WO2018118346A1 - Procédé permettant de fabriquer de l'essence à indice d'octane élevé - Google Patents

Procédé permettant de fabriquer de l'essence à indice d'octane élevé Download PDF

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Publication number
WO2018118346A1
WO2018118346A1 PCT/US2017/063381 US2017063381W WO2018118346A1 WO 2018118346 A1 WO2018118346 A1 WO 2018118346A1 US 2017063381 W US2017063381 W US 2017063381W WO 2018118346 A1 WO2018118346 A1 WO 2018118346A1
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WO
WIPO (PCT)
Prior art keywords
iso
paraffins
gasoline
butane
gasoline fraction
Prior art date
Application number
PCT/US2017/063381
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English (en)
Inventor
Kun Wang
Original Assignee
Exxonmobil Research And Engineering Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US15/388,030 external-priority patent/US9637424B1/en
Application filed by Exxonmobil Research And Engineering Company filed Critical Exxonmobil Research And Engineering Company
Priority to CA3045631A priority Critical patent/CA3045631A1/fr
Priority to EP17812205.7A priority patent/EP3559167A1/fr
Publication of WO2018118346A1 publication Critical patent/WO2018118346A1/fr

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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
    • C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
    • 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
    • C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • 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
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/06—Liquid carbonaceous fuels essentially based on blends of hydrocarbons for spark ignition
    • 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
    • C10G2300/1081—Alkanes
    • 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
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/305—Octane number, e.g. motor octane number [MON], research octane number [RON]
    • 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 to upgrade light paraffins, preferably C2-C5, to high-octane gasoline.
  • the process is particularly applicable to the upgrading of iso-paraffins, which are abundantly found in Natural Gas Liquids (NGL) and tight oils (produced from shale or sandstone), as well as fractions from various refining and/or chemical streams.
  • NNL Natural Gas Liquids
  • tight oils produced from shale or sandstone
  • Profitable dispositions for ethane e.g., cracking to make ethylene
  • propane e.g., dehydrogenation to make propylene
  • Oxygenated high octane gasoline molecules such as ethanol have lower energy content (e.g., ethanol has ⁇ 82% of the volumetric energy content of gasoline) and can cause compatibility problems at high blending ratios.
  • there still remains a need for a process for producing higher octane, non-aromatic, non- oxygenated gasoline molecules especially a process using readily available feedstocks, such as light paraffins.
  • the process involves: (1) oxidation of iso-paraffins to alkyl hydroperoxides and alcohol; (2) conversion of the alkyl hydroperoxides and alcohol to dialkyl peroxides; and (3) radical-initiated coupling of iso-paraffins using the dialkyl peroxides as radical initiators, thereby forming products comprising gasoline range molecules. Fractionation of the product can then isolate the gasoline fraction, which is substantially a C8 fraction having a road octane [(RON + MON)/2] greater than 110.
  • the process involves (1) oxidizing iso- butane to t-butyl hydroperoxide and t-butyl alcohol; (2) converting the t-butyl hydroperoxide and t-butyl alcohol to di-t-butyl peroxide; and (3) radical -initiated coupling iso-butane using the di-t- butyl peroxide as a radical initiator to form products comprising gasoline range molecules.
  • This product is then fractionated to isolate the gasoline fraction, which is substantially a C8 fraction having a road octane [(RON + MON)/2] greater than 110.
  • a gasoline composition consisting primarily of C8 paraffins, primarily 2,2,3, 3-tetramethylbutane, and having a road octane number greater than 100 without the inclusion of aromatics or oxygenates.
  • the present invention relates to a process for making high octane gasoline from light paraffins.
  • the process of the present invention involves three primary steps: (1) oxidizing one or more iso-paraffins to alkyl hydroperoxides and alcohol using air or oxygen; (2) converting the alkyl hydroperoxides and alcohol to dialkyl peroxide; and (3) radical-initiated coupling the iso- paraffin using the dialkyl peroxide as a radical initiator to form products comprising gasoline range molecules. This products are then fractionated to isolate the gasoline fraction having a road octane number [(RON + MON)/2] greater than 110.
  • the iso-paraffin feedstock is iso- butane.
  • the process proceeds as described generally above: (1) oxidizing the iso-butane to t-butyl hydroperoxide and t-butyl alcohol using air or oxygen; (2) converting the t-butyl hydroperoxide and t-butyl alcohol to di-t-butyl peroxide; and (3) radical-initated coupling of iso-butane using the di-t-butyl peroxide as a radical initiator to form products comprising gasoline range molecules.
  • This products are then fractionated to isolate the gasoline fraction, which is a substantially C8 fraction having a road octane [(RON + MON)/2] greater than 1 10.
  • Equation 1 ⁇ " OH *
  • Equations 1-3 The net reaction of Equations 1-3 is oxygen (air) and iso-butane yielding heavier (C8) hydrocarbons comprising high octane gasoline, as well as water and t-butyl alcohol.
