DE2824976A1 - Cycloalkanolderivate, verfahren zu ihrer herstellung und weiterverarbeitung - Google Patents
Cycloalkanolderivate, verfahren zu ihrer herstellung und weiterverarbeitungInfo
- Publication number
- DE2824976A1 DE2824976A1 DE19782824976 DE2824976A DE2824976A1 DE 2824976 A1 DE2824976 A1 DE 2824976A1 DE 19782824976 DE19782824976 DE 19782824976 DE 2824976 A DE2824976 A DE 2824976A DE 2824976 A1 DE2824976 A1 DE 2824976A1
- Authority
- DE
- Germany
- Prior art keywords
- alkylamine
- dehydrated
- hydroxylamine
- alkanol
- oxide
- 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
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 18
- 150000001925 cycloalkenes Chemical class 0.000 claims description 15
- 150000003973 alkyl amines Chemical class 0.000 claims description 13
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 11
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 11
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 4
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- DEKLMTVOQOWFOL-UHFFFAOYSA-N 2-propan-2-yloxycyclohexan-1-ol Chemical compound CC(C)OC1CCCCC1O DEKLMTVOQOWFOL-UHFFFAOYSA-N 0.000 description 7
- ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- -1 cycloalkyl radical Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- VIZZKUAVHMEIJJ-UHFFFAOYSA-N 1-propan-2-yloxycyclohexan-1-ol Chemical compound CC(C)OC1(O)CCCCC1 VIZZKUAVHMEIJJ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- NWDMNHLBVGULHK-UHFFFAOYSA-N 2-(hydroxyamino)cyclohexan-1-ol Chemical compound ONC1CCCCC1O NWDMNHLBVGULHK-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000015155 buttermilk Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FFQYMTMKMLRXLJ-UHFFFAOYSA-N cyclohexanol;phenol Chemical class OC1CCCCC1.OC1=CC=CC=C1 FFQYMTMKMLRXLJ-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
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)
Description
Telefon: (04181) 44 57
% oQ
98 86 20mm Hg
98 | .7 | 85-90 | 5mm | Hg |
98 | 95 | 5mm | Hg | |
9h | .2 | 120 | 5,mm | Hg |
97 | 135 | 5mm | Hg | |
Claims (1)
- Pat entansprücheworin η eine ganze Zahl, X-OR, -NHR oder -NHOH und R einenAlkylgegebenenfalls substituierten, gerad- oder verzweigtkettigen oder Cyoloalkylrest, oder einen gegebenenfalls substituierten Aryl- oder Aralkylrest bedeuten.2. Cycloalkanolderivate der allgemeinen Formel nach. Anspruchvon 3-10
1, worin η eine ganze ZahlVund R eine geradkettige Alkyl- oder eine Cycloalkylgruppe mit bis zu 12 C-Atomen bedeuten.3. Verfahren zur Herstellung der Verbindungen nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß ein Alkanol ROH, ein Alkylamin RNH- oder Hydroxylamin mit einem Cycloalkenoxid der" allgemeinen FormelCH2 2in Gegenwart eines sauren Katalysators umgesetzt wird.Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß die Reaktion bei Temperaturen bis zur Riickflußtemperatur809851/0833ORIGINAL INSPECTEDdurchgeführt wird.5. Verfahren nach Atispruch 3 oder kf dadurch gekennzeichnet, daß das Alkanol, Alkylamin bzw. Hydroxylamin im Überschuß eingesetzt wird.6. Verfahren nach einem der"Ansprüche 3 bis 5, dadurch gekennzeichnet, daß Isopropanol mit Cyclohexenoxid umgesetzt wird.7. Verfahren zur Herstellung eines in ortho-Stellung substituierten Phenolderxvates, dadurch gekennzeichnet, daß die Verbindungen nach Anspruch 1 oder 2 mit η = 4. dehydriert werden.8. Verfahren nach Anspruch 71 dadurch gekennzeichnet, daßdie Dehydrierung in Gegenwart eines Edelmetallkatalysators, vorzugsweise in Gegenwart von Palladium, bei erhöhter
Temperatur durchgeführt wix*d.9. Verfahren nach Anspruch 7 oder 8, dadurch gekennzeichnet, daß in Anwesenheit von Schwefel, vorzugsweise in Anwesenheit von Diphenylsulfid und Alkalicarbonat, vorzugsweise Natriumcarbonat, dehydriert wird.809851/083310. Verfahren nach einem der Ansprüche 7 his 9» dadurch gekennzeichnet, daß ein Phenoläther durch Dehydrierung von 2-Cyclohexanoläther hergestellt wird.11, Verfahren nach einem der Ansprüche 7 bis 10, dadurch gekennzeichnet, daß zur Herstellung von Isopropoxiphenol 2-Isopropoxicyclöhexanol dehydriert wird.809851 /0833
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2392677 | 1977-06-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2824976A1 true DE2824976A1 (de) | 1978-12-21 |
