U.S. patent application number 10/926459 was filed with the patent office on 2006-03-02 for fuel products from plant or animal lipids.
Invention is credited to John H. Lee.
Application Number | 20060042158 10/926459 |
Document ID | / |
Family ID | 35941012 |
Filed Date | 2006-03-02 |
United States Patent
Application |
20060042158 |
Kind Code |
A1 |
Lee; John H. |
March 2, 2006 |
Fuel products from plant or animal lipids
Abstract
A novel method for producing fuel products from plant or animal
lipids is provided. The carbon-carbon bonds in the molecules of
plant or animal lipids are cracked into the molecules with smaller
molecular weights. The mixed fuel is formed after chemical
treatments. Then the mixed fuel (biopetroleum) is processed by a
distillation process to produce fuel products according to their
boiling points. The method is particularly advantageous to produce
the energy source from agricultural products, which provides a
solution for energy crisis with a significant potential.
Inventors: |
Lee; John H.; (Olathe,
KS) |
Correspondence
Address: |
RIGEL TECHNOLOGY CORPORATION
11800 WEST 63 STREET, SUITE 26
SHAWNEE
KS
66203
US
|
Family ID: |
35941012 |
Appl. No.: |
10/926459 |
Filed: |
August 26, 2004 |
Current U.S.
Class: |
44/605 |
Current CPC
Class: |
C11C 3/10 20130101; C11C
3/00 20130101; C11C 3/003 20130101; Y02E 50/30 20130101; C10L 1/026
20130101 |
Class at
Publication: |
044/605 |
International
Class: |
C10L 5/00 20060101
C10L005/00 |
Claims
1. A method of producing a fuel composition comprising cracking
unsaturated carbon and carbon bonds in plant or animal lipids,
converting into a mixed fuel, and distillating the mixing fuel to
form the fuel products.
2. The method of claim 1 wherein the unsaturated carbon and carbon
bonds are cracked chemically.
3. The method of claim 1 wherein the unsaturated carbon and carbon
bonds are cracked before or after dissociating glycerol from plant
or animal lipids.
4. The method of claim 1 wherein esterification or
transesterification with the alcohol consisting carbon 1 to 4 is
used to convert fatty acids into esters.
5. The method of claim 4 wherein an enzyme is used for the
transesterification.
6. The method of claim 1 wherein the aldehydes are converted into
alkanes.
7. The method of claim 1 wherein a catalyst is used.
8. The method of claim 1 wherein heat or cooling process is
used.
9. The method of claim 1 wherein the products are used as fuel
products.
10. The method of claim 1 wherein the products are used as organic
products.
11. A method of producing a fuel composition comprising cracking
carbon and carbon bonds in plant or animal lipids, converting into
a mixed fuel, and distillating the mixing fuel to form the fuel
products.
12. The method of claim 11 wherein the carbon and carbon bonds are
cracked by catalyst and pressure cooker.
13. The method of claim 11 wherein the method the carbon and carbon
bonds are cracked before or after dissociating glycerol from the
plant or animal lipids.
14. The method of claim 11 wherein esterification or
transesterification with the alcohol consisting carbon 1 to 4 is
used to convert fatty acids into esters.
15. The method of claim 14 wherein an enzyme is used for the
transesterification.
16. The method of claim 11 wherein the aldehydes are converted into
alkanes.
17. The method of claim 11 wherein a catalyst is used.
18. The method of claim 11 wherein heat or cooling process is
used.
19. The method of claim 11 wherein the products are used as fuel
products.
20. The method of claim 11 wherein the products are used as organic
products.
Description
BACKGROUND OF THE INVENTION
[0001] This present invention relates to a novel processing method
for producing fuels from plant or animal lipids by cracking carbon
and carbon bonds in plant or animal lipids and distillating the
mixing fuels after chemical treatments.
[0002] The energy crisis of recent years has been a significant
challenge. Petroleum is a complex mixture of organic compounds,
most of which are alkanes and aromatic hydrocarbons. Petroleum also
contains small amounts of oxygen, nitrogen, and sulfur-containing
compounds. The primary use of alkanes is as an energy source.
Different fraction products are obtained after a distillation
process. Most fuels that we use are natural gas, petroleum ester,
ligroin, gasoline, kerosene/jet fuel, fuel oil/diesel oil, and
lubrication oil. Natural gas fraction contains 1-4 carbons in the
molecular formula with the boiling point below 20 degree C.
Petroleum ester fraction contains 5-6 carbons in the molecular
formula with the boiling point range at 20-60 degree C. Ligroin
fraction contains 6-7 carbons in the molecular formula with the
boiling point range at 60-100 degree C. Gasoline fraction contains
5-10 carbons in the molecular formula with the boiling point range
at 40-200 degree C. Kerosene and jet fuel fraction contains 12-18
carbons in the molecular formula with the boiling point range at
175-325 degree C. Fuel oil and diesel oil fraction contains 12 and
more carbons in the molecular formula with the boiling point range
at 250-400 degree C. Lubrication oil fraction contains 20 and more
carbons in the molecular formula with a much high boiling point.
Fuels with lower molecular weights usually have lower boiling
points. As we all know that the world's supply of petroleum will
run out sometime in the future. It is a hard fact that our
societies are so largely organized around machines depending on
petroleum-based fuels, which continues the energy challenge. The
solution to the energy crisis is to develop alternate sources of
energy.
[0003] One area of particular interest relates to fuels for
commercial and agricultural vehicles is biodiesel after converting
vegetable or animal oils into ester products. Another area is to
use vegetable or animal oils and their blended oils with other fuel
products for partial replacement for diesel and burning oils. But
there are some important issues such as viscosity, boiling point,
pollution, and burning performance because there are still mixed
compounds in the fuels with high boiling points, sulfur-containing
compounds, and nonvolatile compounds. Over the years, various
attempts have been made to make biodiesel and lubricant oils. A
number of patents have been issued for the processes. U.S. Pat. No.
6,712,867 (2004) discloses a process for production of fatty acid
methyl esters as biodiesel from fatty acid triglycerides with the
ratio of alcohol to triglycerides at 15:1 to 35:1. Very high level
alcohol is needed in the process. U.S. Pat. No. 6,532,918 (2003)
discloses a method and device for lubricating and simultaneously
supplying fuel in a vegetable oil-operated combustion engine. Fresh
vegetable oil and additive-treated vegetable oil are used. U.S.
Pat. No. 6,399,800 (2002) discloses a process for producing fatty
acid alkyl esters by esterifying the dried saponified feedstock
with an alcohol and an inorganic acid catalyst. U.S. Pat. No.
6,015,440 (2000) discloses a process for producing biodiesel fuel
from triglycerides with methanol and a homogeneous basic catalyst.
U.S. Pat. No. 5,885,946 (1999) discloses a process for preparing a
synthetic ester from a vegetable oil by a two-stage
transesterification process. U.S. Pat. No. 5,713,965 (1998)
discloses a method to produce biofuels by utilizing lipases to
transesterify triglyceride-containing substances and to esterify
free fatty acids to alkyl esters using short chain alcohols. U.S.
Pat. No. 5,697,986 (1997) discloses a process to produce biofuels
by carrying out the enzymatic transesterification of fatty
acid-containing materials directly in automative fuels. U.S. Pat.
No. 5,525,126 (1996) discloses a process for producing esters from
a fat or an oil with an alcohol and non-alkaline catalyst. The
catalyst includes a mixture of calcium acetate and barium acetate.
The reaction mixture is heated at a temperature effective to make
esters. U.S. Pat. No. 5,116,546 (1992) discloses a process for
producing fatty acid esters by transesterification, esterification,
and recovery steps. U.S. Pat. No. 4,698,186 (1987) discloses a
process for reducing the free fatty acid content of fats and oils
by esterifying the free fatty acids with a lower monoalcohol in the
presence of an acidic cation exchange resin as a solid
esterification catalyst. U.S. Pat. No. 4,695,411 (1987) discloses a
process for manufacturing fatty acid esters useful for combustion
in diesel engines. There are three processing steps are involved in
the esterification process. U.S. Pat. No. 4,557,734 (1985)
discloses a process for producing microemulsions from vegetable
oil, methanol or ethanol, a straight-chain isomer of octanol, and
optionally water. The fuels are characterized by a relatively high
water tolerance, acceptable viscosity, and performance properties
comparable to No. 2 diesel fuel. U.S. Pat. No. 4,371,470 (1983)
discloses a method for manufacturing fatty acid esters by a
two-step transesterification from a natural oil or fat with methyl
alcohol. The trace amounts of the colored or chromogenic impurities
are removed by admixing an absorbent. U.S. Pat. No. 4,164,506
(1979) discloses a process for producing lower alcohol esters of
fatty acids by esterifying free fatty acids of unrefined fats with
a lower alcohol.
