CN109126839A - A kind of composite catalyst composition and the method for preparing 2,4-/3,4- dichlorotoleune - Google Patents
A kind of composite catalyst composition and the method for preparing 2,4-/3,4- dichlorotoleune Download PDFInfo
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- CN109126839A CN109126839A CN201811019820.XA CN201811019820A CN109126839A CN 109126839 A CN109126839 A CN 109126839A CN 201811019820 A CN201811019820 A CN 201811019820A CN 109126839 A CN109126839 A CN 109126839A
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- 239000002131 composite material Substances 0.000 title claims abstract description 33
- 239000003054 catalyst Substances 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 10
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000005864 Sulphur Substances 0.000 claims abstract description 11
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims abstract description 11
- 239000000843 powder Substances 0.000 claims abstract description 11
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 21
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 15
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical class Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 238000005660 chlorination reaction Methods 0.000 abstract description 13
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract description 6
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 abstract description 2
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical class ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GSSJSUKUYXXPME-UHFFFAOYSA-N benzene;chloromethane Chemical compound ClC.C1=CC=CC=C1 GSSJSUKUYXXPME-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/135—Halogens; Compounds thereof with titanium, zirconium, hafnium, germanium, tin or lead
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of composite catalyst composition and utilizes composite catalyst composition preparation 2,4-/3, the method of 4- dichlorotoleune, composite catalyst composition provided by the invention are made of the mixing of antimony trichloride, titanium tetrachloride, Nickel Chloride, ferric trichloride, alchlor and sulphur powder；2,4-/3,4- dichlorotoleune are prepared using composite catalyst composition catalysis p-chlorotoluene chlorination of the invention, selectivity with higher increases the content of 3,4- dichlorotoleune, adapted to the demand in market；Meanwhile unreacted p-chlorotoluene can still participate in subsequent 2,4-/3, in the preparation of 4- dichlorotoleune, meet the theory of Green Chemistry.
Description
Technical field
The present invention relates to one kind 2,4-/3, the preparation method of 4- dichlorotoleune, in particular to a kind of composite catalyst combinations
Object and preparation method thereof, and 2,4-/3,4- bis- are generated using composite catalyst composition catalysis p-chlorotoluene chlorination reaction
The method of chlorotoluene.
Background technique
2,4-DCT, 3,4- dichlorotoleune are all important industrial chemicals, are mainly used for organic synthesis, medicine and dye
Material industry, can also be used as organic solvent.Currently, industrially generalling use p-chlorotoluene chlorination gas chlorination synthesis 2,4- bis-
Chlorotoluene simultaneously has a small amount of dichlorotoluene isomers to generate (mainly 3,4- dichlorotoleune), then passes through rectification process
2,4-/3,4- dichlorotoleune is separated.
In recent years, more is gradually industrially become to the application of 3,4- dichlorotoleune, and the demand of 2,4-DCT is corresponding
Become smaller.So, just it is badly in need of increasing ratio of 3, the 4- dichlorotoleune in chlorated liquid to solve the problems, such as this.
Summary of the invention
To solve the above-mentioned problems, the invention discloses a kind of composite catalyst compositions and preparation method thereof, and use
Composite catalyst composition catalysis reduction preparation 2,4-/3,4- dichlorotoleune, and 3 are improved, the content of 4- dichlorotoleune.
" more chlorotoluenes " of the present invention refers to containing chlorotoluene compounds more than three chlorine.
In order to reach the goals above, the invention provides the following technical scheme:
A kind of composite catalyst composition and preparation 2,4-/3, the method for 4- dichlorotoleune, comprising the following steps:
(1) preparation of composite catalyst composition: 10 ~ 20 parts of antimony trichlorides, 10 ~ 20 parts of titanium tetrachlorides, 10 ~ 20 parts
Nickel Chloride, 30 ~ 40 parts of ferric trichlorides, 20 parts of alchlors and 10 ~ 20 parts of sulphur powders are uniformly mixed, and are carried out to mixed component
It is dried, water content is lower than 1 wt%；
(2) chlorination reaction of p-chlorotoluene: being added p-chlorotoluene in a kettle, is added again after opening stirring into reaction kettle
Carbon monoxide-olefin polymeric is closed, after carbon monoxide-olefin polymeric to be composite is evenly distributed in material, is slowly introducing chlorine, reaction temperature control
Between 35 ~ 55 DEG C, when the content of more chlorotoluenes increases to 3 ~ 5 wt% in chlorated liquid, stop logical chlorine；Reaction end gas is used
Water absorbs, and byproduct hydrochloric acid is made；
(3) component separates: reaction product chlorated liquid being separated by rectifying column, first separates unreacted raw material to chloromethane
Benzene, the tower bottom recombination lease making rectifying column that then rectifying goes out isolate 2,4-DCT and 3,4- dichlorotoleune.
