Flow-through reactors for the continuous quenching of peroxide mixtures and methods comprising the same

Patent metadata

Field	Value
Publication number	US-10668446-B2
Application number	US-201716081819-A
Country	US
Kind code	B2
Filing date	Jun 21, 2017
Priority date	Jun 21, 2016
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

This disclosure relates to a highly efficient and safe reactor for the continuous quenching of peroxide mixtures generated during the reaction of unsaturated compounds with ozone, which minimizes the amount of highly reactive peroxides accumulated in the reactor at any given time. The reactor may be modified to allow for expansion to accommodate the quenching parameters of a wide variety of ozonolysis reactions and flow rates. The reactor may be constructed from highly pressure rated stainless steel for maximum durability, safety, and economic practicality while increasing the safety of peroxide quenching, thus allowing tighter process control and improved product yields. This disclosure also related to methods for quenching ozonides.

First claim

What is claimed is:

1. A reactor for the continuous quenching of a peroxide mixture (PM), wherein said reactor is either a single-pass flow-through reactor or a recirculating flow-through reactor, said reactor comprising:
(a) either (1) a single input for both a peroxide mixture (PM) and a peroxide quenching solution (PQS), or (2) a first input for a PM and a second input for a PQS;
(b) an output for a quenched product solution (QPS);
(c) a heat exchanger (HE); and
(d) optionally, a circulatory pump (CP);
the output for the quenched product solution (QPS) has a flow rate out of the reactor, F out , of 80 to about 1,000,000 mL/minute, and wherein the overall pressure in the reactor is 1 psi to 6000 psi, and wherein the heat exchanger maintains the reactor temperature at −78° C. to 300° C.;
wherein the reactor is placed in line with a continuous ozonolysis operation from a tubular falling film reactor system with one or multiple tubes wherein the combined ozone and carrier gas flow is co-current; and
wherein the reactor is designed to provide an overall peroxide concentration in the quenched product solution (QPS) upon exiting the reactor of less than or equal to 100 mmol/L as determined by iodometric titration when the overall peroxide concentration in the peroxide mixture (PM) prior to entering the reactor is 500 to 2000 mmol/L as determined by iodometric titration.

2. The reactor of claim 1 , wherein the reactor is a single-pass flow-through reactor and the reactor further comprises:
a second single-pass flow-through reactor connected to the first single-pass flow-through reactor, said second reactor optionally comprising a circulatory pump (CP), heat exchanger (HE), or both.

3. The reactor of claim 1 , wherein the reactor is a single pass-flow through reactor.

4. The reactor of claim 1 , wherein the reactor is a recirculating flow-through reactor.

5. The reactor of claim 4 , wherein the reactor has
a first input for a peroxide mixture (PM); and a
a second input for a peroxide quenching solution (PQS).

6. The reactor of claim 1 , wherein the reactor has a diameter of 0.25 inches to 10 inches.

7. The reactor of claim 1 , wherein the reactor has a length of 5 m to 200 m.

8. The reactor of claim 1 , wherein the reactor is designed to provide the peroxide mixture (PM) with a residence time in the reactor of from 1 to 200 minutes.

9. The reactor of claim 1 , wherein the heat exchanger (HE) maintains the temperature in the reactor at −40° C. to 150° C.

10. The reactor of claim 1 , wherein the reactor is designed to provide that the peroxide quenching solution (PQS) quenches the peroxide mixture (PM) oxidatively.

11. The reactor of claim 1 , wherein the reactor is designed to provide that the peroxide quenching solution (PQS) quenches the peroxide mixture (PM) reductively.

12. The reactor of claim 4 , wherein the reactor is designed to provide that the peroxide mixture (PM) and the peroxide quenching solution (PQS) are recirculated through the reactor 1, 2, 3, or 4 times before collecting the quenched product solution (PQS) from the output.

13. A method of continuously quenching a peroxide mixture (PM) in a reactor according to claim 1 .

14. A method of continuously quenching a peroxide mixture (PM) in a reactor according to claim 4 .

15. The method of claim 13 , wherein the peroxide mixture (PM) is derived from any C 4 -C 50 unsaturated material.

16. The method of claim 13 , wherein the peroxide mixture (PM) is derived from a terpene, or a fatty acid ester, or a fatty acid, or a vegetable oil.

17. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified C 4 -C 50 unsaturated material with a gaseous reagent comprising ozone and one or more carrier gases to generate a peroxide mixture (PM), followed by the continuous quenching of the peroxide mixture (PM), comprising:
a) feeding the liquid or emulsified C 4 -C 50 unsaturated material from a common liquid or emulsified C 4 -C 50 unsaturated material feeding chamber that is maintained completely full through annular slots and into a plurality of parallel and substantially identical tubes, as to form a liquid or emulsified reagent film comprising the C 4 -C 50 unsaturated material on the internal surface of each tube;
(b) feeding the gaseous reagent through the annular slots and into the tubes from a gaseous reagent feeding chamber to generate a peroxide mixture (PM), the feeding pressure of the gaseous reagent being substantially the same as the pressure loss from the gaseous reagent flow-through the tubes containing the liquid or emulsified reagent film comprising the C 4 -C 50 unsaturated material, but less than the feeding pressure of the liquid or emulsified C 4 -C 50 unsaturated material;
(c) cooling the tubes by flowing a liquid coolant through a housing surrounding the tubes;
(d) feeding the peroxide mixture (PM) and a peroxide quenching solution (PQS) into a peroxide mixture (PM) and peroxide quenching solution (PQS) feeding chamber;
(e) feeding the peroxide mixture (PM) and peroxide quenching solution (PQS) into a reactor according to claim 1 .

18. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified C 4 -C 50 unsaturated material with a gaseous reagent comprising ozone and one or more carrier gases to generate a peroxide mixture (PM), followed by the continuous quenching of the peroxide mixture (PM), comprising:
(a) feeding the liquid or emulsified C 4 -C 50 unsaturated material from a common liquid or emulsified C 4 -C 50 unsaturated material feeding chamber that is maintained completely full through annular slots and into a plurality of parallel and substantially identical tubes, as to form a liquid or emulsified reagent film comprising the C 4 -C 50 unsaturated material on the internal surface of each tube;
(b) feeding the gaseous reagent through the annular slots and into the tubes from a gaseous reagent feeding chamber to generate a peroxide mixture (PM), the feeding pressure of the gaseous reagent being substantially the same as the pressure loss from the gaseous reagent flow-through the tubes containing the liquid or emulsified reagent film comprising the C 4 -C 50 unsaturated material, but less than the feeding pressure of the liquid or emulsified C 4 -C 50 unsaturated material;
(c) cooling the tubes by flowing a liquid coolant through a housing surrounding the tubes;
(d) feeding the peroxide mixture (PM) into a reactor according to claim 4 .

Assignees

• P2 Science Inc

Inventors

• Foley Patrick
• Chapeaux Alexandre
• Milicia Antonio
• Adami Icilio

Classifications

• B01J2219/00792

  One or more tube-shaped elements · CPC title

• B01J2219/00889

  Mixing · CPC title

• B01J2219/00795

  Spiral-shaped · CPC title

• B01J2219/00873

  Heat exchange · CPC title

• C07D493/18

  Bridged systems · CPC title