CN101497552A - Method for preparing p-chlorotoluene and o-chlorotoluene by chlorination toluene - Google Patents
Method for preparing p-chlorotoluene and o-chlorotoluene by chlorination toluene Download PDFInfo
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- CN101497552A CN101497552A CNA2009100303107A CN200910030310A CN101497552A CN 101497552 A CN101497552 A CN 101497552A CN A2009100303107 A CNA2009100303107 A CN A2009100303107A CN 200910030310 A CN200910030310 A CN 200910030310A CN 101497552 A CN101497552 A CN 101497552A
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Abstract
The invention provides a method for preparing p-chlorotoluene and o-chlorotoluene by toluene chlorination. The method comprises the following steps that: after raw material toluene is dried in a drier, the raw material toluene and chlorine are directly chlorinated in the presence of a catalyst so as to obtain mixed chlorotoluene, by-product hydrochloric acid and minor residual; and the mixed chlorotoluene obtained by the chlorination process is used as a raw material to be delivered to a process for separating the mixed chlorotoluene so as to obtain the o-chlorotoluene, the o-chlorotoluene and minor residual liquid through precise fractionating. By the method, a tower type fixed bed circulating chlorination process ensures that gas and liquid are contacted more sufficiently, reaction heat energy can be removed in time, so the reaction effect is better, side products are reduced, and the problem of environmental pollution caused by leakage of chlorine hydride gas in a positive pressure or normal pressure system in the prior absorbing process can be solved. Generation of wastewater is prevented, a rectifying separation mode of two serially connected towers reduces assembly height of the tower and improves separation efficiency, and purities of final products, namely p-chlorotoluene and o-chlorotoluene are both more than or equal to 99.9 percent by weight.
Description
Technical field
The invention belongs to a kind of chlorination toluene and produce the method for parachlorotoluene and ortho-chlorotolu'ene, be specifically related to the method that chlorination toluene is produced mixed-chlorotoluene and high-purity parachlorotoluene of mixed-chlorotoluene separation of produced and ortho-chlorotolu'ene.
Background technology
Parachlorotoluene and ortho-chlorotolu'ene all are very important meticulous Organic Chemicals, the production of intermediates such as multiple in recent years Medicine, agricultural chemicals, dyestuff is starting raw material with them all, these intermediates show very bright development prospect, and the domestic and international market is consistent to be had an optimistic view of.The huge development space in market, downstream stimulates and has promoted the production and the development of toluene(mono)chloride.
The toluene(mono)chloride industrialization is synthetic to mainly contain two kinds of methods, and the one, be the direct chlorination method of raw material with toluene, the 2nd, be the indirect method of raw material with the toluene derivative.The method that with the toluene derivative is raw material is traditional backward technology, be used for perhaps that synthetic toluene direct chlorination is difficult to obtain between the position product.Byproduct is many in traditional toluene(mono)chloride production process, three wastes intractability is big, environmental pollution is serious; The external at present main toluene direct chlorination technology that adopts.Chlorination toluene mainly obtains two kinds of isomer: parachlorotoluene and ortho-chlorotolu'ene, the boiling point of these two kinds of isomer is extremely approaching, can't separate with general ordinary method, so isolation technique is the key of this synthetic technology.
In recent years, the production and the development of China's toluene(mono)chloride had obtained rapid progress, but had also brought problem of environmental pollution simultaneously.21 century is environmental protection century, and the development green chemical industry is the inexorable trend of chemical industry.Improve technology, popularize the key that " cleaning procedure " become China's toluene(mono)chloride product sustainable and stable development and improved the competitiveness.
Summary of the invention
The object of the present invention is to provide a kind of chlorination toluene to produce the cleaning procedure of mixed-chlorotoluene and efficient, energy-conservation, good product quality, free of contamination mixed-chlorotoluene separation method.
