Color stabilization of amines
AssigneeHuntsman Petrochemical Corporation
InventorsWei-Yang Su, Mark L. Posey, Maarten P. ter Weeme
Life of this patent
Estimating the term…
Abstract
The present invention concerns a process for providing tertiary amine products which are color-stable, and have a greatly reduced tendency to take on color during their storage. According to the invention, an ethyleneamine derivative is added to the distillation pot prior to or during the distillation of the tertiary amine product. Preferably, the ethyleneamine derivative has a higher boiling point than the desired tertiary amine product so as to preclude the ethyleneamine from distilling over with the tertiary amine.
Claims8
1) A process for producing a color-stable tertiary amine product comprising the steps of:
- a) providing a distillation apparatus having a boiling pot portion, a condenser, and a receiver;
- b) providing a major amount of a desired tertiary amine product in said boiling pot, said tertiary amine having the chemical structure:
- 8
- in which x may be any integer between 1 and 8, including 1 and 8;
- wherein R1 may be hydrogen, hydroxy, or the group:
- 9
- wherein Y may be:
- i) hydrogen;
- ii) any alkyl group, whether straight-chain, branched, or cyclic containing between 1 and 10 carbon atoms, including 1 and 10;
- or iii) the group —(CH2)xOH in which x may be any integer between 1 and 8, including 1 and 8;
- and wherein Z may be may be:
- i) hydrogen;
- ii) any alkyl group, whether straight-chain, branched, or cyclic containing between 1 and 10 carbon atoms, including 1 and 10;
- iii) the group—(CH2)xOH in which x may be any integer between 1 and 8, including 1 and 8;
- or iv) an aminoalkyl group defined by the formula:
- 10
- in which m may be any integer between 1 and 6, including 1 and 6;
- and S and T are each independently selected from the group consisting of:
- hydrogen, or any C 1 to C6 alkyl group;
- and R2, and R3 may each independently be:
- i) hydrogen;
- ii) any alkyl group, whether straight-chain, branched, or cyclic containing between 1 and 10 carbon atoms, including 1 and 10;
- or iii) the group—(CH2)xOH in which x may be any integer between 1 and 8, including 1 and 8;
- c) providing a minor amount of an ethyleneamine derivative which has a boiling point higher than said desired tertiary amine product at standard temperature and pressure, said ethyleneamine derivative being selected from the group consisting of:
- ethylenediamine;
- aminoethylethanolamine;
- diethylenetriamine;
- triethylenetetramine;
- tetraethylenepentamine;
- pentaethylenehexamine;
- 1,2-propylenediamine;
- N-(2-hydroxypropyl)ethylenediamine;
- N-(2-hydroxybutyl)ethylenediamine;
- N-(2-hydroxyethyl)-1,2-propylenediamine;
- N-(2-hydroxypropyl)-1,2-propylenediamine;
- and N-(2-hydroxybutyl)-1,2-propylenediamine in said boiling pot;
- d) providing heat to said boiling pot portion so as to cause vaporization of said desired tertiary amine product and its subsequent condensation in said condensor to yield a liquid tertiary amine product;
- and
- e) collecting said liquid tertiary amine product in said receiver,
- wherein said ethyleneamine derivative is present in said pot portion in any amount between about 0.001% and about 20% by weight based on the total amount of tertiary amine present in said pot portion.
6) In a process for purification of a tertiary amine by distillation of said tertiary amine using a distillation apparatus having a pot portion, wherein the improvement comprises:
- addition of an ethyleneamine derivative having a boiling point at least 5° Centigrade higher than that of said tertiary amine to the pot portion of said distillation apparatus in an amount between about 0.001% and about 20% by weight based on the total amount of tertiary amine present in said pot portion, said ethyleneamine derivative being selected from the group consisting of ethylenediamine;
- aminoethylethanolamine;
- diethylenetriamine;
- triethylenetetramine;
- tetraethylenepentamine;
- pentaethylenehexamine;
- 1,2-propylenediamine;
- N-(2-hydroxypropyl)ethylenediamine;
- N-(2-hydroxybutyl)ethylenediamine;
- N-(2-hydroxyethyl)-1,2-propylenediamine;
- N-(2-hydroxypropyl)-1,2-propylenediamine;
- and N-(2-hydroxybutyl)-1,2-propylenediamine.
Dependencies are inferred from the claim text.