EP0482841A1 - Désulfurisation d'huile - Google Patents
Désulfurisation d'huile Download PDFInfo
- Publication number
- EP0482841A1 EP0482841A1 EP91309649A EP91309649A EP0482841A1 EP 0482841 A1 EP0482841 A1 EP 0482841A1 EP 91309649 A EP91309649 A EP 91309649A EP 91309649 A EP91309649 A EP 91309649A EP 0482841 A1 EP0482841 A1 EP 0482841A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- sulphur
- molybdenum
- tungsten
- oil
- vanadium
- 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
Links
- 239000003921 oil Substances 0.000 claims abstract description 41
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000005864 Sulphur Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 24
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 22
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 22
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 21
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 12
- 239000011733 molybdenum Substances 0.000 claims abstract description 12
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 12
- 239000010937 tungsten Substances 0.000 claims abstract description 12
- 239000007800 oxidant agent Substances 0.000 claims abstract description 11
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 11
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000001590 oxidative effect Effects 0.000 claims abstract description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 4
- 239000011574 phosphorus Substances 0.000 claims abstract description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052796 boron Chemical group 0.000 claims abstract description 3
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 3
- 239000010703 silicon Chemical group 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011964 heteropoly acid Substances 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 3
- 235000019198 oils Nutrition 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 4
- UKEYAMZBIGBEQL-UHFFFAOYSA-N tri(octanoyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC(=O)[NH+](C(=O)CCCCCCC)C(=O)CCCCCCC UKEYAMZBIGBEQL-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- -1 sulphur compound Chemical class 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000012505 colouration Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
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
- 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
Definitions
- the present invention relates to a process for oxidising sulphur derivatives useful in the removal of unwanted sulphur from sulphur containing hydrocarbon oils.
- Heavy oils occur widely throughout the world and contain significant quantities of chemically bound sulphur.
- the presence of sulphur poses problems in that it poisons many catalytic systems employed in processes to convert heavy hydrocarbon fractions to lighter oils and gasolines.
- the combustion of such sulphur containing oils leads to the release of undesirable sulphur containing species known to add to atmospheric pollution.
- US 3551328 discloses a process for the desulphurisation of heavy hydrocarbon fractions by the oxidation of the sulphur impurities by contacting the hydrocarbon fraction with an oxidant in the presence of an oxidation promoting catalyst and further treatment with a lower paraffinic hydrocarbon solvent to separate the oxidised sulphur compounds from the hydrocarbon fraction.
- US 3565793 discloses a process for the desulphurisation of hydrocarbon materials by the oxidation of the sulphur impurities and subsequent removal of the oxidised sulphur compound by thermal treatment or addition of a base.
- US 3595778 discloses a desulphurisation process comprising the oxidation of the sulphur containing compounds by ozone and a vanadium catalyst followed by thermal or base treatment.
- US 3847800 discloses a process wherein sulphur and nitrogen components are removed from petroleum oils comprising reacting the petroleum oils with a gas which includes one or more oxides of nitrogen and mixing the oxidised oil with a solvent immiscible with the oil.
- the present invention comprises a process for desulphurising hydrocarbon oils comprising the steps of (1) treating a sulphur containing hydrocarbon oil with a catalyst consisting essentially of an aqueous acidic or neutral solution of a molybdenum, tungsten or vanadium heteropolyanion and an oxidant under conditions such that the sulphur is oxidised and (2) separating the oxidised sulphur from the treated hydrocarbon oil.
- the present invention has the advantage that operating conditions are mild and selectivity to sulphur oxidation is high without significant amounts of unwanted side reactions.
- the catalyst used to effect oxidation of the sulphur is a molybdenum, tungsten or vanadium heteropolyanion. Such species are described in detail in 'Heteropoly and Isopoly Oxo-metalates' by Pope et al , Springer-Verlag, New York 1983.
- a preferred class of heteropolyanions for use in the process of the present invention are those derivable by ionisation of heteropolyacids having the general formula H e (X k M n O y ) where X is phosphorus, antimony, silicon, germanium or boron and M is molybdenum, tungsten or vanadium. It is also preferred that k is from 1 to 5, n is from 5 to 40 and y is from 18 to 62. It will be appreciated that the value of e will equal the valence of the anion (X k M n O y ) e- which in turn will depend upon the value of the other variables.
