WO2013170280A1 - Conversion of alcohols to distillates - Google Patents

Conversion of alcohols to distillates Download PDF

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Publication number
WO2013170280A1
WO2013170280A1 PCT/ZA2013/000035 ZA2013000035W WO2013170280A1 WO 2013170280 A1 WO2013170280 A1 WO 2013170280A1 ZA 2013000035 W ZA2013000035 W ZA 2013000035W WO 2013170280 A1 WO2013170280 A1 WO 2013170280A1
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Prior art keywords
alcohols
feed
total
distillate
catalyst
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PCT/ZA2013/000035
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French (fr)
Inventor
Masikana Millan Mdleleni
Cyril David Knottenbelt
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The Petroleum Oil And Gas Corporation Of South Africa (Pty) Ltd
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Publication date
Application filed by The Petroleum Oil And Gas Corporation Of South Africa (Pty) Ltd filed Critical The Petroleum Oil And Gas Corporation Of South Africa (Pty) Ltd
Priority to AP2014008121A priority Critical patent/AP2014008121A0/en
Publication of WO2013170280A1 publication Critical patent/WO2013170280A1/en
Priority to ZA2014/08950A priority patent/ZA201408950B/en

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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
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
    • C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4012—Pressure
    • 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
    • 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
    • C10G2400/08—Jet fuel
    • 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
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

Definitions

  • This invention relates to the use of alcohols, having a carbon range C1 to C5, as feedstock in a process for the production of synthetically derived distillates.
  • it relates to mixed alcohols of varying chain length or blends thereof with light olefins.
  • the inventor is aware of the catalytic Conversion of Olefins to Distillates (COD) process which entails conversion of light olefins to longer chain distillates, over a zeolite type catalyst as described in PCT/ZA06/00029.
  • the zeolyte type catalysts include ZSM-5 catalysts and a catalyst known a COD-9 supplied by Sud Chemie, which is similar to the ZSM-5 catalyst and which contain shape selective pores to prevent the formation of certain bulky structures. These catalysts simultaneously catalyse oligomerization and cracking and have a good life cycle.
  • the synthesis of such a zeolite type catalyst is cited in South African patent no. ZA 89/8669.
  • Light olefins are typically used as feedstocks in the COD process, and predominantlycan ⁇ be prioritizederived-from coal r gas-or-biomass by-the Fiseher-Tropsch process as ⁇ in the case of the PetroSA GTL Refinery commercial process where it is derived from gas.
  • the Fischer Tropsch process has low selectivity towards lower olefins necessitating more than one synthetic step to produce these olefins and complicating the processing operation. Additional steps include cracking or the methanol to olefins (MTO) process.
  • a process for producing synthetically derived distillates using alcohols, in the carbon range C2 to C5, as feedstock includes the step of:
  • zeolite type catalyst selected from a ZSM-5 or COD-9, or similar, catalyst at pressures of greater than 40 barg.
  • the alcohols may comprise of a mixture of alcohols of varying chain lengths and may be branched.
  • the alcohols may be dehydrated to their corresponding olefins, reaction water and some organic acids formed as by-products.
  • the dehydration reaction may be catalysed by a zeolite type catalyst.
  • the zeolite type catalyst may be a COD-9 catalyst or a ZSM-5 catalyst.
  • Alumina may also be used to dehydrate alcohols. Dehydrated alcohols may_be_combined with— olefins as feedstocks in a COD process.