[0004] The principle of preparing biodiesel is transesterification
or esterification, which is described in Organic Chemistry
(Solomons, 1984). Transesterification or alcoholysis of
triglycerides of vegetable oils and animal fats in the presence of
an alcohol leads to the formation of fatty acid esters, which is
also described in European Pat. No. 127,104 and U.S. Pat. No.
4,164,506. After the transesterification or esterification
reactions, the viscosity and boiling points for the esters from
vegetable or animal oils are reduced compared with vegetable or
animal oils. But ester products still have 17-19 carbons in the
molecular formula. Also the final fuel products still contains
other compounds such as sulfur-containing compounds, nonvolatile
compounds, and non-reacted triglycerides and fatty acids, which
affects the burning performance and causes pollution.
DESCRIPTION OF THE INVENTION
[0005] This present invention provides a novel processing method
for producing mixing fuels from plant or animal lipids by cracking
carbon and carbon bonds in plant or animal lipids, chemical
treatments, and distillating the mixing fuels. Then the issues such
as viscosity, molecular weight, boiling point, pollution, and
burning performance with biodiesel can be resolved.
[0006] Plant or animal lipids are such as glyceryl trialkanoates
(is also called triglycerides), carboxylic acids (free fatty
acids), phospholipids, glycolipids, and terpenes. A glyceryl
trialkanoate is made by three fatty acids and one glycerol in the
molecular formula. There are saturated and unsaturated fatty acids.
For unsaturated fatty acids, there are unsaturated (double)
carbon-carbon bonds. A phospholipid is made by two fatty acids, one
phosphoric acid, and one glycerol in the molecular formula.
Terpenes such as essential oil and natural rubber have unsaturated
carbon-carbon bonds and branched methyl groups in the molecular
formula. The lipids, which include such as raw materials, products,
intermediate products, byproducts, and waste products from plant or
animal lipid sources, are used in this process. Most common lipids
such as oils and fats from plant or animal origin are glyceryl
trialkanoates, which are usually have long-chain alkyl groups for
fatty acids. Those glyceryl trialkanoates that are liquids at room
temperature are generally as oils; those that are solids are
usually called fats. The fats become oils after heat. Table 1 shows
major fatty acid composition obtained by hydrolysis of common fats
and oils TABLE-US-00001 TABLE 1 Major fatty acid composition of
common fats and oils (mole, %) Unsaturated Saturated C18/ C18/ C18/
Vegetable Oils C16 C18 C16 oleic linoleic linolenic Soybean 6-10
2-4 20-30 50-58 5-10 Corn 7-11 3-4 1-2 25-35 50-60 Linseed 4-7 2-4
14-30 14-25 45-60 Olive 5-15 1-4 67-84 8-12 Animal Fats Lard 25-30
12-18 4-6 48-60 6-12 Beef tallow 24-34 15-30 35-45 1-3
[0007] (Solomons, 1984). For saturated fatty acids, C16 is palmitic
acid and C18 is stearic acid. For unsaturated fatty acids, C16 is
palmitoleic acid and C18 is oleic acid (cis-9-octadecenoic acid
with one double carbon-carbon bond --HC.dbd.CH--), linoleic acid
(cis, cis-9,12-octadecenoic acid with two double carbon-carbon
bonds --HC.dbd.CH--CH2-HC.dbd.CH--) or linolenic acid (cis, cis,
cis-9, 12, 15-octadecenoic acid with three double carbon-carbon
bonds bonds --HC.dbd.CH--CH2-HC.dbd.CH--CH2-HC.dbd.CH--). To crack
double carbon-carbon bonds of the unsaturated fatty acids in plant
or animal lipids is technically feasible and practical with several
chemical reactions and processes such as (1) oxidative cleavage of
alkenes with an oxidant under base/acid and heat, (2) ozonization
of alkenes with ozone, zinc, and water or (3) hydroxylation of the
double bond using osmium tetroxide, dilute aqueous potassium
permanganate, or a peroxy acid and subsequent cleavage of the
glycol using periodic acid. The chemical reactions are as follows:
[0008] (1) Oxidative cleavage: --HC.dbd.CH--.fwdarw.--COOH (under
base and acid conditions) [0009] (2) Ozonization:
RHC.dbd.CHR'.fwdarw.RHCO+R'HCO [0010] (R and R' are long-chain
alkyl groups with or without glycerol) [0011] (3) Hydroxylation:
RHC.dbd.CHR'.fwdarw.RHCOH--COHHR' [0012]
RHCOH--COHHR'.fwdarw.RHC.dbd.O+O.dbd.CHR' (with HIO4)
[0013] After cracking the double carbon-carbon bonds of the
unsaturated fatty acids in plant or animal lipids, the products are
the mixtures. The carbon numbers in the molecular formulas and
molecular weights in the mixtures are reduced significantly, which
changes the viscosity, boiling points, and burning performance for
the fuels. Cracking the double carbon-carbon bonds of the
unsaturated fatty acids can be done before or after the glycerol in
the lipids is dissociated from the lipid molecules. Glycerol is
water soluble and has a boiling point 290.degree. C. and a density
1.26, which can also be separated by centrifugation process. The
carbon number range for fuel products in the mixed products is
usually from C3 to C18 such as C3 C6, C7, C8, C9, C12, and C18,
which likes petroleum with wide carbon number range. There are also
some compounds with carbon number more than 18 from the raw
materials or intermediate products.
[0014] When cracking the double carbon-carbon bonds of the
unsaturated fatty acids is done before the glycerol in the lipids
is dissociated from the lipid molecules, a transesterification is
further processed to form ester products. When cracking the double
carbon-carbon bonds of the unsaturated fatty acids is done after
the glycerol in the lipids is dissociated and removed from the
lipid molecules, an esterification is further processed to form
ester products. The boiling points of ester products are much lower
than fatty acids such as ethyl methyl ester (C2H5OCH3) has the
boiling point at 8.degree. C. and propanoic acid (C2H5COOH) has the
boiling point at 141.degree. C. even both products have the same
carbon numbers (3). After the cracking the double carbon-carbon
bonds of the unsaturated fatty acids, aldehyde products (with --CHO
groups) such as hexanal are formed. Aldehyde products can be used
directly. Aldehyde products can also be converted into alkane
products (with --CH3 group) by such as hydrazones, which is called
the Wolff-Kishner reduction. After hexanal is converted into
hexane, the boiling point is reduced from 128.degree. C. (for
hexanal CH3(CH2)4CHO) to 69.degree. C. (for hexane CH3(CH2)4CH2).
Besides glyceryl trialkanoates, carboxylic acids (fatty acids),
phospholipids, glycolipids, and terpenes can be similarly treated
as above. The most valuable products as fuels are the organic or
carbohydrate products with smaller carbon numbers such as less than
15 in the molecular formula and lower boiling points such as lower
than 300.degree. C.
[0015] To crack saturated (single) carbon-carbon bonds of the
saturated acids in plant or animal lipids is difficult. When a
mixture of alkanes from the gas oil materials (C12 and higher) are
heated to very high temperature in the presence of a variety of
catalysts, then the molecular break apart and rearrange to smaller,
more highly branched alkanes containing 5 to 10 carbons. The
cracking can also be done at very high temperature without a
catalyst. But this process to crack saturated single carbon-carbon
bonds tends to have alkanes with unbranched chains (Solomons,
1984).
[0016] After the cracking carbon-carbon bonds and the chemical
reactions to convert such as from the fatty acids into their ester
products with chemicals and catalysts, the mixed products with
carbon numbers from C3 to C18 and higher in the molecular formulas
processed from plant or animal lipids with carbon numbers about C45
to C57 in the molecular formula may considered as biopetroleum.
Then a distillation process is applied to produce the fraction
products according to their boiling points, which is similar to the
distillation process of normal petroleum. The products with low
boiling points are used as better fuels. The products with high
boiling points are used as oils. The nonvolatile products are used
for other applications. The products as fuels are obtained from
distillation process, which are totally different from current
processes for biodiesel products. The products from distillation
process have low molecular weight, low boiling points, and low
viscosity. The method in this invention produces better products
after distillation process.
* * * * *