CN101773842A - Supported catalyst and preparation method thereof - Google Patents
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- CN101773842A CN101773842A CN201010034067A CN201010034067A CN101773842A CN 101773842 A CN101773842 A CN 101773842A CN 201010034067 A CN201010034067 A CN 201010034067A CN 201010034067 A CN201010034067 A CN 201010034067A CN 101773842 A CN101773842 A CN 101773842A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention provides a supported catalyst which comprises a carrier and an active component that is supported on the carrier, the carrier is silica, and the active component is at least one of chlorides of transition metals and chlorides of alkaline earth metals. The invention further provides a preparation method of the supported catalyst, which comprises the following steps: (1) water solution of at least one of transition metal salts and alkaline earth metal salts is mixed with silica sol, and then the mixture is dried and roasted, thus preparing a precursor of the catalyst; and (2) the precursor of the catalyst contacts with chlorine, and the contact conditions lead at least part of the transition metals and the alkaline earth metals in the obtained products to exist in the form of chlorides after the contact. The supported catalyst is not easy to be deactivated, the service life is long, the catalyst can be regenerated after deactivation, and the catalytic activity is high, thus improving the efficiency greatly for preparing pyridine polychloride and reducing the production cost.
Description
Technical field
The present invention relates to a kind of loaded catalyst, and this Preparation of catalysts method.
Background technology
4 chloro pyridine is a kind of important organic compound and important synthesis intermediates, can be used for synthetic herbicide, pesticide, bactericide, plant growth regulator and medical pharmacy etc.Penta chloropyridine has higher biologically active; the synthetic intermediate that can be used as agricultural chemicals, medicine and dyestuff; and have characteristics such as wide spectrum, efficient and low toxicity by the synthetic a series of agricultural chemicals of penta chloropyridine, and agricultural development and ecological protection are had great importance, market potential is very wide.
The method of existing preparation 4 chloro pyridine or penta chloropyridine mainly contains pyridine liquid phase chlorination and pyridine gas-solid catalysis chloridising etc.Wherein flow process is simple because of having, yield is high has application prospect most for the gas-solid catalysis chloridising.The pyridine gas-solid catalysis chlorination catalyst of having reported is with muriatic loaded catalysts such as activated carbon loaded cobalt as active component, lanthanums, yet, carbon distribution in use easily takes place and causes the inactivation of catalyst in this catalyst, and, can not regenerate behind this catalysqt deactivation.
Summary of the invention
The present invention is in order to overcome the existing easy inactivation that is used to prepare the catalyst of polychlorinated pyridine such as 4 chloro pyridine, penta chloropyridine, and unrenewable shortcoming behind the inactivation, a kind of new loaded catalyst is provided, this loaded catalyst is difficult for inactivation, service life is longer, can regenerate behind the inactivation, and catalytic activity is very high, thereby has improved the efficient of preparation polychlorinated pyridine greatly and reduced production cost.
Another object of the present invention provides the method for the described loaded catalyst of preparation.
The invention provides a kind of loaded catalyst, this catalyst comprises carrier and loads on active component on the described carrier, and described carrier is a silica, and described active component is at least a in the chloride of the chloride of transition metal and alkaline-earth metal.
The present invention also provides a kind of preparation method of loaded catalyst, and this method may further comprise the steps:
(1) at least a aqueous solution in transition metal salt and the alkali salt is mixed with Ludox, then the gained mixture is carried out drying and roasting, thereby make catalyst precursor;
(2) described catalyst precursor is contacted with chlorine, the condition of described contact makes in the products therefrom of contact back to described transition metal of small part and alkaline-earth metal and exists with its chloride form.
In described catalyst provided by the invention, owing to use silica to substitute existing activated carbon as carrier, thus obviously improved the stability of catalytic activity of described catalyst; And this catalyst is difficult for producing carbon distribution, therefore is not easy inactivation adopting pyridine to prepare in the process of polychlorinated pyridine, and service life is longer; In addition, this catalyst can be handled by aerating oxygen at high temperature after inactivation, activates by feeding chlorine then, thereby is regenerated, and therefore, has improved the utilization rate of catalyst greatly and has reduced the production cost of polychlorinated pyridine.
