WO2011134049A1 - Process for extracting a fatty acid alkyl ester from a crude glycerine composition - Google Patents

Process for extracting a fatty acid alkyl ester from a crude glycerine composition Download PDF

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Publication number
WO2011134049A1
WO2011134049A1 PCT/CA2011/000464 CA2011000464W WO2011134049A1 WO 2011134049 A1 WO2011134049 A1 WO 2011134049A1 CA 2011000464 W CA2011000464 W CA 2011000464W WO 2011134049 A1 WO2011134049 A1 WO 2011134049A1
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process defined
parts
composition
range
crude glycerine
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PCT/CA2011/000464
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French (fr)
Inventor
Michel M. De Verteuil
Michael T. Lau
Jing Zhang
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Proprietect L.P.
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    • 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
    • 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
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • 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
    • 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
    • C10G2300/1011—Biomass
    • C10G2300/1014—Biomass of vegetal origin
    • 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
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

Definitions

  • the present invention relates to a process for extracting a fatty acid alkyl ester from a crude glycerine composition.
  • Biodiesel processing involves the production of alkyl esters of long chain fatty acids by reacting the source acid with a low molecular weight alcohol, such as methanol (i.e., methylation in the case of methanol).
  • a low molecular weight alcohol such as methanol (i.e., methylation in the case of methanol).
  • a conventional process for manufacturing fatty acid alkyl esters involves the transesterification of triglycerides (e.g., from animal fat sources or any other sources of (tri)glycerides) using methanol, in the presence of an alkali catalyst (caustic soda).
  • this process produces a so-called glycerine effluent stream comprising glycerine (glycerol), excess alcohol, residual fatty acid alkyl ester, a mixture of mono-, di- and tri-glycerides resulting from the transesterification step, salts and other minor components.
  • one of the components of the glycerine stream is residual fatty acid alkyl ester. This is the desired biofuel product. Accordingly, it would be desirable to have a process for separating the residual fatty acid alkyl ester from the glycerine stream thereby yielding a valuable supplemental source of the desired biofuel product.
  • One of the applications for glycerine is in the production of isocyanate-based polymer foams - e.g., polyurethane foams.
  • One of the problems of using the crude glycerine stream from a biofuel product process is that the presence of fatty acid alkyl ester in the crude glycerine stream often renders the crude glycerine stream incompatible with the chemical systems used to produce the isocyanate-based polymer foams. Specifically, it is believed that the relatively high salt content (e.g., sodium sulfate) in the crude glycerine stream serves to contribute to the incompatible of the latter with the chemical systems conventionally used to produce polyurethane foam. [0008] It would therefore be desirable to provide a low cost efficient process for purification of glycerine recovered from fatty acid alkyl ester processes, such as the manufacture of biodiesels.
  • the relatively high salt content e.g., sodium sulfate
  • Such a process would also provide an efficient low cost means for recovering additional fatty acid alkyl ester on the one hand while improving the compatibility of the glycerine stream with the chemical systems used to produce isocyanate-based foams such as polyurethane foams.
  • a goal of the present invention is to provide a relatively simple, low-cost process for purifying glycerine byproduct from biodiesel production so as to efficiently improve the the over all yield of fatty acid alkyl ester (the biofuel component) while concurrently improving the quality of the byproduct glycerine stream so as to improve the compatability thereof with the chemical systems used to produce isocyanate-based polymer foams such as polyurethane foams.
  • the present invention provides a process for extracting a fatty acid alkyl ester from a crude glycerine composition, the process comprising the steps of:
