WO2008041038A1 - Manufacture of biodiesel fuel - Google Patents

Manufacture of biodiesel fuel Download PDF

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Publication number
WO2008041038A1
WO2008041038A1 PCT/GB2007/050614 GB2007050614W WO2008041038A1 WO 2008041038 A1 WO2008041038 A1 WO 2008041038A1 GB 2007050614 W GB2007050614 W GB 2007050614W WO 2008041038 A1 WO2008041038 A1 WO 2008041038A1
Authority
WO
WIPO (PCT)
Prior art keywords
glycerol
methanol
catalyst
oil
manufacture
Prior art date
Application number
PCT/GB2007/050614
Other languages
French (fr)
Inventor
Grimley Andrew
Original Assignee
Grimley Smith Associates Ltd
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
Application filed by Grimley Smith Associates Ltd filed Critical Grimley Smith Associates Ltd
Publication of WO2008041038A1 publication Critical patent/WO2008041038A1/en

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • 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
    • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • 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
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/60—Platinum group metals with zinc, cadmium or mercury
    • 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
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel
    • 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
    • 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 a method for the manufacture of biodiesel fuel from vegetable oils.
  • the production of biodiesel fuel oil from vegetable oils typically involves, amongst other stages, the base catalysed transesterification of the oil to form esters and glycerol.
  • the oils contains triglycerides - essentially a glycerine molecule with three long-chain fatty acids attached.
  • the triglyceride is reacted with alcohol, usually methanol, in the presence of a catalyst, usually a strong alkaline such as sodium hydroxide.
  • a catalyst usually a strong alkaline such as sodium hydroxide.
  • the methanol reacts with the fatty acids to produce methyl esters and crude glycerol.
  • the amount of glycerol produced as a by-product is about 1 tonne for every ten tonnes of biodiesel.
  • the UK Government has set a target of producing 20% of the nation's fuel from natural sources by the year 2020. If this were to be in the form of biodiesel, this would translate to 3.6 million tonnes of biodiesel and about 360,000 tonnes of glycerol.
  • the current world market for glycerol is in the region of 150,000 tonnes per year, so the waste glycerol from UK sources alone will be nearly 2.5 times the current world consumption. It is very unlikely that sufficient new uses will be found for glycerol to consume the anticipated production as a by-product.
  • Waste glycerol from the production of biodiesel is contaminated with fatty acids and other related materials, and would require purification before it could be sold for industrial use. Since the market demand is insufficient, this is not feasible for all waste glycerol.
  • Current ideas for disposal include burning and biological digestion. Glycerol has approximately 50% of the calorific value of fuel oil, and burning is therefore not an attractive option. Current disposal costs for waste glycerol are in the region of £30 per tonne. Summary of the Invention
  • a method for the manufacture of bio diesel fuel from vegetable oils comprising treating the oils with methanol and a base catalyst to cause esterification yielding methyl fatty acid esters and glycerol, separating the glycerol from the estehfied oil, treating the glycerol with a catalyst to yield methanol, and using the methanol produced in the esterification of further vegetable oil.
  • the glycerol is reacted with a catalyst in the presence of a reducing gas such as carbon monoxide or hydrogen.
  • the catalyst is suitably a mixed base metal oxide/precious metal. It is suitably presented in thin film form.
  • the metal oxide may be, for example, zinc oxide, and the precious metal is suitably palladium.
  • the catalyst is preferably operated at elevated tempera- tures, for example in the region of 300° C to 800° C, and so the glycerol will need to be in vapour form, but may need protection from thermal breakdown.
  • Pre-treatment of the glycerol may be required to remove contaminants which might adversely affect the catalytic reaction.
  • the methanol is typically produced by the reaction in vapour form and will therefore need to be condensed. Purification of the methanol may be needed before it can be used in the esterification process, for example to remove water.
  • glycerol is dropping in price and will continue to fall due to the glut of glycerol on the market from the production of bio diesel.
  • the drawing represents diagrammatically a process for the manufacture of biodiesel according to one embodiment of the invention.
  • vegetable oil for example produced by milling or pressing rape seed or similar oil-bearing seed, is stored in an oil feed tank 1.
  • oils from a range of different vegetable sources may be used, as well as recycled cooking oils.
  • the oil feed tank 1 supplies oil to a reactor 2, which is also supplied with methanol from a methanol feed tank 3, and with so- dium hydroxide solution from a base supply tank 4.
  • the esterified oil passes to a separation stage 5 where the glycerol is separated off for supply to a second vapour phase reactor 6.
  • the biodiesel oil is removed by line 7 for further treatment (not shown).
  • the reactor 2 will typically be a batch reactor. While the supply of sodium hydroxide and methanol are shown to be separate, in practice it may be desirable to mix the two before introduction into and mixing with the crude vegetable oil. A typical batch reaction might occupy 4 to 6 hours.
  • the reactor 6 contains the zinc oxide/palladium catalyst and is supplied with carbon monoxide from a supply vessel 8.
  • the methanol vapour is led to a condenser 9 and the liquid methanol passes to a purification/drying stage 10 before being delivered to the methanol feed tank 3.
  • the process will employ heat recovery to ensure energy efficiency.
  • the esterification reaction requires heat input to maintain a temperature of around 50 0 C
  • the catalytic reaction requires to be carried out at elevated temperatures in excess of 300 0 C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A method for the manufacture of biodiesel fuel from vegetable oils, com- prises treating the oils with methanol and a base catalyst to cause esterification yielding methyl fatty acid esters and glycerol, separating the glycerol from the esterified oil, treating the glycerol with a catalyst to yield methanol, and using the methanol produced in the esterification of further vegetable oil.

