JP6348905B2 - 酸化された硫黄含有炭化水素の硫黄含量の低減方法 - Google Patents
酸化された硫黄含有炭化水素の硫黄含量の低減方法Info
- Publication number
- JP6348905B2 JP6348905B2 JP2015534788A JP2015534788A JP6348905B2 JP 6348905 B2 JP6348905 B2 JP 6348905B2 JP 2015534788 A JP2015534788 A JP 2015534788A JP 2015534788 A JP2015534788 A JP 2015534788A JP 6348905 B2 JP6348905 B2 JP 6348905B2
- Authority
- JP
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- Prior art keywords
- sulfur
- hydrocarbon
- mixture
- oxidized
- hydrocarbon compound
- 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 - Fee Related
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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
- C10G32/00—Refining of hydrocarbon oils by electric or magnetic means, by irradiation, or by using microorganisms
- C10G32/02—Refining of hydrocarbon oils by electric or magnetic means, by irradiation, or by using microorganisms by electric or magnetic means
-
- 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
-
- 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
- C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
- C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
- C10G53/14—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one oxidation step
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
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)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Electrodes For Compound Or Non-Metal Manufacture (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Description
500ppmwの元素硫黄、0.28重量%の有機硫黄を含有し、0.85kg/Lの密度を有する水素化処理した直留ディーゼルを、下記反応条件下、酸化的脱硫に付した。酸化剤(過酸化水素)と硫黄とのモル比4:1、酸化触媒Mo(IV)、反応時間30分、反応温度80℃、反応圧力1kg/cm2。
10 酸化的脱硫ゾーン
12 炭化水素原料油
14 酸化剤
16 酸化触媒
18 酸化された硫黄含有炭化水素
20 抽出装置
22 流れ
26 脱硫炭化水素生成物
34 酸化された硫黄含有炭化水素と電解質溶液とを含有する流れ
36 電解質溶液
40 電気化学反応ゾーン
42 陽極
44 陰極
52 脱硫炭化水素生成物
54 電解質溶液と硫黄副生物との混合物
60 分離ゾーン
62 水
108 システム
110 酸化的脱硫ゾーン
112 炭化水素原料油
114 酸化剤
116 水相均質系酸化触媒
118 非水性油相
120 抽出ゾーン
122 スルホンとスルホキシドとの流れ
126 脱硫炭化水素生成物
130 分離ゾーン
132 脱硫炭化水素、酸化された硫黄含有炭化水素化合物および水相を含有する混合物
134 水相
136 電解質溶液
140 電気化学反応ゾーン
146 脱硫流出物
152 回収脱硫炭化水素流
154 電解質と硫黄副生成物とを含む水/塩流れ
160 分離ゾーン
162 水流
172 追加された抽出溶媒
174 再循環された抽出溶媒
Claims (18)
- 炭化水素原料油の脱硫方法であって、
a.硫黄含有炭化水素化合物を含んでなる炭化水素原料油を酸化反応器に供給する工程;
b.炭化水素原料油中に存在する硫黄含有炭化水素化合物を選択的に酸化するのに十分な条件下、酸化反応器において触媒の存在下で炭化水素原料油を酸化剤と接触させ、炭化水素化合物と酸化された硫黄含有炭化水素化合物との混合物を生成する工程;
c.有効量の電解質溶液の存在下、電気化学反応器において酸化反応器からの炭化水素化合物と酸化された硫黄含有炭化水素化合物との混合物を電気化学的に反応させる工程であって、電気化学反応は、酸化された硫黄含有炭化水素化合物の少なくとも一部の硫黄不含有炭化水素と硫黄副生物との混合物への分解を促進するのに有効な電位で行われる工程;および
d.硫黄不含有炭化水素を回収する工程
を含む方法。 - さらに、炭化水素化合物と酸化された硫黄含有炭化水素化合物との混合物から酸化された硫黄含有炭化水素化合物を抽出し、酸化反応の工程から得た第1の混合物から硫黄不含有炭化水素を回収し、ついで、酸化された硫黄含有炭化水素化合物を電気化学反応器に通すことを含む、請求項1に記載の方法。
- 酸化された硫黄含有炭化水素化合物はスルホンおよび/またはスルホキシドを含む、請求項1または2に記載の方法。
- 炭化水素原料油はディーゼル原料油流である、請求項1または2に記載の方法。
- 硫黄不含有炭化水素と硫黄副生物との生成混合物を、硫黄不含有炭化水素と硫黄副生物とに分離することを更に含む、請求項1または2に記載の方法。
- 硫黄不含有炭化水素と硫黄副生物との生成混合物は電解質を更に含有しており、電解質は硫黄副生物と一緒に排出される、請求項5に記載の方法。
- 電気化学反応は20℃〜350℃の温度で行われる、請求項1または2に記載の方法。
