Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2003-03-24
2004-12-07
Stockton, Laura L. (Department: 1626)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C548S552000, C548S554000, C514S424000
Reexamination Certificate
active
06828278
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to a process for producing N-aryl-2-lactams and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl amines utilizing a metal catalyst, which is optionally supported.
BACKGROUND OF THE INVENTION
Lactams, and particularly pyrrolidones, are important constituents in many industrial applications, including as solvents in chemical reactions, components in ink and coating formulations, coating strippers in the electronics industry, formulating agents in crop protection products, and as intermediates in the production of pharmaceuticals. For example, N-cyclohexyl-2-pyrrolidone is used as a solvent or intermediate in many industrial applications, including the electronics industry (photo-resist stripping solutions), industrial cleaners, oil/gas well maintenance, and fiber dyeing. N-[2-hydroxyethyl]-2-pyrrolidone is useful in industrial cleaning, printing inks, and gasoline and oil additives. N-octyl-2-pyrrolidone is useful, for example, in the manufacture of agricultural products, as a detergent and dispersant, in industrial and metal cleaners, in printing inks and in fiber dyeing.
Pyrrolidone derivatives are generally prepared on an industrial scale by the catalytic or non-catalytic reaction of gamma butyrolactone with an alkyl amine or ammonia. For example, U.S. Pat. No. 4,824,967 describes a vapor phase process for the production of 2-pyrrolidone using &ggr;-butyrolactone and ammonia at a temperature of 230-300° C. and a pressure of 0.35 MPa to 2.1 MPa. A magnesium silicate catalyst is used which needs to be separated and regenerated following the reaction, and which may trap considerable amounts of the product. U.S. Pat. No. 5,393,888 describes a liquid-phase process for producing 2-pyrrolidone from &ggr;-butyrolactone and ammonia in the absence of a catalyst, but at high temperature and pressure; the reaction is carried out at 200-375° C. and 4.8 to 12.4 MPa. In U.S. Pat. No. 6,348,601, methanol is reacted with ammonia in the presence of a catalyst, and the resultant mixture of methyl amines is reacted with y-butyrolactone to form N-methyl-2-pyrrolidone. The reaction temperatures are 300-500° C. and the pressures are 0.8 to 3.6 MPa. U.S. Pat. No. 6,248,902 describes a liquid-phase, non-catalytic process for the production of N-methyl-pyrrolidone from &ggr;-butyrolactone and monomethylamine.
Aryl compounds have also been used as the amine in reactions with lactones. For example, U.S. Pat. No. 3,775,431 describes the synthesis of N-phenyl-&ggr;-methyl-&ggr;-butyrolactam from &ggr;-methyl-&ggr;-butyrolactone and aniline in a reaction that is carried out at a temperature of 250° C. under a nitrogen atmosphere. U.S. Pat. No. 5,538,985 describes the synthesis of 1-(4-chlorophenyl)-2-pyrrolidone from a reaction of p-chloroaniline and &ggr;-butyrolactone in the presence of hydrochloric acid; the reaction was carded out for 17 hours at temperatures up to 140° C.; the product was recovered in a multi-step process. U.S. Pat. No. 6,350,883 describes a gas-phase process for reacting lactones with amines or ammonia in the presence of aluminosilicate zeolites to produce lactams; the reactions are carried out at 180-400° C. and 0 to 1 MPa.
An efficient and low cost process for the production of aryl, alkyl and cycloalkyl pyrrolidones would be advantageous. Disclosed herein is a novel, one-step process for converting lactones to aryl and cycloalkyl lactams in the presence of catalysts.
SUMMARY OF THE INVENTION
The present invention relates to a process for preparing N-aryl-2-lactam (III), N-cycloalkyl-2-lactam (IV), or a mixture thereof, which comprises the step of contacting a lactone (I) with an aryl amine (II) in the presence of a catalyst and hydrogen gas;
wherein:
(i) n=0-11;
(ii) R
1
, R
2
, R
3
, R
4
, R
5
and R
6
taken independently are hydrogen, hydrocarbyl or substituted hydrocarbyl, C
1
to C
18
unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkyl containing at least one heteroatom, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl;
(iii) R
7
is an aromatic group having from 6 to 30 carbons, and R
8
is a fully or partially reduced derivative of R
7
;
(iv) N-aryl-2-lactam (III), N-cycloalkyl-2-lactam (IV), or a mixture thereof, may comprise 100% by weight of the total product formed, or wherein additional products may be produced; and
(v) the catalyst is selected from metals from the group consisting of palladium, ruthenium, rhenium, rhodium, iridium, platinum, nickel, cobalt, copper, iron, osmium; compounds thereof; and combinations thereof.
REFERENCES:
patent: 3775431 (1973-11-01), Rodewald et al.
patent: 4824967 (1989-04-01), Liu et al.
patent: 5393888 (1995-02-01), Minnock et al.
patent: 5538985 (1996-07-01), Iizuka et al.
patent: 6248902 (2001-06-01), Bertola
patent: 6348601 (2002-02-01), Ohlbach et al.
patent: 6350883 (2002-02-01), Chen et al.
Deitch Gerald E.
E.I. du Pont de Nemours and Company
Stockton Laura L.
LandOfFree
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