  • Step 3 is highly selective to 2,2,3, 3-tetramethylbutane (road octane number of -127), thus creating an overall C8 fraction having exceptionally high octane.
  • the resulting alcohol can be used as high octane blend stock for gasoline, e.g., t-butyl alcohol (road octane of about 96) from iso-butane, or 2-methyl-2-butanol (road octane of about 90) from iso-pentane.
  • t-butyl alcohol road octane of about 96
  • 2-methyl-2-butanol road octane of about 90
  • the alcohols can be converted via dehydration to olefins as chemical products (e.g., iso-butylene), oligomerized or alkylated to gasoline and/or diesel range fuels, or etherified with an alcohol such as methanol or ethanol making ether as a gasoline blend (e.g., MTBE or ETBE from iso-butane).
  • chemical products e.g., iso-butylene
  • oligomerized or alkylated to gasoline and/or diesel range fuels e.g., oligomerized or alkylated to gasoline and/or diesel range fuels
  • etherified with an alcohol such as methanol or ethanol making ether as a gasoline blend (e.g., MTBE or ETBE from iso-butane).
  • Steps 1 and 2 have been previously described with respect to mixed paraffinic feedstocks in applicant' s co-pending application, U. S. Publ. App. No. 2016/0168048, incorporated by reference herein in its entirety.
  • U.S. Publ. App. No. 2016/0168048 describes a process to convert light paraffins to heavier hydrocarbons generally, for example, distillates and lubricant base stocks, using coupling chemistry analogous to Steps 1-3 described above.
  • 2016/0168048 is directed to mixed paraffinic feed to create distillates and lubricant base stocks, the present invention utilizes analogous coupling chemistry to create a tailored paraffinic hydrocarbon fluid utilizing iso-paraffinic feedstock.
  • U.S. Publ. App. No. 2016/0168048 further discloses upgrading raw refinery feeds, such as natural gas liquids, liquid petroleum gas, and refinery light gas such as light virgin naphtha (LVN) or light catalytic naphtha (LCN), using coupling chemistry.
  • LNN light virgin naphtha
  • LPN light catalytic naphtha
  • Iso-butane oxidation in Step 1 is well-established commercially for making t-butyl hydroperoxide (TBHP) for propylene oxide manufacture, with variants of the process also described, for example, in U.S. Pat. No. 2,845,461; U.S. Pat. No. 3,478,108; U.S. Pat. No. 4,408,081 and U.S. Pat. No. 5, 149,885.
  • EP 0567336 and U.S. Pat. No. 5,162,593 disclose co- production of TBHP and t-butyl alcohol (TBA).
  • TBA is another reactant used in Step 2 of the present invention, the present inventive process scheme utilizes Step 1 as a practical source of these two reactants.
  • Air ⁇ 21% oxygen
  • a mixture of nitrogen and oxygen containing 2-20 vol% oxygen, or pure oxygen can be used for the oxidation, as long as the oxygen-to-hydrocarbon vapor ratio is kept outside the explosive regime.
  • air is used as the source of oxygen.
  • Typical oxidation conditions for Step 1 of the present invention are: 110-150 °C (preferably 130 to 140 °C, at a pressure of about 300-800 psig (preferably about 450-550 psig), with a residence time of 2- 24 hours (preferably 6-8 h), to give a targeted conversion of 15%-70% (preferably 30-50%).
  • Selectivity to TBHP of 50-80% and to TBA of 20-50% is typical.
  • Step 2 the conversion of the TBHP and TBA to di-t-butyl peroxide (DTBP) is performed using an acid catalyst.
  • DTBP di-t-butyl peroxide
  • U.S. Pat. No. 5,288,919 describes the use of an inorganic heteropoly and/or isopoly acid catalyst (such as for the reaction of TBA with TBHP.
  • the conjoint production of DTBP and TBA from TBHP is also described in U.S. Pat. No. 5,345,009.
  • a preferred configuration for the present invention uses reactive distillation where product water is continuously removed as overhead by-product.
  • Typical reaction temperature is in the range of 50 - 200 °C, preferably 60 - 150 °C, more preferably 80-120 °C.
  • the TBHP to TBA mole ratio is in the range of 0.5 - 2, preferably 0.8 - 1.5, more preferably 0.9 - 1.1.
  • the reaction can be performed with or without a solvent. Suitable solvents comprise hydrocarbons having a carbon number greater than 3, such as paraffins, naphthenes, or aromatics. Conveniently, the unreated iso- butane from Step 1 can be used as solvent for Step 2. Pressure for the reaction is held at appropriate ranges to ensure the reaction occurs substantially in the liquid phase, for example, 0 - 300 psig, preferably 5 - 100 psig, more preferably 15 - 50 psig.
  • An acid catalyst such as AmberlystTM resin, NafionTM resin, aluminosilicates, acidic clay, zeolites (natural or synthetic), silicoaluminophosphates (SAPO), heteropolyacids, acidic oxides such as tungsten oxide on zirconia, molybdenum oxide on zirconia, sulfuated zirconia, liquid acids such sulfuric acid, or acidic ionic liquids may be used in Step 2/Equation 2 to promote the conversion of TBHP and TBA into DTBP.
  • Step 3/Equation 3 DTBP is introduced to a coupling reactor to initiate free radical coupling of iso-butane feed.
  • Typical reaction conditions for Step 3 of the present invention are: 100-170 °C (preferably about 145-155 °C), with pressure maintained to ensure that iso-butane stays in the liquid or supercritical phase, typically 700-1500 psig (preferably about 850-950 psig). Residence time is normally in the range of 2-24 hours (preferably 4-16 hours).
  • the molar ratio of DTBP to iso-butane to be coupled is in the range of about 0.01-100, preferably in the range of about 0.05-10, and more preferably in the range of 0.1-2. Complete conversion of DTBP is normally achieved in this step.
  • Step 3 the mixed products are then fractionated to remove unreacted iso- butane and TBA, byproduct acetone, and to separate high octane gasoline as well as jet-range hydrocarbons.
  • This example illustrates the general procedure for coupling iso-butane using DTBP to form high octane gasoline.
  • a 300 cc autoclave the following were loaded: 100 cc (59.5 g) of iso-butane (Airgas, instrument grade) and 56 g of DTBP (trade name Luperox DI from Aldrich Chemicals, 98%).
  • the autoclave was sealed, connected to a gas manifold, and pressurized with 600 psig nitrogen.
  • the reactor content heated under stirring (500 rpm) at a rate of 2 °C/min to 150 °C and held for 4 hours. The heat was turned off and the autoclave allowed to cool down to room temperature.
  • a gasoline composition comprising 2,2,3,3- tetramethylbutane and having road octane [(RON+MON)/2] greater than 110 can be produced from certain teachings of the present invention.
  • This road octane number is achieved without the addition of aromatics or oxygenates.
  • key variables including reaction temperature, molar ratio of DTBP to iso-butane, and residence time, can be adjusted to optimize and tailor the gasoline fraction for specific applications.
  • Embodiment 1 A process for the conversion of iso-paraffins to gasoline-range molecules, comprising oxidizing a first feed stream comprising one or more iso-paraffins to form alkyl hydroperoxides and alcohol, catalytically converting the alkyl hydroperoxides and alcohols to dialkyl peroxides, and coupling a second feed stream comprising one or more iso-paraffins using the dialkyl peroxides as a radical initiator to create gasoline-range molecules.
  • Embodiment 2 A process according to embodiment 1, further comprising fractionating the gasoline-range molecules to isolate a desired gasoline fraction.
  • Embodiment 3 A process according to any of the previous embodiments, wherein the one or more iso-paraffins in the first feed stream and in the second feed stream is independently selected from iso-butane, iso-pentane, and mixtures thereof.
  • Embodiment 4 A process according to any of the previous embodiments, wherein the one or more iso-paraffins in the first feed stream is iso-butane.
  • Embodiment 5. A process according to any of the previous embodiments, wherein the one or more iso-paraffins in the second feed stream is iso-butane.
  • Embodiment 6 A process for the conversion of iso-butane to paraffinic gasoline-range molecules, comprising, oxidizing iso-butane to form t-butyl hydroperoxide and t-butyl alcohol, catalytically converting the t-butyl hydroperoxide and the t-butyl alcohol to di-t-butyl peroxide, and coupling iso-butane using the di-t-butyl peroxide as a radical initiator to form gasoline-range molecules.
  • Embodiment 7 A process according to embodiment 6, further comprising fractionating the gasoline-range molecules to isolate a desired gasoline fraction.
  • Embodiment 8 A process according to any of the previous embodiments, wherein the desired gasoline fraction comprises substantially all C8 paraffins.
  • Embodiment 9 A process according to any of the previous embodiments, wherein the desired gasoline fraction comprises substantially all C8 and C9 paraffins.
  • Embodiment 10 A process according to any of the previous embodiments, wherein the desired gasoline fraction has a road octane number [(RON+MON)/2)] greater than about 110.
  • Embodiment 11 A process according to any of the previous embodiments, wherein the desired gasoline fraction has a road octane number greater than about 111.
  • Embodiment 12 A process according to any of the previous embodiments, wherein the desired gasoline fraction has a road octane number greater than about 112.
  • Embodiment 13 A process according to any of the previous embodiments, wherein the desired gasoline fraction comprises substantially all C8 paraffins.
  • Embodiment 14 A process according to any of the previous embodiments, wherein the desired gasoline fraction comprises substantially all C8 and C9 paraffins.
  • Embodiment 15 A process according to any of the previous embodiments, wherein the desired gasoline fraction comprises 2,2,3,3-tetramethylbutane.
  • Embodiment 16 A process according to any of the previous embodiments, wherein the desired gasoline fraction comprises 2-95 vol% 2,2,3,3-tetramethylbutane.
  • Embodiment 17 A process according to any of the previous embodiments, wherein the desired gasoline fractrion comprises 5-90 vol% 2,2,3,3-tetramethylbutane.
  • Embodiment 18 A process according to any of the previous embodiments, wherein the desired gasoline fractrion comprises 50-80 vol% 2,2,3,3-tetramethylbutane.
  • Embodiment 19 A high octane gasoline composition, comprising a desired gasoline fraction prepared according to any of the previous embodiments. [0039] Therefore, the present invention is well adapted to attain the ends and advantages mentioned as well as those that are inherent therein.
  • the particular embodiments disclosed above are illustrative only, as the present invention may be modified and practiced in different but equivalent manners apparent to those skilled in the art having the benefit of the teachings therein. It is therefore evident that the particular embodiments disclosed above may be altered or modified and all such variations are considered within the scope and sprit of the present invention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

L'invention concerne un procédé de conversion de paraffines légères en une composition d'essence à indice d'octane élevé. Le procédé comprend : (1) l'oxydation d'iso-paraffines en hydroperoxydes d'alkyle et en alcool ; (2) la conversion des hydroperoxydes d'alkyle et de l'alcool en peroxydes de dialkyle ; et (3) le couplage radicalaire d'iso-paraffines à l'aide des peroxydes de dialkyle utilisés comme initiateurs de radicaux, ce qui permet de former des molécules de gamme essence. Le fractionnement des molécules de gamme essence peut ensuite être utilisé pour isoler des fractions d'essence à indice d'octane élevé présentant un indice d'octane route [(IOR + IOM)/2] supérieur à 110.
PCT/US2017/063381 2016-12-22 2017-11-28 Procédé permettant de fabriquer de l'essence à indice d'octane élevé WO2018118346A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA3045631A CA3045631A1 (fr) 2016-12-22 2017-11-28 Procede permettant de fabriquer de l'essence a indice d'octane eleve
EP17812205.7A EP3559167A1 (fr) 2016-12-22 2017-11-28 Procédé permettant de fabriquer de l'essence à indice d'octane élevé

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15/388,030 US9637424B1 (en) 2014-12-16 2016-12-22 High octane gasoline and process for making same
US15/388,030 2016-12-22