  • the same catalyst used to catalyse dehydration of the alcohols may be used to catalyse the conversion of the resulting olefin products to distillates. If alumina was used to dehydrate alcohols or other methods were employed, a zeolite type of catalyst may be introduced after dehydration to catalyse the conversion of the resulting olefin products to distillates.
  • the dehydration products may be converted to distillates during a series of reactions including oligomerisation, cyclilisation and isomerisation to form a distillate mixture comprising mainly of branched and straight chain olefins, branched and straight chain paraffin's, branched and straight chain cyclo-olefins and aromatics. Distillates produced by this process may be hydrogenated and fractionated into final products such as gasoline, kerosene and diesel using commercial refinery processes and catalysts.
  • the test was performed in a microscale fixed bed reactor that was charged with 10g of COD-9 catalyst as supplied by Sud Chemie.
  • the microscale fixed bed reactor configuration is shown in Figure 1.
  • Liquid feeds to were delivered to the reactor by HPLC pumps (P1 , P2 and P3).
  • Pressure to the reactor was maintained by means of a backpressure regulator (BPR-1).
  • BPR-1 backpressure regulator
  • the product was collect in a catchpot (CP-1) downstream of the backpressure regulator.
  • the reaction products comprised of both a hydrocarbon or distillate phase and an aqueous phase, these were collected in the Liquid Catchpot (CP-1) as illustrated ⁇ in ⁇ gure L
  • GC gas chromatography
  • Gas chromatography analysis was performed on GC's equipped with split/splitless injectors and Flame lonisation Detectors.
  • the GC used to analyse the hydrocarbon phase were fitted with a BP-1 PONA type column, while the GC used for the aqueous phase was separated on a Carbowax 400 column.
  • the reactor was loaded with 10g catalyst in the following configuration as illustrated in Figure 1.
  • the reactor was operated at a pressure of 45 barg and the reaction temperature was 190°C.
  • Light olefins feed comprising of C5 to C6 (C5 C6) carbon chain lengths originating from a High Temperature Fischer Tropsch plant located in Mossel Bay were used as the base case feed.
  • the Bromine Number of the Cs/C 6 feed used for the study was 91 g Br/100g sample.
  • the alcohol feed comprised of a blend in a 50:50 ratio of Ethanol to C5/C6 olefin feed.
  • Distillate as well as reaction water was produced; the volume of the water phase was estimated at about 20% relative to the distillate phase.
  • the distillate produced quality as analysed by gas chromatography is given in Table .
  • the reaction water was found to contain 39% of unconverted Ethanol and 45.96% where Non Acid Chemicals.
  • the test was performed in the same microscale fixed bed reactor that is described in Example 1 and shown in Figure 1.
  • the reactor was charged with 10g of COD-9 catalyst as supplied by Sud Chemie.
  • Example 2 Since all the Ethanol in the case of Example 1 was not converted it was decided to run the test with a mixed alcohol feed at an elevated temperature 275 °C to see if better conversions were possible.
  • the feed for Example 2 was Mosstanol L, a light alcohol product of the Petroleum Oil and Gas Corporation of South Africa.
  • Mosstanol comprises of a mixture of 2 alcohols; 60 % v/v Ethanol and 40% Isopropyl alcohol.
  • reaction water phase from this run was analysed and found to contain 0.633 mass % of unconverted ethanol and 0.006 mass% IPA.
  • the total non acid chemical portion in the reaction water was 1.426 % mass.
  • the resultant olefinic distillate product as produced in Examples 1 and 2 can be hydrotreated at moderate hydrotreating conditions followed by fractionation to form high quality gasoline, kerosene and diesel products as per the PetroSA commercial process.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (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)

