Furan-2,5-dicarboxylic acid purge process

Patent metadata

Field	Value
Publication number	US-10882032-B2
Application number	US-201615217319-A
Country	US
Kind code	B2
Filing date	Jul 22, 2016
Priority date	Jul 20, 2012
Publication date	Jan 5, 2021
Grant date	Jan 5, 2021

Abstract

Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.

First claim

We claim:

1. A process for producing a carboxylic acid composition, said process comprising:
oxidizing, in a primary oxidation zone, at least one oxidizable compound comprising at least one selected from the group consisting of 5-(hydroxymethyl)furfural (5-HMF), 5-(chloromethyl)furfural (5-CMF), 2,5-dimethylfuran (2,5-DMF), 5-HMF esters (5-R(CO)OCH 2 -furfural where R=alkyl, cycloalkyl and aryl), 5-HMF ethers (5-R′OCH 2 -furfural, where R′=alkyl, cycloalkyl and aryl), 5-alkyl furfurals (5-R″-furfural, where R″=alkyl, cycloalkyl and aryl), alkylcarboxylate of methyfuran (5-R′″O(CO)-methylfuran, where R′″=alkyl, cycloalkyl), alkylcarboxylate of alkoxyfuran (5-R″″O(CO)—OR′″″furan, where R″″=alkyl, cycloalkyl and aryl and R′″″=alkyl, cycloalkyl and aryl), mixed feed-stocks of 5-HMF and 5-HMF esters and mixed feed-stocks of 5-HMF and 5-HMF ethers, mixed feed-stocks of 5-HMF and 5-alkyl furfurals, mixed feed-stocks of 5-HMF and 5-CMF, mixed feed-stocks of 5-HMF and 2,5-DMF, mixed feed-stocks of 5-HMF and alkylcarboxylate of methyfuran, mixed feed-stocks of 5-HMF and alkylcarboxylate of alkoxyfuran, in the presence of a solvent stream, an oxidizing gas, and a catalyst system at a temperature of about 110° C. to about 220° C. to produce said carboxylic acid composition comprising furandicarboxylic acid (FDCA) at a yield of 80% or more;
isolating, washing, and dewatering solids present in said carboxylic acid composition in a solid-liquid separation zone to generate a wet cake stream comprising FDCA and a mother liquor stream comprising the oxidation solvent, the catalyst system, and impurities; and routing a portion of the mother liquor stream to a mother liquor purge zone;
wherein the mother liquor purge zone comprises an evaporative step to separate the oxidation solvent from the mother liquor stream by evaporation;
wherein said primary oxidation zone comprises at least one oxidation reactor;
wherein at least one of said oxidation reactor is a reactor that was utilized in a commercial terephthalic acid process;
wherein said catalyst system comprises cobalt in a range from about 700 ppm to about 4500 ppm by weight with respect to the weight of the liquid in said primary oxidation zone, manganese in an amount ranging from about 20 ppm by weight to about 400 ppm by weight with respect to the weight of the liquid in said primary oxidation zone and bromine in an amount ranging from about 700 ppm by weight to about 4000 ppm by weight with respect to the weight of the liquid in said primary oxidation zone; wherein the weight ratio of cobalt to manganese in the reaction mixture is from about 10 to about 400 and the weight ratio of cobalt to bromine is from about 0.7 to about 3.5.

2. A process according to claim 1 wherein said oxidation reactor comprises a bubble column.

3. A process according to claim 1 wherein said oxidizing is conducted at a temperature from about 105° C. to about 180° C.

4. A process according to claim 2 wherein said oxidizing is conducted at a temperature from about 100° C. to about 160° C.

5. A process according to claim 1 wherein said oxidizing is conducted at a pressure from about 50 psig to about 1000 psig.

Assignees

• Eastman Chem Co

Inventors

• Fontenot Kevin John
• Janka Mesfin Ejerssa
• Parker Kenny Randolph
• Shaikh Ashfaq Shahanawaz
• Partin Lee Reynolds
• Sumner Jr Charles Edwan
• Kirk Shane Kipley
• Moody Paula
• Bowers Bradford Russell
• Morrow Michael Charles

Classifications

• C07B63/00

  Purification; Separation (separation of optically-active compounds C07B57/00); Stabilisation; Use of additives · CPC title

• B01D17/00

  Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion (devices for separating or removing fatty or oily substances or similar floating material from water, waste water, or sewage C02F1/40; cleaning or keeping clear the surface of open water from oil or like materials E02B15/04; arrangements for separating lubricants from refrigerants F25B43/02) · CPC title

• B01J27/128

  with iron group metals or platinum group metals · CPC title

• B01J27/32 Primary

  of catalysts comprising compounds of halogens · CPC title

• B01D11/0446

  Juxtaposition of mixers-settlers · CPC title