DE1232128B - Process for the preparation of monoaryl-substituted saturated fatty acid nitriles - Google Patents
Process for the preparation of monoaryl-substituted saturated fatty acid nitrilesInfo
- Publication number
- DE1232128B DE1232128B DER35014A DER0035014A DE1232128B DE 1232128 B DE1232128 B DE 1232128B DE R35014 A DER35014 A DE R35014A DE R0035014 A DER0035014 A DE R0035014A DE 1232128 B DE1232128 B DE 1232128B
- Authority
- DE
- Germany
- Prior art keywords
- nitriles
- fatty acid
- monoaryl
- chloride
- acid nitriles
- 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.)
- Pending
Links
- -1 saturated fatty acid nitriles Chemical class 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 4
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N alpha-methyl-naphthalene Natural products C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- UIAMCVSNZQYIQS-KTKRTIGZSA-N oleonitrile Chemical compound CCCCCCCC\C=C/CCCCCCCC#N UIAMCVSNZQYIQS-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides
- C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/28—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren-zur Herstellung von monoarylsubstituierten gesättigten Fettsäurenitrilen Es ist aus der deutschen Patentschrift 666 466 bekannt, daß man ungesättigte aliphatische Nitrile mit aromatischen Kohlenwasserstoffen zu Aralkylnitrilen umsetzen kann. Dieses Verfahren hat jedoch den Nachteil, daß nur sehr wenige Alkylennitrile, wie beispielsweise Ölsäurenitril, Acrylnitril, Crotonsäurenitril, zur Verfügung stehen, um für diese Synthese eingesetzt zu werden. Damit ist aber der Anwendungsbereich dieses Syntheseweges außerordentlich eingeengt und nur auf wenige Verbindungen anwendbar.Process for the production of monoaryl-substituted saturated fatty acid nitriles It is known from German Patent 666 466 that one unsaturated aliphatic Can react nitriles with aromatic hydrocarbons to give aralkyl nitriles. This However, the process has the disadvantage that only very few alkylene nitriles, such as Oleic nitrile, acrylonitrile, crotonic nitrile, are available to help for this Synthesis to be used. But that is the scope of this synthesis route extremely narrow and only applicable to a few compounds.
Es bestand daher die Notwendigkeit, Aralkylnitrile auf anderem, technisch leicht gangbarem Weg herzustellen.There was therefore a need to use aralkyl nitriles on other, technical grounds easily feasible way to produce.
Es wurde nun gefunden, daß sich monoarylsubstituierte gesättigte Fettsäurenitrile in einfacher Weise dadurch herstellen lassen, daß Monochlorfettsäurenitrile, die wenigstens 8 Kohlenstoffatome enthalten, in Gegenwart von Friedel-Crafts-Katalysatoren mit aromatischen Kohlenwasserstoffen, wie Benzol, Toluoyl, Xylol, Trimethylbenzol, Naphthalin, Monomethylnaphthalin, Dimethylnaphthalin, Anthracen umgesetzt werden. It has now been found that monoaryl-substituted ones become saturated Fatty acid nitriles can be produced in a simple manner in that monochloro fatty acid nitriles, containing at least 8 carbon atoms, in the presence of Friedel-Crafts catalysts with aromatic hydrocarbons such as benzene, toluoyl, xylene, trimethylbenzene, Naphthalene, monomethylnaphthalene, dimethylnaphthalene, anthracene are implemented.
Hierbei reagiert überraschenderweise nur das an die aliphatische Kohlenstoffkette gebundene Chloratom, während die Nitrilgruppe unangegriffen bleibt. Surprisingly, only that reacts to the aliphatic Chlorine atom bonded to the carbon chain, while the nitrile group remains unaffected.
Es ist zwar bekannt, Chlorcyan oder Trichloracetonitril mit aromatischen Kohlenwasserstoffen zu aromatischen Nitrilen umzusetzen (vgl. H 0 u b e n -Weil, »Methoden der organischen Chemie, 4. Auflage, Bd. VIII [1952], S. 315 und 319 bis 321). Diese Umsetzungen sind jedoch mit dem beanspruchten Verfahren nicht zu vergleichen. Although it is known to use cyanogen chloride or trichloroacetonitrile with aromatic To convert hydrocarbons to aromatic nitriles (cf.H 0 u b e n -Weil, »Methods of Organic Chemistry, 4th Edition, Vol. VIII [1952], pp. 315 and 319 bis 321). However, these implementations cannot be compared with the claimed method.
