NO742233L - - Google Patents
Info
- Publication number
- NO742233L NO742233L NO742233A NO742233A NO742233L NO 742233 L NO742233 L NO 742233L NO 742233 A NO742233 A NO 742233A NO 742233 A NO742233 A NO 742233A NO 742233 L NO742233 L NO 742233L
- Authority
- NO
- Norway
- Prior art keywords
- acetone
- reaction
- carried out
- acetonin
- diacetone alcohol
- Prior art date
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 61
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 30
- PIFBMJMXJMZZRG-UHFFFAOYSA-N 2,2,4,6,6-pentamethyl-1,5-dihydropyrimidine Chemical compound CC1=NC(C)(C)NC(C)(C)C1 PIFBMJMXJMZZRG-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- CQTRUFMMCCOKTA-UHFFFAOYSA-N 4-amino-4-methylpentan-2-one Chemical compound CC(=O)CC(C)(C)N CQTRUFMMCCOKTA-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 5
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 claims description 2
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 claims description 2
- 229930193351 phorone Natural products 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 2
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 claims 2
- 239000003791 organic solvent mixture Substances 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- -1 aromatics Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 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
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PWMAQBHZHRJRCB-UHFFFAOYSA-N 2,2,4,6,6-pentamethyl-1,5-dihydropyrimidine;hydrate Chemical compound O.CC1=NC(C)(C)NC(C)(C)C1 PWMAQBHZHRJRCB-UHFFFAOYSA-N 0.000 description 1
- SFDODBGIDPNFEH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-one;hydrate Chemical compound O.CC1(C)CC(=O)CC(C)(C)N1 SFDODBGIDPNFEH-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LSYJHRREPKXURZ-UHFFFAOYSA-N pyrimidine;hydrate Chemical compound O.C1=CN=CN=C1 LSYJHRREPKXURZ-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D211/74—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH950673A CH574413A5 (en) | 1973-06-29 | 1973-06-29 | 2,2,6,6-Tetra-methyl-4-oxo-piperidine prepn. - from 2,2,4,4,6-penta-methyl-2,3,4,5-tetra-hydro-pyrimidine by heating in anhydrous medium |
| CH544074A CH582145A5 (en) | 1974-04-19 | 1974-04-19 | 2,2,6,6-Tetra-methyl-4-oxo-piperidine prepn. - from 2,2,4,4,6-penta-methyl-2,3,4,5-tetra-hydro-pyrimidine by heating in anhydrous medium |
| CH701974 | 1974-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO742233L true NO742233L (fi) | 1975-01-27 |
Family
ID=27175211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO742233A NO742233L (fi) | 1973-06-29 | 1974-06-19 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3960875A (fi) |
| JP (1) | JPS5036474A (fi) |
| AR (1) | AR208393A1 (fi) |
| AT (1) | AT338263B (fi) |
| BG (1) | BG27081A3 (fi) |
| BR (1) | BR7405080D0 (fi) |
| CA (1) | CA1027952A (fi) |
| CS (1) | CS200467B2 (fi) |
| DD (1) | DD112444A5 (fi) |
| DE (1) | DE2429935C3 (fi) |
| DK (1) | DK140406B (fi) |
| EG (1) | EG11230A (fi) |
| ES (1) | ES427548A1 (fi) |
| FI (1) | FI190674A (fi) |
| FR (1) | FR2235118B1 (fi) |
| GB (1) | GB1461701A (fi) |
| HU (1) | HU169841B (fi) |
| IE (1) | IE39521B1 (fi) |
| IL (1) | IL45092A (fi) |
| IT (1) | IT1021055B (fi) |
| LU (1) | LU70388A1 (fi) |
| NL (1) | NL7408411A (fi) |
| NO (1) | NO742233L (fi) |
| RO (1) | RO67193A (fi) |
| SE (1) | SE7408173L (fi) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2916471A1 (de) * | 1979-04-24 | 1980-11-06 | Hoechst Ag | Verfahren zur herstellung von 2,2, 6,6-tetramethylpiperidon-4 |
| US4734502A (en) * | 1986-12-22 | 1988-03-29 | Ici Americas Inc. | Process for the preparation of 2,2,6,6-tetramethyl-4-oxopiperidine |
| DE102012215900A1 (de) | 2012-09-07 | 2014-05-15 | Evonik Industries Ag | Verfahren zur Herstellung und Aufarbeitung eines Triacetonamin-haltigen Reaktionsgemisches |