Abstract

The invention provides a process for producing synthetically derived distillates using alcohols, in the carbon range C2 to C5, as feedstock. The process includes the step of contacting the feed with a COD-9 zeolyte catalyst at pressures of greater than 40 barg.

Description

Conversion of Alcohols to Distillates
Technical field of the invention
This invention relates to the use of alcohols, having a carbon range C1 to C5, as feedstock in a process for the production of synthetically derived distillates. In particular it relates to mixed alcohols of varying chain length or blends thereof with light olefins.
Background to the invention
The inventor is aware of the catalytic Conversion of Olefins to Distillates (COD) process which entails conversion of light olefins to longer chain distillates, over a zeolite type catalyst as described in PCT/ZA06/00029. The zeolyte type catalysts include ZSM-5 catalysts and a catalyst known a COD-9 supplied by Sud Chemie, which is similar to the ZSM-5 catalyst and which contain shape selective pores to prevent the formation of certain bulky structures. These catalysts simultaneously catalyse oligomerization and cracking and have a good life cycle. The synthesis of such a zeolite type catalyst is cited in South African patent no. ZA 89/8669.
Light olefins are typically used as feedstocks in the COD process, and „can^be„derived-from coalrgas-or-biomass by-the Fiseher-Tropsch process as~ in the case of the PetroSA GTL Refinery commercial process where it is derived from gas. However, the Fischer Tropsch process has low selectivity towards lower olefins necessitating more than one synthetic step to produce these olefins and complicating the processing operation. Additional steps include cracking or the methanol to olefins (MTO) process.
Alternative feedstocks for the COD process are needed to simplify processing operations, meet future fuel requirements and to diversify the energy pool in an environmentally friendly way. Alcohol based feeds are proposed due to their availability and ease of transport. In particular bio- ethanol derived from biomass can be used to produce bio-distillates which in turn could be refined to produce bio-gasoline, bio-kerosene and bio-diesel.
It is an object of this invention to use alcohols, preferably mixed alcohols of varying chain length, as pure feeds or co-feeds with olefins, for the typical COD process.
General description of the invention
According to a first aspect of the invention, there is provided a process for producing synthetically derived distillates using alcohols, in the carbon range C2 to C5, as feedstock and includes the step of:
contacting the feed or combinations thereof with a zeolite type catalyst selected from a ZSM-5 or COD-9, or similar, catalyst at pressures of greater than 40 barg.
The alcohols may comprise of a mixture of alcohols of varying chain lengths and may be branched.
The alcohols may be dehydrated to their corresponding olefins, reaction water and some organic acids formed as by-products. The dehydration reaction may be catalysed by a zeolite type catalyst. The zeolite type catalyst may be a COD-9 catalyst or a ZSM-5 catalyst. Alumina may also be used to dehydrate alcohols. Dehydrated alcohols may_be_combined with— olefins as feedstocks in a COD process.
The same catalyst used to catalyse dehydration of the alcohols may be used to catalyse the conversion of the resulting olefin products to distillates. If alumina was used to dehydrate alcohols or other methods were employed, a zeolite type of catalyst may be introduced after dehydration to catalyse the conversion of the resulting olefin products to distillates. The dehydration products may be converted to distillates during a series of reactions including oligomerisation, cyclilisation and isomerisation to form a distillate mixture comprising mainly of branched and straight chain olefins, branched and straight chain paraffin's, branched and straight chain cyclo-olefins and aromatics. Distillates produced by this process may be hydrogenated and fractionated into final products such as gasoline, kerosene and diesel using commercial refinery processes and catalysts.
Detailed description of the invention
The invention is now described by way of the following examples with reference to figures wherein Figure 1 shows a process flow description and Figure 2 shows a reactor loading diagram.
EXAMPLE 1
The test was performed in a microscale fixed bed reactor that was charged with 10g of COD-9 catalyst as supplied by Sud Chemie. The microscale fixed bed reactor configuration is shown in Figure 1. Liquid feeds to were delivered to the reactor by HPLC pumps (P1 , P2 and P3). Pressure to the reactor was maintained by means of a backpressure regulator (BPR-1). The product was collect in a catchpot (CP-1) downstream of the backpressure regulator.
The reaction products comprised of both a hydrocarbon or distillate phase and an aqueous phase, these were collected in the Liquid Catchpot (CP-1) as illustrated^ in^gure L The LproducLphases-were-separated-and— analysed by gas chromatography (GC). Gas chromatography analysis was performed on GC's equipped with split/splitless injectors and Flame lonisation Detectors. The GC used to analyse the hydrocarbon phase were fitted with a BP-1 PONA type column, while the GC used for the aqueous phase was separated on a Carbowax 400 column.
