CH494202A - Verfahren zur Herstellung von halogenierten Acetophenonen - Google Patents
Verfahren zur Herstellung von halogenierten AcetophenonenInfo
- Publication number
- CH494202A CH494202A CH848468A CH848468A CH494202A CH 494202 A CH494202 A CH 494202A CH 848468 A CH848468 A CH 848468A CH 848468 A CH848468 A CH 848468A CH 494202 A CH494202 A CH 494202A
- Authority
- CH
- Switzerland
- Prior art keywords
- halobenzene
- dependent
- molar ratio
- reaction
- acetyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 150000008062 acetophenones Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 haloacetyl halide Chemical class 0.000 claims description 19
- 150000005171 halobenzenes Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 14
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 10
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical group ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 10
- 230000001419 dependent effect Effects 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Chemical group 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims description 2
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims 3
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000012346 acetyl chloride Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- QZYNWJQFTJXIRN-UHFFFAOYSA-N 1,2,3,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1 QZYNWJQFTJXIRN-UHFFFAOYSA-N 0.000 description 1
- WXLJJIHGDBUBJM-UHFFFAOYSA-N 1,3,5-triiodobenzene Chemical compound IC1=CC(I)=CC(I)=C1 WXLJJIHGDBUBJM-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- QUGUFLJIAFISSW-UHFFFAOYSA-N 1,4-difluorobenzene Chemical compound FC1=CC=C(F)C=C1 QUGUFLJIAFISSW-UHFFFAOYSA-N 0.000 description 1
- LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 1
- VFDMCQVWSAENIU-UHFFFAOYSA-N 2,2,2-tribromoacetyl bromide Chemical compound BrC(=O)C(Br)(Br)Br VFDMCQVWSAENIU-UHFFFAOYSA-N 0.000 description 1
- LNDJIMKADVTHOS-UHFFFAOYSA-N 2,2,2-trichloroacetyl fluoride Chemical compound FC(=O)C(Cl)(Cl)Cl LNDJIMKADVTHOS-UHFFFAOYSA-N 0.000 description 1
- LQBBYHUQQRZRLK-UHFFFAOYSA-N 2,2-dibromoacetyl chloride Chemical compound ClC(=O)C(Br)Br LQBBYHUQQRZRLK-UHFFFAOYSA-N 0.000 description 1
- CRLSHTZUJTXOEL-UHFFFAOYSA-N 2,2-difluoroacetyl fluoride Chemical compound FC(F)C(F)=O CRLSHTZUJTXOEL-UHFFFAOYSA-N 0.000 description 1
- LKRZCUQFUCYWLZ-UHFFFAOYSA-N 2-chloroacetyl bromide Chemical compound ClCC(Br)=O LKRZCUQFUCYWLZ-UHFFFAOYSA-N 0.000 description 1
- DUFHLGHWZNEJBO-UHFFFAOYSA-N 2-iodoacetyl iodide Chemical compound ICC(I)=O DUFHLGHWZNEJBO-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- 101150101537 Olah gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64480967A | 1967-06-09 | 1967-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH494202A true CH494202A (de) | 1970-07-31 |
Family
ID=24586426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH848468A CH494202A (de) | 1967-06-09 | 1968-06-07 | Verfahren zur Herstellung von halogenierten Acetophenonen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE716290A (enrdf_load_stackoverflow) |
| CH (1) | CH494202A (enrdf_load_stackoverflow) |
| DE (1) | DE1768624A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1567806A (enrdf_load_stackoverflow) |
| GB (1) | GB1187174A (enrdf_load_stackoverflow) |
| NL (1) | NL6807990A (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2519974A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede d'acylation d'halogeno ou trihalogenomethylbenzenes |
| FR2519975A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede de preparation de trifluoromethoxy ou trifluoromethylthiophenylcetones |
| FR2519980A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede de sulfonylation d'halogeno ou trihalogenomethylbenzenes |
| FR2519979A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede de preparation de trifluoromethoxy ou trifluoromethylthiophenylsulfones |
| FR2525589A1 (fr) | 1982-04-22 | 1983-10-28 | Rhone Poulenc Spec Chim | Procede de preparation de trifluoromethoxy ou trifluoromethylthiophenylcetones |
