WO2002038701A1 - Procede d'hydrotraitement d'un melange de composes hydrocarbones, riche en olefines et en composes aromatiques - Google Patents
Procede d'hydrotraitement d'un melange de composes hydrocarbones, riche en olefines et en composes aromatiques Download PDFInfo
- Publication number
- WO2002038701A1 WO2002038701A1 PCT/EP2001/012989 EP0112989W WO0238701A1 WO 2002038701 A1 WO2002038701 A1 WO 2002038701A1 EP 0112989 W EP0112989 W EP 0112989W WO 0238701 A1 WO0238701 A1 WO 0238701A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compounds
- chosen
- ammonia
- catalyst
- hydrotreatment
- Prior art date
Links
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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
-
- 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
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1037—Hydrocarbon fractions
- C10G2300/104—Light gasoline having a boiling range of about 20 - 100 °C
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1037—Hydrocarbon fractions
- C10G2300/1044—Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4018—Spatial velocity, e.g. LHSV, WHSV
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4081—Recycling aspects
-
- 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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/02—Gasoline
Definitions
- the present invention relates to a process for hydrotreating a mixture of hydrocarbon compounds comprising from four to eight carbon atoms, rich in olefins and in monoaromatic compounds. It relates more particularly to the hydrotreatment of cuts resulting from the distillation of crude oils, steam cracking, catalytic reforming, catalytic cracking, coking or any process producing such cuts and the cuts resulting from the treatment of coal such as gasolines of coal.
- the refiner is confronted with a double constraint, linked on the one hand to the injection of the liquid into a high pressure gas flow (technological constraints of design of the charge pump and design of safety systems to avoid in particular the return of hydrogen in the event of the pump stopping) and on the other hand to its dispersion by means of an appropriate diffuser taking into account the pressures used in the process.
- the present application therefore relates to a process which requires neither pretreatment of the catalyst, nor of introduction of gaseous or liquid nitrogen compounds in the hydrogenation gas. It relates to a simple process which can be easily implemented whatever the hydrotreatment unit, without requiring investments in too expensive material, with an inexpensive catalyst compared to catalysts containing noble metals such as platinum and palladium, which can adapt to fillers whose composition can vary in concentration of olefins and monoaromatic compounds and which allows good desulfurization of the charge.
- olefins is meant here the monoolefinic and diolefinic compounds generally present in the feeds sent for hydrotreatment.
- the present invention therefore relates to a process for hydrotreating a mixture of hydrocarbon compounds from C4 to C8, rich in olefins and in monoaromatic compounds, by hydrogenation in the presence of a solid catalyst characterized in that a precursor is introduced ammonia in the feed of hydrocarbon compounds and that the catalyst comprises at least one transition metal supported on at least one refractory oxide.
- transition metal is understood to mean any transition metal with the exception of the so-called noble metals, in particular platinum and palladium.
- One of the advantages of the process is linked to the introduction of an ammonia precursor into the feed which makes it possible during the reaction to release gaseous ammonia which is present during the selective hydrogenation reaction of the olefins and which can be recovered and recycled with unused hydrogen.
- this process makes it possible to precisely control the quantity of ammonia released during the hydrotreatment reaction.
- it makes it possible to limit the undesired oligomerization reactions while maintaining excellent catalyst activity for the desired reactions of selective hydrogenation of olefins and desulfurization of the feed.
- the Applicant has found that on the one hand, the oligomerization of aromatic compounds results from the presence of acid sites on the catalyst, these sites being of variable acid forces.
- the efficiency of the hydrotreatment reaction depends on the electrodeficiency of the catalytic support which itself is correlated with its acidity.
- At most 1000 ppm by weight of molar nitrogen equivalent of ammonia precursor is injected into the feed.
- 5 to 1000 ppm by weight of nitrogen molar equivalent of nitrogen precursor will be injected, and preferably from 10 to 200 ppm.
- the ammonia precursors are chosen from nitrogen compounds capable of releasing gaseous ammonia under the conditions of the hydrotreatment. These ammonia precursors must decompose before their arrival on the catalyst so as to release the ammonia as close as possible to the catalyst and for this to have a decomposition temperature lower than the reaction temperature in the reactor.
- the decomposition temperature of the ammonia precursors is less than 300 ° C, and preferably less than 180 ° C.
- the ammonia precursor is chosen from linear and branched amines, polyamines, imines, and urea and its derivatives.
- the amines and polyamines are chosen from the group consisting of mono, di and trialkylamines comprising from 1 to 10 carbon atoms per alkyl group, the alkyl groups being linear or cyclic, and the polyalkylamines comprising from 1 to 5 nitrogen atoms , each alkyl group comprising from 1 to 6 carbon atoms in linear or branched form.
