EP0381604B1 - Procédé pour améliorer l'indice de cétane des gazoles de viscoréduction - Google Patents

Procédé pour améliorer l'indice de cétane des gazoles de viscoréduction Download PDF

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Publication number
EP0381604B1
EP0381604B1 EP90420053A EP90420053A EP0381604B1 EP 0381604 B1 EP0381604 B1 EP 0381604B1 EP 90420053 A EP90420053 A EP 90420053A EP 90420053 A EP90420053 A EP 90420053A EP 0381604 B1 EP0381604 B1 EP 0381604B1
Authority
EP
European Patent Office
Prior art keywords
hydrogen peroxide
visbreaking
gas oils
formic acid
process according
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.)
Expired - Lifetime
Application number
EP90420053A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0381604A1 (fr
Inventor
Bernard Dubreux
Philippe Mulard
Michèle Pralus
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.)
Arkema France SA
Original Assignee
Elf Atochem SA
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
Application filed by Elf Atochem SA filed Critical Elf Atochem SA
Publication of EP0381604A1 publication Critical patent/EP0381604A1/fr
Application granted granted Critical
Publication of EP0381604B1 publication Critical patent/EP0381604B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • C10G55/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one refining process and at least one cracking process
    • C10G55/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one refining process and at least one cracking process plural serial stages only
    • C10G55/04—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one refining process and at least one cracking process plural serial stages only including at least one thermal cracking step
    • 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
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/12—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen with oxygen-generating compounds, e.g. per-compounds, chromic acid, chromates
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00—Engines characterised by air compression and subsequent fuel addition
    • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B47/00—Methods of operating engines involving adding non-fuel substances or anti-knock agents to combustion air, fuel, or fuel-air mixtures of engines

Definitions

  • the present invention relates to a method for improving the cetane number of visbreaking gas oils and the gas oils with cetane number thus improved.
  • Diesel oil proper is the middle distillate, intermediate between light distillates, gas and gasoline, and heavier products, in the distillation at atmospheric pressure by which the refining of crude oils begins. Said diesel is mainly intended for the supply of diesel engines and for domestic heating.
  • US Pat. No. 1,972,102 describes a process for removing sulfur-containing compounds from hydrocarbons, in particular from gas oils, consisting in washing the hydrocarbon with an aqueous solution containing acetic acid and hydrogen peroxide, then in separating said solution of the hydrocarbon.
  • gas oils which thus derive directly from crude oils, or direct gas oils, must have a sufficiently high capacity for ignition by compression, reflected by their cetane number.
  • visbreaking is a thermal cracking which reduces, as its name suggests, the viscosity of the petroleum product to which it is applied. It is essentially different in nature from, for example, of a catalytic cracking to which said petroleum product can also be subjected. It delivers a product, called visbreaking diesel, itself essentially different from direct diesel or catalytic cracking.
  • the visbreaking gas oils can only be used as motor gas oils because of their too low cetane number that the additives which are suitable for direct gas oils improve only insufficiently.
  • the present invention makes it possible to improve the cetane index of visbreaking gas oils up to values which allow their recovery directly in the fields of use of direct gas oils.
  • the method according to the invention for improving the cetane index of a visbreaking diesel fuel is characterized in that said diesel fuel is brought into contact either with hydrogen peroxide in the presence of formic acid, or with acid performic in the presence or not of hydrogen peroxide.
  • the method according to the invention not only allows a substantial increase in the cetane number of the visbreaking gas oil to which it is applied but also leads to deodorization and discoloration of said gas oil.
  • the organic phase which is then separated by decantation from the mixture, which is left to stand and cooled, is washed so that the hydrogen peroxide and formic acid which may remain in the gas oil after treatment are removed from it. Washing is most commonly done using water.
  • the cetane index of the starting visbreaking diesel measured by applying standard ASTM-D 613, is equal to 39. That of visbreaking diesel after applying the process according to the invention is 50.
  • the diesel fuel resulting from the process of the invention is strongly deodorized compared to the starting diesel fuel from which it is further distinguished by a coloring, expressed in HAZEN degree after dilution of factor 100 of the sample in acetone, 5 times lower. .
  • Example 1 The operating process described in Example 1 is followed, with the same starting visbreaking gas oil in kind as in quantity, but using 0.26 mole of formic acid and 2.6 moles of hydrogen peroxide under form of 126 g. of an aqueous solution at 70% by weight of hydrogen peroxide.
  • the visbreaking diesel obtained at the end of the process according to the invention has a cetane number equal to 53.5, is strongly deodorized and is still 5 times less colored than initially.
  • Example 1 is repeated, replacing the formic acid with 0.13 mole of acetic acid, a result similar to that obtained in Example 1 is obtained, but after a contact time equal to almost twice that chosen. in example 1.

Landscapes

  • 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)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Fluid-Damping Devices (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treating Waste Gases (AREA)
  • Electrical Control Of Air Or Fuel Supplied To Internal-Combustion Engine (AREA)
  • Respiratory Apparatuses And Protective Means (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
EP90420053A 1989-02-03 1990-02-01 Procédé pour améliorer l'indice de cétane des gazoles de viscoréduction Expired - Lifetime EP0381604B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8901657A FR2642766B1 (fr) 1989-02-03 1989-02-03 Procede pour ameliorer l'indice de cetane des gazoles de viscoreduction
FR8901657 1989-02-03

Publications (2)

Publication Number Publication Date
EP0381604A1 EP0381604A1 (fr) 1990-08-08
EP0381604B1 true EP0381604B1 (fr) 1993-05-12

