Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-09-11
2001-05-22
Richter, Johann (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C568S319000
Reexamination Certificate
active
06235940
ABSTRACT:
The present invention relates to a process for preparing alkoxylated amines or alcohols or mixtures thereof, in which an amine or a mixture of two or more amines, or an alcohol or a mixture of two or more alcohols, or a mixture of one or more amines and one or more alcohols, is reacted with an alkylene oxide, or a mixture of two or more different alkylene oxides, in one or more successive reaction steps.
The reaction products of amines or alcohols with alkylene oxides are known as surface-active and interface-active compounds and are employed in a wide variety of industrial fields. Particular examples are laundry detergents and cleaners, personal care products or industrial applications, for example use as emulsifiers, dispersants, emulsion breakers or dispersion breakers, or as intermediates, thickeners or lubricants.
Processes known from the prior art for alkoxylating amines are generally carried out in one or two stages, while single-stage processes are generally preferred for the alkoxylation of alcohols.
Thus, for example, DE-A 195 44 739 describes a process for preparing alkoxylated polyethylenimines by alkoxylation of polyethylenimines in one or two process steps to give reaction products which contain from 1 to 200 mol of alkylene oxide groups per amino group in the polyethylenimine. In the single-stage procedure, anhydrous polyethylenimines and from 1 to 20 mol %, based on polyethylenimines, of at least one anhydrous base are initially placed in the reaction vessel or aqueous solutions of these materials are dried and after removal of all the water at >135 to 150° C. reacted with at least one alkylene oxide. In the two-stage procedure, polyethylenimine is reacted in the first process step at from 80 to 100° C. with from 0.7 to 0.9 mol, based on 1 mol of amino groups in the polymer, of at least one alkylene oxide in aqueous solution, and in the second process step the reaction product obtained in the first process step is reacted at from 120 to 150° C. with at least one alkylene oxide in the absence of water and in the presence of from 1 to 20 mol %, based on polyethylenimine, of an alkaline catalyst to give alkoxylated polyethylenimines containing from 1 to 200 mol of alkylene oxide groups per amino group in the polyethylenimine. Light-colored or virtually colorless products are, according to this publication, only obtained when a high catalyst concentration is employed. The publication gives no information about the olfactory properties of the resulting product.
Suggestions for suitable reaction conditions in the preparation of interface-active alkoxylation products may be found, for example, in N. Schönfeldt, Grenzflächenaktive Äthylenoxid-Addukte, Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart, 1976, p. 15 ff. and p. 83 ff.
However, under the alkoxylation conditions customarily selected, by-products whose type, number and amount may differ depending on the process variant selected are formed in addition to the actual alkoxylation products. For example, carbonyl compounds such as acetaldehyde (as a rule when using ethylene oxide) or higher aldehydes and also their downstream products are frequently formed, and these can influence the color and odor of the alkoxylation product.
The alkoxylated amines and alcohols, in particular the abovementioned polyethylenimines, obtainable by the methods described in the prior art can therefore, depending on the degree of alkoxylation, be strongly discolored and have an extremely unpleasant odor, or it is necessary to work under uneconomical process conditions, for example using large amounts of catalyst, in order to reduce the discoloration.
Attempts to at least substantially remove the compounds causing the discoloration and odor afterwards, e.g. by oxidative or reductive bleaching or by stripping, for example using nitrogen or steam, also generally do not lead to the desired success.
It is an object of the present invention to provide a process for the alkoxylation of amines or alcohols or mixtures thereof which leads to products which have very little discoloration and additionally have only a very small proportion of compounds which cause undesirable odors.
We have found that this object is achieved by carrying out the alkoxylation in the presence of formic acid or a salt of formic acid or a mixture of two or more thereof.
The present invention accordingly provides a process for preparing an alkoxylated amine or a mixture of two or more alkoxylated amines, or an alkoxylated alcohol or a mixture of two or more alkoxylated alcohols, or a mixture of one or more alkoxylated amines and one or more alkoxylated alcohols, in which a reaction mixture comprising an amine or a mixture of two or more amines, or an alcohol or a mixture of two or more alcohols, or a mixture of one or more amines and one or more alcohols, and an alkylene oxide, or a mixture of two or more alkylene oxides is reacted in one or more successive reaction steps, wherein at least one of the reaction steps is carried out in the presence of a basic catalyst and wherein formic acid or a salt of formic acid, or a mixture of two or more thereof is present in the reaction mixture in at least one of the reaction steps, so as to give an alkoxylated reaction product.
For the purposes of the present invention, the term “reaction step” means an overall reaction after which an isolable product or intermediate which undergoes no further reactions (with the possible exception of secondary reactions proceeding at a low rate) is present. The process of the present invention can therefore proceed, for example, in a single “reaction step” regardless of how many individual reaction events actually occur in the reaction mixture provided that the desired end product is present after the conclusion of the reaction. However, the process of the present invention can also be carried out in a plurality of steps, i.e. individual steps leading to the desired end product can be carried out sequentially so that the completion of the first step is followed by a second step which can, at a later point in time, be carried out in the same reaction vessel or in a different reaction vessel. If appropriate, this can be followed by further steps until the desired end product has been obtained.
In the process of the present invention, it is possible, for example, to subject any compounds which bear at least one amino group (amines) to an alkoxylation, where the amines can be compounds which can have one or more primary or secondary amino groups and, if desired, additionally one or more tertiary amino groups. Mixtures of two or more such compounds can just as well be subjected to the process of the present invention. The process of the present invention is accordingly not restricted to the reaction of compounds having only one amino group, but it is also possible, for example, to use diamines or polyamines. Examples of suitable amines are ammonia, methylamine, ethylamine, 1-propylamine, 2-propylamine, 1-butylamine, 2-butylamine, 1-pentylamine, 2-pentylamine, 3-pentylamine, the corresponding isomeric hexylamines, heptylamines, octylamines, nonylamines, decylamines and also higher linear or branched alkylamines which are obtainable, for example, by amination of fatty alcohols having up to 24 carbon atoms. Likewise suitable are the corresponding secondary amines of the abovementioned compounds as are obtainable, for example, by monoalkylation of the compounds mentioned. Examples are dimethylamine, N-methylethylamine, N-diethylamine, N-methylpropylamine, N-methylbutylamine, N-methyl-pentylamine, N-methylhexylamine and the like.
Further suitable compounds are oligoamines which have at least two amino groups per molecule. These include, for example, ethylenediamine, propylenediamine, butylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine and the like; this listing is intended to encompass any positional isomers of the compounds mentioned. The process of the present invention can likewise be carried out using amines which have both primary and second
Dockner Toni
Mohr Juergen
BASF - Aktiengesellschaft
Davis Brian J.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Richter Johann
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