AT92778B - Process for the preparation of new esters of adipic acid. - Google Patents
Process for the preparation of new esters of adipic acid.Info
- Publication number
- AT92778B AT92778B AT92778DA AT92778B AT 92778 B AT92778 B AT 92778B AT 92778D A AT92778D A AT 92778DA AT 92778 B AT92778 B AT 92778B
- Authority
- AT
- Austria
- Prior art keywords
- adipic acid
- preparation
- new esters
- ester
- esters
- Prior art date
Links
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims description 16
- 150000002148 esters Chemical class 0.000 title claims description 15
- 239000001361 adipic acid Substances 0.000 title claims description 8
- 235000011037 adipic acid Nutrition 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- -1 aliphatic alcohols Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XMOUOZUUJHDLSN-UHFFFAOYSA-N 6-oxo-6-pentoxyhexanoic acid Chemical compound CCCCCOC(=O)CCCCC(O)=O XMOUOZUUJHDLSN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940031578 diisopropyl adipate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung neuer Ester der Adipinsäure.
Ester der Adipinsäure mit den einfachen, aliphatischen Alkoholen, z. B. Methylalkohol, Äthylalkohol usw., sind bekannt und können nach einer der gebräuchlichen Esterifizierungsmethoden dargestellt werden. Dagegen sind bisher Ester dieser Säure mit Alkoholen höherer Kohlenstoffzahl, wie z. B. Amyl-oder Isopropylalkohol, noch nicht dargestellt worden.
Es wurde nun gefunden, dass Adipinsäureamylester und-isopropylester überraschender Weise in hohem Masse die Fähigkeit haben, Nitrozellulose zu gelatinieren, wodurch sie für die Herstellung von Zelluloid und Films besonders wertvoll sind. Ausserdem haben die genannten Ester die Eigenschaft,
EMI1.1
anstriche zu erteilen. Infolge dieser beiden Eigenschaften stellen die genannten Ester neue Produkte von hohem technischen Werte dar.
Zu ihrer Herstellung behandelt man nach an sich bekannten Methoden ein Gemisch von Adipinsäure und dem betreffenden Alkohol mit einer Mineralsäure und scheidet aus dem Reaktionsgemenge den Ester ab.
Beispiel l : Adipinsäureamylester. Man kocht 100 Teile Adipinsäure mit 145 Teilen Amylalkohol, bis alles in Lösung gegangen ist. In die abgekühlte Lösung leitet man Salzsäure bis zur Sättigung ein.
Nach 24 stündigem Stehen wird wiederum mit Salzsaure gesättigt, nach Verdünnen mit Wasser mit Soda gewaschen, um vom gleichzeitig sich bildenden, sauren Ester zu trennen. Nach Abdestillieren des überschüssigen Amylalkohols erhält man durch Destillation den reinen Ester in nahezu quantitativer Ausbeute. Der Siedepunkt des Esters beträgt 309 bei 742 mm, das spezifische Gewicht 0'945 bei 20 .
Der Ester stellt eine farblose, angenehm riechende Flüssigkeit dar.
Beispiel 2 : Adipinsäurediisopropylester. Man kocht 100 Teile Adipinsäure mit 120 Teilen Isopropylalkohol unter Zugabe von 20 Teilen konzentrierter Schwefelsäure acht Stunden am Rückfluss- kühler. Die weitere Aufarbeitung geschieht in der Weise, dass das Reaktionsgemisch in Eiswasser gegossen, im Scheidetrichter geschieden, der Ester zuerst in einer schwachen Sodalösung und dann mit Wasser neutral gewaschen und im Vakuum destilliert wird. Der Siedepunkt des Esters beträgt 2570 bei 743 mm, das spezifische Gewicht 0'977 bei 20 . Der Ester stellt eine farblose, angenehm riechende Flüssigkeit dar.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of new esters of adipic acid.
Esters of adipic acid with the simple, aliphatic alcohols, e.g. B. methyl alcohol, ethyl alcohol, etc., are known and can be prepared by one of the common esterification methods. In contrast, esters of this acid with alcohols with a higher carbon number, such as. B. amyl or isopropyl alcohol, not yet shown.
It has now been found that amyl adipate and isopropyl ester surprisingly have a high degree of ability to gelatinize nitrocellulose, which makes them particularly valuable for the production of celluloid and films. In addition, the esters mentioned have the property
EMI1.1
to paint. As a result of these two properties, the esters mentioned represent new products of high technical value.
To prepare them, a mixture of adipic acid and the alcohol in question is treated with a mineral acid by methods known per se and the ester is separated from the reaction mixture.
Example 1: amyl adipate. 100 parts of adipic acid are boiled with 145 parts of amyl alcohol until everything has dissolved. Hydrochloric acid is passed into the cooled solution until it is saturated.
After standing for 24 hours, it is again saturated with hydrochloric acid and, after dilution with water, washed with soda in order to separate from the acidic ester that is formed at the same time. After the excess amyl alcohol has been distilled off, the pure ester is obtained in almost quantitative yield by distillation. The boiling point of the ester is 309 at 742 mm, the specific gravity 0.945 at 20.
The ester is a colorless, pleasantly smelling liquid.
Example 2: Diisopropyl adipate. 100 parts of adipic acid are boiled with 120 parts of isopropyl alcohol with the addition of 20 parts of concentrated sulfuric acid for eight hours on a reflux condenser. The further work-up is done in such a way that the reaction mixture is poured into ice water, separated in a separating funnel, the ester is first washed neutral in a weak soda solution and then with water and distilled in vacuo. The boiling point of the ester is 2570 at 743 mm, the specific gravity 0.977 at 20. The ester is a colorless, pleasantly smelling liquid.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT92778T | 1921-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT92778B true AT92778B (en) | 1923-05-25 |
Family
ID=3612757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT92778D AT92778B (en) | 1921-06-20 | 1921-06-20 | Process for the preparation of new esters of adipic acid. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT92778B (en) |
-
1921
- 1921-06-20 AT AT92778D patent/AT92778B/en active
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