Family

ID=9378611

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90420053A Expired - Lifetime EP0381604B1 (fr) 1989-02-03 1990-02-01 Procédé pour améliorer l'indice de cétane des gazoles de viscoréduction

Country Status (10)

Country Link
US (1) US5114434A (da)
EP (1) EP0381604B1 (da)
JP (1) JPH0649871B2 (da)
AT (1) ATE89309T1 (da)
CA (1) CA2009217A1 (da)
DE (2) DE69001555T2 (da)
DK (1) DK0381604T3 (da)
ES (1) ES2017902T3 (da)
FR (1) FR2642766B1 (da)
GR (1) GR900300146T1 (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2701118B1 (fr) * 1993-02-01 1995-04-21 Elf Antar France Procédé de mesure de l'indice de cétane de carburants d'alimentation des moteurs diesels et dispositif pour la mise en Óoeuvre de ce procédé.
US6461497B1 (en) 1998-09-01 2002-10-08 Atlantic Richfield Company Reformulated reduced pollution diesel fuel
FR2821350B1 (fr) * 2001-02-26 2004-12-10 Solvay Procede de desulfuration d'un melange d'hydrocarbures
US6673236B2 (en) 2001-08-29 2004-01-06 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Natural Resources Method for the production of hydrocarbon fuels with ultra-low sulfur content
EP1509493A2 (de) * 2002-05-31 2005-03-02 Henkel Kommanditgesellschaft auf Aktien Desodorierung von kationischen ammoniumacetonitrilderivaten
DE10224509C1 (de) * 2002-05-31 2003-11-20 Henkel Kgaa Desodorierung von kationischen Acetonitrilderivaten
US8920633B2 (en) * 2009-09-16 2014-12-30 Cetamax Ventures Ltd. Method and system for oxidatively increasing cetane number of hydrocarbon fuel
US9453177B2 (en) 2009-09-16 2016-09-27 Cetamax Ventures Ltd. Method and system for oxidatively increasing cetane number of hydrocarbon fuel

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1972102A (en) * 1930-12-12 1934-09-04 Atlantic Refining Co Hydrocarbon oil treatment
FR758567A (fr) * 1933-07-18 1934-01-19 Procédé pour réduire la teneur en soufre des benzines, essences, huiles minérales et huiles de goudron
GB443562A (en) * 1934-06-29 1936-03-02 Alfred Charles Glyn Egerton Improved fuels for internal-combustion engines
US2092322A (en) * 1934-09-14 1937-09-07 Shell Dev Process for the production of organic peroxides
US2296558A (en) * 1938-09-20 1942-09-22 Autoxygen Inc Liquid fuel for internal combustion engines
US2403772A (en) * 1943-11-15 1946-07-09 Shell Dev Production of organic hydroperoxides
US2403771A (en) * 1943-11-15 1946-07-09 Shell Dev Organic peroxides
US2472152A (en) * 1944-08-05 1949-06-07 Union Oil Co Diesel engine fuel
US2481859A (en) * 1946-08-31 1949-09-13 Standard Oil Dev Co Diesel fuel
US3035904A (en) * 1953-10-07 1962-05-22 Diesel fuel compositions
US2912313A (en) * 1956-03-30 1959-11-10 Ethyl Corp Diesel fuel
FR1192214A (fr) * 1956-09-13 1959-10-23 Res Ltd Procédé d'amélioration des huiles de graissage hydrocarbonées
US3719589A (en) * 1971-03-05 1973-03-06 Texaco Inc Asphalt separation in desulfurization with an oxidation step
US3827979A (en) * 1971-05-03 1974-08-06 Mobil Oil Corp Overbasing manganese compounds with promoters and copromoters
US4289501A (en) * 1978-03-20 1981-09-15 Bwm Corporation Hydrocarbon fuel additive
US4248182A (en) * 1979-09-04 1981-02-03 Ethyl Corporation Anti-wear additives in diesel fuels
FR2464947A1 (fr) * 1979-09-07 1981-03-20 Ugine Kuhlmann Procede de fabrication d'acides percarboxyliques
US4286964A (en) * 1979-10-12 1981-09-01 Seed Brian S Polyfunctional epoxides and halohydrins used as bridging groups to bind aromatic amine group-containing alcohols and thiols to hydroxyl bearing substrates
US4474574A (en) * 1982-01-11 1984-10-02 Alza Corporation Formulation dispenser for use with a parenteral delivery system
US4406254A (en) * 1982-02-10 1983-09-27 General Motors Corporation Method for lean operation of spark-ignited gasoline-fueled reciprocating engine
US4482352A (en) * 1984-03-05 1984-11-13 Fuel-X-Tender Corporation Fuel additive
US4711713A (en) * 1986-02-24 1987-12-08 Rei Technologies, Inc. Process for enhancing the cetane number and color of diesel fuel
EP0252606A3 (en) * 1986-06-09 1989-03-15 Exxon Research And Engineering Company Process for increasing the cetane number of diesel fuels

Also Published As

Publication number Publication date
FR2642766A1 (fr) 1990-08-10
DE69001555T2 (de) 1993-10-21
DE69001555D1 (de) 1993-06-17
DK0381604T3 (da) 1993-06-07
ES2017902A4 (es) 1991-03-16
EP0381604A1 (fr) 1990-08-08
JPH02240195A (ja) 1990-09-25
JPH0649871B2 (ja) 1994-06-29
DE381604T1 (de) 1991-01-17
US5114434A (en) 1992-05-19
ATE89309T1 (de) 1993-05-15
FR2642766B1 (fr) 1993-12-24
ES2017902T3 (es) 1993-11-16
CA2009217A1 (fr) 1990-08-03
GR900300146T1 (en) 1991-09-27

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