CH236384A - Process for the preparation of an ether carboxylic acid nitrile. - Google Patents
Process for the preparation of an ether carboxylic acid nitrile.Info
- Publication number
- CH236384A CH236384A CH236384DA CH236384A CH 236384 A CH236384 A CH 236384A CH 236384D A CH236384D A CH 236384DA CH 236384 A CH236384 A CH 236384A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- carboxylic acid
- acid nitrile
- ether carboxylic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 6
- -1 ether carboxylic acid nitrile Chemical class 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SFPQDYSOPQHZAQ-UHFFFAOYSA-N 2-methoxypropanenitrile Chemical compound COC(C)C#N SFPQDYSOPQHZAQ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Ätherearbonsä irenitrils. Es ist bekannt, d:ass sich Cyanwasserstoff mit gesättigten .aliphatischen Äthern, zum Beispiel Dim@ethyl- und Diäthyläther, in Ge genwart von wasserabspaltend wirkenden Ka talysatoren umsetzt, wobei unter Sprengung der Ätherbrücke Alkylnitrile entstehen.
Es wurde nun gefunden, dass man das be kannte a-Methoxypropionsäurenitril erhält. wenn man Methylvinyläther bei erhöhten Temperaturen mit Cyanwassers:tof fbehandelt.
Die Umsetzung lässt sich bereits bei 100 und darunter bewirken, jedoch wendet man zweckmässig höhere Temperaturen, zum Bei spiel solche von 150-300 oder ,darüber, an. Die Umsetzung lässt sich durch Zusatz von basischen Katalysatoren günstiger gestalten.
Als solche eignen sich beispielsweise basisch wirkende oder säurebindende Metallverbin dungen, vornehmlich Alkali- und Erdalkali- verbind@ungen, zum Beispiel Natrium- und Kaliumhydroxyd, Natrium- und Kaliumcy- anid oder Kupferhydroxyd, insbesondere aber auch organische Basen, wie Pyridin und Pyrrolidin, gegebenenfalls in Verbindung mit Schwermetallsalzen,
zum Beispiel Kup- fercyanid. Derartige Basen können gleich zeitig als Lösungsmittel bei der Umsetzung dienen. Auch andere Lösungsmittel, in denen sowohl der Methylvinyläther als auch Cyan wasserstoff löslich sind, können verwendet werden, zum Beispiel Tetrahyd@rofuran oder Dioxan.
Der Cyanwasserstoff wird zweckmässig in unverdünnter Form angewandt, "er kann aber auch inerte Verdünnungsgase oder -dämpfe enthalten. Die Umsetzung lässt sich diskontinuierlich gestalten oder auch im un unterbrochenen Betrieb bewirken, beispiels weise indem man eine Mischung der Aus gangsstoffe mit dem Katalysator und gege benenfalls einem Verdünnungsmittel durch ein Rohr leitet oder durch ein mit Füllkör pern beschicktes Gefäss rieseln lässt.
Arbeitet man in flüssiger Phase, so kann man den Druck über den dem Paxtial:druck des Um-
EMI0002.0001
setzunbsbemisches <SEP> entsprechenden <SEP> Druck <SEP> er höhen, <SEP> indem <SEP> man <SEP> ein <SEP> inertes <SEP> Gas <SEP> aufpresst.
<tb> Das <SEP> a-33Zethoxy-propionsäurenitril <SEP> kann
<tb> als <SEP> Lösungsmittel <SEP> sowie <SEP> als <SEP> Zwischenprodukt
<tb> für <SEP> die <SEP> Herstellung <SEP> von <SEP> Kunststoffen <SEP> und
<tb> Weichmachern <SEP> verwendet <SEP> werden.
<tb> Die <SEP> im <SEP> nachstehenden <SEP> Beispiel <SEP> alibebe benen <SEP> Teile <SEP> sind <SEP> Gewichtsteile.