Description

MANUFACTURE OF BIODIESEL FUEL Field of the Invention
This invention relates to a method for the manufacture of biodiesel fuel from vegetable oils. Background to the Invention
The production of biodiesel fuel oil from vegetable oils typically involves, amongst other stages, the base catalysed transesterification of the oil to form esters and glycerol. The oils contains triglycerides - essentially a glycerine molecule with three long-chain fatty acids attached. During the esterification process, the triglyceride is reacted with alcohol, usually methanol, in the presence of a catalyst, usually a strong alkaline such as sodium hydroxide. The methanol reacts with the fatty acids to produce methyl esters and crude glycerol.
The amount of glycerol produced as a by-product is about 1 tonne for every ten tonnes of biodiesel. The UK Government has set a target of producing 20% of the nation's fuel from natural sources by the year 2020. If this were to be in the form of biodiesel, this would translate to 3.6 million tonnes of biodiesel and about 360,000 tonnes of glycerol. The current world market for glycerol is in the region of 150,000 tonnes per year, so the waste glycerol from UK sources alone will be nearly 2.5 times the current world consumption. It is very unlikely that sufficient new uses will be found for glycerol to consume the anticipated production as a by-product.
Waste glycerol from the production of biodiesel is contaminated with fatty acids and other related materials, and would require purification before it could be sold for industrial use. Since the market demand is insufficient, this is not feasible for all waste glycerol. Current ideas for disposal include burning and biological digestion. Glycerol has approximately 50% of the calorific value of fuel oil, and burning is therefore not an attractive option. Current disposal costs for waste glycerol are in the region of £30 per tonne. Summary of the Invention
According to the present invention, there is provided a method for the manufacture of bio diesel fuel from vegetable oils, comprising treating the oils with methanol and a base catalyst to cause esterification yielding methyl fatty acid esters and glycerol, separating the glycerol from the estehfied oil, treating the glycerol with a catalyst to yield methanol, and using the methanol produced in the esterification of further vegetable oil. Preferably, the glycerol is reacted with a catalyst in the presence of a reducing gas such as carbon monoxide or hydrogen. The catalyst is suitably a mixed base metal oxide/precious metal. It is suitably presented in thin film form. The metal oxide may be, for example, zinc oxide, and the precious metal is suitably palladium. The catalyst is preferably operated at elevated tempera- tures, for example in the region of 300° C to 800° C, and so the glycerol will need to be in vapour form, but may need protection from thermal breakdown.
Pre-treatment of the glycerol may be required to remove contaminants which might adversely affect the catalytic reaction.
The methanol is typically produced by the reaction in vapour form and will therefore need to be condensed. Purification of the methanol may be needed before it can be used in the esterification process, for example to remove water.
Although at first sight the production of methanol in this way might not seem to be an economically attractive idea, as glycerol currently has a higher price than methanol, in practice it is expected that the following factors will favour the process:
1 . glycerol is dropping in price and will continue to fall due to the glut of glycerol on the market from the production of bio diesel.
2. The price of methanol is rising. 3. Reuse of glycerol on the side of bio diesel production will save on disposal costs, currently around £30 per tonne.
4. Recycling of glycerol as methanol will reduce on-site storage requirements and hence fire hazards.
5. Recycling will reduce tanker movements delivering methanol. 6. Greenhouse gas emissions in the production of methanol will be reduced. Brief Description of the Drawing
The drawing represents diagrammatically a process for the manufacture of biodiesel according to one embodiment of the invention. Detailed Description of the Illustrated Embodiment In the drawing, vegetable oil, for example produced by milling or pressing rape seed or similar oil-bearing seed, is stored in an oil feed tank 1. it will be appreciated that oils from a range of different vegetable sources may be used, as well as recycled cooking oils. The oil feed tank 1 supplies oil to a reactor 2, which is also supplied with methanol from a methanol feed tank 3, and with so- dium hydroxide solution from a base supply tank 4. The esterified oil passes to a separation stage 5 where the glycerol is separated off for supply to a second vapour phase reactor 6. The biodiesel oil is removed by line 7 for further treatment (not shown). The reactor 2 will typically be a batch reactor. While the supply of sodium hydroxide and methanol are shown to be separate, in practice it may be desirable to mix the two before introduction into and mixing with the crude vegetable oil. A typical batch reaction might occupy 4 to 6 hours.
The reactor 6 contains the zinc oxide/palladium catalyst and is supplied with carbon monoxide from a supply vessel 8. The methanol vapour is led to a condenser 9 and the liquid methanol passes to a purification/drying stage 10 before being delivered to the methanol feed tank 3.
The process will employ heat recovery to ensure energy efficiency. For example, the esterification reaction requires heat input to maintain a temperature of around 500C, and the catalytic reaction requires to be carried out at elevated temperatures in excess of 3000C.

