CH662344A5 - Verfahren zur herstellung von 2-(1-hydroxyalkyl)-cyclohexanon und/oder 2-alkyliden-cyclohexanon. - Google Patents
Verfahren zur herstellung von 2-(1-hydroxyalkyl)-cyclohexanon und/oder 2-alkyliden-cyclohexanon. Download PDFInfo
- Publication number
- CH662344A5 CH662344A5 CH4643/84A CH464384A CH662344A5 CH 662344 A5 CH662344 A5 CH 662344A5 CH 4643/84 A CH4643/84 A CH 4643/84A CH 464384 A CH464384 A CH 464384A CH 662344 A5 CH662344 A5 CH 662344A5
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclohexanone
- reaction
- hydroxyalkyl
- aldehyde
- alkylidene
- Prior art date
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title description 111
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 description 62
- -1 aliphatic aldehyde Chemical class 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 22
- 239000008346 aqueous phase Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 19
- 239000012071 phase Substances 0.000 description 17
- 239000002585 base Substances 0.000 description 14
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical group CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 12
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 8
- 238000006482 condensation reaction Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- WVANVZNUDWLCTQ-UHFFFAOYSA-N 2-(2-methylpropylidene)cyclohexan-1-one Chemical compound CC(C)C=C1CCCCC1=O WVANVZNUDWLCTQ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005882 aldol condensation reaction Methods 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MYSLPKPAMDRDGE-TWGQIWQCSA-N (2z)-2-butylidenecyclohexan-1-one Chemical compound CCC\C=C1\CCCCC1=O MYSLPKPAMDRDGE-TWGQIWQCSA-N 0.000 description 2
- BATWHICBOTVWLT-UHFFFAOYSA-N 2-(1-hydroxybutyl)cyclohexan-1-one Chemical compound CCCC(O)C1CCCCC1=O BATWHICBOTVWLT-UHFFFAOYSA-N 0.000 description 2
- MYSLPKPAMDRDGE-UHFFFAOYSA-N 2-butylidenecyclohexan-1-one Chemical compound CCCC=C1CCCCC1=O MYSLPKPAMDRDGE-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- YPRIHWWNQRSAQL-UQCOIBPSSA-N (2z)-2-ethylidenecyclohexan-1-one Chemical compound C\C=C1\CCCCC1=O YPRIHWWNQRSAQL-UQCOIBPSSA-N 0.000 description 1
- NFRZRQPRVZCVLO-UHFFFAOYSA-N 2,6-bis(2-methylpropylidene)cyclohexan-1-one Chemical compound CC(C)C=C1CCCC(=CC(C)C)C1=O NFRZRQPRVZCVLO-UHFFFAOYSA-N 0.000 description 1
- UYLDCDSQFKWOBN-UHFFFAOYSA-N 2,6-di(butylidene)cyclohexan-1-one Chemical compound CCCC=C1CCCC(=CCCC)C1=O UYLDCDSQFKWOBN-UHFFFAOYSA-N 0.000 description 1
- FHZKOZKYUQDWBE-UHFFFAOYSA-N 2-(1-hydroxy-2-methylpropyl)cyclohexan-1-one Chemical compound CC(C)C(O)C1CCCCC1=O FHZKOZKYUQDWBE-UHFFFAOYSA-N 0.000 description 1
- JPVZXEQZCYRRNC-UHFFFAOYSA-N 2-(1-hydroxyethyl)cyclohexan-1-one Chemical compound CC(O)C1CCCCC1=O JPVZXEQZCYRRNC-UHFFFAOYSA-N 0.000 description 1
- RFFJGNBKNOWRDB-UHFFFAOYSA-N 2-(1-hydroxypropyl)cyclohexan-1-one Chemical compound CCC(O)C1CCCCC1=O RFFJGNBKNOWRDB-UHFFFAOYSA-N 0.000 description 1
- KONLWCATLTVPNH-UHFFFAOYSA-N 2-(2-ethyl-1-hydroxybutyl)cyclohexan-1-one Chemical compound CCC(CC)C(O)C1CCCCC1=O KONLWCATLTVPNH-UHFFFAOYSA-N 0.000 description 1
- TZLYHTNSBQIYQA-UHFFFAOYSA-N 2-(2-ethylbutylidene)cyclohexan-1-one Chemical compound CCC(CC)C=C1CCCCC1=O TZLYHTNSBQIYQA-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- ZRJUCHNILNOEKV-UHFFFAOYSA-N hexan-2-one hydrate Chemical compound O.CCCCC(C)=O ZRJUCHNILNOEKV-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58179986A JPS6072840A (ja) | 1983-09-28 | 1983-09-28 | ２−アルキリデンシクロヘキサノンの製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH662344A5 true CH662344A5 (de) | 1987-09-30 |
Family
ID=16075453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4643/84A CH662344A5 (de) | 1983-09-28 | 1984-09-27 | Verfahren zur herstellung von 2-(1-hydroxyalkyl)-cyclohexanon und/oder 2-alkyliden-cyclohexanon. |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4668827A (enExample) |
| JP (1) | JPS6072840A (enExample) |
| CH (1) | CH662344A5 (enExample) |
| DE (1) | DE3435003C2 (enExample) |
| GB (1) | GB2146995B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3707209A1 (de) * | 1987-03-06 | 1988-09-15 | Henkel Kgaa | 2-alkyliden-3,3,5(3,5,5)-trimethylcyclopentanone als riechstoffe |
| DE10046434A1 (de) * | 2000-09-20 | 2002-04-04 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von verzweigten Alkoholen und/oder Kohlenwasserstoffen |
| US7161041B2 (en) | 2002-12-26 | 2007-01-09 | Kao Corporation | Process for producing cycloalkanone derivatives |
| JP4651959B2 (ja) * | 2004-03-15 | 2011-03-16 | 花王株式会社 | シクロアルカノン類含有組成物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519327A (en) * | 1947-01-13 | 1950-08-15 | Fmc Corp | Condensation of beta-(4-methyl-delta3-cyclohexenyl)-butyraldehyde with aldehydes andketones |
| US3942761A (en) * | 1971-01-04 | 1976-03-09 | Monsanto Company | 4-(2'-Norbornyl)-2-butanones |
-
1983
- 1983-09-28 JP JP58179986A patent/JPS6072840A/ja active Granted
-
1984
- 1984-09-24 DE DE3435003A patent/DE3435003C2/de not_active Expired - Fee Related
- 1984-09-27 GB GB08424418A patent/GB2146995B/en not_active Expired
- 1984-09-27 CH CH4643/84A patent/CH662344A5/de not_active IP Right Cessation
-
1986
- 1986-02-04 US US06/825,787 patent/US4668827A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2146995A (en) | 1985-05-01 |
| DE3435003C2 (de) | 1995-05-24 |
| GB8424418D0 (en) | 1984-10-31 |
| US4668827A (en) | 1987-05-26 |
| JPH0125732B2 (enExample) | 1989-05-19 |
| DE3435003A1 (de) | 1985-04-04 |
| GB2146995B (en) | 1986-12-10 |
| JPS6072840A (ja) | 1985-04-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: MITSUBISHI KASEI CORPORATION |
|
| PL | Patent ceased |