DE1233861B - Verfahren zur Herstellung von Cycloalkylarylketonen - Google Patents
Verfahren zur Herstellung von CycloalkylarylketonenInfo
- Publication number
- DE1233861B DE1233861B DES90341A DES0090341A DE1233861B DE 1233861 B DE1233861 B DE 1233861B DE S90341 A DES90341 A DE S90341A DE S0090341 A DES0090341 A DE S0090341A DE 1233861 B DE1233861 B DE 1233861B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- found
- elemental analysis
- extracts
- total content
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 18
- -1 cycloalkylaryl ketones Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 239000000284 extract Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 238000000921 elemental analysis Methods 0.000 claims description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000012259 ether extract Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 6
- 238000000862 absorption spectrum Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- 238000005292 vacuum distillation Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- URAXDCBRCGSGAT-UHFFFAOYSA-N cyclooctanecarboxylic acid Chemical compound OC(=O)C1CCCCCCC1 URAXDCBRCGSGAT-UHFFFAOYSA-N 0.000 claims description 2
- 238000012552 review Methods 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- JWIPDQOXAJMVHL-UHFFFAOYSA-N cyclododecanecarboxylic acid Chemical compound OC(=O)C1CCCCCCCCCCC1 JWIPDQOXAJMVHL-UHFFFAOYSA-N 0.000 claims 2
- NZAGEGWEJZOHNU-UHFFFAOYSA-N cyclooctyl-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1CCCCCCC1 NZAGEGWEJZOHNU-UHFFFAOYSA-N 0.000 claims 2
- ROCIWIQPHIBTOC-JHSNUBCISA-N 3-[(2e,4e,6e)-4,8-dimethylnona-2,4,6-trienyl]furan Chemical compound CC(C)\C=C\C=C(/C)\C=C\CC=1C=COC=1 ROCIWIQPHIBTOC-JHSNUBCISA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- KEAJJDPQXMGWQK-UHFFFAOYSA-N cyclohexyl-(2,4-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC=C1C(=O)C1CCCCC1 KEAJJDPQXMGWQK-UHFFFAOYSA-N 0.000 claims 1
- WQYCAPDZCNPCMA-UHFFFAOYSA-N cyclohexyl-(4-propan-2-ylphenyl)methanone Chemical compound C1=CC(C(C)C)=CC=C1C(=O)C1CCCCC1 WQYCAPDZCNPCMA-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- NFZZBMGYMUGQBI-UHFFFAOYSA-N cyclohexyl-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1CCCCC1 NFZZBMGYMUGQBI-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 3
- DIXWFRFVEACSLS-UHFFFAOYSA-N cyclohexyl-(2,5-dimethylphenyl)methanone Chemical compound CC1=CC=C(C)C(C(=O)C2CCCCC2)=C1 DIXWFRFVEACSLS-UHFFFAOYSA-N 0.000 description 3
- QGBBABKHNMOQTA-UHFFFAOYSA-N cyclohexyl-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)C1CCCCC1 QGBBABKHNMOQTA-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- BMFYCFSWWDXEPB-UHFFFAOYSA-N cyclohexyl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1 BMFYCFSWWDXEPB-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT726663 | 1963-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1233861B true DE1233861B (de) | 1967-02-09 |
Family
ID=11124932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES90341A Pending DE1233861B (de) | 1963-04-06 | 1964-04-02 | Verfahren zur Herstellung von Cycloalkylarylketonen |
Country Status (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10439437B2 (en) | 2003-02-04 | 2019-10-08 | Philips Ip Ventures B.V. | Adaptive inductive power supply with communication |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3262581D1 (en) * | 1981-02-04 | 1985-04-25 | Ici Plc | Production of hydroxy arylophenones |
| DE4240965A1 (de) * | 1992-12-05 | 1994-06-09 | Basf Ag | Verfahren zur Herstellung von Acylaromaten |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE633124A (fr) * | 1962-05-07 | 1963-12-02 | Snia Viscosa | Procédé pour la préparation de la cyclohexylphényl-cétone |
-
1964
