WO2016100018A1 - Produits hydrocarbures - Google Patents

Produits hydrocarbures Download PDF

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Publication number
WO2016100018A1
WO2016100018A1 PCT/US2015/064587 US2015064587W WO2016100018A1 WO 2016100018 A1 WO2016100018 A1 WO 2016100018A1 US 2015064587 W US2015064587 W US 2015064587W WO 2016100018 A1 WO2016100018 A1 WO 2016100018A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrocarbon product
hydrocarbon
approximately
peak
infrared spectroscopy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2015/064587
Other languages
English (en)
Inventor
Kyle E. Litz
Jonathan P. Rankin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cenovus Energy Inc
Auterra Inc
Original Assignee
Cenovus Energy Inc
Auterra Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US14/573,230 external-priority patent/US20150337220A1/en
Application filed by Cenovus Energy Inc, Auterra Inc filed Critical Cenovus Energy Inc
Publication of WO2016100018A1 publication Critical patent/WO2016100018A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/06—Liquid carbonaceous fuels essentially based on blends of hydrocarbons for spark ignition
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
    • C10G2300/203—Naphthenic acids, TAN
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/301—Boiling range
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/302—Viscosity
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/02—Gasoline

Definitions

  • Crude oil contains heteroatoms such as sulfur, nitrogen, nickel, vanadium and acidic oxygenates in quantities that negatively impact the refinery processing of the crude oil fractions.
  • Light crude oils or condensates contain heteroatoms in concentrations as low as 0.001 wt %.
  • heavy crude oils contain heteroatoms as high as 5-7 Wt %.
  • the heteroatom content of crude oil increases with increasing boiling point and the heteroatom content increases with decreasing API gravity.
  • a second embodiment of this disclosure relates generally to a hydrocarbon product comprising at least 0.1 grams per gram of the hydrocarbon product has a boiling point greater than 738°C, up to 0.1 mass% of the hydrocarbon product is insoluble in pentane and the hydrocarbon product exhibits an infrared spectroscopy reference peak, centered between approximately 1445 cm -1 and 1465 cm -1 , a first infrared spectroscopy peak between approximately 1310cm -1 and 1285cm -1 , and a second infrared spectroscopy peak between approximately 1135cm -1 and 1110cm -1 , wherein a height or area of the first infrared spectroscopy peak is at least approximately 28% of a height or area of the infrared spectroscopy reference peak and a height or area of the second infrared spectroscopy peak is at least approximately 22% of the height or area of the infrared spectroscopy reference peak.
  • Fig. 5b depicts an alternate embodiment of a biphasic reaction mechanism, forming a hydrocarbon product and a bisulfite salt.
  • API gravity refers to American Petroleum Institute gravity ("API gravity”) at 15.5°C (approximately 60°F), unless stated otherwise. API gravity may be determined by ASTM Method D6822 or equivalent method. API gravity, is a measure of how heavy or light a petroleum liquid is compared to water. If its API gravity is greater than 10, it is lighter and floats on water; if less than 10, it is heavier and sinks. API gravity is thus an inverse measure of the relative density of a petroleum liquid and the density of water, but it is used to compare the relative densities of petroleum liquids. For example, if one petroleum liquid floats on another and is therefore less dense, it has a greater API gravity.
  • Boiling range distributions for hydrocarbons and hydrocarbon containing material may be as determined by ASTM Method D5307, ASTM Method D7169 or equivalent method. Some methods testing the boiling range distribution of a water-free crude petroleum may determine the boiling range through approximately 538°C. In such an embodiment, materials that boil above 538°C may be reported as residue. In other embodiments of methods for identifying the boiling range distribution, the method may determine boiling point distribution and cut point intervals of hydrocarbons such as crude oils and residues by using high temperature gas chromatography. The method may extend the applicability of simulated distillation to samples that do not elute completely from chromatographic systems.
  • the range for diesel boiling points may be identified using a method that establishes a boiling point distribution range up through 720°C which may correspond to the elution of C n - C 100 hydrocarbon compounds.
  • tests may use capillary columns with thin films, which results in the incomplete separation of C 4 -C 8 in the presence of large amounts of carbon disulfide, and thus yields an unreliable boiling point distribution corresponding to this elution interval.
  • quenching of the response of the detector employed to hydrocarbons eluting during carbon disulfide elution may result in unreliable quantitative analysis of the boiling distribution in the C 4 -C 8 region.
  • Diesel refers to hydrocarbons with a boiling range distribution from approximately 250°C up to approximately 350°C as determined in accordance with ASTM Method D5307, ASTM Method D7169 or equivalent method. Diesel content may be determined by the quantity of hydrocarbons having a boiling range between 250 - 350°C relative to the quantity of hydrocarbons as measured by the boiling range distribution.
