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1.
Fatty methyl ester hydrogenation to fatty alcohol part I: Correlation between catalyst properties and activity/selectivity 总被引:1,自引:3,他引:1
Ross D. Rieke Deepak S. Thakur Brian D. Roberts Geoffrey T. White 《Journal of the American Oil Chemists' Society》1997,74(4):333-339
Fatty alcohols, derived from natural sources, are commercially produced by hydrogenation of fatty acids or methyl esters in
slurry-phase or fixed-bed reactors. One slurry-phase hydrogenation of methyl ester process flows methyl esters and powdered
copper chromite catalyst into tubular reactors under high hydrogen pressure and elevated temperature. In the present investigation,
slurry-phase hydrogenations of C12 methyl ester were carried out in semi-batch reactions at nonoptimal conditions (i.e., low hydrogen pressure and elevated
temperature). These conditions were used to accentuate the host of side reactions that occur during the hydrogenation. Some
14 side reaction routes are outlined. As an extension of this study, copper chromite catalyst was produced under a number
of varying calcination temperatures. Differences in catalytic activity and selectivity were determined by closely following
side reaction products. Both activity and selectivity correlate well with the crystallinity of the copper chromite surface;
they increase with decreasing crystallinity. The ability to follow the wide variety of side reactions may well provide an
additional tool for the optimized design of hydrogenation catalysts. 相似文献
2.
Synthesis and Surface Active Properties of Sulfonated Acrylate Esters Based on Al‐Cedre Oil
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Wagdy Ibrahim A. El-Dougdoug Mohamed Abo Riya Basma A. Mahy 《Journal of surfactants and detergents》2015,18(4):681-688
Sulfonated acrylate esters have been synthesized by using renewable raw materials such as fatty alcohols of Al‐Ceder oil. Mixed fatty acids were isolated from Al‐Ceder oil by hydrolysis; both saturated and unsaturated fatty acids were isolated from the mixed fatty acids. The methyl esters of mixed fatty acid, saturated and unsaturated acids of Al‐Cedre oil were subjected to reduction with (LiAlH4) to give the corresponding fatty alcohols. The products of the reduction process were saponified and the hydroxyl values were estimated to further confirm the reduction occurrence. The acrylate esters were synthesized by esterification of acrylic acid with fatty alcohols of C16:0, C18:0, C18:1, and C18:2 mixed saturated, mixed unsaturated and mixed fatty acids of Al‐Cedre oil, respectively. This esterification was followed by addition of NaHSO3 to form bisulfite adducts. The structures of the prepared surfactants were characterized by IR and 1HNMR spectroscopy. A series of useful surface parameters, stability towards acids and base hydrolysis and calcium stability have been determined. 相似文献
3.
Manufacture of fatty alcohols based on natural fats and oils 总被引:1,自引:0,他引:1
Udo R. Kreutzer 《Journal of the American Oil Chemists' Society》1984,61(2):343-348
The present worldwide capacity of fatty alcohols is ca. 1.0 million metric tons per year. About 60% of this capacity is based
on petrochemical feedstocks, 40% on natural fats and oils. Three basic dominating commercial-scale processes are used to manufacture
fatty alcohols: the Ziegler process and the Oxo synthesis starting from petrochemical feedstocks, and the high-pressure hydrogenation
of natural fatty acids and esters. Basically, the high-pressure hydrogenation can be used with triglycerides, fatty acids
or fatty acid esters as feedstock. The direct hydrogenation of fats and oils has not been developed to a commercial-scale
process, mainly because it was not possible to prevent decomposition of the valuable byproduct glycerol. Conversion of fatty
acids into fatty alcohols by catalytic hydrogenation without preesterification requires corrosion-resistant materials of construction
and acid-resistant catalysts. Required reaction temperatures are higher, resulting in a higher hydrocarbon content. The majority
of fatty alcohol plants based on natural fats and oils use methyl esters as feedstock. These can be made either by esterification
of fatty acids or by-transesterification of triglycerides. For catalytic high-pressure hydrogenation of methyl esters to fatty
alcohols, several process options have been developed. The bawic distinguishing feature is the catalyst application either
in a fixed bed arrangement or suspended in the methyl ester feed. 相似文献
4.
Recovery of short,medium, and long chain fatty acid methyl esters using wet halogenated hydrocarbons
Fatty acid methyl esters are prepared and analyzed by gas liquid chromatography using a simple procedure that does not involve
evaporation steps or drying of the final extract. The esters of fatty acids down to caproate (C6) are recovered quantitatively. The long chain fatty acid esters, including the polyunsaturated esters, are also recovered
quantitatively and are at least as stable as esters isolated by conventional procedures. Preparation of the esters in methanolic
reagents is followed by partition of the mixture between a small volume of ethylene chloride and a large volume of water.
The lower halogenated hydrocarbon phase contains the methyl esters ready for analysis, and the aqueous phase contains the
methanol, catalysts, and other water-soluble materials. 相似文献
5.
Limanathes douglasii seed oil glycerides contain fatty acids which predominantly (97%) have 20 or more carbon atoms. Fatty acids were prepared
by saponification; fatty alcohols, by sodium reduction of the glycerides; and liquid wax esters, byp-toluenesulfonic acid-catalyzed reaction of the fatty acids with the fatty alcohols. Solid waxes were prepared by hydrogenation
of the glyceride oil and of the wax esters. Chemical and physical constants were determined forLimnanthes douglasii seed oil and its derivatives. The liquid wax esters had properties very similar to those of jojoba (Simmondsia chinensis) seed oil. The solid hydrogenated wax ester was identical in physical appearance and melting point to hydrogenated jojoba
seed oil.
A laboratory of the Northern Utilization Research and Development Division, Agricultural Research Service, USDA. 相似文献
6.
E. W. Bell J. P. Friedrich L. E. Gast J. C. Cowan 《Journal of the American Oil Chemists' Society》1965,42(10):876-878
Saturated C18- and C20-cyclic alcohols have been prepared by catalytic hydrogenation of methyl esters from cyclized linseed monomeric acids, purified
saturated C18-cyclic acids, ethylene adduct of conjugated soybean fatty acids, and ethylene adduct of conjugated octadecadienoic acids.
The cyclic alcohols have also been prepared from free acids of crude cyclic linseed, cyclic linseed monomeric, and ethylene
adduct of 9,11,t,t,-octadecadienoic. Conversion of esters and acids was 88–99% by hydroxyl determination; by gas-liquid chromatographic analysis,
almost quantitative Hydrogenations were carried out with 10%, by weight, copper chromite catalyst, an initial hydrogen pressure
of 2,100 psi, and a temperature of 280C for 3–5 hr.
Preliminary evaluations indicate that saturated C18- and C20-cyclic alcohols have a potential use in cosmetic formulations.
Presented AOCS meeting in Minneapolis, Minn., 1963.
No. Utiliz. Res. & Dev. Div., ARS, USDA. 相似文献
7.
H. M. Teeter E. J. Dufek C. B. Coleman C. A. Glass E. H. Melvin J. C. Cowan 《Journal of the American Oil Chemists' Society》1956,33(9):399-404
Summary A number of vinyl ethers of C18 fatty alcohols have been prepared by reaction of the alcohol with acetylene at atmospheric pressure in the presence of a
basic catalyst. Infrared spectroscopic data on long-chain fatty alcohols, their vinyl ethers, and related chemical derivatives
have been obtained. Methods of analysis of long-chain vinyl ethers for vinyl group have been developed, namely, iodometric,
hydroxylamine, and infrared methods.
Preliminary experiments on the polymerization of long-chain vinyl ethers with ionic catalysts were carried out.
Presented at fall meeting, American Oil Chemists’ Society, Philadelphia, Pa., Oct. 10–12, 1955. 相似文献
8.
