Organo-1-oxa-4-azonium cyclohexane compounds

Patent metadata

Field	Value
Publication number	US-9522896-B2
Application number	US-201414561132-A
Country	US
Kind code	B2
Filing date	Dec 4, 2014
Priority date	Dec 4, 2014
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

Novel 1-oxa-4-azonium cyclohexane salts are described. These compounds can be used as structure directing agents, and they overcome many of the typical problems associated with OSDA synthesis and subsequent zeolite synthesis. Methods for synthesis of the 1-oxa-4-azonium cyclohexane salts from a variety of starting materials are also described. A substituted hydrocarbon is added to water to form a mixture, and a 1-oxa-4-azacyclohexane derivative is then added. The reaction mixture stirred until a solution containing the 1-oxa-4-azonium cyclohexane salt is obtained.

First claim

What is claimed:

1. A morpholinium compound comprising:
a 1-oxa-4-azonium cyclohexane salt having a structure of:
Formula 3:

[tris-N,N′,N″-triR 9 -(2,2′,2″-triR 1 -2,2′,2″-triR 2 -3,3′,3″-triR 3 -3,3′,3″triR 4 -5,5′,5″-triR 5 -5,5′,5″-triR 6 -6,6′,6″,6″-triR 7 -6,6′,6″-triR 8 -1,1′, 1″-oxa-4,4′,4″-azoniumcyclohexane)-R 10 ] 3+ 3X − , wherein R 1 -R 9 are independently selected from H or an alkyl group having the formula C n H 2n−1 , where n is in the range from 1 to 4, X is halide or hydroxide, the total number of C atoms in the molecule is the range of 15 to 36, and R 10 is an alkyl group having the formula C m H 2m−1 , where m is in the range from 3 to 8 and is connected to the 4, 4′ and 4″ N atoms at positions x, y and z of the alkyl chain where x, y and z are independently selected from 1 to m;
wherein Formula 3 is represented by a structure:

2. The morpholinium compound of claim 1 having the Formula 3, wherein X is hydroxide.

3. The morpholinium compound of claim 1 having the Formula 3, wherein R 1 -R 8 are H.

4. The morpholinium compound of claim 1 having the Formula 3, wherein at least one of R 1 -R 8 is an alkyl group.

5. The morpholinium compound of claim 1 having the Formula 3 wherein when R 9 is an alkyl group, X is hydroxide.

6. The morpholinium compound of claim 1 having the Formula 3, wherein at least two of R 1 -R 8 are an alkyl group, and wherein the at least two of R 1 -R 8 are R 1 and R 2 , or R 3 and R 4 , or R 5 and R 6 , or R 7 and R 8 .

7. The morpholinium compound of claim 1 having the Formula 3, wherein at least two of R 1 -R 8 are an alkyl group, and wherein at least two of R 1 -R 8 are the same alkyl group.

8. The morpholinium compound of claim 1 having the Formula 3, wherein the 1-oxa-4-azonium cyclohexane salt comprises at least one of the mono-, di-, or tri-halides or hydroxides of mono-, bis-, or tris-:
4-butylmorpholine, 4-propylmorpholine, 4-ethylmorpholine, 4-methylmorpholine, morpholine, 2-methylmorpholine, 2,4-dimethylmorpholine, 4-ethyl-2-methylmorpholine, 4-propyl-2-methylmorpholine, 3 -methylmorpholine, 3,4-dimethylmorpholine, 4-ethyl-3-methylmorpholine, 4-propyl-3-methylmorpholine, 5-methylmorpholine, 2,5-dimethylmorpholine, 4-ethyl-5-methylmorpholine, 4-propyl-5-methylmorpholine, 5-ethyl-2-methylmorpholine, 6-methylmorpholine, 4,6-dimethylmorpholine, 4-ethyl-6-methylmorpholine, 4-propyl-6-methylmorpholine, 2,6-dimethylmorpholine, 2,4,6-trimethylmorpholine, 4-ethyl-2,6-dimethylmorpholine, 2,3-dimethylmorpholine, 2,3,4-trimethylmorpholine, 4-ethyl-2,3-dimethylmorpholine, 2,5-dimethylmorpholine, 2,4,5-trimethylmorpholine, 4-ethyl-2,5-dimethylmorpholine, 2,2-dimethylmorpholine, 2,2,4-trimethylmorpholine, 4-ethyl-2,2-dimethylmorpholine, 3,3-dimethylmorpholine, 3,3,4-trimethylmorpholine, 4-ethyl-3,3-dimethylmorpholine, 5,5-dimethylmorpholine, 4,5,5-trimethylmorpholine, 4-ethyl-5,5-dimethylmorpholine, 6,6-dimethylmorpholine, 4,6,6-trimethylmorpholine, 4-ethyl-6,6-dimethylmorpholine, 5-ethyl-2-methylmorpholine and combinations thereof.

Assignees

• Uop Llc

Inventors

• Nicholas Christopher P
• Miller Mark A
• Galey Melissa M
• Yuhas Benjamin D
• Prabhakar Sesh

Classifications

• C07D295/037 Primary

  with quaternary ring nitrogen atoms · CPC title

• C07D295/027 Primary

  containing only one hetero ring · CPC title

• C07D295/023

  Preparation; Separation; Stabilisation; Use of additives · CPC title