CA2730707C - Purification of dialkyl sulfides with basic metal alcoholates and/or alkali or alkaline earth metals - Google Patents
Purification of dialkyl sulfides with basic metal alcoholates and/or alkali or alkaline earth metals Download PDFInfo
- Publication number
- CA2730707C CA2730707C CA2730707A CA2730707A CA2730707C CA 2730707 C CA2730707 C CA 2730707C CA 2730707 A CA2730707 A CA 2730707A CA 2730707 A CA2730707 A CA 2730707A CA 2730707 C CA2730707 C CA 2730707C
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- Canada
- Prior art keywords
- metal
- dialkyl
- sulfide
- alkali
- alkaline earth
- Prior art date
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- 229910052784 alkaline earth metal Inorganic materials 0.000 title claims abstract description 49
- 150000003568 thioethers Chemical class 0.000 title claims abstract description 36
- 150000001342 alkaline earth metals Chemical class 0.000 title claims abstract description 28
- 239000003513 alkali Substances 0.000 title claims abstract description 21
- 238000000746 purification Methods 0.000 title description 9
- 229910052728 basic metal Inorganic materials 0.000 title description 2
- 150000003818 basic metals Chemical class 0.000 title description 2
- 229910052751 metal Inorganic materials 0.000 claims abstract description 70
- 239000002184 metal Substances 0.000 claims abstract description 70
- -1 sulfide borane complexes Chemical class 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 58
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 49
- 230000008569 process Effects 0.000 claims abstract description 44
- 239000002585 base Substances 0.000 claims abstract description 28
- 125000005210 alkyl ammonium group Chemical group 0.000 claims abstract description 16
- 230000009467 reduction Effects 0.000 claims abstract description 15
- 239000012039 electrophile Substances 0.000 claims abstract description 13
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 8
- 150000001408 amides Chemical class 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 8
- 229910052987 metal hydride Inorganic materials 0.000 claims abstract description 8
- 150000004681 metal hydrides Chemical class 0.000 claims abstract description 8
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 8
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 8
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 7
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical group CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 174
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 150000001340 alkali metals Chemical class 0.000 claims description 12
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- 229910000085 borane Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- ROSSIHMZZJOVOU-UHFFFAOYSA-N 2-(methylthio)propane Chemical compound CSC(C)C ROSSIHMZZJOVOU-UHFFFAOYSA-N 0.000 claims description 4
- 229910000799 K alloy Inorganic materials 0.000 claims description 4
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
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- WXEHBUMAEPOYKP-UHFFFAOYSA-N methylsulfanylethane Chemical compound CCSC WXEHBUMAEPOYKP-UHFFFAOYSA-N 0.000 claims description 2
- VMKAFJQFKBASMU-UHFFFAOYSA-N 1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole Chemical compound C12CCCN2B(C)OC1(C=1C=CC=CC=1)C1=CC=CC=C1 VMKAFJQFKBASMU-UHFFFAOYSA-N 0.000 claims 1
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- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 21
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000012411 boiled sweets Nutrition 0.000 description 3