Secondary ethers can be obtained from meadow-foam-derived delta lactones or 5-hydroxy fatty acids by using Lewis or Brønsted acid catalysts in good yield (70–90%). The conversion of δ-lactone or 5-hydroxy fatty acid to 5-ethers is performed under atmospheric pressure between 67 and 125°C with 0.5–6.4 mole equivalents of acid catalyst in the presence of 2–40 equivalents of alcohol and a reaction time of 1–140 h. Acid catalysts include mineral acids, such as perchloric and sulfuric; Lewis acids, such as boron trifluoride; and heterogeneous catalysts, such as clays and ion-exchange resins. Primary alcohols, such as methanol, butanol, decanol, and oleyl alcohol, or branched-chain alcohols, such as 2-ethylhexanol, can be used to make secondary ether fatty esters. The 5-ether fatty esters and the process for their formation have not been previously known and appear to be limited to structures where stabilized cations can be formed. The novel ethers were fully characterized by nuclear magnetic resonance and gas chromatography-mass spectrometry. 相似文献
9.
Crambe abyssinica andLunaria annua, members of the Cruciferae family, have seed oil glycerides containing ca. 55–65% of C22 and C24 unsaturated fatty acids. Fatty acids were prepared by saponification; fatty alcohols, by sodium reduction of glycerides;
liquid wax esters, byp-toluenesulfonic acid-catalyzed reaction of fatty acids with fatty alcohols; and methyl esters, by reaction of fatty acids
with diazomethane. Solid hydrogenated glyceride oils and wax esters were compared with several commercial waxes. Chemical
and physical constants were determined for the seed oils and their derivatives. Position of unsaturation in theCrambe fatty acids was determined by gas chromatographic analysis of the permanganate-periodate degradation products. The major
dicarboxylic acid was brassylic (C13), proving the docosenoic acid to be erucic.
Presented in part at the AOCS meeting in New Orleans, La., 1962.
A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, U.S.D.A. 相似文献
10.
Trans-α,β-Unsaturated Fatty Acids and Products formed by their Reduction with Lithium-Aluminium-Hydride and Di-isobutyl-Aluminium-Hydride A method for the preparation of pure methyl esters of α,β-unsaturated fatty acids is described. The reduction of these esters with LiAlH4 led to poor yields of α,β-unsaturated alcohols. Saturated alkanols and aldehydes were mainly formed. Di-isobutyl aluminium hydride gave near quantitative yields of α,β-unsaturated alcohols. The reaction was studied with the help of gas chromatography using strongly polar stationary phases. 相似文献
11.
Detection of the Methyl Esters of Saturated Cycloaliphatic and Aromatic Fatty Acids with Thin-layer and Gas Chromatography Homologous series of methyl esters of saturated cycloaliphatic (CFA) and aromatic fatty acids (AFA), which were prepared by the alkali isomerisation of fish oil followed by hydrogenation and fractionation of the cyclised mixture as well as with the help of cyclising hydrogenation, were analysed by thin-layer and gas chromatography. Even 0.4% CFA and AFA, which do not form urea-adducts, can be detected in the fractions as a substance class in thin-layer chromatography. The equivalent carbon numbers (stearic acid = 18) of the principal isomers of CFA and AFA homologues (C18 to C22), which were obtained as a class in the thin-layer chromatographic separation, were determined by the gas chromatography. 相似文献
12.
A concentrate of branched chain fatty acids (as methyl esters) was prepared from the triacylglycerols of subcutaneous adipose
tissue lipids of lambs receiving a carbohydrate-rich (cereal) diet. This was accomplished by procedures which allowed the
removal of unsaturated components by peroxidation and straight chain saturated components by urea-adduct formation. The concentrate
was analyzed by high resolution gas chromatography in combination with mass spectrometry and was shown to consist of a complex
mixture of saturated methyl-substituted fatty acids. Methyl substitution occurred on even-numbered carbon atoms (relative
to the carboxyl group) and the chain lengths of the acids ranged from 10 to 18 carbon atoms. Acids with one methyl substituent
in the fatty acyl chain were most abundant; di-, tri- and tetramethyl-substituted acids were also present. The biosynthesis
of these methyl-substituted acids is discussed briefly. 相似文献
13.