Technical scheme of the present invention realizes in the following manner: chlorination toluene prepares the method for parachlorotoluene and ortho-chlorotolu'ene, be raw material toluene advance after the moisture eliminator drying with chlorine under the effect of catalyzer, carry out direct chlorination and obtain mixed-chlorotoluene, by-product hydrochloric acid and a small amount of residue, the mixed-chlorotoluene that chloridization process obtains is delivered to the mixed-chlorotoluene separating technology as secondary raw material, obtains ortho-chlorotolu'ene, parachlorotoluene and a spot of raffinate through precision fractional distillation; It is characterized in that:
1, described direct chlorination method: be to be raw material with toluene, stir in dosing vessel with cocatalyst after the drying device drying, material is squeezed in the chlorination tower, started the chlorination recycle pump, slowly open the chlorine feed under meter, under the effect of catalyzer, carry out chlorination reaction, according to temperature control chlorine flowrate in the reaction tower, the tower temperature control is between 25 ℃-72 ℃, and absolute pressure pressure is 0.06～0.095Mpa, chlorated liquid circulation chlorination, the reaction heat of generation shifts out by water cooler; The hydrogen chloride gas that chlorination produces generates hydrochloric acid by device for absorbing tail gas; After detecting the value of touching the mark, sampling stops chlorination, to the still kettle discharging, 60 ℃-155 ℃ of still kettle still temperature, absolute pressure 0.05～0.085Mpa in the still, chlorated liquid utilizes vacuum take-off and steam heating to carry out aeration in still kettle earlier, removes the dissolved hydrogen chloride gas, and then removes catalyzer through distillation, enter and take off toluene tower, removing the mixture that is mainly contained parachlorotoluene and ortho-chlorotolu'ene behind unreacted toluene and the light constituent is mixed-chlorotoluene.
2, described mixed-chlorotoluene separating technology: be mixed-chlorotoluene to be entered continuously temperature is 70 ℃-130 ℃ in the tower, absolute pressure pressure is the first minute top of tower of 0.003～0.025Mpa, the mixture that cat head is rich in ortho-chlorotolu'ene enters adjacent tower I, the vapour phase of adjacent tower I directly feeds adjacent tower II bottom, temperature is 70 ℃-125 ℃ in the tower of adjacent tower I and adjacent tower II, absolute pressure pressure is 0.008～0.028Mpa, adjacent tower II bottom material pumps into adjacent tower I top by recycle pump, adjacent tower II top obtains its content 〉=99.9%wt of product ortho-chlorotolu'ene, and adjacent tower II tower bottom distillate advances just to divide the tower circulation to separate; Just divide the material that tower bottom is rich in parachlorotoluene to enter top simultaneously to tower II, tower II cat head is obtained light constituent advances just to divide the tower circulation to separate, tower II bottoms material is pumped into the top to tower I by recycle pump, to tower I with to temperature in the tower of tower II is 80 ℃-135 ℃, absolute pressure pressure is 0.005～0.020Mpa, the vapour phase of tower I is directly fed bottom to tower II, tower I bottom is obtained expecting to enter storage tank in the middle of the parachlorotoluene, expecting to pump into the interior temperature of tower in the middle of the parachlorotoluene is 90 ℃-140 ℃, absolute pressure pressure be 0.003～0.015Mpa to smart top of tower continuous rectification, cat head obtains the highly purified parachlorotoluene of content 〉=99.9%wt, is raffinate (many chlorine compounds) at the bottom of the tower.
Technical scheme of the present invention can also further realize by following measure:
Aforesaid chlorination tower is the fixed bed tower reactor, and heap has the catalyzer iron hoop in the bottom.
Aforesaid toluene moisture eliminator is a tower type container, and toluene enters from the bottom, comes out in top, and siccative or salt soluble in water are housed in the tower.
The distillation of aforesaid chlorated liquid adopts the vacuum distilling mode to remove hydrogenchloride and catalyzer, and the mode by heating and negative pressure parses dissolved hydrogenchloride.
Aforesaid chlorine and toluene reaction mol ratio can be from 0.4: 1 to 1: 1, and temperature of reaction is between 25 ℃-72 ℃, and the main component of catalyzer is an iron trichloride, and cocatalyst is sulphur or sulfide, as S
2Cl
2Deng, iron trichloride is generated by chlorine and iron hoop reaction in chlorination process, cocatalyst sulphur or disulphur dichloride (S
2Cl
2) content calculate at 20ppm between the 200ppm according to the toluene consumption.
Aforesaid ortho-chlorotolu'ene tower, parachlorotoluene tower all contain two towers separately, tower I and tower II, and two towers are for being connected in series, tower I has reboiler but does not have overhead condenser, its vapour phase directly feeds the reboiler of the bottom of tower II as tower II, the liquid of tower II bottom pumps into the cat head of tower I with pump, as the backflow of tower I.