Claims

- A -CLAIMS
1. A method for the manufacture of biodiesel fuel from vegetable oils, comprising treating the oils with methanol and a base catalyst to cause esterifi- cation yielding methyl fatty acid esters and glycerol, separating the glycerol from the esterified oil, treating the glycerol with a catalyst to yield methanol, and using the methanol produced in the esterification of further vegetable oil.
2. A method according to Claim 1 , wherein the glycerol is treated with the catalyst in the presence of a reducing gas.
3. A method according to Claim 2, wherein the reducing gas is carbon monoxide or hydrogen.
4. A method according to Claim 1 , 2 or 3, wherein the catalyst is a mixed base metal oxide and precious metal catalyst.
5. A method according to Claim 4, wherein the base metal oxide is zinc oxide.
6. A method according to Claim 4 or 5, wherein the precious metal is palladium.
7. A method according to any preceding claim, wherein the catalyst is operated at a temperature in the region of 300° C. to 800° C.
8. A method according to any preceding claim, wherein the methanol is purified before use in the esterification process.
PCT/GB2007/050614 2006-10-05 2007-10-04 Manufacture of biodiesel fuel WO2008041038A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0619691.9 2006-10-05
GBGB0619691.9A GB0619691D0 (en) 2006-10-05 2006-10-05 Manufacture of biodiesel fuel

Publications (1)

Publication Number Publication Date
WO2008041038A1 true WO2008041038A1 (en) 2008-04-10

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WO (1) WO2008041038A1 (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009143159A1 (en) * 2008-05-19 2009-11-26 Wayne State University Methods and catalysts for making biodiesel from the transesterification and esterification of unrefined oils
ES2350076A1 (en) * 2009-05-26 2011-01-18 Fundacion Investigacion E Innovacion Para El Desarrollo Social Glycerine conversion in methanol (Machine-translation by Google Translate, not legally binding)
US7897798B2 (en) 2006-08-04 2011-03-01 Mcneff Research Consultants, Inc. Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same
US7943791B2 (en) 2007-09-28 2011-05-17 Mcneff Research Consultants, Inc. Methods and compositions for refining lipid feed stocks
US8017796B2 (en) 2007-02-13 2011-09-13 Mcneff Research Consultants, Inc. Systems for selective removal of contaminants from a composition and methods of regenerating the same
US8361174B2 (en) 2008-10-07 2013-01-29 Sartec Corporation Catalysts, systems, and methods for producing fuels and fuel additives from polyols
US8445709B2 (en) 2006-08-04 2013-05-21 Mcneff Research Consultants, Inc. Systems and methods for refining alkyl ester compositions
US8585976B2 (en) 2007-02-13 2013-11-19 Mcneff Research Consultants, Inc. Devices for selective removal of contaminants from a composition
US8895764B2 (en) 2008-05-19 2014-11-25 Wayne State University ZnO nanoparticle catalysts for use in biodiesel production and method of making
US8975426B2 (en) 2008-05-19 2015-03-10 Wayne State University ZnO nanoparticle catalysts for use in transesterification and esterification reactions and method of making
US9102877B2 (en) 2008-11-12 2015-08-11 Sartec Corporation Systems and methods for producing fuels from biomass
US10239812B2 (en) 2017-04-27 2019-03-26 Sartec Corporation Systems and methods for synthesis of phenolics and ketones
US10544381B2 (en) 2018-02-07 2020-01-28 Sartec Corporation Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid
US10696923B2 (en) 2018-02-07 2020-06-30 Sartec Corporation Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids

Citations (3)

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Publication number Priority date Publication date Assignee Title
EP0117944A2 (en) * 1982-12-13 1984-09-12 Imperial Chemical Industries Plc Methanol synthesis and catalyst therefor
EP0523014A2 (en) * 1991-07-10 1993-01-13 NOVAMONT S.p.A. A catalytic method of hyrogenating glycerol
EP1698681A1 (en) * 2003-11-27 2006-09-06 Revo International Inc. Process for producing diesel fuel oil from fat

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
EP0117944A2 (en) * 1982-12-13 1984-09-12 Imperial Chemical Industries Plc Methanol synthesis and catalyst therefor
EP0523014A2 (en) * 1991-07-10 1993-01-13 NOVAMONT S.p.A. A catalytic method of hyrogenating glycerol
EP1698681A1 (en) * 2003-11-27 2006-09-06 Revo International Inc. Process for producing diesel fuel oil from fat

Non-Patent Citations (1)

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Title
MIYAZAWA ET AL: "Glycerol conversion in the aqueous solution under hydrogen over Ru/C + an ion-exchange resin and its reaction mechanism", JOURNAL OF CATALYSIS, ACADEMIC PRESS, DULUTH, MN, US, vol. 240, no. 2, 10 June 2006 (2006-06-10), pages 213 - 221, XP005416144, ISSN: 0021-9517 *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8445709B2 (en) 2006-08-04 2013-05-21 Mcneff Research Consultants, Inc. Systems and methods for refining alkyl ester compositions
US8686171B2 (en) 2006-08-04 2014-04-01 Mcneff Research Consultants, Inc. Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same
US7897798B2 (en) 2006-08-04 2011-03-01 Mcneff Research Consultants, Inc. Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same
US8585976B2 (en) 2007-02-13 2013-11-19 Mcneff Research Consultants, Inc. Devices for selective removal of contaminants from a composition
US8017796B2 (en) 2007-02-13 2011-09-13 Mcneff Research Consultants, Inc. Systems for selective removal of contaminants from a composition and methods of regenerating the same
US8466305B2 (en) 2007-09-28 2013-06-18 Mcneff Research Consultants, Inc. Methods and compositions for refining lipid feed stocks
US7943791B2 (en) 2007-09-28 2011-05-17 Mcneff Research Consultants, Inc. Methods and compositions for refining lipid feed stocks
US8163946B2 (en) 2008-05-19 2012-04-24 Wayne State University Methods and catalysts for making biodiesel from the transesterification and esterification of unrefined oils
WO2009143159A1 (en) * 2008-05-19 2009-11-26 Wayne State University Methods and catalysts for making biodiesel from the transesterification and esterification of unrefined oils
US8895764B2 (en) 2008-05-19 2014-11-25 Wayne State University ZnO nanoparticle catalysts for use in biodiesel production and method of making
US8975426B2 (en) 2008-05-19 2015-03-10 Wayne State University ZnO nanoparticle catalysts for use in transesterification and esterification reactions and method of making
US8361174B2 (en) 2008-10-07 2013-01-29 Sartec Corporation Catalysts, systems, and methods for producing fuels and fuel additives from polyols
US9102877B2 (en) 2008-11-12 2015-08-11 Sartec Corporation Systems and methods for producing fuels from biomass
ES2350076A1 (en) * 2009-05-26 2011-01-18 Fundacion Investigacion E Innovacion Para El Desarrollo Social Glycerine conversion in methanol (Machine-translation by Google Translate, not legally binding)
US10239812B2 (en) 2017-04-27 2019-03-26 Sartec Corporation Systems and methods for synthesis of phenolics and ketones
US10544381B2 (en) 2018-02-07 2020-01-28 Sartec Corporation Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid
US10696923B2 (en) 2018-02-07 2020-06-30 Sartec Corporation Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids

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