JP2014522900A5 - - Google Patents
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- JP2014522900A5 JP2014522900A5 JP2014520194A JP2014520194A JP2014522900A5 JP 2014522900 A5 JP2014522900 A5 JP 2014522900A5 JP 2014520194 A JP2014520194 A JP 2014520194A JP 2014520194 A JP2014520194 A JP 2014520194A JP 2014522900 A5 JP2014522900 A5 JP 2014522900A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbon
- electron donor
- sulfone
- sulfoxide
- eluate
- 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.)
- Granted
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- 150000002430 hydrocarbons Chemical class 0.000 claims description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 150000003457 sulfones Chemical class 0.000 claims description 8
- 150000003462 sulfoxides Chemical class 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000001590 oxidative Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 238000006894 reductive elimination reaction Methods 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 150000003464 sulfur compounds Chemical class 0.000 claims description 2
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 238000000354 decomposition reaction Methods 0.000 claims 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 239000000741 silica gel Substances 0.000 claims 2
- 229910002027 silica gel Inorganic materials 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L Mercury(I) chloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims 1
- 239000003463 adsorbent Substances 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 229910052570 clay Inorganic materials 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 239000010779 crude oil Substances 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000003079 shale oil Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 239000000341 volatile oil Substances 0.000 claims 1
Description
本発明のプロセスは、炭化水素原料をスルホン及びスルホキシドの除去によって改良する方法であって、
ａ．炭化水素原料を酸化反応器に供給する工程であって、炭化水素原料が硫黄含有化合物を含む、工程；
ｂ．前記炭化水素原料を、酸化反応器内で、炭化水素原料中に存在する硫黄化合物を選択的に酸化するのに十分な条件下、触媒の存在下で酸化剤と接触させて、炭化水素及び酸化硫黄含有化合物を含む炭化水素の流れを生成する工程；
ｃ．前記酸化硫黄含有炭化水素の流れを水相及び非水性酸化溶出液に分離する工程；
ｄ．前記非水性酸化溶出液を回収し、それを電子供与剤と接触させて、非水性酸化溶出液中に存在するスルホン及びスルホキシドを減少させ、スルホン及びスルホキシド中の炭素−硫黄結合の還元的開裂を引き起こして分解し、副生成物の塩と脱硫された炭化水素を生成する工程；及び、
ｅ．副生成物の塩を分離し、脱硫された炭化水素の流れを回収する工程；を含む方法である。
The process of the present invention is a method of improving hydrocarbon feedstock by removal of sulfone and sulfoxide,
a. Supplying a hydrocarbon feed to the oxidation reactor, wherein the hydrocarbon feed contains a sulfur-containing compound;
b. The hydrocarbon feed is contacted with an oxidant in the presence of a catalyst under conditions sufficient to selectively oxidize sulfur compounds present in the hydrocarbon feed in an oxidation reactor to produce hydrocarbon and oxidation. Producing a hydrocarbon stream comprising sulfur-containing compounds;
c. Separating the sulfur oxide-containing hydrocarbon stream into an aqueous phase and a non-aqueous oxidizing eluate;
d. The non-aqueous oxidized eluate is recovered and contacted with an electron donor to reduce the sulfone and sulfoxide present in the non-aqueous oxidized eluate , and the reductive cleavage of the carbon-sulfur bond in the sulfone and sulfoxide. Causing and decomposing to produce by-product salts and desulfurized hydrocarbons ; and
e. The method comprising; a salt by-product was isolated, recovering the flow of desulfurized hydrocarbons.
Claims (20)
ａ．炭化水素原料を酸化反応器に供給する工程であって、前記炭化水素原料が硫黄含有化合物を含む工程；
ｂ．前記炭化水素原料を、酸化反応器内で、炭化水素原料中に存在する硫黄化合物を選択的に酸化するのに十分な条件下、触媒の存在下で酸化剤と接触させて、炭化水素及び酸化硫黄含有化合物を含む炭化水素の流れを生成する工程；
ｃ．前記酸化硫黄含有炭化水素の流れを水相及び非水性酸化溶出液に分離する工程；
ｄ．前記非水性酸化溶出液を回収し、それを電子供与剤と接触させて、非水性酸化溶出液中に存在するスルホン及びスルホキシドを減少させ、スルホン及びスルホキシド中の炭素−硫黄結合の還元的開裂を引き起こして分解し、副生成物の塩と脱硫された炭化水素を生成する工程；
ｅ．副生成物の塩を分離し、脱硫された炭化水素の流れを回収する工程；を含む
ことを特徴とする方法。 A method for improving a hydrocarbon feedstock by removing sulfone and sulfoxide from the hydrocarbon feedstock, comprising:
a. Supplying a hydrocarbon feed to the oxidation reactor, wherein the hydrocarbon feed contains a sulfur-containing compound;
b. The hydrocarbon feed is contacted with an oxidant in the presence of a catalyst under conditions sufficient to selectively oxidize sulfur compounds present in the hydrocarbon feed in an oxidation reactor to produce hydrocarbon and oxidation. Producing a hydrocarbon stream comprising sulfur-containing compounds;
c. Separating the sulfur oxide-containing hydrocarbon stream into an aqueous phase and a non-aqueous oxidizing eluate;
d. The non-aqueous oxidized eluate is recovered and contacted with an electron donor to reduce the sulfone and sulfoxide present in the non-aqueous oxidized eluate , and the reductive cleavage of the carbon-sulfur bond in the sulfone and sulfoxide. Causing and decomposing to produce by-product salts and desulfurized hydrocarbons ;
e. Method characterized by including: a salt by-product was isolated, recovering the flow of desulfurized hydrocarbons.
