FR2506298A2 - Fuel-grade alcohol prodn. from synthesis gas - with recycle of ethanol to increase propanol and butanol yields - Google Patents

Fuel-grade alcohol prodn. from synthesis gas - with recycle of ethanol to increase propanol and butanol yields Download PDF

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Publication number
FR2506298A2
FR2506298A2 FR8110192A FR8110192A FR2506298A2 FR 2506298 A2 FR2506298 A2 FR 2506298A2 FR 8110192 A FR8110192 A FR 8110192A FR 8110192 A FR8110192 A FR 8110192A FR 2506298 A2 FR2506298 A2 FR 2506298A2
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FR
France
Prior art keywords
ethanol
alcohols
mixture
methanol
propanol
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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.)
Granted
Application number
FR8110192A
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French (fr)
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FR2506298B2 (en
Inventor
Andre Sugier
Edouard Freund
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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Priority claimed from FR7633046A external-priority patent/FR2369234A1/en
Application filed by IFP Energies Nouvelles IFPEN filed Critical IFP Energies Nouvelles IFPEN
Priority to FR8110192A priority Critical patent/FR2506298A2/en
Publication of FR2506298A2 publication Critical patent/FR2506298A2/en
Application granted granted Critical
Publication of FR2506298B2 publication Critical patent/FR2506298B2/fr
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
    • 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
    • B01J23/78—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 alkali- or alkaline earth metals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/1512—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Abstract

Prodn. of alcohols, esp. primary satd. straight-chain alcohols, is effected as in the Parent Patent by reacting CO with H2 in the presence of a catalyst of compsn. (Cu)x(Co)y(M)z(A)v (where M is Cr, Fe, V and/or Mn; A is one or more alkali metals; x=0.1-1; y=0.1-1; z=0.2-1; v is 0.001-0.25 times the sum of x+y+z). The improvement comprises fractionating the reaction prod. to recover some or all of the ethanol, and recycling the ethanol to the reactor to convert at least part of the ethanol to n-propanol and n-butanol. The prods. can be used as blending stocks for gasoline motor fuels. Increasing the amt. of 3-4C alcohols in the prod. increases the solubility of methanol in the blended fuels and improves their water tolerance.

Description

La présente demande de brevet d'addition concerne une amélioration du procédé de la demande de brevet principal1 amélioration qui consiste à recycler une partie au moins de l'éthanol produit dans la zone catalytique de synthèse d'alcools primaires de façon à convertir au moins la majeure partie de l'éthanol en au moins du n-propanol et du n-butanol.The present patent application relates to an improvement of the process of the main patent application1 improvement which consists in recycling at least part of the ethanol produced in the catalytic zone for synthesis of primary alcohols so as to convert at least the most of the ethanol into at least n-propanol and n-butanol.

En outre, conformément a la demande de ce brevet d'addition, une partie au moins ou la totalité des alcools obtenus au cours du procédé peut être mélangée à une essence de type normal ou de type super pour automobile, c'est-à-dire à une essence d'hydrocarbures, pour former un carburant automobile.Furthermore, in accordance with the request of this patent, at least some or all of the alcohols obtained during the process can be mixed with a gasoline of normal type or of super type for automobile, that is to say say to a petroleum hydrocarbon, to form an automotive fuel.

Si de l'éthanol est présent dans le mélange d'alcools fabriqué conformément au procédé de la demande principale cet éthanol ne nuit pas aux qualités de l'essence ou du carburant global obtenu, mais n'apporte aucune amélioration particulière à l'essence ou au carburant global (effet neutre). Le procédé de la présente addition a donc pour hut de transformer l'éthanol contenu dans l'effluent de la première zone de réaction au moins en partie en n-propanol et n-butanol, de préférence en n-butanol, alcool connu comme produit adéquat pour réaliser la solubilisation du méthanol dans une essence ou un carburant et pour augmenter la tolérance à l'eau de mélanges essences d'hydrocarbures et méthanol et éventuellement d'alcools supérieurs.If ethanol is present in the mixture of alcohols produced in accordance with the process of the main application, this ethanol does not harm the qualities of the gasoline or of the overall fuel obtained, but does not bring any particular improvement to the gasoline or to global fuel (neutral effect). The process of the present addition therefore aims to transform the ethanol contained in the effluent of the first reaction zone at least in part into n-propanol and n-butanol, preferably into n-butanol, alcohol known as product suitable for solubilizing methanol in a petrol or a fuel and for increasing the water tolerance of gasoline and methanol mixtures and possibly higher alcohols.

Cette transformation de l'éthanol s'opère par recyclage de cet éthanol dans la zone de réaction et provoque une augmentation appréciable du pourcentage de la fraction des alcools C3-C4. Généralement, il arrive que du méthanol soit également recyclé vers la
zone de réaction, en provenance de cette première zone de réaction.This transformation of ethanol takes place by recycling this ethanol in the reaction zone and causes an appreciable increase in the percentage of the fraction of C3-C4 alcohols. Generally, methanol is also sometimes recycled to the
reaction zone, coming from this first reaction zone.

Pour effectuer le recyclage de l'éthanol, l'on fractionne d'abord une partie au moins de l'effluent de la zone de réaction (après avoir éventuellement d'abord déshydraté ledit effluent, effluent renfermant essentiellement un mélange de méthanol et d'alcools homologues supérieurs).In order to recycle the ethanol, at least part of the effluent from the reaction zone is first fractionated (after having optionally dehydrated said effluent first, effluent containing essentially a mixture of methanol and higher homologous alcohols).

On recueille ainsi séparément une partie au moins de méthanol produit. En raison des points d'ébullition voisins de l'éthanol et de l'isopropanol, l'on recueille généralement un mélange d'éthanol et dtisopropanol (ainsi qu'éventuellement du méthanol).At least part of the methanol produced is thus collected separately. Due to the boiling points close to ethanol and isopropanol, a mixture of ethanol and dtisopropanol (as well as possibly methanol) is generally collected.

Le mélange de méthanol et d'alcools homologues supérieurs (renfermant au moins 2 atomes de carbone par molécule), obtenu conformément au procédé de cette demande de brevet d'addition, c1 est-à-dire après un recyclage d'éthanol, convient alors particulièrement bien pour être ajouté à une essence d'hydrocarbures, c'est-à-dire à une essence automobile de type normal ou de type super de façon à obtenir ainsi un excellent carburant automobile.The mixture of methanol and higher homologous alcohols (containing at least 2 carbon atoms per molecule), obtained in accordance with the process of this patent application, ie after recycling of ethanol, is then suitable particularly good for being added to a petrol of hydrocarbons, that is to say to a petrol of normal type or of super type so as to thus obtain an excellent automotive fuel.

D'une façon générale, le mélange de méthanol et d'alcools homologues supérieurs (renfermant au moins 2 atomes de carbone par molécule) contient en poids 25 à 90 % de méthanol et 75 à 10 % d'alcools homologues supérieurs à 2 ou plus atomes de carbone par molécule. De préférence, le mélange de méthanol et d'alcools homologues supérieurs contient, en poids, 60 à 90 % de méthanol et 40 à 10 % d'alcools hoologues. Plus particulièrement ce mélange contient, en poids, 79 à 87 %, et par exemple environ 85 %, de méthanol et 21 à 13 %, par exemple environ 15 %, d'alcools homologues.Generally, the mixture of methanol and higher homologous alcohols (containing at least 2 carbon atoms per molecule) contains by weight 25 to 90% of methanol and 75 to 10% of homologous alcohols higher than 2 or more carbon atoms per molecule. Preferably, the mixture of methanol and higher homologous alcohols contains, by weight, 60 to 90% of methanol and 40 to 10% of hoologic alcohols. More particularly, this mixture contains, by weight, 79 to 87%, and for example approximately 85%, of methanol and 21 to 13%, for example approximately 15%, of homologous alcohols.

Un bon carburant automobile constitué d'une essence d' hydrocarbures et d'un mélange de méthanol et d'alcools homologues supérieurs (renfermant au moins 2 atomes de carbone par molécule) préparé conformément à la présente demande de brevet d'addition, renferme, en poids, 60 à 97 % de ladite essence d'hydrocarbures et 3 à 40 % dudit mélange. De préférence, un tel carburant automobile peut renfermer 85 à 97 % de ladite essence d'hydrocarbures et 3 à 15 % dudit mélange. A titre de carburant, on peut citer ceux renfermant 85 % d'ne essence automobile (essence super par exemple), et 15 % dudit mélange renfermant lui même, en poids. 80 % de méthanol et 20 % d'alcools homologues (soit 85 % d'essence, 12 % de méthanol et 3 % d'alcools homologues) ou ceux renfermant 90 % d'une essence automobile (essence super par exemple), et 10 % d'un mélange renfermant lui-même, en poids, 75 % de méthanol et 25 % d'alcools homologues (soit 90 % d'essence, 7,5 % de méthanol et 2,5 % d'alcools homologues).A good automotive fuel consisting of a petroleum hydrocarbon and a mixture of methanol and higher homologous alcohols (containing at least 2 carbon atoms per molecule) prepared in accordance with the present patent application, contains, by weight, 60 to 97% of said gasoline of hydrocarbons and 3 to 40% of said mixture. Preferably, such an automotive fuel can contain 85 to 97% of said petroleum hydrocarbon and 3 to 15% of said mixture. As fuel, mention may be made of those containing 85% of automobile gasoline (super petrol for example), and 15% of said mixture containing itself, by weight. 80% methanol and 20% homologous alcohols (i.e. 85% petrol, 12% methanol and 3% homologous alcohols) or those containing 90% automotive petrol (super petrol for example), and 10 % of a mixture itself containing, by weight, 75% methanol and 25% homologous alcohols (i.e. 90% gasoline, 7.5% methanol and 2.5% homologous alcohols).

A titre d'exemple, on peut opérer de façon à ce que, dans la boucle de recyclage, la conversion choisie de l'éthanol soit d'environ 10 % en n-propanol et de 24 % en n-butanol ; pour l'isopropanol, on pourrait retenir une conversion de 20 % en alcools C5-C6,par exemple. For example, one can operate so that, in the recycling loop, the chosen conversion of ethanol is about 10% into n-propanol and 24% into n-butanol; for isopropanol, one could retain a conversion of 20% into C5-C6 alcohols, for example.

Claims (7)