Im Chlorcyan, das als Chlorid der Cyansäure (HO-C =-N) aufzufassen ist, ist nämlich das Chloratom an das einzige mit einer Dreifachbindung am Stickstoffatom sitzende Kohlenstoffatom gebunden. Chlornitrile sind dagegen Ester der Blausäure, in denen das Chlor nicht an dem mit dem Stickstoffatom verbundenen Kohlenstoffatom, sondern an Kohlenstoffatomen, die daneben noch Wasserstoff gebunden enthalten, sitzt. In cyanogen chloride, to be understood as the chloride of cyanic acid (HO-C = -N) is, namely the chlorine atom to the only one with a triple bond to the nitrogen atom seated carbon atom bound. Chloronitriles, on the other hand, are esters of hydrogen cyanide, in which the chlorine is not on the carbon atom connected to the nitrogen atom, but on carbon atoms that also contain hydrogen bonded.
Die Kondensation von Trichloracetonitril mit aromatischen Verbindungen verläuft ebenfalls völlig anders als die des beanspruchten Verfahrens, denn hierbei erfolgt zunächst eine Anlagerung an die Nitrilgruppe, und das Anlagerungsprodukt muß mit Natriumhydroxyd behandelt werden, um Nitril neben Chloroform zu erhalten. Das Verfahren der Erfindung liefert dagegen in einer Reaktionsstufe sofort das gewünschte Endprodukt. The condensation of trichloroacetonitrile with aromatic compounds also runs completely different from that of the claimed method, because here First there is an addition to the nitrile group, and the addition product must be treated with sodium hydroxide to obtain nitrile in addition to chloroform. In contrast, the process of the invention immediately provides the desired product in one reaction step End product.
Monochlorfettsäurenitrile sind außerordentlich leicht durch Chlorierung von geradkettigen oder verzweigen gesättigten aliphatischen Nitrilen herzustellen. Letztere kann man beispielsweise nach dem Verfahren der deutschen Patentschrift 932 606 durch Umsetzung von primären aliphatischen Alkoholen mit Ammoniak in jeder beliebigen Kohlenstoffzahl herstellen, so daß damit ein bequemer, technisch leicht durchzuführender Weg zur Gewinnung der gewünschten Nitrile gegeben ist. In den eingesetzten Chlornitrilen ist das Chlor in statistischer Verteilung über das ganze Molekül an Kohlenstoffatome gebunden, die daneben noch Bindungen an Wasserstoffatome aufweisen. Monochloro fatty acid nitriles are extremely easy due to chlorination from straight-chain or branched saturated aliphatic nitriles. The latter can be done, for example, using the method described in the German patent specification 932 606 by reacting primary aliphatic alcohols with ammonia in each Produce any number of carbon, so that a convenient, technically easy The way to be carried out for obtaining the desired nitriles is given. In the deployed Chloronitrile is the chlorine in statistical distribution over the entire molecule Carbon atoms bonded, which also have bonds to hydrogen atoms.
An Stelle reiner Chlornitrile können auch die rohen Chlorierungsgemische, die bei der bekannten Chlorierung geradkettiger oder verzweigter aliphatischer Nitrile erhalten werden, ohne vorherige Aufarbeitung eingesetzt werden. Instead of pure chloronitriles, the crude chlorination mixtures, those in the known chlorination of straight-chain or branched aliphatic nitriles can be obtained without prior work-up.
Als ECatalysatoren eignen sich Aluminiumchlorid, Bisen(III)-chlorid, Bortrifluorid oder Ziim(IV)-chlorid, die vor oder während der Reaktion zugegeben werden. Aluminum chloride, bis (III) chloride, Boron trifluoride or Ziim (IV) chloride added before or during the reaction will.
Die Umsetzung wird vorzugsweise bei erhöhter Temperatur, zweckmäßig im Bereich von 80 bis 150"C durchgeführt.The reaction is preferably carried out at an elevated temperature carried out in the range of 80 to 150 "C.
Da Monochlorfettsäurenitrile im allgemeinen höhersiedende Flüssigkeiten darstellen und die Reaktion, besonders bei der Verwendung von höhermolekularen Chlorfettsäurenitrilen, bei höherer Temperatur abläuft, kann mit Vorteil ohne Lösungsmittel gearbeitet werden. Die Umsetzung kann jedoch auch in Gegenwart der für Friedel-Crafts-Reaktionen üblichen Lösungsmittel stattfinden. Geeignete Lösungsmittel sind insbesondere Kohlenwasserstoffe, Schwefelkohlenstoff oder Nitrobenzol. Since monochloro fatty acid nitriles are generally higher-boiling liquids represent and the reaction, especially when using higher molecular weight chlorofatty acid nitriles, takes place at a higher temperature, it is possible to work with advantage without a solvent. However, the reaction can also be carried out in the presence of those customary for Friedel-Crafts reactions Solvent take place. Suitable solvents are in particular hydrocarbons, Carbon disulfide or nitrobenzene.
Die nach dem erfindungsgemäßen Verfahren hergestellten Aralkylnitrile können als Schmierölzusätze, Oxydations- und Korrosionsschutzmittel sowie als Weichmacher für Kunstharze verwendet werden. The aralkyl nitriles produced by the process according to the invention can be used as lubricating oil additives, oxidation and corrosion protection agents and as plasticizers used for synthetic resins.
Beispiel 1 930 g Benzol und 270 g pulverisiertes Aluminiumchlorid wurden in einem 3-l-Rundkolben, der mit einem Rückflußkühler versehen war, gerührt. Zu diesem Gemisch ließ man 350 g Monochlor-isononansäurenitril (n2D0 = 1,4594; D240 = 0,9933) im Laufe von 2 Stunden tropfen. Das Monochlor-isononansäurenitril war durch Umsetzung von 3,5,5-Trimethylhexanol-(1) mit Ammoniak und anschließende Chlorierung des hierbei erhaltenen Isononansäurenitrils hergestellt worden. Nachdem das gesamte Nitril zugegeben worden war, wurde das Gemisch bis zum Sieden des Benzols erhitzt und 3 Stunden bei dieser Temperatur belassen. Nach dem Abkühlen wurde es auf 1000 g Eis gegeben, mit Salzsäure angesäuert und die obere Schicht einer Vakuumdestillation unterworfen. Bei einem Umsetzungsgrad von 860/o wurden 75°/0 der Theorie an Phenyl-isononansäurenitril vom Kp.0,2 = 115 bis 1200C erhalten. Example 1 930 g of benzene and 270 g of powdered aluminum chloride were stirred in a 3 liter round bottom flask fitted with a reflux condenser. 350 g of monochloroisononanoic acid nitrile (n2D0 = 1.4594; D240 = 0.9933) drop over the course of 2 hours. The monochloroisononanoic acid nitrile was by reacting 3,5,5-trimethylhexanol- (1) with ammonia and subsequent chlorination of the isononanoic acid nitrile obtained in this way. After the whole Nitrile was added, the mixture was heated until the benzene boiled and leave at this temperature for 3 hours. After cooling, it got to 1000 G of ice, acidified with hydrochloric acid and the upper layer of a vacuum distillation subject. At a degree of conversion of 860%, 75% of theory of phenyl-isononanoic acid nitrile obtained from b.p. 0.2 = 115 to 1200C.
Cl5H2lN (215,33): Berechnet ... C 83,66, H 9,83, N 6,51; gefunden ... C 83,04, H 9,67, N 6,41.Cl5H2IN (215.33): Calculated ... C 83.66, H 9.83, N 6.51; found ... C 83.04, H 9.67, N 6.41.
Beispiel 2 165 g pulverisiertes Aluminiumchlorid und 660 g Toluol wurden in einem 2-l-Rundkolben bei Raumtemperatur gerührt. Aus einem Tropftrichter wurden im Laufe von 1 Stunde 195 g Monochlor-iso-oktansäurenitril (n2D0 = 1,4510) zugegeben. Anschließend wurde das Gemisch 3 Stunden bei einer Temperatur belassen, bei der das Toluol an dem aufgesetzten Rückflußkühler eine schwache Kondensation zeigte. Example 2 165 g of powdered aluminum chloride and 660 g of toluene were stirred in a 2 L round bottom flask at room temperature. From a dropping funnel 195 g of monochloro-iso-octanoic acid nitrile (n2D0 = 1.4510) admitted. The mixture was then left for 3 hours at a temperature in which the toluene on the attached reflux condenser forms a weak condensation showed.
