CH261121A - Process for the preparation of the triacrylic acid ester of hydrogenated castor oil. - Google Patents
Process for the preparation of the triacrylic acid ester of hydrogenated castor oil.Info
- Publication number
- CH261121A CH261121A CH261121DA CH261121A CH 261121 A CH261121 A CH 261121A CH 261121D A CH261121D A CH 261121DA CH 261121 A CH261121 A CH 261121A
- Authority
- CH
- Switzerland
- Prior art keywords
- castor oil
- preparation
- acid ester
- hydrogenated castor
- acid
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung des Triaerylsäureesters des hydrierten Rizinusöles. Es wurde gefunden, dass man den Tri- aery lsäureestei- des gehärteten Rizinusöles herstellen kann, wenn man gehärtetes Ri zinusöl unter Zusatz einer Säure in Gegen wart von Niekelearbonvl mit Azetylen be handelt.
Die Herstellung kann in der Weise vorge nommen werden, dass man die Reaktionskom ponenten bei Raumtemperatur oder bei erhöh ter Temperatur miteinander iniseht. Die Um setzung kann unter Atmosphärendruck oder gegebenenfalls in einem Druckgefäss unter schwachem Überdruck bei Rauinteniperatur oder bei mässig erhöhter Temperatur, z. B. bei 30 bis 80" C, vorgenommen werden.
Man kann beispielsweise Azetylen in eine llisehung aus dem gehärteten Rizinusöl und der Säure ein leiten und gleichzeitig das Nielreleai-bonyl ztt- tropfen. Noeli zweekinä ssiger ist es, das gehär tete Rizinusöl, die Säure und das Nickelcarbo- nyl - gegebenenfalls unter Zusatz eines Lö sungsmittels - zii inisehen und in einer ge eigneten Schüttelapparatur mit Azetylen un ter geringem Überdruck zu schütteln.
Falls unter At.niosphärendruek gearbeitet werden soll, sind auf 1 Mol Azetylen minde stens 1# Mol Niekelearbonyl, mindestens 1:;; Mol einer einbasischen Säure und mindestens '/3 Mol des gehärteten Rizinusöles anzuwendem Beim Arbeiten im Druckgefäss und bei erhöh ter Temperatur, z.
B. bei 120 bis 150 C, kann die Menge des Niekelearbonyls reduziert werden, wobei aber Kohlenmonoxyd im über- sehuss zugegen sein muss.<B>Es</B> ist sogar möglich, das Niekelearbonyl bei der Umsetzung- bei er höhter Temperatur und unter Druck erst während der Reaktion entstehen zu lassen, in dem man in Gegenwart von metallischem Nickel oder dessen Salzen, insbesondere Halo geniden, und unter Zusatz von überschüssigem Kohlenmonoxyd arbeitet.
In diesem Falle sind nur geringe Mengen an Nickel. oder dessen Salzen erforderlieb, da diese Zusätze als Ka talysator wirken.
Als Säuren können beim vorliegenden Ver fahren beispielsweise Halogenwasserstoff säuren, insbesondere Salzsäure, ferner Phos phorsäure oder Essigsäure benützt werden. Sie werden vorteilhaft in wässriger Lösung angewendet.
Der neue Ester bildet ein (il, welches in den meisten Lösungsmitteln leicht löslich ist. Er kann als Zwischenprodukt., beispielsweise zur Herstellung von Polynierisaten, die z. B. als Textilhilfsstoffe,Klebemittel sowie als Be standteile von Kunstmassen und Lacken Ver wendung finden können, Anwendung finden. <I>Beispiel:</I> 74 Teile gehärtetes Rizinusöl werden in einer Mischung von 135 Teilen Benzol und 115 Teilen Benzin in der Wärme gelöst.
Die warme Lösung wird nach Versetzen mit 18 Teilen konzentrierter Salzsäure (d=1,199) und 10 Teilen Nickelearbonyl mit Azetylen gesehüt.telt, bis kein Gas mehr absorbiert wird. Anfä nglieli erfolgt. ein Farbumschlag nach Dunkelbraun, und iin Verlauf der Reaktion hellt die Farbe wieder auf und es scheidet sich festes NiClx ab, während eine beträcht liche Selbsterwärmung auftritt.
Nach dem Erkalten filtriert man vom aus geschiedenen Nickelchlorid ab und destilliert das Lösungsmittel unter vermindertem Druck ab.
