DE2425355A1 - Verfahren zur herstellung von pyrazinen - Google Patents
Verfahren zur herstellung von pyrazinenInfo
- Publication number
- DE2425355A1 DE2425355A1 DE19742425355 DE2425355A DE2425355A1 DE 2425355 A1 DE2425355 A1 DE 2425355A1 DE 19742425355 DE19742425355 DE 19742425355 DE 2425355 A DE2425355 A DE 2425355A DE 2425355 A1 DE2425355 A1 DE 2425355A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- parts
- oxirane
- radical
- ammonia
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 32
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- 150000003216 pyrazines Chemical class 0.000 claims description 8
- RGCBEUKPJDJRRW-UHFFFAOYSA-N 2-nitrooxirane Chemical class [O-][N+](=O)C1CO1 RGCBEUKPJDJRRW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- -1 aromatic radical Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- HYVJLBUKPYDJCK-UHFFFAOYSA-N 2-nitro-2,3-diphenyloxirane Chemical compound C=1C=CC=CC=1C1([N+](=O)[O-])OC1C1=CC=CC=C1 HYVJLBUKPYDJCK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- KFUSEUYYWQURPO-UPHRSURJSA-N cis-1,2-dichloroethene Chemical group Cl\C=C/Cl KFUSEUYYWQURPO-UPHRSURJSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- ZPKCJXWKXAHCSX-UHFFFAOYSA-N 2,3,5,6-tetraphenylpyrazine Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 ZPKCJXWKXAHCSX-UHFFFAOYSA-N 0.000 description 1
- OQOUIXMIVOBEQH-UHFFFAOYSA-N 2,3-dimethyl-2-nitrooxirane Chemical compound CC1OC1(C)[N+]([O-])=O OQOUIXMIVOBEQH-UHFFFAOYSA-N 0.000 description 1
- QMTUIVOFVMSPAE-UHFFFAOYSA-N 2,5-dimethyl-3,6-diphenylpyrazine Chemical compound CC1=NC(C=2C=CC=CC=2)=C(C)N=C1C1=CC=CC=C1 QMTUIVOFVMSPAE-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- OIIIBIRVFYMCBJ-UHFFFAOYSA-N 2-benzyl-3-nitrooxirane Chemical compound [O-][N+](=O)C1OC1CC1=CC=CC=C1 OIIIBIRVFYMCBJ-UHFFFAOYSA-N 0.000 description 1
- MLPNNOXAINBONM-UHFFFAOYSA-N 2-butyl-2-nitrooxirane Chemical compound CCCCC1([N+]([O-])=O)CO1 MLPNNOXAINBONM-UHFFFAOYSA-N 0.000 description 1
- CGSDFNRKDWYGSB-UHFFFAOYSA-N 2-cyclopentyl-3-nitrooxirane Chemical compound [O-][N+](=O)C1OC1C1CCCC1 CGSDFNRKDWYGSB-UHFFFAOYSA-N 0.000 description 1
- RHWYFHMQQXMXMI-UHFFFAOYSA-N 2-decyl-2-nitrooxirane Chemical compound CCCCCCCCCCC1([N+]([O-])=O)CO1 RHWYFHMQQXMXMI-UHFFFAOYSA-N 0.000 description 1
- QHJRXLHWTICYRN-UHFFFAOYSA-N 2-ethyl-2-nitro-3-phenyloxirane Chemical compound CCC1([N+]([O-])=O)OC1C1=CC=CC=C1 QHJRXLHWTICYRN-UHFFFAOYSA-N 0.000 description 1
- CTRGNPUSQYYAAE-UHFFFAOYSA-N 2-methyl-2-nitro-3-phenyloxirane Chemical compound [O-][N+](=O)C1(C)OC1C1=CC=CC=C1 CTRGNPUSQYYAAE-UHFFFAOYSA-N 0.000 description 1
- QCNDOQFIKASHQH-UHFFFAOYSA-N 2-methyl-2-nitrooxirane Chemical compound [O-][N+](=O)C1(C)CO1 QCNDOQFIKASHQH-UHFFFAOYSA-N 0.000 description 1
- YPJLZZPXCYVDLW-UHFFFAOYSA-N 2-nitro-2-phenyloxirane Chemical compound C=1C=CC=CC=1C1([N+](=O)[O-])CO1 YPJLZZPXCYVDLW-UHFFFAOYSA-N 0.000 description 1
- YOEIERPMRKHSPS-UHFFFAOYSA-N 2-nitro-2-propyloxirane Chemical compound CCCC1([N+]([O-])=O)CO1 YOEIERPMRKHSPS-UHFFFAOYSA-N 0.000 description 1
- YDAMLYAUEQDJRV-UHFFFAOYSA-N 2-nitro-3-(4-nitrophenyl)oxirane Chemical compound [O-][N+](=O)C1OC1C1=CC=C([N+]([O-])=O)C=C1 YDAMLYAUEQDJRV-UHFFFAOYSA-N 0.000 description 1
