Methods of producing para-xylene and terephthalic acid
AssigneeMicromidas, Inc.
InventorsMakoto N. Masuno, Douglas Cannon, John Bissell, II, Ryan L. Smith, Alex B. Wood, Patrick B. Smith, Dennis A. Hucul, Katherine Brune
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Abstract
The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose) and ethylene in the presence of an acid, such as a Lewis acid. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF) and 2-methylfuran, which may be converted into para-xylene and toluene, respectively. In particular, para-xylene can then be oxidized to form terephthalic acid.
Claims44
A method for producing para-xylene, comprising:
- combining 2,5-dimethylfuran with ethylene and a catalyst to form a reaction mixture, wherein the catalyst comprises a metal cation and a triflate counterion, and wherein the metal cation is a Group 3 metal cation, a Group 9 metal cation, a Group 10 metal cation, a Group 11 metal cation, or a lanthanide series metal cation;
- and
- producing para-xylene from at least a portion of the 2,5-dimethylfuran and at least a portion of the ethylene in the reaction mixture.
A method for producing a compound of formula I, wherein formula I has the structure:
- wherein each R1 and R2 is independently hydrogen or alkyl, wherein the method comprises:
- combining a compound of formula II with ethylene and a catalyst to form a reaction mixture,
- wherein the compound of formula II is:
- wherein R1 and R2 are as defined for formula I above, and
- wherein the catalyst comprises a metal cation and a triflate counterion, and wherein the metal cation is a Group 3 metal cation, a Group 9 metal cation, a Group 10 metal cation, a Group 11 metal cation, or a lanthanide series metal cation;
- and
- producing a compound of formula I from at least a portion of the compound of formula II and at least a portion of the ethylene in the reaction mixture.
Dependencies are inferred from the claim text.