The reactor was loaded with 10g catalyst in the following configuration as illustrated in Figure 1. The reactor was operated at a pressure of 45 barg and the reaction temperature was 190°C. Light olefins feed comprising of C5 to C6 (C5 C6) carbon chain lengths originating from a High Temperature Fischer Tropsch plant located in Mossel Bay were used as the base case feed. The Bromine Number of the Cs/C6 feed used for the study was 91 g Br/100g sample. After running the base feed for 24 hours the feed was switched to an alcohol containing feed. The alcohol feed comprised of a blend in a 50:50 ratio of Ethanol to C5/C6 olefin feed. Distillate as well as reaction water was produced; the volume of the water phase was estimated at about 20% relative to the distillate phase. The distillate produced quality as analysed by gas chromatography is given in Table .
Table 1 Distillate Composition as produced for the C5/C6:Ethanol :: 50:50 feed
Figure imgf000006_0001
C7 total 20.88
C8 total 20.12
C9 total 6.85
C10 total 3.41
C11 total 2.02
C12 total 1.15
C13 total 0.60
C14 total 0.38
C15 total 0.11
C16 + total 0.02
TOTAL normalised 100.00
The reaction water was found to contain 39% of unconverted Ethanol and 45.96% where Non Acid Chemicals.
For the distillate feed (base case) at a reaction temperature of 190°C a yield of 38.1 % v/v of C10 Plus distillate was achieved. After switching to the C5/C6 distillate-ethanol (50:50) blend feed the C10 Plus distillate yield dropped to 7.7% while the C7 distillate fraction increased substantially from 0.3 to 55.5% v/v.
The aromatic content for the Cs/C6 distillate-ethanol blend increased from 3.1 to 3.5 % m/m over the base case distillate feed (C5/C6). These results are summarised in Table 2.
Table 2 Aromatic and Distillate Yield Results
Figure imgf000007_0001
EXAMPLE 2
The test was performed in the same microscale fixed bed reactor that is described in Example 1 and shown in Figure 1. The reactor was charged with 10g of COD-9 catalyst as supplied by Sud Chemie.
Since all the Ethanol in the case of Example 1 was not converted it was decided to run the test with a mixed alcohol feed at an elevated temperature 275 °C to see if better conversions were possible. The feed for Example 2 was Mosstanol L, a light alcohol product of the Petroleum Oil and Gas Corporation of South Africa. Mosstanol comprises of a mixture of 2 alcohols; 60 % v/v Ethanol and 40% Isopropyl alcohol.
Near complete conversion was noted for the Mosstanol L (Ethanol : Iso-propyl Alcohol :: 60: 40) feed at a temperature of 275 °C. The volume of the distillate fraction boiling above C10 was 37.6%, this relates to a yield of 22.5 after correction to account for unconverted alcohols extracted in the reaction water phase. The distillate quality as tested by GC is given in Table 3.
Table 3 Distillate Composition as produced for the Mosstanol L feed
Figure imgf000008_0001
n-pentane 2.17
2-methyl-i ,3-butadiene 0.00
trans-2-pentene 0.07
cis-2-pentene 0.03
2-methyl-2-butene 0.30
trans-1.3-pentadiene 0.00
C5 total .73
C6 total 11.25
C7 total 1 1.09
C8 total 9.55
C9 total 12.05
C10 total 15.81
C11 total 12.68
C12 total 6.19
C13 total 1.67
C14 total 0.79
C15 total 0.33
C16 + total 0.11
TOTAL normalised 100.00
Near complete conversion of the oxygenated feed was achieved with the distillate phase being free of oxygenates. The reaction water phase from this run was analysed and found to contain 0.633 mass % of unconverted ethanol and 0.006 mass% IPA. The total non acid chemical portion in the reaction water was 1.426 % mass.
Table 4 Aromatic and Distillate Yield Results
Figure imgf000009_0001
Higher temperatures (275°C) favoured oxygenate conversion, the proposed reaction mechanism being via the dehydration alcohols to olefins route.
H \ /
H-C- C-OH C=C H-OH
/ \
For the runs where oxygenates were used as feed reaction water was produced that contained organic acids. The reaction water phase was tested for organic acid content and found to contain a total of 14,900 ppm m/m organic acids of which acetic acid (11 ,384 ppm) and propionic acid (2,679 ppm) were the dominant species. The composition of organic acids and Non- acid chemicals (oxygenates) and are given in Tables 5 and 6 respectively.
Table 5 Reaction Water Composition - Organic Acids
Figure imgf000010_0001
Table 6 Reaction Water Composition
Figure imgf000010_0002
After processing the alcohol feeds the reactor was switched back to the C5/C6 feed and the distillate conversion thereof measured. The C10 Plus distillate yield was 14,4 %, this is lower than the 38.1 % observed after Day-1 on-line for the same feed. Higher conversion was regained by increasing the reactor temperature.
Table 7 Aromatic and Distillate Yield Results
Figure imgf000011_0001
The resultant olefinic distillate product as produced in Examples 1 and 2 can be hydrotreated at moderate hydrotreating conditions followed by fractionation to form high quality gasoline, kerosene and diesel products as per the PetroSA commercial process.
EXAMPLE 3
Further testing was performed on a microscale reactor coupled to an on-line GC whereby a feed comprising of Propylene : C5 to C6 oleffinic feed : Ethanol :: 25 : 37.5% : 37.5% was fed to the micro-reactor. The latter feed was processed at a pressure of 55 barg and a temperature of 265 °C over COD-9 catalyst. The carbon 10 plus distillate yield was 20 %, increasing the temperature to 300 °C increased the distillate yield accordingly to 40 %.
It shall be understood that the examples are provided for illustrating the invention further and to assist a person skilled in the art with understanding the invention and are not meant to be construed as unduly limiting the reasonable scope of the invention.