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Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2845461A (en) 1956-04-12 1958-07-29 Shell Dev Non-catalytic liquid phase isobutane oxidation
US3478108A (en) 1966-02-21 1969-11-11 Atlantic Richfield Co Isobutane oxidation
US4408081A (en) 1981-10-05 1983-10-04 Shell Oil Company Process for oxidation of isobutane
US4618737A (en) * 1985-12-13 1986-10-21 Mobil Oil Corporation Peroxide-induced polymerization of MOGD liquids to high viscosity lubes
US5149885A (en) 1992-02-20 1992-09-22 Arco Chemical Technology, L.P. Oxidation of isobutane to tertiary butyl hydroperoxide
US5162593A (en) 1991-11-25 1992-11-10 Arco Chemical Technology, L.P. Tertiary butyl alcohol preparation
EP0567336A1 (fr) 1992-04-22 1993-10-27 ARCO Chemical Technology, L.P. Oxydation d'isobutane en hydroperoxyde de butyle tertiaire
US5288919A (en) 1993-05-13 1994-02-22 Arco Chemical Technology, L.P. Preparation of dialkyl peroxides
US5345009A (en) 1993-11-12 1994-09-06 Texaco Chemical Company Conjoint production of ditertiary butyl peroxide and tertiary butyl alcohol from tertiary butyl hydroperoxide
US7034189B1 (en) * 1995-12-05 2006-04-25 Redox Technologies Inc. Preparation of dialkyl peroxides
US20080253936A1 (en) * 2007-04-16 2008-10-16 Ramin Abhari Process for producing synthetic petroleum jelly
US20160168048A1 (en) 2014-12-16 2016-06-16 Exxonmobil Research And Engineering Company Upgrading paraffins to distillates and lubricant basestocks

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2845461A (en) 1956-04-12 1958-07-29 Shell Dev Non-catalytic liquid phase isobutane oxidation
US3478108A (en) 1966-02-21 1969-11-11 Atlantic Richfield Co Isobutane oxidation
US4408081A (en) 1981-10-05 1983-10-04 Shell Oil Company Process for oxidation of isobutane
US4408081B1 (fr) 1981-10-05 1986-05-13
US4618737A (en) * 1985-12-13 1986-10-21 Mobil Oil Corporation Peroxide-induced polymerization of MOGD liquids to high viscosity lubes
US5162593A (en) 1991-11-25 1992-11-10 Arco Chemical Technology, L.P. Tertiary butyl alcohol preparation
US5149885A (en) 1992-02-20 1992-09-22 Arco Chemical Technology, L.P. Oxidation of isobutane to tertiary butyl hydroperoxide
EP0567336A1 (fr) 1992-04-22 1993-10-27 ARCO Chemical Technology, L.P. Oxydation d'isobutane en hydroperoxyde de butyle tertiaire
US5288919A (en) 1993-05-13 1994-02-22 Arco Chemical Technology, L.P. Preparation of dialkyl peroxides
US5345009A (en) 1993-11-12 1994-09-06 Texaco Chemical Company Conjoint production of ditertiary butyl peroxide and tertiary butyl alcohol from tertiary butyl hydroperoxide
US7034189B1 (en) * 1995-12-05 2006-04-25 Redox Technologies Inc. Preparation of dialkyl peroxides
US20080253936A1 (en) * 2007-04-16 2008-10-16 Ramin Abhari Process for producing synthetic petroleum jelly
US20160168048A1 (en) 2014-12-16 2016-06-16 Exxonmobil Research And Engineering Company Upgrading paraffins to distillates and lubricant basestocks

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CA3045631A1 (fr) 2018-06-28

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