Continuous synthesis of isooctyl nitrate in a flow reactor

Patent metadata

Field	Value
Publication number	US-10017457-B2
Application number	US-201515123100-A
Country	US
Kind code	B2
Filing date	Mar 5, 2015
Priority date	Mar 7, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

A process for synthesizing isooctyl nitrate in a continuous flow reactor comprises flowing a H2SO4-HNO3 mixture within a flow reactor, flowing isooctyl alcohol into said flow reactor so as to mix the isooctyl alcohol with the H2SO4-HNO3 mixture and produce a reaction mixture stream flowing in said reactor, maintaining the reaction mixture stream flowing in said flow reactor at a reaction temperature within in the range −10° to 35° C. inclusive, and wherein the residence time of the reaction mixture stream in the flow reactor is greater than or equal to 5 seconds and less than or equal to 40 seconds, and wherein the H2SO4 of the H2SO4-HNO3 mixture is H2SO4 having a concentration of in the range of 85 to 95% inclusive, more desirably 88 to 92% inclusive, most desirably of 90%.

First claim

What is claimed is:

1. A process for synthesizing isooctyl nitrate in a continuous flow reactor with 99% or greater conversion and 99% or greater yield, the process comprising:
flowing a H2SO4-HNO3 mixture within a flow reactor;
flowing isooctyl alcohol into said flow reactor so as to mix the isooctyl alcohol with the H2SO4-HNO3 mixture and produce a reaction mixture stream flowing in said reactor;
maintaining the reaction mixture stream flowing in said flow reactor at a reaction temperature within in the range −10° to 35° C. inclusive,
wherein the residence time of the reaction mixture stream in the flow reactor is in the range of 5 to 40 seconds, inclusive, and wherein the H2SO4 of the H2SO4-HNO3 mixture is 90% H2SO4.

2. The process according to claim 1 wherein the step of flowing a H2SO4-HNO3 mixture within a flow reactor comprises flowing a H2SO4 stream into a first inlet of the flow reactor and flowing a HNO3 stream into a second inlet of the flow reactor so as to mix the H2SO4 stream with the HNO3 stream and produce the mixed H2SO4-HNO3 stream flowing within said flow reactor.

3. The process according to claim 1 wherein the step of flowing a H2SO4-HNO3 mixture within a flow reactor comprises bringing the H2SO4-HNO3 mixture to, or maintaining the H2SO4-HNO3 mixture at, a temperature within the range of from −10° to 35° C. inclusive, while flowing the H2SO4-HNO3 mixture within the flow reactor.

4. The process according to claim 3 , wherein the step of flowing isooctyl alcohol into said flow reactor further comprises bringing the isooctyl alcohol to, or maintaining the isooctyl alcohol at, a temperature within the range of from −10° to 35° C. inclusive, while flowing the isooctyl alcohol within the flow reactor.

5. The process according to claim 4 , wherein the step of flowing isooctyl alcohol into said flow reactor so as to mix the isooctyl alcohol with the H2SO4-HNO3 mixture comprises flowing the reaction mixture stream within a passage having varying shape all along the length thereof so as to induce mixing throughout the duration of the residence time.

6. The process according to claim 1 , wherein the step of flowing isooctyl alcohol into said flow reactor so as to mix the isooctyl alcohol with the H2SO4-HNO3 mixture comprises flowing the reaction mixture stream within a passage of varying shape all along the length thereof so as to induce mixing throughout the duration of the residence time.

7. The process according to claim 1 , wherein the step of flowing a H2SO4-HNO3 mixture within a flow reactor comprises flowing a H2SO4-HNO3 mixture within a glass, glass-ceramic, or ceramic flow reactor.

8. The process according to claim 1 wherein the step of flowing a H2SO4-HNO3 mixture within a flow reactor comprises flowing at an acid mixture flow rate, the step of flowing isooctyl alcohol comprises flowing at an alcohol flow rate, and wherein said acid mixture flow rate and said alcohol flow rate result in a molar ratio of H2SO4 to isooctyl alcohol, in the reaction mixture stream, within the range of 1.5:1 to 2:1 inclusive.

9. The process according to claim 8 wherein the acid mixture flow rate and the alcohol flow rate result in a molar ratio of HNO3 to isooctyl alcohol, in the reaction mixture stream, of 1:1.

10. The process according to claim 8 wherein the alcohol flow rate is within the range of 0.25 to 16 moles per minute, inclusive.

11. The process according to claim 1 wherein the step of maintaining the reaction mixture stream flowing in said flow reactor within the range of from −10° to 35° C. inclusive comprises maintaining the reaction mixture stream flowing in said flow reactor at a temperature in the range of from 5 to 15° C., inclusive, and wherein the residence time of the reaction mixture stream in the flow reactor is greater than or equal to 10 seconds and less than or equal to 20 seconds.

12. The process according to claim 1 wherein the conversion is 100% and the yield is greater than 99.5%.

13. The process according to claim 1 , wherein the process further comprises:
capturing post-reaction H2SO4; and
reusing the captured H2SO4 in the H2SO4-HNO3 mixture.

Assignees

• Corning Inc

Inventors

• Ma Bing
• Shen Wei
• Wang Yanhua
• Zhang Mo

Classifications

• C07C201/02 Primary

  Preparation of esters of nitric acid · CPC title

• C07C203/04

  having nitrate groups bound to acyclic carbon atoms · CPC title