DE2951792A1 - Verfahren zur herstellung von 3- phenoxybenzaldehyd - Google Patents
Verfahren zur herstellung von 3- phenoxybenzaldehydInfo
- Publication number
- DE2951792A1 DE2951792A1 DE19792951792 DE2951792A DE2951792A1 DE 2951792 A1 DE2951792 A1 DE 2951792A1 DE 19792951792 DE19792951792 DE 19792951792 DE 2951792 A DE2951792 A DE 2951792A DE 2951792 A1 DE2951792 A1 DE 2951792A1
- Authority
- DE
- Germany
- Prior art keywords
- phenoxybenzaldehyde
- solvent
- mixture
- reaction
- chloride
- 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
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- -1 3-phenoxybenzyl Chemical group 0.000 claims description 23
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- 239000002728 pyrethroid Substances 0.000 claims description 13
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
- 150000001924 cycloalkanes Chemical class 0.000 claims description 11
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 11
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229940126062 Compound A Drugs 0.000 description 20
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QUYVTGFWFHQVRO-UHFFFAOYSA-N 1-(chloromethyl)-3-phenoxybenzene Chemical compound ClCC1=CC=CC(OC=2C=CC=CC=2)=C1 QUYVTGFWFHQVRO-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- JOVSDWRNVGOQNK-UHFFFAOYSA-N 1-(dichloromethyl)-3-phenoxybenzene Chemical compound ClC(Cl)C1=CC=CC(OC=2C=CC=CC=2)=C1 JOVSDWRNVGOQNK-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 2
- 239000004914 cyclooctane Substances 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012485 toluene extract Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical class OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 1
- CHLAOFANYRDCPD-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(Cl)=O CHLAOFANYRDCPD-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 238000006007 Sommelet synthesis reaction Methods 0.000 description 1
- 241000656145 Thyrsites atun Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- POCNHGFJLGYFIK-UHFFFAOYSA-N methylcyclooctane Chemical compound CC1CCCCCCC1 POCNHGFJLGYFIK-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical group 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
Classifications
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7900169 | 1979-01-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2951792A1 true DE2951792A1 (de) | 1980-07-17 |
| DE2951792C2 DE2951792C2 (enrdf_load_stackoverflow) | 1989-06-29 |
Family
ID=10502295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792951792 Granted DE2951792A1 (de) | 1979-01-03 | 1979-12-21 | Verfahren zur herstellung von 3- phenoxybenzaldehyd |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5592336A (enrdf_load_stackoverflow) |
| BR (1) | BR7908433A (enrdf_load_stackoverflow) |
| CH (1) | CH641435A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2951792A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2445825B1 (enrdf_load_stackoverflow) |
| IN (1) | IN153513B (enrdf_load_stackoverflow) |
| IT (1) | IT1126686B (enrdf_load_stackoverflow) |
| NL (1) | NL193562C (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2704512A1 (de) * | 1976-02-05 | 1977-08-11 | Shell Int Research | Verfahren zur herstellung von m-aryloxybenzaldehyden |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5325530A (en) * | 1976-08-20 | 1978-03-09 | Sumitomo Chem Co Ltd | Purification of aldehydes |
| US4108904A (en) * | 1976-09-22 | 1978-08-22 | American Cyanamid Company | Process for the preparation of m-phenoxybenzaldehyde |
| FR2383153A1 (fr) * | 1977-03-09 | 1978-10-06 | Roussel Uclaf | Nouveaux halogenures de benzylidene, procede de preparation et application a la preparation du metaphenoxy benzaldehyde |
-
1979
- 1979-12-21 JP JP16576379A patent/JPS5592336A/ja active Granted