  • the present inventors have discovered that it is possible to extract fatty acid alkyl ester from a crude glycerine composition by combining the crude glycerine composition with an aqueous liquid.
  • aqueous liquid and temperature When preferred amounts of aqueous liquid and temperature are used, it is possible to extract a significant amount of residual fatty acid alkyl ester from the crude glycerine composition.
  • the present invention relates to a process for extracting a fatty acid alkyl ester from a crude glycerine composition.
  • Preferred embodiments of the process may include any one or a combination of any two or more of any of the following features: the crude glycerine composition may be derived from animal fat that has been subjected to at least one treatment step; the at least one treatment step may comprise digestion with caustic soda to produce an intermediate composition comprising fatty acid and glycerine; the intermediate composition may be subjected to an alkylation step to produce produce the crude gycerin composition; the intermediate composition may be subjected to a neutralization step followed by an alkylation step to produce the crude gycerin composition; the crude glycerine composition comprises a fatty acid alkyl ester, glycerine and at least one salt selected from the group consisting of alkali metal salts and alkaline earth metal
  • Step (a) in the process may comprise adding an aqueous liquid to the crude glycerine composition to cause phase separation to produce three phases comprising an organic phase, an aqueous phase and a solids phase; • the solids phase may comprise at least one salt selected from the group consisting of alkali metal salts and alkaline earth metal salts;
  • the solids phase may comprises an alkali metal salt
  • the solids phase may comprise a sodium salt
  • the solids phase may comprise sodium sulphate
  • Step (a) in the process may be conducted with agitation
  • Step (a) in the process may be conducted with mechanical agitation
  • Step (a) in the process may be conducted with mechanical stirring
  • Step (a) in the process may be conducted with centrifugal agitation
  • Step (a) in the process may be conducted with ultrasonic agitation
  • Step (a) in the process may be conducted at a temperature in the range of from about 10° to about 100°C;
  • Step (a) in the process may be conducted at a temperature in the range of from about 15° to about 95°C;
  • Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 90°C;
  • Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 70°C
  • Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 55°C;
  • Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 40°C; Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 30°C;
  • Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 25°C;
  • Step (a) in the process may be conducted at a temperature of about 20°C;
  • Step (a) in the process may be conducted at a temperature of about 90°C; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 400 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 300 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 200 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 150 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 100 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a)
  • the amount of aqueous liquid used in Step (a) may be in the range of from about 15 parts by weight to about 65 parts by weight per 100 parts by crude glycerine composition;
  • the amount of aqueous liquid used in Step (a) may be in the range of from about 15 parts by weight to about 45 parts by weight per 100 parts by crude glycerine composition;
  • the amount of aqueous liquid used in Step (a) may be in the range of from about 15 parts by weight to about 40 parts by weight per 100 parts by crude glycerine composition;
  • the fatty acid alkyl ester may comprise a fatty acid methyl ester
  • the aqueous liquid may be water.
  • the starting material used in these Examples was a crude glycerine composition obtained from a biofuel production process.
  • the crude glycerine composition contained the components set out in Table 1. Table 1
  • the fatty acid methyl ester recovered can be used as a valuable fuel source while the residual glycerine composition is expected to be more compatible with the chemical systems used to make polyurethane foams since the residual glycerine composition has a significantly reduced amount of sodium sulfate.

