CH405289A - Verfahren zur Herstellung von Oxymethylcyclododecan - Google Patents
Verfahren zur Herstellung von OxymethylcyclododecanInfo
- Publication number
- CH405289A CH405289A CH59562A CH59562A CH405289A CH 405289 A CH405289 A CH 405289A CH 59562 A CH59562 A CH 59562A CH 59562 A CH59562 A CH 59562A CH 405289 A CH405289 A CH 405289A
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- hydrogen
- dependent
- solvent
- monooxymethylcyclododecane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- KIYUNVUWDQKWPJ-UHFFFAOYSA-N cyclododecanecarbaldehyde Chemical compound O=CC1CCCCCCCCCCC1 KIYUNVUWDQKWPJ-UHFFFAOYSA-N 0.000 claims description 8
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical class C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- -1 aliphatic alcohols Chemical class 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 4
- 150000001868 cobalt Chemical class 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000007037 hydroformylation reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229940011182 cobalt acetate Drugs 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000005671 trienes Chemical class 0.000 description 2
- MWMODOXJCVGXML-UHFFFAOYSA-N 3-methylnonane-2,2-diol Chemical compound CCCCCCC(C)C(C)(O)O MWMODOXJCVGXML-UHFFFAOYSA-N 0.000 description 1
- MWTPBEVCVOHWSX-UHFFFAOYSA-N 6-methylhepta-2,4-diene Chemical compound CC=CC=CC(C)C MWTPBEVCVOHWSX-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- JWIPDQOXAJMVHL-UHFFFAOYSA-N cyclododecanecarboxylic acid Chemical compound OC(=O)C1CCCCCCCCCCC1 JWIPDQOXAJMVHL-UHFFFAOYSA-N 0.000 description 1
- KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009183 running Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/13—Monohydroxylic alcohols containing saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
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)
- Passenger Equipment (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL287930D NL287930A (en:Method) | 1962-01-18 | ||
| CH59562A CH405289A (de) | 1962-01-18 | 1962-01-18 | Verfahren zur Herstellung von Oxymethylcyclododecan |
| CH1200662A CH428715A (de) | 1962-01-18 | 1962-10-12 | Verfahren zur Herstellung von Monooxymethylcyclooctan |
| US251000A US3342878A (en) | 1962-01-18 | 1963-01-14 | Preparation of monohydroxymethylcyclododecane by hydroformylation of cyclododecatrienes |
| DE19631468065 DE1468065A1 (de) | 1962-01-18 | 1963-01-15 | Verfahren zur Herstellung eines hauptsaechlich Monooxymethylcyclododecan enthaltenden Gemisches von Cyclododecanderivaten |
| NO147140A NO116911B (en:Method) | 1962-01-18 | 1963-01-16 | |
| ES284218A ES284218A1 (es) | 1962-01-18 | 1963-01-16 | Procedimiento para la obtención de una mezcla de derivados de ciclododecano |
| DK19863AA DK103509C (da) | 1962-01-18 | 1963-01-16 | Fremgangsmåde til fremstilling af monooxymethylcyclododecan ud fra cyclododecatrien. |
| SE526/63A SE314975B (en:Method) | 1962-01-18 | 1963-01-17 | |
| GB2162/63A GB1003578A (en) | 1962-01-18 | 1963-01-17 | Process for the manufacture of hydroxymethylcyclododecane |
| BE627228A BE627228A (fr) | 1962-01-18 | 1963-01-17 | Procédé de préparation d'oxyméthyl-cyclododécane |
| FI630081A FI40006C (fi) | 1962-01-18 | 1963-01-17 | Sätt att framställa monooximetylcyklododekan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH59562A CH405289A (de) | 1962-01-18 | 1962-01-18 | Verfahren zur Herstellung von Oxymethylcyclododecan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH405289A true CH405289A (de) | 1966-01-15 |
Family
ID=4190622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH59562A CH405289A (de) | 1962-01-18 | 1962-01-18 | Verfahren zur Herstellung von Oxymethylcyclododecan |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3342878A (en:Method) |
| BE (1) | BE627228A (en:Method) |
| CH (1) | CH405289A (en:Method) |
| DE (1) | DE1468065A1 (en:Method) |
| DK (1) | DK103509C (en:Method) |
| ES (1) | ES284218A1 (en:Method) |
| FI (1) | FI40006C (en:Method) |
| GB (1) | GB1003578A (en:Method) |
| NL (1) | NL287930A (en:Method) |
| NO (1) | NO116911B (en:Method) |
| SE (1) | SE314975B (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH468320A (de) * | 1966-08-17 | 1969-02-15 | Inventa Ag | Verfahren zur Herstellung eines Gemisches von Formylcyclododecan und Cyclododecen |
| DE2838755A1 (de) * | 1978-09-06 | 1980-03-27 | Bayer Ag | Aminomethyl-cyclododecane, ein verfahren zu ihrer herstellung und ihre verwendung als korrosionsschutzmittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB861979A (en) * | 1957-10-24 | 1961-03-01 | Studiengesellschaft Kohle Mbh | A process for the production of cyclododecane derivatives |
| US3089904A (en) * | 1959-03-02 | 1963-05-14 | Exxon Research Engineering Co | Oxonation of 1, 5, 9-cyclododecatriene |
-
0
- NL NL287930D patent/NL287930A/xx unknown
-
1962
- 1962-01-18 CH CH59562A patent/CH405289A/de unknown
-
1963
- 1963-01-14 US US251000A patent/US3342878A/en not_active Expired - Lifetime
- 1963-01-15 DE DE19631468065 patent/DE1468065A1/de not_active Withdrawn
- 1963-01-16 DK DK19863AA patent/DK103509C/da active
- 1963-01-16 ES ES284218A patent/ES284218A1/es not_active Expired
- 1963-01-16 NO NO147140A patent/NO116911B/no unknown
- 1963-01-17 GB GB2162/63A patent/GB1003578A/en not_active Expired
- 1963-01-17 SE SE526/63A patent/SE314975B/xx unknown
- 1963-01-17 BE BE627228A patent/BE627228A/fr unknown
- 1963-01-17 FI FI630081A patent/FI40006C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| NO116911B (en:Method) | 1969-06-09 |
| NL287930A (en:Method) | |
| SE314975B (en:Method) | 1969-09-22 |
| DE1468065A1 (de) | 1969-02-06 |
| GB1003578A (en) | 1965-09-08 |
| US3342878A (en) | 1967-09-19 |
| FI40006C (fi) | 1968-09-10 |
| ES284218A1 (es) | 1963-04-01 |
| DK103509C (da) | 1966-01-17 |
| FI40006B (en:Method) | 1968-05-31 |
| BE627228A (fr) | 1963-05-16 |
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