- 1979-12-21 IT IT28362/79A patent/IT1126686B/it active
- 1979-12-21 DE DE19792951792 patent/DE2951792A1/de active Granted
- 1979-12-21 BR BR7908433A patent/BR7908433A/pt not_active IP Right Cessation
- 1979-12-21 IN IN933/DEL/79A patent/IN153513B/en unknown
- 1979-12-21 FR FR797931439A patent/FR2445825B1/fr not_active Expired
- 1979-12-21 CH CH1142379A patent/CH641435A5/de not_active IP Right Cessation
-
1980
- 1980-01-02 NL NL8000004A patent/NL193562C/nl not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2704512A1 (de) * | 1976-02-05 | 1977-08-11 | Shell Int Research | Verfahren zur herstellung von m-aryloxybenzaldehyden |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2445825A1 (fr) | 1980-08-01 |
| IT7928362A0 (it) | 1979-12-21 |
| JPS6239145B2 (enrdf_load_stackoverflow) | 1987-08-21 |
| JPS5592336A (en) | 1980-07-12 |
| NL193562C (nl) | 2000-02-02 |
| DE2951792C2 (enrdf_load_stackoverflow) | 1989-06-29 |
| NL8000004A (nl) | 1980-07-07 |
| IN153513B (enrdf_load_stackoverflow) | 1984-07-21 |
| FR2445825B1 (fr) | 1985-07-26 |
| BR7908433A (pt) | 1980-09-23 |
| CH641435A5 (en) | 1984-02-29 |
| NL193562B (nl) | 1999-10-01 |
| IT1126686B (it) | 1986-05-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2704512C2 (enrdf_load_stackoverflow) | ||
| DE2437882C3 (de) | Verfahren zur Herstellung von Estern des 3-Phenoxybenzylalkohols | |
| DE60109939T2 (de) | Verfahren zur herstellung von fluorierten & chlorierten benzaldehyden | |
| DE2849692C3 (de) | Verfahren zur Herstellung von p-tert.- Butylbenzaldehyd und dessen am Kern durch Halogen monosubstituierten Derivaten | |
| DE2616681A1 (de) | Verfahren zur reduktiven dehydrohalogenierung von alpha-halogenalkoholen | |
| DE2822472A1 (de) | Verfahren zur herstellung von estern von m-phenoxy-benzylalkohol und seiner alpha-cyano- und alpha-aethinylderivate mit carbonsaeuren | |
| DE2951792A1 (de) | Verfahren zur herstellung von 3- phenoxybenzaldehyd | |
| DE2527289A1 (de) | Verfahren zur herstellung von alkylacetophenonen | |
| DE2716771A1 (de) | Verfahren zur herstellung von estern von m-phenoxybenzylalkohol und seiner alpha-cyano- und alpha-aethinylderivate mit carbonsaeuren | |
| EP0034837A1 (de) | P-tert.-Butylbenzalbromid und dessen am Kern durch Halogen substituierte Derivate | |
| DE2716772A1 (de) | Verfahren zur herstellung von estern von m-phenoxybenzylalkohol und seiner alpha-cyano- und alpha-aethinylderivate mit carbonsaeuren | |
| DE2841664C3 (de) | Verfahren zur Herstellung von Phenoxybenzylbromid bzw. Phenoxybenzalbromid | |
| DE1001259C2 (de) | Verfahren zur Herstellung von Derivaten des Nortricyclens | |
| DE3726891A1 (de) | Neue dichlortrifluormethylnitrotoluole und deren umwandlung in aminotrifluormethyltoluole | |
| DE69314637T2 (de) | Verfahren zur herstellung und wiedergewinnung von halogennitroalkanen in hoher ausbeute | |
| DE1668280C3 (de) | Verfahren zur Herstellung von Dihydromyrcenol | |
| DE2121251B2 (de) | Verfahren zur herstellung von dichloracetoxypropan | |
| DE2925012C2 (de) | Verfahren zur Herstellung von Pentachlor-3-butensäureestern | |
| EP0014835B1 (de) | Bis-(brom- und chlor-substituiertes propenyl)-äther, Verfahren zu seiner Herstellung und seine Verwendung bei der Herstellung von Trichloracrolein | |
| DE2306335C3 (de) | Verfahren zur Herstellung von Dichloracetaldehyd | |
| DE2108926C3 (de) | Verfahren zur Herstellung von 3-Acyl-4-hydroxy-buten-(2)-saurelactonen | |
| AT218510B (de) | Verfahren zur Herstellung von 2, 6-Dichlorbenzalchlorid oder 2, 6-Dichlorbenzaldehyd | |
| EP0286969B1 (de) | Verfahren zur Herstellung von trans-2,2-Dimethyl-3-(2,2-dichlorvinyl)-cyclopropancarbonsäure | |
| DE1468142C (enrdf_load_stackoverflow) | ||
| DE2659973B1 (de) | Halogencarbonylverbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |