Continuous method for producing fatty acid amides
View Patent ↗The invention relates to a continuous method for producing fatty acid amides, according to which at least one fatty acid of formula (I), R 3 —COOH (I) wherein R 3 is an optionally substituted aliphatic hydrocarbon radical, is reacted with at least one amine of formula (II), HNR 1 R 2 (II) wherein R 1 and R 2 are independently hydrogen or a hydrocarbon radical comprising between 1 and 100 C atoms, to form an ammonium salt, and said ammonium salt is then reacted to form a fatty acid amide, under microwave irradiation in a reaction pipe, the longitudinal axis of the pipe being oriented in the direction of propagation of the microwaves of a monomode microwave applicator.
1. A continuous process for preparing a fatty acid amide comprising the steps of reacting at least one fatty acid of the formula I
R 3 —COOH (I)
wherein R 3 is a substituted or unsubstituted aliphatic hydrocarbon radical having 5 to 50 carbon atoms with at least one amine of the formula II
HNR 1 R 2 (II)
wherein R 1 and R 2 are each independently hydrogen or a hydrocarbon radical having 1 to 100 carbon atoms
forming an ammonium salt and subsequently converting this ammonium salt to the fatty acid amide under microwave irradiation in a reaction tube whose longitudinal axis is in the direction of propagation of the microwaves from a monomode microwave applicator and whose ratio of length to diameter is greater than 5, wherein the microwave applicator is configured as a cavity resonator, and wherein the cavity resonator is operated in E 01n mode where n is an integer from 1 to 200.
2. The process as claimed in claim 1 , wherein the salt is irradiated with microwaves in a substantially microwave-transparent reaction tube within a hollow conductor connected via waveguides to a microwave generator.
3. The process as claimed in claim 1 , wherein the microwave applicator is configured as a cavity resonator of the reflection type.
4. The process as claimed in claim 1 , wherein the reaction tube is aligned axially with a central axis of symmetry of the hollow conductor.
5. The process as claimed in claim 1 , wherein the salt is irradiated in a cavity resonator with a coaxial transition of the microwaves.
6. The process as claimed in claim 1 , wherein the cavity resonator is operated in E 01n mode where n is an integer from 4 to 50.
7. The process as claimed in claim 1 , wherein R 3 is an unsubstituted alkyl radical having 5 to 50 carbon atoms.
8. The process as claimed in claim 1 , wherein R 3 is a hydrocarbon radical which has 5 to 50 carbon atoms and at least one substituent selected from the group consisting of halogen atoms, C 1 -C 5 -alkoxyalkyl, poly(C 1 -C 5 -alkoxy)alkyl, carboxyl, ester, amide, cyano, nitrile, nitro, sulfo and aryl groups having 5 to 20 carbon atoms, where the C 5 -C 20 — aryl groups may have substituents selected from the group consisting of halogen atoms, halogenated alkyl radicals, C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 5 -alkoxy, ester, amide, cyano, nitrile and nitro groups.
9. The process as claimed in claim 1 , wherein R 3 comprises 5 to 30 carbon atoms.
10. The process as claimed in claim 1 , wherein R 3 comprises one or more double bonds.
11. The process as claimed in claim 1 , wherein R 1 and R 2 are each independently a hydrocarbon radical having 1 to 100 carbon atoms.
12. The process as claimed in claim 1 , wherein R 1 is a hydrocarbon radical having 1 to 100 carbon atoms and R 2 is hydrogen.
13. The process as claimed in claim 1 , wherein R 1 or R 2 or both have substituents selected from the group consisting of C 1 -C 5 -alkoxyalkyl, cyano, nitrile, nitro and C 5 -C 20 -aryl groups.
14. The process as claimed in claim 1 , wherein R 1 or R 2 or both are substituted by C 5 -C 20 -aryl groups, wherein the C 5 -C 20 -aryl groups have at least one substituent selected from the group consisting of halogen atoms, halogenated alkyl radicals, C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 5 -alkoxy, ester, amide, cyano, nitrile and nitro-substituted phenyl radicals.
15. The process as claimed in claim 1 , wherein R 1 and R 2 together with the nitrogen atom to which they are bonded form a ring.
16. The process as claimed in claim 1 , wherein R 1 and R 2 are each independently a radical of the formula III
—(R 4 —O) n —R 5 (III)
wherein
R 4 is an alkylene group having 2 to 6 carbon atoms,
R 5 is a hydrocarbon radical having 1 to 24 carbon atoms or a group of the formula —NR 10 R 11 ,
n is an integer from 2 to 50 and
R 10 , R 11 are each independently an aliphatic radical having 1 to 24 carbon atoms, an aryl group or heteroaryl group having 5 to 12 ring members, a poly(oxyalkylene) group having 1 to 50 poly(oxyalkylene) units, where the poly(oxyalkylene) units derive from alkylene oxide units having 2 to 6 carbon atoms, or R 10 and R 11 together with the nitrogen atom to which they are bonded form a ring having 4, 5, 6 or more ring members.
17. The process as claimed in claim 1 , wherein R 1 and R 2 are each independently a radical of the formula IV
—[R 6 —N(R 7 )] m —(R 7 ) (IV)
wherein
R 6 is an alkylene group having 2 to 6 carbon atoms or mixtures thereof,
each R 7 is independently hydrogen, an alkyl radical having up to 24 carbon atoms, a polyoxyalkylene radical —(R 4 —O) p —R 5 , or a polyiminoalkylene radical —[R 6 —N(R 7 )] 1 —(R 7 ), where R 4 , R 5 , R 6 and R 7 are each as defined above and q and p are each independently 1 to 50, and
m is from 1 to 20.
18. The process as claimed in claim 1 , wherein the microwave irradiation is performed at temperatures between 150 and 300° C.
19. The process as claimed in claim 1 , wherein the microwave irradiation is performed at pressures above atmospheric pressure.
20. The process as claimed in claim 1 , wherein R 1 or R 2 or both substituents are independently an aliphatic radical having 1 to 24 carbon atoms.
21. The process as claimed in claim 16 , wherein R 10 and R 11 are each independently an aliphatic radical having 2 to 18 carbon atoms.
22. The process as claimed in claim 17 , wherein m is from 2 to 10.