 66.87%, 4-NOX/3-NOX.
Embodiment 15
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Dy (OTf) instead
3, through vapor detection, the ratio 2.10 of reaction conversion ratio reaches 88.4%, 3-NOX ratio to be 32.31%, 4-NOX proportion be 67.69%, 4-NOX/3-NOX.
Embodiment 16
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Ho (OTf) instead
3, through vapor detection, the ratio 1.95 of reaction conversion ratio reaches 90.9%, 3-NOX ratio to be 33.86%, 4-NOX proportion be 66.14%, 4-NOX/3-NOX.
Embodiment 17
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Er (OTf) instead
3, through vapor detection, the ratio 2.08 of reaction conversion ratio reaches 87.9%, 3-NOX ratio to be 32.45%, 4-NOX proportion be 67.55%, 4-NOX/3-NOX.
Embodiment 18
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Tm (OTf) instead
3, through vapor detection, the ratio 2.13 of reaction conversion ratio reaches 89.2%, 3-NOX ratio to be 31.90%, 4-NOX proportion be 68.10%, 4-NOX/3-NOX.
Embodiment 19
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Yb (OTf) instead
3, through vapor detection, the ratio 2.01 of reaction conversion ratio reaches 86.4%, 3-NOX ratio to be 33.17%, 4-NOX proportion be 66.83%, 4-NOX/3-NOX.
Embodiment 20
Process, with embodiment 1, only changes the kind of metal salts of trifluoromethane sulphonic acid, uses Lu (OTf) instead
3, through vapor detection, the ratio 2.04 of reaction conversion ratio reaches 87.8%, 3-NOX ratio to be 32.86%, 4-NOX proportion be 67.14%, 4-NOX/3-NOX.
After the circulation of trifluoromethanesulfonic acid rare earth metal salt, catalytic performance compares
Repeat the process of embodiment 1, will contain the aqueous phase of nitric acid and metal-salt after separatory, except anhydrating and nitric acid after underpressure distillation, then after carrying out vacuum-drying, regeneration, adds nitric acid again, prepares solution rear feeding secondary response more in molar ratio.
| Sequence number | Transformation efficiency | 4-NOX/3-NOX |
| 1 | 90.2% | 1.99 |
| 2 | 89.3% | 2.01 |
| 3 | 88.8% | 1.97 |
| 4 | 88.4% | 1.97 |
| 5 | 88.2% | 1.98 |
Claims (5)
1. in microreactor, catalytic nitration synthesizes a method for single nitro o-Xylol, it is characterized in that: using trifluoromethanesulfonic acid rare earth metal salt as catalyzer, with o-Xylol, and nitric acid is raw material, in micro passage reaction, carry out nitration reaction with normal pressure; Concrete steps are:
The first step, by nitric acid and the mixing of trifluoromethanesulfonic acid rare earth metal salt, respectively by this mixed solution and o-Xylol respectively via the high pressure constant flow pump of accurate flow control being delivered to two entrances of micro passage reaction;
Second step, two strands of liquid mixes and contacts and after reacting, flow out enter receiving tank from the exit of reactor in micro passage reaction;
3rd step, after completion of the reaction, uses CH
2cl
2extraction, by solution left standstill, reaction system is divided into liquid-liquid diphase, lower floor is the nitration product of o-Xylol, upper strata is the mixture of rare earth metal salt, water, nitric acid, uses separating funnel to be separated two-phase, and lower floor's product obtains single nitro o-Xylol after washing, neutralization, drying; Upper strata containing the aqueous phase of rare earth metal salt after underpressure distillation except anhydrating and nitric acid, then through oven drying, reclaim trifluoromethanesulfonic acid rare earth metal salt.
2. synthesize the method for single nitro o-Xylol according to claim 1, it is characterized in that: micro passage reaction at least has two entrances, an outlet, formed by glass processing, the reactor good corrosion resistance of glass material, inlet microchannel size and microchannel size inconsistent, intake vent size is larger, be conducive to like this improving microring array efficiency, in the microchannel that micro passage reaction has, it contains thousands of cylindricality hybrid channels, large drop can be made to be dispersed into uniform milk sap, enhance mixed effect, be conducive to the carrying out of two phase reaction.
3. synthesize the method for single nitro o-Xylol according to claim 1, it is characterized in that: the volumetric flow rate controlling o-Xylol, nitric acid in the first step, make used molar ratio of material for n(nitric acid): n(o-Xylol)=1.0 ~ 3.0:1, n (o-Xylol): n ([Re (OTf)
3)=5 ~ 20:1.
4. synthesize the method for single nitro o-Xylol according to claim 1, it is characterized in that: in second step, temperature of reaction is 20 DEG C ~ 80 DEG C.
5. synthesize the method for single nitro o-Xylol according to claim 1, it is characterized in that: in second step, the reaction times is 30s ~ 300s.
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Cited By (4)
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| CN106748795A (en) * | 2016-11-18 | 2017-05-31 | 天津市安凯特科技发展有限公司 | A kind of Safe production method of ketone musk |
| CN111362803A (en) * | 2018-12-25 | 2020-07-03 | 南京大学淮安高新技术研究院 | Microchannel reaction process for continuously synthesizing 1-nitro mesitylene |
| CN112851516A (en) * | 2019-11-27 | 2021-05-28 | 西华大学 | Method for nitrifying o-xylene by using microchannel reactor |
| CN117603097A (en) * | 2023-11-29 | 2024-02-27 | 安徽泽升科技股份有限公司 | Method for rapidly preparing 2-bromo-5-nitrobenzenesulfonyl chloride |
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