EMI0002.0002
<I>Beispiel:</I>
<tb> 29 <SEP> Teile <SEP> Methylvinyläther, <SEP> 5(1 <SEP> Teile <SEP> Py.
ridin <SEP> und <SEP> 13 <SEP> Teile <SEP> Cyanwasserstoff <SEP> erhitzt
<tb> man <SEP> in <SEP> einer: <SEP> Stickstoffatmosphäre <SEP> im <SEP> Schüt telautoklaven <SEP> 6 <SEP> Stunden <SEP> bei <SEP> 200 . <SEP> Nach <SEP> dein
EMI0002.0003
Erkalten <SEP> deslillierl: <SEP> man <SEP> die <SEP> U <SEP> ni.set7tinTslö sun.. <SEP> Das <SEP> Deslillat <SEP> wird <SEP> mit <SEP> Salzsällre <SEP> neu trìllieI't <SEP> lind <SEP> mit <SEP> -Äther <SEP> ausbesehllttelt. <SEP> Durch
<tb> fraktionierte <SEP> Destillation <SEP> der <SEP> mit <SEP> Calcium ehlorid <SEP> t'etl'üclilleten <SEP> ätlier78eheil <SEP> LÖsnlit; <SEP> er hält, <SEP> male <SEP> 1? <SEP> Teile <SEP> a-Jlethot@--propio@säurc ilStril.
Process for the preparation of a ether carbonic acid nitrile. It is known that hydrogen cyanide reacts with saturated aliphatic ethers, for example dim @ ethyl and diethyl ethers, in the presence of dehydrating catalysts, with alkyl nitriles being formed when the ether bridge is broken.
It has now been found that the known α-methoxypropiononitrile is obtained. when methyl vinyl ether is treated with cyanide at elevated temperatures.
The reaction can already be brought about at 100 and below, but it is expedient to use higher temperatures, for example those of 150-300 or above. The conversion can be made cheaper by adding basic catalysts.
Suitable as such are, for example, basic or acid-binding metal compounds, primarily alkali and alkaline earth compounds, for example sodium and potassium hydroxide, sodium and potassium cyanide or copper hydroxide, but in particular also organic bases such as pyridine and pyrrolidine, if appropriate in connection with heavy metal salts,
for example copper cyanide. Such bases can simultaneously serve as solvents in the reaction. Other solvents in which both the methyl vinyl ether and cyanogen are soluble can be used, for example tetrahydrofuran or dioxane.
The hydrogen cyanide is expediently used in undiluted form, "but it can also contain inert diluent gases or vapors. The reaction can be carried out discontinuously or in uninterrupted operation, for example by mixing the starting materials with the catalyst and, if necessary a diluent is passed through a pipe or allowed to trickle through a vessel filled with Füllkör pern.
If you work in the liquid phase, you can increase the pressure via the Paxtial: pressure of the
EMI0002.0001
Increase the <SEP> corresponding <SEP> pressure <SEP> by <SEP> by pressing <SEP> an <SEP> inert <SEP> gas <SEP>.
<tb> The <SEP> a-33zethoxy-propionic acid nitrile <SEP> can
<tb> as <SEP> solvent <SEP> and <SEP> as <SEP> intermediate product
<tb> for <SEP> the <SEP> production <SEP> of <SEP> plastics <SEP> and
<tb> Plasticizers <SEP> are used <SEP>.
<tb> The <SEP> in the <SEP> below <SEP> example <SEP> alibebied <SEP> parts <SEP> are <SEP> parts by weight.
EMI0002.0002
<I> Example: </I>
<tb> 29 <SEP> parts <SEP> methyl vinyl ether, <SEP> 5 (1 <SEP> parts <SEP> Py.
ridin <SEP> and <SEP> 13 <SEP> parts <SEP> hydrogen cyanide <SEP> heated
<tb> man <SEP> in <SEP> a: <SEP> nitrogen atmosphere <SEP> in the <SEP> shaking autoclave <SEP> 6 <SEP> hours <SEP> at <SEP> 200. <SEP> After <SEP> your
EMI0002.0003
Cooling <SEP> deslillierl: <SEP> man <SEP> die <SEP> U <SEP> ni.set7tinTslö sun .. <SEP> The <SEP> Deslillat <SEP> becomes <SEP> with <SEP> Salzsällre <SEP> new trìllieI't <SEP> and <SEP> encased with <SEP> ether <SEP>. <SEP> through
<tb> fractional <SEP> distillation <SEP> of <SEP> with <SEP> calcium chloride <SEP> t'etl'üclilleten <SEP> ätlier78eheil <SEP> LÖsnlit; <SEP> he holds, <SEP> male <SEP> 1? <SEP> parts <SEP> a-Jlethot @ - propio @ säurc ilStril.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE236384X | 1941-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH236384A true CH236384A (en) | 1945-02-15 |
Family
ID=5901562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236384D CH236384A (en) | 1941-09-17 | 1943-03-15 | Process for the preparation of an ether carboxylic acid nitrile. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH236384A (en) |
-
1943
- 1943-03-15 CH CH236384D patent/CH236384A/en unknown
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