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

There is described a process for purifying the crude glycerol obtained from the production of fatty acid alkyl esters via transesterification. The process comprises the steps of; (a) adding an aqueous liquid to the crude glycerine composition to cause phase separation to produce at least two phases comprising an organic phase and an aqueous phase; (b) separating the organic phase from the aqueous phase; and (c) separating the fatty acid alkyl ester from the organic phase. When preferred amounds of aqueous liquid and temperature are used, it is possible to extract a significant amount of residual fatty acid alkyl ester from the crude glycerine composition.

Description

PROCESS FOR EXTRACTING A FATTY ACID ALKYL ESTER FROM A CRUDE
GLYCERINE COMPOSITION
CROSS-REFERENCE TO RELATED APPLICATION
[0001] The present application claims the benefit under 35 U.S.C. §119(e) of provisional patent application S.N. 61/282,949, filed April 28, 2010, the contents of which are hereby incorporated by reference.
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
[0002] The present invention relates to a process for extracting a fatty acid alkyl ester from a crude glycerine composition.
DESCRIPTION OF THE PRIOR ART
[0003] As a result of the continuing rise in the cost of fossil fuels, there has been an increasing interest in biodiesel fuels as a supplement to or replacement for traditional fossil fuel sources. Biodiesel processing involves the production of alkyl esters of long chain fatty acids by reacting the source acid with a low molecular weight alcohol, such as methanol (i.e., methylation in the case of methanol).
[0004] A conventional process for manufacturing fatty acid alkyl esters involves the transesterification of triglycerides (e.g., from animal fat sources or any other sources of (tri)glycerides) using methanol, in the presence of an alkali catalyst (caustic soda). In addition to the desired fatty acid alkyl esters, this process produces a so-called glycerine effluent stream comprising glycerine (glycerol), excess alcohol, residual fatty acid alkyl ester, a mixture of mono-, di- and tri-glycerides resulting from the transesterification step, salts and other minor components.
[0005] There are at least two areas in need of improvement. [0006] First, one of the components of the glycerine stream is residual fatty acid alkyl ester. This is the desired biofuel product. Accordingly, it would be desirable to have a process for separating the residual fatty acid alkyl ester from the glycerine stream thereby yielding a valuable supplemental source of the desired biofuel product. [0007] Second, the rapid worldwide expansion in the production of biodiesel fuel since 2000 has created a fast growing supply of byproduct crude glycerine. One of the applications for glycerine is in the production of isocyanate-based polymer foams - e.g., polyurethane foams. One of the problems of using the crude glycerine stream from a biofuel product process is that the presence of fatty acid alkyl ester in the crude glycerine stream often renders the crude glycerine stream incompatible with the chemical systems used to produce the isocyanate-based polymer foams. Specifically, it is believed that the relatively high salt content (e.g., sodium sulfate) in the crude glycerine stream serves to contribute to the incompatible of the latter with the chemical systems conventionally used to produce polyurethane foam. [0008] It would therefore be desirable to provide a low cost efficient process for purification of glycerine recovered from fatty acid alkyl ester processes, such as the manufacture of biodiesels. Such a process would also provide an efficient low cost means for recovering additional fatty acid alkyl ester on the one hand while improving the compatibility of the glycerine stream with the chemical systems used to produce isocyanate-based foams such as polyurethane foams. In addition, it would be highly desirable if the process could be implemented utilizing predominately commonly available equipment such as might be available from idle facilities or surplus equipment previously used for other purposes. Thus, a goal of the present invention is to provide a relatively simple, low-cost process for purifying glycerine byproduct from biodiesel production so as to efficiently improve the the over all yield of fatty acid alkyl ester (the biofuel component) while concurrently improving the quality of the byproduct glycerine stream so as to improve the compatability thereof with the chemical systems used to produce isocyanate-based polymer foams such as polyurethane foams. SUMMARY OF THE INVENTION
[0009] It is an object of the present invention to obviate or mitigate at least one of the above-mentioned disadvantages of the prior art.
[0010] It is another object of the present invention to provide a novel process for extracting a fatty acid alkyl ester from a crude glycerine composition.
[0011] Accordingly, in one of its aspects, the present invention provides a process for extracting a fatty acid alkyl ester from a crude glycerine composition, the process comprising the steps of:
(a) adding an aqueous liquid to the crude glycerine composition to cause phase separation to produce at least two phases comprising an organic phase and an aqueous phase;
(b) separating the organic phase from the aqueous phase; and
(c) separating the fatty acid alkyl ester from the organic phase.
