Patents by Inventor Derk T. A. Huibers
Derk T. A. Huibers has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 6414111Abstract: A method is set forth for separating a sterol or sterol ester from crude tall oil comprising fractionating the crude tall oil into a residue fraction and a volatile fraction, wherein the temperature of the residue fraction does not exceed about 290° C., and wherein the residue fraction includes the sterol or sterol ester. By application of this method, which can be implemented in existing fractionating equipment or in specially designed pitch collecting apparatuses disclosed herein, the yield of sterols can exceed 50% with respect to the sterols present in crude tall oil. A method is also provided for separating unsaponifiable material from a tall oil stream comprising saponifying the stream with a mixture of sodium hydroxide and potassium hydroxide to form sodium and potassium salts of fatty acids, rosin acids, or both; evaporating the unsaponifiable material; and acidulating the unevaporated sodium and potassium salts.Type: GrantFiled: February 14, 2001Date of Patent: July 2, 2002Assignee: Arizona Chemical CompanyInventors: Derk T. A. Huibers, Andrew M. Robbins, David H. Sullivan
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Publication number: 20010007906Abstract: A method is set forth for separating a sterol or sterol ester from crude tall oil comprising fractionating the crude tall oil into a residue fraction and a volatile fraction, wherein the temperature of the residue fraction does not exceed about 290° C., and wherein the residue fraction includes the sterol or sterol ester. By application of this method, which can be implemented in existing fractionating equipment or in specially designed pitch collecting apparatuses disclosed herein, the yield of sterols can exceed 50% with respect to the sterols present in crude tall oil. A method is also provided for separating unsaponifiable material from a tall oil stream comprising saponifying the stream with a mixture of sodium hydroxide and potassium hydroxide to form sodium and potassium salts of fatty acids, rosin acids, or both; evaporating the unsaponifiable material; and acidulating the unevaporated sodium and potassium salts.Type: ApplicationFiled: February 14, 2001Publication date: July 12, 2001Applicant: Arizona Chemical CorporationInventors: Derk T. A. Huibers, Andrew M. Robbins, David H. Sullivan
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Patent number: 6107456Abstract: A method is set forth for separating a sterol or sterol ester from crude tall oil comprising fractionating the crude tall oil into a residue fraction and a volatile fraction, wherein the temperature of the residue fraction does not exceed about 290.degree. C., and wherein the residue fraction includes the sterol or sterol ester. By application of this method, which can be implemented in existing fractionating equipment or in specially designed pitch collecting apparatuses disclosed herein, the yield of sterols can exceed 50% with respect to the sterols present in crude tall oil. A method is also provided for separating unsaponifiable material from a tall oil stream comprising saponifying the stream with a mixture of sodium hydroxide and potassium hydroxide to form sodium and potassium salts of fatty acid, rosin acids, or both; evaporating the unsaponifiable material; and acidulating the unevaporated sodium and potassium salts.Type: GrantFiled: September 15, 1998Date of Patent: August 22, 2000Assignee: Arizona Chemical CorporationInventors: Derk T. A. Huibers, Andrew M. Robbins, David H. Sullivan
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Patent number: 5286845Abstract: The present invention relates to the conversion of tall oil soap to produce crude tall oil. An aqueous tall oil soap solution generated in a kraft wood-pulping process is placed in contact with carbon dioxide, under pressure, to form crude tall oil and sodium bicarbonate brine. The crude tall oil and sodium bicarbonate brine are then allowed to separate, under pressure, into a crude tall oil layer and a sodium bicarbonate brine layer. The crude tall oil layer is then separated from the sodium bicarbonate brine layer, again under pressure. The separated crude tall oil may then be further refined to yield fatty acids, resin acids, and other constituents, which are useful in numerous industrial applications, such as in soaps, lubricants, inks, adhesives, and coatings.Type: GrantFiled: May 20, 1992Date of Patent: February 15, 1994Assignee: Union Camp CorporationInventors: Derk T. A. Huibers, James W. Gillis, Andrew Robbins
