CH513791A - Verfahren zur Herstellung von makrocyclischen Verbindungen - Google Patents

Verfahren zur Herstellung von makrocyclischen Verbindungen

Info

Publication number: CH513791A
Authority: CH; Switzerland
Prior art keywords: acid; diketone; mol; acidic; denotes
Prior art date: 1966-12-08

Application number

CH1298370A

Other languages

German (de)

English (en)

Inventor

J Becker Joseph

Karl-Heinrich Dr Schulte-Elte

Guenther Dr Ohloff

Original Assignee

Firmenich & Cie

Priority date (The priority date 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 date listed.)

1966-12-08

Filing date

1966-12-08

Publication date

1971-10-15

1966-12-08 Application filed by Firmenich & Cie filed Critical Firmenich & Cie

1966-12-08 Priority to CH288971A priority Critical patent/CH519456A/de

1966-12-08 Priority to CH289171A priority patent/CH519454A/de

1966-12-08 Priority to CH289271A priority patent/CH519457A/de

1966-12-08 Priority to CH1298370A priority patent/CH513791A/de

1966-12-08 Priority to CH289071A priority patent/CH519450A/de

1966-12-08 Priority claimed from CH1751966A external-priority patent/CH503680A/de

1971-10-15 Publication of CH513791A publication Critical patent/CH513791A/de

Links

150000002576 ketones Chemical class 0.000 title claims abstract 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract 2
125000005594 diketone group Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000012445 acidic reagent Substances 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 claims description 2
239000007868 Raney catalyst Substances 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
239000004327 boric acid Substances 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 2
235000019797 dipotassium phosphate Nutrition 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
229910000510 noble metal Inorganic materials 0.000 claims description 2
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 2
229910000343 potassium bisulfate Inorganic materials 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
ALHUZKCOMYUFRB-UHFFFAOYSA-N 3-methylcyclopentadecan-1-one Chemical compound CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 abstract 2
OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 abstract 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
VZAZWURAKYCTAG-UHFFFAOYSA-N cyclopentadecane-1,2-dione Chemical compound O=C1CCCCCCCCCCCCCC1=O VZAZWURAKYCTAG-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
150000002678 macrocyclic compounds Chemical class 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
150000007659 semicarbazones Chemical class 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
NOYWIORCHYSXFW-UHFFFAOYSA-N 2,3,5,6,7,8,9,10,11,12,13,13a-dodecahydro-1H-cyclopenta[12]annulene Chemical compound C1CC=C2C(CCCCCCC1)CCC2 NOYWIORCHYSXFW-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
-1 aromatic sulfonic acids Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
238000010992 reflux Methods 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension 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
- C07C45/61—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
- C07C45/64—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 introduction of functional groups containing oxygen only in singly bound form
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrane Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Fats And Perfumes (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CH1298370A 1966-02-08 1966-12-08 Verfahren zur Herstellung von makrocyclischen Verbindungen CH513791A (de)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CH288971A CH519456A (de)	1966-12-08	1966-12-08	Verfahren zur Herstellung von bicyclischen ungesättigten Ketonen
CH289171A CH519454A (de)	1966-02-08	1966-12-08	Verfahren zur Herstellung von makrocyclischen Verbindungen
CH289271A CH519457A (de)	1966-12-08	1966-12-08	Verfahren zur Herstellung von makrocyclischen Verbindungen
CH1298370A CH513791A (de)	1966-12-08	1966-12-08	Verfahren zur Herstellung von makrocyclischen Verbindungen
CH289071A CH519450A (de)	1966-12-08	1966-12-08	Verfahren zur Herstellung von makrocyclischen Verbindungen

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1751966A CH503680A (de)	1966-12-08	1966-12-08	Verfahren zur Herstellung von makrocyclischen Ketonen
CH1298370A CH513791A (de)	1966-12-08	1966-12-08	Verfahren zur Herstellung von makrocyclischen Verbindungen

Publications (1)

Publication Number	Publication Date
CH513791A true CH513791A (de)	1971-10-15

Family

ID=4426068

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1298370A CH513791A (de)	1966-02-08	1966-12-08	Verfahren zur Herstellung von makrocyclischen Verbindungen

Country Status (3)

Country	Link
JP (5)	JPS5129148B1 (fr)
CH (1)	CH513791A (fr)
ES (1)	ES348564A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2016184948A1 (fr)	2015-05-20	2016-11-24	Basf Se	Procédé de préparation de dicétone macrocyclique
WO2016193330A1 (fr)	2015-06-03	2016-12-08	Basf Se	Procédé de préparation de 3-méthylcyclopentadécane-1,5-dione
EP3170828A1 (fr)	2015-11-23	2017-05-24	Basf Se	Procede de preparation de composes a squelette de 16-oxabicycloo[10.3.1]pentadecen et leurs produits secondaires
WO2018011386A1 (fr)	2016-07-15	2018-01-18	Basf Se	Préparation de 14-méthyl-16-oxabicyclo [10.3.1] pentadeènes à partir de 3-méthyl -1,5-cyclopentadécanedione

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2012045786A1 (fr) *	2010-10-07	2012-04-12	Basf Se	Procédé de production de cétones, en particulier de cétones macrocycliques
CN107001214B (zh) *	2014-12-26	2021-03-23	花王株式会社	环状二酮化合物的制造方法
JP7738514B2 (ja) *	2022-03-31	2025-09-12	花王株式会社	環状ジケトン化合物の製造方法
JP7707121B2 (ja)	2022-03-31	2025-07-14	花王株式会社	環状ジケトン化合物の製造方法