Man erhält 80 Teile des Triacrylsäureesters des hydrierten Rizinusöles, der in den meisten Lösungsmitteln leicht löslich ist. Durch Er hitzen auf dem Wasserbad in Gegenwart von etwas Benzoylperoxyd (z. B. 0,1 % ) wird der neue Ester innerhalb kurzer Zeit (3 bis 10 Minuten) polymerisiert, wobei eine hornartige, zerreibbare Masse entsteht.
Process for the preparation of the triaerylic acid ester of hydrogenated castor oil. It has been found that the triarylic acid ester can be produced from hardened castor oil if hardened ricinus oil is treated with acetylene with the addition of an acid in the presence of Niekelearbonvl.
The preparation can be undertaken in such a way that the reaction components are iniseht with one another at room temperature or at an elevated temperature. The conversion can take place under atmospheric pressure or, if appropriate, in a pressure vessel under a slight excess pressure at Rauinteniperatur or at a moderately elevated temperature, e.g. B. at 30 to 80 "C, can be made.
For example, acetylene can be introduced into a solution of the hardened castor oil and the acid and the nielreleai-bonyl can be added at the same time. It is more difficult for Noeli to see the hardened castor oil, the acid and the nickel carbonyl - if necessary with the addition of a solvent - and to shake them in a suitable shaker with acetylene under a slight overpressure.
If work is to be carried out under atmospheric pressure, at least 1 mol of Niekelearbonyl, at least 1: ;; Mol of a monobasic acid and at least 1/3 mol of the hardened castor oil to be used. When working in a pressure vessel and at elevated temperature, eg.
B. at 120 to 150 C, the amount of Niekelearbonyl can be reduced, but carbon monoxide must be present in excess. <B> It </B> is even possible to use the Niekelearbonyl during the reaction - at elevated temperature and to be created under pressure only during the reaction, in which one geniden in the presence of metallic nickel or its salts, especially halo, and with the addition of excess carbon monoxide works.
In this case there are only small amounts of nickel. or its salts required, since these additives act as a catalyst.
The acids used in the present process are, for example, hydrohalic acids, in particular hydrochloric acid, and also phosphoric acid or acetic acid. They are advantageously used in aqueous solution.
The new ester forms a (il, which is easily soluble in most solvents. It can be used as an intermediate product, for example for the production of polynes, which can be used, for example, as textile auxiliaries, adhesives and as components of plastics and lacquers , Application. <I> Example: </I> 74 parts of hydrogenated castor oil are dissolved in a mixture of 135 parts of benzene and 115 parts of gasoline in the heat.
After adding 18 parts of concentrated hydrochloric acid (d = 1.199) and 10 parts of nickel carbonyl, the warm solution is protected with acetylene until no more gas is absorbed. Initially done. a color change to dark brown, and in the course of the reaction the color lightens again and solid NiClx separates out, while considerable self-heating occurs.
After cooling, the precipitated nickel chloride is filtered off and the solvent is distilled off under reduced pressure.
80 parts of the triacrylic acid ester of hydrogenated castor oil, which is readily soluble in most solvents, are obtained. By heating it on a water bath in the presence of some benzoyl peroxide (e.g. 0.1%), the new ester is polymerized within a short time (3 to 10 minutes), producing a horn-like, friable mass.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH261121T | 1947-02-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH261121A true CH261121A (en) | 1949-04-30 |
Family
ID=4473809
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH261121D CH261121A (en) | 1947-02-21 | 1947-02-21 | Process for the preparation of the triacrylic acid ester of hydrogenated castor oil. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH261121A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1011415B (en) * | 1953-12-03 | 1957-07-04 | Basf Ag | Process for the production of acrylic acid-propionic acid mixtures and their functional derivatives |
DE1058048B (en) * | 1956-09-22 | 1959-05-27 | Basf Ag | Process for the preparation of acrylic acid compounds |
-
1947
- 1947-02-21 CH CH261121D patent/CH261121A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1011415B (en) * | 1953-12-03 | 1957-07-04 | Basf Ag | Process for the production of acrylic acid-propionic acid mixtures and their functional derivatives |
DE1058048B (en) * | 1956-09-22 | 1959-05-27 | Basf Ag | Process for the preparation of acrylic acid compounds |
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