Oleochemical products as building blocks for polymers

Heidbreder, Andreas; Höfer, Rainer; Grützmacher, Roland; Westfechtel, Alfred; Blewett, C. William

doi:10.1002/(sici)1521-4133(199911)101:11<418::aid-lipi418>3.0.co;2-x

Cited by 35 publications

(19 citation statements)

References 3 publications

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“…The dimerisation of unsaturated acids from talI oil, soybean oil or technical oleic acid occurs at 230-260°C with a montmorillonite clay as a catalyst [30,31].This reaction is used in the production of dimeric fatty acids. Brat et al [32] investigated the kinetic of this reaction and found out that the addition of 1-2% water, 4-6% Bentonite during heating for 2-8 hours is the optimum.…”

Section: Resultsmentioning

confidence: 99%

A new method to determine oxidative stability of vegetable fats and oils at simulated frying temperature

Gertz

Kochhar

2001

OCL

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Summary :A new procedure at simulated frying conditions in our laboratory was developed to monitor frying stability of fats and oils. Water-conditioned silica was prepared and added to the fresh vegetable oil, which was heated for two hours at 170°C. The oil stability at frying temperature was then evaluated by determining the amount of formed dimeric triglycerides The results obtained showed that the stability of the vegetable oils at frying temperature could not be explained by the fatty acid composition alone. Corn oil was observed to be more stable than soybean oil, and rapeseed oil was better than olive oil. It was also observed that crude, non-refined oils were found to have a better heat stability than refin-ed oils. To estimate the effectiveness of synthetic and naturally occurring antioxidants, namely various tocopherols, tocopherol acetate and phytosterol fractions, phenolic compounds like quercetin, oryzanol, ferulic acid, gallates, BHT, BHA and other compounds like ascorbic acid 6-palmitate and squalene were added to refined sunflower and rape seed oil, and their oxidative stability at elevated temperature (OSET) values determined. Both linoleic and oleic rich oils gave comparable results for the activity of the various compounds. alpha-tocopherol, tocopherol esters and BHA had low effects on oil stability at frying temperature, while ascorbyl palmitate and some phytosterol fractions were found to have the most stabilizing activity under frying conditions. Keywords : oxidative stability, heat stability, deep frying, antioxidant, natural components. ARTICLEDuring deep-frying, the fat and oil decompose forming volatile, non-volatile, monomeric and polymeric, oxidised or non-oxidised compounds. Their amounts and chemical structures depend on the nature of fat or oil used, the temperature, frying time, the food (of what moisture content) being fried, and on the accessibility of air (oxygen). Deep frying is a complex phenomenon where water, oxygen and heat are the main factors, which determine the kinetics of oxidation and polymerisation processes.Article disponible sur le site http://www.ocl-journal.org ou http://dx

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Section: Resultsmentioning

confidence: 99%

A new method to determine oxidative stability of vegetable fats and oils at simulated frying temperature

Gertz

Kochhar

2001

OCL

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“…Additionally, DFA derived polyurethanes were reported to show improved hydrolytic and oxidative stability. [10] Finally, DFA are also used for the production of lubricating oils and corrosion inhibitors. [11] The aforementioned application possibilities of DFA highly depend on the thermal properties, which correlate with the structure of the used mixture.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Dimer Fatty Acid Methyl Esters by Catalytic Oxidation and Reductive Amination: An Efficient Route to Branched Polyamides

