DE2732830C2 - Process for the preparation of a product containing m-isocamphylphenol by catalytic isomerization of p-isocamphylphenol or a mixture containing p-isocamphylphenol - Google Patents
Process for the preparation of a product containing m-isocamphylphenol by catalytic isomerization of p-isocamphylphenol or a mixture containing p-isocamphylphenolInfo
- Publication number
- DE2732830C2 DE2732830C2 DE2732830A DE2732830A DE2732830C2 DE 2732830 C2 DE2732830 C2 DE 2732830C2 DE 2732830 A DE2732830 A DE 2732830A DE 2732830 A DE2732830 A DE 2732830A DE 2732830 C2 DE2732830 C2 DE 2732830C2
- Authority
- DE
- Germany
- Prior art keywords
- isocamphylphenol
- phenol
- mixture
- hydrogen fluoride
- isomerization
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- 238000006317 isomerization reaction Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000003197 catalytic effect Effects 0.000 title claims 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 claims description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 12
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 12
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 claims description 9
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims description 9
- 229930006739 camphene Natural products 0.000 claims description 9
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 Polyethylene Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 241000221035 Santalaceae Species 0.000 description 2
- 235000008632 Santalum album Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BWVZAZPLUTUBKD-UHFFFAOYSA-N 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol Chemical compound CC1(C)C(C)C2CC1CC2C1CCCC(O)C1 BWVZAZPLUTUBKD-UHFFFAOYSA-N 0.000 description 1
- PCFHYANYPQEMPU-UHFFFAOYSA-N 4-(2,2,3-trimethyl-5-bicyclo[2.2.1]heptanyl)cyclohexan-1-ol Chemical class CC1(C)C(C)C2CC1CC2C1CCC(O)CC1 PCFHYANYPQEMPU-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
- C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
m-Isocamphy]phenol ist ein wichtiges Zwischenprodukt zur Herstellung von S-Isocamphylcyclohexanol, das ein chemischer Aromastoff mit dem Geruch von Sandelholz istm-Isocamphy] phenol is an important intermediate for the production of S-Isocamphylcyclohexanol, the is a chemical flavoring with the smell of sandalwood
Es ist bekannt, daß bei der Umsetzung von Phenol mit Camphen in Gegenwart eines Friedel-Crafts-Katalysators hauptsächlich p-Isocamphylphenol entsteht Dieses Isomere ist jedoch von geringem Interesse, da das entsprechende 4-Isocamphylcyclohexanol keine Aroma-Eigenschaften hat.It is known that when phenol is reacted with camphene in the presence of a Friedel-Crafts catalyst mainly p-isocamphylphenol is formed.However, this isomer is of little interest because the corresponding 4-isocamphylcyclohexanol has no flavor properties.
In der US-PS 39 20 758 wird vorgeschlagen, p-Isocamphylphenol durch Isomerisierung in Gegenwart eines Aluminiumchlorid-Katalysators in ein das m-Isomere enthaltendes Produkt umzuwandeln. Es werden jedoch keine Angaben über den Umwandlungsgrad gemachtIn US-PS 39 20 758 it is proposed, p-Isocamphylphenol by isomerization in the presence of a To convert aluminum chloride catalyst into a product containing the m-isomer. It will, however no information was given about the degree of conversion
Aufgabe der Erfindung war es daher, ein neues Isomerisierungsverfahren zur Herstellung eines Produkts, das relativ viel m-Isocamphylphenol enthält, zur Verfügung zu stellen.The object of the invention was therefore to provide a new isomerization process for the production of a product which contains a relatively large amount of m-isocamphylphenol.