1966
- 1966-12-08 CH CH1298370A patent/CH513791A/de not_active IP Right Cessation
1967
- 1967-12-07 ES ES348564A patent/ES348564A1/es not_active Expired
1970
- 1970-12-29 JP JP12198670A patent/JPS5129148B1/ja active Pending
- 1970-12-29 JP JP12198370A patent/JPS5133904B1/ja active Pending
- 1970-12-29 JP JP12198270A patent/JPS5124498B1/ja active Pending
- 1970-12-29 JP JP12198170A patent/JPS5129147B1/ja active Pending
- 1970-12-29 JP JP12198470A patent/JPS494459B1/ja active Pending

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2016184948A1 (fr)	2015-05-20	2016-11-24	Basf Se	Procédé de préparation de dicétone macrocyclique
US10053410B2 (en)	2015-05-20	2018-08-21	Basf Se	Process for preparing a macrocyclic diketone
WO2016193330A1 (fr)	2015-06-03	2016-12-08	Basf Se	Procédé de préparation de 3-méthylcyclopentadécane-1,5-dione
EP3170828A1 (fr)	2015-11-23	2017-05-24	Basf Se	Procede de preparation de composes a squelette de 16-oxabicycloo[10.3.1]pentadecen et leurs produits secondaires
US10259822B2 (en)	2015-11-23	2019-04-16	Basf Se	Method for the preparation of compounds having a 16-oxabicyclo[10.3.1]pentadecene scaffold and the subsequent products thereof
WO2018011386A1 (fr)	2016-07-15	2018-01-18	Basf Se	Préparation de 14-méthyl-16-oxabicyclo [10.3.1] pentadeènes à partir de 3-méthyl -1,5-cyclopentadécanedione
US10800724B2 (en)	2016-07-15	2020-10-13	Basf Se	Preparation of 14-methyl-16-oxabicyclo[10.3.1]pentadecenes from 3-methyl-1,5-cyclopentadecanedione

Also Published As

Publication number	Publication date
ES348564A1 (es)	1969-06-16
JPS494459B1 (fr)	1974-02-01
JPS5133904B1 (fr)	1976-09-22
JPS5124498B1 (fr)	1976-07-24
JPS5129147B1 (fr)	1976-08-24
JPS5129148B1 (fr)	1976-08-24

Legal Events

Date	Code	Title	Description
1978-08-31	PL	Patent ceased

Publication	Publication Date	Title
DE1793801C2 (de)	1978-05-24	Verfahren zur Herstellung von makrocyclischen Verbindungen
DE1617006A1 (de)	1970-12-10	Riechstoffkompositionen
CH513791A (de)	1971-10-15	Verfahren zur Herstellung von makrocyclischen Verbindungen
DE2516696C3 (de)	1979-09-13	Riechstoffe der 3,6,6-Trimethyll-(but-3-enoyl)-cyclohexenreihe, Verfahren zu deren Herstellung und diese enthaltende Riechstoffkompositionen
DE3703585A1 (de)	1988-08-18	Alkohole und ether mit cyclododecyl- und cyclododecenylgruppen, deren herstellung und verwendung als duftstoffe
DE3122995C2 (fr)	1991-08-14
CH625494A5 (fr)	1981-09-30
EP0043507A2 (fr)	1982-01-13	2,4-Dioxa-7,10-méthano-spiro(5,5)undécannes et leur préparation, de même que des compositions de parfums les contenant
DE2640026C2 (de)	1985-07-25	Verfahren zur Herstellung von 6,10,14-Trimethylpentadecan-2-on
DE2313017C3 (de)	1980-03-20	Cyclopentene und Verfahren zu deren Herstellung
CH637612A5 (en)	1983-08-15	Substituted cyclohexanes
EP0150290B1 (fr)	1987-04-01	Procédé pour la préparation d'oxa-13 bicyclo[10.3.0]-pentadécane
DE2150337A1 (de)	1972-05-25	1-Alkenyl-9-10-anthrachinone und Verfahren zu deren Herstellung
CH307629A (de)	1955-06-15	Verfahren zur Herstellung eines monosubstituierten Hydrazins.
DE1802121A1 (de)	1969-06-19	Riechstoffkompositionen
CH625495A5 (fr)	1981-09-30
DE3020298C2 (de)	1983-04-28	Verfahren zur Herstellung von 2,2,4,5,5-Pentamethyl-3-formyl-3-pyrrolin
AT217050B (de)	1961-09-11	Verfahren zur Herstellung von Isozeaxanthin-dialkyläthern
AT203474B (de)	1959-05-25	Verfahren zur Herstellung von α,β-ungesättigten Aldehyden
DE1668265C (de)		alpha,3,3 Trimethylcyclohexylmethanol, dessen niedere Alkansaureester bzw 3,3 Dimethylcyclohexylmethylketon sowie Ver fahren zu deren Herstellung
AT217441B (de)	1961-10-10	Verfahren zur Herstellung von Hexadecadien-(10,12)-ol-(1)
EP0026344A1 (fr)	1981-04-08	Cétones et alcools alicycliques substitués par du triméthylcyclopentène-3-méthyl, procédé de préparation et leur utilisation comme matières odorantes
DE2314697B2 (de)	1975-04-10	1 -Amino^-hydroxy-SJ-dimethyloctane und Verfahren zu deren Herstellung
AT264726B (de)	1968-09-10	Verfahren zur Herstellung von Verbindungen der Vitamin A-Reihe
DE946442C (de)	1956-08-02	Verfahren zur Herstellung von Kondensationsprodukten aus Phthalsaeureanhydriden und hydroaromatischen Kohlenwasserstoffen