The present invention has following advantage:
1, chloridization process adopts tower fixed bed circulation chloridization process, and this has guaranteed that gas-to-liquid contact is more abundant, and reaction heat energy in time shifts out, and reaction effect is better, and by product reduces.
2, the hydrogen chloride gas that produces in the chlorination reaction absorbs by negative pressure falling liquid film circulation and produces hydrochloric acid, not only turn waste into wealth, and consumption reduction synergy, and solved in traditional absorption process that hydrogen chloride gas leaks the problem of environmental pollution that causes in malleation or the normal pressure system.
3, chlorated liquid adopts negative pressure-pumping to remove hydrogenchloride and the vacuum distilling mode is removed catalyzer, has avoided the generation of waste water, does not also have waste discharge.
4, the rectifying separation mode that has adopted two towers to be connected in series respectively to chlorine, adjacent chlorine rectifying tower, this kind mode has reduced the mounting height of tower, improved separation efficiency, the purity of the finished product parachlorotoluene and ortho-chlorotolu'ene all 〉=99.9%wt, and saved investment, reduce working cost, also be convenient to maintenance simultaneously.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Fig. 2 is a direct chlorination method process flow sheet.
Fig. 3 generates parachlorotoluene and ortho-chlorotolu'ene process flow sheet for mixed-chlorotoluene separates.
Among above-mentioned each figure: 1 is moisture eliminator, and 2 is dosing vessel, and 3 are the chlorination tower, 4 is the chlorated liquid water cooler, and 5 is still kettle, and 6 for taking off toluene tower, 7 is condenser, and 8 is water cooler, and 9 is falling-film absorber, 10 is just to divide tower, 11 is just to divide the tower reboiler, and 12 is adjacent tower I, and 13 is adjacent tower I reboiler, 14 is adjacent tower II, 15 is to tower I, and 16 is to tower I reboiler, and 17 is to tower II, 18 is storage tank, 19 is to smart tower, and 20 is to smart tower reboiler, and 21 is the ortho-chlorotolu'ene recycle pump, 22 is the parachlorotoluene recycle pump, and 23 is the parachlorotoluene pump; A is a toluene, and b is a chlorine, and c is a cocatalyst, and d is a mixed-chlorotoluene, and e is a hydrochloric acid, and f is to the column overhead cut, and g is a cut at the bottom of the adjacent Tata, and h is a material in the middle of the parachlorotoluene, and i is to smart tower raffinate (polychloride), and j is an ortho-chlorotolu'ene, and k is a parachlorotoluene, and m is a residue.
Embodiment
Below in conjunction with example and accompanying drawing 1, Fig. 2 and Fig. 3 the present invention is described in further detail:
Know that by Fig. 1 raw material toluene a and chlorine b enter " chlorination toluene technology " to carry out chlorination reaction and obtain mixed-chlorotoluene d, simultaneously by-product hydrochloric acid e and a small amount of residue m.The mixed-chlorotoluene d that chloridization process obtains delivers to " mixed-chlorotoluene separating technology " as raw material, obtains ortho-chlorotolu'ene j through precision fractional distillation, parachlorotoluene k and a spot of raffinate polychloride i.
Being known by Fig. 2, is the chlorination toluene technical process.
Raw material toluene a pumps into moisture eliminator 1 with certain flow, flows to dosing vessel 2.In dosing vessel 2, add a certain amount of catalyzer c and fully stir, material is squeezed in the chlorination tower 3, start the salt acid circulating pump of chlorination recycle pump and device for absorbing tail gas.Slowly open the chlorine feed under meter,, make the tower temperature control between 25 ℃-72 ℃ according to tower interior reaction temperature control chlorine flowrate, chlorated liquid circulation chlorination, the reaction heat of generation shifts out by water cooler 4.The hydrogen chloride gas that chlorination produces generates hydrochloric acid e in the absorption of falling-film absorber 9 internal recycle later by condenser 7, water cooler 8 coolings.Stop chlorination after sampling detects the value of touching the mark, to still kettle 5 dischargings, chlorated liquid utilizes vacuum take-off and steam heating to carry out aeration in still kettle earlier, removes the dissolved hydrogen chloride gas, and then removes catalyzer through distillation.Chlorated liquid removes toluene and light constituent taking off toluene tower 6 after distilling, the mixture that is mainly contained parachlorotoluene and ortho-chlorotolu'ene is mixed-chlorotoluene d.
Know by Fig. 3: be the mixed-chlorotoluene separation process scheme.