- the preferred amines and polyamines are chosen from methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, cyclohexylamine, cycloheptylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, trimethylamine, triethylamine, tripropylamine, tributylamine, methylenediamine, ethylenediamine, propylenediamine, butylenediamine, dimethylenetriamine, diethylenetriamine, dipropylenetriamine, triethylenetetramine, tripropylenetetramine, tetraethylenepentamine and tetrapropylenepentamine, cyclohexylamine, triethylamine and ethylenediamine being preferred.
- the catalyst necessary for the process according to the invention consists of at least one metal chosen from the group consisting of nickel, cobalt, molybdenum, vanadium and tungsten; nickel alone and the nickel / molybdenum, cobalt / molybdenum and nickel / tungsten combinations are preferred.
- This or these metals are supported on at least one refractory oxide chosen from alumina, silica, silicoalumines, aluminophosphates, zirconia, magnesia and oxides of titanium, rutile and anatase, these oxides being in amorphous form or crystalline.
- the operation is carried out at a temperature between 50 and 400 ° C., under a pressure between 10 6 Pa and 10 7 Pa, preferably between 3 ⁇ 10 6 Pa and 6 ⁇ 10 6 Pa, and a hvv varying from 0.5 to 10h "1 .
- the excess ammonia gas formed can be recycled into the hydrogen-rich recycle gas. This has the advantage of limiting the quantity of ammonia precursor injected into the feed.
- This hydrotreatment process is particularly suitable for the hydrotreatment of petroleum C6 refining cuts, in particular C 6 cuts from reforming and catalytic gasolines from catalytic cracking.
- the present example describes the conditions under which the invention is carried out by presenting the gain brought by the introduction of ammonia precursor in an industrial feed to be hydrotreated, and this for different ammonia precursors and for different concentrations thereof.
- the feed to be hydrotreated is a mixture at 21% by weight of a C6 reforming cut and 79% by weight of a C6 cut of pyrolysis gasoline. It contains :
- the benzene content was measured in application of the UOP 744-86 method referenced in the "Laboratory test methods for petroleum and its products", published by UOP Process Division, (UOP Inc. 20 UOP Plaza- Algonquin Mt Prospect Roads-Des Plains-Illinois 60016).
- the olefin content is determined by measuring the number of bromine in application of standard ASTM D1159, and the sulfur content by method ASTM D2622.
- ammonia precursors were used on a hydrotreatment pilot unit for 100 ml of catalyst, at a temperature of 200 ° C., a pressure of 26.5 ⁇ 10 5 Pa, operating with an H2 / hydrocarbon ratio of 230NI / I, hvv of the charge being 1.6h "1 .
- the present example aims to emphasize the efficiency of the process whatever the relative concentrations of the load of olefins and of monoaromatic compounds.
- cyclohexylamine or CHA is used as the ammonia precursor.
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)
- Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002542022A JP4900885B2 (ja) | 2000-11-07 | 2001-11-06 | オレフィンと芳香族化合物が豊富な炭化水素化合物混合物の水素化処理方法 |
AU2002219087A AU2002219087A1 (en) | 2000-11-07 | 2001-11-06 | Method for hydrotreatment of a mixture of hydrocarbon compounds, rich in olefinsand aromatic compounds |
KR1020037006246A KR100591577B1 (ko) | 2000-11-07 | 2001-11-06 | 올레핀 및 방향족 화합물이 농후한 탄화수소계 화합물의 혼합물의 수소화처리 방법 |
US10/416,058 US7399402B2 (en) | 2000-11-07 | 2001-11-06 | Method for hydrotreatment of a mixture of hydrocarbon compounds, rich in olefins and aromatic compounds |
AT01993659T ATE509997T1 (de) | 2000-11-07 | 2001-11-06 | Verfahren zur hydrobehandlung eines olefine und aromaten enthaltenden kohlenwasserstoffgemisches |
EP01993659A EP1334167B1 (fr) | 2000-11-07 | 2001-11-06 | Procede d'hydrotraitement d'un melange de composes hydrocarbones, riche en olefines et en composes aromatiques |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00203887A EP1205531A1 (fr) | 2000-11-07 | 2000-11-07 | Procédé d'hydrotraitement d'un mélange de composés hydrocarbones, riche en oléfines et en composés aromatiques |