- a particularly preferred class of heteropolyanions are those having the general formula (XM12O40)3 ⁇ . Of these, the most preferred are those of formula (PM12O40)3 ⁇ where M is either molybdenum or tungsten.
- Such species can be conveniently prepared in situ under the reaction conditions from either (1) the corresponding heteropolyacid H3PM12O40 or alkali metal or ammonium salts thereof or (2) a combination of acid, phosphate and tungstate, molybdate or vanadate salts or acids.
- the volume of the aqueous catalyst phase used should be in the range 0.1 to 10 times the volume of the oil.
- the amount of catalyst should range from 0.0001 to 0.1 moles for every litre of water.
- phase transfer catalyst Whilst the oxidation can be carried out by emulsifying the oil and aqueous catalyst phase, it is preferred that oxidation is carried out in the presence of a phase transfer catalyst.
- Suitable phase transfer catalysts are pyridinium, quaternary ammonium or phosphonium salts, for example tricaprylylmethylammonium chloride and tetraoctylammonium bromide.
- the oxidants which may be used in the oxidation step include hydrogen peroxide, alkyl hydroperoxides, eg tertiarybutylhydro peroxide, oxygen and air.
- the preferred oxidant is hydrogen peroxide.
- the amount of oxidant required will largely be dependant on the amount of sulphur present in the oil.
- a mole ratio of oxidant to sulphur from 0.5 to 20 is preferred.
- pressures of up to 5MPa and 25MPa respectively are suitable.
- the oxidised sulphur is separated from the treated oil.
- Such separation can be effected in a number of ways including solvent extraction, adsorption, pyrolysis to form sulphur monoxide and/or sulphur dioxide, acid hydrolysis and precipitation.
- One preferred method however is to contact the treated hydrocarbon oil with an immiscible solvent.
- Preferred solvents include C1 to C4 alcohol and C1 to C4 alcohol/water mixtures, examples of which are methanol or methanol/water.
- the amount of immiscible solvent used is typically in the range 0.5 to 10 times the volume of hydrocarbon oil being treated.
- Another preferred method is adsorption of the sulphur on an active material such as alumina silica charcoal or the like. This can be achieved by, for example, passing the hydrocarbon oil through a bed or column of the material onto which absorption occurs.
- H2O2 (16.8 mmol; 19% by volume) was added to diesel (20.0g, 0.253% wt S) containing tricaprylylammonium chloride (0.25 mmol).
- aqueous solution of phosphomolybdic acid 0.022 mmol.
- the reaction mixture was heated to 60°C for 2.5h. A small amount of a dark brown oil was observed to precipitate from solution whilst the diesel became dark brown-orange in colour.
- the diesel phase was extracted with methanol (2 x 25 cm3 portions) the latter assuming an orange/brown colouration.
- the % sulphur content of the extracted diesel (determined by XRF) was found to be 0.097%.
- H2O2 (16.8 mmol; 19% by volume) was added to diesel (20.0g, 0.253% wt S) containing tricaprylylammonium chloride (0.25 mmol).
- diesel (20.0g, 0.253% wt S) containing tricaprylylammonium chloride (0.25 mmol).
- 7.5 cm3 of an aqueous solution of phosphotungstic acid (0.01 mmol).
- the reaction mixture was heated to 60°C for 2.5h.
- the diesel was extracted with methanol as described in Example 1.
- the %S content of the extracted diesel was found to be 0.085 % wt.
- H2O2 (11.96 mmol, 19% by volume) was added to a diesel (20.1 g, 0.253 % wt S) containing tricaprylylammonium chloride (0.124 mmol).
- methanol (10.15 g) and phosphomolybdic acid H3PMO12O40 (0.022 mmol).
- the reaction mixture was heated to 60°C for 2.5h.
- the methanol phase assumed a dark green/brown colouration but on cooling turned dark orange-brown in colour.
- the diesel was separated and then extracted with a further 25 cm3 of methanol.
- the % S content of the extracted diesel was found to be 0.076 % wt.
- H2O2 (6.38 mmol, 19% by volume) was added to diesel (9.9g) containing tricaprylylammonium chloride (0.124 mmol). To this was added 10.0g of an aqueous solution of phosphotungstic acid (0.03 mmol). The reaction mixture was heated to 60°C for 1.5h. The aqueous phase was separated and this together with H2O2 (14.25 mmol, 19% by volume) was added to diesel (20.1g, 0.253% wt S) containing aliquat 336 (0.124 mmol). The reaction mixture was heated to 60°C for 2 h. A brown oil precipitated from solution and the diesel phase was extracted with methanol as described in Example 1. The % S content of the extracted diesel was 0.085% wt.