Dieses technische Problem wird erfindungsgemäß dadurch gelöst, daß man die Isomerisierung von p-Isocamphylphenol oder eines p-Isocamphylphenol enthaltenden Gemisches bei Temperaturen von 0 bis 120°C in Gegenwart von wasserfreiem Fluorwasserstoff durchführtAccording to the invention, this technical problem is solved by the isomerization of p-isocamphylphenol or a mixture containing p-isocamphylphenol at temperatures from 0 to 120 ° C in In the presence of anhydrous hydrogen fluoride
Als Ausgangsmaterial für das erfindungsgemäße Verfahren wird bevorzugt ein Gemisch eingesetzt, das p-Isocamphylphenol und mindestens ein anderes Isocamphylphenol-Isomeres enthält Derartige Gemische sind leicht erhältlich, ein geeignetes Verfahren für ihre Herstellung ist die Umsetzung von Camphen mit Phenol.The starting material used for the process according to the invention is preferably a mixture which p-Isocamphylphenol and at least one other isocamphylphenol isomer. Such mixtures are easily available, a suitable method for their production is the reaction of camphene with phenol.
Vorzugsweise wird ein p-Isocamphylphenol enthaltendes Gemisch isomerisiert, das durch Umsetzen von Camphen mit Phenol in Gegenwart von wasserfreiem Fluorwasserstoff erhalten worden ist.A mixture containing p-isocamphylphenol is preferably isomerized, which is obtained by reacting Camphene has been obtained with phenol in the presence of anhydrous hydrogen fluoride.
Somit bietet das erfindungsgemäße Verfahren die Möglichkeit, das gewünschte m-Isocamphylphenol enthaltende Produkt in einer einzigen Stufe aus Camphen und Phenol herzustellen.The process according to the invention thus offers the possibility of containing the desired m-isocamphylphenol Manufacture product from camphene and phenol in a single step.
Die erfindungsgemäße Isomerisierung des p-Isocamphylphenols oder des p-Isocamphylphenol enthaltenden Gemisches mit wasserfreiem Fluorwasserstoff erfolgt vorzugsweise im Temperaturbereich von 60 bis 800C. Die Isomerisierung wird dabei zweckmäßigerweise in Gegenwart eines 10- bis 60fachen molaren Überschusses an Fluorwasserstoff, bezogen auf p-Isocamphylphenol, durchgeführt.The isomerization of the p-Isocamphylphenols invention or the p-Isocamphylphenol containing mixture with anhydrous hydrogen fluoride is preferably carried out in the temperature range of 60 to 80 0 C. The isomerization is expediently in the presence of a 10- to 60-fold molar excess of hydrogen fluoride, based on p-Isocamphylphenol , carried out.
Auch bei der Herstellung des p-Isocamphylphenol enthaltenden Gemisches durch Umsetzen von Camphen und Phenol in Gegenwart von wasserfreiem Fluorwasserstoff werden die gleichen Reaktionsbedingungen angewendet, d. h. Temperaturen von 0 bis 1200C, vorzugsweise 60 bis 800C. Der Fluorwasserstoff wird dabei in einem 10- bis 40fachen Überschuß, bezogen auf das Phenol, eingesetzt. Auch das Phenol wird vorzugsweise im Überschuß eingesetzt, z. B. in einem molaren Verhältnis von Phenol zu Camphen von 2 :1 bis 4 :1. Gegebenenfalls kann man bei der Umsetzung zusätzlich noch andere Fluoride einsetzen, z. B. Bortrifluorid, Antimonpentafluorid, Phosphorpentafluorid und Titantetrafluorid. In diesem Fall werden niedrigere Temperaturen bevorzugt, z. B. 20 bis 30° C.The same reaction conditions are also used in the preparation of the p-isocamphylphenol-containing mixture by reacting camphene and phenol in the presence of anhydrous hydrogen fluoride, ie temperatures from 0 to 120 ° C., preferably 60 to 80 ° C. The hydrogen fluoride is used in a 10 - Up to 40 times the excess, based on the phenol, used. The phenol is also preferably used in excess, e.g. B. in a molar ratio of phenol to camphene of 2: 1 to 4: 1. If necessary, you can also use other fluorides in the implementation, for. B. boron trifluoride, antimony pentafluoride, phosphorus pentafluoride and titanium tetrafluoride. In this case lower temperatures are preferred, e.g. B. 20 to 30 ° C.