  • the content of hydrocarbon components for example parafins, iso-parafins, olefins, naphthanenes and aromatics in naphtha may be determined by ASTM Method D6730 or equivalent method.
  • Methods for identifying the hydrocarbon components may include chromatographic operating conditions and column tuning processes to provide and enhance the separation and subsequent determination of many individual components that may not obtained with previous single-column analyses.
  • the column temperature program profile may be selected to afford the maximum resolution of possible co-eluting components, for example, where there are of two different compound types (such as a paraffin and a naphthene).
  • Residue or residual refers to a hydrocarbon that has a boiling range distribution above 538° C. (1000° F.), as determined by ASTM Method D5307, ASTM Method D7169, or an equivalent method thereof.
  • the residual portion of a hydrocarbon mixture of a hydrocarbon product may include coke, asphalt, tar and waxes.
  • the hydrocarbon fraction may include multi-ringed structures having a carbon chain of approximately 70 or more carbon atoms per molecule.
  • Total base number is a measure of a petroleum product's reserve alkalinity. It is measured in milligrams of potassium hydroxide per gram (mg KOH/g). TBN determines how effective the control of acids formed will be during the combustion process. The higher the TBN, the more effective it is in suspending wear-causing contaminants and reducing the corrosive effects of acids and acidic byproducts over an extended period of time. TBN may be determined using ASTM D2896 or an equivalent method thereof. Embodiments of methods for calculating TBN may make a determination of basic constituents in hydrocarbon products by titration with perchloric acid in glacial acetic acid.
  • Disadvantaged crudes may include at least 0.001 grams of hydrocarbons per grams of disadvantaged crudes having a boiling range distribution between 95° C and 200° C at 0.101 MPa; at least 0.001 grams of hydrocarbons per gram of disadvantaged crude with a boiling range distribution between 200° C. and 300° C at 0.101 MPa; at least 0.001 grams hydrocarbons per gram of crude with a boiling range distribution between 300° C and 400° C at 0.101 MPa; and at least 0.001 grams of hydrocarbons per gram of disadvantaged crude with a boiling range distribution between 400° C and 650° C at 0.101 MPa.
  • the initial reaction may be a hydroxyl attack on the C-S bond of the sulfur containing compound present in in the sulfone/sulfoxide rich oxidized heteroatom containing stream, such as in a dibenzothiophene sulfone depicted in Fig. 4.
  • a hydrocarbon containing a sulfonate group may form as a reaction intermediate.
  • Fig. 5 provides one possible explanation for the reaction mechanism.
  • Embodiments may include introducing an excess molar ratio of selectivity promoters to caustic cations for increased conversion and selectivity.
  • the API gravity of the hydrocarbon product 120 produced from the caustic treatment may be between 10 and 30. In other embodiments, the API gravity of the hydrocarbon product may be increased by at least 3 units over the API gravity of the hydrocarbon feed 101, at least 10 units over the API gravity of the hydrocarbon feed or at least 15 units over the API gravity of the hydrocarbon feed 101. In yet another embodiment, the API gravity of the hydrocarbon product may be at least 12, at least 15, at least 20 or at least 25.
  • the oxygen content of the hydrocarbon product may be at most 90% of the hydrocarbon feed. In other embodiments, the oxygen content may be at most 50%, at most 30%, at most 10% or at most 5% of the oxygen content of the hydrocarbon feed. In certain embodiments, the oxygen content may be less than approximately 1.2 wt% of the hydrocarbon product.
  • the hydrocarbon products may contain at least 0.75 grams of hydrocarbons per gram of hydrocarbon product having a boiling range distribution from the IBP of the hydrocarbon products 120 up to 739°C.
  • the hydrocarbon products 120 may include at most 0.3grams of hydrocarbons per gram of hydrocarbon products having a boiling range distribution greater than 738°C.
  • Embodiments of the hydrocarbon products may contain at least 0.2g of fuel oils, greases, waxes and/or some bitumens per gram hydrocarbon product. In other embodiments, the hydrocarbon product may contain at most 0.8g of fuel oils, greases, waxes and/or some bitumens per gram hydrocarbon product. The fuel oils, greases, waxes and/or some bitumens may have a boiling range distribution between approximately 343°C and 510°C.
  • intermediate products 111 may be characterized by the presence of infrared spectroscopy peaks identified by one or more peaks recorded using IR spectroscopy.
  • the peaks may be referred to as a first, second, third, fourth or fifth peak, etc., however name of the peak denotes the order in which the peak is discussed.
  • the location and identifying nature of the peak may be based on the wavelength or wavenumber where the peak may be located during IR spectroscopy, not the designation of the peak as the first, second or third, etc.
  • Embodiments of the hydrocarbon products 120 may exhibit a second peak with height or area that is approximately at least 22% of the height or area of the reference peak.
  • the second peak may vary in height or area, for example, the height or area of the second peak may be at least 25%, at least 30%, at least 40%, at least 50%, at least 70%, at least 85%, at least 100% or greater than 100% of the height or area of the reference peak.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