Preferably, the composite catalyst composition composition being added in the step (1) are as follows: 10 ~ 20 parts of tri-chlorinations
Antimony, 10 ~ 20 parts of titanium tetrachlorides, 10 ~ 20 parts of Nickel Chlorides, 30 ~ 40 parts of ferric trichlorides, 20 parts of alchlors, 10 ~ 20
Part sulphur powder.
Preferably, the quality that composite catalyst composition is added in the step 2 is p-chlorotoluene material quality
0.1%.
Preferably, reaction kettle size is 10000 L in the step 2, leading to chlorine speed is 50 m3/h。
Beneficial effect
The present invention is prepared for a kind of composite catalyst composition, is prepared for 2,4-/3,4- dichloro by chlorination, catalytic reduction reaction
Toluene, and 3 are increased, the content of 4- dichlorotoleune has adapted to the needs in market；P-chlorotoluene unreacted is complete, reduces pair
The generation of the more chlorine impurity of product；Meanwhile unreacted p-chlorotoluene can still participate in subsequent 2,4-/3,4- dichlorotoleune
In preparation, meet the theory of Green Chemistry.
Specific embodiment
The present invention is described in further detail combined with specific embodiments below, but embodiments of the present invention are only used
In illustrating the present invention, rather than limit the scope of the invention.
Embodiment 1
(1) preparation of composite catalyst composition: 20 kg antimony trichlorides, 10 kg titanium tetrachlorides, 10 kg Nickel Chlorides, 30 kg
Ferric trichloride, 20 kg alchlors, 10 kg sulphur powders are uniformly mixed, and to being dried under mixed component vacuum state,
Water content is lower than 1 wt%.
(2) chlorination reaction of p-chlorotoluene: being added 7500 kg p-chlorotoluenes in 10000 L reaction kettles, after opening stirring
7.5 kg composite catalyst compositions are added into reaction kettle, are slowly introducing chlorine, lead to 50 m of chlorine speed3/ h, temperature control exist
Between 35 ~ 55 DEG C, every two hours sampling analyses, until the content of more chlorotoluenes increases to 3 ~ 5 wt% in chlorated liquid
When, stop logical chlorine.Reaction end gas is absorbed with water, and byproduct hydrochloric acid is made.
(3) component separates: reaction product chlorated liquid being separated by rectifying column, first separates unreacted raw material pair
3900 kg of chlorotoluene, purity 99%；Then the tower bottom heavy constituent that rectifying goes out is isolated into 2,4 di chloro toluene by rectifying column
3340 kg, purity 99.5%, 3,763 kg of 4- dichlorotoleune, purity 99.5%, extra about 477 kg of other useless components.
Through chromatographic, the mass content of each component in the chlorated liquid isolated are as follows: p-chlorotoluene 52%, 2,4-
Dichlorotoleune 35%, 3,4- dichlorotoleune 8%, other 5%.
Embodiment 2
(1) preparation of composite catalyst composition: 10 kg antimony trichlorides, 20 kg titanium tetrachlorides, 10 kg Nickel Chlorides, 30 kg
Ferric trichloride, 20 kg alchlors, 10 kg sulphur powders are uniformly mixed, and carry out vacuum drying treatment, water content to mixed component
Lower than 1 wt%.
