EP1015407A1 - Method of making hydrogenated acids - Google Patents

Method of making hydrogenated acids

Info

Publication number
EP1015407A1
EP1015407A1 EP98948068A EP98948068A EP1015407A1 EP 1015407 A1 EP1015407 A1 EP 1015407A1 EP 98948068 A EP98948068 A EP 98948068A EP 98948068 A EP98948068 A EP 98948068A EP 1015407 A1 EP1015407 A1 EP 1015407A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
acids
oil
mixture
fatty acids
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP98948068A
Other languages
German (de)
French (fr)
Other versions
EP1015407A4 (en
Inventor
Donald V. Kinsman
J. Matthew White
David J. Anneken
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel Corp
Original Assignee
Henkel Corp
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 Henkel Corp filed Critical Henkel Corp
Publication of EP1015407A1 publication Critical patent/EP1015407A1/en
Publication of EP1015407A4 publication Critical patent/EP1015407A4/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • 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 glycerine is separated and refined in a separate operation.
  • the crude, split fatty acids are usually then distilled to remove color bodies and odoriferous materials.
  • This sequence of splitting and distilling yields the most basic tallow and coconut fatty acids which are widely used for preparing bar soaps.
  • This basic type of coconut fatty acids also finds use in the preparation of a variety of types of surfactants. While these simple split and distilled tallow and coconut fatty acids do have wide use, many in the soap and detergents industry prefer materials with improved colors, color stabilities and odors. These improvements are often effected by hydrogenation.
  • the hydrogenation is a partial hydrogenation. It is generally controlled so as to reduce or totally eliminate the poiyunsaturated acids which are inevitably present in split tallows. Reducing or eliminating the polyunsaturates can significantly improve the color stability of the fatty acids and many soap producers find that this carries through to improving the storage properties of their soap bars.
  • the hydrogenation process also improves the initial color and odor of the partially hydrogenated fatty acids and this also is generally found to carry through to bar soaps.
  • the typical catalyst used for hydrogenation is some type of nickel catalyst and it is a nonselective catalyst.
  • Hydrogenated carboxylic acids are made by a process which comprises contacting a mixture of saturated and unsaturated carboxylic acids with a catalyst effective amount of a hydrogenation catalyst and in the presence of an effective amount of an adsorbent to produce a hydrogenated product having less than about 200 ppm of oxygenated by-products.
  • the process may also be carried out by first contacting a mixture of saturated and unsaturated carboxylic acids with a catalyst effective amount of a hydrogenation catalyst to form a hydrogenated product containing oxygenated by-products and then contacting the hydrogenated product with an effective amount of an adsorbent to produce a hydrogenated product having less than about 200 ppm of oxygenated byproducts.
  • the process according to the invention can be applied to the production of any carboxylic acid made by the hydrogenation of a mixture of saturated and unsaturated carboxylic acids.
  • the simplest example is the production of hydrogenated propionic acid having less than about 200 ppm of oxygenated compounds by the hydrogenation of a mixture of acrylic and propionic acids
  • the process according to the invention is particularly useful for the commercial production of hydrogenated fatty acids wherein the presence of oxygenated compounds could have a deleterious effect on products and/or processes utilizing such acids.
  • hydrogenated stearic acid made by fully hydrogenating mixtures of saturated and unsaturated tallow fatty acids. Hydrogenation converts these mixtures which contain C 18 unsaturated acids to stearic acid.
  • oxygenated compounds such as alcohols, acids and lactones may be formed.
  • the reduction step is typically carried out by contacting the acid mixture with hydrogen in the presence of a catalyst.
  • the typical catalyst used for hydrogenation is some type of nickel catalyst and it is a nonselective catalyst.
  • a mixture of saturated and unsaturated carboxylic acids is contacted with a catalyst effective amount of a hydrogenation catalyst to produce a hydrogenated product which may contain oxygenated compounds.
  • the hydrogenated product is then contacted with an effective amount of an adsorbent to decrease the amount of any oxygenated compounds to less than about 200 ppm.
  • a mixture of saturated and unsaturated carboxylic acids with a catalyst effective amount of a hydrogenation catalyst and in the presence of an effective amount of an adsorbent to produce a hydrogenated product having less than about 200 ppm of oxygenated by-products can be present as part of the catalyst as, for example, the catalyst support or it can be added separately at the beginning of the hydrogenation.
  • the mixture of saturated and unsaturated carboxylic acids can be composed of any type of saturated and unsaturated carboxylic acids. Since the process according to the invention is particularly useful for the commercial production of hydrogenated fatty acids, it can be utilized with a fatty acid stream from the processing of any type of fat or oil.
  • the mixture of carboxylic acids can be a crude fatty acid stream following the splitting or hydrolysis of tallow or coconut oil. Tallow fatty acids will typically contain somewhere around 50 to 52% unsaturated acids of which all but a few percent, maybe 4% or less, are C 1 ⁇ unsaturated acids. Simple split coconut fatty acids contain around 15% of C ⁇ acids.
  • the mixture of saturated and unsaturated carboxylic acids is solvent separated stearic acid.
  • the mixture of saturated and unsaturated acids may also be obtained from the hydrolysis of sunflower oil, palm oil, tall oil, soybean oil and canola oil.
  • Solvent separated stearic acids are obtained by dissolving tallow fatty acids in a solvent and then passing them through chilled crystallizers where the solid, saturated acids crystallize out to form a slurry which is then filtered. Not all the unsaturated acids are removed by filtration so the crude stearic is subjected to some combination of hydrogenation and distillation combination to produce single, double and triple pressed stearic.
  • the catalyst that can be used in the process according to the invention can be any catalyst useful for hydrogenating unsaturated compounds.
  • Such catalysts include but are not limited to platinum, palladium and nickel.
  • the preferred catalyst is nickel.
  • the most preferred catalyst is nickel on acid clay, a commercially available example of which is E-428D from Calsicat; Mallinckrodt Inc., Calsicat Div., 1707 Gaskeil Ave., Erie, PA, 16503.
  • the amount of catalyst that can be used in the process according to the invention is an effective amount which is any amount necessary to bring about the desired degree of hydrogenation.
  • An effective amount will be readily determinable by one of ordinary skill in the art and may depend upon such factors as, for example, the composition of the starting material, the composition of the catalyst, and the hydrogenation temperature.
  • the catalyst amount will typically vary from about 0.7 ppt to about 3.5 ppt (ppt is parts catalyst per thousand parts of carboxylic acid).
  • the mixture of saturated and unsaturated carboxylic acids can be contacted with a catalyst effective amount of a hydrogenation catalyst at a temperature in the range of from about 180°C to about 240°C, preferably from about 190°C to about 230°C, and most preferably from about 200°C to about 220°C.
  • the adsorbent that can be used in the process according to the invention can be carbon black, a commercially available example of which is DARCO® KB from Norit Americas, Inc., 1050 Crown Pointe Parkway, Suite 1500, Atlanta, GA,
  • an amount of the adsorbent is used.
  • the effective amount is any amount necessary to decrease the amount of the oxygenated compounds to less than about 200 ppm as determined, for example, by integration of the methylene proton peaks in the 4.9-5.0 ⁇ region of the H 1 NMR spectrum.
  • Any analytical method known to those of ordinary skill in the art useful for the determination of oxygenated by-products as identified herein can be used.
  • the preferred method is by integration of the methylene proton peaks in the 4.9- 5.0 ⁇ region of the H 1 NMR spectrum as described in Example 2 below.
  • a concentration of 200 ppm is the approximate threshold level for detection of oxygenated by-products in the PFT H 1 NMR spectrum.
  • EXAMPLE 1 A sample of crude solvent separated stearic acid was hydrogenated to an iodine value of less than 1 with varying amounts of nickel on acid clay catalyst (E-428D) and a clay adsorbent (Filtrol 13) under the hydrogenation conditions of 205 °C, 1 hour and 300 psi hydrogen. The samples were then filtered over dicalite and distilled under a vacuum of 1-3 torr, 1 % top cut and a pot temperature of 250°C and their H 1 NMR spectra were taken.
  • the hydrogenation was accomplished using a low catalyst concentration and no added adsorbent.
  • the catalyst and adsorbent were present as one component in that the nickel catalyst was deposited on acid clay which also functioned as the adsorbent. No additional adsorbent was added. Peaks were observed at 4.9-5.0 ⁇ in the H 1 NMR spectrum indicating the presence of oxygenated by-products at a level equal to or greater than 200 ppm.
  • the hydrogenation was accomplished using an elevated catalyst level and a corresponding elevated adsorbent level as the catalyst support compared with the control but no separately added adsorbent.
  • EXAMPLE 2 The H 1 PFT NMR spectra of the samples in deuterochloroform solvent from Example 1 were obtained using a Varian Unity 400 spectrometer. At least 1000 pulses were collected for each spectra. The spectra were expanded at least 1000 times in order to detect peaks in the 4.9-5.0 ⁇ region. The concentration of the 4.9-5.0 peaks was estimated by comparing it to the -CH 2 CO 2 - peaks between 2.3 and 2.4 ⁇ .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

A mixture of saturated and unsaturated carboxylic acids are hydrogenated with an effective amount of a hydrogenation catalyst and in the presence of an effective amount of an adsorbent to produce a hydrogenated product having less than about 200 ppm of oxygenated by-products.

Description

TITLE OF THE INVENTION: Method of Making Hydrogenated Acids
BACKGROUND OF THE INVENTION: Mixtures of saturated and unsaturated carboxylic acids are conveniently converted to products substantially free of unsaturation by means of catalytic hydrogenation. Such a process is particularly useful in the commercial production of fatty acids, compounds which are used to make base stocks for soap production, as intermediate raw materials for producing a wide range of surfactants, as foam control agents and precipitants in a variety of cleaning products, as superfatting agents in personal cleansing bars, as softener components, and for a number of other more specialized purposes. Fatty acids are obtained from fats and oils by a process the first step of which is referred to as splitting. Splitting is the hydrolysis of a fat or oil to form three molecules of fatty acid and one molecule of glycerine. The glycerine is separated and refined in a separate operation. The crude, split fatty acids are usually then distilled to remove color bodies and odoriferous materials. This sequence of splitting and distilling yields the most basic tallow and coconut fatty acids which are widely used for preparing bar soaps. This basic type of coconut fatty acids also finds use in the preparation of a variety of types of surfactants. While these simple split and distilled tallow and coconut fatty acids do have wide use, many in the soap and detergents industry prefer materials with improved colors, color stabilities and odors. These improvements are often effected by hydrogenation.
In the case of tallow the hydrogenation is a partial hydrogenation. It is generally controlled so as to reduce or totally eliminate the poiyunsaturated acids which are inevitably present in split tallows. Reducing or eliminating the polyunsaturates can significantly improve the color stability of the fatty acids and many soap producers find that this carries through to improving the storage properties of their soap bars. The hydrogenation process also improves the initial color and odor of the partially hydrogenated fatty acids and this also is generally found to carry through to bar soaps. The typical catalyst used for hydrogenation is some type of nickel catalyst and it is a nonselective catalyst. That means that besides reducing poiyunsaturated acids to monounsaturated acids - basically oleic acids - it also reduces some amount of unsaturated acid to saturated acid - basically stearic acid. During the hydrogenation step, oxygenated compounds such as alcohols, acids and lactones may be formed which can have a deleterious effect on products and/or processes utilizing such acids. For example, the presence of alcoholic impurities could interfere with the production of acid chlorides. BRIEF SUMMARY OF THE INVENTION:
Hydrogenated carboxylic acids are made by a process which comprises contacting a mixture of saturated and unsaturated carboxylic acids with a catalyst effective amount of a hydrogenation catalyst and in the presence of an effective amount of an adsorbent to produce a hydrogenated product having less than about 200 ppm of oxygenated by-products. The process may also be carried out by first contacting a mixture of saturated and unsaturated carboxylic acids with a catalyst effective amount of a hydrogenation catalyst to form a hydrogenated product containing oxygenated by-products and then contacting the hydrogenated product with an effective amount of an adsorbent to produce a hydrogenated product having less than about 200 ppm of oxygenated byproducts. BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING:
Not Applicable.
DETAILED DESCRIPTION OF THE INVENTION:
The process according to the invention can be applied to the production of any carboxylic acid made by the hydrogenation of a mixture of saturated and unsaturated carboxylic acids. The simplest example is the production of hydrogenated propionic acid having less than about 200 ppm of oxygenated compounds by the hydrogenation of a mixture of acrylic and propionic acids
