DD202140A5 - Verfahren zur herstellung von dimedon - Google Patents

Verfahren zur herstellung von dimedon Download PDF

Info

Publication number: DD202140A5
Authority: DD; German Democratic Republic
Prior art keywords: ester; ozone; dimedone; isophorone; dimethyl
Prior art date: 1981-05-27

Application number

DD82240120A

Other languages

German (de)

English (en)

Inventor

Pavel Lehky

Original Assignee

Lonza Ag

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.)

1981-05-27

Filing date

1982-05-24

Publication date

1983-08-31

1982-05-24 Application filed by Lonza Ag filed Critical Lonza Ag

1983-08-31 Publication of DD202140A5 publication Critical patent/DD202140A5/de

Links

BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 title claims abstract description 24
238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims abstract description 38
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 16
150000002148 esters Chemical class 0.000 claims abstract description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
239000002904 solvent Substances 0.000 claims abstract description 11
SLBXWQKHHZUDAY-UHFFFAOYSA-N 3,3-dimethyl-5-oxohexanoic acid Chemical compound CC(=O)CC(C)(C)CC(O)=O SLBXWQKHHZUDAY-UHFFFAOYSA-N 0.000 claims abstract description 9
230000015572 biosynthetic process Effects 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims abstract description 6
150000007513 acids Chemical class 0.000 claims abstract description 3
238000009825 accumulation Methods 0.000 claims description 6
238000005949 ozonolysis reaction Methods 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 abstract description 3
239000000047 product Substances 0.000 abstract 3
239000003513 alkali Substances 0.000 abstract 1
239000013067 intermediate product Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 4
WHUYLFCBWGXUTJ-UHFFFAOYSA-N methyl 3,3-dimethyl-5-oxohexanoate Chemical compound COC(=O)CC(C)(C)CC(C)=O WHUYLFCBWGXUTJ-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
238000006136 alcoholysis reaction Methods 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
238000003918 potentiometric titration Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
-1 3,3-dimethyl-5-oxo-hexane ester Chemical class 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
WQYBQHLAONTIRY-UHFFFAOYSA-N ethyl 3,3-dimethyl-5-oxohexanoate Chemical compound CCOC(=O)CC(C)(C)CC(C)=O WQYBQHLAONTIRY-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000010805 inorganic waste Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000000052 vinegar 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
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Jellies, Jams, And Syrups (AREA)

DD82240120A 1981-05-27 1982-05-24 Verfahren zur herstellung von dimedon DD202140A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH3473/81A CH653665A5 (de)	1981-05-27	1981-05-27	Verfahren zur herstellung von dimedon.

Publications (1)

Publication Number	Publication Date
DD202140A5 true DD202140A5 (de)	1983-08-31

Family

ID=4256724

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82240120A DD202140A5 (de)	1981-05-27	1982-05-24	Verfahren zur herstellung von dimedon

Country Status (11)

Country	Link
US (1)	US4414418A (fr)
EP (1)	EP0065707B1 (fr)
JP (1)	JPS57200324A (fr)
AT (1)	ATE12763T1 (fr)
CA (1)	CA1219002A (fr)
CH (1)	CH653665A5 (fr)
DD (1)	DD202140A5 (fr)
DE (1)	DE3263090D1 (fr)
DK (1)	DK236882A (fr)
HU (1)	HU190389B (fr)
IL (1)	IL65822A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4628117A (en) *	1983-02-07	1986-12-09	National Distillers And Chemical Corporation	Process for the ozonization of α,β-unsaturated cyclohexanones to 5-ketoalkanoic acids
DE3806835A1 (de) *	1988-03-03	1989-09-14	Huels Chemische Werke Ag	Verfahren zur herstellung von 3,5,5-trimethyl-4-hydroxi-2-cyclohexen-1-on
JPH04247052A (ja) *	1991-01-31	1992-09-03	Nippon Soda Co Ltd	ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法
US7983822B2 (en)	2006-09-05	2011-07-19	GM Global Technology Operations LLC	Dual wire internal mode switch assembly

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2917537A (en) *		1959-12-15		Its esters
US2944899A (en) *	1956-10-04	1960-07-12	Eastman Kodak Co	Stabilization of photographic silver halide emulsions
NL122308C (fr) *	1963-04-26
GB1327154A (en)	1971-01-15	1973-08-15	American Cyanamid Co	Dioxocyclohexenecarboxanilide insecticides and acaricides
US3823164A (en) *	1971-08-26	1974-07-09	American Home Prod	5,6,7,8-tetrahydro-2,5(and 4,5)-dioxo-1-benzopyrans
US3775435A (en) *	1971-08-26	1973-11-27	American Home Prod	5,6,7,8-tetrahydro-2,5(and 4,5)-dioxo-1-benzopyrans
DE2245270C3 (de) *	1972-09-15	1979-09-13	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Cyclohexandionen-0,3)
NL174940C (nl) *	1973-03-14	1984-09-03	Stamicarbon	Werkwijze voor de bereiding van cyclohexaan-1,3-dion en alkylgesubstitueerde derivaten hiervan.
US3976785A (en) *	1973-11-02	1976-08-24	American Cyanamid Company	Dioxocyclohexanecarboxanilide insecticides and acaricides
CA1056282A (fr)	1974-03-25	1979-06-12	Charles T. Goodhue	Elements multicouches pour le dosage du cholesterol
DE2533919C3 (de) *	1975-07-30	1980-09-18	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von CyclohexandioneM 1.3)
DE2533920C2 (de) *	1975-07-30	1982-12-09	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Resorcinen