Mixed-chlorotoluene d continuously feeding just divides tower 10 tops, and reboiler 11 is arranged at the bottom of the tower, and the component that cat head is rich in ortho-chlorotolu'ene enters adjacent tower I 12.Reboiler 13 is arranged at the bottom of adjacent tower I 12, and its vapour phase directly feeds adjacent tower II 14 bottoms, and adjacent tower II 14 bottoms material pump into adjacent tower I 12 tops by ortho-chlorotolu'ene recycle pump 21.Adjacent tower II 14 tops obtain product ortho-chlorotolu'ene j, and adjacent tower I 12 tower bottom distillate g advance just to divide tower 10 circulations to separate; Just divide the component that tower bottom is rich in parachlorotoluene to enter 17 tops to tower II, cat head obtains light constituent f and advances just to divide tower 10 circulations to separate, and the bottoms material pumps into 15 tops to tower I by parachlorotoluene recycle pump 22, and reboiler 16 is arranged at the bottom of tower I 15.The vapour phase of tower I 15 is directly fed bottom to tower II 17, tower I 15 bottoms are obtained parachlorotoluene in the middle of material enter storage tank 18.Material h in the middle of the chlorine is pumped into smart tower 19 tops, and by tower bottom reboiler 20 and the 23 circulation continuous rectifications of parachlorotoluene pump, cat head obtains highly purified parachlorotoluene k, is raffinate polychloride i at the bottom of the tower.
Embodiment 1:
7.6 tons of toluene a, flow into dosing vessel 2 with 2.5 tons/hour flow drying devices, 1 dry back, add promotor sulphur 1000g, fully stir and pump into chlorination tower 3, chlorine feeds chlorination tower 3 with 0.9 ton/hour flow, the circulation chlorination reaction, chlorine and toluene reaction mole are 1: 1, and temperature of reaction is controlled at 67 ℃, and absolute pressure pressure is 0.07Mpa in the chlorination tower 3, the main component of catalyzer is an iron trichloride, and cocatalyst comprises sulphur or sulfide (S
2Cl
2), iron trichloride is generated by chlorine and iron hoop reaction in chlorination process.Chlorination tower 3 is the fixed bed tower reactor, at tower bottom heap the catalyzer iron hoop is arranged, and chlorine is from the reactor that enters of six different positionss in bottom of tower, chlorated liquid circulation chlorination, and the four-way form is adopted in outlet.Regularly detect the chlorination liquid hold-up, stop chlorination reaction after index reaches, hydrogen chloride gas absorbs by absorption unit, obtains concentration and be 9.5 tons of the hydrochloric acid of 31%wt.Chlorated liquid obtains 10.2 tons of mixed-chlorotoluenes by distillation, piptonychia benzene, get rid of 0.1 ton of residue, take off 0.1 ton of toluene reclaim recycling next time, 150 ℃ of still kettle 5 still temperature, still is pressed and is absolute pressure 0.062Mpa, take off absolute pressure pressure 0.02Mpa in toluene tower 6 towers, tower top temperature rises to 110 ℃ gradually by 85 ℃.
10.2 tons of flow continuously feedings with 1.2 tons/hour of mixed-chlorotoluene just divide tower 10 tops, and the component that cat head is rich in ortho-chlorotolu'ene enters adjacent tower I12, and the component that is rich in parachlorotoluene at the bottom of the tower enters tower II 17.Adjacent tower, tower is all contained two towers separately, and two towers are for being connected in series, tower I has reboiler but does not have overhead condenser, and its vapour phase directly feeds the reboiler of the bottom of tower II as tower II, and the liquid bottom the tower II pumps into cat head to tower I with pump, as the backflow of tower I.
Adjacent tower II 14 tops obtain product ortho-chlorotolu'ene j5.25 ton, and adjacent tower I12 tower bottom distillate g advances just to divide tower 10 circulations to separate; Light constituent f to tower II 17 cats head advances just to divide tower 10 circulations to separate, and the bottoms material pumps into 15 tops to tower I by parachlorotoluene recycle pump 22, and the middle material of the parachlorotoluene h that tower I 15 bottoms are obtained enters storage tank 18.Material h pumps into smart tower 19 top continuous rectifications in the middle of the parachlorotoluene, and cat head obtains highly purified parachlorotoluene k4.85 ton, is 0.1 ton of raffinate i polychloride at the bottom of the tower.
