Industrial Uses for Cane Sugar II. Properties of Alkyl Esters of Levulinic Acid

Cox, Gerald J.; Dodds, Mary L.

doi:10.1021/ie50285a005

Cited by 12 publications

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“… k 2,5-Dimethylfuran heating value, solubility in water, and RON from Roman-Leshkov et al; boiling point from Lewis; specific gravity from CRC Handbook; latent heat of vaporization from uncited data in Zhong et al; viscosity (ASTM D445) and vapor pressure (ASTM D5191), this work. l MTHF heating value (ASTM D240) and RON and MON (ASTM D2699 and ASTM D2700), this work; boiling point from CRC Handbook; all other properties from Penn Specialty Chemicals, Inc m Methyl levulinate boiling point and heat of vaporization (at boiling point) from ChemSpider; solubilities and specific gravity from Cox and Dodds n Ethyl levulinate boiling point from Cox and Dodds; lower heating value (ASTM D240) and latent heat of vaporization (at boiling point) from ChemSpider; solubilities, vapor pressure (ASTM D5191), and viscosity (ASTM D445), this work; density from Sigma–Aldrich …”

Section: Introductionmentioning

confidence: 99%

“… m Methyl levulinate boiling point and heat of vaporization (at boiling point) from ChemSpider; solubilities and specific gravity from Cox and Dodds n Ethyl levulinate boiling point from Cox and Dodds; lower heating value (ASTM D240) and latent heat of vaporization (at boiling point) from ChemSpider; solubilities, vapor pressure (ASTM D5191), and viscosity (ASTM D445), this work; density from Sigma–Aldrich o Butyl levulinate boiling point from CRC Handbook; lower heating value (ASTM D240) and latent heat of vaporization (at boiling point) from ChemSpider; vapor pressure (ASTM D5191) and viscosity (ASTM D445), this work; density from Sigma–Aldrich …”

Section: Introductionmentioning

confidence: 99%

“… m Methyl levulinate boiling point and heat of vaporization (at boiling point) from ChemSpider; solubilities and specific gravity from Cox and Dodds …”

Section: Introductionmentioning

confidence: 99%

“… n Ethyl levulinate boiling point from Cox and Dodds; lower heating value (ASTM D240) and latent heat of vaporization (at boiling point) from ChemSpider; solubilities, vapor pressure (ASTM D5191), and viscosity (ASTM D445), this work; density from Sigma–Aldrich …”

Section: Introductionmentioning

confidence: 99%

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Renewable Oxygenate Blending Effects on Gasoline Properties

et al. 2011

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The oxygenates ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol (isobutanol), 1-pentanol, 3-methyl-1-butanol (isopentanol), methyl levulinate, ethyl levulinate, butyl levulinate, 2-methyltetrahydrofuran (MTHF), 2-methylfuran (MF), and 2,5-dimethylfuran (DMF) were blended in three gasoline blendstocks for oxygenate blending (BOBs) at levels up to 3.7 wt % oxygen. Chemical and physical properties of the blends were compared to the requirements of ASTM specification D4814 for spark-ignited engine fuels to determine their utility as gasoline extenders. Vapor pressure, vapor lock protection, distillation, density, octane rating, viscosity, and potential for extraction into water were measured. Blending of ethanol at 3.7% oxygen increased vapor pressure by 5–7 kPa as expected. 2-Propanol slightly increased vapor pressure in the lowest-volatility BOB, while all other oxygenates caused a reduction in vapor pressure of up to 10 kPa. Coefficients for the Wilson equation were fitted to the measured vapor pressure data and were shown to adequately predict the vapor pressure of oxygenate–gasoline blends for five individual alcohols and MTHF in different gasolines. Higher alcohols and other oxygenates generally improved vapor lock protection. Butyl levulinate blended at 2.7% oxygen caused the distillation end point to exceed 225 °C, thus failing the specification. Distillation parameters were within specification limits for the other oxygenates tested. Other than ethanol, MF, and DMF, the oxygenates examined will not produce blends with satisfactory octane ratings at these blend levels when blended into lower-octane blendstocks designed for ethanol blending. However, all oxygenates tested except 1-pentanol and MTHF produced an increase in octane rating. For ethanol, the propanol isomers, and methyl levulinate, 20 wt % or more of the oxygenate could be extracted into water in a room-temperature water tolerance experiment. For the butanol isomers and ethyl levulinate, the percent extracted ranged from about 4% to 8%. Extraction for other oxygenates was 2% or lower. Methyl levulinate separates from gasoline as a separate liquid phase at temperatures below 0 °C.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“… m Methyl levulinate boiling point and heat of vaporization (at boiling point) from ChemSpider; solubilities and specific gravity from Cox and Dodds …”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Renewable Oxygenate Blending Effects on Gasoline Properties

et al. 2011

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“…Because water-soluble fuels are more difficult to handle, interest in levulinate esters as fuels has focused on esters of ethanol and higher molecular-weight alcohols. With boiling points of over 200 °C, close to that of the heaviest components of gasoline, and a flash point of 91 °C for the ethyl ester, there has also been interest in the examination of these oxygenates as diesel-blending components. Grove and co-workers have reported data on the properties of ethyl, n -butyl, and other ester blends with diesel fuel .…”

Section: Introductionmentioning

confidence: 99%

Properties and Performance of Levulinate Esters as Diesel Blend Components

et al. 2011

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The properties of ethyl (EL) and n-butyl levulinate (BL), two potential cellulose-derived diesel blend components, were assessed as both neat oxygenates and blends with diesel fuel. The samples tested were produced commercially from cellulose and alcohols but were not reagent-grade samples. They were relatively free of impurities, although EL contained some acidic compounds and both contained parts-per-million levels of calcium. Both esters exhibited a very low cetane number. The melting points of both esters were less than −60 °C. The water solubility of EL was 15.2 wt %, while that of BL was only 1.3 wt %. Blends of diesel fuel with EL were found to have an elevated cloud point, despite the extremely low melting point of this compound, because EL separates from diesel fuel as a separate liquid phase at low temperatures. This can be mitigated to some extent by including biodiesel in the blend. BL remained in solution and raised the diesel cloud point only when blended into −45 °C cloud point/15% aromatic no. 1 diesel fuel. Both esters were found to significantly increase diesel lubricity and conductivity. The esters were treated with the cetane-enhancing compound 2-ethyl hexyl nitrate and were tested as blends with diesel fuel in a 2008 model year Cummins ISB engine with the measurement of regulated pollutant emissions over the federal heavy duty diesel transient cycle. Fuel chemistry had no effect on tailpipe total hydrocarbons, carbon monoxide, or particulate matter for this diesel oxidation catalyst and particle filter equipped engine. The engine-out smoke number was reduced by 41.3% with a 10% blend of EL (EL10) and reduced by 55% with a blend of 20% BL (BL20). EL10 had no effect on emissions of nitrogen oxides (NO x ), while BL20 increased NO x by 4.6%. Because of the poor solubility of EL in diesel fuel at low temperatures, its use as a diesel blend component will be technically challenging. The low cetane number of both esters can be addressed with cetane improver additives.

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Fortschritte der physiologischen Chemie seit 1929. I. Naturstoffe: 1. Kohlenhydrate

Ohle¹

1934

Angewandte Chemie

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47. Jahrgang, S.241-262 m Inhaltsverzeimnls: Siehe AnzeigenteU S. 8 0 2 m 28. April i934, Nr. 17 Fortschritte der physiologischen Chemie seit 1929.Vorbemerkung der Schriftleitung. In diesem Fortschrittsbericht, der mit dem folgenden Aufsatz eine umfangreiche Reiihe eroffnet, soll, zum erstenmd in dieser Vollstandigkeit, ein Oberblick uber das grofje Gebiet der physiologischen Chemie gegeben werden. Wesentlich war uns eine kritische Auswahl der wichtigsten Probleme und Apbeiten; weder eine erschopfende Wiedergabe aller Einzelheiten, noch die Auffuhrung der gesamten Literatur war beabsichtigt. Auch mufite bei Betmung des Chemischen das rein Physiologische zuriicktreten.

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Industrial Uses for Cane Sugar II. Properties of Alkyl Esters of Levulinic Acid

Cited by 12 publications

References 0 publications

Renewable Oxygenate Blending Effects on Gasoline Properties

Renewable Oxygenate Blending Effects on Gasoline Properties

Properties and Performance of Levulinate Esters as Diesel Blend Components

Fortschritte der physiologischen Chemie seit 1929. I. Naturstoffe: 1. Kohlenhydrate

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