[0012] Thus, the present inventors have discovered that it is possible to extract fatty acid alkyl ester from a crude glycerine composition by combining the crude glycerine composition with an aqueous liquid. When preferred amounts of aqueous liquid and temperature are used, it is possible to extract a significant amount of residual fatty acid alkyl ester from the crude glycerine composition.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS [0013] In one of its aspects, the present invention relates to a process for extracting a fatty acid alkyl ester from a crude glycerine composition. Preferred embodiments of the process may include any one or a combination of any two or more of any of the following features: the crude glycerine composition may be derived from animal fat that has been subjected to at least one treatment step; the at least one treatment step may comprise digestion with caustic soda to produce an intermediate composition comprising fatty acid and glycerine; the intermediate composition may be subjected to an alkylation step to produce produce the crude gycerin composition; the intermediate composition may be subjected to a neutralization step followed by an alkylation step to produce the crude gycerin composition; the crude glycerine composition comprises a fatty acid alkyl ester, glycerine and at least one salt selected from the group consisting of alkali metal salts and alkaline earth metal salts; the crude glycerine composition may comprise a fatty acid alkyl ester, glycerine and at least one salt selected from the group consisting of alkali metal salts and alkaline earth metal salts; the crude glycerine composition may comprise a fatty acid alkyl ester, glycerine and at least one alkali metal salt; the crude glycerine composition may comprise a fatty acid alkyl ester, glycerine and at least one sodium salt; the crude glycerine composition may comprise a fatty acid alkyl ester, glycerine and sodium sulphate;
Step (a) in the process may comprise adding an aqueous liquid to the crude glycerine composition to cause phase separation to produce three phases comprising an organic phase, an aqueous phase and a solids phase; • the solids phase may comprise at least one salt selected from the group consisting of alkali metal salts and alkaline earth metal salts;
• the solids phase may comprises an alkali metal salt;
• the solids phase may comprise a sodium salt;
• the solids phase may comprise sodium sulphate;
• Step (a) in the process may be conducted with agitation;
• Step (a) in the process may be conducted with mechanical agitation;
• Step (a) in the process may be conducted with mechanical stirring;
• Step (a) in the process may be conducted with centrifugal agitation;
• Step (a) in the process may be conducted with ultrasonic agitation;
• Step (a) in the process may be conducted at a temperature in the range of from about 10° to about 100°C;
• Step (a) in the process may be conducted at a temperature in the range of from about 15° to about 95°C;
• Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 90°C;
• Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 70°C
• Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 55°C;
• Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 40°C; Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 30°C;
Step (a) in the process may be conducted at a temperature in the range of from about 20° to about 25°C;
Step (a) in the process may be conducted at a temperature of about 20°C;
Step (a) in the process may be conducted at a temperature of about 90°C; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 400 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 300 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 200 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 150 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 5 parts by weight per 100 parts by crude glycerine composition; the amount of aqueous liquid used in Step (a) may be in the range of from about 10 parts by weight to about 70 parts by weight per 100 parts by crude glycerine composition; • the amount of aqueous liquid used in Step (a) may be in the range of from about 15 parts by weight to about 70 parts by weight per 100 parts by crude glycerine composition;
• the amount of aqueous liquid used in Step (a) may be in the range of from about 15 parts by weight to about 65 parts by weight per 100 parts by crude glycerine composition;
• the amount of aqueous liquid used in Step (a) may be in the range of from about 15 parts by weight to about 45 parts by weight per 100 parts by crude glycerine composition;
• the amount of aqueous liquid used in Step (a) may be in the range of from about 15 parts by weight to about 40 parts by weight per 100 parts by crude glycerine composition;
• the fatty acid alkyl ester may comprise a fatty acid methyl ester; and/or
• the aqueous liquid may be water.
[0014] Embodiments of the present invention will be illustrated with reference to the following non-limiting examples which should not be used to construe the scope of the invention.
EXAMPLES 1-9
[0015] The starting material used in these Examples was a crude glycerine composition obtained from a biofuel production process. The crude glycerine composition contained the components set out in Table 1. Table 1
Figure imgf000009_0001
[0016] To a 600 mL beaker was added 200 g of the crude glycerine composition. At ambient temperature (25 °C), water in the amount shown in Table 2 was added to the beaker and the contents of the beaker were transferred to a high shear mixture operated at at 3000 rpm. Stirring was continued for the shorter of 15 minutes or when it appeared that components were beginning to separate (even with stirring).