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Patent number: 5283319Abstract: The present invention provides for the efficient recycling of carbon dioxide used in high pressure tall oil soap acidulation processes. The excess carbon dioxide used in the high pressure tall oil soap acidulation processes is recycled and contacted with an aqueous tall oil soap solution at a point before the high pressure contacting stage. Preferably, the recycled carbon dioxide is contacted in a first reactor, under pressure, to provide a preliminary tall oil mixture having an extent of acidification beyond the presence of a gel phase. Methods are provided for the monitoring of the acidulation reaction in the first reactor to maintain the extent of acidification beyond the gel phase region.Type: GrantFiled: June 23, 1993Date of Patent: February 1, 1994Assignee: Union Camp CorporationInventors: Derk T. A. Huibers, Richard G. Grotyohann, Andrew M. Robbins
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Patent number: 5164480Abstract: The present invention relates to the direct electrolysis of tall oil soap (TOS) to produce crude tall oil (CTO). An aqueous tall oil soap solution generated in a kraft wood-pulping process is placed in contact with an anode in an electrolytic cell, wherein the tall oil soap is dissassociated to form crude tall oil and free sodium ions. The sodium ions migrate through a membrane to associate with hydroxide ions formed in a cathode chamber to form NaOH, which may optionally be recycled to the kraft pulping process as a make-up chemical for lost sodium. The crude tall oil is recovered from the electrolyzed tall oil soap solution for further refinement. Optionally, the tall oil soap solution is treated prior to electrolysis to remove components which may interfere with the electrolysis.Type: GrantFiled: August 20, 1991Date of Patent: November 17, 1992Assignee: Union Camp CorporationInventors: Derk T. A. Huibers, Roger W. Daniels, Marilyn J. Niksa, Richard J. Coin, Joseph Elliott
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Patent number: 4446070Abstract: A process for the catalytic oxidation of polynuclear aromatic hydrocarbons in general and anthracene in particular in an oxygen-containing gas in the presence of a ceric ammonium nitrate catalyst system wherein turnover ratios are increased by: (1) use of acetic acid as solvent; (2) use of pure molecular oxygen as the oxygen-containing gas; (3) use of ammonium vanadate as a promoter; and (4) addition of acetic anhydride to react with water produced as a by-product of the oxidation reaction. By use of the filtrate, remaining after removal of anthraquinone by filtration, to catalyze the oxidation of fresh anthracene, and by addition of nitric acid to restore catalytic activity after a series of oxidation reactions, anthraquinone is produced from anthracene in a continuous system.Type: GrantFiled: June 10, 1981Date of Patent: May 1, 1984Assignee: HRI, Inc.Inventors: Derk T. A. Huibers, Cheng-Yih Jenq
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Patent number: 4437973Abstract: A process for hydrogenation of coal to produce hydrocarbon liquids and gases, wherein the yield of liquid products is increased by feeding particulate coal at temperature below about 600.degree. F. directly into a back-mixed reactor and preferably into an ebullated bed catalytic reaction zone containing coal-derived liquid and hydrogen for rapid heating and conversion. In the process, the coal is pressurized and fed without preheating directly into the reaction zone and additional heat needed in the reaction zone to maintain temperature therein at 750.degree.-900.degree. F. is provided by heating recycle hydrogen and coal-derived liquid streams to temperatures above the desired reaction zone temperature.Type: GrantFiled: April 5, 1982Date of Patent: March 20, 1984Assignee: HRI, Inc.Inventors: Derk T. A. Huibers, Paul H. Kydd
