DE2062434A1 - - Google Patents
Info
- Publication number
- DE2062434A1 DE2062434A1 DE19702062434 DE2062434A DE2062434A1 DE 2062434 A1 DE2062434 A1 DE 2062434A1 DE 19702062434 DE19702062434 DE 19702062434 DE 2062434 A DE2062434 A DE 2062434A DE 2062434 A1 DE2062434 A1 DE 2062434A1
- Authority
- DE
- Germany
- Prior art keywords
- halides
- acid
- saponification
- formic acid
- reaction
- 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.)
- Pending
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 14
- 235000019253 formic acid Nutrition 0.000 claims description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 13
- 238000007127 saponification reaction Methods 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000002739 metals Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 7
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical class ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 4
- -1 halogen benzoyl halides Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000003842 bromide salts Chemical class 0.000 description 2
- 229910002090 carbon oxide Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- NFICEVMIQXDAEP-UHFFFAOYSA-N 1,3-dichloro-2-(trichloromethyl)benzene Chemical compound ClC1=CC=CC(Cl)=C1C(Cl)(Cl)Cl NFICEVMIQXDAEP-UHFFFAOYSA-N 0.000 description 1
- MFHPYLFZSCSNST-UHFFFAOYSA-N 1-chloro-2-(trichloromethyl)benzene Chemical compound ClC1=CC=CC=C1C(Cl)(Cl)Cl MFHPYLFZSCSNST-UHFFFAOYSA-N 0.000 description 1
- LVZPKYYPPLUECL-UHFFFAOYSA-N 1-chloro-4-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1 LVZPKYYPPLUECL-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical group CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-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
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/093—Preparation of carboxylic acids or their salts, halides or anhydrides by hydrolysis of —CX3 groups, X being halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702062434 DE2062434A1 (enrdf_load_stackoverflow) | 1970-12-18 | 1970-12-18 | |
| CH1728471A CH554305A (de) | 1970-12-18 | 1971-11-26 | Verfahren zur herstellung von halogenbenzoylhalogeniden und halogennitrobenzoylhalogeniden. |
| GB5865471A GB1363089A (en) | 1970-12-18 | 1971-12-17 | Process for the production of holobenzoyl halides and halonitrobenzoyl halides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702062434 DE2062434A1 (enrdf_load_stackoverflow) | 1970-12-18 | 1970-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2062434A1 true DE2062434A1 (enrdf_load_stackoverflow) | 1972-06-22 |
Family
ID=5791432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702062434 Pending DE2062434A1 (enrdf_load_stackoverflow) | 1970-12-18 | 1970-12-18 |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH554305A (enrdf_load_stackoverflow) |
| DE (1) | DE2062434A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1363089A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0009205A1 (de) * | 1978-09-23 | 1980-04-02 | Bayer Ag | Verfahren zur Herstellung von gegebenenfalls substituiertem Benzoylchlorid |
| EP0024516A1 (de) * | 1979-07-18 | 1981-03-11 | Bayer Ag | 4-Fluor-3-brombenzoylfluorid, Verfahren zu seiner Herstellung und zur Herstellung von 4-Fluor-3-brombenzoesäure daraus |
-
1970
- 1970-12-18 DE DE19702062434 patent/DE2062434A1/de active Pending
-
1971
- 1971-11-26 CH CH1728471A patent/CH554305A/xx not_active IP Right Cessation
- 1971-12-17 GB GB5865471A patent/GB1363089A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0009205A1 (de) * | 1978-09-23 | 1980-04-02 | Bayer Ag | Verfahren zur Herstellung von gegebenenfalls substituiertem Benzoylchlorid |
| EP0024516A1 (de) * | 1979-07-18 | 1981-03-11 | Bayer Ag | 4-Fluor-3-brombenzoylfluorid, Verfahren zu seiner Herstellung und zur Herstellung von 4-Fluor-3-brombenzoesäure daraus |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1363089A (en) | 1974-08-14 |
| CH554305A (de) | 1974-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2841541A1 (de) | Verfahren zur herstellung von gegebenenfalls substituiertem benzoylchlorid | |
| EP0026291B1 (de) | Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd | |
| DE2062434A1 (enrdf_load_stackoverflow) | ||
| EP0078993B1 (de) | Verfahren zur Herstellung von Benzoylchlorid | |
| CH413814A (de) | Verfahren zur Herstellung von 2,5-Dichlor-, 2,5-Dibrom- und 2,5-Dijod-terephthalsäure | |
| DE2423316C2 (de) | Verfahren zur Herstellung von 4-Chlor-5-oxo-hexansäurenitril und 6-Chlor-5-oxo-hexansäure-nitril | |
| DE2026817A1 (de) | Verfahren zur Herstellung von Monochlorbenzaldehyden | |
| DE624964C (de) | Verfahren zur photochemischen Oxydation organischer und anorganischer Verbindungen | |
| DE2558517A1 (de) | 4-methylimidazol-5-carbonsaeureisopropylester und ein neues verfahren zu seiner herstellung | |
| DE2115944B2 (de) | Verfahren zur herstellung von o-sulfobenzimiden | |
| DE1618157C (de) | Verfahren zur Herstellung von Halogenoder Halogennitrobenzaldehyden | |
| DE1618157B1 (de) | Verfahren zur Herstellung von Halogen- oder Halogennitrobenzaldehyden | |
| EP0012214B1 (de) | Verfahren zur Herstellung von 3-Phenoxy-benzylalkoholen | |
| DE3602180A1 (de) | Verfahren zur herstellung von brenzkatechin und hydrochinon | |
| DE908135C (de) | Verfahren zur Herstellung von mehrwertigen Alkoholen | |
| DE2743924A1 (de) | Verfahren zur herstellung ungesaettigter diestern | |
| AT211806B (de) | Verfahren zur Herstellung von ungesättigten aliphatischen Verbindungen | |
| DE1768179C3 (de) | Chlorcarbonylisocyanat und Verfahren zur Herstellung von Isocyanaten | |
| DE1768314C3 (de) | Verfahren zur Herstellung von Estern | |
| DE895597C (de) | Verfahren zur Herstellung von Vinylestern | |
| DE1217940B (de) | Herstellung von aromatisch substituierten AEthern | |
| DE1903701A1 (de) | Verfahren zur Herstellung von 1,2-Benzisoxazolen | |
| DE1004160B (de) | Verfahren zur Herstellung von reiner Terephthalsaeure | |
| DE1251728B (de) | Verfahren zur Herstellung von primären Alkoholen | |
| DE1211632B (de) | Verfahren zur Herstellung von 1, 2, 3, 4-Tetrachlor-9-anthron |