Claims

Claims
1. A process for producing synthetically derived distillates using alcohols, in the carbon range C2 to C5, as feedstock including the step of: contacting the feed or combinations thereof with a zeolite type catalyst selected from a ZSM-5 or COD-9, or similar, catalyst at pressures of greater than 40 barg.
2. The process as claimed in claim 1 , wherein the alcohols comprise of a mixture of alcohols of varying chain length.
3. The process as claimed in Claim 1 or Claim 2, wherein the alcohol feedstock includes light olefins as co-feed.
4. The process as claimed in any one of claims 1 to 3 wherein the zeolite catalyst is introduced after dehydration of the alcohols.
5. The process as claimed in claim 4, wherein alumina is used to first dehydrate the alcohols.
6. A process for producing synthetically derived distillates using alcohols substantially as described herein with reference the accompanying drawings.
PCT/ZA2013/000035 2012-05-11 2013-05-09 Conversion of alcohols to distillates WO2013170280A1 (en)

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0099690A2 (en) * 1982-07-20 1984-02-01 Mobil Oil Corporation Process for the conversion of alcohols and oxygenates into hydrocarbons
US4547601A (en) * 1980-12-23 1985-10-15 Mobil Oil Corporation Conversion of Fischer-Tropsch oxygenates to middle distillate
ZA898669B (en) 1988-11-15 1990-08-29 Cotec Patrade Pty Ltd A catalyst based on crystalline alumino-silicates
WO2006069407A2 (en) * 2004-12-23 2006-06-29 The Petroleum Oil And Gas Corporation Of South Africa (Pty) Ltd Production of diesel
WO2008071291A2 (en) * 2006-12-13 2008-06-19 Haldor Topsøe A/S Process for the synthesis of hydrocarbon constituents of gasoline
FR2951163A1 (en) * 2009-10-13 2011-04-15 Total Raffinage Marketing PROCESS FOR PRODUCTION OF DISTILLATE BY CATALYTIC OLIGOMERIZATION OF OLEFINS IN THE PRESENCE OF OXYGEN COMPOUNDS
FR2951161A1 (en) * 2009-10-13 2011-04-15 Total Raffinage Marketing PROCESS FOR PRODUCING DISTILLATE FROM A HYDROCARBONATED LOAD COMPRISING ALCOHOL CONDENSATION
US7994377B2 (en) * 2006-05-30 2011-08-09 IFP Energies Nouvelles Method of converting ethanol to base stock for diesel fuel
WO2011138520A2 (en) * 2010-05-06 2011-11-10 IFP Energies Nouvelles Method for producing kerosene from bio-ethanol

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4547601A (en) * 1980-12-23 1985-10-15 Mobil Oil Corporation Conversion of Fischer-Tropsch oxygenates to middle distillate
EP0099690A2 (en) * 1982-07-20 1984-02-01 Mobil Oil Corporation Process for the conversion of alcohols and oxygenates into hydrocarbons
ZA898669B (en) 1988-11-15 1990-08-29 Cotec Patrade Pty Ltd A catalyst based on crystalline alumino-silicates
WO2006069407A2 (en) * 2004-12-23 2006-06-29 The Petroleum Oil And Gas Corporation Of South Africa (Pty) Ltd Production of diesel
US7994377B2 (en) * 2006-05-30 2011-08-09 IFP Energies Nouvelles Method of converting ethanol to base stock for diesel fuel
WO2008071291A2 (en) * 2006-12-13 2008-06-19 Haldor Topsøe A/S Process for the synthesis of hydrocarbon constituents of gasoline
FR2951163A1 (en) * 2009-10-13 2011-04-15 Total Raffinage Marketing PROCESS FOR PRODUCTION OF DISTILLATE BY CATALYTIC OLIGOMERIZATION OF OLEFINS IN THE PRESENCE OF OXYGEN COMPOUNDS
FR2951161A1 (en) * 2009-10-13 2011-04-15 Total Raffinage Marketing PROCESS FOR PRODUCING DISTILLATE FROM A HYDROCARBONATED LOAD COMPRISING ALCOHOL CONDENSATION
WO2011138520A2 (en) * 2010-05-06 2011-11-10 IFP Energies Nouvelles Method for producing kerosene from bio-ethanol

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Title
CYRIL KNOTTENBELT: "Mossgas "gas-to-liquid" diesel fuels-an environmentally friendly option", CATALYSIS TODAY, vol. 71, no. 3-4, 1 January 2002 (2002-01-01), pages 437 - 445, XP055080271, ISSN: 0920-5861, DOI: 10.1016/S0920-5861(01)00471-0 *
TALUKDAR A K ET AL: "HZSM-5 catalysed conversion of aqueous ethanol to hydrocarbons", APPLIED CATALYSIS A: GENERAL, ELSEVIER SCIENCE, AMSTERDAM, NL, vol. 148, no. 2, 2 January 1997 (1997-01-02), pages 357 - 371, XP004337990, ISSN: 0926-860X, DOI: 10.1016/S0926-860X(96)00240-2 *

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