JP5270070B2 - 硫黄含有化合物をより高い沸点の化合物に転化することによってガソリンを脱硫する新規な方法 - Google Patents
硫黄含有化合物をより高い沸点の化合物に転化することによってガソリンを脱硫する新規な方法 Download PDFInfo
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- JP5270070B2 JP5270070B2 JP2006115101A JP2006115101A JP5270070B2 JP 5270070 B2 JP5270070 B2 JP 5270070B2 JP 2006115101 A JP2006115101 A JP 2006115101A JP 2006115101 A JP2006115101 A JP 2006115101A JP 5270070 B2 JP5270070 B2 JP 5270070B2
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- sulfur
- resin
- gasoline
- containing compound
- desulfurizing
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 54
- 229910052717 sulfur Inorganic materials 0.000 title claims description 54
- 239000011593 sulfur Substances 0.000 title claims description 54
- 150000001875 compounds Chemical class 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 52
- 238000009835 boiling Methods 0.000 title claims description 25
- 230000003009 desulfurizing effect Effects 0.000 title claims description 12
- 239000011347 resin Substances 0.000 claims description 58
- 229920005989 resin Polymers 0.000 claims description 58
- 239000003054 catalyst Substances 0.000 claims description 33
- 150000001336 alkenes Chemical class 0.000 claims description 32
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 18
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 16
- 229930192474 thiophene Natural products 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 238000007259 addition reaction Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000011148 porous material Substances 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000004523 catalytic cracking Methods 0.000 description 7
- -1 thiophene unsaturated sulfur Chemical class 0.000 description 7
- 238000006477 desulfuration reaction Methods 0.000 description 6
- 230000023556 desulfurization Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004231 fluid catalytic cracking Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
- ZQRGREQWCRSUCI-UHFFFAOYSA-N [S].C=1C=CSC=1 Chemical class [S].C=1C=CSC=1 ZQRGREQWCRSUCI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000006326 desulfonation Effects 0.000 description 1
- 238000005869 desulfonation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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
- C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
- C10G47/02—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used
-
- 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
- C10G17/00—Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge
- C10G17/095—Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge with "solid acids", e.g. phosphoric acid deposited on a carrier
-
- 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
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/02—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material
- C10G25/03—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material with crystalline alumino-silicates, e.g. molecular sieves
- C10G25/05—Removal of non-hydrocarbon compounds, e.g. sulfur compounds
Description
・触媒上への重合体およびオリゴマーの沈着;
・温度の影響下での触媒の脱スルホン化;
・原料油中に存在する窒素含有化合物を含む塩基性化合物による酸点の中和。
・適切な反応器において、処理されるべき原料油を樹脂と接触させ、原料油中に含まれるオレフィンと硫黄含有化合物との付加反応により高い沸点の硫黄含有化合物を生じさせる、第一の工程(A);
・原料油に対して硫黄含有量が低減させられた軽質のフラクションと、硫黄含有化合物が濃縮された重質のフラクションを生じさせ得るように、第一工程からの混合物を分留する工程(B)。
a)樹脂中に存在するスルホン基からの硫黄の量が、好ましくは15重量%超、より好ましくは18〜22重量である;
b)この適用のための樹脂の比表面積が、好ましくは55m2/g未満、より好ましくは25〜50m2/gである;
c)樹脂の細孔容積が、好ましくは0.10〜0.50ml/g、より好ましくは0.15〜0.40ml/g、より一層好ましくは0.16〜0.25ml/gである;
d)平均細孔径が、好ましくは10〜40nm、より好ましくは20〜30nm、より一層好ましくは20〜28nmである;
e)樹脂が、好ましくは0.3〜1mm、より好ましくは0.6〜0.85mmの粒度分布を有するビーズ状に成形される。
この実施例では、3種の市販の樹脂が比較された。第一のものは、従来技術の樹脂であり、第二のものは、本発明によるものであり、第三のものも本発明によるが、第二のものより酸点の濃度は高く、比表面積は低かった。
樹脂1、2および3の活性は、通過床式反応器(traversed bed reactor)を用いて行われた試験の間に評価された。
樹脂(1)および(3)の安定性が、約400時間の2つの試験の間で比較された。各試験のために、60mlの樹脂が反応器内に装填された。圧力および流量は、それぞれ2MPaおよび50ml/hに等しくなるように一定に維持された。
Claims (9)
- オレフィンおよび硫黄含有化合物を含有するガソリンフラクションを脱硫する方法であって、
前記ガソリンフラクションを酸性の樹脂タイプの触媒に接触させて、前記ガソリンフラクションのオレフィンと硫黄含有化合物との間の付加反応によってより高い沸点の硫黄含有化合物を生じさせ、前記付加反応により生じたより高い沸点の硫黄含有化合物を含む生成物を生じさせる第一工程(A)と、
第一工程から生じた前記より高い沸点の硫黄含有化合物を含む生成物を分留して、原料油に対して硫黄含有量が低減させられた軽質のフラクションと、硫黄含有化合物が濃縮されたより高い沸点のフラクションを生じさせる工程(B)と