W. E. Link H. M. Hickman R. A. Morrissette 《Journal of the American Oil Chemists' Society》1959,36(7):300-303
Conclusions Gas-liquid chromatography has been shown to be applicable to the analysis of fatty alcohols. Through the use of polyester
columns these alcohols have been separated according to chain length and degree of unsaturation. A study has been made of
the relationship between peak areas of the chromatograms and the actual weight percentages of the four C18 alcohols found in the fatty alcohols derived from linseed oil. Fatty alcohols, prepared from soybean, linseed, and sperm
oil have been prepared and analyzed by the proposed procedure.
Craig and Murty (1) have recently reported that polyesters based on succinic acid are preferable for the liquid phase of the
chromatographic column to those made from adipic in that they afford a better separation of methyl stearate from methyl oleate.
Conversely adipic columns gave a more effective separation of the esters of linolenic and arachidic acids.
The application of these polyesters to the analysis of fatty alcohol acetates is expected to improve their separation in a
similar fashion, but further work is indicated in the search for a liquid phase that will permit both separations in the minimum
time.
ADM Technical Talk No. 166. 相似文献
14.
Products of Dimerisation Unsaturated Fatty Acids VIII: The Fraction of “Intermediates” Obtained by Dimerisation of Unsaturated Fatty Acids The fraction of “intermediates” which is obtained by dimerisation of unsaturated fatty acid contains straight chain saturated fatty acids with 20-24 carbon atoms as well as methyl branched isomers thereof. The production of these compounds is probably caused by the presence of small amounts of monounsaturated fatty acids with 20-24 carbon atoms in the starting material. The fraction of “intermediates” contains in addition monocarboxylic acids with 36 carbon atoms. These are probably formed after dimerisation by an intramolecular cyclisation reaction under participation of one carboxylic group, followed by hydrogenation of the produced carbonyl group. Finally the formed alcoholic group is eliminated as a water molecule, and the produced double bond is hydrogenated. 相似文献
15.
H. Bertsch H. Reinheckel K. Haage 《European Journal of Lipid Science and Technology》1969,71(5):357-362
Reduction of Unsaturated Fatty Acids and Their Esters to Unsaturated Fatty Alcohols by Selective Catalytic High Pressure Hydrogenation III: Metallic and Metal Oxide Copper-Chromium Catalysts Influence of catalyst composition and reaction conditions on the high pressure reduction of unsaturated fatty acids and their esters is described for metallic and mixed metal oxide copper-chromium catalysts. From these investigations and from a comparison with the efficacy of other metals in hydrogenation a hypothesis on the mechanism of the catalytic reaction in the reduction of carboxyl group and saturation of C? C double bonds is developed. The optimum reaction data of oleic acid and methyl oleate, which were used as test substances, are given. 相似文献
16.
Maria A. Sánchez Vanina A. Mazzieri Mario R. Sad Ricardo Grau Carlos L. Pieck 《Journal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986)》2011,86(3):447-453
BACKGROUND: Improvements in the selective hydrogenation of unsaturated fatty acid methyl esters in order to obtain unsaturated fatty alcohols have been attempted through the preparation and modification of supported group VIII metallic catalysts. Suitable catalysts appear to be those based on supported Ru modified by Sn. The influence of preparation and activation methods on the structural and electronic properties of the metallic phase and the effect of modifications to these properties on the catalytic performance of Ru? Sn/Al2O3 catalysts was studied regarding selective hydrogenation of carbonyl groups. RESULTS: Preparation methods have a marked influence on the electronic state of Ru and its interaction with Sn. Temperature‐programmed reduction (TPR), Fourier transform infrared spectroscopy of chemisorbed CO (FTIR‐CO) and X‐ray photoelectron spectroscopy (XPS) results clearly show that the incorporation of sodium borohydride in the preparation leads to a greater Ru? Sn interaction when compared with catalysts prepared by co‐impregnation without B. The activation of catalysts without B (either by direct reduction or calcinations‐reduction) does not produce a strong Ru? Sn interaction. B‐containing catalysts exhibit higher hydrogenolytic and lower dehydrogenating activities. Selectivity towards oleyl alcohol formation was 37% for this catalyst, while catalysts without B were not suitable for obtaining fatty alcohols. CONCLUSION: The degree of interaction between Ru and Sn strongly depends on catalyst preparation and activation method where strong interaction promotes selectivity with respect to oleyl alcohol formation. On the contrary, catalysts with a weak Ru? Sn interaction do not show significant selectivity for the unsaturated alcohol. Copyright © 2010 Society of Chemical Industry 相似文献
17.
