Continuous carbonylation processes

Patent metadata

Field	Value
Publication number	US-10738022-B2
Application number	US-201916248509-A
Country	US
Kind code	B2
Filing date	Jan 15, 2019
Priority date	Feb 13, 2015
Publication date	Aug 11, 2020
Grant date	Aug 11, 2020

Abstract

Provided are processes for monitoring and maintaining continuous carbonylation of epoxides or lactones. Processes include measuring parameters affecting the rate of the carbonylation reaction and adding supplemental replacement catalyst replacement components to maintain a constant rate of carbonylation.

First claim

What is claimed is:

1. A process for continuous carbonylation of an epoxide or lactone feedstock, comprising:
forming an initial load of a carbonylation catalyst in situ in a carbonylation reaction vessel from (i) a Lewis acid precursor feed stream comprising a Lewis acid precursor or a Lewis acid and (ii) a metal carbonyl precursor feed stream comprising a metal carbonyl precursor or a metal carbonyl, wherein the carbonylation catalyst comprises the Lewis acid and the metal carbonyl;
continuously reacting an epoxide or lactone feedstock with carbon monoxide in the presence of the carbonylation catalyst in the carbonylation reaction vessel,
wherein, at a start time of the process, the carbonylation reaction vessel contains an initial concentration of the Lewis acid and an initial concentration of the metal carbonyl; and
adding to the carbonylation reaction vessel, at a time after the start time of the process, a first catalyst replacement component using the Lewis acid precursor feed stream, and a second catalyst replacement component using the metal carbonyl precursor feed stream,
wherein the first catalyst replacement component is the Lewis acid precursor or the Lewis acid,
the second catalyst replacement component is the metal carbonyl precursor or the metal carbonyl; the depletion of the Lewis acid and the depletion of the metal carbonyl do not occur at the same rate, the Lewis acid precursor corresponds to one of the formulas:

wherein:

is a multidentate ligand;

is a multidentate ligand system capable of coordinating both metal atoms;
M is a metal atom coordinated to the multidentate ligand;
M 1 is a first metal atom;
M 2 is a second metal atom; and

Rq is independently selected from C 1-12 aliphatic and optionally substituted aryl, wherein M, M 1 and M 2 are any metal atom selected from the periodic table groups 2-13, and the metal carbonyl precursor is a neutral or ionic metal carbonyl compound corresponding to the formula Q d M′ e (CO) w′ wherein
Q is any ligand,
M′ is a metal atom,
d is an integer between 0 and 8 inclusive;
e is an integer between 1 and 6 inclusive;
and w′ is a number such as to provide the stable neutral metal carbonyl complex, wherein M′ is any metal atom selected from the periodic table groups 1, 2 and 4-9.

2. The process of claim 1 , wherein the first catalyst replacement component, or the second catalyst replacement component, or both, is added at different times or at different rates to the carbonylation reaction vessel.

3. The process of claim 1 , wherein the Lewis acid precursor feed stream and the metal carbonyl precursor feed stream each independently comprises solvent.

4. The process of claim 1 , wherein the Lewis acid precursor feed stream and the metal carbonyl precursor feed stream each independently comprises organic solvent.

5. The process of claim 1 , wherein the Lewis acid precursor feed stream and the metal carbonyl precursor feed stream each independently comprises aliphatic hydrocarbons, aromatic hydrocarbons, halogenated solvents, ethers, esters, ketones, nitriles, amides, carbonates, alcohols, amines, or sulfones, or any mixtures thereof.

6. The process of claim 1 , wherein the Lewis acid precursor feed stream and the metal carbonyl precursor feed stream each independently comprises one or more ethers.

7. The process of claim 1 , wherein the Lewis acid precursor feed stream and the metal carbonyl precursor feed stream each independently comprises diethyl ether, methy-t-butyl ether, tetrahydrofuran, 1,4-dioxane, glyme, diglyme, triglyme, or higher glymes, or any mixtures thereof.

8. The process of claim 1 , wherein the Lewis acid precursor feed stream comprises a homogenous solution of the Lewis acid or the Lewis acid precursor in organic solvent.

9. The process of claim 1 , wherein the Lewis acid precursor feed stream comprises a slurry of the Lewis acid or the Lewis acid precursor in organic solvent.

10. The process of claim 1 , wherein the metal carbonyl precursor feed stream comprises a homogenous solution of the metal carbonyl or the metal carbonyl precursor in organic solvent.

11. The process of claim 1 , wherein the metal carbonyl precursor feed stream comprises a slurry of the metal carbonyl or the metal carbonyl precursor in organic solvent.

12. The process of claim 1 , wherein the depletion of the Lewis acid, or the depletion of the metal carbonyl, or both, in the carbonylation reaction vessel is determined by: measuring one or more parameters selected from the group consisting of:
i-a) a concentration of the Lewis acid in the carbonylation reaction vessel;
i-b) a concentration of a decomposition product of the Lewis acid in the carbonylation reaction vessel;
ii-a) a concentration of the Lewis acid in a process stream downstream from the carbonylation reaction vessel;
ii-b) a concentration of a decomposition product of the Lewis acid in a process stream downstream from the carbonylation reaction vessel;
iii-a) a concentration of the metal carbonyl in the carbonylation reaction vessel;
iii-b) a concentration of a decomposition product of the metal carbonyl in the carbonylation reaction vessel;
iv-a) a concentration of the metal carbonyl in a process stream downstream from the carbonylation reaction vessel;
iv-b) a concentration of a decomposition product of the metal carbonyl in a process stream downstream from the carbonylation reaction vessel; and
v) a rate of the carbonylation reaction; and
obtaining a measured value of the one or more parameters.

Assignees

• Novomer Inc

Inventors

• Farmer Jay J
• Galebach Peter
• Sherry Kyle
• Sookraj Sadesh H

Classifications

• C07D307/60 Primary

  Two oxygen atoms, e.g. succinic anhydride · CPC title

• C07D305/12 Primary

  Beta-lactones · CPC title

• C07C69/67

  of saturated acids · CPC title

• C07C67/37

  by reaction of ethers with carbon monoxide · CPC title

• B01J31/00

  Catalysts comprising hydrides, coordination complexes or organic compounds (catalyst compositions used only in polymerisation reactions C08 {; catalytic antibodies C12N9/0002}) · CPC title