Das im erfindungsgemäßen Verfahren erhaltene Produkt wird in üblicher Weise, z. B. durch katalytische Hydrierung, wie mit einem Edelmetall, z. B. Rhodium, als Katalysator, in ein Produkt umgewandelt, das 3-Isocamphylcyclohexanol enthält.The product obtained in the process according to the invention is conventionally used, for. B. by catalytic Hydrogenation, such as with a noble metal, e.g. B. rhodium, as a catalyst, converted into a product, the 3-isocamphylcyclohexanol contains.
0,1 Mol reines p-Isocamphylphenol wird in 100 ml wasserfreiem Fluorwasserstoff in einem Autoklaven aus0.1 mol of pure p-isocamphylphenol is dissolved in 100 ml of anhydrous hydrogen fluoride in an autoclave
rostfreiem Stahl gelöst. Die Lösung wird 4 Stunden auf 75° C erhitzt. Nach dem Abkühlen wird die Lösung unter Rühren in zerstoßenes Eis gegossen. Das wäßrige Gemisch wird mit festem Kaliumcarbonat neutralisiert und mit Diäthyläther extrahiert. Die Extrakte werden über Magnesiumsulfat getrocknet, das Lösungsmittel wird unter vermindertem Druck entfernt. Der Rückstand wird fraktioniert destilliert.stainless steel solved. The solution is heated to 75 ° C. for 4 hours. After cooling, the solution is taking Stir poured into crushed ice. The aqueous mixture is neutralized with solid potassium carbonate and extracted with diethyl ether. The extracts are dried over magnesium sulfate, the solvent becomes removed under reduced pressure. The residue is fractionally distilled.
0,1 Mol Camphen und 0,25 Mol Phenol werden unter Erwärmen zu einer farblosen Flüssigkeit vermischt, die dann unter Rühren und Abkühlen im Verlauf von 20 Minuten zu 100 ml wasserfreiem Fluorwasserstoff in einer Polyäthylen-Flasche gegeben wird. Das Gemisch wird in einen Autoklaven aus rostfreiem Stahl (Hastelloy® C) übergeführt und 6 Stunden auf 75° C erhitzt. Die abgekühlte Lösung wird unter Rühren in zerstoßenes Eis gegossen. Das wäßrige Gemisch wird mit festem Kaliumcarbonat neutralisiert und mit Diäthyläther extrahiert.0.1 mol of camphene and 0.25 mol of phenol are mixed with heating to form a colorless liquid which then with stirring and cooling in the course of 20 minutes to 100 ml of anhydrous hydrogen fluoride in a Polyethylene bottle is given. The mixture is placed in a stainless steel autoclave (Hastelloy® C) transferred and heated to 75 ° C for 6 hours. The cooled solution is poured into crushed ice while stirring poured. The aqueous mixture is neutralized with solid potassium carbonate and extracted with diethyl ether.
Die Ätherextrakte werden über Magnesiumsulfat getrocknet, das Lösungsmittel wird unter vermindertem Druck entfernt Der Rückstand wird fraktioniert destilliert, man erhält ein Produkt mit einem Kp. von 160 bis 163°C/266,66 Pa, das die o-, m- und p-Isomere des Isocamphylphenols in den in der Tabelle angegebenen Mengen enthält Die Anteile an jedem Isomeren in dem Produkt werden durch Gas-Flüssigchromatographie bestimmtThe ether extracts are dried over magnesium sulfate, the solvent is reduced under reduced pressure Pressure removed. The residue is fractionally distilled, giving a product with a boiling point of 160 bis 163 ° C / 266.66 Pa, which is the o-, m- and p-isomers of isocamphylphenol in the specified in the table Amounts contains The proportions of each isomer in the product are determined by gas-liquid chromatography certainly
Beispiel 3 bis 7
Die Arbeitsweise des Beispiels 2 wird wiederholt, mit dem Unterschied, daßExample 3 to 7
The procedure of Example 2 is repeated with the difference that
a) in den Beispielen 3 und 6 nach dem Neutralisieren mit festem Kaliumcarbonat das Reaktionsgemisch mit 6gewichtsprozentiger Kalilauge behandelt wird,a) in Examples 3 and 6, after neutralization with solid potassium carbonate, the reaction mixture with 6 weight percent potassium hydroxide solution is treated,
b) in Beispiel 4 die Ausgangsverbindungen und der Fluorwasserstoff direkt im Autoklaven vermischt werden,b) in example 4 the starting compounds and the hydrogen fluoride are mixed directly in the autoclave,
c) in den Beispielen 5 bis 7 die Umsetzung in Polyäthylen-Flaschen erfolgt,c) in Examples 5 to 7 the reaction takes place in polyethylene bottles,
d) in den Beispielen 6 und 7 die Umsetzung in Gegenwart von 6 g bzw. 8 g Bortrifluoricä durchgeführt wird.d) in Examples 6 and 7, the reaction is carried out in the presence of 6 g and 8 g of boron trifluorica, respectively.