| FR2525588A1 (fr) * | 1982-04-22 | 1983-10-28 | Rhone Poulenc Spec Chim | Procede de preparation de phenylcetones a partir d'halogeno ou trihalogenomethylbenzenes et de composes aliphatiques ou aromatiques trihalogenomethyles |
| DE3247823A1 (de) * | 1982-12-23 | 1984-06-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von ss,4-dichlor-propiophenon |
| DE3836159A1 (de) * | 1988-10-24 | 1990-04-26 | Bayer Ag | Neue fluor enthaltende und an der ch(pfeil abwaerts)3(pfeil abwaerts)-gruppe gegebenenfalls halogenierte acetophenone und deren herstellung aus neuen fluor enthaltenden benzonitrilen |
| CN113121324B (zh) * | 2021-04-20 | 2023-12-22 | 江西永通科技股份有限公司 | 一种2，2，2’，4’，5’-五氯苯乙酮的合成方法 |
| CN116693376A (zh) * | 2023-06-02 | 2023-09-05 | 辽阳大吉化工科技有限公司 | 一种4-溴苯乙酮的制备方法 |
| CN119191952A (zh) * | 2024-09-11 | 2024-12-27 | 合肥立方制药股份有限公司 | 一种森巴考特中间体的制备方法 |
-
1968
- 1968-06-07 GB GB2726868A patent/GB1187174A/en not_active Expired
- 1968-06-07 NL NL6807990A patent/NL6807990A/xx unknown
- 1968-06-07 CH CH848468A patent/CH494202A/de not_active IP Right Cessation
- 1968-06-07 BE BE716290D patent/BE716290A/xx unknown
- 1968-06-07 DE DE19681768624 patent/DE1768624A1/de active Pending
- 1968-06-07 FR FR1567806D patent/FR1567806A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1768624A1 (de) | 1971-11-18 |
| BE716290A (enrdf_load_stackoverflow) | 1968-12-09 |
| GB1187174A (en) | 1970-04-08 |
| NL6807990A (enrdf_load_stackoverflow) | 1968-12-10 |
| FR1567806A (enrdf_load_stackoverflow) | 1969-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1568042A1 (de) | Verfahren zur Herstellung von fluorierten AEthern | |
| CH494202A (de) | Verfahren zur Herstellung von halogenierten Acetophenonen | |
| DE2242519C2 (de) | Verfahren zur Herstellung von gegebenenfalls im Kern substituierten chlorierten Diphenylethern | |
| EP0034741B1 (de) | Verfahren zur Herstellung eines substituierten Bromfluorbenzols und 3-Brom-4-fluorbenzonitril | |
| DE2546532C2 (de) | Verfahren zur Herstellung von Trichlormethyl-trifluormethylbenzolen | |
| EP0124002B1 (de) | Verfahren zur Herstellung von aromatischen Verbindungen, die über ein Heteroatom gebundene perfluorierte Seitenketten enthalten | |
| EP0706987B1 (de) | Verfahren zur Herstellung von alkylierten aromatischen Carbonsäuren und Carbonsäurehalogeniden | |
| DE2437882B2 (de) | Verfahren zur herstellung von estern des 3-phenoxybenzylalkohols | |
| DE3432095A1 (de) | Verfahren zur kernchlorierung von toluol | |
| DE2604277A1 (de) | Verfahren zur herstellung von 2,5- dichlor-p-xylol | |
| CH633244A5 (de) | M-brom-benzotrifluoride. | |
| DE2548970C3 (de) | Verfahren zur Herstellung von Trichlormethyl-trifluormethyl-benzolen | |
| DE2007535A1 (de) | Verfahren zur Herstellung von Triarylphosphinen | |
| DE3104259A1 (de) | Verfahren zur herstellung von polychlorbenzoylchloriden | |
| DE3029368C2 (enrdf_load_stackoverflow) | ||
| EP0024019A1 (de) | Verfahren zur Herstellung von 4-Fluor-3-phenoxy-toluol | |
| CH644093A5 (de) | Verfahren zur herstellung von 2,2-dihalogenvinyl-substituierten cyclopropancarbonsaeure-estern. | |
| DE868296C (de) | Verfahren zur Herstellung von Aryl-trichlor-aethanolen | |
| EP0118082B1 (de) | Phenoxyacetylene und Verfahren zu ihrer Herstellung | |
| DE1101410B (de) | Verfahren zur Herstellung von Polyhalogenadamantanen | |
| DE2258747C2 (de) | Verfahren zur Herstellung von 2,4-Dichlortoluol | |
| DE3836159A1 (de) | Neue fluor enthaltende und an der ch(pfeil abwaerts)3(pfeil abwaerts)-gruppe gegebenenfalls halogenierte acetophenone und deren herstellung aus neuen fluor enthaltenden benzonitrilen | |
| DE4123322C2 (de) | 2-Chlor-3,4,5-trifluorbenzoesäure 2,2'-Dichlor-3,4,5-trifluoracetophenon, 2,2',2'-Trichlor-3,4,5-trifluoracetophenon, 5,2'-Dichlor-2,3,4-trifluoracetophenon und 5,2',2'-Trichlor-2,3,4-trifluoracetophenon und Verfahren zur Herstellung dieser Verbindungen und der isomeren 5-Chlor-2,3,4-trifluorbenzoesäure | |
| DE69514133T2 (de) | Verfahren zur Herstellung von Phosphoniumsalze | |
| DE2123794C3 (de) | Verfahren zur Herstellung von Bromphenylnorbornenen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |