Michael G Milner

US Patent:

20170050167, Feb 23, 2017

Filed:

Nov 8, 2016

Appl. No.:

15/345976

Inventors:

- Loveland OH, US
Adam Gregg Malofsky - Loveland OH, US
Jeffrey M. Sullivan - Goshen OH, US
Philip B. Kisanga - Mason OH, US
John Joseph Anderson - Mount Vernon IN, US
Michael Charles Milner Cockrem - Madison WI, US
Philip Jay Carlberg - Loveland OH, US

International Classification:

B01J 19/24
B01J 29/40
B01J 8/06

Abstract:

Method to obtain methylene malonate and related monomers following a bis(hydroxymethyl) malonate pathway. A bis(hydroxymethyl) malonate intermediary is subsequently reacted (i.e., subjected to thermolysis) to provide a methylene malonate monomer species. A source of formaldehyde (e.g., formalin) is provided in the presence of a basic catalyst (e.g., calcium hydroxide), to which a malonate (e.g., diethyl malonate) is added under suitable reaction conditions to obtain the desired intermediary (e.g., dialkyl bis(hydroxymethyl) malonate). The intermediary is reacted (i.e., subjected to thermolysis) under suitable conditions in the presence of a suitable catalyst (e.g., a zeolite) to obtain a methylene malonate monomer. In an exemplary embodiment, the thermolysis reaction includes the addition of the bis(hydroxymethyl) malonate intermediary onto a heated catalyst. The reaction product is collected and purified. The disclosed methods may be performed in a continuous operation. Discrete steps may be performed by using modular units within a plant.

US Patent:

20150343415, Dec 3, 2015

Filed:

Aug 11, 2015

Appl. No.:

14/823581

Inventors:

- Loveland OH, US
Adam Gregg Malofsky - Loveland OH, US
Jeffrey M. Sullivan - Goshen OH, US
Philip B. Kisanga - Mason OH, US
John Joseph Anderson - Mount Vernon IN, US
Michael Charles Milner Cockrem - Madison WI, US
Philip Jay Carlberg - Loveland OH, US

International Classification:

B01J 19/24
B01J 8/06

Abstract:

Method to obtain methylene malonate and related monomers following a bis(hydroxymethyl) malonate pathway. A bis(hydroxymethyl) malonate intermediary is subsequently reacted (i.e., subjected to thermolysis) to provide a methylene malonate monomer species. A source of formaldehyde (e.g., formalin) is provided in the presence of a basic catalyst (e.g., calcium hydroxide), to which a malonate (e.g., diethyl malonate) is added under suitable reaction conditions to obtain the desired intermediary (e.g., dialkyl bis(hydroxymethyl) malonate). The intermediary is reacted (i.e., subjected to thermolysis) under suitable conditions in the presence of a suitable catalyst (e.g., a zeolite) to obtain a methylene malonate monomer. In an exemplary embodiment, the thermolysis reaction includes the addition of the bis(hydroxymethyl) malonate intermediary onto a heated catalyst. The reaction product is collected and purified. The disclosed methods may be performed in a continuous operation. Discrete steps may be performed by using modular units within a plant.

US Patent:

20150218081, Aug 6, 2015

Filed:

Mar 3, 2015

Appl. No.:

14/636402

Inventors:

- Loveland OH, US
Adam Gregg Malofsky - Loveland OH, US
Jeffrey M. Sullivan - Goshen OH, US
Philip B. Kisanga - Mason OH, US
John Joseph Anderson - Mount Vernon IN, US
Michael Charles Milner Cockrem - Madison WI, US
Philip Jay Carlberg - Loveland OH, US

International Classification:

C07C 67/327
C07C 67/56
B01J 29/40
C07C 67/31
C07C 69/593

Abstract:

Method to obtain methylene malonate and related monomers following a bis(hydroxymethyl) malonate pathway. A bis(hydroxymethyl) malonate intermediary is subsequently reacted (i.e., subjected to thermolysis) to provide a methylene malonate monomer species. A source of formaldehyde (e.g., formalin) is provided in the presence of a basic catalyst (e.g., calcium hydroxide), to which a malonate (e.g., diethyl malonate) is added under suitable reaction conditions to obtain the desired intermediary (e.g., dialkyl bis(hydroxymethyl) malonate). The intermediary is reacted (i.e., subjected to thermolysis) under suitable conditions in the presence of a suitable catalyst (e.g., a zeolite) to obtain a methylene malonate monomer. In an exemplary embodiment, the thermolysis reaction includes the addition of the bis(hydroxymethyl) malonate intermediary onto a heated catalyst. The reaction product is collected and purified. The disclosed methods may be performed in a continuous operation. Discrete steps may be performed by using modular units within a plant.