US20120041240A1 - Method for obtaining solid paraffinic compounds by hydrotreatment of vegetable oils - Google Patents

Method for obtaining solid paraffinic compounds by hydrotreatment of vegetable oils Download PDF

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Publication number
US20120041240A1
US20120041240A1 US13/142,101 US200913142101A US2012041240A1 US 20120041240 A1 US20120041240 A1 US 20120041240A1 US 200913142101 A US200913142101 A US 200913142101A US 2012041240 A1 US2012041240 A1 US 2012041240A1
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Prior art keywords
oil
paraffins
oils
obtaining
solid
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US13/142,101
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Inventor
Manuel Laureano Nuñez Isaza
Laura Patricia Prada Villamizar
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Ecopetrol SA
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Ecopetrol SA
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Assigned to ECOPETROL S.A. reassignment ECOPETROL S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NUNEZ ISAZA, MANUEL LAUREANO, PRADA VILLA MIZAR, LAURA PATRICIA
Publication of US20120041240A1 publication Critical patent/US20120041240A1/en
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/54Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids characterised by the catalytic bed
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C08L91/06Waxes
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42Catalytic treatment
    • C10G3/44Catalytic treatment characterised by the catalyst used
    • C10G3/45Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof
    • C10G3/46Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof in combination with chromium, molybdenum, tungsten metals or compounds thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/50Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids in the presence of hydrogen, hydrogen donors or hydrogen generating compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L7/00Fuels produced by solidifying fluid fuels
    • C10L7/02Fuels produced by solidifying fluid fuels liquid fuels
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85Chromium, molybdenum or tungsten
    • B01J23/88Molybdenum
    • B01J23/883Molybdenum and nickel
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/20Sulfiding
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10Feedstock materials
    • C10G2300/1011Biomass
    • C10G2300/1014Biomass of vegetal origin
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10Feedstock materials
    • C10G2300/1011Biomass
    • C10G2300/1018Biomass of animal origin
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40Characteristics of the process deviating from typical ways of processing
    • C10G2300/4006Temperature
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40Characteristics of the process deviating from typical ways of processing
    • C10G2300/4012Pressure
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40Characteristics of the process deviating from typical ways of processing
    • C10G2300/4018Spatial velocity, e.g. LHSV, WHSV
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/70Catalyst aspects
    • C10G2300/701Use of spent catalysts
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/10Process efficiency
    • Y02P20/129Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00Technologies relating to oil refining and petrochemical industry
    • Y02P30/20Technologies relating to oil refining and petrochemical industry using bio-feedstock