- 電気化学反応は3kg/cm2〜30kg/cm2の圧力で行われる、請求項1または2に記載の方法。
- 電気化学反応は0.05h−1〜4.0h−1の液体時空間速度で行われる、請求項1または2に記載の方法。
- 電気化学反応器の全セル電位が、Ag/AgCl参照電極に対して測定して1.0〜2.5Vである、請求項1または2に記載の方法。
- 電気化学反応器は、白金、ステンレス鋼およびグラファイトからなる群から選択される材料から形成された陰極、および白金、ステンレス鋼、ニッケルおよびグラファイトからなる群から選択される材料から形成された陽極を含んでなる、請求項10に記載の方法。
- 電解質溶液は有機溶媒中に電解質塩を含んだものである、請求項1または2に記載の方法。
- 有機溶媒は、エチレンカーボネート、プロピレンカーボネート、ニトロベンゼン、ベンゾニトリル、N−ホルミルモルホリン、スルホラン、および前記溶媒の少なくとも1つを含む混合物からなる群から選択される、請求項12に記載の方法。
- 電解質塩はテトラアルキルアンモニウム塩である、請求項12に記載の方法。
- テトラアルキルアンモニウム塩は、過塩素酸テトラエチルアンモニウム、過塩素酸テトラブチルアンモニウム、テトラエチルアンモニウムテトラフルオロボレート、テトラブチルアンモニウムテトラフルオロボレート、テトラエチルアンモニウムヘキサフルオロホスフェート、テトラブチルアンモニウムヘキサフルオロホスフェート、テトラエチルアンモニウムパラトルエンスルホネート、テトラブチルアンモニウムクロリド、テトラブチルアンモニウムブロミド、および前記塩の少なくとも1つを含む混合物からなる群から選択される、請求項14に記載の方法。
- テトラアルキルアンモニウム塩は、少なくとも0.05モルの濃度で有機溶媒中に存在する、請求項14に記載の方法。
- テトラアルキルアンモニウム塩は、少なくとも0.1モルの濃度で有機溶媒中に存在する、請求項14に記載の方法。
- テトラアルキルアンモニウム塩は、少なくとも0.5モルの濃度で有機溶媒中に存在する、請求項14に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261707561P | 2012-09-28 | 2012-09-28 | |
US61/707,561 | 2012-09-28 | ||
PCT/US2013/062558 WO2014052951A1 (en) | 2012-09-28 | 2013-09-30 | Process for reducing the sulfur content from oxidized sulfur-containing hydrocarbons |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2015535890A JP2015535890A (ja) | 2015-12-17 |
JP2015535890A5 JP2015535890A5 (ja) | 2016-08-04 |
JP6348905B2 true JP6348905B2 (ja) | 2018-06-27 |
Family
ID=49378556
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015534788A Expired - Fee Related JP6348905B2 (ja) | 2012-09-28 | 2013-09-30 | 酸化された硫黄含有炭化水素の硫黄含量の低減方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10011782B2 (ja) |
EP (1) | EP2900794A1 (ja) |
JP (1) | JP6348905B2 (ja) |
KR (1) | KR102109707B1 (ja) |
CN (1) | CN104822804B (ja) |
SA (1) | SA515360202B1 (ja) |
WO (1) | WO2014052951A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103933846B (zh) * | 2014-04-14 | 2016-03-23 | 苏州鼎德电环保科技有限公司 | 烟气脱硫脱硝的方法 |
CA3050326C (en) * | 2017-02-10 | 2023-08-29 | Haldor Topsoe A/S | A method for the hydroprocessing of renewable feeds |
KR102398989B1 (ko) | 2020-04-01 | 2022-05-18 | 한국기초과학지원연구원 | 탄화수소 유분으로부터 황화합물을 제거하는 방법 |
Family Cites Families (22)
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US4404069A (en) * | 1982-03-17 | 1983-09-13 | Monsanto Company | Electrolytic desulfurization of anilino sulfur compounds |
AU2414897A (en) * | 1996-03-26 | 1997-10-17 | Catalytic Sciences, Ltd. | Process for removal of organo-sulfur compounds from liquid hydrocarbons |
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 |
US6171478B1 (en) | 1998-07-15 | 2001-01-09 | Uop Llc | Process for the desulfurization of a hydrocarbonaceous oil |
US6368495B1 (en) | 1999-06-07 | 2002-04-09 | Uop Llc | Removal of sulfur-containing compounds from liquid hydrocarbon streams |
US6338788B1 (en) * | 1999-06-11 | 2002-01-15 | Exxonmobil Research And Engineering Company | Electrochemical oxidation of sulfur compounds in naphtha |