Anschließend gab man das Gemisch auf 700 g Eis, säuerte mit Salzsäure an und unterwarf die obere Schicht einer Destillation. Es wurde bei einer 940/0eigen Umsetzung eine Ausbeute von 810/, an Toluyl-isooktansäurenitril vom Kp.o, = 128 bis 136"C und n3° = 1,5160 erhalten.The mixture was then poured onto 700 g of ice and acidified with hydrochloric acid on and subjected the upper layer to a distillation. It was owned by a 940/0 Implementation of a yield of 810 /, of toluyl-isooctanoic acid nitrile of boiling point = 128 to 136 "C and n3 ° = 1.5160.
Beispiel 3 Ein Gemisch aus 210 g Monochlor-iso-nonansäurenitril, 425 g Naphthalin und 700 g Isooktan wurde in einem 2-l-Rundkolben gerührt, wobei nach und nach 147 g gepulvertes Aluminiumchlorid zugegeben wurden. Nach Beendigung der Zugabe des Aluminiumchlorids wurde das Gemisch 4 Stunden auf eine Temperatur von 100"C erhitzt und dann auf 900 g Eis gegossen. Bei der Destillation der oberen Schicht fielen bei einem Umsetzungsgrad von 950/o 70 °/O Naphthyl-iso-nonansäurenitril vom Kr.0,1 = 180 bis 1900C und n2D0 = 1,5651 an. Example 3 A mixture of 210 g of monochloroisononanoic acid nitrile, 425 g of naphthalene and 700 g of isooctane were stirred in a 2 l round bottom flask, whereby 147 g of powdered aluminum chloride were gradually added. After completion After the addition of the aluminum chloride, the mixture was heated to temperature for 4 hours heated by 100 "C and then poured onto 900 g of ice. During the distillation of the upper Layer fell at a degree of conversion of 950 / o 70 ° / o naphthyl-isononanoic acid nitrile from Kr 0.1 = 180 to 1900C and n2D0 = 1.5651.
C19H23N (265,38): Berechnet ... C 85,98, - H 8,74, N 5,28; gefunden ... C 85,76, H 8,56, N 5,18.C19H23N (265.38): Calculated ... C 85.98, -H 8.74, N 5.28; found ... C 85.76, H 8.56, N 5.18.
Molekulargewichtsbestimmung nach R a 5 t: Berechnet ... 265; gefunden ... 272.Molecular weight determination according to R a 5 t: Calculated ... 265; found ... 272.
Beispiel 4 In einem 4-l-Rundkolben wurde einem Gemisch aus 310 g Aluminiumchlorid und 1000 ml Isooktan im Laufe von 2 Stunden eine Lösung von 492 g eines nicht destillierten Gemisches aus Chlor-iso-nonansäurenitrilen und 580 g Naphthalin in 1500 ml Isooktan zugesetzt. Das Chlornitrilgemisch war durch Einführung von 0,8-g-Atomen Chlor je Mol Nitril hergestellt worden. Nach der Zugabe des Chlornitrilgemisches wurde das Reaktionsgemisch 8 Stunden unter Rühren auf 100"C erhitzt, anschließend auf Eis gegossen und mit Salzsäure angesäuert. Danach wurde zunächst bei Normaldruck das Isooktan (Kp.760 = 98 bis101°C), anschließend das nicht chlorierte Nitril (Kp.40 = 106 bis 109"C), das nicht umgesetzte Chlornitril (Kp.15 = 120 bis 131° C) sowie nicht umgesetztes Naphthalin im Vakuum abdestilliert. Als Rückstand verblieben 505 g eines Gemisches aus araliphatischen Nitrilen mit einer Viskosität von 230 cSt bei 80"C. Das Chlornitril war hierbei zu etwa 820/o umgesetzt worden. Example 4 A mixture of 310 g Aluminum chloride and 1000 ml of isooctane in the course of 2 hours a solution of 492 g of a non-distilled mixture of chloro-iso-nonanoic acid nitriles and 580 g Added naphthalene in 1500 ml of isooctane. The chloronitrile mixture was by introduction of 0.8 g atoms of chlorine per mole of nitrile. After adding the chloronitrile mixture the reaction mixture was heated to 100 ° C. for 8 hours with stirring, then poured onto ice and acidified with hydrochloric acid. It was then initially at normal pressure the isooctane (b.p. 760 = 98 to 101 ° C), then the non-chlorinated nitrile (b.p. 40 = 106 to 109 "C), the unreacted chloronitrile (bp 15 = 120 to 131 ° C) and unreacted naphthalene distilled off in vacuo. 