Jon Jay Harper

US Patent:

43115217, Jan 19, 1982

Filed:

Oct 1, 1980

Appl. No.:

6/192913

Inventors:

Jon J. Harper - Naperville IL
Stephen J. Pietsch - Oak Park IL

Assignee:

Standard Oil Company (Indiana) - Chicago IL

International Classification:

C22B 300

US Classification:

75101BE

Abstract:

Precipitation-free recovery of catalyst metal content of residue from manufacture of trimellitic acid by oxidation with source of molecular oxygen of liquid pseudocumene in presence of cobalt and manganese, cobalt, manganese and cerium, followed by removal of trimellitic acid or its anhydride and, if used, reaction solvent and then separating manganese from the recovered metals. The foregoing is accomplished by extraction of such residue with water, contacting the resulting aqueous extract solution or suspension of insolubles in the aqueous solution with one side of a cation permeable fluoropolymer membrane whose other side is in contact with a hydrohalidic acid to permit metal ions to pass through the membrane, removing the hydrohalidic solution of the catalyst metals, and then after a pH adjustment adding metallic manganese to precipitate cobalt as metal.

US Patent:

42985803, Nov 3, 1981

Filed:

Dec 19, 1980

Appl. No.:

6/218061

Inventors:

Jon J. Harper - Naperville IL
Stephen J. Pietsch - Oak Park IL

Assignee:

Standard Oil Company (Indiana) - Chicago IL

International Classification:

C01G 4506
C01G 5108

US Classification:

423 40

Abstract:

Recovery of cobalt and manganese from residue of trimellitic acid manufacture and recovery as 4-carboxy-phthalic anhydride by extracting the residue with an aqueous alkaline solution containing carbonate ions which leaves a precipitate of metal carbonates, dissolving said precipitate as the metal chlorides, and at an upwardly adjusted pH adding powdered manganese to precipitate metallic cobalt and separating it by magnetic means.

US Patent:

51839334, Feb 2, 1993

Filed:

Oct 15, 1991

Appl. No.:

7/776812

Inventors:

Jon J. Harper - Naperville IL
George E. Kuhlmann - Naperville IL
Keith D. Larson - Chicago IL
Rosemary F. McMahon - Wheaton IL
Paul A. Sanchez - Lisle IL

Assignee:

Amoco Corporation - Chicago IL

International Classification:

C07C 51265

US Classification:

562414

Abstract:

Provided is a continuous process for producing 2,6-naphthalenedicarboxylic acid by the liquid phase oxidation of 2,6-dimethylnaphthalene comprising continuously adding to a reaction zone the oxidation reaction components comprising 2,6-dimethylnaphthalene, a source of molecular oxygen, a solvent comprising an aliphatic monocarboxylic acid, and a catalyst comprising cobalt, manganese and bromine components, wherein the atom ratio of manganese to cobalt is about 5:1 to about 0. 3:1, the total of cobalt and manganese is at least about 0. 40 weight percent based on the weight of solvent, and maintaining the contents of the reaction zone at a temperature of about 370. degree. F. to about 420. degree. F. and at a pressure sufficient to maintain at least a portion of the monocarboxylic acid in the liquid phase thereby oxidizing the 2,6-dimethylnaphthalene to 2,6-naphthalenedicarboxylic acid. By operating according to the process of this invention, 2,6-naphthalenedicarboxylic acid can be continuously produced in high yield and with low levels of impurities.

US Patent:

43384641, Jul 6, 1982

Filed:

Dec 17, 1979

Appl. No.:

6/104088

Inventors:

Jon J. Harper - Naperville IL
Martin A. Zeitlin - Naperville IL

Assignee:

Standard Oil Company (Indiana) - Chicago IL

International Classification:

C07C 5143

US Classification:

562608

Abstract:

Acetic acid can be prepared in high conversions and selectively by the oxidation of liquid n-butane at temperatures of from 120. degree. C. up to 230. degree. C. in the presence of an acetic acid solution containing bromine ions in combination with ions of cobalt or cobalt and manganese. The debutanized effluent of such oxidation consists mainly of acetic acid and water but also contains esters and ketones boiling lower than acetic acid, some higher carbon content aliphatic acids and metal salts boiling higher than acetic acid and rather small amounts of 3-bromo-2-butanone which, although boiling higher than acetic acid, cannot be separated by simple distillation as can be the other non-acetic acid organic impurities. The present inventive technique for removal of said bromo-ketone has for its concept the use of a combination of cryogenic crystallization and removal of adhering mother liquor which can be practiced continuously in known apparatus devised for other fractional crystallizations.