(propenoic and propanoic acids). The process according to the invention is particularly useful for the commercial production of hydrogenated fatty acids wherein the presence of oxygenated compounds could have a deleterious effect on products and/or processes utilizing such acids. For example, hydrogenated stearic acid made by fully hydrogenating mixtures of saturated and unsaturated tallow fatty acids. Hydrogenation converts these mixtures which contain C18 unsaturated acids to stearic acid. During the hydrogenation step, oxygenated compounds such as alcohols, acids and lactones may be formed. The reduction step is typically carried out by contacting the acid mixture with hydrogen in the presence of a catalyst. The typical catalyst used for hydrogenation is some type of nickel catalyst and it is a nonselective catalyst. That means that besides reducing poiyunsaturated acids to monounsaturated acids - basically oleic acids - it also reduces some amount of unsaturated acid to saturated acid - basically stearic acid. There is also some conversion of cis-unsaturated acids to trans- unsaturated acids.
The process according to the invention can be carried out in either of two ways. In one embodiment, a mixture of saturated and unsaturated carboxylic acids is contacted with a catalyst effective amount of a hydrogenation catalyst to produce a hydrogenated product which may contain oxygenated compounds. The hydrogenated product is then contacted with an effective amount of an adsorbent to decrease the amount of any oxygenated compounds to less than about 200 ppm.
In another embodiment, a mixture of saturated and unsaturated carboxylic acids with a catalyst effective amount of a hydrogenation catalyst and in the presence of an effective amount of an adsorbent to produce a hydrogenated product having less than about 200 ppm of oxygenated by-products. In this embodiment, the adsorbent can be present as part of the catalyst as, for example, the catalyst support or it can be added separately at the beginning of the hydrogenation.
The mixture of saturated and unsaturated carboxylic acids can be composed of any type of saturated and unsaturated carboxylic acids. Since the process according to the invention is particularly useful for the commercial production of hydrogenated fatty acids, it can be utilized with a fatty acid stream from the processing of any type of fat or oil. For example, the mixture of carboxylic acids can be a crude fatty acid stream following the splitting or hydrolysis of tallow or coconut oil. Tallow fatty acids will typically contain somewhere around 50 to 52% unsaturated acids of which all but a few percent, maybe 4% or less, are C1β unsaturated acids. Simple split coconut fatty acids contain around 15% of C^ acids. In one embodiment of the process according to the invention, the mixture of saturated and unsaturated carboxylic acids is solvent separated stearic acid. The mixture of saturated and unsaturated acids may also be obtained from the hydrolysis of sunflower oil, palm oil, tall oil, soybean oil and canola oil. Solvent separated stearic acids are obtained by dissolving tallow fatty acids in a solvent and then passing them through chilled crystallizers where the solid, saturated acids crystallize out to form a slurry which is then filtered. Not all the unsaturated acids are removed by filtration so the crude stearic is subjected to some combination of hydrogenation and distillation combination to produce single, double and triple pressed stearic. The catalyst that can be used in the process according to the invention can be any catalyst useful for hydrogenating unsaturated compounds. Such catalysts include but are not limited to platinum, palladium and nickel. The preferred catalyst is nickel. The most preferred catalyst is nickel on acid clay, a commercially available example of which is E-428D from Calsicat; Mallinckrodt Inc., Calsicat Div., 1707 Gaskeil Ave., Erie, PA, 16503.
The amount of catalyst that can be used in the process according to the invention is an effective amount which is any amount necessary to bring about the desired degree of hydrogenation. An effective amount will be readily determinable by one of ordinary skill in the art and may depend upon such factors as, for example, the composition of the starting material, the composition of the catalyst, and the hydrogenation temperature. When the process according to the invention is used to make hydrogenated fatty acids, the catalyst amount will typically vary from about 0.7 ppt to about 3.5 ppt (ppt is parts catalyst per thousand parts of carboxylic acid).