請求項１に記載の方法。 The process according to claim 1, wherein from about 1 to about 5 molar equivalents of an electron donor are used, based on the raw sulfone and sulfoxide content.
請求項２に記載の方法。 The method of claim 2, wherein about 1 to about 3 molar equivalents of an electron donor are used.
請求項１に記載の方法。 The method of claim 1, wherein the decomposition is performed at a temperature of about 100 to about 300C.
請求項４に記載の方法。 The method of claim 4, wherein the decomposition is performed at about 100 to about 200 ° C.
請求項５に記載の方法。 The method of claim 5, wherein the decomposition is carried out at about 100 to about 150 ° C.
請求項１に記載の方法。 The method of claim 1, wherein the decomposition is performed at a pressure of about 3 to about 30 kg / cm 2.
請求項１に記載の方法。 The method of claim 1, wherein the decomposition is performed at about 0.05 to about 4.0 h−1.
請求項１に記載の方法。 The method of claim 1, wherein the electron donor has an oxidation potential sufficient to effect reductive cleavage of the sulfone and sulfoxide.
請求項９に記載の方法。 The method according to claim 9, wherein the electron donor is a tetraazaalkene.
請求項１０に記載の方法。 Tetraazaalkene is bisimidazolylidene
The method of claim 10 .
請求項１に記載の方法。 The method according to claim 1, wherein the hydrocarbon feedstock is crude oil, oil, shale oil, coal liquid, intermediate essential oil product, and a distillation fraction thereof.
請求項９に記載の方法。 The method of claim 9, wherein the electron donor has a half potential of at least -1.2V in dimethylformamide when referenced to a saturated calomel electrode.
請求項１２に記載の方法。 The method of claim 12, wherein the hydrocarbon feedstock boils in the range of about 36 to about 2000 ° C.
請求項１に記載の方法。 The method according to claim 1, wherein after step c, the non-aqueous oxidation eluate is subjected to a solvent extraction treatment.
請求項１５に記載の方法。 The method of claim 15, wherein the solvent is a polar solvent.
請求項１５に記載の方法。 The process according to claim 15, wherein the extraction is carried out at about 20 to about 60 ° C and a pressure of about 1 to about 10 bar.
請求項１５に記載の方法。 The method according to claim 15, wherein after the extraction step, the extracted eluate is subjected to an adsorption treatment.
請求項１８に記載の方法。 The method according to claim 18, wherein the adsorbent is selected from the group consisting of activated carbon, silica gel, alumina, natural clay, silica gel coated with a polar polymer, activated carbon and alumina.
