Preparation of Methyl Acetoxypropionate:Reaction of Lactic Acid with Methyl Acetate

Rehberg, C. E.; Faucette, W. A.; Fisher, C. H.

doi:10.1021/ie50413a025

Cited by 13 publications

(7 citation statements)

References 7 publications

(7 reference statements)

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“…The rst encounter of LA usage to produce AA is found in a 1935 paper 78 by Burns et al and this was followed in the 1940s with papers by Fisher and co-workers [79][80][81][82][83] and a patent led in 1949 by Atwood. 84 Generally, an alkyl lactate is converted into its corresponding alkyl acrylate via pyrolysis of an alkyl 2-acetoxypropionate intermediate with the formation of acetic acid as a by-product.…”

Section: Dehydration To Acrylic Acidmentioning

confidence: 99%

“…82 The acetoxy intermediate is made by contacting an alkyl lactate with acetic anhydride, 79,84 or alternatively from lactic acid with acetic acid and an entraining agent followed by esterication or with methyl acetate directly. 80 Werpy et al continued on this path, but proposed an azeotropic distillation setup with an acid catalyst to prepare the precursor from LA and acetic acid before subjecting the precursor to pyrolysis. In this last step, a weak acidic catalyst can be added.…”

Section: Dehydration To Acrylic Acidmentioning

confidence: 99%

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Lactic acid as a platform chemical in the biobased economy: the role of chemocatalysis

Dusselier

Wouwe

Dewaele

et al. 2013

Energy Environ. Sci.

708

620

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Upcoming bio-refineries will be at the heart of the manufacture of future transportation fuels, chemicals and materials. A narrow number of platform molecules are envisioned to bridge nature's abundant polysaccharide feedstock to the production of added-value chemicals and intermediate building blocks. Such platform molecules are well-chosen to lie at the base of a large product assortment, while their formation should be straightforward from the refined biomass, practical and energy efficient, without unnecessary loss of carbon atoms. Lactic acid has been identified as one such high potential platform. Despite its established fermentation route, sustainability issueslike gypsum waste and cost factors due to multi-step purification and separation requirementswill arise as soon as the necessary orders of magnitude larger volumes are needed. Innovative production routes to lactic acid and its esters are therefore under development, converting sugars and glycerol in the presence of chemocatalysts. Moreover, catalysis is one of the fundamental routes to convert lactic acid into a range of useful chemicals in a platform approach. This contribution attempts a critical overview of all advances in the field of homogeneous and heterogeneous catalysis and recognises a great potential of some of these chemocatalytic approaches to produce and transform lactic acid as well as some other promising a-hydroxy acids. Broader contextLactic acid is one of the top biomass derived platform chemicals, with a promising role in future bio-reneries. A wide range of catalytic transformations of lactic acid are feasible leading to the selective production of green solvents, ne chemicals, commodity chemicals and fuel precursors. Even more appealing is its role as the precursor for biodegradable PLA (polylactic acid) polymers. These polyesters have the potential to replace fossil derived plastics in particular applications, and based on life cycle analyses, they have a more positive impact on the environment. PLA can also be used in vivo and in biomedical applications. The demand for PLA and green solvents is growing and stresses the current fermentative production of lactic acid, which suffers from up-scaling and environmental issues due to concerning waste co-generation and purication steps. Novel chemocatalytic routes are under development to obtain pure lactic acid or esters directly from sugar feedstock. These mainly heterogeneous catalytic processes have potential and could lie at the heart of an evolution in lactic acid research. Once lactic acid is available at competitive prices, its use as a feedstock in a platform approach could become commercially viable, thereby providing renewable and CO 2neutral alternatives for fossil derived chemicals.

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Section: Dehydration To Acrylic Acidmentioning

confidence: 99%

Section: Dehydration To Acrylic Acidmentioning

confidence: 99%

Lactic acid as a platform chemical in the biobased economy: the role of chemocatalysis

Dusselier

Wouwe

Dewaele

et al. 2013

Energy Environ. Sci.

708

620

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show abstract

“…Toxic concentrations of metals resulting from the corrosion of the equipment have been encountered frequently in experimental work (25,54).…”

Section: Crude Lactic Acid As Starting Materialsmentioning

confidence: 99%

“…tion of methyl lactate in high yield by conventional methods is unusually difficult because methyl lactate distills azeotropically with water but methanol does not, and methyl lactate is readily hydrolyzed (25). Although esterification of lactic acid with methanol is troublesome, this operation is important because methyl lactate can be converted readily into higher lactic esters by alcoholysis (5) or into methyl acrylate by pyrolysis of its acetyl derivative (5,29).…”

mentioning

confidence: 99%

Preparation of Methyl Lactate.

Filachione¹,

Lengel²,

Fisher³

1945

Ind. Eng. Chem.

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“…Previous communications (5,20) from this laboratory have shown that methanol reacts readily with condensation polymers of lactic acid, methyl lactate is readily volatilized in a stream of methanol vapor, and methyl lactate and w-ater distill azeotropically. These facts seemed to warrant an investigation of the preparation and removal of methyl lactate from aqueous solutions of lactic acid by passing methanol vapor through the solution.…”

mentioning

confidence: 99%