Diesters of Lactic Acid. Adipates of Various Lactates<sup>1,2</sup>

Rehberg, C. E.; Dixon, Marion B.

doi:10.1021/ja01168a513

Cited by 17 publications

(6 citation statements)

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“…The oligomer esters (L 2 E, L 3 E, etc. in Figure 5.1) have been reported to have use as plasticizers, [72][73][74][75] but no commercial market yet exists. Thus, the challenge in achieving high L 1 E yields from lactic acid is to either 1) further convert the oligomeric byproducts to the monomer L 1 E, or 2) avoid the formation of oligomers altogether by working with dilute lactic acid solutions.…”

Section: Introductionmentioning

confidence: 99%

Reactive Distillation for Esterification of Bio-based Organic Acids

Fields¹,

Miller²,

Asthana³

et al. 2008

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SECTION TEN-SPEAD MODELING FOR ORGANIC ACID AND ESTERS VAPOR PRESSURE 10.1 Background 10.2 Approaches in SPEAD Modeling 10.2.1. Pair Interaction Sites of Ethyl Lactate Oligomers and Acetals of Glycerols 10.2.2. Approach of Optimizing Secondary-OH and-COO-groups 10.2.3. Mathematical Methodology 10.2.4. The DBCONF routine algorithm 151 10.3. Results of Optimization of the 2 nd-OH and-COO-groups 10.4. Prediction of Psat for Ethyl lactate Oligomers 154 10.4.1. Effect of intramolecular H-bonds in Lactates 10.4.2. A common point for Ethyl Lactate Oligomers 156 10.5. Prediction of P sat for Acetals SECTION ELEVEN-REFERENCES 162 157 Original SOW covered by final report 161 SECTION ONE INTRODUCTION AND LITERATURE BACKGROUND ON ESTERIFICATION AND REACTIVE DISTILLATION 1.1. Introduction Organic esters are gaining increased importance in a number of industrial applications, primarily as solvents to replace petroleum-derived materials, and thus hold promise as a major class of bio-based commodity products. The application of reactive distillation to esterification holds great promise for efficient production, yet is relatively unexplored as a commercial process. The aim of the proposed project was to implement a full complement of scientific and technical tools ranging from fundamental thermodynamic data collection to detailed process economic and market analyses in order to demonstrate the viability of reactive distillation for esters production. The project was conducted by a multi-faceted team with combined expertise in scientific area necessary for the successful outcome of this project. Reactive distillation has gained substantial attention recently in the research and industrial communities, 1-2 because it offers clear advantages over traditional approaches for carrying out equilibrium-limited chemical reactions. Candidate reactions for reactive distillation are characterized by a substantial difference in volatility between reaction products, such that removal of one product by distillation drives the reaction to completion. Reactions are often catalyzed, either by solid catalysts packed within the distillation column or by addition of homogeneous catalysts (acids, bases, metal complexes, etc.) added to the column feed. Esterification of organic acids satisfies the above criterion for consideration as a reaction amenable to reactive distillation. In particular, the formation of alkyl esters, typically formed by reaction of simple alcohols such as methanol, ethanol, etc. with the acid, is attractive, as the ester and water produced as reaction products can usually be separated by distillation. Although this principle is well understood, reactive distillation has not been broadly exploited for esterification because of the typical complexity of the thermodynamics of these systems. An application of reactive distillation which has been demonstrated commercially is Tennessee Eastman's methyl acetate process 3. Upon its implementation; the single reactive distillation column replaced thirteen individual unit operations and ...

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Section: Introductionmentioning

confidence: 99%

Reactive Distillation for Esterification of Bio-based Organic Acids

Fields¹,

Miller²,

Asthana³

et al. 2008

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“…The boiling points shown in Table I were read from the Cox charts previously published (5,6). Most of the esters had boiling points higher than that of di-2-ethylhexyl phthalate.…”

Section: Preparation and Properties Of Estersmentioning

confidence: 99%

“…In the preparation of small amounts of these compounds (listed in Table I) for screening purposes the dibasic acid chlorides were used in most cases as a matter of convenience (5,6). This method was obviously impractical for commercial production of the compounds, and so a study was made of the reaction of dicarboxylic acids with alkyl lactates.…”

Section: Direct Esterification Of Alkyl Lactates With Dicarboxylic Acidsmentioning

confidence: 99%

“…The symmetrical esters, bis(butyl lactate) and bis(butyl lactyllactate) adipate were also prepared in pure form by use of adipyl chloride. The properties shown for these in Table II were determined on these pure samples (5). The unsymmetrical esters were isolated from the mixtures of esters obtained by use of adipic acid and hence were somewhat less pure.…”

Section: Direct Esterification Of Alkyl Lactates With Dicarboxylic Acidsmentioning

confidence: 99%

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Plasticizers from Lactic Esters and Dibasic Acids

Rehberg¹,

Dietz²,

Meiss³

et al. 1952

Ind. Eng. Chem.

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“…Replacing ethyl lactate at Pi-with the corresponding benzyl ester 24 results in an active compound. Some measure of bulk tolerance exists at Pr as shown by the fact that 3-phenyllactic acid (25), the oxygen isostere of phenylalanine, is tolerated at this site. Elongation of the molecule to extend binding into the P3< site gives active compounds 26-28.…”

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Proteinase inhibitors. 1. Inhibitors of elastase

Dorn¹,

Zimmerman²,

Yang³

et al. 1977

J. Med. Chem.

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A series of peptides and depsipeptides containing 2-methylcarbazic acid (H-Mec-OH), the 2-aza analogue of alanine, was prepared and tested as inhibitors of pancreatic and human granulocyte elastases. A requirement for a minimum chain length as well as specific amino acid sequence was observed which correlates well with both substrate and inhibitor studies by others in this field. The most active inhibitors have the structure Ac-Ala-Ala-Pro-Mec-Lac-R. When Lac-R is an ester, only the pancreatic enzyme is inhibited. When Lac-R is an amide or hydrazide, then both enzymes are inhibited. The inhibitory activity is reversible; the inhibitors are not hydrolyzed by the enzyme and the inhibition is noncompetitive with synthetic substrates of similar structure, suggesting that binding at the sites adjacent to the carboyl group of the amino acid analogue, 2-methylcarbazic acid, is important for this inhibition. The data further demonstrate the differences between pancreatic and granulocyte elastases.

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Diesters of Lactic Acid. Adipates of Various Lactates^1,2

Cited by 17 publications

References 0 publications

Reactive Distillation for Esterification of Bio-based Organic Acids

Reactive Distillation for Esterification of Bio-based Organic Acids

Plasticizers from Lactic Esters and Dibasic Acids

Proteinase inhibitors. 1. Inhibitors of elastase

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Diesters of Lactic Acid. Adipates of Various Lactates1,2

Cited by 17 publications

References 0 publications

Reactive Distillation for Esterification of Bio-based Organic Acids

Reactive Distillation for Esterification of Bio-based Organic Acids

Plasticizers from Lactic Esters and Dibasic Acids

Proteinase inhibitors. 1. Inhibitors of elastase

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Product

Resources

About

Diesters of Lactic Acid. Adipates of Various Lactates^1,2