AT243779B - Process for the preparation of 7-cyclohexylheptanol- (1) and 7-cyclohexylheptanediol- (1,4) - Google Patents
Process for the preparation of 7-cyclohexylheptanol- (1) and 7-cyclohexylheptanediol- (1,4)Info
- Publication number
- AT243779B AT243779B AT821063A AT821063A AT243779B AT 243779 B AT243779 B AT 243779B AT 821063 A AT821063 A AT 821063A AT 821063 A AT821063 A AT 821063A AT 243779 B AT243779 B AT 243779B
- Authority
- AT
- Austria
- Prior art keywords
- cyclohexylheptanol
- cyclohexylheptanediol
- preparation
- cyclohexylpropyl
- butyrolactone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- -1 γ-cyclohexylpropyl-γ-butyrolactone Chemical compound 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von 7-Cyclohexylheptanol- (l) und 7-Cyclohexylheptandiöl- (l, 4)
Die Erfindung betrifft ein Verfahren zur Herstellung eines trennbaren Gemisches von 7-Cyclohexylheptanol-(1) und 7-Cyclohexylheptandiol-(1,4) durch hydrierende Aufspaltung des Lactonringes von y-Cyclohexylpropyl-y-butyrolacton.
Es ist bekannt, dass y-und 6-Lactone sich durch Hydrierung mit Kupferchromitkatalysatoren nach Adkins in zwei Richtungen spalten lassen. Man erhält, je nach der Richtung, in der die C-O-C Bindung hydrierend gesprengt wird, einen zweiwertigen und einen einwertigen Alkohol, welche als Gemisch anfallen.
Es wurde nun gefunden, dass y-Cyclohexylpropyl-y-butyrolacton, gelöst in Dioxan, durch Hydrierung in Gegenwart von 20 bis 25 Gew.-% Kupferchromithydrierungskatalysatoren bei Temperaturen von 240 bis 250 C, vorzugsweise 250 C, und Drücken von 230 bis 260 atü, vorzugsweise 250 atü, in an sich bekannter Weise unter Aufspaltung des Lactonringes zu Alkoholen der nachstehend aufgeführten Formel führt :
EMI1.1
Das erfindungsgemäss als Ausgangsstoff einzusetzende y-Cyclohexylpropyl-y-butyrolacton kann beispielsweise durch Hydrierung von [5-Phenylfuryl-(2)]-propionsäureester bei 2500C und 260 at in Gegenwart von Raney-Nickel hergestellt werden.
Die erfindungsgemäss hergestellten Alkohole können beispielsweise als Lösungs- und Verschnittmittel sowie als Veresterungskomponente in der Polyester- und Weichmacherindustr e verwendet werden.
Beispiel : 150 g y-Cyclohexylpropyl-y-butyrolacton werden in Dioxan gelöst und mit 40 g Kupferchromitkontakt bei 2500C und 250 atü im Schüttelautoklaven hydriert. Nach Abdestillation des Lösungsmittels erhält man durch fraktionierende Destillation 60 g 7-Cyclohexylheptanol- (1) vom Kpl 120-121 C und 57 g 7-Cyclohexylheptandiol- (l, 4) vom Kp1 160-1620C.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the production of 7-cyclohexylheptanol- (l) and 7-cyclohexylheptanediöl- (l, 4)
The invention relates to a process for the production of a separable mixture of 7-cyclohexylheptanol- (1) and 7-cyclohexylheptanediol- (1,4) by hydrogenative splitting of the lactone ring of γ-cyclohexylpropyl-γ-butyrolactone.
It is known that γ- and 6-lactones can be split in two directions by hydrogenation using Adkins copper chromite catalysts. Depending on the direction in which the C-O-C bond is hydrogenatedly broken, a dihydric and a monohydric alcohol are obtained, which are obtained as a mixture.
It has now been found that γ-cyclohexylpropyl-γ-butyrolactone, dissolved in dioxane, by hydrogenation in the presence of 20 to 25% by weight of copper chromite hydrogenation catalysts at temperatures of 240 to 250 ° C., preferably 250 ° C., and pressures of 230 to 260 atmospheres , preferably 250 atm, leads in a known manner with splitting of the lactone ring to alcohols of the following formula
EMI1.1
The γ-cyclohexylpropyl-γ-butyrolactone to be used as a starting material according to the invention can be prepared, for example, by hydrogenation of [5-phenylfuryl- (2)] propionic acid ester at 2500 ° C. and 260 atm in the presence of Raney nickel.
The alcohols prepared according to the invention can be used, for example, as solvents and co-solvents and as esterification components in the polyester and plasticizer industries.
Example: 150 g of γ-cyclohexylpropyl-γ-butyrolactone are dissolved in dioxane and hydrogenated with 40 g of copper chromite contact at 2500 ° C. and 250 atm. In a shaking autoclave. After distilling off the solvent, fractional distillation gives 60 g of 7-cyclohexylheptanol- (1) of Kpl 120-121 C and 57 g of 7-cyclohexylheptanediol- (1,4) of bp 160-1620C.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE243779X | 1963-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT243779B true AT243779B (en) | 1965-11-25 |
Family
ID=5922554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT821063A AT243779B (en) | 1963-03-29 | 1963-10-14 | Process for the preparation of 7-cyclohexylheptanol- (1) and 7-cyclohexylheptanediol- (1,4) |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT243779B (en) |
-
1963
- 1963-10-14 AT AT821063A patent/AT243779B/en active
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