La présente invention concerne un produit hydrocarbure contenant au moins 0,1 gramme par gramme de produit hydrocarbure présentant une distribution d'intervalle de distillation d'un point d'ébullition initial à approximativement 739 °C, les produits hydrocarbures étant caractérisés en outre par un pic de référence de spectroscopie infrarouge centré entre approximativement 1445 cm-1 et 1465 cm-1, un premier pic de spectroscopie infrarouge entre approximativement 1310 cm-1 et 1285 cm-1, la hauteur du premier pic de spectroscopie infrarouge étant au moins approximativement 28 % de la hauteur du pic de référence de spectroscopie infrarouge et un deuxième pic de spectroscopie infrarouge entre approximativement 1135 cm-1 et 1110 cm-1, la hauteur du deuxième pic de spectroscopie infrarouge étant au moins approximativement 22 % de la hauteur du pic de référence de spectroscopie infrarouge.
PCT/US2015/064587 2014-12-17 2015-12-09 Produits hydrocarbures Ceased WO2016100018A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14/573,230 US20150337220A1 (en) 2014-05-23 2014-12-17 Hydrocarbon products
US14/573,230 2014-12-17

Publications (1)

Publication Number Publication Date
WO2016100018A1 true WO2016100018A1 (fr) 2016-06-23

Family

ID=56127368

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2015/064587 Ceased WO2016100018A1 (fr) 2014-12-17 2015-12-09 Produits hydrocarbures

Country Status (2)

Country Link
TW (1) TW201629193A (fr)
WO (1) WO2016100018A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2789134A (en) * 1953-06-19 1957-04-16 Exxon Research Engineering Co Recovery of naphthenic acids
US6087662A (en) * 1998-05-22 2000-07-11 Marathon Ashland Petroleum Llc Process for analysis of asphaltene content in hydrocarbon mixtures by middle infrared spectroscopy
US20110178346A1 (en) * 2010-01-21 2011-07-21 Stanley Nemee Milam Hydrocarbon composition
US20110210043A1 (en) * 2003-12-19 2011-09-01 Scott Lee Wellington Crude product composition
US20140024569A1 (en) * 2012-07-17 2014-01-23 Tushar K. Bera Lubricating Oil Compositions Containing Sterically Hindered Amines as Ashless TBN Sourcces
WO2014095813A1 (fr) * 2012-12-17 2014-06-26 Shell Internationale Research Maatschappij B.V. Procédé de préparation d'une hydrocire
US20150337208A1 (en) * 2014-05-23 2015-11-26 Auterra, Inc. Hydrocarbon products

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2789134A (en) * 1953-06-19 1957-04-16 Exxon Research Engineering Co Recovery of naphthenic acids
US6087662A (en) * 1998-05-22 2000-07-11 Marathon Ashland Petroleum Llc Process for analysis of asphaltene content in hydrocarbon mixtures by middle infrared spectroscopy
US20110210043A1 (en) * 2003-12-19 2011-09-01 Scott Lee Wellington Crude product composition
US20110178346A1 (en) * 2010-01-21 2011-07-21 Stanley Nemee Milam Hydrocarbon composition
US20140024569A1 (en) * 2012-07-17 2014-01-23 Tushar K. Bera Lubricating Oil Compositions Containing Sterically Hindered Amines as Ashless TBN Sourcces
WO2014095813A1 (fr) * 2012-12-17 2014-06-26 Shell Internationale Research Maatschappij B.V. Procédé de préparation d'une hydrocire
US20150337208A1 (en) * 2014-05-23 2015-11-26 Auterra, Inc. Hydrocarbon products

Also Published As

Publication number Publication date
TW201629193A (zh) 2016-08-16

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