| DE102012215903A1 (de) | 2012-09-07 | 2014-03-13 | Evonik Industries Ag | Verfahren zur Behandlung eines Abwasserstroms, der bei der Aufarbeitung eines Triacetonamin-haltigen Reaktionsgemisches entsteht |
| CN108484482A (zh) * | 2018-05-01 | 2018-09-04 | 衡水凯亚化工有限公司 | 一种利用合成三丙酮胺过程副产物制备三丙酮胺的方法 |
| CN108383776A (zh) * | 2018-05-01 | 2018-08-10 | 衡水凯亚化工有限公司 | 一种利用丙酮和合成三丙酮胺过程副产物制备三丙酮胺 |
| EP3663284B1 (de) | 2018-12-07 | 2021-02-03 | Evonik Operations GmbH | Verbessertes verfahren zur herstellung von triacetonamin |
| EP3750876A1 (de) | 2019-06-13 | 2020-12-16 | Evonik Operations GmbH | Verfahren zur herstellung von triacetonamin, 2,2,4,6-tetramethylpiperidin und/oder den salzen des 2,2,4,6-tetramethylpiperidins |
| US11731940B2 (en) | 2020-05-07 | 2023-08-22 | Evonik Operations Gmbh | Process for preparing triacetonamine |
| EP4279484A1 (de) | 2022-05-17 | 2023-11-22 | Sabo GmbH | Verbessertes verfahren zur herstellung von triacetonamin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3513170A (en) * | 1966-07-23 | 1970-05-19 | Sankyo Co | Preparation of 2,2,6,6-tetramethyl-4-oxopiperidine |
-
1974
- 1974-01-01 AR AR254315A patent/AR208393A1/es active
- 1974-06-19 NO NO742233A patent/NO742233L/no unknown
- 1974-06-20 DK DK330974AA patent/DK140406B/da unknown
- 1974-06-20 SE SE7408173A patent/SE7408173L/xx unknown
- 1974-06-20 FI FI1906/74A patent/FI190674A/fi unknown
- 1974-06-21 GB GB2760274A patent/GB1461701A/en not_active Expired
- 1974-06-21 DE DE2429935A patent/DE2429935C3/de not_active Expired
- 1974-06-21 CS CS744395A patent/CS200467B2/cs unknown
- 1974-06-21 HU HUCI1484A patent/HU169841B/hu unknown
- 1974-06-21 NL NL7408411A patent/NL7408411A/xx not_active Application Discontinuation
- 1974-06-21 RO RO7479252A patent/RO67193A/ro unknown
- 1974-06-21 IL IL45092A patent/IL45092A/en unknown
- 1974-06-21 IE IE1300/74A patent/IE39521B1/xx unknown
- 1974-06-21 AT AT517874A patent/AT338263B/de not_active IP Right Cessation
- 1974-06-21 US US05/481,935 patent/US3960875A/en not_active Expired - Lifetime
- 1974-06-21 JP JP49071217A patent/JPS5036474A/ja active Pending
- 1974-06-21 FR FR7421685A patent/FR2235118B1/fr not_active Expired
- 1974-06-21 BG BG027041A patent/BG27081A3/xx not_active Expired
- 1974-06-21 IT IT24296/74A patent/IT1021055B/it active
- 1974-06-21 DD DD179371A patent/DD112444A5/xx unknown
- 1974-06-21 LU LU70388*A patent/LU70388A1/xx unknown
- 1974-06-21 ES ES427548A patent/ES427548A1/es not_active Expired
- 1974-06-21 CA CA203,061A patent/CA1027952A/en not_active Expired
- 1974-06-21 BR BR5080/74A patent/BR7405080D0/pt unknown
- 1974-06-24 EG EG242/74A patent/EG11230A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| DK140406B (da) | 1979-08-20 |
| ES427548A1 (es) | 1976-08-01 |
| FR2235118A1 (fi) | 1975-01-24 |
| AT338263B (de) | 1977-08-10 |
| LU70388A1 (fi) | 1976-04-13 |
| US3960875A (en) | 1976-06-01 |
| NL7408411A (fi) | 1974-12-31 |
| GB1461701A (en) | 1977-01-19 |
| FR2235118B1 (fi) | 1978-01-13 |
| IL45092A0 (en) | 1974-09-10 |
| DE2429935B2 (de) | 1980-10-02 |
| DK330974A (fi) | 1975-02-17 |
| BR7405080D0 (pt) | 1975-01-21 |
| IL45092A (en) | 1976-12-31 |
| IE39521L (en) | 1974-12-26 |
| DD112444A5 (fi) | 1975-04-12 |
| RO67193A (fr) | 1979-06-15 |
| CA1027952A (en) | 1978-03-14 |
| ATA517874A (de) | 1976-12-15 |
| HU169841B (fi) | 1977-02-28 |
| CS200467B2 (en) | 1980-09-15 |
| JPS5036474A (fi) | 1975-04-05 |
| DE2429935A1 (de) | 1975-01-16 |
| EG11230A (en) | 1977-01-31 |
| SE7408173L (fi) | 1974-12-30 |
| AR208393A1 (es) | 1976-12-27 |
| IE39521B1 (en) | 1978-10-25 |
| AU7033774A (en) | 1976-01-08 |
| BG27081A3 (bg) | 1979-08-15 |
| DK140406C (fi) | 1980-01-21 |
| FI190674A (fi) | 1974-12-30 |
| DE2429935C3 (de) | 1981-07-23 |
| IT1021055B (it) | 1978-01-30 |
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