In addition, the described method preparation technology who prepares catalyst provided by the invention is simple, the process conditions gentleness, thus be easy to realize the described loaded catalyst of preparation.And, according to the record of embodiment as can be seen, adopt the described prepared loaded catalyst of method for preparing catalyst provided by the invention, when being used for the preparation of polychlorinated pyridine such as 4 chloro pyridine, penta chloropyridine, described loaded catalyst has very high catalytic efficiency.
The specific embodiment
Described loaded catalyst provided by the invention comprises carrier and loads on active component on the described carrier, and described carrier is a silica, and described active component is at least a in the chloride of the chloride of transition metal and alkaline-earth metal.
In described catalyst, be benchmark with the gross weight of described catalyst, the content of described active component can be 5-20 weight %, is preferably 7-15 weight %, the content of described carrier can be 80-95 weight %, is preferably 85-93 weight %.Content by making described active component preferably in 7-15 weight %, can guarantee that the catalytic activity of described catalyst is higher on the one hand at 5-20 weight %, thereby guarantees fully to react by the raw material of described catalyst; Can also overcome the higher defective of catalyst cost that causes because of described active component content is excessive on the other hand.Therefore, take all factors into consideration economic factor and catalyst activity, the content of the preferred described activity of such catalysts composition of the present invention is in above-mentioned scope.
In described catalyst, the transition metal that described active component can be used for the method preparing polychlorinated pyridine of various routines or the chloride of alkaline-earth metal, yet, in order further to improve the catalytic activity of described catalyst, and then improving catalytic efficiency in the process of preparation polychlorinated pyridine, described active component is preferably at least a in the chloride of cobalt, lanthanum, barium, iron, copper and zinc.
In a kind of preferred implementation of the present invention, active component in the described catalyst comprises cobalt chloride and lanthanum chloride at least, under this preferable case, can significantly improve the catalytic activity of described catalyst, particularly, the catalytic efficiency at catalyst described in the process of preparation polychlorinated pyridine has improved widely.Further under the preferable case, in described catalyst, be benchmark with the gross weight of described catalyst, the content of described cobalt chloride can be 2-9 weight %, 3-8 weight % more preferably, the content of described lanthanum chloride is 2-12 weight %, more preferably 2.5-10 weight %.
In the present invention, the pore volume of described catalyst can be 0.3-0.4 milliliter/gram catalyst, is preferably 0.35-0.4 milliliter/gram catalyst.Described catalyst in above-mentioned pore volume scope has better catalytic activity, and the life-span of longer use.
In described catalyst, the metallic element in the chloride of described transition metal and alkaline-earth metal can be provided by at least a water soluble salt in nitrate, carbonate, oxalates and the chloride of corresponding metal element; Described silica supports is preferably provided by Ludox.
The preparation method of a kind of loaded catalyst that the present invention also provides, this method may further comprise the steps:
(1) at least a aqueous solution in transition metal salt and the alkali salt is mixed with Ludox, then the gained mixture is carried out drying and roasting, thereby make catalyst precursor;
(2) described catalyst precursor is contacted with chlorine, the condition of described contact makes in the products therefrom of contact back to described transition metal of small part and alkaline-earth metal and exists with its chloride form.
In step (1), the concentration of described solution is different and different with the kind of described transition metal salt and alkali salt, and generally, the concentration of described solution can be the 0.01-0.15 grams per milliliter.
In step (1), what described transition metal salt and alkali salt can be in nitrate, carbonate, oxalates and the chlorides is at least a.
In step (1), what the metallic element in described transition metal salt and the alkali salt can be in cobalt, lanthanum, barium, iron, copper and the zinc is at least a.
In a kind of preferred implementation of the present invention, the metallic element in described transition metal salt and the alkali salt comprises cobalt and lanthanum at least.Under this preferable case, can significantly improve the catalytic activity of described catalyst, particularly, improved widely at the catalytic efficiency of catalyst described in the process of preparation polychlorinated pyridine.
In step (1), there is no particular limitation for concentration of silicon dioxide in the described Ludox, and for the catalyst that guarantees finally to make has advantages of high catalytic activity, concentration of silicon dioxide is preferably 15-30 weight % in the described Ludox.
In step (1), the method that at least a aqueous solution in transition metal salt and the alkali salt is mixed with Ludox can comprise: under 15-40 ℃ temperature, under at the uniform velocity stirring, making the described solution that makes in described Ludox and the step (1) is 1 with weight ratio: 0.1-1.5 mixes, and keep stirring 1-7 hour, thereby make the mixed solution of abundant dispersion.
