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US 4,381,401 AGranted
Aminoethylation process
AssigneeThe Dow Chemical Company
InventorGraham S. Poindexter
Life of this patent
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Abstract
2-Oxazolidinone or N-substituted derivatives thereof are reacted with aromatic amine hydrochlorides at elevated temperatures to produce 1,2-ethanediamines.
Claims5
A process for preparing 1,2-ethanediamines of the formula
- R.sub.3 --NR.sub.1 CH.sub.2 CH.sub.2 NHR.sub.2).sub.n
- where
- n is one or two;
- R.sub.1 is hydrogen or C.sub.1-20 hydrocarbyl;
- R.sub.2 is hydrogen, C.sub.1-20 alkyl, C.sub.1-20 hydroxyalkyl, R.sub.1 C(O)--, R.sub.1 OC(O)--, R.sub.1 SO.sub.2 --, (R.sub.1).sub.3 Si--, (R.sub.1).sub.3 P, (R.sub.1 O).sub.2 P(O)--, or (R.sub.1 O).sub.3 P--;
- and
- when n is 1, then R.sub.3 is ##STR4## wherein Y independently each occurrence is selected from the group consisting of halogen, amino, R.sub.1 and R.sub.1 X-- where X is oxygen or sulfur;
- and
- when n is 2, then R.sub.3 is:
- ##STR5## comprising contacting 2-oxazolidinone or a derivative thereof having the formula ##STR6## where R.sub.2 is as previously defined, with the hydrochloride derivative of an aromatic amine or diamine of the formula:
- R.sub.3 --NR.sub.1 H).sub.n.n(HCl),
- where n, R.sub.1 and R.sub.3 are as previously defined, at a temperature of from about 140.degree. C. to about 250.degree. C. for a time sufficient to form substantial amounts of the corresponding 1,2-ethanediamine hydrochloride salt and thereafter contacting with base.
9 more elements
Dependencies are inferred from the claim text.