Die Ergebnisse sind in der Tabelle zusammengefaßt
TabelleThe results are summarized in the table
Tabel
IsomeresIsomer
%%
Das gemäß Beispiel 2 erhaltene Isomerengemisch wird bei 120° C und einem Druck von 100 bar in Gegenwart eines Katalysators, der aus 5% Rhodium auf Kohle besteht, hydriert. Man erhält ein farbloses viskoses öl, das den Geruch von Sandelholz hat und das 2-, 3- und 4-Isomere des Isocamphylcyclohexanols enthält.The isomer mixture obtained according to Example 2 is at 120 ° C and a pressure of 100 bar in the presence a catalyst consisting of 5% rhodium on carbon, hydrogenated. A colorless viscous oil is obtained which has the smell of sandalwood and contains the 2-, 3- and 4-isomers of isocamphylcyclohexanol.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30540/76A GB1526580A (en) | 1976-07-22 | 1976-07-22 | Preparation of a phenol derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2732830A1 DE2732830A1 (en) | 1978-01-26 |
| DE2732830C2 true DE2732830C2 (en) | 1986-05-22 |
Family
ID=10309252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2732830A Expired DE2732830C2 (en) | 1976-07-22 | 1977-07-20 | Process for the preparation of a product containing m-isocamphylphenol by catalytic isomerization of p-isocamphylphenol or a mixture containing p-isocamphylphenol |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5312848A (en) |
| CH (1) | CH635811A5 (en) |
| DE (1) | DE2732830C2 (en) |
| FR (1) | FR2359108A1 (en) |
| GB (1) | GB1526580A (en) |
| NL (1) | NL7708060A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7809557A (en) * | 1978-09-20 | 1980-03-24 | Shell Int Research | PARA-C10-TERPENYLBENZOIC ACID AND ITS SALTS, ESTERS AND ANHYDRIDES, THE PREPARATION OF THESE COMPOUNDS AND THEIR USE IN THE PREPARATION OF 3-C10-TERPE-NYLCYCLOHEXANOL. |
-
1976
- 1976-07-22 GB GB30540/76A patent/GB1526580A/en not_active Expired
-
1977
- 1977-07-20 JP JP8617177A patent/JPS5312848A/en active Pending
- 1977-07-20 CH CH902677A patent/CH635811A5/en not_active IP Right Cessation
- 1977-07-20 DE DE2732830A patent/DE2732830C2/en not_active Expired
- 1977-07-20 NL NL7708060A patent/NL7708060A/en not_active Application Discontinuation
- 1977-07-20 FR FR7722229A patent/FR2359108A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2359108A1 (en) | 1978-02-17 |
| DE2732830A1 (en) | 1978-01-26 |
| CH635811A5 (en) | 1983-04-29 |
| FR2359108B1 (en) | 1980-10-10 |
| GB1526580A (en) | 1978-09-27 |
| NL7708060A (en) | 1978-01-24 |
| JPS5312848A (en) | 1978-02-04 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DI |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |