US2952612A - Production of high octane motor fuel with an alkyl ether additive - Google Patents

Production of high octane motor fuel with an alkyl ether additive Download PDF

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Publication number
US2952612A
US2952612A US668303A US66830357A US2952612A US 2952612 A US2952612 A US 2952612A US 668303 A US668303 A US 668303A US 66830357 A US66830357 A US 66830357A US 2952612 A US2952612 A US 2952612A
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United States
Prior art keywords
ether
gasoline
catalytically cracked
catalytically
cracked gasoline
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Expired - Lifetime
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US668303A
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English (en)
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Richard P Trainer
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Shell USA Inc
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Shell Oil Co
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Publication date
Priority to NL103620D priority Critical patent/NL103620C/xx
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US668303A priority patent/US2952612A/en
Priority to FR1207533D priority patent/FR1207533A/fr
Priority to DEN15267A priority patent/DE1103493B/de
Priority to GB20396/58A priority patent/GB829072A/en
Application granted granted Critical
Publication of US2952612A publication Critical patent/US2952612A/en
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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
    • C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
    • 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
    • C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
    • C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
    • C10G69/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one step of catalytic cracking in the absence of hydrogen
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • 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

  • This invention relates to the production of quality automotive motor fuel through catalytic cracking, hydrotreating, and blending.
  • the backbone, so to speak, of gasoline for automotive use is catalytically cracked gasoline. It is the practice to charge the maximum amount of suitable oils boiling above gasoline to catalytic cracking to thereby maximize the yield of this material. Due to the excellent quality of catalytically cracked gasoline it is possible to blend with it minor amounts of lower quality materials such as straight run gasoline. In order to maximize the utilization of such low cost materials it is the practice in many instances to add to the blend other high octane materials such, for example, as alkylate, aromatic extracts and catalytically reformed gasoline. Of course, small amounts of butane are incorporated to obtain the desired vapor pressure of the final blend and the gasoline is usually leaded.
  • saturated alkyl ethers and particularly those having a branched chain and boiling within the range of about 89 F. to about 180 F.
  • Di-isopropyl ether was used to a limited extent during World War II in aviation gasoline. These ethers would be efiective in automotive motor fuel. They are, however, so costly that they have not been used in automotive fuel, or, for that matter, even in aviation gasoline, since the war.
  • the transition point where reduction of the bromine number by hydrogenation passes from bad to good is at about 11% ether based on the catalytically cracked gasoline or about 10% in the blend. At this point a small reduction of the bromine number by a very light hydrogenation has no effect; a more drastic reduction in the bromine number is still harmful. At still higher ether concentrations the partial reduction of the bromine number by hydrogenation is advantageous and the advantage increases as the concentration of ether in the'blend is increased. This trend persists at least up to about 44% concentration of the ether beyond which tests were considered to be unwarranted due to the high cost of blends with such high concentrations of ether. At this point (44%) the saving in ether effected through the partial reduction of the bromine number is around 40%, is. the amount of ether required to produce a given volume of a blend having a given octane number is 40% less than would be required without the hydrogenation.
  • the concentration has only one meaning.
  • the present invention allows a desired octane level to be reached With reduced amounts of ether.
  • concentrations above this break point there are therefore two ether concentrations to be considered, namely, (1) the concentration of ether required .to achieve a given octane level without partial reduction of the bromine number of the catalytically cracked gasoline and (2) the concentration of ether required to achieve the same octane level with partial reduction of the bromine number.
  • concentration of ether required to achieve the same octane level with partial reduction of the bromine number.
  • the figures in the first column of Table II labelled three times the percent ether in the blend. For example in the case of the blend containing 31% ether where a saving of about 28% is indicated at a bromine number reduction of 50%, the saving is still 23% if the bromine number reduction is increased to
  • the eifects noted are obtained with cataltyically cracked gasoline produced by the catalytic cracking of any hydrocarbon oil boiling above gasoline with a solid silica-alumina type cracking catalyst. It is known that the silica-alumina cracking catalysts whether of high or low alumina content or of natural or synthetic origin give practically identical gasolines from various oils. Other cracking catalysts such as silica-magnesia and HIE treated alumina give difierent product distributions and the gasolines produced with them may not behave in the manner shown when blended with the ethers.
  • the catalytically cracked gasoline is produced by the catalytic cracking of a higher boiling hydrocarbon oil at temperatures in the range of 900 to about 1100 F., pressures in the range of 5 to'about 75'p.s.i.g.
  • the cracking may be etfected in a fluid bed reactor, moving bed reactor or a riser reactor such as described in U. S. application Serial Number 586,105, filed May 21, 1956.
  • the products from the cracking reactor are preferably separated into a normally gaseous fraction including substantial amounts of olefins, a catalytically cracked gasoline boiling up to about 185-25.0 R, and a heavy naphtha.
  • This naphtha fraction is advantageously catalytically reformed and then combined with the blend of the hydrogenated catalytically cracked gasoline and the ether.
  • the reforming may be affected by any of the known catalytic reforming processes.
  • the naptha is Platformed by a platinum-alumina-halogencatalyst at a temperature of 900-960 F. and pressure of 150-450 p.s.i.g. in the presence of recycled hydrogen.
  • the amount of reformed naphtha or other blending materials that may be incorporated to produce the finished gasoline of desired octane number may be increased; such components can in fact become the chief component in the gasoline.
  • the advantage can be exploited in a difierent way.
  • the naphtha may be used in the same amount but may be reformed to a lesser degree as by the use of less severe reforming conditions, thereby lowering the reforming cost and improving the yield of reformed product.
  • the catalytically cracked gasoline is catalytically hydrogenated to reduce the bromine number at least to some degree and preferably to about the extents indicated.
  • the bromine number is initially at least around 100.
  • the hydrogenation may be effected with any of the various hydrogenation catalysts hitherto used for hydrogenation of petroleum products.
  • Preferred catalysts are prepared by incorporating oxides or sulfides of one or more to the metals Ou, Co, Ni, Cr, Mo, W with an aluminous carrier material such asactivated alumina or microporous silica-alumina composites.
  • the hydrogenation is efiectd at temperatures in the range of about 300 to 800 F., preferably about 500 to 700 F.
  • the process may be carried out under pressures from slightly above atmospheric up to about 100 atmospheres.
  • the rate of gasoline and hydrogen feed to the hydrogenation zone may be adjusted such that the desired degree of bromine number reduction is obtained.
  • a bromine number reduction of from about 50 to about there is a substantial exothermic heat effect which makes control of the temperature difiicult.
  • This difiiculty can be minimized by using two small reactors in series .with'intermediate cooling of the reactant stream, or by adding to the feed a sizable amount of a substantially inert hydrocarbon diluent material having a sufliciently different boiling range that it may be separated from the partially hydrogenated catalytically cracked gasoline product by a subsequent fractional distillation.
  • the ether is advantageously made from the olefinic gaseous fraction mentioned above. This is advantageous in two respects. -In the first place this materially upgrades this gaseous product. In the second place the conversion of propylene and/or butylene to ethers reduces the amount of polymers which would otherwise be made fi'om them. This is advantageous since the polymers tend to degrade the quality of the gasoline in which they are blended.
  • the conversion of the gaseous olefins to ethers may be efiected by reacting them with a suitable alcohol such as methanol, or isopropanol by known methods e.g., as described in U.S. Patent No. 2,480,940 to Leum.
  • a very desirable arrangement which produces large Volumes of the ether is to hydrate the propylene to isopropyl alcohol (a known process) and then react this alcohol with the butylene-butane fraction or additional propylene whereby isopropyl tertiary butyl ether or di-isopropyl ether is formed.
  • Still larger volumes of the ether may be produced but at increased cost, by reacting both the propylene and the isobutylene with methanol to produce methyl isopropyl and methyl tertiary butyl ethers.
  • the etherification reaction normally does not consume all of the alcohol in the reaction mixture. Unreacted alcohol may be removed by water washing the ether product or in some cases by distillation.
  • the ethers in question are normally liquid and are easily separated from the unreacted hydrocarbons (e.g., butane-butylene fractions) by a simple distillation.
  • the flashed distillate and deasphalted oil were catalytically cracked together in a commercial fluidized catalyst cracking unit using a synthetic silica-alumina cracking catalyst.
  • the product was fractionated in the plant in the normal manner to separate a propane-propylene fraction, a butanebutylene fraction, a catalytically cracked gasoline having the properties given above, and various heavier materials.
  • the catalytically cracked gasoline was partially bydrogenated with a commercial Co-Mo/alumina catalyst at 536-608 F. and 200 p.s.i.g. at a hydrogen to oil mole ratio of 2.8 and a liquid hourly space velocity of 4 to reduce the bromine number by 63%,
  • isopropyl tertiary butyl ether was found equally effective as the methyl tertiary butyl ether and methyl tertiary amyl ether and ethyl tertiary butyl ether were intermediate the isopropyl tertiary butyl and di-isopropyl ether.
  • the F-l-S octane number is the CFR designation for the ASTM Research Octane Number D908-47T for the material containing 3 cc. of ethyl fluid per US, gallon.
  • the bromine numbers were determined by the meth od described by A. Polgar et al. in Organic Analysis, vol. III, p. 237, Interscience Publishers, N.Y.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US668303A 1957-06-27 1957-06-27 Production of high octane motor fuel with an alkyl ether additive Expired - Lifetime US2952612A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL103620D NL103620C (en, 2012) 1957-06-27
US668303A US2952612A (en) 1957-06-27 1957-06-27 Production of high octane motor fuel with an alkyl ether additive
FR1207533D FR1207533A (fr) 1957-06-27 1958-06-25 Fabrication de carburant à indice d'octane élevé
DEN15267A DE1103493B (de) 1957-06-27 1958-06-25 Verfahren zur Herstellung von Benzin mit hoher Octanzahl
GB20396/58A GB829072A (en) 1957-06-27 1958-06-25 Production of high octane motor gasoline

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US668303A US2952612A (en) 1957-06-27 1957-06-27 Production of high octane motor fuel with an alkyl ether additive

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US (1) US2952612A (en, 2012)
DE (1) DE1103493B (en, 2012)
FR (1) FR1207533A (en, 2012)
GB (1) GB829072A (en, 2012)
NL (1) NL103620C (en, 2012)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3482952A (en) * 1968-04-29 1969-12-09 Chevron Res Process for production of gasoline
US3836342A (en) * 1972-06-23 1974-09-17 Sun Research Development Gasoline containing a methyl phenol and an ether
US3849082A (en) * 1970-06-26 1974-11-19 Chevron Res Hydrocarbon conversion process
DE2444528A1 (de) * 1973-09-18 1975-03-20 Magyar Asvanyolaj Es Foeldgaz Treibstoff fuer motoren mit funkenzuendung und zusatz fuer diesen
US3912463A (en) * 1970-06-26 1975-10-14 Chevron Res Hydrocarbon conversion process
US3976437A (en) * 1972-06-23 1976-08-24 Sun Ventures, Inc. Composition comprising a methyl phenol and an ether for gasoline fuels
FR2411881A1 (fr) * 1977-12-16 1979-07-13 Gulf Canada Ltd Preparation d'une essence d'hydrocarbures contenant de l'ether methyl amylique tertiaire
US4244704A (en) * 1980-01-04 1981-01-13 Texaco Inc. Gasoline composition
US4252541A (en) * 1975-11-28 1981-02-24 Texaco Inc. Method for preparation of ethers
FR2477570A1 (fr) * 1980-03-10 1981-09-11 Inst Francais Du Petrole Hydrogenation et etherification d'une coupe insaturee c5 d'hydrocarbures en vue d'en ameliorer l'indice d'octane et d'en reduire la teneur en mono-olefines
DE3116734A1 (de) * 1981-04-28 1982-11-18 Veba Oel AG, 4660 Gelsenkirchen-Buer Vergaserkraftstoff
US4519809A (en) * 1984-04-23 1985-05-28 Exxon Research & Engineering Co. Method for reducing water sensitivity of ether containing gasoline compositions
WO1993016150A1 (en) * 1992-02-07 1993-08-19 Nrg-Technologies, L.P. Composition and method for producing a multiple boiling point ether gasoline component
US5256167A (en) * 1991-05-21 1993-10-26 Nippon Oil Co., Ltd. Gasoline
US5401280A (en) * 1992-10-14 1995-03-28 Nippon Oil Co., Ltd. Lead-free, high-octane gasoline