(2) chlorination reaction of p-chlorotoluene: being added 7500 kg p-chlorotoluenes in 10000 L reaction kettles, after opening stirring
7.5 kg composite catalyst compositions are added into reaction kettle, are slowly introducing chlorine, lead to 50 m of chlorine speed3/ h, temperature control exist
Between 35 ~ 55 DEG C, every two hours sampling analyses, until the content of more chlorotoluenes increases to 3 ~ 5 wt% in chlorated liquid
When, stop logical chlorine.Reaction end gas is absorbed with water, and byproduct hydrochloric acid is made.
(3) component separates: reaction product chlorated liquid being separated by rectifying column, first isolates unreacted raw material pair
4275 kg of chlorotoluene, purity 99%；Then the tower bottom heavy constituent that rectifying goes out is isolated into 2,4 di chloro toluene by rectifying column
3054 kg, purity 99.5%, 3,572 kg of 4- dichlorotoleune, purity 99.5%, about 477 kg of other components.
Through chromatographic, the mass content of each component in chlorated liquid are as follows: p-chlorotoluene 57%, 2,4-DCT
32%, 3,4- dichlorotoleune 6%, other 5%.
Embodiment 3
(1) preparation of composite catalyst composition: 10 kg antimony trichlorides, 10 kg titanium tetrachlorides, 20 kg Nickel Chlorides, 30 kg
Ferric trichloride, 20 kg alchlors, 10 kg sulphur powders are uniformly mixed, and carry out vacuum drying treatment, water content to mixed component
Lower than 1 wt%.
(2) chlorination reaction of p-chlorotoluene: being added 7500 kg p-chlorotoluenes in 10000 L reaction kettles, after opening stirring
7.5 kg composite catalyst compositions are added into reaction kettle, are slowly introducing chlorine, lead to 50 m of chlorine speed3/ h, temperature control exist
Between 35 ~ 55 DEG C, every two hours sampling analyses, until the content of more chlorotoluenes increases to 3 ~ 5 wt% in chlorated liquid
When, stop logical chlorine.Reaction end gas is absorbed with water, and byproduct hydrochloric acid is made.
(3) component separates: reaction product chlorated liquid being separated by rectifying column, first separates unreacted raw material pair
4725 kg of chlorotoluene, purity 99%；Then the tower bottom heavy constituent that rectifying goes out is isolated into 2,4- dichlorotoleune by rectifying column
2386 kg, purity 99.5%, 3,668 kg of 4- dichlorotoleune, purity 99.5%, about 477 kg of other components.
Through chromatographic, the mass content of each component in chlorated liquid are as follows: p-chlorotoluene 63%, 2,4-DCT
25%, 3,4- dichlorotoleune 7%, other 5%.
Embodiment 4
(1) preparation of composite catalyst composition: 10 kg antimony trichlorides, 10 kg titanium tetrachlorides, 10 kg Nickel Chlorides, 30 kg
Ferric trichloride, 20 kg alchlors, 20 kg sulphur powders are uniformly mixed, and carry out vacuum drying treatment, water content to mixed component
Lower than 1 wt%.
(2) chlorination reaction of p-chlorotoluene: being added 7500 kg p-chlorotoluenes in 10000 L reaction kettles, after opening stirring
7.5 kg composite catalyst compositions are added into reaction kettle, are slowly introducing chlorine, lead to 50 m of chlorine speed3/ h, temperature control exist
Between 35 ~ 55 DEG C, every two hours sampling analyses, until the content of more chlorotoluenes increases to 3 ~ 5 wt% in chlorated liquid
When, stop logical chlorine.Reaction end gas is absorbed with water, and byproduct hydrochloric acid is made.
(3) component separates: reaction product chlorated liquid being separated by rectifying column, first separates unreacted raw material pair
4425 kg of chlorotoluene, purity 99%；Then the tower bottom heavy constituent that rectifying goes out is isolated into 2,4 di chloro toluene by rectifying column
2863 kg, purity 99.5%, 3,572 kg of 4- dichlorotoleune, purity 99.5%, about 477 kg of other components.
Through chromatographic, the mass content of each component in chlorated liquid are as follows: p-chlorotoluene 59%, 2,4-DCT
30%, 3,4- dichlorotoleune 6%, other 5%.
Embodiment 5
(1) preparation of composite catalyst composition: 10 kg antimony trichlorides, 10 kg titanium tetrachlorides, 10 kg Nickel Chlorides, 40 kg
Ferric trichloride, 20 kg alchlors, 10 kg sulphur powders are uniformly mixed, and carry out vacuum drying treatment, water content to mixed component
Lower than 1 wt%.