- 1964-04-02 DE DES90341A patent/DE1233861B/de active Pending
- 1964-04-02 DK DK164764A patent/DK109773C/da active
- 1964-04-02 NL NL6403530A patent/NL6403530A/xx unknown
- 1964-04-03 GB GB1381564A patent/GB1066542A/en not_active Expired
- 1964-04-06 CH CH430764A patent/CH443278A/de unknown
- 1964-04-06 ES ES298755A patent/ES298755A1/es not_active Expired
- 1964-04-06 BE BE646179A patent/BE646179A/xx unknown
- 1964-04-06 SE SE422264A patent/SE316169B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE633124A (fr) * | 1962-05-07 | 1963-12-02 | Snia Viscosa | Procédé pour la préparation de la cyclohexylphényl-cétone |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10439437B2 (en) | 2003-02-04 | 2019-10-08 | Philips Ip Ventures B.V. | Adaptive inductive power supply with communication |
Also Published As
| Publication number | Publication date |
|---|---|
| ES298755A1 (es) | 1964-12-01 |
| DK109773C (da) | 1968-07-01 |
| BE646179A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-07-31 |
| NL6403530A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-10-07 |
| CH443278A (de) | 1967-09-15 |
| SE316169B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-10-20 |
| GB1066542A (en) | 1967-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE19522876C1 (de) | Verfahren zur Herstellung eines DOP-haltigen Gemisches und dessen Verwendung | |
| EP2949646A1 (de) | Verfahren zur herstellung von 2,2'-selenobiarylethern oder 4,4'-selenobiarylethern unter verwendung von selendioxid | |
| DE1695753B2 (de) | Verfahren zur Herstellung von 6,6disubstituierten 2,2-Dimethyl-4-oxopiperidinen | |
| DE2355690C2 (de) | Verfahren zur Herstellung von Phenol oder substituierten Phenolen | |
| DE1233861B (de) | Verfahren zur Herstellung von Cycloalkylarylketonen | |
| DE3125329A1 (de) | Verfahren zur herstellung von derivaten der vinylphosphon- oder vinylpyrophosphonsaeure | |
| DE2919974A1 (de) | Verfahren zur herstellung von cyanhydrinacylaten von aldehyden | |
| AT247864B (de) | Verfahren zur Herstellung von Cycloalkyl-arylketonen | |
| EP0130439B1 (de) | Verfahren zur Herstellung von Derivaten der Vinylphosphon-, oder Vinylpyrophosphonsäure | |
| DE1957860A1 (de) | Verfahren zur Herstellung von 2,3-Dihydro-p-dithiinen und deren Sulfoxiden und Sulfonen | |
| EP0062305B1 (de) | Verfahren zur Herstellung von 5-Oxohexansäure | |
| DE1194852B (de) | Verfahren zur Herstellung von Phosphonsaeuren oder deren Salzen mit mindestens zwei Phosphoratomen im Molekuel | |
| DE2413824C2 (de) | Verfahren zur Herstellung von tertiären (Hydroxymehtyl)-methylphosphinoxiden | |
| EP0018540B1 (de) | Ester des Isocamphyl-guajakols, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von 3-(Iso-camphyl-(5))-cyclohexanol | |
| DE1024091B (de) | Verfahren zur Herstellung phosphorhaltiger heterocyclischer Verbindungen | |
| DE871449C (de) | Verfahren zur Herstellung des Pentaerythrit-dichlorhydrin-monoschwefligsaeureesters | |
| DE69806513T2 (de) | Herstellung von phosphonsäurederivaten | |
| EP0003553B1 (de) | Verfahren zur Herstellung von O,S-Dialkylthiophosphorsäurechloriden | |
| DE810028C (de) | Verfahren zur Herstellung von Phenyl-1-aethanolamin-2 | |
| DE965490C (de) | Verfahren zur Herstellung von aromatischen Sulfoniumverbindungen | |
| DE947370C (de) | Verfahren zur Herstellung von 4-Thionylamino-2-oxy-benzoylchlorid | |
| DE2114219C3 (de) | Verfahren zur Herstellung von 2,3-Dihydrofluoranthen aus Fluoranthen | |
| DE1668966C (de) | Verfahren zur gleichzeitigen Herstellung von 2,6-Dimethyl-phenol und 4-tert-Butylphenol | |
| DE1931946C3 (de) | Verfahren zur Herstellung von 1 -Hydroxymethyl-1.2.3.4-tetrahydrofluoranthen | |
| DE2031430A1 (en) | Substd anthraquinones prepn - using phosphorus cpd in ring closure |