請求項１８に記載の方法。
The method of claim 18, wherein the adsorption zone is operated at about 20 to about 60 ° C and a pressure of about 1 to about 15 bar.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/181,043 US20130015104A1 (en) | 2011-07-12 | 2011-07-12 | Process for sulfone conversion by super electron donors |
| US13/181,043 | 2011-07-12 | ||
| PCT/US2012/043118 WO2013009440A1 (en) | 2011-07-12 | 2012-06-19 | Process for sulfone conversion by super electron donors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014522900A JP2014522900A (en) | 2014-09-08 |
| JP2014522900A5 true JP2014522900A5 (en) | 2015-07-09 |
| JP6046713B2 JP6046713B2 (en) | 2016-12-21 |
Family
ID=46420551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014520194A Expired - Fee Related JP6046713B2 (en) | 2011-07-12 | 2012-06-19 | Process of sulfone conversion with superelectron donors |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20130015104A1 (en) |
| EP (1) | EP2732009B1 (en) |
| JP (1) | JP6046713B2 (en) |
| KR (1) | KR101926217B1 (en) |
| CN (1) | CN103930525B (en) |
| WO (1) | WO2013009440A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008262567B2 (en) | 2007-05-03 | 2013-05-16 | Auterra, Inc. | Product containing monomer and polymers of titanyls and methods for making same |
| US8298404B2 (en) | 2010-09-22 | 2012-10-30 | Auterra, Inc. | Reaction system and products therefrom |
| US8894843B2 (en) | 2008-03-26 | 2014-11-25 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| US8764973B2 (en) | 2008-03-26 | 2014-07-01 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| US9061273B2 (en) | 2008-03-26 | 2015-06-23 | Auterra, Inc. | Sulfoxidation catalysts and methods and systems of using same |
| US9206359B2 (en) | 2008-03-26 | 2015-12-08 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| US9828557B2 (en) | 2010-09-22 | 2017-11-28 | Auterra, Inc. | Reaction system, methods and products therefrom |
| KR102109707B1 (en) | 2012-09-28 | 2020-05-12 | 사우디 아라비안 오일 컴퍼니 | Process for Reducing the Sulfur Content from Oxidized Sulfur-Containing Hydrocarbons |
| WO2016154529A1 (en) | 2015-03-26 | 2016-09-29 | Auterra, Inc. | Adsorbents and methods of use |
| US10450516B2 (en) | 2016-03-08 | 2019-10-22 | Auterra, Inc. | Catalytic caustic desulfonylation |
| KR101897339B1 (en) * | 2016-09-06 | 2018-09-11 | 현대자동차주식회사 | Avilable driving distance estimation method for electric vehicle and the system thereof |
| RU2711550C1 (en) * | 2019-08-30 | 2020-01-17 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | Method of producing a concentrate of sulphoxides and sulphons of oil origin |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6602260A (en) * | 1965-02-23 | 1966-08-24 | ||
| US6087544A (en) | 1998-05-07 | 2000-07-11 | Exxon Research And Engineering Co. | Process for the production of high lubricity low sulfur distillate fuels |
| US6277271B1 (en) | 1998-07-15 | 2001-08-21 | Uop Llc | Process for the desulfurization of a hydrocarbonaceoous oil |
| US6368495B1 (en) | 1999-06-07 | 2002-04-09 | Uop Llc | Removal of sulfur-containing compounds from liquid hydrocarbon streams |
| US6174178B1 (en) | 2000-03-14 | 2001-01-16 | Tektronix, Inc. | Retractable connector mechanism for signal connectors |
| US6402940B1 (en) | 2000-09-01 | 2002-06-11 | Unipure Corporation | Process for removing low amounts of organic sulfur from hydrocarbon fuels |
| US20030094400A1 (en) | 2001-08-10 | 2003-05-22 | Levy Robert Edward | Hydrodesulfurization of oxidized sulfur compounds in liquid hydrocarbons |
| MXPA04005711A (en) | 2001-12-13 | 2005-06-20 | Univ Lehigh | Oxidative desulfurization of sulfur-containing hydrocarbons. |
| JP2003268385A (en) * | 2002-03-20 | 2003-09-25 | National Institute Of Advanced Industrial & Technology | Method for oxidative desulfurizing sulfur compounds contained in fuel oil |
| JP2004019445A (en) * | 2002-06-12 | 2004-01-22 | Hitachi Industries Co Ltd | Screw compressor and operation control method thereof |
| US7314545B2 (en) * | 2004-01-09 | 2008-01-01 | Lyondell Chemical Technology, L.P. | Desulfurization process |
| CA2589399A1 (en) | 2004-12-29 | 2006-07-06 | Bp Corporation North America Inc. | Oxidative desulfurization process |
| EP2001802B1 (en) * | 2006-03-03 | 2021-06-09 | Saudi Arabian Oil Company | Catalytic process for deep oxidative desulfurization of liquid transportation fuels |
| US7790021B2 (en) * | 2007-09-07 | 2010-09-07 | Uop Llc | Removal of sulfur-containing compounds from liquid hydrocarbon streams |
| EP2496538B1 (en) * | 2009-11-07 | 2020-02-19 | Saudi Arabian Oil Company | Hydrocarbon recovery from sulfones formed by oxidative desulfurization process |
-
2011
- 2011-07-12 US US13/181,043 patent/US20130015104A1/en not_active Abandoned
-
2012
- 2012-06-19 CN CN201280041312.6A patent/CN103930525B/en not_active Expired - Fee Related
- 2012-06-19 WO PCT/US2012/043118 patent/WO2013009440A1/en active Application Filing
- 2012-06-19 JP JP2014520194A patent/JP6046713B2/en not_active Expired - Fee Related
- 2012-06-19 EP EP12731252.8A patent/EP2732009B1/en not_active Not-in-force
- 2012-06-19 KR KR1020147003570A patent/KR101926217B1/en active IP Right Grant
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