U. Imhoff G. Kelbch A. Pastura 《European Journal of Lipid Science and Technology》1977,79(12):480-483
Gas Chromatographic and Thin-Layer Chromatographic Studies on Fatty Acids: The Application of Packed Glass Capillary Columns for Separation of cis- and trans-Unsaturated Fatty Acids from Saturated Fatty Acids Packed glass capillary columns were used for the quantitative determination of trans- and cis-unsaturated fatty acids in the presence of saturated fatty acids by gas chromatography. The fatty acids were analyzed as methyl esters after interesterification of the triglyceride samples. The conversion of glyceryl esters of fatty acids into methyl esters could be followed using short GC columns and by thin-layer chromatography. 相似文献
18.
A. Behr N. Dring Susanne Durowicz-Heil B. Ellenberg Christiane Kozik Ch. Lohr H. Schmidke 《European Journal of Lipid Science and Technology》1993,95(1):2-12
Selective Hydrogenation of Multi-Unsaturated Fatty Acids in the Liquid Phase Fatty acids and esters which contain only one double bond have interesting properties such as high oxidation stability or favourable pour points. For these reasons such products find a broad field of application for instance in the sections cosmetics, textile finishing agents or oilfield chemicals. However, natural fats and oils contain often multi-unsaturated fatty acids such as linoleic and linoleinic acid which are able - even in minor amounts - to change substantially the physical and chemical properties of the fatty material. Therefore, a hydrogenation procedure is needed which enables the selective conversion of multi-unsaturated into mono-unsaturated fatty acids without formation of completely saturated compounds. After a review of the general possibilities in selective hydrogenation a new method is described to hydrogenate with solvent-stabilized palladium colloid catalysts. A remarkable high selectivity was obtained applying very mild reaction conditions. By use of the liquid-liquid two phase technique an easy and complete catalyst recycle is possible. 相似文献
19.
Samuel J. Friedberg 《Lipids》1976,11(8):587-593
Previous studies have shown that ingested fatty alcohols are absorbed as fatty acids and fatty acid esters, particularly triglycerides.
The present study was carried out to determine whether fatty alcohols are also transported as 0-alkyl glyceryl ethers, alk-1-enyl
glyceryl ethers, and as wax esters. Oxidation of fatty alcohols to other lipids was assessed by using a mixture of [1-3H] hexadecanol and [1-14C] hexadecanol of predetermined ratio. The results indicate that the absorption of fatty alcohol, and of its transport forms,
parallels the absorption of labeled fatty acids. Six to 25% of plasma radioactivity was present as 1-0-alkyl diacylglyceryl
ethers with a smaller proportion of ether lipids in the phospholipid fraction. In addition, 4–13% of the ingested hexadecanol
appeared in the plasma as a material having the chromatographic properties of wax ester. Fatty alcohols were not detected
in the plasma as alk-1-enyl lipids. 相似文献
20.
Production and Properties of Fatty Acid Polyglycol Ester Sulfates Fatty alcohol oxethylates, produced by reaction of fatty alcohols from hydrogenated fatty acid methyl esters with ethylene oxide, are the basic material for an important class of anionic tensides, the fatty alcohol ether sulfates. The fatty acid polyglycol ester sulfates are a very interesting alternative to the fatty alcohol ether sulfates. The former are available by saving hydrogenation, in principle directly by fatty acid oxethylation or interesterification of fatty acids with polyglycols, followed by sulfatation. We report about the production of fatty acid ester sulfates by sulfatation of the fatty acid polyglycol monoesters by sulfurtrioxide or chlorosulfonic acid. By means of the results of physicochemical measurements and process trials it is discussed how far fatty acid polyglycol monoester sulfates are suited as alternative tenside raw material fatty alcohol ether sulfates. 相似文献