REVENDICATIONS 1. - Procédé selon la revendication 1 du brevet principal pour la fabrication d'alcools, caractérisé en ce que le mélange d'alcools, obtenu à l'issue de la zone catalytique de réaction est fractionné au moins en partie de façon à recueillir au moins en partie l'éthanol produit dans ladite zone catalytique de réaction et en ce que une partie au moins de l'éthanol ainsi recueilli est renvoyée dans ladite zone catalytique de façon à convertir au moins en partie de l'éthanol en au moins du n-propanol et du n-butanol.1. - Method according to claim 1 of the main patent for the manufacture of alcohols, characterized in that the mixture of alcohols obtained at the end of the catalytic reaction zone is fractionated at least in part so as to collect at at least in part the ethanol produced in said catalytic reaction zone and in that at least part of the ethanol thus collected is returned to said catalytic zone so as to convert at least in part ethanol into at least n -propanol and n-butanol. 2. - Procédé selon la revendication 1 dans lequel ledit mélange d'alcools obtenus dans la zone catalytique de réaction est fractionné de façon â recueillir au moins en partie de méthanol et de l'isopropanol formés dans ladite zone catalytique de réaction et dans lequel une partie au moins de l'éthanol et de l'isopropanol ainsi recueillis est renvoyée dans ladite zone catalytique de réaction de façon à convertir une partie au moins de l'éthanol en au moins du n-propanol et du n-butanol et une partie au moins de l'isopropanol en au moins des alcools ayant généralement 5 ou 6 atomes de carbone par molécule.2. - Method according to claim 1 wherein said mixture of alcohols obtained in the catalytic reaction zone is fractionated so as to collect at least in part methanol and isopropanol formed in said catalytic reaction zone and in which a at least part of the ethanol and isopropanol thus collected is returned to said catalytic reaction zone so as to convert at least part of the ethanol into at least n-propanol and n-butanol and a part to less isopropanol into at least alcohols generally having 5 or 6 carbon atoms per molecule. 3. - Procédé selon l'une des revendications 1 et 2, dans lequel, à l'issue dudit procédé, on obtient un mélange renfermant, en poids, 25 à 90 % de méthanol et 75 à 10 % d'alcools homologues supérieurs possédant au moins deux atomes de carbone par molécule.3. - Method according to one of claims 1 and 2, wherein, at the end of said process, a mixture is obtained containing, by weight, 25 to 90% of methanol and 75 to 10% of higher homologous alcohols having at least two carbon atoms per molecule. 4. - Procédé selon la revendication 3 dans lequel on obtient un mélange renfermant, en poids, 60 à 90 % de méthanol et 40 à 10 % d'alcools homologues. 4. - Method according to claim 3 wherein a mixture is obtained containing, by weight, 60 to 90% of methanol and 40 to 10% of homologous alcohols. 5. - Procédé selon la revendication 4, dans lequel ledit mélange renferme 79 à 87 % de méthanol et 21 à 13 % d'alcools homologues.5. - Method according to claim 4, wherein said mixture contains 79 to 87% methanol and 21 to 13% of homologous alcohols. 6. - Procédé selon la revendication 3 dans lequel ledit mélange est ajouté à une essence d'hydrocarbures, en vue.d'obtenir un carburant automobile renfermant, en poids, 60 à 97 % de ladite essence d'hydrocarbures et 3à 40 % dudit mélange.6. - Method according to claim 3 wherein said mixture is added to a gasoline of hydrocarbons, in view of obtaining a motor fuel containing, by weight, 60 to 97% of said gasoline of hydrocarbons and 3 to 40% of said mixed. 7. - Procédé selon la revendication 6 dans lequel le carburant renferme, en poids, 85 à 97 % de ladite essence et 3 à 15 % dudit mélange. 7. - Method according to claim 6 wherein the fuel contains, by weight, 85 to 97% of said gasoline and 3 to 15% of said mixture.
FR8110192A 1976-10-29 1981-05-20 Fuel-grade alcohol prodn. from synthesis gas - with recycle of ethanol to increase propanol and butanol yields Granted FR2506298A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR8110192A FR2506298A2 (en) 1976-10-29 1981-05-20 Fuel-grade alcohol prodn. from synthesis gas - with recycle of ethanol to increase propanol and butanol yields

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR7633046A FR2369234A1 (en) 1976-10-29 1976-10-29 ALC MANUFACTURING PROCESS
FR8110192A FR2506298A2 (en) 1976-10-29 1981-05-20 Fuel-grade alcohol prodn. from synthesis gas - with recycle of ethanol to increase propanol and butanol yields

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FR2506298A2 true FR2506298A2 (en) 1982-11-26
FR2506298B2 FR2506298B2 (en) 1984-01-13

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4521394A (en) * 1983-05-27 1985-06-04 Uop Inc. Conversion of gases to useable products
WO2017204975A1 (en) * 2016-05-26 2017-11-30 Exxonmobil Chemical Patents Inc. Oxygenate synthesis and homologation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4521394A (en) * 1983-05-27 1985-06-04 Uop Inc. Conversion of gases to useable products
WO2017204975A1 (en) * 2016-05-26 2017-11-30 Exxonmobil Chemical Patents Inc. Oxygenate synthesis and homologation

Also Published As

Publication number Publication date
FR2506298B2 (en) 1984-01-13

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