N-methylated amines from selective vapor phase amination of amino ether alcohols
AssigneeAir Products and Chemicals, Inc.
InventorsJohn William Mitchell, Richard Paul Underwood, Michael Edward Ford, Gamini Ananda Vedage, Hong-Xin Li
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Abstract
A method for converting amino ether alcohols to amino ether amines by amination in the vapor phase with a catalyst comprising copper and zinc. The catalyst may also comprise an alkali, alkaline earth, or lanthanide element as a promoter.
Claims17
A method for converting an amino ether alcohol to an amino ether amine, the method comprising contacting a catalyst comprising at least one of zinc oxide or a zinc salt, and at least one of copper oxide or a copper salt, with a vapor phase mixture comprising the amino ether alcohol and an amine, wherein the amino ether alcohol has the formula NR1R2R3, wherein R1 and R2 each individually is selected from the group consisting of H, C1–C10 alkyl, a C6–C10 aryl, and a C6–C10 aralkyl R3 is a C4–C10 alkyl group having within it an ether linkage and also containing at least one hydroxyl group, and the amine has the formula, NHR4R5, wherein R4 and R5 each individually is H, a C1–C10 alkyl, a C6–C10 aryl, or a C6–C10 aralkyl group, provided that no more than one of R4 and R5 is H, wherein the contacting is performed at a temperature ranging from 120° C. to 300° C. and a pressure ranging from 0 to 500 psig (101 to 3549 kPa).
The method of claim 8, wherein the promoter is present at 0.2 to 2 wt %, based on the total weight of the catalyst.
A method for converting dimethylaminoethoxyethanol to an amino ether amine, the method comprising:
- contacting a catalyst with hydrogen gas to produce an activated catalyst;
- and
- contacting the activated catalyst with a vapor phase mixture comprising dimethylaminoethoxyethanol and at least one of methylamine or dimethylamine;
- wherein the catalyst comprises the following materials in the following amounts, based on the total catalyst weight:
- 20 to 70 wt% copper oxide,
- 20 to 65 wt% zinc oxide, and
- 0.3 to 1.5 wt% of at least one of potassium or cesium.
Dependencies are inferred from the claim text.