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- KKQJUNDZGUCWKN-GOSISDBHSA-N (2r)-2-[1,3,2-dioxaborolan-2-yloxy(diphenyl)methyl]pyrrolidine Chemical compound C1CCN[C@H]1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OB1OCCO1 KKQJUNDZGUCWKN-GOSISDBHSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- IOPLHGOSNCJOOO-UHFFFAOYSA-N methyl 3,4-diaminobenzoate Chemical group COC(=O)C1=CC=C(N)C(N)=C1 IOPLHGOSNCJOOO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- COCAUCFPFHUGAA-MGNBDDOMSA-N n-[3-[(1s,7s)-5-amino-4-thia-6-azabicyclo[5.1.0]oct-5-en-7-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C=C(F)C([C@@]23N=C(SCC[C@@H]2C3)N)=CC=1NC(=O)C1=CC=C(Cl)C=N1 COCAUCFPFHUGAA-MGNBDDOMSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229940094035 potassium bromide Drugs 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N sulfure de di n-propyle Natural products CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8086808P | 2008-07-15 | 2008-07-15 | |
| US61/080868 | 2008-07-15 | ||
| PCT/EP2009/058848 WO2010007006A1 (en) | 2008-07-15 | 2009-07-10 | Process to purify dialkyl sulfides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2730707A1 CA2730707A1 (en) | 2010-01-21 |
| CA2730707C true CA2730707C (en) | 2016-09-13 |
Family
ID=41110509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2730707A Active CA2730707C (en) | 2008-07-15 | 2009-07-10 | Purification of dialkyl sulfides with basic metal alcoholates and/or alkali or alkaline earth metals |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8586796B2 (enExample) |
| EP (1) | EP2315743B1 (enExample) |
| JP (1) | JP5587310B2 (enExample) |
| KR (1) | KR101617055B1 (enExample) |
| CN (1) | CN102099332B (enExample) |
| CA (1) | CA2730707C (enExample) |
| DK (1) | DK2315743T3 (enExample) |
| ES (1) | ES2727702T3 (enExample) |
| RU (1) | RU2515986C2 (enExample) |
| SI (1) | SI2315743T1 (enExample) |
| WO (1) | WO2010007006A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2965562B1 (fr) * | 2010-09-30 | 2013-03-01 | Arkema France | Procede de preparation de disulfures de dialkyle |
| FR2994974B1 (fr) * | 2012-08-30 | 2015-05-01 | Arkema France | Distillation reactive des dso |
| CN107674026B (zh) * | 2017-11-03 | 2019-12-06 | 海化生命(厦门)科技有限公司 | 鲁索替尼中间体(3r)-3-(4-溴-1h-吡唑-1-基)-环戊烷基丙腈的制备方法 |
| CN107857728A (zh) * | 2017-11-20 | 2018-03-30 | 成都惟邦药业有限公司 | 一种利非司特中间体的合成方法 |
| US10774040B1 (en) | 2019-04-29 | 2020-09-15 | Chevron Phillips Chemical Company Lp | Processes for removing carbon disulfide from symmetrical and asymmetrical sulfide product streams |
| CN116283687A (zh) * | 2022-09-07 | 2023-06-23 | 金川集团股份有限公司 | 一种二异戊基硫醚的合成工艺 |
| US11945770B1 (en) * | 2023-03-06 | 2024-04-02 | Chevron Phillips Chemical Company Lp | Catalytic processes and systems for alkyl sulfide purification |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1681600A (en) * | 1925-07-21 | 1928-08-21 | Christiaan Van Loon | Process of preparing alkali-metal alcoholates of compounds containing alcoholic hydroxyl groups |
| JPS496287B1 (enExample) | 1968-01-26 | 1974-02-13 | ||
| US3835559A (en) | 1972-03-27 | 1974-09-17 | G Kotter | Machine for ironing trousers |
| US4173619A (en) * | 1978-03-14 | 1979-11-06 | Erickson Donald C | Combustion gas desulfurization |
| US4358297A (en) * | 1980-01-02 | 1982-11-09 | Exxon Research And Engineering Company | Removal of sulfur from process streams |
| AR230264A1 (es) * | 1980-11-26 | 1984-03-01 | Merz & Co Gmbh & Co | Procedimiento para la obtencion de compuestos de xantato |
| CA1244480A (en) * | 1981-10-05 | 1988-11-08 | Daniel A. Dimmig | Deodorization of dialkyl polysulfides |
| EP0189606B1 (en) * | 1985-02-01 | 1989-08-09 | European Atomic Energy Community (Euratom) | Process for selective adsorption of sulfur compounds from gaseous mixtures containing mercaptans |
| US4964957A (en) * | 1988-12-06 | 1990-10-23 | Phillips Petroleum Company | Purification of high boiling alkyl sulfides |
| US5480860A (en) * | 1988-12-23 | 1996-01-02 | Petrolite Corporation | Methods for reducing sulfides in sewage gas |
| US5382417A (en) * | 1990-01-03 | 1995-01-17 | Herr Haase, Inc. | Process for removal of selected component gases from multi-component gas streams |
| US5089246A (en) * | 1990-01-29 | 1992-02-18 | Atochem North America, Inc. | Process for converting carbon disulfide to hydrogen sulfide in hydrogen sulfide/carbon disulfide mixtures |