EP00203887.5 | 2000-11-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002038701A1 true WO2002038701A1 (fr) | 2002-05-16 |
Family
ID=8172230
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2001/012989 WO2002038701A1 (fr) | 2000-11-07 | 2001-11-06 | Procede d'hydrotraitement d'un melange de composes hydrocarbones, riche en olefines et en composes aromatiques |
Country Status (8)
Country | Link |
---|---|
US (1) | US7399402B2 (fr) |
EP (2) | EP1205531A1 (fr) |
JP (1) | JP4900885B2 (fr) |
KR (1) | KR100591577B1 (fr) |
AT (1) | ATE509997T1 (fr) |
AU (1) | AU2002219087A1 (fr) |
ES (1) | ES2363494T3 (fr) |
WO (1) | WO2002038701A1 (fr) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10150556A1 (de) * | 2001-10-15 | 2003-04-17 | Basf Ag | Verfahren zur katalytischen Hydrierung |
FR2918066B1 (fr) | 2007-06-26 | 2010-11-19 | Total France | Liant concentre non gelifiable et pompable pour bitume/polymere |
FR2929616B1 (fr) * | 2008-04-08 | 2011-09-09 | Total France | Procede de reticulation de compositions bitume/polymere presentant des emissions reduites d'hydrogene sulfure |
CN103068772B (zh) * | 2010-06-23 | 2016-04-06 | 道达尔研究技术弗吕公司 | 醇在受抑制的酸性催化剂上的脱水 |
EP3164466A1 (fr) * | 2014-07-01 | 2017-05-10 | Anellotech, Inc. | Procédés pour la conversion de biomasse en btx à faible teneur en soufre, en azote et en oléfines par l'intermédiaire d'un procédé de pyrolyse catalytique rapide |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3859204A (en) * | 1974-01-22 | 1975-01-07 | Gulf Research Development Co | Residual oil hydrodesulfurization process by catalyst pretreatment and ammonia addition |
FR2376100A1 (fr) * | 1976-12-28 | 1978-07-28 | Engelhard Min & Chem | Procede pour augmenter la selectivite d'hydrogenation d'un catalyseur et application a l'hydrogenation, notamment pour la production de cumene |
US4112007A (en) * | 1975-05-23 | 1978-09-05 | Anic S.P.A. | Selective hydrogenation in gaseous phase of cyclopentadiene or a mixture of ethylene and acetylene using a palladium zinc catalyst deactivated with ammonia, ammonium chloride, steam, or their mixtures |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE639951A (fr) * | 1962-11-16 |
-
2000
- 2000-11-07 EP EP00203887A patent/EP1205531A1/fr not_active Withdrawn
-
2001
- 2001-11-06 AU AU2002219087A patent/AU2002219087A1/en not_active Abandoned
- 2001-11-06 JP JP2002542022A patent/JP4900885B2/ja not_active Expired - Fee Related
- 2001-11-06 WO PCT/EP2001/012989 patent/WO2002038701A1/fr active IP Right Grant
- 2001-11-06 ES ES01993659T patent/ES2363494T3/es not_active Expired - Lifetime
- 2001-11-06 AT AT01993659T patent/ATE509997T1/de not_active IP Right Cessation
- 2001-11-06 EP EP01993659A patent/EP1334167B1/fr not_active Expired - Lifetime
- 2001-11-06 US US10/416,058 patent/US7399402B2/en not_active Expired - Fee Related
- 2001-11-06 KR KR1020037006246A patent/KR100591577B1/ko not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3859204A (en) * | 1974-01-22 | 1975-01-07 | Gulf Research Development Co | Residual oil hydrodesulfurization process by catalyst pretreatment and ammonia addition |
US4112007A (en) * | 1975-05-23 | 1978-09-05 | Anic S.P.A. | Selective hydrogenation in gaseous phase of cyclopentadiene or a mixture of ethylene and acetylene using a palladium zinc catalyst deactivated with ammonia, ammonium chloride, steam, or their mixtures |
FR2376100A1 (fr) * | 1976-12-28 | 1978-07-28 | Engelhard Min & Chem | Procede pour augmenter la selectivite d'hydrogenation d'un catalyseur et application a l'hydrogenation, notamment pour la production de cumene |
Also Published As
Publication number | Publication date |
---|---|
JP4900885B2 (ja) | 2012-03-21 |
EP1334167B1 (fr) | 2011-05-18 |
EP1205531A1 (fr) | 2002-05-15 |
EP1334167A1 (fr) | 2003-08-13 |
US20040045873A1 (en) | 2004-03-11 |
KR20030066654A (ko) | 2003-08-09 |
US7399402B2 (en) | 2008-07-15 |
KR100591577B1 (ko) | 2006-06-20 |
AU2002219087A1 (en) | 2002-05-21 |
JP2004518775A (ja) | 2004-06-24 |
ES2363494T3 (es) | 2011-08-05 |
ATE509997T1 (de) | 2011-06-15 |
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