505 remained as residue g of a mixture of araliphatic nitriles with a viscosity of 230 cSt at 80 ° C. The chloronitrile had been converted to about 820%.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER35014A DE1232128B (en) | 1963-04-24 | 1963-04-24 | Process for the preparation of monoaryl-substituted saturated fatty acid nitriles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER35014A DE1232128B (en) | 1963-04-24 | 1963-04-24 | Process for the preparation of monoaryl-substituted saturated fatty acid nitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1232128B true DE1232128B (en) | 1967-01-12 |
Family
ID=7404493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER35014A Pending DE1232128B (en) | 1963-04-24 | 1963-04-24 | Process for the preparation of monoaryl-substituted saturated fatty acid nitriles |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1232128B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2654412A1 (en) * | 1975-12-05 | 1977-06-23 | Lubrizol Corp | FUNCTIONAL FLUID AND THEIR USE |
-
1963
- 1963-04-24 DE DER35014A patent/DE1232128B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2654412A1 (en) * | 1975-12-05 | 1977-06-23 | Lubrizol Corp | FUNCTIONAL FLUID AND THEIR USE |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1232128B (en) | Process for the preparation of monoaryl-substituted saturated fatty acid nitriles | |
| DE1668571C3 (en) | Process for the preparation of 2-methyl-polycycloalkylmethylamines | |
| DE2642140A1 (en) | METHOD FOR PRODUCING BENZOYLCYANIDE | |
| DE844442C (en) | Process for the preparation of 1, 1-dihalo-1, 3-alkadienes | |
| DE4445825C2 (en) | Monoalkylphosphine and method of making the same | |
| DE1188577B (en) | Process for the production of omega-chlorine or omega-bromotiglinaldehyde, their acetal acylates | |
| DE1493752A1 (en) | Process for the preparation of pure anhydrous 2-amino-propionitrile | |
| DE1118778B (en) | Process for the production of biscuits | |
| DE1168413B (en) | Process for the preparation of monomethyl ester monoamides of carbocyclic, aromatic dicarboxylic acids | |
| DE1161881B (en) | Process for the preparation of 1, 2-epoxycyclododecadiene (5, 9) | |
| AT201592B (en) | Process for the preparation of substituted pyridine derivatives which are unsaturated in the side chain | |
| DE1620297C3 (en) | Process for the production of epsilon-caprolactams | |
| DE2111201C3 (en) | Process for the preparation of m (beta cyanathoxy) benzoic acid and its C deep 1 4 alkyl esters | |
| AT257617B (en) | Process for the preparation of benzodiazepine derivatives | |
| DE750059C (en) | Process for the preparation of N, N'-polymethylene-bis-aroylamides | |
| DE2026043A1 (en) | ||
| DE928948C (en) | Process for the preparation of 1, 7-heptamethylenediamine | |
| DE1030348B (en) | Process for the preparation of norcamphidine and its homologues substituted in the 2-position | |
| DE1044097B (en) | Process for the preparation of ring-alkylated aromatic amines | |
| AT259562B (en) | Process for the preparation of benzodiazepine derivatives | |
| DE855994C (en) | Process for the production of nitrogen-containing condensation compounds | |
| DE1140185B (en) | Process for the production of saturated ª ‰ -chlorofatty acid chlorides with 3 to 4 carbon atoms | |
| DE1910105A1 (en) | Chloromethyl esters of alpha, beta-unsaturated carboxylic acids | |
| DE2801887A1 (en) | Prepn. of para-substd. benzaldehyde derivs. - by hydrogenating complex formed from substd. benzene, oxalyl chloride and Friedel-Crafts catalyst | |
| DE1140187B (en) | Process for the preparation of branched, unsaturated aliphatic carboxylic acids, their salts or esters |