Methods of using N-oxyl polymerization inhibitor in a wash settler for preparing methyl methacrylate

Patent metadata

Field	Value
Publication number	US-10640449-B2
Application number	US-201716466849-A
Country	US
Kind code	B2
Filing date	Dec 8, 2017
Priority date	Dec 20, 2016
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

The present invention provides methods comprising washing or, preferably, washing and neutralizing a sulfur acid containing crude MMA stream to generate a two phase stream containing at least methacrylic acid, methacrylamide (MAM), water and methanol, and an organic component containing methyl methacrylate and thereby form an aqueous component; including in any of the organic component, the aqueous component of a neutralized sulfur acid containing crude methyl methacrylate (MMA) stream or the organic component of a neutralized sulfur acid containing crude methyl methacrylate (MMA) stream one or more N-oxyl compound polymerization inhibitor; followed by separating the aqueous component from the organic component, thereby forming a treated crude MMA stream and an aqueous stream to remove residual (meth) acrylic acid.

First claim

We claim:

1. A method for removing methacrylic acid (MAA) from a sulfur acid containing crude methyl methacrylate (MMA) stream which contains methacrylic acid, methacrylamide (MAM), methanol, and a sulfur acid salt and contains an organic component containing methyl methacrylate, the method comprising:
including in the organic component of the sulfur acid containing crude MMA stream one or more N-oxyl compound polymerization inhibitor.

2. The method as claimed in claim 1 , wherein the sulfur acid salt is a sulfuric acid salt or a sulfonic acid salt, and the salt is an ammonia, or alkali metal salt.

3. The method as claimed in claim 1 , further comprising:
neutralizing the sulfur acid containing crude MMA stream to generate a two phase stream having a neutralized aqueous component containing at least the sulfur acid salt, a methacrylic acid salt, methacrylamide (MAM), water and methanol, and an organic component containing methyl methacrylate, followed by;
including in the neutralized aqueous component, or the organic component, or both, one or more N-oxyl compound polymerization inhibitor effective in both the aqueous component and the organic component, followed by;
separating the neutralized aqueous component from the organic component, thereby forming a treated crude MMA stream and, separately, a neutralized aqueous stream which comprises a methacrylate salt.

4. The method as claimed in claim 1 , wherein the polymerization inhibitor is 4-hydroxy-2, 2, 6, 6-tetramethylpiperidinoxyl (4-HT).

5. The method as claimed in claim 3 , wherein the including of the polymerization inhibitor further comprises adding a second inhibitor chosen from hydroquinones; aromatic amines; thiazine containing compounds; nitrosophenols; 4-hydroxy-2,3,6,6-tetramethylpiperidine; and mixtures thereof, to the neutralized aqueous component, to the organic component, or to both.

6. The method as claimed in claim 3 , wherein the neutralizing comprises adding aqua ammonia to the two-phase feed stream and the resulting pH ranges from 6 to 10.

7. The method as claimed in claim 3 , wherein the amount of the N-oxyl compound polymerization inhibitor added to the neutralized aqueous component, to the organic component, or to both, ranges from 10 to 5000 ppm, based on the total weight of the component to which it is added and the total polymerization inhibitor.

8. The method as claimed in claim 3 , wherein neutralizing comprises adding aqueous ammonia, the method further comprising removing the neutralized aqueous stream comprising methanol, MAM and ammonium methacrylate (NH 4+ MAA − ) after separating the organic component and the neutralized aqueous component of the two phase stream, thereby providing the treated crude MMA stream.

9. The method as claimed in claim 3 , further comprising washing the treated crude MMA stream that contains the N-oxyl inhibitor a second time with water, or multiple times with water, following by including additional N-oxyl compound polymerization inhibitor after each successive washing.

10. The method as claimed in claim 1 , wherein, wherein the sulfur acid containing crude MMA stream contains less than 1000 ppm of an azeotroping solvent or entraining solvent.

Assignees

• Dow Global Technologies Llc
• Rohm & Haas

Inventors

• Atkins Joseph
• Maillot Philippe P
• Mendoza Joy L
• Sopchik Alan E
• Ye Mingyu

Classifications

• C07C67/58

  by liquid-liquid treatment · CPC title

• C07C67/62 Primary

  Use of additives, e.g. for stabilisation · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title