US Patent:

43093906, Jan 5, 1982

Filed:

Dec 19, 1980

Appl. No.:

6/218060

Inventors:

Jon J. Harper - Naperville IL
Stephen J. Pietsch - Oak Park IL

Assignee:

Standard Oil Company (Indiana) - Chicago IL

International Classification:

C01G 5108
C01G 4500

US Classification:

423150

Abstract:

Recovery of cobalt and manganese metal oxidation catalysts from residue of trimellitic acid manufacture and separation of recovered cobalt from recovered manganese can be accomplished by a novel method involving dissolving the residue in water, displacing dissolved cobalt as cobalt metal by manganese metal added to the solution whose pH has been adjusted to pH of 6 and then using magnetic means for separating metallic cobalt from the cobalt-free solution.

US Patent:

42785030, Jul 14, 1981

Filed:

Dec 26, 1979

Appl. No.:

6/106669

Inventors:

Martin A. Zeitlin - Naperville IL
Jon J. Harper - Naperville IL

Assignee:

Standard Oil Company (Indiana) - Chicago IL

International Classification:

B01D 314
C07C 5144
C07C 5116

US Classification:

203 28

Abstract:

Excessive energy consumption of a combination of multi-fractionations and multi-distillations of concentrating aqueous acetic acid product of liquid phase oxidations, especially oxidation of liquid n-butane with oxygen gas while the butane is dissolved in liquid acetic acid containing a catalyst system comprising Co-Br or Co-Mn-Br, is avoided and an otherwise hard to remove bromo-ketone is readily removed by a combination of sequential steps of decompressing the oxidation reaction mixture to remove unreacted butane as well as gaseous products, heat treating the decompressed liquid at a temperature of from 150. degree. C. up to 200. degree. C. for from 15 up to 150 minutes, subjecting the heat treated liquid to fractionation while recycling to the rectification zone thereof an aqueous portion of low boiling impurities as a means for concentrating the acetic acid and thereafter further concentrating the acetic acid produced by continuous fractional crystallization.

US Patent:

40325636, Jun 28, 1977

Filed:

Sep 2, 1975

Appl. No.:

5/609193

Inventors:

Jon J. Harper - Naperville IL
Antonio E. Navarrete - Downers Grove IL
Richard J. Thomas - Huntington Beach CA

Assignee:

Standard Oil Company - Chicago IL

International Classification:

C07C 6980
C07C 6982

US Classification:

260475R

Abstract:

A process is disclosed for producing the dimethyl esters of aromatic dicarboxylic acids wherein the acid is esterified with a low molecular weight alcohol, the product is crystallized and separated to isolate a mass of the diester crystals and recover a mother liquor. An improvement in such process resides in the thermal oxidation with molecular oxygen of a mother liquor material to produce a mono methylphthalate from either p-methyl toluate or methyl-4-carboxybenzaldehyde. A portion of the oxidized mother liquor is recycled to the esterification zone wherein the mono methylphthalate can be esterified to the dimethyl ester while another portion of the oxidized mother liquor stream is passed to an evaporation treatment zone, preferably a wiped film evaporator, wherein overhead material is separated from a high boiling bottoms material and recycled to the esterification reaction zone. The high boiling bottoms stream from the evaporation treatment zone is purged from the system thereby removing from the overall process high boiling organics including ash.

US Patent:

43127142, Jan 26, 1982

Filed:

Dec 17, 1979

Appl. No.:

6/104089

Inventors:

Jon J. Harper - Naperville IL

Assignee:

Standard Oil Company (Indiana) - Chicago IL

International Classification:

C07C 5121
C07C 5144

US Classification:

203 28

Abstract:

The oxidation of liquid n-butane with oxygen gas at a temperature of from 120. degree. C. up to 235. degree. C. in the presence of an acetic acid solution containing bromide ion in combination with ions of cobalt or cobalt and manganese produces a reaction effluent containing mainly acetic acid (65 to 72 weight percent) and water (23 to 27 weight percent) together with impurity concentrations of esters and ketones boiling lower than acetic acid, higher carbon (C. sub. 3 and C. sub. 4) aliphatic monocarboxylic acids boiling higher than acetic acid and the difficultly separable 3-bromo-2-butanone impurity. The concentration of said bromoketone can be decreased by maintaining said reaction effluent or its debutanized residue at a temperature of from 150. degree. C. up to 200. degree. C. for 15 to 150 minutes.