- a two-litre glass reactor was charged with 776.8g of a diesel oil (UK winter grade from BP's Grangemouth Refinery, no ignition improver, consisting essentially of straight run non-hydrotreated gas oil, 0.253 wt. % sulphur), phosphotungstic acid (2.5g in 15g water), 'Aliquat 336' (tri-n-octylmethylammonium chloride, 4.15g), and a solution of H2O2 (49.8g 100%) in 388.9g H2O.
- the contents were heated to 60°C and stirred at that temperature for 4 hours, then cooled to 20°C.
- the bulk diesel phase was separated from the aqueous phase and a small pecipitate of a dark brown oil (5g). XRF analysis showed the bulk phase and the precipitate to contain 0.255 and 1.87 wt % sulphur respectively.
- a 187.8g sample of diesel oxidised as described in Example 6 was charged to a 600 cm3 stainless steel Baskerville autoclave which was then capped, leak tested with N2 at 45 bar and then vented to 0 bar gauge and sealed. The contents were stirred at 250 rpm, heated to 400°C over 11 ⁇ 2 h and kept at 400-410°C for one hour. After slow cooling overnight to ambient temperature, the final pressure was 1.0 bar gauge. Nitrogen gas was added to 5 bar gauge and the gases then released through a NaOH (aq) scrubber. The vessel was pressured to 45 bar with N2 and then slowly vented. On opening the vessel a striging odour was apparent. The liquors were collected (182.3g) leaving a small amount of a carbonaceous residue and degassed for 15 mins with a stream of N2. Analysis by XRF showed the presence of 0.177 wt % sulphur.
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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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909023257A GB9023257D0 (en) | 1990-10-25 | 1990-10-25 | Desulphurisation of oil |
| GB9023257 | 1990-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0482841A1 true EP0482841A1 (fr) | 1992-04-29 |
Family
ID=10684350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP91309649A Ceased EP0482841A1 (fr) | 1990-10-25 | 1991-10-18 | Désulfurisation d'huile |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0482841A1 (fr) |
| CA (1) | CA2054070A1 (fr) |
| GB (1) | GB9023257D0 (fr) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5958224A (en) * | 1998-08-14 | 1999-09-28 | Exxon Research And Engineering Co | Process for deep desulfurization using combined hydrotreating-oxidation |
| GB2366803A (en) * | 2000-08-14 | 2002-03-20 | Ici Plc | Sulphur removal from a hydrocarbon stream |
| WO2002026916A1 (fr) * | 2000-09-28 | 2002-04-04 | Sulphco. Inc. | Desulfuration oxydante de combustibles fossiles par ultrasons |
| WO2002031086A1 (fr) * | 2000-10-11 | 2002-04-18 | Consejo Superior De Investigaciones Cientificas | Procede et catalyseurs d'elimination des composes de soufre de la fraction essence |
| WO2002062927A3 (fr) * | 2001-02-08 | 2002-11-14 | Bp Corp North America Inc | Preparation de composants pour carburants de transport |
| WO2002062926A3 (fr) * | 2001-02-08 | 2002-12-12 | Bp Corporationnorth America In | Preparation de composes pour melange de raffinerie de carburants de transport |
| WO2002097006A3 (fr) * | 2001-02-08 | 2003-10-16 | Bp Corp North America Inc | Procede d'oxygenation de composants conçus pour le melange de raffinerie de carburants de transport |
| WO2002062925A3 (fr) * | 2001-02-08 | 2003-11-20 | Bp Corp North America Inc | Preparation integree de composants de melange destinee a des carburants de transport de raffinerie |
| WO2004055135A1 (fr) * | 2002-12-17 | 2004-07-01 | Shell Internationale Research Maatschappij B.V. | Processus d'oxydation selective catalytique de composes de soufre |
| US6872231B2 (en) | 2001-02-08 | 2005-03-29 | Bp Corporation North America Inc. | Transportation fuels |
