EP1217060A1 - Procédé de traitement d'hydrocarbures C4 comportant du butadiène et des composés acétyléniques comprenant des étapes de distillation et d'hydrogénation sélective - Google Patents
Procédé de traitement d'hydrocarbures C4 comportant du butadiène et des composés acétyléniques comprenant des étapes de distillation et d'hydrogénation sélective Download PDFInfo
- Publication number
- EP1217060A1 EP1217060A1 EP01403076A EP01403076A EP1217060A1 EP 1217060 A1 EP1217060 A1 EP 1217060A1 EP 01403076 A EP01403076 A EP 01403076A EP 01403076 A EP01403076 A EP 01403076A EP 1217060 A1 EP1217060 A1 EP 1217060A1
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- European Patent Office
- Prior art keywords
- zone
- hydrogenation
- distillation
- column
- butadiene
- 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.)
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 43
- 238000004821 distillation Methods 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 23
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- -1 diene compounds Chemical class 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052737 gold Inorganic materials 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 238000004230 steam cracking Methods 0.000 claims description 3
- 238000011144 upstream manufacturing Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 239000012530 fluid Substances 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 description 9
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 8
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- QMMOXUPEWRXHJS-HWKANZROSA-N (e)-pent-2-ene Chemical compound CC\C=C\C QMMOXUPEWRXHJS-HWKANZROSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 235000021183 entrée Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
Definitions
- the invention relates to a method for treating a charge comprising hydrocarbons with at least 4 carbon atoms per molecule, strongly unsaturated. It applies in particular to the purification of an olefinic cut containing mostly butadiene, including 1,3 butadiene, produced highly recoverable as a raw material for elastomers.
- This cut also contains acetylenic impurities, vinyl acetylene (VAC), ethylacetylene (ETAC), generally 1 to 2% which create dysfunctions in the polymerization processes due to the presence gums that these compounds tend to create and which therefore must be eliminated.
- VAC vinyl acetylene
- EMC ethylacetylene
- the hydrogenation reactor can be installed upstream of the debutanization. Under these conditions, the ratio of acetylenic compositions on butadienes is very weak in the charge and the selective hydrogenation of these compounds are difficult to perform resulting in relatively low butadiene losses high.
- the load to be treated can be introduced in an debutanizer.
- the C4 and acetylenic compounds are recovered at the top of the debutanizer, then hydrogenated in a reactor.
- the hydrogenation effluent is again distilled in another distillation column.
- the purified C4 cut is recovered at the top of the distillation column while the oligomers obtained at the bottom of said column are recovered.
- acetylenic compounds were concentrated in the debutanizer since the C5 were separated in the bottom but the overall process requires an additional distillation column, which which increases investment and operating costs.
- the acetylenic ratio on butadienes is unchanged compared to the variant previous.
- One of the objects of the invention is to remedy the drawbacks of the prior art.
- Another object is to selectively hydrogenate acetylenic compounds contained in a C4 cut in the presence of hydrogen without necessarily cause excessive butadiene losses at the lowest cost possible.
- Another object is to purify a cut very rich in butadiene while minimizing as much butadiene losses from distillation and the hydrogenation of said cut.
- the invention relates to a method of treating a charge containing hydrocarbons with at least 4 carbon atoms per molecule, said filler comprising diene compounds and mainly butadiene as well as acetylenic compounds in minor proportion, said process comprising a stage of distillation of the charge introduced into a zone of distillation which includes a rectification zone and a depletion zone and at minus a step of hydrogenation of acetylenic compounds in at least a hydrogenation zone with at least one catalytic bed under conditions suitable hydrogenation in the presence of a gas containing hydrogen, the process being characterized in that it is withdrawn laterally in the liquid phase part of the charge circulating in the distillation zone enriched in acetylenic compounds, up to an appropriate level of withdrawal in the distillation zone and preferably in the exhaustion zone, the stage is carried out of hydrogenation in the hydrogenation zone which is external to the zone of distillation, a hydrogenation effluent depleted in compounds is produced acetylenic and
- rectification area is meant an area above the level supply feed to the distillation column.
