DE4415777A1 - Verfahren zur Herstellung von Chloraromaten - Google Patents
Verfahren zur Herstellung von ChloraromatenInfo
- Publication number
- DE4415777A1 DE4415777A1 DE4415777A DE4415777A DE4415777A1 DE 4415777 A1 DE4415777 A1 DE 4415777A1 DE 4415777 A DE4415777 A DE 4415777A DE 4415777 A DE4415777 A DE 4415777A DE 4415777 A1 DE4415777 A1 DE 4415777A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- halides
- hydrogen
- solvent
- 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.)
- Withdrawn
Links
- 125000000217 alkyl group Chemical group 0.000 title abstract description 5
- 125000003118 aryl group Chemical group 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 23
- -1 antimony halides Chemical class 0.000 claims abstract description 20
- 239000002841 Lewis acid Substances 0.000 claims abstract description 13
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 150000007938 chlorocyclic compounds Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 7
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 abstract description 5
- 238000010438 heat treatment Methods 0.000 abstract description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- VDXLAYAQGYCQEO-UHFFFAOYSA-N 2-chloro-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1Cl VDXLAYAQGYCQEO-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- WPHOWHZYEOSZIS-UHFFFAOYSA-N (2,6-dimethylphenyl) carbonochloridate Chemical compound CC1=CC=CC(C)=C1OC(Cl)=O WPHOWHZYEOSZIS-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 150000001564 phenyl benzoates Chemical class 0.000 description 2
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical class ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/363—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by elimination of carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4415777A DE4415777A1 (de) | 1994-05-05 | 1994-05-05 | Verfahren zur Herstellung von Chloraromaten |
| EP95106074A EP0694513B1 (de) | 1994-05-05 | 1995-04-24 | Verfahren zur Herstellung von Chloraromaten |
| DE59504047T DE59504047D1 (de) | 1994-05-05 | 1995-04-24 | Verfahren zur Herstellung von Chloraromaten |
| JP12732795A JP3535608B2 (ja) | 1994-05-05 | 1995-04-27 | 塩化芳香族の製造方法 |
| US08/812,197 US5874655A (en) | 1994-05-05 | 1997-03-06 | Process for the preparation of chlorinated aromatics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4415777A DE4415777A1 (de) | 1994-05-05 | 1994-05-05 | Verfahren zur Herstellung von Chloraromaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4415777A1 true DE4415777A1 (de) | 1995-11-09 |
Family
ID=6517306
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4415777A Withdrawn DE4415777A1 (de) | 1994-05-05 | 1994-05-05 | Verfahren zur Herstellung von Chloraromaten |
| DE59504047T Expired - Fee Related DE59504047D1 (de) | 1994-05-05 | 1995-04-24 | Verfahren zur Herstellung von Chloraromaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59504047T Expired - Fee Related DE59504047D1 (de) | 1994-05-05 | 1995-04-24 | Verfahren zur Herstellung von Chloraromaten |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5874655A (enExample) |
| EP (1) | EP0694513B1 (enExample) |
| JP (1) | JP3535608B2 (enExample) |
| DE (2) | DE4415777A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108530297B (zh) * | 2017-03-03 | 2021-09-24 | 联化科技股份有限公司 | 2-氯-3-甲基苯甲酸及其中间体的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE857350C (de) * | 1943-05-13 | 1952-11-27 | Basf Ag | Verfahren zur Herstellung von Alkyl- bzw. Aralkylchloriden |
| DE2931777A1 (de) * | 1979-08-04 | 1981-02-26 | Basf Ag | Verfahren zur herstellung von alkylchloriden |
| DE3466872D1 (en) * | 1983-03-01 | 1987-11-26 | Ici Plc | Fluorination process |
| US4814524A (en) * | 1986-07-31 | 1989-03-21 | Ppg Industries, Inc. | Method for converting organic chloroformate to the corresponding organic chloride |
| IE903987A1 (en) * | 1989-11-06 | 1991-05-08 | Rhone Poulenc Chimie | Process for the preparation of fluorinated aromatic¹derivatives and lewis acid based catalyst therefor |
| DE4225763A1 (de) * | 1992-08-04 | 1994-02-10 | Bayer Ag | Verfahren zur Herstellung von Halogenaromaten |
-
1994
- 1994-05-05 DE DE4415777A patent/DE4415777A1/de not_active Withdrawn
-
1995
- 1995-04-24 EP EP95106074A patent/EP0694513B1/de not_active Expired - Lifetime
- 1995-04-24 DE DE59504047T patent/DE59504047D1/de not_active Expired - Fee Related
- 1995-04-27 JP JP12732795A patent/JP3535608B2/ja not_active Expired - Fee Related
-
1997
- 1997-03-06 US US08/812,197 patent/US5874655A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0694513A3 (enExample) | 1996-02-07 |
| EP0694513B1 (de) | 1998-10-28 |
| JPH07304697A (ja) | 1995-11-21 |
| JP3535608B2 (ja) | 2004-06-07 |
| DE59504047D1 (de) | 1998-12-03 |
| US5874655A (en) | 1999-02-23 |
| EP0694513A2 (de) | 1996-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |