CA1095088A - Procede d'obtention de cyclohexanedione-(1,4)- tetramethyl dicetals - Google Patents

Procede d'obtention de cyclohexanedione-(1,4)- tetramethyl dicetals

Info

Publication number: CA1095088A
Authority: CA; Canada
Prior art keywords: cyclohexanedione; diketal; tetramethyl; preparation; methanol
Prior art date: 1977-01-26
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.): Expired

Application number

CA344,251A

Other languages

English (en)

Inventor

Elmar Konz

Rudolf Pistorius

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst 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.)

1977-01-26

Filing date

1980-01-23

Publication date

1981-02-03

1977-01-26 Priority claimed from DE19772703077 external-priority patent/DE2703077A1/de

1980-01-23 Application filed by Hoechst AG filed Critical Hoechst AG

1980-01-23 Priority to CA344,251A priority Critical patent/CA1095088A/fr

1981-02-03 Application granted granted Critical

1981-02-03 Publication of CA1095088A publication Critical patent/CA1095088A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 7
230000008569 process Effects 0.000 title claims description 6
OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 claims abstract description 23
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 5
230000003197 catalytic effect Effects 0.000 claims abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
239000003054 catalyst Substances 0.000 claims description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
239000011261 inert gas Substances 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
239000000975 dye Substances 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
239000001257 hydrogen Substances 0.000 description 13
229910052739 hydrogen Inorganic materials 0.000 description 13
238000005984 hydrogenation reaction Methods 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000002904 solvent Substances 0.000 description 6
AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002184 metal Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
-1 cyclohexylami~ne Chemical compound 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
229940077445 dimethyl ether Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000004065 semiconductor Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000001052 yellow pigment Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA344,251A 1977-01-26 1980-01-23 Procede d'obtention de cyclohexanedione-(1,4)- tetramethyl dicetals Expired CA1095088A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA344,251A CA1095088A (fr)	1977-01-26	1980-01-23	Procede d'obtention de cyclohexanedione-(1,4)- tetramethyl dicetals

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DEP2703077.9		1977-01-26
DE19772703077 DE2703077A1 (de)	1977-01-26	1977-01-26	Verfahren zur herstellung von cyclohexandion-(1,4)-tetramethyl- diketal
CA295,619A CA1089492A (fr)	1977-01-26	1978-01-25	Preparation de cyclohexanedione-(1,4)-tetramethyl- dicetal
CA344,251A CA1095088A (fr)	1977-01-26	1980-01-23	Procede d'obtention de cyclohexanedione-(1,4)- tetramethyl dicetals

Publications (1)

Publication Number	Publication Date
CA1095088A true CA1095088A (fr)	1981-02-03

Family

ID=27165481

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA344,251A Expired CA1095088A (fr)	1977-01-26	1980-01-23	Procede d'obtention de cyclohexanedione-(1,4)- tetramethyl dicetals

Country Status (1)

Country	Link
CA (1)	CA1095088A (fr)

1980
- 1980-01-23 CA CA344,251A patent/CA1095088A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-02-03	MKEX	Expiry

Publication	Publication Date	Title
FI89906C (fi)	1993-12-10	Foerfarande foer framstaellning av aminocyanacetamid
CA1095088A (fr)	1981-02-03	Procede d'obtention de cyclohexanedione-(1,4)- tetramethyl dicetals
US4161614A (en)	1979-07-17	Process for the preparation of cyclohexane dione-(1,4)-tetramethyl diketal
US4480107A (en)	1984-10-30	Pyranic derivatives useful as intermediates in making muscone
US3205264A (en)	1965-09-07	Process for the preparation of 10, 11-dihydro-5-(gamma-methyl-and dimethyl-amino propylidene)-5h-dibenzo[a, d] cycloheptene
US4204076A (en)	1980-05-20	Hydroquinone dimethyl ether
US4528385A (en)	1985-07-09	Method of preparing phthalide
JPS5858334B2 (ja)	1983-12-24	レゾルシンノセイホウ
US3914291A (en)	1975-10-21	Process for splitting cycloaliphatic hydroperoxides
Reed et al.	1989	The Mercury (II) Catalyzed, One-Pot Oxidation of Terminal Alkynes by Sodium Perborate in Acetic Acid
Koerner et al.	1991	Anthracenediols as reactive dienes in base-catalyzed cycloadditions: reduction-cycloaddition reactions of anthraquinones
CA1093586A (fr)	1981-01-13	Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyldicetals
EP0057975B1 (fr)	1985-08-14	Procédé de production de polycondensats de l'acide oméga-oxypentadécanoique
US4910343A (en)	1990-03-20	Nitroamines
CA1065900A (fr)	1979-11-06	Procede pour la fabrication d'ethers dimethyliques de l'hydroquinone
JPH0250101B2 (fr)	1990-11-01
HU207706B (en)	1993-05-28	Process for producing alpha-omega-diacids
US3349106A (en)	1967-10-24	Solvent for obtaining very high yields of aldehydic products from soybean oil
JPH032162A (ja)	1991-01-08	ピペリジンカルボン酸類の製造方法
JPH03236372A (ja)	1991-10-22	Ｎ―置換ピロリジン―２―オンの製法
CA1095089A (fr)	1981-02-03	Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyl dicetals
US5218129A (en)	1993-06-08	Process for producing 3,4-dihydrocoumarin
JP2009513503A (ja)	2009-04-02	化粧有効成分の製造方法
EP0003409B1 (fr)	1981-11-25	Procédé pour la préparation de l'acide 4-amino-méthylbicyclo(2,2,2)octane-1-carboxylique et un composé intermédiaire y relatif
AT353775B (de)	1979-12-10	Verfahren zur herstellung von hydrochinon- dimethylaether