DE1543020B2 - Verfahren zur herstellung von mischungen von monochlortoluolen mit hohem gehalt an p-chlortoluol durch chlorierung von toluol - Google Patents
Verfahren zur herstellung von mischungen von monochlortoluolen mit hohem gehalt an p-chlortoluol durch chlorierung von toluolInfo
- Publication number
- DE1543020B2 DE1543020B2 DE19651543020 DE1543020A DE1543020B2 DE 1543020 B2 DE1543020 B2 DE 1543020B2 DE 19651543020 DE19651543020 DE 19651543020 DE 1543020 A DE1543020 A DE 1543020A DE 1543020 B2 DE1543020 B2 DE 1543020B2
- Authority
- DE
- Germany
- Prior art keywords
- chlorotoluene
- toluene
- chlorination
- catalyst
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title claims description 77
- 238000005660 chlorination reaction Methods 0.000 title claims description 22
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- -1 iron (III) halide Chemical class 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 10
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003613 toluenes Chemical class 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
-
- 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
Landscapes
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39406964A | 1964-09-02 | 1964-09-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1543020A1 DE1543020A1 (de) | 1972-04-20 |
| DE1543020B2 true DE1543020B2 (de) | 1973-05-17 |
| DE1543020C3 DE1543020C3 (enrdf_load_stackoverflow) | 1973-12-20 |
Family
ID=23557425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651543020 Granted DE1543020B2 (de) | 1964-09-02 | 1965-08-18 | Verfahren zur herstellung von mischungen von monochlortoluolen mit hohem gehalt an p-chlortoluol durch chlorierung von toluol |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE691720A (enrdf_load_stackoverflow) |
| CH (1) | CH473073A (enrdf_load_stackoverflow) |
| DE (1) | DE1543020B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1116353A (enrdf_load_stackoverflow) |
| NL (1) | NL6511484A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2634340A1 (de) * | 1975-08-01 | 1977-02-17 | Hooker Chemicals Plastics Corp | Verfahren zur direkten chlorierung von alkylbenzolen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3692850A (en) * | 1970-07-31 | 1972-09-19 | Tenneco Chem | Process for the production of 2,4,5-trichlorotoluene |
| US4031147A (en) * | 1975-08-01 | 1977-06-21 | Hooker Chemicals & Plastics Corporation | Process for directed chlorination of alkylbenzenes |
| US4250122A (en) | 1979-09-07 | 1981-02-10 | Hooker Chemicals & Plastics Corp. | Process and catalyst mixture for the para-directed chlorination of alkylbenzenes |
| DE3131682A1 (de) * | 1981-08-11 | 1983-02-24 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von p-chlortoluol und/oder m-chlortoluol |
| CN104437552B (zh) * | 2014-11-21 | 2017-07-21 | 江苏长三角精细化工有限公司 | 一种以活性炭为载体的甲苯氯化催化剂 |
-
1965
- 1965-07-27 GB GB3209865A patent/GB1116353A/en not_active Expired
- 1965-08-18 DE DE19651543020 patent/DE1543020B2/de active Granted
- 1965-09-02 CH CH1228465A patent/CH473073A/de not_active IP Right Cessation
- 1965-09-02 NL NL6511484A patent/NL6511484A/xx unknown
-
1966
- 1966-12-23 BE BE691720D patent/BE691720A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2634340A1 (de) * | 1975-08-01 | 1977-02-17 | Hooker Chemicals Plastics Corp | Verfahren zur direkten chlorierung von alkylbenzolen |
Also Published As
| Publication number | Publication date |
|---|---|
| CH473073A (de) | 1969-05-31 |
| DE1543020C3 (enrdf_load_stackoverflow) | 1973-12-20 |
| BE691720A (enrdf_load_stackoverflow) | 1967-05-29 |
| NL6511484A (enrdf_load_stackoverflow) | 1966-03-03 |
| GB1116353A (en) | 1968-06-06 |
| DE1543020A1 (de) | 1972-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EI | Miscellaneous see part 3 | ||
| 8339 | Ceased/non-payment of the annual fee |