The mixture of saturated and unsaturated carboxylic acids can be contacted with a catalyst effective amount of a hydrogenation catalyst at a temperature in the range of from about 180°C to about 240°C, preferably from about 190°C to about 230°C, and most preferably from about 200°C to about 220°C.
The adsorbent that can be used in the process according to the invention can be carbon black, a commercially available example of which is DARCO® KB from Norit Americas, Inc., 1050 Crown Pointe Parkway, Suite 1500, Atlanta, GA,
30338; silica, alumina, or clay such as kaolinite, montmorillonite, bentonite, atapulgite, illite and halloysite, a commercially available example of which is FILTROL® Grade 13, Harshaw/Filtrol, 30100 Chagrin Boulevard, Cleveland, OH, 44124. In each embodiment of the present invention as described above, an amount of the adsorbent is used. The effective amount is any amount necessary to decrease the amount of the oxygenated compounds to less than about 200 ppm as determined, for example, by integration of the methylene proton peaks in the 4.9-5.0 δ region of the H1 NMR spectrum. Any analytical method known to those of ordinary skill in the art useful for the determination of oxygenated by-products as identified herein can be used. The preferred method is by integration of the methylene proton peaks in the 4.9- 5.0 δ region of the H1 NMR spectrum as described in Example 2 below. A concentration of 200 ppm is the approximate threshold level for detection of oxygenated by-products in the PFT H1 NMR spectrum.
The following examples are meant to illustrate but not to limit the invention. EXAMPLE 1 A sample of crude solvent separated stearic acid was hydrogenated to an iodine value of less than 1 with varying amounts of nickel on acid clay catalyst (E-428D) and a clay adsorbent (Filtrol 13) under the hydrogenation conditions of 205 °C, 1 hour and 300 psi hydrogen. The samples were then filtered over dicalite and distilled under a vacuum of 1-3 torr, 1 % top cut and a pot temperature of 250°C and their H1 NMR spectra were taken.
In the control sample (1 ), the hydrogenation was accomplished using a low catalyst concentration and no added adsorbent. The catalyst and adsorbent were present as one component in that the nickel catalyst was deposited on acid clay which also functioned as the adsorbent. No additional adsorbent was added. Peaks were observed at 4.9-5.0 δ in the H1 NMR spectrum indicating the presence of oxygenated by-products at a level equal to or greater than 200 ppm. In the case of sample (2), the hydrogenation was accomplished using an elevated catalyst level and a corresponding elevated adsorbent level as the catalyst support compared with the control but no separately added adsorbent. No peaks were observed at 4.9 -5.0 δ in the H1 NMR spectrum indicating that the level of oxygenated by-products was less than 200 ppm. In the sample (3), the hydrogenation was accomplished using the low catalyst level of the control but in the presence of added adsorbent. No peaks were observed at 4.9 -5.0 δ in the
H1 NMR spectrum indicating that the level of oxygenated by-products was less than 200 ppm. The results as reported in Table 1 below. From Table 1 it is seen that when hydrogenations are carried out in the presence of an effective amount of an adsorbent (samples 2 and 3) which is present either as the catalyst support or added separately, the concentration of the oxygenated by-products is less than 200 ppm.
7 TABLE 1
SarrtDle No. 428D Catalvst Cone* Filtrol 13 Cone* Cone. 4.9-5.0 δ
1 1.0 ppt — 0.02%
2 1.7ppt - not detected
3 LOppt 0.7ppt not detected
*-ppt is parts per thousand parts of carboxylic acid
EXAMPLE 2 The H1 PFT NMR spectra of the samples in deuterochloroform solvent from Example 1 were obtained using a Varian Unity 400 spectrometer. At least 1000 pulses were collected for each spectra. The spectra were expanded at least 1000 times in order to detect peaks in the 4.9-5.0 δ region. The concentration of the 4.9-5.0 peaks was estimated by comparing it to the -CH2CO2- peaks between 2.3 and 2.4 δ.