| US7081196B2 (en) | 2001-05-10 | 2006-07-25 | Mark Cullen | Treatment of crude oil fractions, fossil fuels, and products thereof with sonic energy |
| CN101063044B (zh) * | 2006-04-27 | 2010-06-23 | 中国石油化工股份有限公司 | 一种柴油氧化脱硫方法 |
| US7871512B2 (en) | 2001-05-10 | 2011-01-18 | Petrosonics, Llc | Treatment of crude oil fractions, fossil fuels, and products thereof |
| WO2013052102A1 (fr) * | 2011-10-03 | 2013-04-11 | Alternative Petroleum Technologies Sa | Catalyseurs d'oxydation issus d'hétéropolyacides et de composés azotés quaternisés, procédés de synthèse et d'activation de ces catalyseurs et procédés pour leur utilisation |
| US8663459B2 (en) | 2006-03-03 | 2014-03-04 | Saudi Arabian Oil Company | Catalytic process for deep oxidative desulfurization of liquid transportation fuels |
| EP2745931A1 (fr) | 2012-12-18 | 2014-06-25 | IFP Energies nouvelles | Catalyseur d'hydrotraitement dé résidus d'hydrocarbures comprenant dû vanadium et son utilisation dans un procédé d'hydroconversion dé residus |
| US8926825B2 (en) | 2010-03-19 | 2015-01-06 | Mark Cullen | Process for removing sulfur from hydrocarbon streams using hydrotreatment, fractionation and oxidation |
| WO2017144460A1 (fr) * | 2016-02-26 | 2017-08-31 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Procédé pour la désulfuration par oxydation de carburants liquides |
| WO2022040320A1 (fr) * | 2020-08-19 | 2022-02-24 | Santa Fe Resources Development, Inc. | Procédés et systèmes de réduction de soufre |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3813329A (en) * | 1972-08-18 | 1974-05-28 | Universal Oil Prod Co | Solvent extraction of coal utilizing a heteropoly acid catalyst |
| US3825488A (en) * | 1973-05-07 | 1974-07-23 | Universal Oil Prod Co | Process for hydrorefining a hydrocarbon charge stock |
| US4156641A (en) * | 1978-02-24 | 1979-05-29 | Uop Inc. | Catalytic oxidation of mercaptan in petroleum distillate including quaternary ammonium hydroxide |
| EP0031729A1 (fr) * | 1979-12-31 | 1981-07-08 | E.I. Du Pont De Nemours And Company | Conversion catalytique de butadiène en furane |
| EP0064371B1 (fr) * | 1981-04-24 | 1984-10-24 | Sumitomo Chemical Company, Limited | Hétéropolyacides, leur production et emploi |
-
1990
- 1990-10-25 GB GB909023257A patent/GB9023257D0/en active Pending
-
1991
- 1991-10-18 EP EP91309649A patent/EP0482841A1/fr not_active Ceased
- 1991-10-23 CA CA 2054070 patent/CA2054070A1/fr not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3813329A (en) * | 1972-08-18 | 1974-05-28 | Universal Oil Prod Co | Solvent extraction of coal utilizing a heteropoly acid catalyst |
| US3825488A (en) * | 1973-05-07 | 1974-07-23 | Universal Oil Prod Co | Process for hydrorefining a hydrocarbon charge stock |
| US4156641A (en) * | 1978-02-24 | 1979-05-29 | Uop Inc. | Catalytic oxidation of mercaptan in petroleum distillate including quaternary ammonium hydroxide |
| EP0031729A1 (fr) * | 1979-12-31 | 1981-07-08 | E.I. Du Pont De Nemours And Company | Conversion catalytique de butadiène en furane |
| EP0064371B1 (fr) * | 1981-04-24 | 1984-10-24 | Sumitomo Chemical Company, Limited | Hétéropolyacides, leur production et emploi |
Cited By (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5958224A (en) * | 1998-08-14 | 1999-09-28 | Exxon Research And Engineering Co | Process for deep desulfurization using combined hydrotreating-oxidation |
| GB2366803A (en) * | 2000-08-14 | 2002-03-20 | Ici Plc | Sulphur removal from a hydrocarbon stream |
| WO2002026916A1 (fr) * | 2000-09-28 | 2002-04-04 | Sulphco. Inc. | Desulfuration oxydante de combustibles fossiles par ultrasons |
| US6402939B1 (en) * | 2000-09-28 | 2002-06-11 | Sulphco, Inc. | Oxidative desulfurization of fossil fuels with ultrasound |