- This charge according to the invention can contain at least 20% by weight of butadienes and preferably at least 50% by weight in section C4 alone. Besides, she generally contains at most 20% by weight of acetylenic compounds, advantageously at most 5% and preferably at most 2.5% by weight.
- the withdrawal rate can be at most equal to twice that of the charge introduced into the column, advantageously at most 1.5 times that of the column. It is by drawing from the area depletion a liquid fluid flow rate substantially equal to that of the load entered in the column which gives the best results.
- the charge can be introduced at a level corresponding substantially to the middle of the distillation column, the lateral racking level is located below said middle of the column at a height corresponding to less than five trays theoretical and we recycle the hydrogenation effluent above the middle of the column, at a level corresponding at most to the height of the first five theoretical platforms.
- the increase in temperature linked to hydrogenation is generally small because the quantity of hydrogenated products is very small. Nevertheless, it can be advantageous to control the exothermicity of the hydrogenation step and the temperature of the hydrogenation effluent upstream of the recycling level in the rectification area of the column, especially since it is preferable to reintroduce the fluid at the top of the column at a substantially equal temperature to that of the reintroduction tray, so as not to disturb the column of distillation.
- a hydrocarbon charge 1 comprising a cut.
- C4 resulting from a steam cracker and containing approximately 50% of butadienes and 1 to 2% compared to the C4 cut only of acetylenic compounds is introduced into a column 2 of distillation called debutanizer. This column comprising about 40 theoretical plates, the charge is introduced at the level of the 20 th plate.
- the fraction C4 containing butadiene and approximately 1000 ppm of acetylene compounds is recovered via a line 3. Part of this fraction is reintroduced after condensation 20 and separation 21, in the form of reflux 5 at the top of the column while the other part is recovered by a line 6 for further treatment, extraction by solvent for example.
- This fluid is introduced into at least one hydrogenation reactor 8 supplied with hydrogen by a line 9 under partial pressure conditions which correspond substantially to the stoichiometry of the hydrogenation of the acetylene compounds.
- This reactor contains a fixed downflow bed (introduction from the top of the reactor of the liquid charge) of hydrogenation catalyst which can be palladium stabilized by gold on a gamma alumina support.
- the hydrogenation effluent is collected by a line 10, cooled in exchanger 11 and recycled in the 4th theoretical plate, for example of the rectifying zone of the column, at a temperature substantially equal to that of the 4th tray .
- This effluent contains in particular the olefinic compounds initially present in the charge, the butadienes which have not been substantially hydrogenated thus than the oligomers produced in the hydrogenation zone.
- These compounds oligomers which are heavy products are collected at the bottom of the column by a line 13 as well as the hydrocarbons with 5 carbon atoms per molecule of load. A part is used to be introduced into a reboiler 14 and recycled at the bottom of the column by a line 15.
- the feed level of the feed in the column, the lateral draw-off level and the level of recycling of the hydrogenated effluent are usually chosen in order to obtain 1000 ppm by weight of acetylenics in the C4 cut while minimizing the loss in butadiene 1.3. This charge is introduced at the level of the 20 th theoretical plate of the column.
- the purpose of the column is to separate the C4 section from the other hydrocarbons.
- the hydrogenation effluent is recycled in the rectification zone of the column at the 4th theoretical plate.
- the C5 hydrocarbons as well as the oligomers produced during the hydrogenation reaction will mainly recover at the bottom of the column.
- Conversion rate the conversion rate of a product represents the quantity of product (by mass) that has disappeared.
- butadiene losses represent the quantity of butadiene which is not recovered at the top of the column, that is to say the butadiene which is hydrogenated into butene at the level of the reactor plus the butadiene which is lost at the bottom of the debutanizer in section C5. Losses of 1,3 butadiene, the isomer with commercial interest, are 2.7% while the content of acetylenic compounds in the head section is 1000 ppm, which corresponds to a conversion rate of the vinylacetylene compound of 0.95.
- Example 1 is repeated under identical conditions, but instead of partially withdrawing an effluent from the column, from the exhaustion zone to the rectification zone, it is withdrawn from the rectification zone (10 th tray) and recycling is carried out.
- the withdrawal rate is fixed at 20 T / h, the VAC conversion rate at 0.9.