Czapiewski

Meier

2017

Euro J Lipid Sci & Tech

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A novel and versatile route toward dimer fatty acid methyl esters (dimer FAMEs) via catalytic oxidation and reductive amination is described. The oxyfunctionalization of mono-unsaturated FAMEs bearing different chain lengths (C11, C18, C22) is accomplished by a co-catalyst-free Wacker Oxidation process in a high pressure reactor. The applied catalytic system of palladium(II) chloride in a dimethylacetamide/water mixture enabled the formation of ketoFAMEs in the presence of molecular oxygen as sole re-oxidant. In a first attempt, partially renewable dimer FAMEs are synthesized by reductive amination of keto-FAME (C18) in the presence of various aliphatic and aromatic diamines and sodium triacetoxyborohydride as selective reducing agent. In another approach, the keto-FAMEs directly underwent reductive amination using Raney-Nickel in order to obtain the corresponding aminoFAMEs. Subsequently, the keto-and amino-FAMEs are used for the synthesis of fully renewable dimer FAMEs via reductive amination with sodium triacetoxyborohydride as reducing agent. In order to demonstrate a possible application for these new dimer FAMEs, three out of the thirteen synthesized dimer FAMEs are selected and studied in a polycondensation with renewable 1,10-diaminodecane using TBD as catalyst. The polyamides are obtained in molecular weights (M n ) of up to 33 kDa and are carefully characterized by 1 H-NMR spectroscopy, FTIR, SEC, and DSC analysis. Practical Applications: The described catalytic route to defined dimer fatty acids has potential applications in lubricants, detergents, polymeric materials, and others. Compared to commercially available dimer fatty acids, a molecularly highly defined mixture of regioisomers is obtained, without contamination of monofunctional or trifunctional fatty acid derivatives, which is advantegous for most of the mentioned applications. Especially for polycondensations, the known stoichiometry of exactly two is a considerable benefit.

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“…In recent years, the utilization of renewable materials, such as plant oils and natural fatty acids, for replacing petroleum‐derived raw materials for the production of polymeric materials has attracted great attention because of social, environmental, and economic considerations. Considerable work has been reported on biobased PUs; this work has focused on the preparation of such types of polyols derived from vegetable oils in combination with petrochemical‐based diisocyanates. It has been shown that biobased PUs have comparable properties in many aspects with PUs derived from petrochemical‐based polyols …”

Section: Introductionmentioning

confidence: 99%

Synthesis and physicochemical study of polyester polyols of epoxy resin of 2,4,6‐tris(4‐hydroxyphenyl)‐1,3,5‐triazine and their polyurethanes

Ghumara

Patel

Adroja

et al. 2013

J of Applied Polymer Sci

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Polyester polyols of ricinoleic acid (ETPRA), oleic acid, linoleic acid (ETPLA), and rosin (ETPR) and epoxy resin of 2,4,6-tris(4-hydroxyphenyl)-1-3-5-triazine (ETP) and their polyurethanes (PUs) were synthesized and characterized by Fourier transform infrared spectroscopy, NMR, differential scanning calorimetry, and thermogravimetric analysis techniques. The PU films showed the following density order: ETPRPU600 > ETPRAPU600 > ETPLAPU600. ETPLAPU600 showed good tensile strength and volume resistivity values compared to ETPRAPU600 and ETPRPU600. All three PUs showed good electric strength. ETPLAPU600 showed almost double the electric strength of ETPRAPU600 and ETPRPU600. The incorporation of soft-segment poly(ethylene glycol) 600 into PU chains resulted in the flexibility of the films. The PU films showed a high water absorption tendency in water, acidic, and saline environments, and they degraded in an alkaline environment. The weight gain tendency of the films was due to surface solvolysis and was also probably due to microcrack formation. The polyester polyols and PUs were thermally stable up to about 167-221 and 184-214 C, respectively, and followed multistep degradation reactions with either fractional or integral order (0.43-2.71) degradation kinetics. Thus, the structure of the PUs affected the studied physicochemical properties of the films.

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Oleochemical products as building blocks for polymers

Cited by 35 publications

References 3 publications

A new method to determine oxidative stability of vegetable fats and oils at simulated frying temperature

A new method to determine oxidative stability of vegetable fats and oils at simulated frying temperature

Synthesis of Dimer Fatty Acid Methyl Esters by Catalytic Oxidation and Reductive Amination: An Efficient Route to Branched Polyamides

Synthesis and physicochemical study of polyester polyols of epoxy resin of 2,4,6‐tris(4‐hydroxyphenyl)‐1,3,5‐triazine and their polyurethanes

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