(2) chlorination reaction of p-chlorotoluene: being added 7500 kg p-chlorotoluenes in 10000 L reaction kettles, after opening stirring
7.5 kg composite catalyst compositions are added into reaction kettle, are slowly introducing chlorine, lead to 50 m of chlorine speed3/ h, temperature control exist
Between 35 ~ 55 DEG C, every two hours sampling analyses, until the content of more chlorotoluenes increases to 3 ~ 5 wt% in chlorated liquid
When, stop logical chlorine.Reaction end gas is absorbed with water, and byproduct hydrochloric acid is made.
(3) component separates: reaction product chlorated liquid being separated by rectifying column, first separates unreacted raw material pair
4125 kg of chlorotoluene, purity 99%；Then the tower bottom heavy constituent that rectifying goes out is isolated into 2,4 di chloro toluene by rectifying column
2454 kg, purity 99.5%, 3,1402 kg of 4- dichlorotoleune, purity 99.5%, about 438 kg of other components.
Through chromatographic, the mass content of each component in chlorated liquid are as follows: p-chlorotoluene 55%, 2,4-DCT
28%, 3,4- dichlorotoleune 16%, other 5%.
As can be seen from the above embodiments, when the preparation of composite catalyst are as follows: 10 kg antimony trichlorides, 10 kg, tetra- chlorination
When titanium, 10 kg Nickel Chlorides, 40 kg ferric trichlorides, 20 kg alchlors, 10 kg sulphur powder, conversion efficiency is highest,
The ratio of obtained 3,4- dichlorotoleune is maximum.
By efficiently separating for rectifying column, the purity of 2,4-/3,4- dichlorotoleune can reach 99.5% or more.
Claims (6)
1. a kind of composite catalyst composition, which is characterized in that include following composition: 10 ~ 20 parts of antimony trichlorides, 10 ~ 20
Part titanium tetrachloride, 10 ~ 20 parts of Nickel Chlorides, 30 ~ 40 parts of ferric trichlorides, 20 parts of alchlors, 10 ~ 20 parts of sulphur powders.
2. composite catalyst composition as described in claim 1, which is characterized in that 10 parts of antimony trichlorides, 10 parts of titanium tetrachlorides,
10 parts of Nickel Chlorides, 40 parts of ferric trichlorides, 20 parts of alchlors, 10 parts of sulphur powders.
3. composite catalyst composition as described in claim 1, which is characterized in that water content is lower than 1 wt% after dry.
4. a kind of prepare 2,4-/3, the method for 4- dichlorotoleune, feature with composite catalyst composition described in claim 1
It is, comprising the following steps:
(1) p-chlorotoluene is added in a kettle, composite catalyst composition is added into reaction kettle after opening stirring, it is to be mixed
After uniformly, it is slowly introducing chlorine, reaction temperature controls between 35 ~ 55 DEG C, until the content of more chlorotoluenes increases in chlorated liquid
When to 3 ~ 5 wt%, stops logical chlorine, obtain chlorated liquid；
(2) component separates: reaction product chlorated liquid being separated by rectifying column, first separates unreacted raw material to chloromethane
Then the tower bottom heavy constituent that rectifying goes out is isolated 2,4-DCT and 3,4- dichlorotoleune by rectifying column by benzene.
5. preparation 2,4-/3 as claimed in claim 4, the method for 4- dichlorotoleune, which is characterized in that in step (1), be added
The quality of composite catalyst composition is the 0.1% of p-chlorotoluene material quality.