Wherein the processing parameter of each tower is as follows:
| The tower name | Tower internal pressure (absolute pressure) | Tower top temperature |
| Just divide tower | 0.02Mpa | 85℃ |
| The ortho-chlorotolu'ene tower | 0.025Mpa | 87℃ |
| The parachlorotoluene tower | 0.015Mpa | 90℃ |
| To smart tower | 0.01Mpa | 93℃ |
Embodiment 2:
9.5 tons of toluene a, flow into dosing vessel 2 with 2.0 tons/hour flow drying devices, 1 dry back, add promotor sulphur 2000g, fully stir and pump into chlorination tower 3, chlorine adds chlorination tower 3 with 0.5 ton/hour flow, the circulation chlorination reaction, and chlorine b and toluene a reaction mole are 0.8: 1, temperature of reaction is controlled at 32 ℃, and chlorination tower 3 internal pressures are 0.06Mpa (absolute pressure).Regularly detect the chlorination liquid hold-up, stop chlorination reaction after index reaches, hydrogen chloride gas obtains 9.39 tons of the hydrochloric acid that concentration is 31.5%wt by absorption unit.Chlorated liquid obtains 10.22 tons of mixed-chlorotoluenes by distillation, piptonychia benzene, get rid of 0.08 ton of residue, take off 2.0 tons of toluene reclaim recycling next time, 155 ℃ of still kettle 5 still temperature, still is pressed and is absolute pressure 0.065Mpa, take off absolute pressure pressure 0.02Mpa in toluene tower 6 towers, tower top temperature rises to 108 ℃ gradually by 82 ℃.
10.22 tons of flows with 1.3 tons/hour of mixed-chlorotoluene d are continuously pumped into and just divide tower 10, the cat head component enters adjacent tower, and component enters to tower with to smart tower 19 at the bottom of the tower, obtains 4.98 tons of 5.15 tons of ortho-chlorotolu'enes and parachlorotoluenes through separation, discharge 0.09 ton of raffinate, the processing parameter of each tower is as follows:
| The tower name | Tower internal pressure (absolute pressure) | Tower top temperature |
| Just divide tower | 0.021Mpa | 87℃ |
| The ortho-chlorotolu'ene tower | 0.024Mpa | 86℃ |
| The parachlorotoluene tower | 0.014Mpa | 88℃ |
| To smart tower | 0.01Mpa | 92℃ |
Claims (6)
1, chlorination toluene prepares the method for parachlorotoluene and ortho-chlorotolu'ene, be raw material toluene advance after the moisture eliminator drying with chlorine under the effect of catalyzer, carry out direct chlorination and obtain mixed-chlorotoluene, by-product hydrochloric acid and a small amount of residue, the mixed-chlorotoluene that chloridization process obtains is delivered to the mixed-chlorotoluene separating technology as secondary raw material, obtains ortho-chlorotolu'ene, parachlorotoluene and a spot of raffinate through precision fractional distillation; It is characterized in that:
1), described direct chlorination method: be to be raw material with toluene, the dry back of drying device (1) stirs in dosing vessel (2) with cocatalyst, material is squeezed in the chlorination tower (3), started the chlorination recycle pump, slowly open the chlorine feed under meter, under the effect of catalyzer, carry out chlorination reaction, according to temperature control chlorine flowrate in the reaction tower, the tower temperature control is between 25 ℃-72 ℃, and absolute pressure pressure is 0.06～0.095Mpa, chlorated liquid circulation chlorination is shifted out reaction heat by water cooler (4); The hydrogen chloride gas that chlorination produces generates hydrochloric acid by device for absorbing tail gas, after detecting the value of touching the mark, sampling stops chlorination, to still kettle (5) discharging, 60 ℃-155 ℃ of still kettle (5) still temperature, absolute pressure 0.05～0.085Mpa in the still, chlorated liquid utilizes vacuum take-off and steam heating to carry out aeration in still kettle (5) earlier, remove the dissolved hydrogen chloride gas, and then through distillation removal catalyzer, enter and take off toluene tower (6), removing the mixture that is mainly contained parachlorotoluene and ortho-chlorotolu'ene behind unreacted toluene and the light constituent is mixed-chlorotoluene;