[0017] The time to achieve separation of the mixture to three distinct layers is reporting in Table 2. The three distinct layers consisted of
(a) a top, organic liquid phase containing the fatty acid methyl ester;
and
(b) a middle, aqueous liquid phase containing glycerol, water,
methanol and water soluble salts; and
(c) a bottom, solid layer containing sodium sulfate and other water
insoluble salts and organic solids.
Further, the amount of fatty acid methyl ester recovered from the top, organic liquid phase, together with the percent recovery based on the original constitution of the starting crude glycerine composition, is also reported in Table 2. [0018] The results in Table 2 illustrate that a significant amount of fatty acid methyl ester was recoverd in Examples 5-9, particularly in Example 6. The results in Table 2 also show that that a significant about of sodium sulfate originally contained in the starting crude glycerine composition was in fact separated from that composition. Thus, the fatty acid methyl ester recovered can be used as a valuable fuel source while the residual glycerine composition is expected to be more compatible with the chemical systems used to make polyurethane foams since the residual glycerine composition has a significantly reduced amount of sodium sulfate.
EXAMPLES 10-19 [0019] Unless otherwise noted in Table 3, to a 600 mL beaker containing a high shear mixer was added 200 g of the same crude glycerine composition used in Examples 1-9. The crude glycerine composition was heat to approximately 90°C using a hot plate with high shear mixer being operated at approximately 3000 rpm. Ambient temperature (25°C) water was added to the beaker in the amount shown in Table 3. The was observed as decreasing and the contents of the beaker were heated to 90°C using the hot plate with high shear mixer being operated at approximately 3000 rpm. Stirring was continued for the shorter of 15 minutes or when it appeared that components were beginning to separate (even with stirring).
[0020] The time to achieve separation of the mixture to three distinct layers (as described above in relation to Examples 1-9) is reported in Table 3. Further, the amount of fatty acid methyl ester recovered from the top, organic liquid phase, together with the percent recovery based on the original constitution of the starting crude glycerine composition, is also reported in Table 3.
[0021] The results in Table 2 illustrate that a significant amount of fatty acid methyl ester was recoverd in Examples 15-19, particularly in Example 18. As with Table 2, the results in Table 3 also show that that a significant about of sodium sulfate originally contained in the starting crude glycerine composition was in fact separated from that composition. Again, the fatty acid methyl ester recovered can be used as a valuable fuel source while the residual glycerine composition is expected to be more compatible with the chemical systems used to make polyurethane foams since the residual glycerine composition has a significantly reduced amount of sodium sulfate.
[0022] While this invention has been described with reference to illustrative embodiments and examples, the description is not intended to be construed in a limiting sense. Thus, various modifications of the illustrative embodiments, as well as other embodiments of the invention, will be apparent to persons skilled in the art upon reference to this description. For example, while reference has been made to the use of a crude gylcerine composition derived from animal fat sources, the crude glycerine composition useful in the present process may be derived from any other source of (tri)glycerides. Further, while reference was made in the Examples to the use of agitation via a high shear mixer, it is possible to use other modes of agititation (vigorous or non- vigorous) in the present process. Still further, while a specific crude glycerine composition was used in the Examples to illustrate embodiments of the invention, those of skill in the art will recognize that the present process may be used with other crude glyrcerin compositions having varying components and/or relative amounts of components compared to the crude glycerine composition used in the Examples. It is therefore contemplated that the appended claims will cover any such modifications or embodiments.
[0023] All publications, patents and patent applications referred to herein are incorporated by reference in their entirety to the same extent as if each individual publication, patent or patent application was specifically and individually indicated to be incorporated by reference in its entirety. Table 2
Figure imgf000012_0001
Notes: (1) "pphp" = part by weight per 100 parts by weight of the starting crude glycerine composition
(2) Based on starting crude glycerine composition containing 5 weight percent FAME
(3) Recovered from solid phase 15 weight percent Na2S04
(4) Based on starting crude glycerine composition containing 15 weight percent Na2S04
Table 3
Figure imgf000013_0001
Notes: ( 1 ) "pphp" = part by weight per 100 parts by weight of the starting crude glycerine composition
(2) Based on starting crude glycerine composition contained 5 weight percent FAME
(3) Recovered from solid phase 15 weight percent Na2S04
(4) Based on starting crude glycerine composition containing 15 weight percent Na2S04
(5) Procedure modified to use 400 g of starting crude glycerine composition
(6) Procedure modified to use 300 g of starting crude glycerine composition