In step (1), the method of described drying preferably includes described mixed solution is heated to 80-95 ℃, and under this temperature, make water evaporates in the described mixture, water content in mixture is 0.1-15 weight %, be preferably 2-13 weight %, the mixture that obtains was descended dry 12-72 hour at 105-130 ℃.In the present invention, be divided into two stages by dry run with described mixed solution, be lower temperature drying stage (80-95 ℃) and higher temperature drying stage (105-130 ℃), thereby can improve the specific area of the catalyst that finally makes, and then guarantee that the catalyst that finally makes has advantages of high catalytic activity.
In step (1), there is no particular limitation for the condition of described roasting, can suitably select in the roasting condition of routine, and under the preferable case, the condition of described roasting can comprise: temperature is 300-500 ℃, and the time is 5-9 hour.
In step (2), the condition that described catalyst precursor contacts with chlorine can comprise: temperature is 300-400 ℃, is preferably 320-380 ℃, and the time is 2-5 hour, is preferably 2.5-4 hour.
In step (2), described catalyst precursor contacts with chlorine preferably and carries out in the presence of protective gas, and the volume of chlorine accounts for the 30-90% of cumulative volume of the mist of chlorine and described protective gas.In the present invention, described protective gas is meant the gas that can not react with chlorine and described catalyst precursor, and common described protective gas can be a periodic table of elements group 0 element gas for nitrogen and conventional inert gas.
The present invention is further detailed explanation by the following examples.
Embodiment 1
Present embodiment is used to illustrate described loaded catalyst provided by the invention and preparation method thereof.
The cobalt nitrates of 104.2 grams and the lanthanum nitrates of 35.7 grams are dissolved in 2000 milliliters the deionized water, after treating fully dissolving, under room temperature and stirring condition, progressively be added drop-wise in 3.5 kilograms the Ludox of 27 weight %, thereby continue to stir the mixed solution that was fully disperseed in 6 hours after dripping again.Then, under agitation described mixed liquor is warmed up to 90 ℃, and under this temperature, make water evaporates in the described mixed solution, become pasty state (water content is 10 weight %) up to mixture, then the mixture of this pasty state is placed in the drying box 120 ℃ dry 48 hours down.Afterwards, dried mixture is placed in the heating furnace,, thereby obtains catalyst precursor 450 ℃ of following roastings 8 hours.This catalyst precursor is packed in the fixed bed reactors, and the internal diameter of the cylinder of described fixed bed reactors is 32 millimeters, and length is 1200 millimeters.Make described reactor be warming up to 350 ℃ by heating, begin in described reactor to feed the mist (volume of chlorine account for described mist cumulative volume 60%) of chlorine and nitrogen then, described mist fed 4 hours with the flow of 1000 ml/min, thereby made loaded catalyst according to the present invention.CoCl in the described catalyst
2Content be about 7.4 weight %, LaCl
3Content be about 2.7 weight %, and the weight of described catalyst is about 1 kilogram; The pore volume that records described catalyst by nitrogen adsorption desorption method is 0.36 a milliliter/gram catalyst.
With nitrogen is carrier, with the pyridine vaporization, simultaneously chlorine is preheated to the temperature identical with pyridine, and described pyridine is mixed in premixed device with 1: 10 volume ratio with chlorine; With the adjustment to 330 of the above-mentioned described fixed bed reactors that described catalyst is housed ℃, and make from the mist in the described premixed device with 110h
-1Flow feed in the described fixed bed reactors.Feed in the described fixed bed reactors after 24 hours, 100 hours and 500 hours at described mist respectively, the product analysis that makes after adopting high performance liquid chromatography to reaction learns that the content of 4 chloro pyridine and penta chloropyridine is as shown in table 1 in the conversion ratio of pyridine and the product.
Embodiment 2
Present embodiment is used to illustrate described loaded catalyst provided by the invention and preparation method thereof.
The cobalt nitrates of 104.2 grams, the lanthanum nitrates of 35.7 grams and the barium chlorides of 30 grams are dissolved in 2000 milliliters the deionized water, after treating fully dissolving, under room temperature and stirring condition, progressively be added drop-wise in 3.5 kilograms the Ludox of 27 weight %, thereby continue to stir the mixed solution that was fully disperseed in 6 hours after dripping again.Then, under agitation described mixed liquor is warmed up to 95 ℃, and under this temperature, make water evaporates in the described mixed solution, become pasty state (water content is 5 weight %) up to mixture, then the mixture of this pasty state is placed in the drying box 135 ℃ dry 24 hours down.Afterwards, dried mixture is placed in the heating furnace,, thereby obtains catalyst precursor 500 ℃ of following roastings 5 hours.This catalyst precursor is packed in the fixed bed reactors, and the internal diameter of the cylinder of described fixed bed reactors is 32 millimeters, and length is 1200 millimeters.Make described reactor be warming up to 400 ℃ by heating, begin in described reactor to feed the mist (volume of chlorine account for described mist cumulative volume 60%) of chlorine and nitrogen then, described mist fed 4 hours with the flow of 1000 ml/min, thereby made loaded catalyst according to the present invention.CoCl in the described catalyst
2Content be about 7.4 weight %, LaCl
3Content be about 2.7 weight %, BaCl
2Content be about 0.3 weight %, and the weight of described catalyst is about 1 kilogram; The pore volume that records described catalyst by nitrogen adsorption desorption method is 0.37 a milliliter/gram catalyst.
Method according to embodiment 1 reacts with the preparation polychlorinated pyridine pyridine and chlorine.Feed in the described fixed bed reactors after 24 hours, 100 hours and 500 hours at described mist respectively, the product analysis that makes after adopting high performance liquid chromatography to reaction learns that the content of 4 chloro pyridine and penta chloropyridine is as shown in table 1 in the conversion ratio of pyridine and the product.
Embodiment 3
Present embodiment is used to illustrate described loaded catalyst provided by the invention and preparation method thereof.
The cobalt nitrates of 35.2 grams, the lanthanum nitrates of 26.5 grams, the barium nitrates of 59 grams and the zinc nitrates of 19 grams are dissolved in 2000 milliliters the deionized water, after treating fully dissolving, under room temperature and stirring condition, progressively be added drop-wise in 3.5 kilograms the Ludox of 27 weight %, thereby continue to stir the mixed solution that was fully disperseed in 6 hours after dripping again.Then, under agitation described mixed liquor is warmed up to 80 ℃, and under this temperature, make water evaporates in the described mixed solution, become pasty state (water content is 13 weight %) up to mixture, then the mixture of this pasty state is placed in the drying box 110 ℃ dry 72 hours down.Afterwards, dried mixture is placed in the heating furnace,, thereby obtains catalyst precursor 300 ℃ of following roastings 9 hours.This catalyst precursor is packed in the fixed bed reactors, and the internal diameter of the cylinder of described fixed bed reactors is 32 millimeters, and length is 1200 millimeters.Make described reactor be warming up to 300 ℃ by heating, begin in described reactor to feed the mist (volume of chlorine account for described mist cumulative volume 60%) of chlorine and nitrogen then, described mist fed 4 hours with the flow of 1000 ml/min, thereby made loaded catalyst according to the present invention.CoCl in the described catalyst
2Content be about 2.5 weight %, LaCl
3Content be about 2.0 weight %, BaCl
2Content be about 5.9 weight %, ZnCl
2Content be about 1.9 weight %, and the weight of described catalyst is about 1 kilogram; The pore volume that records described catalyst by nitrogen adsorption desorption method is 0.39 a milliliter/gram catalyst.
Method according to embodiment 1 reacts with the preparation polychlorinated pyridine pyridine and chlorine.Feed in the described fixed bed reactors after 24 hours, 100 hours and 500 hours at described mist respectively, the product analysis that makes after adopting high performance liquid chromatography to reaction learns that the content of 4 chloro pyridine and penta chloropyridine is as shown in table 1 in the conversion ratio of pyridine and the product.
Embodiment 4
Present embodiment is used to illustrate described loaded catalyst provided by the invention and preparation method thereof.
Method according to embodiment 1 prepares described catalyst and pyridine and chlorine is reacted, different is, in the process of the described catalyst of preparation, replace the cobalt nitrate of 104.2 grams with the ferric oxalate of 145.7 grams, thereby contain the FeCl of the 7.4 weight % that have an appointment in the catalyst that makes
3LaCl with about 2.7 weight %
3In addition, feed in the described fixed bed reactors after 24 hours, 100 hours and 500 hours at described mist respectively, the product analysis that makes after adopting high performance liquid chromatography to reaction learns that the content of 4 chloro pyridine and penta chloropyridine is as shown in table 1 in the conversion ratio of pyridine and the product.
Embodiment 5
Present embodiment is used to illustrate described loaded catalyst provided by the invention and preparation method thereof.
Method according to embodiment 1 prepares described catalyst and pyridine and chlorine is reacted, different is that in the process of the described catalyst of preparation, the consumption of cobalt nitrate is 21.1 grams, the consumption of lanthanum nitrate is 35.7 grams, thereby contains the CoCl of the 1.5 weight % that have an appointment in the catalyst that makes
2LaCl with about 2.7 weight %
3In addition, feed in the described fixed bed reactors after 24 hours, 100 hours and 500 hours at described mist respectively, the product analysis that makes after adopting high performance liquid chromatography to reaction learns that the content of 4 chloro pyridine and penta chloropyridine is as shown in table 1 in the conversion ratio of pyridine and the product.
Embodiment 6
Present embodiment is used to illustrate described loaded catalyst provided by the invention and preparation method thereof.
Method according to embodiment 1 prepares described catalyst and pyridine and chlorine is reacted, different is, by sintering temperature being controlled to be 380 ℃, roasting time is controlled to be 4.5 hours, is 0.45 milliliter/gram catalyst thereby make the pore volume of the catalyst that finally makes.In addition, feed in the described fixed bed reactors after 24 hours, 100 hours and 500 hours at described mist respectively, the product analysis that makes after adopting high performance liquid chromatography to reaction learns that the content of 4 chloro pyridine and penta chloropyridine is as shown in table 1 in the conversion ratio of pyridine and the product.
Embodiment 7
Present embodiment is used to illustrate described loaded catalyst provided by the invention and preparation method thereof.
Method according to embodiment 3 prepares described catalyst and pyridine and chlorine is reacted, different is, in the process of the described catalyst of preparation, do not use zinc nitrate, and the consumption of cobalt nitrate is 35.2 grams, the consumption of lanthanum nitrate is 21.2 grams, and the consumption of barium nitrate is 74.0 grams, thereby contains the CoCl of the 2.5 weight % that have an appointment in the catalyst that makes
2, about 1.6 weight % LaCl
3BaCl with about 5.9 weight %
2In addition, feed in the described fixed bed reactors after 24 hours, 100 hours and 500 hours at described mist respectively, the product analysis that makes after adopting high performance liquid chromatography to reaction learns that the content of 4 chloro pyridine and penta chloropyridine is as shown in table 1 in the conversion ratio of pyridine and the product.
Comparative Examples 1
Preparation contains 74 gram CoCl
2With 27 gram LaCl
3Mixed solution, the activated carbon that under agitation with 899 average particulate diameters that restrain is 0.7 millimeter then is added in the described mixed solution, after activated carbon all is added in the described mixed solution, continue again to stir 4 hours, then 85 ℃ dry 24 hours down, thereby obtain 1 kilogram catalyst.
This catalyst is filled in the fixed bed reactors, and the internal diameter of the cylinder of described fixed bed reactors is 32 millimeters, and length is 1200 millimeters.
Then, the method according to embodiment 1 reacts pyridine and chlorine.Feed in the described fixed bed reactors after 24 hours, 100 hours and 500 hours at described mist respectively, the product analysis that makes after adopting high performance liquid chromatography to reaction learns that the content of 4 chloro pyridine and penta chloropyridine is as shown in table 1 in the conversion ratio of pyridine and the product.
Table 1
As can be seen from Table 1, adopt service life of the prepared loaded catalyst of preparation method of loaded catalyst provided by the invention longer, have very high catalytic activity, and can generate 4 chloro pyridine and/or penta chloropyridine with higher selectivity catalysis pyridine and chlorine reaction.In addition, in described loaded catalyst, contain cobalt chloride and lanthanum chloride at least, and the content of cobalt chloride is 2-9 weight %, when the content of lanthanum chloride is 2-12 weight %, make that the content of 4 chloro pyridine in the product that pyridine and chlorine reaction generate and/or penta chloropyridine is relative higher, thereby show better catalytic activity.
Claims (11)
1. a loaded catalyst is characterized in that, this catalyst comprises carrier and load on active component on the described carrier, and described carrier is a silica, and described active component is at least a in the chloride of the chloride of transition metal and alkaline-earth metal.
2. catalyst according to claim 1 wherein, in described catalyst, is a benchmark with the gross weight of described catalyst, and the content of described active component is 5-20 weight %, and the content of described carrier is 80-95 weight %.
3. catalyst according to claim 1, wherein, described active component is at least a in the chloride of cobalt, lanthanum, barium, iron, copper and zinc.
4. according to any described catalyst among the claim 1-3, wherein, at least comprise cobalt chloride and lanthanum chloride in the described active component, and in described catalyst, gross weight with described catalyst is a benchmark, the content of described cobalt chloride is 2-9 weight %, and the content of described lanthanum chloride is 2-12 weight %.
5. catalyst according to claim 1, wherein, the pore volume of described catalyst is 0.3-0.4 milliliter/gram catalyst.
6. the preparation method of a loaded catalyst is characterized in that, this method may further comprise the steps:
(1) at least a aqueous solution in transition metal salt and the alkali salt is mixed with Ludox, then the gained mixture is carried out drying and roasting, thereby make catalyst precursor;
(2) described catalyst precursor is contacted with chlorine, the condition of described contact makes in the products therefrom of contact back to described transition metal of small part and alkaline-earth metal and exists with its chloride form.
7. method according to claim 6, wherein, in step (1), the method of described drying comprises described mixed solution is heated to 80-95 ℃, and under this temperature, make water evaporates in the described mixture, water content in mixture is 0.1-15 weight %, and the mixture that obtains was descended dry 12-72 hour at 105-130 ℃.
8. method according to claim 6, wherein, in step (1), the condition of described roasting comprises: temperature is 300-500 ℃, the time is 5-9 hour.
9. method according to claim 6, wherein, in step (1), described transition metal salt and alkali salt are at least a in nitrate, carbonate, oxalates and the chloride.
10. method according to claim 6, wherein, in step (2), the condition that described catalyst precursor contacts with chlorine comprises: temperature is 300-400 ℃, the time is 2-5 hour.
11. according to claim 6 or 10 described methods, wherein, in step (2), described catalyst precursor contacts in the presence of protective gas with chlorine and carries out, the volume of chlorine accounts for the 30-90% of cumulative volume of the mist of chlorine and described protective gas.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108409644A (en) * | 2018-05-10 | 2018-08-17 | 四川福思达生物技术开发有限责任公司 | A kind of preparation method of penta chloropyridine |
| CN113244934A (en) * | 2021-05-25 | 2021-08-13 | 上海华谊（集团）公司 | Catalyst for producing 2,3, 6-trichloropyridine and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1657164A (en) * | 2004-12-22 | 2005-08-24 | 东南大学 | Catalyst for preparing penta chloropyridine and its preparation method |
| CN100348319C (en) * | 2005-10-31 | 2007-11-14 | 东南大学 | Catalyst for gas-solid phase synthesis of 2-chloro-5-trichloro methyl pyridine and its prepn |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108409644A (en) * | 2018-05-10 | 2018-08-17 | 四川福思达生物技术开发有限责任公司 | A kind of preparation method of penta chloropyridine |
| CN108409644B (en) * | 2018-05-10 | 2021-03-05 | 四川福思达生物技术开发有限责任公司 | Preparation method of pentachloropyridine |
| CN113244934A (en) * | 2021-05-25 | 2021-08-13 | 上海华谊（集团）公司 | Catalyst for producing 2,3, 6-trichloropyridine and preparation method thereof |
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Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant after: Nutrichem Co., Ltd. Address before: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant before: Nutrichem International Co., Ltd. Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant after: Nutrichem Co., Ltd. Address before: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant before: Nutrichem International Co., Ltd. |
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Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Patentee after: BEIJING NUTRICHEM COMPANY LIMITED Address before: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Patentee before: Nutrichem Co., Ltd. Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Patentee after: BEIJING NUTRICHEM COMPANY LIMITED Address before: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Patentee before: Nutrichem Co., Ltd. |
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