DE2824976C2 DE2824976C2 (de) | 1983-12-29 |
Family
ID=10203547
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2858002A Expired DE2858002C2 (de) | 1977-06-08 | 1978-06-07 | Verfahren zur Herstellung von ortho-Alkoxyphenolen |
DE2824976A Expired DE2824976C2 (de) | 1977-06-08 | 1978-06-07 | Verfahren zur Herstellung von Cycloalkanoläthern |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2858002A Expired DE2858002C2 (de) | 1977-06-08 | 1978-06-07 | Verfahren zur Herstellung von ortho-Alkoxyphenolen |
Country Status (5)
Country | Link |
---|---|
US (1) | US4241225A (de) |
JP (1) | JPS543042A (de) |
DE (2) | DE2858002C2 (de) |
IL (1) | IL54869A0 (de) |
IT (1) | IT1105132B (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0279436A1 (de) * | 1987-02-19 | 1988-08-24 | BASF Aktiengesellschaft | 3-tert.-Butyl-4-methoxi-cyclohexylmethanol, dessen Herstellung und Verwendung als Riechstoff |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59215242A (ja) * | 1983-05-23 | 1984-12-05 | Nippon Kokan Keishiyu Kk | 鋳物砂の再生方法 |
JPS60216950A (ja) * | 1984-04-11 | 1985-10-30 | Nippon Kokan Keishiyu Kk | 鋳物砂の再生方法 |
US4918189A (en) * | 1986-12-12 | 1990-04-17 | Ciba-Geigy Corporation | Substituted hydroxylamines and compositions stabilized therewith |
EP0374445A1 (de) * | 1988-12-23 | 1990-06-27 | Firmenich Sa | Cyclische sauerstoffhaltige Verbindungen, ihre Verwendung als parfümierende Bestandteile, Verfahren für ihre Herstellung |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1464133A (en) | 1974-02-28 | 1977-02-09 | Laport Ind Ltd | Preparation of o-phenylphenol |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2812358A (en) * | 1957-11-05 | Production of half-ethers of cyclo- | ||
US2500016A (en) * | 1947-04-26 | 1950-03-07 | Canadian Ind | Epoxyethylcyclohexane hydroxy ethers |
LU53667A1 (de) * | 1966-07-26 | 1968-11-29 | ||
USRE29200E (en) | 1972-05-08 | 1977-05-03 | Cpc International Inc. | Production of alkoxy phenolic compounds |
USRE29201E (en) | 1972-05-08 | 1977-05-03 | Cpc International Inc. | Production of alkoxy phenolic compounds |
-
1978
- 1978-06-06 IT IT49729/78A patent/IT1105132B/it active
- 1978-06-06 US US05/913,127 patent/US4241225A/en not_active Expired - Lifetime
- 1978-06-07 IL IL7854869A patent/IL54869A0/xx unknown
- 1978-06-07 DE DE2858002A patent/DE2858002C2/de not_active Expired
- 1978-06-07 DE DE2824976A patent/DE2824976C2/de not_active Expired
- 1978-06-08 JP JP7028378A patent/JPS543042A/ja active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1464133A (en) | 1974-02-28 | 1977-02-09 | Laport Ind Ltd | Preparation of o-phenylphenol |
Non-Patent Citations (4)
Title |
---|
Beilstein: Handbuch der organ. Chemie, 4. Aufl., 1967, Bd. 6, 3. Ergänzungswerk, S. 4062-63 * |
Chemical Abstracts, 81, 1974, 25252u |
Collect.Czech.Chem.Commun., 1974, 39, 9, S. 2470-2475 * |
Römpp: Chemie-Lexikon, 7. Aufl., 1972, S. 385 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0279436A1 (de) * | 1987-02-19 | 1988-08-24 | BASF Aktiengesellschaft | 3-tert.-Butyl-4-methoxi-cyclohexylmethanol, dessen Herstellung und Verwendung als Riechstoff |
US4956341A (en) * | 1987-02-19 | 1990-09-11 | Basf Aktiengesellschaft | 3-tert-butyl-40-methoxycyclohexylmethanol, its preparation and its use as a scent |
Also Published As
Publication number | Publication date |
---|---|
DE2858002C2 (de) | 1985-01-17 |
IT1105132B (it) | 1985-10-28 |
JPS543042A (en) | 1979-01-11 |
US4241225A (en) | 1980-12-23 |
IL54869A0 (en) | 1978-08-31 |
DE2824976C2 (de) | 1983-12-29 |
IT7849729A0 (it) | 1978-06-06 |
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Owner name: COALITE GROUP PLC, BOLSOVER CHESTERFIELD, DERBYSHI |
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8128 | New person/name/address of the agent |
Representative=s name: MUELLER, H., DIPL.-ING., 8000 MUENCHEN SCHUPFNER, |
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8125 | Change of the main classification |
Ipc: C07C 43/196 |
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8126 | Change of the secondary classification |
Ipc: C07C 41/03 |
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8364 | No opposition during term of opposition | ||
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