Claims

What is claimed is:
1. A process for extracting a fatty acid alkyl ester from a crude glycerine composition, the process comprising the steps of:
(a) adding an aqueous liquid to the crude glycerine composition to cause phase separation to produce at least two phases comprising an organic phase and an aqueous phase;
(b) separating the organic phase from the aqueous phase; and
(c) separating the fatty acid alkyl ester from the organic phase.
2. The process defined in Claim 1 , wherein the crude glycerine composition is derived from animal fat that has been subjected to at least one treatment step.
3. The process defined in Claim 2, wherein the at least one treatment step comprises digestion with caustic soda to produce an intermediate composition comprising fatty acid and glycerine.
4. The process defined in Claim 3, wherein the intermediate composition is subjected to an alkylation step to produce produce the crude gycerin composition.
5. The process defined in Claim 3, wherein the intermediate composition is subjected to a neutralization step followed by an alkylation step to produce the crude gycerin composition.
6. The process defined in any one of Claims 1-5, wherein the crude glycerine composition comprises a fatty acid alkyl ester, glycerine and at least one salt selected from the group consisting of alkali metal salts and alkaline earth metal salts.
7. The process defined in any one of Claims 1-5, wherein the crude glycerine composition comprises a fatty acid alkyl ester, glycerine and at least one salt selected from the group consisting of alkali metal salts and alkaline earth metal salts.
8. The process defined in any one of Claims 1-5, wherein the crude glycerine composition comprises a fatty acid alkyl ester, glycerine and at least one alkali metal salt.
9. The process defined in any one of Claims 1-5, wherein the crude glycerine composition comprises a fatty acid alkyl ester, glycerine and at least one sodium salt.
10. The process defined in any one of Claims 1-5, wherein the crude glycerine composition comprises a fatty acid alkyl ester, glycerine and sodium sulfate.
11. The process defined in any one of Claims 1-10, wherein Step (a) comprises adding an aqueous liquid to the crude glycerine composition to cause phase separation to produce three phases comprising an organic phase, an aqueous phase and a solids phase.
12. The process defined in Claim 11, wherein the solids phase comprises at least one salt selected from the group consisting of alkali metal salts and alkaline earth metal salts.
13. The process defined in Claim 11, wherein the solids phase comprises an alkali metal salt.
14. The process defined in Claim 1 1, wherein the solids phase comprises a sodium salt.
15. The process defined in Claim 11 , wherein the solids phase comprises sodium sulfate.
16. The process defined in any one of Claims 1-15, wherein Step (a) is conducted with agitation.
17. The process defined in any one of Claims 1-15, wherein Step (a) is conducted with mechanical agitation.
18. The process defined in any one of Claims 1-15, wherein Step (a) is conducted with mechanical stirring.
19. The process defined in any one of Claims 1-15, wherein Step (a) is conducted with centrifugal agitation.
20. The process defined in any one of Claims 1-15, wherein Step (a) is conducted with ultrasonic agitation.
21. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature in the range of from about 10° to about 100°C.
22. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature in the range of from about 15° to about 95°C.
23. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature in the range of from about 20° to about 90°C.
24. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature in the range of from about 20° to about 70°C.
25. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature in the range of from about 20° to about 55°C.
26. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature in the range of from about 20° to about 40°C.
27. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature in the range of from about 20° to about 30°C.
28. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature in the range of from about 20° to about 25°C.
29. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature of about 20°C.
30. The process defined in any one of Claims 1-20, wherein Step (a) is conducted at a temperature of about 90°C.
31. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 5 parts by weight to about 400 parts by weight per 100 parts by crude glycerine composition.
32. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 5 parts by weight to about 300 parts by weight per 100 parts by crude glycerine composition.
33. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 5 parts by weight to about 200 parts by weight per 100 parts by crude glycerine composition.
34. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 5 parts by weight to about 150 parts by weight per 100 parts by crude glycerine composition.
35. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 5 parts by weight to about 100 parts by weight per 100 parts by crude glycerine composition.
36. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 10 parts by weight to about 70 parts by weight per 100 parts by crude glycerine composition.
37. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 15 parts by weight to about 70 parts by weight per 100 parts by crude glycerine composition.
38. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 15 parts by weight to about 65 parts by weight per 100 parts by crude glycerine composition.
39. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 15 parts by weight to about 45 parts by weight per 100 parts by crude glycerine composition.
40. The process defined in any one of Claims 1-30, wherein the amount of aqueous liquid used in Step (a) is in the range of from about 15 parts by weight to about 40 parts by weight per 100 parts by crude glycerine composition.
41. The process defined in any one of Claims 1-40, wherein the fatty acid alkyl ester comprises a fatty acid methyl ester.
42. The process defined in any one of Claims 1-41, wherein the aqueous liquid is water.
PCT/CA2011/000464 2010-04-28 2011-04-28 Process for extracting a fatty acid alkyl ester from a crude glycerine composition WO2011134049A1 (en)

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