Source: https://patents.google.com/patent/US9505692B2/en
Timestamp: 2019-04-26 07:14:56
Document Index: 471527909

Matched Legal Cases: ['Application No. 2', 'application No. 2009801437997', 'Application No. 201102625', 'Application No. 2015', 'Application No. 200980143799', 'Application No. 200980143799', 'Application No. 2011', 'Application No. 2011', 'Application No. 09']

US9505692B2 - Dicarboxylic acid production with self-fuel oxidative destruction - Google Patents
Dicarboxylic acid production with self-fuel oxidative destruction Download PDF
US9505692B2
US9505692B2 US12/556,099 US55609909A US9505692B2 US 9505692 B2 US9505692 B2 US 9505692B2 US 55609909 A US55609909 A US 55609909A US 9505692 B2 US9505692 B2 US 9505692B2
US12/556,099
US20100113824A1 (en
Raymond Elbert Fogle, III
2009-09-09 Application filed by Grupo Petrotemex de C V SA filed Critical Grupo Petrotemex de C V SA
2009-10-22 Priority claimed from RU2011121839/04A external-priority patent/RU2575118C2/en
2009-11-05 Assigned to EASTMAN CHEMICAL COMPANY reassignment EASTMAN CHEMICAL COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SHEPPARD, RONALD BUFORD, UPSHAW, TIMOTHY ALAN, FOGLE III, RAYMOND ELBERT, WONDERS, ALAN GEORGE
2010-05-06 Publication of US20100113824A1 publication Critical patent/US20100113824A1/en
2016-11-29 Publication of US9505692B2 publication Critical patent/US9505692B2/en
The invention provides improved energy content in and shaft power recovery from off-gas from xylene oxidation reactions while at the same time minimizing wastewater treatment cost. More shaft power is produced using off-gas than is required to drive the main air compressor, even with preferred, relatively low oxidation temperatures. Simultaneously, an amount of wastewater greater than byproduct water from oxidation of xylene is kept in vapor form and treated along with off-gas pollutants in a self-sustaining (self-fueling) gas-phase thermal oxidative destruction unit. Optionally, off-gas is combined from multiple xylene oxidation reactors, comprising primary and/or secondary oxidation reactors and forming TPA and/or IPA. Optionally, air compressor condensate and caustic scrubber blowdown are used in a TPA process or as utility water, effectively eliminating normal flow of liquid wastewater effluent from a TPA plant. Optionally, PET off-gas containing the water of PET formation is treated in a shared thermal oxidative destruction unit, effectively eliminating normal flow of liquid wastewater effluent from a combined pX-to-TPA-to-PET plant.
This application claims priority to U.S. Provisional Application Ser. No. 61/110,240, filed on Oct. 31, 2008, the disclosure of which is incorporated herein by reference in its entirety.
The term “water of TPA formation” is defined herein as 0.340 kilogram of water per kilogram of commercial purity pX feed. This comes from the intended reaction forming TPA from pX according to the stoichiometry: pX+3O2 yields TPA+2H2O. Notwithstanding that small amounts of impurities exist within commercial purity pX and that a small amount of pX is under-oxidized and/or over-oxidized, modern manufacturing facilities produce commercial purity pX comprising very low amounts of impurities and to convert such feed into crude and/or purified TPA with very high yields. Preferably the overall yield of TPA solid product, crude and/or purified, is at least about 96, or 97, or 98, or 99 mole percent based on the mass of commercial purity pX feed divided by a molecular weight of 106.16 grams per mole. Preferably, the commercial purity pX feed comprises at least about 0.990, or 0.995, 0.997, or 0.998 mass fraction of pX.
The inventions herein can be combined with the disclosures of US 20070293699 and US 20060047158 (the entire disclosures of which are incorporated herein by reference) for a preferred primary oxidation reaction medium, process, and means for converting pX to TPA, with a preferred oxidizer reactor being a bubble column reactor. These reference disclosures comprise numerous preferred mechanical features and process conditions for a primary oxidation, with process conditions notably including temperatures and gradients, pressures and gradients, flows, compositions and gradients, agitation, and residence times and distributions. The usages herein for “oxidizable compound”. “solvent”, “oxidant”, “reaction medium”, and “hydrocarbyl” are according to the above references.
It is preferred that filtrate solvent recovered from filtration and washing of solid TPA is returned to an oxidation reaction medium with elevated temperature provided by transfer of thermal energy through conductive, isolating, heat-exchange boundary surfaces. Filtrate solvent is solvent from mechanical separation and/or/or washing of solid TPA from a slurry. One means for obtaining filtrate solvent is filtration and washing of TPA slurry by any means known in the filtration art, but all other mechanical separations known in the art are contemplated by the inventors for producing filtrate solvent; e.g., gravity settling, centrifuges, hydroclones, and the like.
Accordingly, the inventors have discovered the following preferred embodiments for the present invention. After exiting a turboexpander, at least a portion of off-gas gas is bypassed around at least one off-gas condenser to form a “bypassed off-gas” using one or more of the following preferred aspects. It is preferred that said bypassed off-gas is cooled less than about 60, or 50, or 30, or 10° C. in a heat exchange means comprising conductive, isolating, heat-exchange boundary surfaces before combining with off-gas exiting an off-gas condenser, entering a TOD, and/or being released to ambient surroundings. It is preferred that said bypassed off-gas is at least about 1, or 2, or 4, or 8 weight percent of all off-gas exiting a turboexpander. It is preferred that said bypassed off-gas is less than about 50, or 40, or 30, or 20 weight percent of all off-gas exiting a turboexpander. It is preferred that the flow rate of said bypassed off-gas is used to adjust the amount of off-gas cooling in response to at least one process variable; e.g., temperature and/or pressure of condenser off-gas; temperature and/or flow rate of condenser liquid; chemical composition of either condenser off-gas an/or condensate by any on-line measurement, e.g., infrared compositional analysis. It is preferred that said bypassed off-gas is combined with at least a portion of off-gas that has exited an off-gas condenser to form a “mixed off-gas” before release to ambient surroundings. It is preferred that a “knock-out means” utilizing at least one of the following features processes at least a portion of condenser off-gas, thereby producing a “knock-out off-gas”. Preferably, at least about 10, 50, 98, 99.9 weight percent of the liquid entering said knock-out means is separated and exits commingled with less than about 50, or 95, or 99, or 99.8 weight percent of off-gas dinitrogen from an opening in the lower 80, or 60, or 40, or 10 percent of the height of said knock-out means. Preferably, at least a portion of said knock-out means is located at a lower elevation than at least one off-gas condenser providing gas-plus-liquid multiphase flow into said knock-out means. Preferably, liquid water exits said knock-out means from an opening located below a flow inlet from an off-gas condenser. Preferably, the superficial vertical velocity of off-gas in said knock-out means is less than about 4, or 3, or 2, or 1 meter per second at the plane of greatest horizontal diameter. Preferably, the superficial horizontal velocity of off-gas in said knock-out means is less than about 6, or 5, or 4, or 3 meters per second at the plane of greatest vertical diameter. Preferably, the mean residence time of off-gas in said knock-out means is less than about 20, or 13, or 8, or 5 seconds. Preferably, the mean residence time of off-gas in said knock-out means is at least about 0.5, or 1.0, or 1.5, or 2.0 seconds. Preferably, the mean residence time of liquid within said knock-out means is at least about 0.5, or 2, or 4, or 8 minutes. Preferably, the mean residence time of liquid within said knock-out means is less than about 60, or 48, or 24, or 12 minutes. Preferably, at least one liquid-removing impingement surface, other than pressure isolating boundary surfaces, is included within said knock-out means. Preferably, the solid surface area in contact with off-gas passing through a knock-out means is at least about 0.0005, or 0.001, or 0.002, or 0.004 square meters per kilogram of off-gas exiting said knock-out means. Preferably, at least a portion of off-gas passing through said knock-out means contacts at least about 0.001, or 0.005, or 0.01, or 0.02 square meters of non-pressure isolating solid surface area per kilogram of pX fed to corresponding oxidation reaction medium. Preferably at least about 70, or 80, or 90 percent of liquid droplets smaller than at least about 500, or 200, or 75, or 25 microns present in off-gas entering a knock-out means are removed from knock-out off-gas. The inventors disclose that these various preferred features for a knock-out means are preferred in a knock-out means processing condenser off-gas either with or without bypassed off-gas.
It is preferred that a TOD is self-fueled by oxidation of off-gas compounds comprising carbon monoxide and VOC, especially by oxidation of methyl acetate. It is preferred that the fuel content of off-gas is at least about 60, 70, 80, 90 percent of all fuel content entering TOD. Fuel content is evaluated as the heat of oxidation reactions yielding vapor phase products comprising water vapor and carbon dioxide gas. It is preferred that fuel content of off-gas is less than about 160, or 140, or 120, or 110 percent of the minimum fuel content needed to operate the TOD without a cooling means, e.g., sensible heating of air or other gas/vapor and/or sensible or latent heating of water or other liquid, whether directly by commingling mass or indirectly across isolating conductive heat exchange surfaces.
Undesirably with respect to energy recovery, the operating pressures and temperatures of secondary reaction mediums are often substantially different, sometimes significantly higher, from a primary reaction medium and/or from each other. The simple expansion of higher pressure reaction off-gases across a pressure reduction valve into lower pressure off-gas usually dissipates significant entropy, causing a loss in subsequent ability to produce shaft work. However, the present invention usefully retains enthalpy in the combined off-gases at the inlet to a turboexpander, and the combined off-gas flows usefully commingle CO and VOC fuel values ahead of a TOD.
1. A process for making terephthalic acid and/or isophthalic acid, said process comprising:
(a) oxidizing an aromatic compound in at least one oxidizer to thereby produce an oxidizer off-gas and an oxidizer product comprising terephthalic acid and/or isophthalic acid, wherein the at least one oxidizer comprises a bubble column reactor, and wherein the aromatic compound is at least one member selected from para-xylene and meta-xylene;
(b) directly or indirectly feeding at least a portion of said oxidizer offgas to a thermal oxidative (TOD) device, and
(c) oxidizing said at least a portion of the oxidizer off-gas in said TOD device, wherein during steady-state operation of said TOD device at least 90 percent of the fuel content supplied to said TOD device originates from said oxidizer off-gas or the reaction products of said oxidizer offgas, and is less than about 160 percent of minimum fuel content needed to operate the TOD without a cooling means.
2. The process according to claim 1 wherein said TOD is a regenerative thermal oxidizer.
3. The process according to claim 1 wherein during steady-state operation of said TOD device at least 70 percent of the fuel content supplied to said thermal oxidative destruction device originates from said oxidizer off-gas.
4. The process according to claim 1 wherein during steady state operation of said TOD device at least 90 mole percent of carbons present in said at least a portion of said oxidizer off-gas introduced into said TOD device is oxidized to carbon dioxide in said TOD.
5. The process according to claim 1 wherein said at least, a portion of said oxidizer off-gas oxidized in said TOD device comprises methyl acetate and/or methanol in an amount of at least 0.003 kilogram per kilogram of said aromatic compound fed to said oxidizer and less than 0.030 kilogram per kilogram of said aromatic compound fed to said oxidizer.
6. The process according to claim 1 wherein said at least a portion of said oxidizer off-gas oxidized in said TOD device comprises acetic acid in an amount of less than 0.005 kilogram per kilogram of said aromatic compound fed to said oxidizer.
7. The process according to claim 1 wherein said at least a portion of said oxidizer off-gas oxidized in said TOD device comprises carbon monoxide in an amount of less than 0.45 kilogram per kilogram of said aromatic compound fed to said oxidizer.
8. The process according to claim 1 wherein said at least a portion of said oxidizer off-gas oxidized in said TOD device comprises methyl acetate in an amount of at least 0.005 kilogram per kilogram of said aromatic compound fed to said oxidizer and less than 0.020 kilogram per kilogram of said aromatic compound fed to said oxidizer.
9. The process according to claim 5 wherein said methyl acetate present in said at least a portion of said oxidizer off-gas oxidized in said TOD device is a by-product of said oxidizing of step (a).
10. The process according to claim 5 wherein substantially no methyl acetate is being removed or converted or hydrolyzed after or during a solvent recovery step and before said TOD device so that substantially all of the methyl acetate exiting said solvent recovery step is fed to said TOD device.
11. The process according to claim 1 or 5 further comprising treating a TOD off-gas from said TOD device in a bromine scrubber to thereby produce a bromine-depleted off-gas.
12. The process according to claim 11 further comprising recovering hydrocarbyl compounds from said oxidizer off-gas in a solvent recovery system to thereby produce a hydrocarbyl-depleted off-gas.
13. The process according to claim 12 further comprising heating at least a portion of said hydrocarbyl-depleted off-gas with a thermal heating system to thereby provide a heated off-gas stream.
14. The process according to claim 13 further comprising passing at least a portion of said heated off-gas stream through at least one turboexpander to thereby generate work and produce a turboexpander off-gas.
15. The process according to claim 14 further comprising cooling said turboexpander off-gas in an off-gas condenser thereby condensing water vapor present in said turboexpander off-gas to thereby provide a condenser effluent comprising a condenser off-gas and a condensed liquid.
16. The process according to claim 15 further comprising passing at least a portion of said condenser effluent through a knock-out vessel to thereby separate said condenser effluent into a knock-out off-gas and a knock-out liquid.
17. The process according to claim 16 further comprising recompressing at least a portion of said knock-out off-gas in an off-gas compressor.
18. The process according to claim 16 or 17, further comprising subjecting at least a portion of said knock-out off-gas to thermal oxidative destruction (TOD) in a TOD device to thereby produce TOD off-gas.
19. The process according to claim 1 or 5 wherein said aromatic compound is para-xylene.
20. A process for making terephthalic acid, said process comprising:
(a) oxidizing para-xylene in at least one oxidizer to thereby produce an oxidizer off-gas and an oxidizer product comprising terephthalic acid, wherein the at least one oxidizer comprises a bubble column reactor;
(c) oxidizing said at least a portion of the oxidizer off-gas in said TOD device, wherein said at least a portion of said oxidizer off-gas oxidized in said TOD device comprises acetic acid in an amount of less than 0.005 kilogram per kilogram of said aromatic compound fed to said oxidizer and carbon monoxide in an amount of less than 0.45 kilogram per kilogram of said aromatic compound fed to said oxidizer,
wherein during steady-state operation of said TOD device at least 90 percent of the fuel content supplied to said TOD device originates from said oxidizer off-gas or the reaction products of said oxidizer offgas, and is less than about 160 percent of minimum fuel content needed to operate the TOD without a cooling means; and at least 90 mole percent of carbons present in said at least a portion of said oxidizer off-gas introduced into said TOD device is oxidized to carbon dioxide in said TOD.
21. The process according to claim 20 wherein said at least a portion of said oxidizer off-gas oxidized in said TOD device comprises methyl acetate and/or methanol in an amount of at least 0.003 kilogram per kilogram of said para-xylene fed to said oxidizer and less than 0.030 kilogram per kilogram of said para-xylene fed to said oxidizer.
22. The process according to claim 20 wherein said at least a portion of said oxidizer off-gas oxidized in said TOD device comprises methyl acetate in an amount of at least 0.005 kilogram per kilogram of said aromatic compound fed to said oxidizer and less than 0.020 kilogram per kilogram of said aromatic compound fed to said oxidizer.
23. The process according to claim 21 wherein said methyl acetate present in said at least a portion of said oxidizer off-gas oxidized in said TOD device is a by-product of said oxidizing of step (a).
24. The process according to claim 21 wherein substantially no methyl acetate is being removed or converted or hydrolyzed after or during a solvent recovery step and before said TOD device so that substantially all of the methyl acetate exiting said solvent recovery step is fed to said TOD device.
25. The process according to claim 20 further comprising treating a TOD off-gas from said TOD device in a bromine scrubber to thereby produce a bromine-depleted off-gas.
26. The process according to claim 25 further comprising recovering hydrocarbyl compounds from said oxidizer off-gas in a solvent recovery system to thereby produce a hydrocarbyl-depleted off-gas.
27. The process according to claim 26 further comprising heating at least a portion of said hydrocarbyl-depleted off-gas with a thermal heating system to thereby provide a heated off-gas stream.
28. The process according to claim 27 further comprising passing at least a portion of said heated off-gas stream through at least one turboexpander to thereby generate work and produce a turboexpander off-gas.
29. The process according to claim 28 further comprising cooling said turboexpander off-gas in an off-gas condenser thereby condensing water vapor present in said turboexpander off-gas to thereby provide a condenser effluent comprising a condenser off-gas and a condensed liquid.
30. The process according to claim 29 further comprising passing at least a portion of said condenser effluent through a knock-out vessel to thereby separate said condenser effluent into a knock-out off-gas and a knock-out liquid.
31. The process according to claim 30 further comprising recompressing at least a portion of said knock-out off-gas in an off-gas compressor.
US12/556,099 2008-10-31 2009-09-09 Dicarboxylic acid production with self-fuel oxidative destruction Active US9505692B2 (en)
CN2009801437997A CN102203045A (en) 2008-10-31 2009-10-22 Dicarboxylic acid production with self-fuel oxidative destruction
EP09744230.5A EP2344440B1 (en) 2008-10-31 2009-10-22 Dicarboxylic acid production with self-fuel oxidative destruction
ES09744230.5T ES2469799T3 (en) 2008-10-31 2009-10-22 Production dicarboxlico acid with oxidative destruction self-powered
MX2011004215A MX2011004215A (en) 2008-10-31 2009-10-22 Dicarboxylic acid production with self-fuel oxidative destruction.
PT97442305T PT2344440E (en) 2008-10-31 2009-10-22 Dicarboxylic acid production with self-fuel oxidative destruction
KR1020117012483A KR101744360B1 (en) 2008-10-31 2009-10-22 Dicarboxylic acid production with self-fuel oxidative destruction
CA2740833A CA2740833C (en) 2008-10-31 2009-10-22 Dicarboxylic acid production with self-fuel oxidative destruction
JP2011534495A JP2012507516A (en) 2008-10-31 2009-10-22 Production of dicarboxylic acids by a self-contained oxidative decomposition
RU2011121839/04A RU2575118C2 (en) 2008-10-31 2009-10-22 Obtaining dicarboxylic acid by method of self-activated oxidative destruction
MYPI2011001836A MY156674A (en) 2008-10-31 2009-10-22 Dicarboxylic acid production with self-fuel oxidative destruction
CN201710063201.XA CN106986759A (en) 2008-10-31 2009-10-22 Dicarboxylic acid production with self-fuel oxidative destruction
HK11112577.3A HK1158169A1 (en) 2008-10-31 2011-11-21 Dicarboxylic acid production with self-fuel oxidative destruction
JP2015075975A JP2015155428A (en) 2008-10-31 2015-04-02 Manufacturing dicarboxylic acid by self-feeding oxidative degradation
JP2018030394A JP2018109040A (en) 2008-10-31 2018-02-23 Production of dicarboxylic acid by self-feeding oxidative degradation
US20100113824A1 US20100113824A1 (en) 2010-05-06
US9505692B2 true US9505692B2 (en) 2016-11-29
ID=42132242
US12/556,099 Active US9505692B2 (en) 2008-10-31 2009-09-09 Dicarboxylic acid production with self-fuel oxidative destruction
US (1) US9505692B2 (en)
EP (1) EP2344440B1 (en)
JP (3) JP2012507516A (en)
KR (1) KR101744360B1 (en)
CN (2) CN106986759A (en)
CA (1) CA2740833C (en)
ES (1) ES2469799T3 (en)
HK (1) HK1158169A1 (en)
MX (1) MX2011004215A (en)
MY (1) MY156674A (en)
PT (1) PT2344440E (en)
WO (1) WO2010062313A1 (en)
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2009-09-09 US US12/556,099 patent/US9505692B2/en active Active
2009-10-22 PT PT97442305T patent/PT2344440E/en unknown
2009-10-22 MY MYPI2011001836A patent/MY156674A/en unknown
2009-10-22 MX MX2011004215A patent/MX2011004215A/en active IP Right Grant
2009-10-22 ES ES09744230.5T patent/ES2469799T3/en active Active
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2009-10-22 CN CN201710063201.XA patent/CN106986759A/en active Search and Examination
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Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:FOGLE III, RAYMOND ELBERT;SHEPPARD, RONALD BUFORD;UPSHAW, TIMOTHY ALAN;AND OTHERS;SIGNING DATES FROM 20090930 TO 20091104;REEL/FRAME:023479/0808