Claims

What is claimed is:
1. A process which comprises contacting a mixture of saturated and unsaturated carboxylic acids with an effective amount of a hydrogenation catalyst and in the presence of an effective amount of an adsorbent to produce a hydrogenated product having less than about 200 ppm of oxygenated byproducts.
2. The process of claim 1 where the catalyst is nickel on acid clay.
3. The process of claim 1 wherein the amount of the catalyst is from about 0.7 to about 3.5 parts catalyst per thousand parts of carboxylic acid mixture.
4. The process of claim 1 wherein the process is carried out at a temperature of from about 180┬░C to about 240┬░C.
5. The process of claim 4 wherein the temperature is from about 190┬░C to about 230╬▓C.
6. The process of claim 5 wherein the temperature is from about 200 ┬░C to about 220┬░C.
7. The process of claim 1 wherein the adsorbent is carbon black, silica, alumina or clay.
8. The process of claim 1 wherein the mixture of saturated and unsaturated carboxylic acids is comprised of fatty acids.
9. The process of claim 8 wherein the fatty acids are derived from tallow or coconut oil.
10. The process of claim 8 wherein the fatty acids are derived from sunflower oil, palm oil, tall oil, soybean oil or canola oil.
11. A process comprising the steps of: (1 ) contacting a mixture of saturated and unsaturated carboxylic acids with an effective amount of a hydrogenation catalyst to produce a reduced product comprised of oxygenated by-products; (2) contacting said hydrogenated acid with an effective amount of an adsorbent to decrease the amount of said oxygenated compounds to less than about 200 ppm.
12. The process of claim 11 where the catalyst is nickel on acid clay.
13. The process of claim 11 wherein the amount of the catalyst is from about 0.7 to about 3.5 parts catalyst per thousand parts of carboxylic acid mixture.
14. The process of claim 11 wherein the process is carried out at a temperature of from about 180┬░C to about 240┬░C.
15. The process of claim 14 wherein the temperature is from about 190┬░C to about 230┬░C.
16. The process of claim 15 wherein the temperature is from about 200┬░C to about 220 ┬░C.
17. The process of claim 11 wherein the adsorbent is carbon black, silica, alumina or clay.
18. The process of claim 11 wherein the mixture of saturated and unsaturated carboxylic acids is comprised of fatty acids.
19. The process of claim 18 wherein the fatty acids are derived from tallow or coconut oil.
20. The process of claim 18 wherein the fatty acids are derived from sunflower oil, palm oil, tall oil, soybean oil or canola oil.
EP98948068A 1997-09-05 1998-09-02 Method of making hydrogenated acids Withdrawn EP1015407A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US92581197A 1997-09-05 1997-09-05
US925811 1997-09-05
PCT/US1998/017989 WO1999012882A1 (en) 1997-09-05 1998-09-02 Method of making hydrogenated acids

Publications (2)

Publication Number Publication Date
EP1015407A1 true EP1015407A1 (en) 2000-07-05
EP1015407A4 EP1015407A4 (en) 2000-11-08

Family

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EP98948068A Withdrawn EP1015407A4 (en) 1997-09-05 1998-09-02 Method of making hydrogenated acids

Country Status (4)

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EP (1) EP1015407A4 (en)
AU (1) AU9471898A (en)
CA (1) CA2302609A1 (en)
WO (1) WO1999012882A1 (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB999882A (en) * 1961-08-31 1965-07-28 Shell Int Research Process for the purification of monocarboxylic acids
DD156176A1 (en) * 1981-02-05 1982-08-04 Wolfgang Lambrecht HYDROGENATION METHOD FOR OBTAINING LIQUID FATS
EP0398668A1 (en) * 1989-05-16 1990-11-22 Unichema Chemie B.V. Nickel/silica catalyst and the preparation and use thereof
US5493037A (en) * 1992-11-10 1996-02-20 Engelhard Corporation Nickel catalyst

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5693835A (en) * 1994-01-27 1997-12-02 Snow Brand Milk Products Co., Ltd. Fish oil having decreased fish odor and a method for preparing the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB999882A (en) * 1961-08-31 1965-07-28 Shell Int Research Process for the purification of monocarboxylic acids
DD156176A1 (en) * 1981-02-05 1982-08-04 Wolfgang Lambrecht HYDROGENATION METHOD FOR OBTAINING LIQUID FATS
EP0398668A1 (en) * 1989-05-16 1990-11-22 Unichema Chemie B.V. Nickel/silica catalyst and the preparation and use thereof
US5493037A (en) * 1992-11-10 1996-02-20 Engelhard Corporation Nickel catalyst

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO9912882A1 *

Also Published As

Publication number Publication date
EP1015407A4 (en) 2000-11-08
CA2302609A1 (en) 1999-03-18
AU9471898A (en) 1999-03-29
WO1999012882A1 (en) 1999-03-18

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