# US 11,111,204 B2 · Method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst

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- Number: US 11,111,204 B2
- Document ID: US11111204B2
- Status: Granted
- Kind: B2
- Application number: 16/959,232
- Filed: 2018-12-13
- Published: 2020-10-22
- Granted: 2021-09-07
- Earliest claimed: 2018-01-10
- Assignees: Dow Global Technologies LLC; Rohm and Haas Company
- Applicants: Dow Global Technologies LLC; Rohm and Haas Company
- Inventors: Christopher D. Frick; Jeffrey A. Herron; Kirk W. Limbach; Wen Sheng Lee; Victor J. Sussman
- Web page: https://patentgrep.com/patent/US11111204B2

## CPC

- C07C 67/39: by oxidation of groups which are precursors for the acid moiety of the ester
- B01J 21/063: {Titanium; Oxides or hydroxides thereof}
- B01J 21/08: Silica
- B01J 23/002: {Mixed oxides other than spinels, e.g. perovskite}
- B01J 23/44: Palladium
- B01J 23/52: Gold
- B01J 35/397: {Egg shell like}
- B01J 35/40: characterised by dimensions, e.g. grain size (in a colloidal state B01J35/23; crystallite size B01J35/77)
- B01J 37/0205: {in several steps}
- B01J 37/088: {Decomposition of a metal salt}
- B01J 19/1812: {Tubular reactors}
- C07C 69/54: Acrylic acid esters; Methacrylic acid esters
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A method for preparing methyl methacrylate from methacrolein and methanol; said method comprising contacting a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein said support comprises silicon, and wherein said catalyst comprises from 0.1 to 40 mol % titanium and from 0.1 to 10 mol % of at least one noble metal.

## Claims

### Claim 1

A method for preparing methyl methacrylate from methacrolein and methanol; said method comprising contacting a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein said support comprises silicon, and wherein said catalyst comprises from 0.1 to 40 mol % titanium and from 0.1 to 10 mol % of at least one noble metal selected from the group consisting of gold, platinum, iridium, osmium, silver, palladium, rhodium, and ruthenium, wherein mole percentages are based on total moles of silicon atoms and metal atoms, wherein at least 90 wt % of the noble metal is in the outer 60% of catalyst volume.

### Claim 2 (depends on 1)

The method of claim 1 in which the noble metal is selected from the group consisting of gold, palladium and combinations thereof.

### Claim 3 (depends on 1)

The method of claim 1 in which the catalyst has an average diameter from 60 microns to 10 mm.

### Claim 4 (depends on 1)

The method of claim 1 in which the catalyst comprises 0.1 to 8 mol % of at least one noble metal, 60 to 95 mol % silicon, 0.1 to 20 mol % titanium and 0.1 to 20 mol % alkali metal or alkaline earth metal.

### Claim 5 (depends on 1)

The method of claim 1 in which the support is silica.

### Claim 6 (depends on 1)

The method of claim 1 in which the noble metal is gold.

### Claim 7 (depends on 1)

The method of claim 1 in which the catalyst is contained in a catalyst bed.

### Claim 8 (depends on 7)

The method of claim 7 in which methanol and methacrolein are fed to a reactor containing the catalyst bed in a molar ratio from 1:1 to 10:1, respectively.

### Claim 9 (depends on 8)

The method of claim 8 in which the reactor is a tubular continuous reactor.