- the content of acetylenic compounds in the C4 cut collected at the head is approximately 3000 ppm and the losses of butadiene are approximately 2%.
- Example 1 is repeated under identical conditions, but instead of partially withdrawing an effluent from the column, from the exhaustion zone to the rectification zone, it is withdrawn from the exhaustion zone (35 th tray) and the recycled after hydrogenation 32nd tray in the stripping zone.
- the butadiene content at the inlet of the hydrogenation reactor being very low (less than 1%), the losses are therefore negligible.
- the content of acetylenic compounds at the top of the column is very high (greater than 8000 ppm). All the acetylenic compounds entering the column at the feed level (20 th tray) and leaving in the head zone are not hydrogenated by such a device.
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
- Nombre de plateaux théoriques 40, de préférence 35 - 45
- Pression absolue 4 - 10 bar (1 bar = 105 Pa)
- Température de tête : 45 °C, de préférence 30 °C à 50 °C
- Température de fond : 95 °C, de préférence 90 °C à 150 °C
- Pression absolue : 2 à 70 bar (1 bar = 105 Pa), de préférence 5 à 15 bar
- Température : 30 à 60 °C, de préférence 35 à 45 °C
- Vitesse spatiale 3 à 10 h-1, de préférence 4 à 8 h-1
- Rapport H2/composés acétyléniques (mole/mole) : 0,5-3, de préférence 1,0 à 1,1
- Catalyseur : soit le nickel ou une masse de captation contenant du cuivre, soit un métal noble du groupe VIII, de préférence le palladium, stabilisé par au moins un métal Au, Ag, par exemple 0,01 à 1 % poids de métal par rapport au poids total du catalyseur ledit rapport H2/composés acétyléniques sera ajusté en fonction des spécifications requises pour l'effluent de tête de la colonne de distillation.
Charge | C4 | C5 | |
Coupe de tête | Coupe de fond | ||
Phase | Liquide | Liquide | Liquide |
Pourcentages massiques | |||
PROPANE | 0,01 | 0,01 | 0,00 |
PROPADIENE | 0,01 | 0,01 | 0,00 |
PROPYNE | 0,02 | 0,02 | 0,00 |
IBUTANE | 0,27 | 0,38 | 0,00 |
ISOBUTENE | 13,66 | 19,22 | 0,00 |
1BUTENE | 9,06 | 14,40 | 0,01 |
13BUTADIENE | 32,52 | 44,51 | 0,04 |
NBUTANE | 3,53 | 4,96 | 0,02 |
TRANS2BUTENE | 4,26 | 6,66 | 0,06 |
CIS2BUTENE | 2,00 | 3,11 | 0,10 |
VAC | 0,73 | 0,03 | 0,05 |
1BUTYNE (ETAC) | 0,20 | 0,07 | 0,06 |
12BUTADIENE | 0,40 | 0,31 | 0,15 |
ISOPENTANE | 1,67 | 0,44 | 4,68 |
2METHYL1BUTENE | 3,21 | 0,73 | 9,27 |
ISOPRENE | 9,52 | 1,86 | 28.23 |
PENTANE | 3,33 | 0,62 | 9,96 |
TRANS2PENTENE | 1,43 | 0.26 | 4,29 |
PENTADIENE | 3,33 | 0.44 | 10,39 |
CYCLOPENTADIENE | 9,76 | 1,81 | 29,18 |
CYCLOPENTENE | 0,48 | 0,07 | 1,49 |
CYCLOPENTANE | 0,60 | 0,07 | 1,89 |
15ETHYLCYCLOHEXADIENE | - | 0,00 | 0,10 |
123TRIMETHYLINDENE | - | 0,00 | 0,02 |
- Taux de reflux massique liquide/distillat = 1,2
- Teneur en C4 dans la coupe C5 : 0,5 %
Cet effluent est introduit dans le réacteur d'hydrogénation catalytique qui est opéré dans les conditions suivantes, en présence d'hydrogène :
Ex. : Taux de conversion du VAC = 0,95 :
Pertes en butadiène : les pertes en butadiène représentent la quantité de butadiène qui n'est pas récupérée en tête de colonne, c'est-à-dire le butadiène qui est hydrogéné en butène au niveau du réacteur plus le butadiène qui est perdu en fond du débutaniseur dans la coupe C5.