を少なくとも包含し、工程(A)において用いられた樹脂タイプの触媒の酸容量は4.7当量/kg超であり、その比表面積は55m2/g未満であり、その細孔容積は0.16〜0.25ml/gである方法。 - 用いられた樹脂タイプの触媒の酸容量は、5.0当量/kg超であり、その比表面積は、50m2/g以下である、請求項1に記載のオレフィンおよび硫黄含有化合物を含有するガソリンフラクションを脱硫する方法。
- チオフェンの転化度は、99%未満である、請求項1または2に記載のオレフィンおよび硫黄含有化合物を含有するガソリンフラクションを脱硫する方法。
- 操作温度が50〜150℃であり、操作圧力が0.5MPa超である、請求項1〜3のいずれか1つに記載のガソリンフラクションを脱硫する方法。
- 毎時空間速度(hourly space velocity:HSV)が、0.2〜5h−1である、請求項1〜4のいずれか1つに記載の方法。
- 処理されるべき原料油が50ppm超の窒素を含有しており、前記原料油は、使用済み樹脂タイプの触媒を用いる、窒素含有化合物を抽出するための装置内で前処理され、前記樹脂タイプの触媒は、前記第一工程(A)において前記ガソリンフラクションのオレフィンと硫黄含有化合物との間の付加反応のために用いられたものと同一である、請求項1〜5のいずれか1つに記載のガソリンフラクションを脱硫する方法。
- 前記樹脂タイプの触媒は、並列で機能する複数の固定床間に分配され、触媒粒子の径は、0.3〜1mmである、請求項1〜6のいずれか1つに記載のガソリンフラクションを脱硫する方法。
- 前記樹脂タイプの触媒は、直列で機能する複数の固定床間に分配され、熱交換器が各反応器の間に入れられる、請求項1〜6のいずれか1つに記載のガソリンフラクションを脱硫する方法。
- 前記樹脂タイプの触媒は、沸騰床様式で用いられる、請求項1〜6のいずれか1つに記載のガソリンフラクションを脱硫する方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0503981 | 2005-04-19 | ||
FR0503981A FR2884521B1 (fr) | 2005-04-19 | 2005-04-19 | Nouveau procede de desulfuration des essences par alourdissement des composes soufres |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2006299263A JP2006299263A (ja) | 2006-11-02 |
JP2006299263A5 JP2006299263A5 (ja) | 2009-06-04 |
JP5270070B2 true JP5270070B2 (ja) | 2013-08-21 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2006115101A Expired - Fee Related JP5270070B2 (ja) | 2005-04-19 | 2006-04-19 | 硫黄含有化合物をより高い沸点の化合物に転化することによってガソリンを脱硫する新規な方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7504022B2 (ja) |
EP (1) | EP1715026B1 (ja) |
JP (1) | JP5270070B2 (ja) |
KR (1) | KR101286805B1 (ja) |
BR (1) | BRPI0601297A (ja) |
FR (1) | FR2884521B1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011135206A1 (fr) * | 2010-04-28 | 2011-11-03 | IFP Energies Nouvelles | Procede d'oligomerisation des olefines utilisant au moins un catalyseur organique possedant une forte densite de sites acides |
CN116396139B (zh) * | 2023-06-08 | 2023-08-18 | 新疆天利石化股份有限公司 | 一种于固定床反应器中催化脱除苯乙烯中噻吩类芳香杂环含硫化合物的方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5863419A (en) * | 1997-01-14 | 1999-01-26 | Amoco Corporation | Sulfur removal by catalytic distillation |
US6048451A (en) * | 1997-01-14 | 2000-04-11 | Bp Amoco Corporation | Sulfur removal process |
US6059962A (en) * | 1998-09-09 | 2000-05-09 | Bp Amoco Corporation | Multiple stage sulfur removal process |
US6352640B1 (en) * | 2000-04-18 | 2002-03-05 | Exxonmobil Research And Engineering Company | Caustic extraction of mercaptans (LAW966) |
FR2821852B1 (fr) | 2001-03-12 | 2003-05-02 | Inst Francais Du Petrole | Procede de production d'une essence desulfuree a partir d'une coupe essence contenant de l'essence de conversion |
FR2835530B1 (fr) * | 2002-02-07 | 2004-04-09 | Inst Francais Du Petrole | Procede integre de desulfuration d'un effluent de craquage ou de vapocraquage d'hydrocarbures |
FR2840620B1 (fr) | 2002-06-07 | 2004-07-30 | Inst Francais Du Petrole | Procede de production d'hydrocarbures a faible teneur en soufre et en azote |
JP2005068126A (ja) * | 2003-08-20 | 2005-03-17 | Rohm & Haas Co | 芳香族アルキル化反応に使用するための方法、系および触媒 |
FR2890077B1 (fr) * | 2005-08-26 | 2012-03-23 | Inst Francais Du Petrole | Procede de desulfuration d'essences olefiniques par alourdissement des composes soufres avec regeneration du catalyseur |
-
2005
- 2005-04-19 FR FR0503981A patent/FR2884521B1/fr not_active Expired - Fee Related
-
2006
- 2006-03-03 EP EP06290373.7A patent/EP1715026B1/fr active Active
- 2006-04-18 KR KR1020060035033A patent/KR101286805B1/ko active IP Right Grant
- 2006-04-18 US US11/405,676 patent/US7504022B2/en active Active
- 2006-04-19 BR BRPI0601297-3A patent/BRPI0601297A/pt not_active Application Discontinuation
- 2006-04-19 JP JP2006115101A patent/JP5270070B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US7504022B2 (en) | 2009-03-17 |
JP2006299263A (ja) | 2006-11-02 |
EP1715026A1 (fr) | 2006-10-25 |
EP1715026B1 (fr) | 2023-10-11 |
FR2884521B1 (fr) | 2009-08-21 |
US20070023324A1 (en) | 2007-02-01 |
KR20060110226A (ko) | 2006-10-24 |
BRPI0601297A (pt) | 2007-05-15 |
KR101286805B1 (ko) | 2013-07-17 |
FR2884521A1 (fr) | 2006-10-20 |
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