Definitions

  • the solid paraffins derived from petroleum present a high content of carcinogenic pollutants, that doesn't allow them to be suitable for applications in the pharmaceutical or food industry, particularly by the presence of polynuclear aromatic hydrocarbons (PNA's).
  • PNA's polynuclear aromatic hydrocarbons
  • vegetable oils are hydro-processed to produce hydrocarbons, mainly C 15 to C 18 paraffins in the boiling range of diesel with a better cetane.
  • This hydroprocess includes a hydro-cracking of the triglyceride structure, a hydrotreatment with the removal of oxygen and a hydrogenation with the saturation of the double bonds.
  • the operation conditions of this process, for the crude palm oil, are: 350 to 450° C. of temperature, 4.8 to 15.2 MPa of pressure and an hourly space velocity between 0.5 to 5 h ⁇ 1 .
  • the obtained diesel contains C 14 to C 18 paraffins with less than 5 ppm of sulphur, with a iso-paraffin/normal paraffin ratio of 2 to 8, with less than 0.6% in weight of oxygenated compounds, with less than 0.4% in weight of fatty acids, with less than 10% in weight of alkyl-cyclohexane and less than 15% in weight of alkyl-benzene.
  • the hydro-oxygenation and hydro-isomerisation conditions are: 300 to 450° C. of temperature, 1.0 to 6.0 MPa of pressure, between 0.5 to 5 h ⁇ 1 of hourly space velocity and 500 to 2000 LN of H 2 /L of load.
  • EP 0126168 related with a process for the selective reduction of edible oils and fats, that employs a catalyst and a fixed bed to carry out a hydrogenation process.
  • the document teaches the hydrogenation method and the types of vegetable oils that can be employed, in which they are included the palm oil.
  • This process employs nickel catalysts and the hydrotreatment conditions are: 150 to 260° C. of temperature, around 11.0 MPa and 0.2 to 20 h ⁇ 1 of hourly space velocity.
  • the claimed process comprises steps of preheating, mixture of oil with hydrogen, heating, reaction, separation by decantation and eventually distillation or crystallization, as it is shown in FIG. 1 .
  • the sequence of the steps that characterize this invention are explained bellow:
  • the oil and the hydrogen are mixed in the pipeline and are passed through a furnace to heat it to the desired temperature.
  • the hydrogen reacts with the oil on the active sites of the catalyst at pressures between 2 and 11 MPa and temperature between 150° C. and 330° C., with an hourly space velocity between 0.2 and 6 h ⁇ 1 .
  • the employed catalyst is of fixed bed, composed of nickel and molybdenum oxides supported on alumina that were previously sulphurized for their activation.
  • the hydrated product exits the lower part of the reactor and passes to a level separator, where the gas is removed through the upper part and the hydrated liquid product through the bottom.
  • This last is composed of two phases (water and paraffin), which are separated by decantation and according with the desired concentration of high molecular weight paraffins it can be done a distillation separation step, to remove the paraffins with lower molecular weight.
  • the operational conditions that is, pressure, temperature, hourly space velocity and hydrogen/load ratio, to obtain the product in a solid state in the reaction step, are specific for each catalyst, either fresh or used, and are determined according with a pre-established protocol.
  • FIG. 1 Scheme of the hydrotreatment process of palm oil for the obtaining of solid paraffins
  • FIG. 1 it is presented the detail of the flow diagram of the hydroteatment unit where the solid paraffin is obtained.
  • the load to process that in this case is vegetable oil or animal fat, is introduced in the load drum ( 1 ), from where it is pumped and mixed ( 2 ) with the hydrogen to pass to the heating furnace ( 3 ) where the oil/hydrogen mixture acquires the adequate temperature to pass to the reactor ( 4 ).
  • the products of the reaction pass to the decanting separation system ( 5 ), that generally is formed by various steps to achieve the required qualities.
  • the most convenient conformation of the steps of decantation separation are well known and used by the hydrotreatment industry.
  • this step there are obtained three main currents: one gaseous conformed by hydrogen along with the reaction gases; one liquid phase constituted by the obtained products from the oil and another liquid phase corresponding to the by-product water of the reaction (C).
  • the gaseous phase obtained in step ( 5 ) passes to a cleaning step ( 6 ) to purify the hydrogen from gases produced during the reaction such as CO, CO 2 and methane by washing techniques known in the industry, to obtain a high purity hydrogen which is compressed ( 7 ) and is mixed with the replacement hydrogen to maintain the stock and is recycled before the steps of heating and reaction.
  • gases produced during the reaction such as CO, CO 2 and methane by washing techniques known in the industry
  • the claimed process comprises the steps shown in the flow diagram of FIG. 1 , where from the storing tank ( 1 ), with heating, the vegetable oil, from algae or other vegetal origin or animal fat its pumped to the furnace ( 3 ).
  • the vegetable oil or the animal fat is combined with the hydrogen in the mixer ( 2 ), which can be located before or after the furnace ( 3 ), where the load is heated to the desired temperature at the entrance of the reactor ( 4 ).
  • the reaction is done, that being exothermic it makes the load temperature to rise as it goes through the catalytic bed.
  • the product from the reaction is taken to a separating reservoir ( 5 ) where the gaseous hydrogen is recovered to purify it ( 6 ) and recycle it to the process.
  • the water and the solid paraffinic compounds that due to the high temperatures of the process remain in liquid state are separated by decantation. Such paraffinic compounds are recovered for their storage.
  • reaction operational conditions that is, pressure, temperature, hourly space velocity, to obtain the product in a solid state are specific for each catalyst, either fresh or used, and are determined according with a pre-established protocol in which two variables are fixed and the third is established with the purpose of preventing the formation of light paraffins.
  • the applicant considers that in this way the hydrotreatment reaction is interrupted before the molecules are saturated with hydrogen, with which free radicals are produced that then are combined forming high molecular weight paraffinic compounds, which are solid at room temperature.
  • the catalyst is a fresh or used catalyst that comprises a support of porous alumina impregnated with metallic sulfides of Ni and Mo or of Ni and Co.
  • the vegetable oil is selected from the following group of oils: soy oil, palm oil, canola oil, castor oil, jatropha oil, among others.
  • the solid paraffinic compounds that are produced through the process here described have its principal use in the elaboration of candles.
  • the paraffinic compounds obtained are of high refinement and purity and are safe to use as paper coatings for packing, prepare, transport, treat or store food with which it must be in contact with.
  • the solid paraffins of the invention can also be employed in corrugated contents to pack vegetables, fruits, meat, fish and cheeses; as well as in paper cups. They are also used in the lid of the canned foods to prevent the food from dehydration and mold formation. In addition, they are added to chewing gum due to its plasticity.
  • table 4 there are registered the results of the comparative analysis of the absorbance for the paraffin of the invention and the paraffin obtained from a petroleum derivative, compared with the established standards for paraffin according to the FDA.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Fats And Perfumes (AREA)
US13/142,101 2008-12-12 2009-11-24 Method for obtaining solid paraffinic compounds by hydrotreatment of vegetable oils Abandoned US20120041240A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CO08132107A CO6170075A1 (es) 2008-12-12 2008-12-12 Proceso para la obtencion de compuestos parafinicos solidos por hidrotratamiento de aceites vegetales
CO08-132107 2008-12-12
PCT/IB2009/007648 WO2010067164A1 (es) 2008-12-12 2009-11-24 Proceso para la obtención de compuestos parafinicos sólidos por hidrotratamiento de aceites vegetales