Les pertes en butadiène 1,3, l'isomère à intérêt commercial, sont de 2,7 % tandis que la teneur en composés acétyléniques dans la coupe de tête est de 1000 ppm, ce qui correspond à un taux de conversion du composé vinylacétylène de 0,95.
Dans cette configuration, la teneur en composés acétyléniques dans la coupe C4 recueillie en tête est d'environ 3000 ppm et les pertes en butadiène sont d'environ 2 %.
En revanche, la teneur en composés acétyléniques en tête de colonne est très élevée, (supérieure à 8000 ppm). Tous les composés acétyléniques rentrant dans la colonne au niveau de l'alimentation (20e plateau) et partant dans la zone de tête ne sont pas hydrogénés par un tel dispositif.
Claims (10)
- Procédé de traitement d'une charge comportant des hydrocarbures à au moins 4 atomes de carbone par molécule, ladite charge comportant des composés diéniques et principalement du butadiène ainsi que des composés acétyléniques en proportion mineure, ledit procédé comportant une étape de distillation de la charge introduite dans une zone de distillation qui comprend une zone de rectification et une zone d'épuisement et au moins une étape d'hydrogénation des composés acétyléniques dans au moins une zone d'hydrogénation à au moins un lit catalytique dans des conditions d'hydrogénation appropriées en présence d'un gaz contenant de l'hydrogène, le procédé étant caractérisé en ce que l'on soutire latéralement en phase liquide une partie de la charge circulant dans la zone de distillation enrichie en composés acétyléniques, à la hauteur d'un niveau de soutirage approprié dans la zone de distillation et de préférence dans la zone d'épuisement, on réalise l'étape d'hydrogénation dans la zone d'hydrogénation qui est externe à la zone de distillation, on produit un effluent d'hydrogénation appauvri en composés acétyléniques et enrichi en oligomères et on recycle ledit effluent d'hydrogénation dans la zone de rectification, le procédé étant en outre caractérisé en ce que l'on récupère en tête de la zone de distillation une coupe C4 comportant sensiblement tout le butadiène et appauvrie en composés acétyléniques et en fond de la zone de distillation une coupe C5 enrichie en oligomères.
- Procédé selon la revendication 1 dans lequel la charge est un effluent de vapocraquage qui contient en majorité des hydrocarbures de 4 à 5 atomes de carbone par molécule et de préférence une majeure partie d'hydrocarbures à 4 atomes de carbone.
- Procédé selon l'une des revendications 1 et 2, dans lequel la teneur en butadiènes dans la charge est au moins égale à 20 % poids et de préférence égale à 50 % poids.
- Procédé selon l'une des revendications 1 à 3, dans lequel la charge contient au plus 20 % poids de composés acétyléniques, avantageusement au plus 5 % et de préférence au plus 2,5 %.
- Procédé selon l'une des revendications 1 à 4, dans lequel le débit de soutirage est au plus égal à deux fois celui de la charge, avantageusement au plus égal à une fois et demie le débit de la charge et de préférence sensiblement égal à celui de la charge introduite dans la zone de distillation.
- Procédé selon l'une des revendications 1 à 5 dans lequel la charge est introduite à un niveau correspondant sensiblement au milieu de la colonne de distillation, le niveau de soutirage latéral est situé en dessous dudit milieu de la colonne à une hauteur correspondant à moins de cinq plateaux théoriques et on recycle l'effluent d'hydrogénation au-dessus du milieu de la colonne, à un niveau correspondant au plus à la hauteur des cinq premiers plateaux théoriques.
- Procédé selon l'une des revendications 1 à 6 dans lequel le rapport des concentrations composés acétyléniques / butadiènes au niveau du soutirage latéral est sensiblement le plus élevé.
