Organo-1-oxa-4-azonium cyclohexane compounds

Patent metadata

Field	Value
Publication number	US-10633355-B2
Application number	US-201815981084-A
Country	US
Kind code	B2
Filing date	May 16, 2018
Priority date	Dec 4, 2014
Publication date	Apr 28, 2020
Grant date	Apr 28, 2020

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

The invention claimed is:

1. A morpholinium compound comprising a 1-oxa-4-azonium cyclohexane salt having a structure of:
2-R 1 -2-R 2 -3-R 3 -3-R 4 -4-R 9 -4-R 10 -5-R 5 -5-R 6 -6-R 7 -6-R 8 -1-oxa-4-azoniumcyclohexane + -X − ,
wherein R 1 -R 8 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; at least one of R 1 -R 8 is an alkyl group; R 9 and R 10 form a cyclic alkyl group having the formula C m H 2m forming a heterocycle of ring size q, where m is in the range from 4 to 8, and q is in the range of 5 to m+1; X is hydroxide; and the total number of C atoms in the molecule is in a range of 8 to 17.

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

3. The morpholinium compound of claim 1 having the Formula 1, 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.

4. The morpholinium compound of claim 1 having the Formula 1, wherein at least two of R 1 -R 8 are an alkyl group and the at least two of the alkyl groups are on the same C atom.

5. A morpholinium compound comprising a 1-oxa-4-azonium cyclohexane salt having a structure of:
2-R 1 -2-R 2 -3-R 3 -3-R 4 -4-R 9 -4-R 10 -5-R 5 -5-R 6 -6-R 7 -6-R 8 -1-oxa-4-azoniumcyclohexane + -X − ,
wherein R 1 -R 8 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; R 9 and R 10 form a cyclic alkyl group having the formula C m H 2m forming a heterocycle of ring size q, where m is in the range from 4 to 8, and q is in the range of 5 to m+1; X is a halide or hydroxide; and the total number of C atoms in the molecule is in a range of 13 to 17.

6. A morpholinium compound comprising a 1-oxa-4-azonium cyclohexane salt having a structure of:
2-R 1 -2-R 2 -3-R 3 -3-R 4 -4-R 9 -4-R 10 -5-R 5 -5-R 6 -6-R 7 -6-R 8 -1-oxa-4-azoniumcyclohexane + -X − ,
wherein R 1 -R 8 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; R 9 and R 10 form a cyclic alkyl group having the formula C m H 2m forming a heterocycle of ring size q, where m is in the range from 4 to 8, and q is 5 or 6; X is hydroxide; and the total number of C atoms in the molecule is in a range of 10 to 17.

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

• C07D295/023

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

• C07D295/027

  containing only one hetero ring · CPC title

• C07D497/10

  Spiro-condensed systems · CPC title