2), described mixed-chlorotoluene separating technology: be mixed-chlorotoluene to be entered continuously temperature is 70 ℃-130 ℃ in the tower, absolute pressure pressure is first minute tower (10) top of 0.003～0.025Mpa, the mixture that cat head is rich in ortho-chlorotolu'ene enters adjacent tower I (12), the vapour phase of adjacent tower I (12) directly feeds adjacent tower II (14) bottom, temperature is 70 ℃-125 ℃ in the tower of adjacent tower I (12) and adjacent tower II (14), absolute pressure pressure is 0.008～0.028Mpa, adjacent tower II (14) bottom material pumps into adjacent tower I (12) top by recycle pump, adjacent tower II (14) top obtains its content 〉=99.9%wt of product ortho-chlorotolu'ene, and adjacent tower I (12) tower bottom distillate advances just to divide tower (10) circulation to separate; Just divide the material that parachlorotoluene is rich in tower (10) bottom to enter top simultaneously to tower II (17), tower II tower (17) top is obtained light constituent advances just to divide the tower circulation to separate, tower II (17) bottoms material is pumped into the top to tower I (15) by recycle pump, to tower I (15) with to temperature in the tower of tower II (17) is 80 ℃-135 ℃, absolute pressure pressure is 0.005～0.020Mpa, the vapour phase of tower I (15) is directly fed bottom to tower II (17), tower I (15) bottom is obtained expecting to enter storage tank (18) in the middle of the parachlorotoluene, expecting to pump into the interior temperature of tower in the middle of the parachlorotoluene is 90 ℃-140 ℃, absolute pressure pressure be 0.003～0.015Mpa to smart tower (19) top continuous rectification, cat head obtains the highly purified parachlorotoluene of content 〉=99.9%wt, is raffinate at the bottom of the tower.
2, chlorination toluene according to claim 1 prepares the method for parachlorotoluene and ortho-chlorotolu'ene, it is characterized in that: described chlorination tower (3) is the fixed bed tower reactor, and heap has the catalyzer iron hoop in the bottom.
3, chlorination toluene according to claim 1 prepares the method for parachlorotoluene and ortho-chlorotolu'ene, it is characterized in that: described moisture eliminator (1) is a tower type container, and toluene enters from the bottom, comes out in top, and siccative or salt soluble in water are housed in the tower.
4, chlorination toluene according to claim 1 prepares the method for parachlorotoluene and ortho-chlorotolu'ene, it is characterized in that: the distillation of described chlorated liquid adopts the vacuum distilling mode to remove hydrogenchloride and catalyzer, and the mode by heating and negative pressure parses dissolved hydrogenchloride.
5, chlorination toluene according to claim 1 prepares the method for parachlorotoluene and ortho-chlorotolu'ene, it is characterized in that: described chlorine and toluene reaction mol ratio can be from 0.4: 1 to 1: 1, temperature of reaction is between 25 ℃-72 ℃, the main component of catalyzer is an iron trichloride, and cocatalyst comprises sulphur or sulfide such as S
2Cl
2Deng, iron trichloride is generated by chlorine and iron hoop reaction in chlorination process, and the content of cocatalyst sulphur or disulphur dichloride calculates at 20ppm between the 200ppm according to the toluene consumption.
6, chlorination toluene according to claim 1 prepares the method for parachlorotoluene and ortho-chlorotolu'ene, it is characterized in that: described ortho-chlorotolu'ene tower, parachlorotoluene tower all contain two towers separately, tower I and tower II, and two towers are for being connected in series, tower I has reboiler but does not have overhead condenser, its vapour phase directly feeds the reboiler of the bottom of tower II as tower II, and the liquid of tower II bottom pumps into the cat head of tower I with pump, as the backflow of tower I.
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| CN114436766A (en) * | 2022-02-25 | 2022-05-06 | 常州新东化工发展有限公司 | Method for producing high-purity o-chlorotoluene by adsorption separation method |
| CN114797710A (en) * | 2022-06-06 | 2022-07-29 | 常州新东化工发展有限公司 | Preparation method of chlorotoluene |
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- 2009-03-19 CN CN200910030310A patent/CN100590105C/en not_active Expired - Fee Related
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| CN116143582A (en) * | 2023-04-20 | 2023-05-23 | 山东同成医药股份有限公司 | Preparation method of p-chlorotoluene and o-chlorotoluene |
| CN116143582B (en) * | 2023-04-20 | 2023-07-25 | 山东同成医药股份有限公司 | Preparation method of p-chlorotoluene and o-chlorotoluene |
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