- Procédé selon l'une des revendications 1 à 7 dans lequel les conditions opératoires de la zone de distillation sont les suivantes :Nombre de plateaux théoriques : 40, de préférence 35 à 45Pression absolue : 4- 10 bar, de préférence 5 barTempérature de tête : 45 °C, de préférence 30°C à 50 °CTempérature de fond : 95 °C, de préférence 90 °C à 150 °C
- Procédé selon l'une des revendications 1 à 8 dans lequel les conditions opératoires dans la zone d'hydrogénation sont les suivantes :Pression absolue : 2 à 70 bar, de préférence 5 à 15 barTempérature : 30 à 60 °C, de préférence 35 °C à 45 °CVitesse spatiale 3 à 10 h-1, de préférence 4 à 8 h-1Rapport H2 / composés acétyléniques (mole/mole)=0,5 à 3, de préférence 1,0 à 1,1Catalyseur métal noble du groupe VIII, de préférence le palladium ; 0,01 à 1 % poids stabilisé par au moins un métal du groupe formé par Au, Ag, Sn.
- Procédé selon l'une des revendications 1 à 4 dans lequel on contrôle la température de l'effluent d'hydrogénation en amont du niveau de recyclage dans la zone de rectification de la colonne de distillation.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0016726 | 2000-12-21 | ||
FR0016726A FR2818637B1 (fr) | 2000-12-21 | 2000-12-21 | Procede de traitement d'hydrocarbures c4 comportant du butadiene et des composes acetylenique comprenant des etapes de distillation et d'hydrogenation selective |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1217060A1 true EP1217060A1 (fr) | 2002-06-26 |
EP1217060B1 EP1217060B1 (fr) | 2006-08-09 |
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EP01403076A Expired - Lifetime EP1217060B1 (fr) | 2000-12-21 | 2001-11-30 | Procédé de traitement d'hydrocarbures C4 comportant du butadiène et des composés acétyléniques comprenant des étapes de distillation et d'hydrogénation sélective |
Country Status (6)
Country | Link |
---|---|
US (1) | US6740787B2 (fr) |
EP (1) | EP1217060B1 (fr) |
JP (1) | JP4340802B2 (fr) |
DE (1) | DE60122097T2 (fr) |
ES (1) | ES2269329T3 (fr) |
FR (1) | FR2818637B1 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2868789A1 (fr) * | 2004-04-09 | 2005-10-14 | Inst Francais Du Petrole | Procede et dispositif de traitement d'une charge comportant du butadiene |
WO2006024616A1 (fr) | 2004-08-28 | 2006-03-09 | Oxeno Olefinchemie Gmbh | Procede de telomerisation d'olefines non cycliques |
DE102008043344A1 (de) | 2008-10-31 | 2010-05-06 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von 1-Alkoxyocta-2,7-dien |
RU2478603C1 (ru) * | 2011-11-03 | 2013-04-10 | Общество с ограниченной ответственностью "Научно-производственное объединение ЕВРОХИМ" (ООО "НПО ЕВРОХИМ") | Реактор для жидкофазного синтеза изопрена |
WO2022089250A1 (fr) * | 2020-10-26 | 2022-05-05 | 中国石油化工股份有限公司 | Procédé d'hydrogénation sélective de gaz résiduaire d'extraction de butadiène et dispositif d'hydrogénation sélective |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7227047B2 (en) * | 2003-08-22 | 2007-06-05 | Exxonmobil Chemical Patents Inc. | Butadiene and isobutylene removal from olefinic streams |
FR2882531B1 (fr) * | 2005-02-25 | 2007-04-27 | Inst Francais Du Petrole | Procede de preparation de catalyseurs multimetalliques utilisables dans des reactions de transformation des hydrocarbures |
US8808533B2 (en) * | 2010-04-23 | 2014-08-19 | IFP Energies Nouvelles | Process for selective reduction of the contents of benzene and light unsaturated compounds of different hydrocarbon fractions |
EP2277980B1 (fr) * | 2009-07-21 | 2018-08-08 | IFP Energies nouvelles | Procédé de réduction sélective de la teneur en benzène et en composés insatures legers de differentes coupes hydrocarbures |