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Patent number: 4433184Abstract: Monosaccharides, such as glucose-water solution, are catalytically hydrogenated by being passed through multiple reaction zones connected in series and each containing a high-activity supported nickel catalyst to produce 99.8 W % overall conversion to an alditol solution such as sorbitol. The pH of liquid in each reaction zone is controlled to between 4.5 and 7 by adding an alkali solution such as sodium hydroxide to the feed to prevent acid leaching of catalyst metal and to help maintain catalyst activity therein. Reaction zone conditions used are 130.degree.-180.degree. C. temperature, 500-2000 psig hydrogen partial pressure, and a ratio of hydrogen gas/feed liquid within the range of about 500-5000. Feedstream liquid space velocity is maintained within range of 0.5-16 V.sub.f /Hr/V.sub.c, with higher space velocities being used for achieving lower incremental conversion desired in the subsequent reaction zones to help maintain pH of the effluent liquid within the desired range.Type: GrantFiled: April 27, 1981Date of Patent: February 21, 1984Assignee: HRI, Inc.Inventors: Derk T. A. Huibers, James C. Chao, Rajni C. Shah
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Patent number: 4431850Abstract: A process for thermal dealkylation of alkylated phenols feedstocks, which comprises reacting a feed mixture containing mono and poly-alkylated phenols and gaseous hydrogen at temperature ranging from about 900.degree. to about 1100.degree. F. at hydrogen partial pressure of 300 to 1600 psig, and space velocity of 0.2 to 3.0 volume feed/hr/volume of reactor to produce a phenol-containing product at increased selectivity and yield of phenol. For feedstream mixtures containing more than about 10 W % phenols, a prior distillation step is preferably used to remove the excessive phenol as product and thus avoid undesired dehydroxylation reactions in the hydrodealkylation step to which the feed phenol concentration is usually about 2-8 W %.Type: GrantFiled: November 9, 1981Date of Patent: February 14, 1984Assignee: HRI, Inc.Inventors: Derk T. A. Huibers, Cheng-Yih Jenq
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Patent number: 4424109Abstract: An improved catalyst for a coal liquefaction process; e.g., the H-Coal Process, for converting coal into liquid fuels, and where the conversion is carried out in an ebullated-catalyst-bed reactor wherein the coal contacts catalyst particles and is converted, in addition to liquid fuels, to gas and residual oil which includes preasphaltenes and asphaltenes. The improvement comprises a catalyst selected from the group consisting of the oxides of nickel molybdenum, cobalt molybdenum, cobalt tungsten, and nickel tungsten on a carrier of alumina, silica, or a combination of alumina and silica. The catalyst has a total pore volume of about 0.500 to about 0.900 cc/g and the pore volume comprises micropores, intermediate pores and macropores, the surface of the intermediate pores being sufficiently large to convert the preasphaltenes to asphaltenes and lighter molecules. The conversion of the asphaltenes takes place on the surface of micropores.Type: GrantFiled: April 7, 1981Date of Patent: January 3, 1984Assignee: Hydrocarbon Research, Inc.Inventors: Derk T. A. Huibers, Chia-Chen C. Kang
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Patent number: 4421568Abstract: A method for producing L-sugars including L-idose and L-gulose as well as D-fructose from D-glucose. The method comprises epimerizing D-glucose to a mixture of D-glucose and D-mannose, hydrogenating the mixture in a fixed catalyst bed to provide D-sorbitol and D-mannitol, separating the D-mannitol by fractional crystallization, oxydizing separately the D-sorbitol and D-mannitol to provide L-sorbose and D-fructose, respectively; and racemizing the L-sorbose in a weak alkaline solution to provide a mixture of L-sorbose, L-idose and L-gulose, and precipitating the remaining L-sorbose with a dilute lime solution. The unconverted L-sorbose is recovered and recycled.Type: GrantFiled: August 26, 1981Date of Patent: December 20, 1983Assignee: Hydrocarbon Research, Inc.Inventor: Derk T. A. Huibers
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Patent number: 4420644Abstract: A lignin-containing feed material in particulate form is mixed with a process-derived slurrying oil and fed into an ebullated catalyst bed hydrocracking reactor. Reaction conditions are maintained at 650.degree.-850.degree. F. temperature, 500-2500 psig hydrogen partial pressure and space velocity of 1.0-10 wt. lignin/hr./wt. catalyst. The reaction products are phase separated to recover hydrogen and slurrying oil, and the resulting liquid stream is passed to a thermal hydrodealkylation step. The reacted stream is fractionated to produce phenol and benzene products, along with a heavy alkylated material which is recycled to the hydrodealkylation step to increase the yield of phenol and benzene.Type: GrantFiled: August 24, 1981Date of Patent: December 13, 1983Assignee: Hydrocarbon Research, Inc.Inventors: Derk T. A. Huibers, Hugh J. Parkhurst, Jr.
