Method of making alkyl esters using pressure

Details Method of making alkyl esters using pressure Method of making alkyl esters using pressure

2003-08-12

2004-07-27

Carr, Deborah D. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C560S205000

Reexamination Certificate

active

06768015

ABSTRACT:

BACKGROUND OF THE INVENTION
Alkylesters, or methylester specifically, such as biodiesel, are a clean-burning replacement for conventional petroleum-based diesel. Biodiesel may be made from natural, renewable sources such as new or used vegetable oils and animal fats. Biodiesel is fatty acid alkyl esters (typically being C
16
to C
18
) and can generally be burned in combustion-ignition engines as a direct replacement for petroleum-based diesel. Aside from providing the benefit that biodiesel may be generated from renewable sources, biodiesel also provides the added benefit of decreased emissions from its combustion as compared to the combustion of petroleum-based diesel.
Alkylesters, in particular biodiesel, may be derived from the oils of the soybean or the rapeseed. The crude vegetable oil from these sources may be filtered, refined and subjected to several processing steps before the oil may be usable as biodiesel. Additionally, biodiesel may be derived from varying grades of vegetable oils. Such grades include virgin oil, yellow grease, used oils from food processing, or by-products from the edible oil refining process such as soap stock. Each of these sources has varying amounts of free fatty acids and/or glycerides—i.e., mono-, di-, or tri-glycerides—that may be processed into biodiesel.
Of these sources of vegetable oil, soap stock is generally considered the most cost effective source. Soap stock is derived from the crude oil extracted from the soybean or rapeseed. The crude oil of these seeds may be separated into two components: refined oil (which may then be further processed and converted into edible oil) and soap stock. The soap stock may then be acidulated with sulfuric acid to provide a composition having about 70% free fatty acids that may be further processed into biodiesel.
One contemplated method of processing the free fatty acids from these various grades of vegetable oils is the direct transesterification of the free fatty acids in the presence of alkali to produce the fatty acid alkyl esters for use as biodiesel. Such an approach, however, causes the free fatty acids to precipitate as soap, creating an additional recovery step in the contemplated method.
To avoid the precipitation problem, a two-step method for processing the free fatty acids has been proposed. This method can be found in EP 07 708 813 and WO 02/28811, and generally consists of the steps of (1) acid catalyzed esterification of free fatty acids with methanol in the presence of sulfuric acid, and (2) neutralization of the acid catalyst followed by conventional base catalyzed transesterification. These steps can be described by the following reaction scheme.
where each R may be the same or different and an aliphatic chain typically found in vegetable or animal oil sources, typically C
8
to C
22
.
Even though transesterifications are both acid and base catalyzed, neutralization of the acid catalyst is necessary because acid catalyzed transesterifications typically exhibit slower kinetics than base catalyzed transesterifications, under comparable conditions. The disadvantages of two-step methods as disclosed in EP 07 708 813 and WO 02/28811 are the additional salt waste from neutralization, long cycle times, and a cumbersome recovery scheme of residual free fatty acids.
BRIEF SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide a method of processing free fatty acids from a vegetable or animal oil source into alky esters in which the salt and aqueous waste is reduced or eliminated.
It is a further object of the present invention to provide a method of processing free fatty acids from a vegetable or animal oil source into alkyl esters in which the cycle times are reduced.
It is a further object of the present invention to provide a method of processing free fatty acids from a vegetable or animal oil source into alkyl esters in which the recovery scheme of residual free fatty acids is conveniently performed or the need for such recovery is eliminated.
It is a further object of the invention to provide a method capable of performing esterification and transesterification simultaneously in one step.
These and other advantages are accomplished by subjecting the vegetable or animal oil source to a single step method constituting a direct transformation of the free fatty acid and glycerides of the vegetable or animal oil source with methanol. The single step process does not involve a neutralization step thus simplifying the process. The single step method is generally described below.
where each R may be the same or different and may be H or an aliphatic chain typically found in vegetable or animal oil sources, typically C
8
to C
22
.


REFERENCES:
patent: 5151547 (1992-09-01), Sato et al.
patent: 5302746 (1994-04-01), Koono et al.
patent: 2001/0042340 (2001-11-01), Tateno et al.
patent: 1126011 (2001-08-01), None
patent: 1126011 (2001-08-01), None
patent: 1211236 (2002-08-01), None

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