CN102381920B (zh) * | 2010-09-03 | 2013-08-14 | 中国石油化工股份有限公司 | 一种选择性加氢脱除碳四馏分中炔烃的方法 |
WO2014055249A1 (fr) * | 2012-10-04 | 2014-04-10 | Lummus Technology Inc. | Procédé d'extraction de butadiène |
US11905472B2 (en) | 2021-04-27 | 2024-02-20 | Kellogg Brown & Root Llc | On-site solvent generation and makeup for tar solvation in an olefin plant |
US11884608B2 (en) | 2021-04-27 | 2024-01-30 | Kellogg Brown & Root Llc | Dimerization of cyclopentadiene from side stream from debutanizer |
US20220340504A1 (en) * | 2021-04-27 | 2022-10-27 | Kellogg Brown & Root Llc | Upgrading streams comprising c3 and c4 hydrocarbons |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0273900A1 (fr) * | 1986-12-30 | 1988-07-06 | Fina Research S.A. | Procédé d'hydrogénation sélective des acétylènes |
WO1997024413A1 (fr) * | 1995-12-27 | 1997-07-10 | Institut Français Du Petrole | Procede d'hydrogenation selective d'une coupe d'hydrocarbures |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2523149A1 (fr) * | 1982-03-15 | 1983-09-16 | Catalyse Soc Prod Francais | Nouveau catalyseur supporte palladium-or, sa preparation et son utilisation dans les reactions d'hydrogenation selective d'hydrocarbures diolefiniques et/ou acetyleniques |
-
2000
- 2000-12-21 FR FR0016726A patent/FR2818637B1/fr not_active Expired - Fee Related
-
2001
- 2001-11-30 ES ES01403076T patent/ES2269329T3/es not_active Expired - Lifetime
- 2001-11-30 EP EP01403076A patent/EP1217060B1/fr not_active Expired - Lifetime
- 2001-11-30 DE DE60122097T patent/DE60122097T2/de not_active Expired - Lifetime
- 2001-12-21 US US10/024,500 patent/US6740787B2/en not_active Expired - Lifetime
- 2001-12-21 JP JP2001388596A patent/JP4340802B2/ja not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0273900A1 (fr) * | 1986-12-30 | 1988-07-06 | Fina Research S.A. | Procédé d'hydrogénation sélective des acétylènes |
WO1997024413A1 (fr) * | 1995-12-27 | 1997-07-10 | Institut Français Du Petrole | Procede d'hydrogenation selective d'une coupe d'hydrocarbures |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2868789A1 (fr) * | 2004-04-09 | 2005-10-14 | Inst Francais Du Petrole | Procede et dispositif de traitement d'une charge comportant du butadiene |
WO2005108529A1 (fr) * | 2004-04-09 | 2005-11-17 | Institut Francais Du Petrole | Procede et dispositif de traitement d'une charge comportant du butadiene |
US7935855B2 (en) | 2004-04-09 | 2011-05-03 | IFP Energies Nouvelles | Process and apparatus for treating a feed comprising butadiene |
WO2006024616A1 (fr) | 2004-08-28 | 2006-03-09 | Oxeno Olefinchemie Gmbh | Procede de telomerisation d'olefines non cycliques |
DE102008043344A1 (de) | 2008-10-31 | 2010-05-06 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von 1-Alkoxyocta-2,7-dien |
RU2478603C1 (ru) * | 2011-11-03 | 2013-04-10 | Общество с ограниченной ответственностью "Научно-производственное объединение ЕВРОХИМ" (ООО "НПО ЕВРОХИМ") | Реактор для жидкофазного синтеза изопрена |
WO2022089250A1 (fr) * | 2020-10-26 | 2022-05-05 | 中国石油化工股份有限公司 | Procédé d'hydrogénation sélective de gaz résiduaire d'extraction de butadiène et dispositif d'hydrogénation sélective |
Also Published As
Publication number | Publication date |
---|---|
FR2818637A1 (fr) | 2002-06-28 |
US6740787B2 (en) | 2004-05-25 |
JP2002241768A (ja) | 2002-08-28 |
DE60122097D1 (de) | 2006-09-21 |
DE60122097T2 (de) | 2006-12-21 |
FR2818637B1 (fr) | 2003-02-07 |
ES2269329T3 (es) | 2007-04-01 |
EP1217060B1 (fr) | 2006-08-09 |
US20020128528A1 (en) | 2002-09-12 |
JP4340802B2 (ja) | 2009-10-07 |
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