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US20120041240A1 true US20120041240A1 (en) 2012-02-16

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US13/142,101 Abandoned US20120041240A1 (en) 2008-12-12 2009-11-24 Method for obtaining solid paraffinic compounds by hydrotreatment of vegetable oils

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BR (1) BRPI0923430B1 (pt)
CO (1) CO6170075A1 (pt)
WO (1) WO2010067164A1 (pt)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120261567A1 (en) * 2011-03-17 2012-10-18 Colorado School Of Mines Metal oxide laser ionization-mass spectrometry
US10351782B2 (en) * 2014-09-12 2019-07-16 Council Of Scientific And Industrial Process to produce aromatics rich aviation fuel along with other C1-C24 hydrocarbons

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070131579A1 (en) * 2005-12-12 2007-06-14 Neste Oil Oyj Process for producing a saturated hydrocarbon component
US20070260102A1 (en) * 2006-04-17 2007-11-08 Petroleo Brasileiro S.A.-Petrobras Process to obtain N-paraffins from vegetable oil
US20080308458A1 (en) * 2007-06-15 2008-12-18 E. I. Du Pont De Nemours And Company Catalytic process for converting renewable resources into paraffins for use as diesel blending stocks

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BRPI0500591A (pt) * 2005-02-18 2006-10-03 Petroleo Brasileiro Sa processo para a hidroconversão de óleos vegetais
US7459597B2 (en) * 2005-12-13 2008-12-02 Neste Oil Oyj Process for the manufacture of hydrocarbons

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US20070131579A1 (en) * 2005-12-12 2007-06-14 Neste Oil Oyj Process for producing a saturated hydrocarbon component
US20070260102A1 (en) * 2006-04-17 2007-11-08 Petroleo Brasileiro S.A.-Petrobras Process to obtain N-paraffins from vegetable oil
US20080308458A1 (en) * 2007-06-15 2008-12-18 E. I. Du Pont De Nemours And Company Catalytic process for converting renewable resources into paraffins for use as diesel blending stocks

Non-Patent Citations (3)

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Title
Anneken, D.J., Both, S., Christoph, R., Fieg, G., Steinberner, U. and Westfechtel, A. 2006. Fatty Acids. Ullmann's Encyclopdia of Industrial Chemistry, p. 101-102. *
R. K. Sinnott, Coulson & Richardson's Chemical Engineering: Chemical Engineering Design, Volume 6, Fourth Edition, 2005, p. 50 *
Wang, C. and Erhan, S., Studies of Thermal Polymerization of Vegetable Oils with a Differential Scanning Calorimeter, JAOCS, Vol. 76, no. 10, 1999, p. 1211-12-16 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120261567A1 (en) * 2011-03-17 2012-10-18 Colorado School Of Mines Metal oxide laser ionization-mass spectrometry
US10079139B2 (en) * 2011-03-17 2018-09-18 Kent J. Voorhees Metal oxide laser ionization-mass spectrometry
US10351782B2 (en) * 2014-09-12 2019-07-16 Council Of Scientific And Industrial Process to produce aromatics rich aviation fuel along with other C1-C24 hydrocarbons

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CO6170075A1 (es) 2010-06-18
WO2010067164A1 (es) 2010-06-17
BRPI0923430A2 (pt) 2016-08-23
BRPI0923430B1 (pt) 2018-05-08

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