6. preparation 2,4-/3 as claimed in claim 4, the method for 4- dichlorotoleune, which is characterized in that in step (1), reaction
Kettle size is 10000 L, leads to 50 m of chlorine speed3/h。
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107413377A (en) * | 2017-05-23 | 2017-12-01 | 中触媒新材料股份有限公司 | A kind of 2,5 dichlorotoleune isomerization catalysts and its preparation method and application |
| CN114773146A (en) * | 2022-05-19 | 2022-07-22 | 常州新东化工发展有限公司 | Method for synthesizing 2,4-dichlorotoluene and 3,4-dichlorotoluene by directional chlorination of p-chlorotoluene with a supported catalyst |
| CN115850195A (en) * | 2022-11-29 | 2023-03-28 | 宁夏格瑞精细化工有限公司 | Synthetic method of sulfentrazone intermediate |
| CN116063144A (en) * | 2022-12-29 | 2023-05-05 | 柳州东风容泰化工股份有限公司 | A kind of method of producing 2,4-dichlorotoluene |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6156945A (en) * | 1998-11-17 | 2000-12-05 | Occidental Chemical Corporation | Method of making high purity 2,4- and 3,4-dichlorotoluene |
| US6222079B1 (en) * | 1999-10-28 | 2001-04-24 | Occidental Chemical Corporation | Method of increasing certain isomeric ratios in chlorinating substituted benzenes |
| CN1546443A (en) * | 2003-12-11 | 2004-11-17 | 株洲化工集团诚信有限公司 | Method for preparing 2,4-toluene dichloride |
| CN102584522A (en) * | 2012-02-21 | 2012-07-18 | 南通市东昌化工有限公司 | Production method of 2,4-dichlorotoluene |
| CN105237330A (en) * | 2015-11-18 | 2016-01-13 | 江苏联化科技有限公司 | Synthesizing method for 2,3,6-trichlorobenzoic acid and intermediate of 2,3,6-trichlorobenzoic acid |
| CN106242940A (en) * | 2016-08-01 | 2016-12-21 | 南京钟腾化工有限公司 | A kind of synthesis technique of 2,4 dichlorotoleune |
-
2018
- 2018-09-03 CN CN201811019820.XA patent/CN109126839A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6156945A (en) * | 1998-11-17 | 2000-12-05 | Occidental Chemical Corporation | Method of making high purity 2,4- and 3,4-dichlorotoluene |
| US6222079B1 (en) * | 1999-10-28 | 2001-04-24 | Occidental Chemical Corporation | Method of increasing certain isomeric ratios in chlorinating substituted benzenes |
| CN1546443A (en) * | 2003-12-11 | 2004-11-17 | 株洲化工集团诚信有限公司 | Method for preparing 2,4-toluene dichloride |
| CN102584522A (en) * | 2012-02-21 | 2012-07-18 | 南通市东昌化工有限公司 | Production method of 2,4-dichlorotoluene |
| CN105237330A (en) * | 2015-11-18 | 2016-01-13 | 江苏联化科技有限公司 | Synthesizing method for 2,3,6-trichlorobenzoic acid and intermediate of 2,3,6-trichlorobenzoic acid |
| CN106242940A (en) * | 2016-08-01 | 2016-12-21 | 南京钟腾化工有限公司 | A kind of synthesis technique of 2,4 dichlorotoleune |
Non-Patent Citations (1)
| Title |
|---|
| 朱旭容，等: "对氯甲苯氯化制2,4-二氯甲苯", 《南京化工学院学报》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107413377A (en) * | 2017-05-23 | 2017-12-01 | 中触媒新材料股份有限公司 | A kind of 2,5 dichlorotoleune isomerization catalysts and its preparation method and application |
| CN107413377B (en) * | 2017-05-23 | 2020-02-18 | 中触媒新材料股份有限公司 | 2, 5-dichlorotoluene isomerization catalyst and preparation method and application thereof |
| CN114773146A (en) * | 2022-05-19 | 2022-07-22 | 常州新东化工发展有限公司 | Method for synthesizing 2,4-dichlorotoluene and 3,4-dichlorotoluene by directional chlorination of p-chlorotoluene with a supported catalyst |
| CN115850195A (en) * | 2022-11-29 | 2023-03-28 | 宁夏格瑞精细化工有限公司 | Synthetic method of sulfentrazone intermediate |
| WO2024114106A1 (en) * | 2022-11-29 | 2024-06-06 | 宁夏格瑞精细化工有限公司 | Sulfentrazone intermediate synthesis method |
| CN116063144A (en) * | 2022-12-29 | 2023-05-05 | 柳州东风容泰化工股份有限公司 | A kind of method of producing 2,4-dichlorotoluene |
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