| US5157201A (en) * | 1990-06-22 | 1992-10-20 | Exxon Chemical Patents Inc. | Process for adsorbing sulfur species from propylene/propane using regenerable adsorbent |
| US5302771A (en) * | 1991-04-08 | 1994-04-12 | Exxon Chemical Patents, Inc. | Process for upgrading the quality of light ends |
| LU87923A1 (de) * | 1991-04-24 | 1992-11-16 | Euratom | Verfahren zum entfernen von schwefelwasserstoff und/oder schwefelkohlenstoff aus abgasen |
| FR2694197B1 (fr) * | 1992-07-30 | 1994-09-02 | Atochem Elf Sa | Désodorisant des effluents de papeterie à base d'ester d'acide undécylénique. |
| RU2152421C1 (ru) * | 1994-05-19 | 2000-07-10 | Мицуи Петрокемикал Индастриз Лтд. | СПОСОБ ОЧИСТКИ α-ОЛЕФИНОВ ДЛЯ ПОЛИМЕРИЗАЦИИ И СПОСОБ ПОЛУЧЕНИЯ ПОЛИ-α-ОЛЕФИНОВ |
| US5559271A (en) * | 1995-07-26 | 1996-09-24 | Phillips Petroleum Company | Organic polysulfide compositions having reduced odor |
| JP3567034B2 (ja) * | 1995-11-30 | 2004-09-15 | ジーイー東芝シリコーン株式会社 | アルコキシシランの精製方法 |
| US6136144A (en) * | 1996-06-06 | 2000-10-24 | Thermatrix, Inc. | Method of removing sulfur from a process gas stream using a packed bed calcinator |
| JPH11137964A (ja) * | 1997-11-06 | 1999-05-25 | Nec Corp | 悪臭物質の除去方法及び脱臭装置 |
| US6015536A (en) * | 1998-01-14 | 2000-01-18 | Ecolab Inc. | Peroxyacid compound use in odor reduction |
| AR014299A1 (es) * | 1998-01-14 | 2001-02-07 | Ecolab Inc | Un procedimiento para remover un olor de un efluente atmosférico, un tratamiento previo o un tratamiento posterior para remover un olor de un efluente atmosférico y efluente atmosférico obtenido con dicho procedimiento. |
| DE19828977A1 (de) | 1998-06-29 | 1999-12-30 | Basf Ag | Verfahren zur Entfernung saurer Gasbestandteile aus Gasen |
| FR2781795B1 (fr) * | 1998-07-31 | 2000-09-08 | Atochem Elf Sa | Compositions a base de dimethyldisulfure a odeur masquee |
| US6051739A (en) * | 1999-01-26 | 2000-04-18 | Phillips Petroleum Company | Process for producing organic polysulfides |
| JP2002020765A (ja) * | 2000-07-04 | 2002-01-23 | Idemitsu Petrochem Co Ltd | 炭化水素中の二硫化炭素の除去方法 |
| US6736879B2 (en) * | 2002-05-01 | 2004-05-18 | Chevron Phillips Chemical Company Lp | Process to prepare low carbon disulfide containing dimethyl sulfide |
| US7446077B2 (en) * | 2004-03-17 | 2008-11-04 | Intevep, S.A. | Selective sulfur removal from hydrocarbon streams by absorption |
| US20070123729A1 (en) * | 2005-11-29 | 2007-05-31 | Farnham William B | Synthesis of trithiocarbonates |
| KR20090024752A (ko) * | 2006-06-26 | 2009-03-09 | 바스프 에스이 | 보란 에테르 착물 |
-
2009
- 2009-07-10 SI SI200931970T patent/SI2315743T1/sl unknown
- 2009-07-10 WO PCT/EP2009/058848 patent/WO2010007006A1/en not_active Ceased
- 2009-07-10 JP JP2011517882A patent/JP5587310B2/ja not_active Expired - Fee Related
- 2009-07-10 RU RU2011105242/04A patent/RU2515986C2/ru active
- 2009-07-10 US US13/003,587 patent/US8586796B2/en active Active
- 2009-07-10 DK DK09780449.6T patent/DK2315743T3/da active
- 2009-07-10 ES ES09780449T patent/ES2727702T3/es active Active
- 2009-07-10 KR KR1020117003304A patent/KR101617055B1/ko not_active Expired - Fee Related
- 2009-07-10 CN CN200980127616.2A patent/CN102099332B/zh not_active Expired - Fee Related
- 2009-07-10 CA CA2730707A patent/CA2730707C/en active Active
- 2009-07-10 EP EP09780449.6A patent/EP2315743B1/en active Active
-
2013
- 2013-10-18 US US14/057,109 patent/US9073831B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CA2730707A1 (en) | 2010-01-21 |
| KR20110031974A (ko) | 2011-03-29 |
| SI2315743T1 (sl) | 2019-08-30 |
| WO2010007006A1 (en) | 2010-01-21 |
| US9073831B2 (en) | 2015-07-07 |
| KR101617055B1 (ko) | 2016-04-29 |
| US20140051891A1 (en) | 2014-02-20 |
| JP5587310B2 (ja) | 2014-09-10 |
| JP2011528011A (ja) | 2011-11-10 |
| RU2011105242A (ru) | 2012-08-20 |
| CN102099332B (zh) | 2014-02-12 |
| DK2315743T3 (da) | 2019-06-03 |
| RU2515986C2 (ru) | 2014-05-20 |
| CN102099332A (zh) | 2011-06-15 |
| ES2727702T3 (es) | 2019-10-18 |
| US20110124920A1 (en) | 2011-05-26 |
| EP2315743A1 (en) | 2011-05-04 |
| US8586796B2 (en) | 2013-11-19 |
| EP2315743B1 (en) | 2019-05-08 |
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