Functionalization via glycerol transesterification of polymerized soybean oil

Lubguban, Arnold A.; Tu, Yuan-Chan; Lozada, Zuleica R.; Hsieh, Fushing; Suppes, Galen J.

doi:10.1002/app.29382

Cited by 21 publications

(12 citation statements)

References 9 publications

(19 reference statements)

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“…Highly porous lightweight combustible foams tend to have a fast flame spread and a high heat emission. The increasing demand for PU foams is the reason why many studies are devoted to fire retardancy [30,31].…”

Section: Flammability Of Rigid Pu Foamsmentioning

confidence: 99%

Flammability of Bio-Based Rigid Polyurethane Foam as Sustainable Thermal Insulation Material

Kirpļuks¹,

Cābulis²,

Avots³

2016

Insulation Materials in Context of Sustainability

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One of the biggest disadvantages of rigid polyurethane foams is its low thermal resistance, high flammability, and high smoke production when burning. Greatest advantage of this thermal insulation material is its low thermal conductivity, which at 20-25 mW/(m·K) is superior to other commercially available insulation materials. In recent years polyurethane materials from renewable resources have been widely studied. But their use on industrial scale was limited due to inconstant performance and relatively high price of raw materials. Different bio-based raw materials, such as rapeseed oil and tall oil, could provide abundant feedstock for PU foam production. Decrease of flammability of PU materials conventionally is achieved by addition of flame retardants, halogen-containing compounds, and phosphates. It can be considered that halogenated fire retardants could have several health hazards, such as volatile compound emission from materials and toxic gas release during burning process. Expandable graphite could be an answer to this flammability problem. This chapter describes development of bio-based rigid polyurethane foams and their flammability reduction using sustainable flame retardants. Different expandable graphite intumescent flame retardants provided significant flammability reduction while maintaining low thermal conductivity of insulation materials.

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Section: Flammability Of Rigid Pu Foamsmentioning

confidence: 99%

Flammability of Bio-Based Rigid Polyurethane Foam as Sustainable Thermal Insulation Material

Kirpļuks¹,

Cābulis²,

Avots³

2016

Insulation Materials in Context of Sustainability

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“…Over the past few years, the converting of the double bonds of triglycerides to hydroxyls groups and their application in polyurethane chemistry was continued and extended. There are possible solutions such as: hydroformylation and hydrogenation, epoxidation followed by oxirane ring‐opening, microbial conversion, thermal polymerization followed by transesterification, ozonolysis and hydrogenation or halogen addition and nucleophilic substitution 4–10. Vegetable‐oil‐based polyol structure depends not only on the method of the insertion of hydroxyl groups but also on the type of triglycerides.…”

Section: Introductionmentioning

confidence: 99%

Effect of different rapeseed‐oil‐based polyols on mechanical properties of flexible polyurethane foams

Rojek

Prociak

2012

J of Applied Polymer Sci

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Two rapeseed-oil-based polyols were synthesized by partial epoxidation of the double bonds in fatty acid chains and overall opening oxirane rings by using diethylene glycol. Flexible polyurethane foams with varied isocyanate index and modified by partial substitution of petrochemical polyether triol with rapeseed-oilderived polyols were obtained. Bio-polyols: Polyol I and Polyol II differed in functionalities (2.5 and 5.2, respectively) and hydroxyl values (114 and 196 mg KOH/g, respectively). Influence of the bio-polyols on mechanical properties, resilience, apparent density, and cellular structure of synthesized foams was investigated. Compression properties were examined and compared via determining compression values and compression stress-strain characteristics, as well as tensile strength and elongation at break were estimated. Foams modified with Polyol I had higher values of resilience and elongation at break than those with Polyol II, while higher tensile and compression strength and superior cell structure were observed in the case of foams modified with Polyol II.

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“…Thiol‐Ene addition of mercaptoalcohols also presents a possibility to introduce hydroxyl groups (Figure d) . Other approaches for the synthesis of polyols target the ester functionality of triglycerides and involve the transesterification with multifunctional alcohols, such as glycerolysis, or amidation with amines bearing several hydroxy groups (Figure g and h) . All reported methods used to synthesize polyols from unsaturated substrates are summarized in Figure .…”

Section: Introductionmentioning

confidence: 99%

A Sustainable Tandem Catalysis Approach to Plant Oil‐Based Polyols via Schenck‐Ene Reaction and Epoxidation

Unverferth

Meier

2018

Euro J Lipid Sci & Tech

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Novel polyols are synthesized in a one‐pot, tandem reaction approach. First, singlet oxygen is used as oxidant in the photochemical Schenck‐Ene reaction to obtain allyl hydroperoxides of triglycerides, which are reacted in situ to the corresponding epoxy alcohols catalyzed by titanium(IV) isopropoxide. Subsequent acidic epoxide ring‐opening with perchloric acid yields a triglyceride‐based polyol. Under basic conditions applying aqueous sodium hydroxide solution, cleavage of the ester bonds of the triglyceride and epoxide ring‐opening occur simultaneously resulting in a fatty acid‐based polyol. Practical Applications: Polyols, especially also based on renewable fatty acids, are valuable monomers for the synthesis of polyurethanes, polyester‐ and alkyd‐resins. With the here reported method, a maximum of three hydroxyl groups per double bond of the unsaturated triglyceride can be introduced, which cannot be realized with the methods reported to date. A tandem catalytic system of Schenk‐Ene reaction and in situ epoxidation efficiently leads to plant oil derived epoxy alcohols, which can be converted to triglyceride or fatty acid based polyols. Most interestingly, three OH‐groups per double bond of the fatty acid can be obtained via this route.

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Functionalization via glycerol transesterification of polymerized soybean oil

Cited by 21 publications

References 9 publications

Flammability of Bio-Based Rigid Polyurethane Foam as Sustainable Thermal Insulation Material

Flammability of Bio-Based Rigid Polyurethane Foam as Sustainable Thermal Insulation Material

Effect of different rapeseed‐oil‐based polyols on mechanical properties of flexible polyurethane foams

A Sustainable Tandem Catalysis Approach to Plant Oil‐Based Polyols via Schenck‐Ene Reaction and Epoxidation

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