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 |
WO2003051798A1 (en) | 2001-12-13 | 2003-06-26 | Lehigh University | Oxidative desulfurization of sulfur-containing hydrocarbons |
CN1202209C (zh) * | 2003-01-17 | 2005-05-18 | 石油大学(北京) | 一种石油油品脱硫方法 |
NZ555486A (en) | 2004-12-29 | 2010-03-26 | Bp Corp North America Inc | Preparation of hydrocarbons through a liquid phase oxidative desulphurisation process utilising a solid titanium catalyst |
US7744749B2 (en) * | 2005-09-08 | 2010-06-29 | Saudi Arabian Oil Company | Diesel oil desulfurization by oxidation and extraction |
WO2007103440A2 (en) | 2006-03-03 | 2007-09-13 | Saudi Arabian Oil Company | Catalytic process for deep oxidative desulfurization of liquid transportation fuels |
US8557101B2 (en) * | 2007-12-20 | 2013-10-15 | Exxonmobil Research And Engineering Company | Electrochemical treatment of heavy oil streams followed by caustic extraction |
WO2011056941A1 (en) | 2009-11-07 | 2011-05-12 | Saudi Arabian Oil Company | Hydrocarbon recovery from sulfones formed by oxidative desulfurization process |
US8404106B2 (en) * | 2009-12-18 | 2013-03-26 | Exxonmobil Research And Engineering Company | Regeneration of alkali metal reagent |
US9574143B2 (en) | 2010-09-07 | 2017-02-21 | Saudi Arabian Oil Company | Desulfurization and sulfone removal using a coker |
US9598647B2 (en) | 2010-09-07 | 2017-03-21 | Saudi Arabian Oil Company | Process for oxidative desulfurization and sulfone disposal using solvent deasphalting |
US9574142B2 (en) | 2010-09-07 | 2017-02-21 | Saudi Arabian Oil Company | Process for oxidative desulfurization and sulfone management by gasification |
US9574144B2 (en) | 2010-09-07 | 2017-02-21 | Saudi Arabian Oil Company | Process for oxidative desulfurization and denitrogenation using a fluid catalytic cracking (FCC) unit |
US20130015104A1 (en) | 2011-07-12 | 2013-01-17 | Adnan Al-Hajji | Process for sulfone conversion by super electron donors |
-
2013
- 2013-09-30 CN CN201380062339.8A patent/CN104822804B/zh not_active Expired - Fee Related
- 2013-09-30 US US14/041,046 patent/US10011782B2/en active Active
- 2013-09-30 WO PCT/US2013/062558 patent/WO2014052951A1/en active Application Filing
- 2013-09-30 EP EP13777195.2A patent/EP2900794A1/en not_active Withdrawn
- 2013-09-30 JP JP2015534788A patent/JP6348905B2/ja not_active Expired - Fee Related
- 2013-09-30 KR KR1020157010958A patent/KR102109707B1/ko active IP Right Grant
-
2015
- 2015-03-28 SA SA515360202A patent/SA515360202B1/ar unknown
Also Published As
Publication number | Publication date |
---|---|
KR20150068965A (ko) | 2015-06-22 |
SA515360202B1 (ar) | 2018-06-11 |
JP2015535890A (ja) | 2015-12-17 |
EP2900794A1 (en) | 2015-08-05 |
KR102109707B1 (ko) | 2020-05-12 |
US10011782B2 (en) | 2018-07-03 |
US20140090985A1 (en) | 2014-04-03 |
WO2014052951A1 (en) | 2014-04-03 |
CN104822804B (zh) | 2018-10-26 |
CN104822804A (zh) | 2015-08-05 |
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