| ES2179753A1 (es) * | 2000-10-11 | 2003-01-16 | Univ Valencia Politecnica | Proceso y catalizadores para la eliminacion de compuestos de azufre de la fraccion gasolina. |
| WO2002031086A1 (fr) * | 2000-10-11 | 2002-04-18 | Consejo Superior De Investigaciones Cientificas | Procede et catalyseurs d'elimination des composes de soufre de la fraction essence |
| US6846406B2 (en) | 2000-10-11 | 2005-01-25 | Consejo Superior De Investigaciones Cientificas | Process and catalysts for eliminating sulphur compounds from the gasoline fraction |
| JP2004526012A (ja) * | 2001-02-08 | 2004-08-26 | ビーピー・コーポレーション・ノース・アメリカ・インコーポレーテッド | 輸送機関用燃料の製油所ブレンド成分の調製 |
| US6881325B2 (en) | 2001-02-08 | 2005-04-19 | Bp Corporation North America Inc. | Preparation of components for transportation fuels |
| WO2002062925A3 (fr) * | 2001-02-08 | 2003-11-20 | Bp Corp North America Inc | Preparation integree de composants de melange destinee a des carburants de transport de raffinerie |
| US6673230B2 (en) | 2001-02-08 | 2004-01-06 | Bp Corporation North America Inc. | Process for oxygenation of components for refinery blending of transportation fuels |
| WO2002097006A3 (fr) * | 2001-02-08 | 2003-10-16 | Bp Corp North America Inc | Procede d'oxygenation de composants conçus pour le melange de raffinerie de carburants de transport |
| WO2002062926A3 (fr) * | 2001-02-08 | 2002-12-12 | Bp Corporationnorth America In | Preparation de composes pour melange de raffinerie de carburants de transport |
| WO2002062927A3 (fr) * | 2001-02-08 | 2002-11-14 | Bp Corp North America Inc | Preparation de composants pour carburants de transport |
| US6872231B2 (en) | 2001-02-08 | 2005-03-29 | Bp Corporation North America Inc. | Transportation fuels |
| US7081196B2 (en) | 2001-05-10 | 2006-07-25 | Mark Cullen | Treatment of crude oil fractions, fossil fuels, and products thereof with sonic energy |
| US7871512B2 (en) | 2001-05-10 | 2011-01-18 | Petrosonics, Llc | Treatment of crude oil fractions, fossil fuels, and products thereof |
| WO2004055135A1 (fr) * | 2002-12-17 | 2004-07-01 | Shell Internationale Research Maatschappij B.V. | Processus d'oxydation selective catalytique de composes de soufre |
| EA007581B1 (ru) * | 2002-12-17 | 2006-12-29 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ каталитического селективного окисления сернистых соединений |
| US8409426B2 (en) | 2003-05-08 | 2013-04-02 | Petrosonics, Llc | Treatment of crude oil fractions, fossil fuels, and products thereof |
| US8663459B2 (en) | 2006-03-03 | 2014-03-04 | Saudi Arabian Oil Company | Catalytic process for deep oxidative desulfurization of liquid transportation fuels |
| CN101063044B (zh) * | 2006-04-27 | 2010-06-23 | 中国石油化工股份有限公司 | 一种柴油氧化脱硫方法 |
| US8926825B2 (en) | 2010-03-19 | 2015-01-06 | Mark Cullen | Process for removing sulfur from hydrocarbon streams using hydrotreatment, fractionation and oxidation |
| WO2013052102A1 (fr) * | 2011-10-03 | 2013-04-11 | Alternative Petroleum Technologies Sa | Catalyseurs d'oxydation issus d'hétéropolyacides et de composés azotés quaternisés, procédés de synthèse et d'activation de ces catalyseurs et procédés pour leur utilisation |
| EP2745931A1 (fr) | 2012-12-18 | 2014-06-25 | IFP Energies nouvelles | Catalyseur d'hydrotraitement dé résidus d'hydrocarbures comprenant dû vanadium et son utilisation dans un procédé d'hydroconversion dé residus |
| WO2017144460A1 (fr) * | 2016-02-26 | 2017-08-31 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Procédé pour la désulfuration par oxydation de carburants liquides |
| WO2022040320A1 (fr) * | 2020-08-19 | 2022-02-24 | Santa Fe Resources Development, Inc. | Procédés et systèmes de réduction de soufre |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2054070A1 (fr) | 1992-04-26 |
| GB9023257D0 (en) | 1990-12-05 |
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