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB445503A (en) * 1935-06-04 1936-04-14 Standard Oil Dev Co Improvements relating to motor fuels
GB507246A (en) * 1937-02-06 1939-06-13 Standard Oil Dev Co An improved manufacture of motor fuels
US2289716A (en) * 1939-10-19 1942-07-14 Standard Oil Co Catalytic motor fuel production
US2292677A (en) * 1939-05-17 1942-08-11 Universal Oil Prod Co Catalytic conversion of hydrocarbons
US2409746A (en) * 1940-07-31 1946-10-22 Shell Dev Motor fuels
US2436170A (en) * 1946-01-29 1948-02-17 Standard Oil Dev Co Finishing of aviation naphthas
US2740751A (en) * 1952-02-23 1956-04-03 Universal Oil Prod Co Reforming of both straight run and cracked gasolines to provide high octane fuels

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB445503A (en) * 1935-06-04 1936-04-14 Standard Oil Dev Co Improvements relating to motor fuels
GB507246A (en) * 1937-02-06 1939-06-13 Standard Oil Dev Co An improved manufacture of motor fuels
US2292677A (en) * 1939-05-17 1942-08-11 Universal Oil Prod Co Catalytic conversion of hydrocarbons
US2289716A (en) * 1939-10-19 1942-07-14 Standard Oil Co Catalytic motor fuel production
US2409746A (en) * 1940-07-31 1946-10-22 Shell Dev Motor fuels
US2436170A (en) * 1946-01-29 1948-02-17 Standard Oil Dev Co Finishing of aviation naphthas
US2740751A (en) * 1952-02-23 1956-04-03 Universal Oil Prod Co Reforming of both straight run and cracked gasolines to provide high octane fuels

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3482952A (en) * 1968-04-29 1969-12-09 Chevron Res Process for production of gasoline
US3849082A (en) * 1970-06-26 1974-11-19 Chevron Res Hydrocarbon conversion process
US3912463A (en) * 1970-06-26 1975-10-14 Chevron Res Hydrocarbon conversion process
US3836342A (en) * 1972-06-23 1974-09-17 Sun Research Development Gasoline containing a methyl phenol and an ether
US3976437A (en) * 1972-06-23 1976-08-24 Sun Ventures, Inc. Composition comprising a methyl phenol and an ether for gasoline fuels
DE2444528A1 (de) * 1973-09-18 1975-03-20 Magyar Asvanyolaj Es Foeldgaz Treibstoff fuer motoren mit funkenzuendung und zusatz fuer diesen
US4252541A (en) * 1975-11-28 1981-02-24 Texaco Inc. Method for preparation of ethers
FR2411881A1 (fr) * 1977-12-16 1979-07-13 Gulf Canada Ltd Preparation d'une essence d'hydrocarbures contenant de l'ether methyl amylique tertiaire
US4244704A (en) * 1980-01-04 1981-01-13 Texaco Inc. Gasoline composition
FR2477570A1 (fr) * 1980-03-10 1981-09-11 Inst Francais Du Petrole Hydrogenation et etherification d'une coupe insaturee c5 d'hydrocarbures en vue d'en ameliorer l'indice d'octane et d'en reduire la teneur en mono-olefines
EP0035935B1 (fr) * 1980-03-10 1983-12-28 Institut Français du Pétrole Hydrogénation et éthérification d'une coupe insaturée C5 d'hydrocarbures en vue d'en améliorer l'indice d'octane et d'en réduire la teneur en mono-oléfines
DE3116734A1 (de) * 1981-04-28 1982-11-18 Veba Oel AG, 4660 Gelsenkirchen-Buer Vergaserkraftstoff
US4468233A (en) * 1981-04-28 1984-08-28 Veba Oel Ag Motor fuel containing tert-butyl ethers
US4519809A (en) * 1984-04-23 1985-05-28 Exxon Research & Engineering Co. Method for reducing water sensitivity of ether containing gasoline compositions
US5256167A (en) * 1991-05-21 1993-10-26 Nippon Oil Co., Ltd. Gasoline
WO1993016150A1 (en) * 1992-02-07 1993-08-19 Nrg-Technologies, L.P. Composition and method for producing a multiple boiling point ether gasoline component
US6017371A (en) * 1992-02-07 2000-01-25 Nrg Technologies, Inc. Composition and method for producing a multiple boiling point ether gasoline component
US5401280A (en) * 1992-10-14 1995-03-28 Nippon Oil Co., Ltd. Lead-free, high-octane gasoline

Also Published As

Publication number Publication date
DE1103493B (de) 1961-03-30
GB829072A (en) 1960-02-24
NL103620C (en, 2012)
FR1207533A (fr) 1960-02-17

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