JP2008528252A - 水素化処理触媒、その製造方法、およびその使用 - Google Patents
水素化処理触媒、その製造方法、およびその使用 Download PDFInfo
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- JP2008528252A JP2008528252A JP2007551706A JP2007551706A JP2008528252A JP 2008528252 A JP2008528252 A JP 2008528252A JP 2007551706 A JP2007551706 A JP 2007551706A JP 2007551706 A JP2007551706 A JP 2007551706A JP 2008528252 A JP2008528252 A JP 2008528252A
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
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- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0209—Esters of carboxylic or carbonic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/94—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the iron group metals or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
- B01J38/50—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids
- B01J38/52—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids oxygen-containing
-
- 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
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- 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
- C10G45/06—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used containing nickel or cobalt metal, or compounds thereof
- C10G45/08—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used containing nickel or cobalt metal, or compounds thereof in combination with chromium, molybdenum, or tungsten metals, or compounds thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
- B01J23/882—Molybdenum and cobalt
Abstract
(式中、各R1が、独立して、C1−18アルキル基、C2−18アルケニル基、C6−18アリール基、C3−8シクロアルキル基、C7−20アルキルアリールまたはアリールアルキル基を表すか、または2個のR1基が一緒にC2−182価基を形成し、R2が、C1−18アルキレン基、C6−18アリーレン基、C3−7シクロアルキレン基、またはそれらの組合せを表す)を有する少なくとも一種の有機化合物も含んでなることを特徴とする。本発明は、そのような触媒の製造方法、および該触媒の水素化処理または水素化分解への使用にも関する。
Description
の、少なくとも2個のカルボン酸エステル官能基を含んでなる少なくとも一種の有機化合物も含んでなることを特徴とする、水素化処理触媒である。
の、少なくとも一種の有機化合物と接触させることを含んでなる。
この例では、本発明の触媒の製造方法を説明し、次いでこれらの触媒を例IIIで使用する。
この例では、本発明の触媒を溶剤の非存在下で製造する方法を説明する。次いでこの触媒を例IIIで使用する。
触媒BおよびC(本発明による)のそれぞれを、触媒Aの製造業者により推奨される手順に従い、ジメチルジスルフィド(DMDS)2重量%を加えたディーゼル油で硫化する。
原料タイプ 30%LCO−70%ディーゼル油
混合物
硫黄(ppm) 9074
15℃における密度(g/ml) 0.8863
モノ芳香族化合物(重量%) 20.7
ジ芳香族化合物(重量%) 21.3
トリ芳香族化合物(重量%) 3.8
Σ芳香族化合物(重量%) 45.8
窒素(ppm) 389
ASTM標準D86による
蒸留(℃)
初期点 180
5体積% 224
50体積% 291
95体積% 360
終点 361
触媒 A B C
HDS T HDS T HDS −7℃ T HDS −7℃
触媒 A B C
T HDN における残留N(ppm) 120 78 60
Claims (17)
- 少なくとも一種の耐火性酸化物を基材とする担体、少なくとも一種の元素周期律表のVIII族金属および少なくとも一種の元素周期律表のVIB族金属を含んでなる、水素化処理触媒であって、該水素化処理触媒が、式(I)または(II):
の、少なくとも2個のカルボン酸エステル官能基を含んでなる少なくとも一種の有機化合物も含んでなる、水素化処理触媒。 - 前記式(I)または(II)の有機化合物が、アルキルオルト−フタレート、アルキルイソフタレート、アルキルテレフタレート、マロン酸エステル、アジピン酸エステル、グルタル酸エステル、1,6−ジオキサシクロデカン−2,5−ジオン、ジメチル2−(メトキシメチル)−スクシネート、ジブチルイタコネート、ジエチル2,3−ジアセチルスクシネート、ジメチルシクロヘキサン−1,4−ジカルボキシレート、ジメチル3,3’−ジチオジプロピオネート、グリセロールトリアセテート、プロピレングリコールジアセテート、エチレングリコールジメタクリレートおよびペンタエリトリトールテトラキス(3−メルカプトプロピオネート)から選択され、前記式(I)または(II)の有機化合物が、好ましくはジエステルである、請求項1に記載の触媒。
- 前記式(I)および(II)の2個の基>C=Oを分離している炭素原子の数が、1、2または4、好ましくは1または2である、請求項1または2に記載の触媒。
- 前記式(I)の有機化合物がC1〜C4ジアルキルスクシネート、好ましくはジメチルスクシネートである、請求項3に記載の触媒。
- VIBおよびVIII族の金属1モルあたり、少なくとも0.001モルの、少なくとも一種の有機化合物を含む、請求項1〜4のいずれか一項に記載の触媒。
- VIBおよびVIII族の金属1モルあたり、0.001〜10モルの、少なくとも一種の有機化合物を含む、請求項5に記載の触媒。
- 請求項1〜6のいずれか一項に記載の水素化処理触媒の製造方法であって、少なくとも一種の耐火性酸化物を基材とする担体、少なくとも一種の酸化物状態にあるVIII族金属および少なくとも一種の酸化物状態にあるVIB族金属を含んでなる触媒を、式(I)または(II):
の、少なくとも一種の有機化合物と接触させることを含んでなる、方法。 - 前記少なくとも一種の耐火性酸化物を基材とする担体、少なくとも一種の酸化物状態にあるVIII族金属および少なくとも一種の酸化物状態にあるVIB族金属を含んでなる触媒が、再生された触媒である、請求項7に記載の製造方法。
- 前記接触に続いて、少なくとも一つの、一般的に温度0〜100℃における熟成工程を行い、前記熟成工程の持続時間が数分間〜数年間であり、所望により前記熟成工程に続いて、少なくとも一つの熱処理工程を温度50℃〜250℃で、数分間〜数日間行う、請求項7または8に記載の製造方法。
- 前記触媒が前記式(I)または(II)の化合物と、少なくとも一種の溶剤および/または少なくとも一種の酸の存在下で接触する、請求項7〜9のいずれか一項に記載の製造方法。
- 前記式(I)または(II)の有機化合物が、使用する前記溶剤に少なくとも部分的に可溶である、請求項10に記載の製造方法。
- 前記溶剤が、水、トルエン、キシレン、エチレングリコール、ジエチレングリコール、トリエチレングリコール、グリセロール、エタノール、tert−ブタノール、最も一般的には分子量が118(トリエチレングリコール)〜1000の、ポリエチレングリコール(PEG)、ホワイトスピリット、および石油エーテルから選択される、請求項10または11に記載の製造方法。
- 前記触媒が前記式(I)または(II)の化合物と、他の場所で、水素化処理反応器の外側で接触する、請求項7〜12のいずれか一項に記載の製造方法。
- 前記触媒が前記式(I)または(II)の化合物と、水素の存在下で、および好ましくは硫化水素、元素状硫黄、CS2、メルカプタン、スルフィドおよび/またはポリスルフィド、および硫黄化合物を含む沸点が400℃未満の炭化水素留分から選択された少なくとも一種の硫化剤の存在下で、一般的に水素化処理反応器中で接触する、請求項7〜13のいずれか一項に記載の製造方法。
- 請求項1〜6のいずれか一項に記載の水素化処理触媒を、その場で、または他の場所で、活性化する方法であって、前記触媒を、水素の存在下に、および好ましくは硫化水素、元素状硫黄、CS2、メルカプタン、スルフィドおよび/またはポリスルフィド、および硫黄化合物を含む沸点が400℃未満の炭化水素留分から選択された少なくとも一種の硫化剤の存在下に配置する、方法。
- 前記硫化剤がジメチルジスルフィドである、請求項15に記載の方法。
- 請求項15または16に記載の方法により活性化された前記水素化処理触媒の、炭化水素、特に沸点が40〜560℃である石油留分に由来する炭化水素、の水素化処理および/または水素化分解のための使用。
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FR0500579A FR2880823B1 (fr) | 2005-01-20 | 2005-01-20 | Catalyseur d'hydrotraitement, son procede de preparation et et son utilisation |
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PCT/FR2006/000126 WO2006077326A1 (fr) | 2005-01-20 | 2006-01-19 | Catalyseur d’hydrotraitement, son procede de preparation et son utilisation |
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JP2013514169A (ja) * | 2009-12-16 | 2013-04-25 | イエフペ エネルジ ヌヴェル | 第viii族および第vib族金属を含み、酢酸およびc1−c4ジアルキルスクシナートを有する、水素化処理において使用可能な触媒および調製 |
JP2014514142A (ja) * | 2011-03-18 | 2014-06-19 | イエフペ エネルジ ヌヴェル | 第viii族および第vib族からの金属を含む、水素化処理における使用のための触媒、並びに、クエン酸およびコハク酸c1−c4ジアルキルによる調製 |
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JP2021528245A (ja) * | 2018-06-27 | 2021-10-21 | イエフペ エネルジ ヌヴェルIfp Energies Nouvelles | 乳酸アルキルを添加された触媒、その調製および水素化処理および/または水素化分解の方法におけるその使用 |
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KR101603327B1 (ko) * | 2008-06-18 | 2016-03-14 | 에스케이이노베이션 주식회사 | 원유의 산도 저감용 환원제 및 이를 이용한 원유의 산도저감 방법 |
FR2936961B1 (fr) * | 2008-10-10 | 2011-05-06 | Eurecat Sa | Procede de regeneration de catalyseurs de traitement d'hydrocarbures. |
US9254478B2 (en) | 2009-08-24 | 2016-02-09 | Albemarle Corporation | Solutions and catalysts comprising group VI metal, group VIII metal, phosphorus and an additive |
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JP2010089087A (ja) * | 2008-10-10 | 2010-04-22 | Eurecat Sa | 炭化水素を処理するための触媒を再生する方法 |
JP2013514169A (ja) * | 2009-12-16 | 2013-04-25 | イエフペ エネルジ ヌヴェル | 第viii族および第vib族金属を含み、酢酸およびc1−c4ジアルキルスクシナートを有する、水素化処理において使用可能な触媒および調製 |
JP2014514142A (ja) * | 2011-03-18 | 2014-06-19 | イエフペ エネルジ ヌヴェル | 第viii族および第vib族からの金属を含む、水素化処理における使用のための触媒、並びに、クエン酸およびコハク酸c1−c4ジアルキルによる調製 |
CN108463433A (zh) * | 2015-10-27 | 2018-08-28 | 麻省理工学院 | 用于气体分离的电化学方法 |
CN108463433B (zh) * | 2015-10-27 | 2022-04-26 | 麻省理工学院 | 用于气体分离的电化学方法 |
JP2021504102A (ja) * | 2017-11-22 | 2021-02-15 | イエフペ エネルジ ヌヴェルIfp Energies Nouvelles | フラン化合物を含有している触媒および水素化処理および/または水素化分解の方法におけるその使用 |
JP7291699B2 (ja) | 2017-11-22 | 2023-06-15 | イエフペ エネルジ ヌヴェル | フラン化合物を含有している触媒および水素化処理および/または水素化分解の方法におけるその使用 |
JP2021528245A (ja) * | 2018-06-27 | 2021-10-21 | イエフペ エネルジ ヌヴェルIfp Energies Nouvelles | 乳酸アルキルを添加された触媒、その調製および水素化処理および/または水素化分解の方法におけるその使用 |
JP7394080B2 (ja) | 2018-06-27 | 2023-12-07 | イエフペ エネルジ ヌヴェル | 乳酸アルキルを添加された触媒、その調製および水素化処理および/または水素化分解の方法におけるその使用 |
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AU2006207388A1 (en) | 2006-07-27 |
CN101107071A (zh) | 2008-01-16 |
EP1838438B1 (fr) | 2014-12-10 |
CA2595335A1 (fr) | 2006-07-27 |
JP5184096B2 (ja) | 2013-04-17 |
DK1838438T3 (en) | 2015-02-23 |
ZA200705951B (en) | 2009-02-25 |
WO2006077326A1 (fr) | 2006-07-27 |
KR101259135B1 (ko) | 2013-04-30 |
AU2006207388B2 (en) | 2010-09-30 |
EP1838438A1 (fr) | 2007-10-03 |
CN101107071B (zh) | 2011-05-18 |
CA2595335C (fr) | 2013-01-08 |
US9821302B2 (en) | 2017-11-21 |
US9212324B2 (en) | 2015-12-15 |
FR2880823A1 (fr) | 2006-07-21 |
US20160008799A1 (en) | 2016-01-14 |
KR20070111491A (ko) | 2007-11-21 |
FR2880823B1 (fr) | 2008-02-22 |
US20080194892A1 (en) | 2008-08-14 |
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