- KXGGQNWQCOOXAG-UHFFFAOYSA-N 3-cyclohexyl-2-methyl-2-nitrooxirane Chemical compound [O-][N+](=O)C1(C)OC1C1CCCCC1 KXGGQNWQCOOXAG-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- LIRXANHEEUXTDB-UHFFFAOYSA-N C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)C1=CN=CC=N1 Chemical compound C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)C1=CN=CC=N1 LIRXANHEEUXTDB-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ALBXXUYMWJRKSP-UHFFFAOYSA-N pyrazine-2,3,5-tricarbonitrile Chemical class N#CC1=CN=C(C#N)C(C#N)=N1 ALBXXUYMWJRKSP-UHFFFAOYSA-N 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical class OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742425355 DE2425355A1 (de) | 1974-05-25 | 1974-05-25 | Verfahren zur herstellung von pyrazinen |
| US05/572,136 US4064124A (en) | 1974-05-25 | 1975-04-28 | Manufacture of pyrazines |
| IT2279575A IT1037680B (it) | 1974-05-25 | 1975-04-28 | Processo per la preparzione di pirazine |
| CA225,859A CA1041510A (en) | 1974-05-25 | 1975-04-28 | Manufacture of pyrazines |
| GB1977075A GB1499768A (en) | 1974-05-25 | 1975-05-12 | Manufacture of pyrazines |
| CH651275A CH593268A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-25 | 1975-05-21 | |
| NL7506038A NL7506038A (nl) | 1974-05-25 | 1975-05-22 | Werkwijze voor het bereiden van pyrazinen. |
| BE156672A BE829444A (fr) | 1974-05-25 | 1975-05-23 | Procede de preparation de derives de pyrazine |
| FR7516168A FR2272086B3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-25 | 1975-05-23 | |
| JP6203675A JPS511483A (ja) | 1974-05-25 | 1975-05-26 | Pirajinnoseiho |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742425355 DE2425355A1 (de) | 1974-05-25 | 1974-05-25 | Verfahren zur herstellung von pyrazinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2425355A1 true DE2425355A1 (de) | 1975-12-04 |
Family
ID=5916449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742425355 Withdrawn DE2425355A1 (de) | 1974-05-25 | 1974-05-25 | Verfahren zur herstellung von pyrazinen |
Country Status (9)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1255740B1 (en) | 2000-02-16 | 2005-10-19 | Neurogen Corporation | Substituted arylpyrazines |
-
1974
- 1974-05-25 DE DE19742425355 patent/DE2425355A1/de not_active Withdrawn
-
1975
- 1975-04-28 IT IT2279575A patent/IT1037680B/it active
- 1975-04-28 CA CA225,859A patent/CA1041510A/en not_active Expired
- 1975-05-12 GB GB1977075A patent/GB1499768A/en not_active Expired
- 1975-05-21 CH CH651275A patent/CH593268A5/xx not_active IP Right Cessation
- 1975-05-22 NL NL7506038A patent/NL7506038A/xx unknown
- 1975-05-23 BE BE156672A patent/BE829444A/xx unknown
- 1975-05-23 FR FR7516168A patent/FR2272086B3/fr not_active Expired
- 1975-05-26 JP JP6203675A patent/JPS511483A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7506038A (nl) | 1975-11-27 |
| FR2272086A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-19 |
| GB1499768A (en) | 1978-02-01 |
| JPS511483A (ja) | 1976-01-08 |
| CA1041510A (en) | 1978-10-31 |
| IT1037680B (it) | 1979-11-20 |
| BE829444A (fr) | 1975-11-24 |
| CH593268A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-11-30 |
| FR2272086B3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |