WO1997049485B1 - Methods and devices for oxidizing a hydrocarbon to form an acid - Google Patents
Methods and devices for oxidizing a hydrocarbon to form an acidInfo
- Publication number
- WO1997049485B1 WO1997049485B1 PCT/US1997/010830 US9710830W WO9749485B1 WO 1997049485 B1 WO1997049485 B1 WO 1997049485B1 US 9710830 W US9710830 W US 9710830W WO 9749485 B1 WO9749485 B1 WO 9749485B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- hydrocarbon
- catalyst
- methods
- water
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 6
- 239000004215 Carbon black (E152) Substances 0.000 title abstract 5
- 150000002430 hydrocarbons Chemical class 0.000 title abstract 5
- 230000001590 oxidative Effects 0.000 title abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract 8
- 238000006243 chemical reaction Methods 0.000 claims abstract 5
- 239000007791 liquid phase Substances 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 3
- 239000012071 phase Substances 0.000 claims abstract 3
- 239000007788 liquid Substances 0.000 claims abstract 2
- 238000001556 precipitation Methods 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 238000005755 formation reaction Methods 0.000 claims 2
- 238000000889 atomisation Methods 0.000 claims 1
- 238000010587 phase diagram Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical group O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
Abstract
Methods and devices for controlling the reaction of a hydrocarbon to an acid by making phase-related adjustments are disclosed. In order to improve reaction rate and reactivity of the oxidation, a single phase at the operating temperature is attained and maintained by adjusting one or more of gaseous oxidant flow rate, pressure in the reaction zone, temperature in the reaction zone, feed rate of hydrocarbon, feed rate of solvent, feed rate of water if water is being fed, feed rate of the catalyst and other parameters. Methods and devices are also disclosed, wherein a hydrocarbon is reacted at a steady state with a gaseous oxidant to form an acid in a liquid mixture. The amount of water is maintained between a maximum level of water, over which maximum level the substantially single liquid phase is transformed to two liquid phases, and a minimum level under which catalyst precipitates. Further, methods are disclosed, wherein the temperature of the mixture is lowered to a point at which solid dibasic acid is precipitated, while maintaining a single liquid phase, and optionally all the catalyst in solution. At least part of the formed acid is then removed. The preferred hydrocarbon is cyclohexane, the preferred acid is adipic acid, the preferred solvent is acetic acid, and the preferred catalyst is cobalt (II) acetate tetrahydrate.
Claims
[received by the International Bureau on 23 December 1997 (23.12.97); new claim 50 added; remaining claims unchanged (I page)]
48. A reactor device as defined in claim 26, 27, 28, 29, 30, 31 , 32. 33, 34. 35. 36, 37. 38. 39, 40, 41 , 42, 43, 44. 45, 46, or 47, comprising an atomization chamber.
49. A reactor device as defined in claim 26, 27, 28, 29, 30, 31 , 32. 33, 34. 35. 36, 37, 38, 39, 40, 41 , 42, 43, 44, 45. 46, or 47. comprising a stirred-tank reactor.
50. A method as defined in claim 1, 2, 3. or 4, further comprising a step of comparing compositional data of the liquid mixture with one or more of phase diagrams, thermodynamic data bases, flow sheets, computer flow sheet simulations, catalyst precipitation data, energy balances, and experimental data, and a step of making phase related adjustments and/or catalyst precipitation adjustments in order to avoid formation of a second liquid phase, and/or catalyst precipitation, respectively, in the first reaction zone, if the comparison indicates that formation of a second liquid phase and/or catalyst precipitation are being approached.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97930185A EP0910466A1 (en) | 1996-06-24 | 1997-06-23 | Methods and devices for oxidizing a hydrocarbon to form an acid |
| BR9710856A BR9710856A (en) | 1996-06-24 | 1997-06-23 | Method and devices for oxidizing a hydrocarbon to form an acid |
| JP50341998A JP2002515041A (en) | 1996-06-24 | 1997-06-23 | Methods and devices for oxidizing hydrocarbons to form acids |
| AU34076/97A AU3407697A (en) | 1996-06-24 | 1997-06-23 | Methods and devices for oxidizing a hydrocarbon to form an acid |
| US08/989,910 US6359173B1 (en) | 1996-06-24 | 1997-12-12 | Methods and devices for oxidizing a hydrocarbon to form an acid |
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2079896P | 1996-06-24 | 1996-06-24 | |
| US08/812,847 US6288270B1 (en) | 1996-06-24 | 1997-03-06 | Methods for controlling the reaction rate of a hydrocarbon to an acid by making phase-related adjustments |
| US08/824,992 US5922908A (en) | 1996-06-24 | 1997-03-27 | Methods for preparing dibasic acids |
| US08/876,692 | 1997-06-16 | ||
| US08/812,847 | 1997-06-16 | ||
| US08/876,692 US6337051B1 (en) | 1996-06-24 | 1997-06-16 | Device for detecting formation of a second liquid phase |
| US60/020,798 | 1997-06-16 | ||
| US08/824,992 | 1997-06-16 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/876,692 Continuation-In-Part US6337051B1 (en) | 1996-06-24 | 1997-06-16 | Device for detecting formation of a second liquid phase |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/989,910 Continuation-In-Part US6359173B1 (en) | 1996-06-24 | 1997-12-12 | Methods and devices for oxidizing a hydrocarbon to form an acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1997049485A1 WO1997049485A1 (en) | 1997-12-31 |
| WO1997049485B1 true WO1997049485B1 (en) | 1998-02-19 |
Family
ID=27486952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/010830 WO1997049485A1 (en) | 1996-06-24 | 1997-06-23 | Methods and devices for oxidizing a hydrocarbon to form an acid |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6337051B1 (en) |
| EP (1) | EP0910466A1 (en) |
| JP (1) | JP2002515041A (en) |
| KR (1) | KR20000022519A (en) |
| CN (1) | CN1226185A (en) |
| AU (1) | AU3407697A (en) |
| BR (1) | BR9710856A (en) |
| CA (1) | CA2258015A1 (en) |
| WO (1) | WO1997049485A1 (en) |
Families Citing this family (8)
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| US6143927A (en) | 1996-06-24 | 2000-11-07 | Rpc Inc. | Methods for removing catalyst after oxidation of hydrocarbons |
| US6037491A (en) * | 1997-07-25 | 2000-03-14 | Rpc Inc. | Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio |
| CN1270577A (en) * | 1997-09-16 | 2000-10-18 | Rpc公司 | Methods and reactor devices for removing catalyst after oxidation of hydrocarbons |
| EP1054856A1 (en) | 1998-02-09 | 2000-11-29 | RPC Inc. | Process for treating cobalt catalyst in oxidation mixtures of hydrocarbons to dibasic acids |
| BR9907998A (en) * | 1998-02-19 | 2000-10-24 | Rpc Inc | Processes and devices for catalyst separation from oxidation mixtures |
| US9038451B2 (en) * | 2010-07-08 | 2015-05-26 | Baker Hughes Incorporated | Optical method for determining fouling of crude and heavy fuels |
| WO2013066418A1 (en) | 2011-06-14 | 2013-05-10 | Corning Incorporated | Hybrid microfluidic assemblies |
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-
1997
- 1997-06-16 US US08/876,692 patent/US6337051B1/en not_active Expired - Fee Related
- 1997-06-23 KR KR1019980710964A patent/KR20000022519A/en not_active Application Discontinuation
- 1997-06-23 CA CA002258015A patent/CA2258015A1/en not_active Abandoned
- 1997-06-23 JP JP50341998A patent/JP2002515041A/en active Pending
- 1997-06-23 CN CN97196696A patent/CN1226185A/en active Pending
- 1997-06-23 BR BR9710856A patent/BR9710856A/en not_active IP Right Cessation
- 1997-06-23 WO PCT/US1997/010830 patent/WO1997049485A1/en not_active Application Discontinuation
- 1997-06-23 EP EP97930185A patent/EP0910466A1/en not_active Withdrawn
- 1997-06-23 AU AU34076/97A patent/AU3407697A/en not_active Abandoned
- 1997-12-12 US US08/989,910 patent/US6359173B1/en not_active Expired - Fee Related
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