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Patent number: 4409416Abstract: A process for cracking lignin-containing feed materials, such as precipitated from black liquor, to produce hydrocarbon products such as ethylene, utilizing dual fluidized beds of particulate solids in series flow arrangement. In the process, the feedstock is introduced with a diluent gas such as steam into the first or fast fluidized bed for cracking reactions at superficial gas velocity exceeding about 5 ft/sec. A particulate solids carrier material, which can comprise at least partly coke produced in the process, is circulated between the beds, and coke deposited on the carrier in the first or cracking bed at 1000.degree.-1600.degree. F. temperature is burned off in a second or combustion bed maintained at 1400.degree.-2000.degree. F. temperature by an oxygen-containing gas and diluent steam introduced therein. Superficial upward gas velocity in the fast fluidized bed zone exceeds about 5 ft/sec. and the bed density exceeds about 3 lb/cu.ft.Type: GrantFiled: March 1, 1982Date of Patent: October 11, 1983Inventors: George J. Snell, Derk T. A. Huibers
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Patent number: 4404084Abstract: An improved process for hydrogenation of coal containing ash with agglomeration and removal of ash from an ebullated bed catalytic reactor to produce deashed hydrocarbon liquid and gas products. In the process, a flowable coal-oil slurry is reacted with hydrogen in an ebullated catalyst bed reaction zone at elevated temperature and pressure conditions. The upward velocity and viscosity of the reactor liquid are controlled so that a substantial portion of the ash released from the coal is agglomerated to form larger particles in the upper portion of the reactor above the catalyst bed, from which the agglomerated ash is separately withdrawn along with adhering reaction zone liquid. The resulting hydrogenated hydrocarbon effluent material product is phase separated to remove vapor fractions, after which any ash remaining in the liquid fraction can be removed to produce substantially ash-free coal-derived liquid products.Type: GrantFiled: March 11, 1982Date of Patent: September 13, 1983Assignee: Hri, Inc.Inventors: Derk T. A. Huibers, Edwin S. Johanson
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Patent number: 4371616Abstract: A method for producing L-sugars including L-idose and L-gulose from D-glucose. The method comprises hydrogenating D-glucose to provide sorbitol, oxydizing the D-sorbitol to provide L-sorbose, racemizing the L-sorbose to provide a mixture of L-sorbose, L-idose and L-gulose, and precipitating the L-sorbose with lime from a dilute solution. The unconverted L-sorbose is recovered by carbonation and recycled. The hydrogenation of glucose is done in a fixed catalyst bed.Type: GrantFiled: August 26, 1981Date of Patent: February 1, 1983Assignee: Hydrocarbon Research, Inc.Inventor: Derk T. A. Huibers
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Patent number: 4366332Abstract: Alditols such as 15-40 W. % sorbitol solution in water are catalytically hydrocracked in a fixed bed reaction process using a high activity nickel catalyst to produce at least about 30 W. % conversion to glycerol and glycol products. The feedstream pH is controlled to prevent catalyst damage by adding a basic promotor material such as calcium hydroxide. Reaction zone conditions are maintained at 420.degree.-520.degree. F. temperature, 1200-2000 psig hydrogen partial pressure, and liquid hourly space velocity of 1.5 to 3.0. To maintain desired activity and glycerol yield, the catalyst is regenerated to provide catalyst age of 8-200 hours. The reaction products are separated in a recovery step, and any alditols can be recycled to the reaction zone for further hydrogenolysis to produce 40-90 W. % glycerol product. Sorbitol conversion is maintained preferably at between about 30-70 W.Type: GrantFiled: January 21, 1981Date of Patent: December 28, 1982Assignee: Hydrocarbon Research, Inc.Inventors: James C. Chao, Derk T. A. Huibers
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Patent number: 4322569Abstract: Monosaccharides such as glucose solution are catalytically hydrogenated in fixed bed reaction process using a high activity nickel catalyst to produce at least about 98 W % conversion to sorbitol solution. The feedstream pH is controlled to between 7 and 13 by adding a basic solution such as sodium hydroxide. Reaction zone conditions are 500-2000 psig hydrogen partial pressure, 130.degree.-180.degree. C. temperature, and use a ratio of hydrogen gas/feed liquid within the range of 1000-5000. Feedstream liquid space velocity is within range of 0.5-3.5 Vf/Hr/Vc.Type: GrantFiled: August 1, 1980Date of Patent: March 30, 1982Assignee: Hydrocarbon Research, Inc.Inventors: James C. Chao, Derk T. A. Huibers
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Patent number: 4145918Abstract: A freeze and thaw indicator is provided utilizing the expansion characteristics of water when it undergoes a change from the liquid state to the solid state. An ampul having one side made weaker than its opposite side is substantially filled with water. Indicator paper having ink printed on one side is situated adjacent to the ampul. The indicator paper and ampul are housed in a blister pack plastic container for protecting the ampul from breakage. When the temperature around the indicator reaches the freezing point of water, the ampul breaks. During a subsequent thawing, the water flows on to the indicator paper causing the ink which is printed on one side to wick up, thereby indicating that the freeze or thaw has taken place.Type: GrantFiled: September 7, 1976Date of Patent: March 27, 1979Assignee: Akzona IncorporatedInventors: Thomas W. Couch, Erick-Pierre Fournier, James A. Harvey, Derk T. A. Huibers, Howard A. Mercer