1981
- 1981-05-27 CH CH3473/81A patent/CH653665A5/de not_active IP Right Cessation
1982
- 1982-05-12 DE DE8282104156T patent/DE3263090D1/de not_active Expired
- 1982-05-12 AT AT82104156T patent/ATE12763T1/de not_active IP Right Cessation
- 1982-05-12 EP EP82104156A patent/EP0065707B1/fr not_active Expired
- 1982-05-19 IL IL65822A patent/IL65822A/xx not_active IP Right Cessation
- 1982-05-19 US US06/379,718 patent/US4414418A/en not_active Expired - Fee Related
- 1982-05-24 DD DD82240120A patent/DD202140A5/de unknown
- 1982-05-26 CA CA000403805A patent/CA1219002A/fr not_active Expired
- 1982-05-26 DK DK236882A patent/DK236882A/da not_active Application Discontinuation
- 1982-05-27 HU HU821715A patent/HU190389B/hu unknown
- 1982-05-27 JP JP57088948A patent/JPS57200324A/ja active Pending

Also Published As

Publication number	Publication date
HU190389B (en)	1986-08-28
US4414418A (en)	1983-11-08
CH653665A5 (de)	1986-01-15
DK236882A (da)	1982-11-28
JPS57200324A (en)	1982-12-08
EP0065707B1 (fr)	1985-04-17
IL65822A0 (en)	1982-08-31
DE3263090D1 (en)	1985-05-23
EP0065707A3 (en)	1983-01-26
IL65822A (en)	1985-08-30
EP0065707A2 (fr)	1982-12-01
ATE12763T1 (de)	1985-05-15
CA1219002A (fr)	1987-03-10

Publication	Publication Date	Title
DE3010195C2 (fr)	1990-10-25
EP0415214B1 (fr)	1994-02-02	Procédé pour la fabrication de dérivés de l'acide alpha-fluoroacrylique
DD202140A5 (de)	1983-08-31	Verfahren zur herstellung von dimedon
DE2404160C3 (de)	1981-05-21	Verfahren zur Herstellung von 2-(4-Alkylphenyl)-propionsäuren
CH619206A5 (fr)	1980-09-15
DE69515053T2 (de)	2000-08-03	Verfahren zur herstellung von furosemide
DE2950608C2 (fr)	1990-09-13
DE2533396C2 (de)	1986-08-28	3-Methyl-3-aryl-brenztraubensäureester und Verfahren zu ihrer Herstellung
DE2404159C2 (de)	1982-04-22	Verfahren zur Herstellung von 2-(4-Alkylphenyl)-propionsäuren und ihren Natrium-oder Kaliumsalzen
DE2352922A1 (de)	1974-04-25	Verfahren zur herstellung von perchlormethylmercaptan
EP0166214B1 (fr)	1989-07-26	Procédé de préparation de succinylsuccinate de dialkyl
EP0064634B1 (fr)	1984-07-25	Procédé de préparation de l'acide 3,3-diméthylglutarique
EP0056615B1 (fr)	1984-06-13	Procédé de préparation de la carnitinamide
EP0065708A2 (fr)	1982-12-01	Procédé de préparation de la dimédone
EP0342482B1 (fr)	1994-08-03	Procédé de préparation de dérivés de pyrimidine
EP0024682B1 (fr)	1982-12-22	Procédé de préparation de n-propyl-n-propylidène-acétamide ou de di-n-propyl-acétamide
EP0103749B1 (fr)	1986-07-02	Dialcoxyméthyl-butyrolactones, procédé et intermédiaires pour leur préparation et leur utilisation
EP0065706A1 (fr)	1982-12-01	Procédé pour préparer l'acide 3,3-diméthylglutarique ou ses esters
CH655300A5 (de)	1986-04-15	Verfahren zur herstellung von dihalogen-vinyl-cyclopropancarbonsaeuren.
CH323464A (de)	1957-07-31	Verfahren zur Herstellung eines basischen Esters der 9-Xantencarbonsäure
CH498075A (de)	1970-10-31	Verfahren zur Herstellung von neuen, substituierten Aryloxyessigsäuren und ihren Salzen
DE1141988B (de)	1963-01-03	Verfahren zur Herstellung von 2, 3, 5-Tricarboxycyclopentylessigsaeure
DE2107405A1 (de)	1971-09-02	Verfahren zur Herstellung von 5 Nitro lmidazoldenvaten
CH348407A (de)	1960-08-31	Verfahren zur Herstellung von 3-Phenyl-3-alkyl-2-pyrrolidonen
DE3700764A1 (de)	1987-07-23	Verfahren zur herstellung von 2,5-dichlor-3-fluorpyridin