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Publication Title | Chem. Rev. 2007, 107, 2411−2502 2411 Chemical Routes for the Transformation of Biomass into Chemicals

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Chem. Rev. 2007, 107, 2411−2502 2411 Chemical Routes for the Transformation of Biomass into Chemicals

Avelino Corma,* Sara Iborra, and Alexandra Velty

Instituto de Tecnolog ́ıa Qu ́ımica, UPV-CSIC, Universidad Polite ́cnica de Valencia, Avenida de los Naranjos, s/n, Valencia, Spain

Contents

1. Introduction

2. Chemicals from Biomass: Intermediate Platforms

2.1. Chemicals from Fermentation Processes: Glucose Fermentation

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Received January 31, 2007

4.2.4. Dehydroisomerization of Limonene and 2481 Terpenes To Produce Cymene

4.3. Carene 2482 4.3.1. Isomerization of Carene 2482 4.3.2. Epoxidation of Carene 2482 4.3.3. Isomerization of 2- and 3-Carene Oxides 2483 4.3.4. Dehydroisomerization 2483

4.4. Camphene 2484 4.4.1. Epoxidation of Camphene 2484 4.5. Citral 2484 4.5.1. Aldol Condensations of Citral and 2484

Ketones

4.5.2. Baeyer−Villiger Oxidation: Melonal 2485 4.5.3. Hydrogenation of Citral 2485

5. Conclusions 2488 6. References 2488

1. Introduction

Vegetable biomass is generated from CO2 and H2O using sunlight as the energy source, producing O2 as a subproduct. The primary products formed are C6- and C5-sugars that form cellulose (by polymerization of glucose) and hemicellulose (a polymer of glucose and xylose). There is a third component, lignin, that is a highly cross-linked polymer built of substituted phenols and, together with cellulose and hemicellulose, gives strength to plants. Besides those com- ponents, plants are also able to elaborate energy storage products such as lipids, sugars, and starches as well as other products relatively rich in hydrogen and carbon (terpenes) that are found in essential oils that are components of resins, steroids, and rubber.

The Kyoto protocol, together with the desire to reduce society’s dependence on imported crude oil, has directed researchers’ attention to the use of biomass as a source of energy and, more specifically, for transportation fuels.1-4 In this sense, ethanol has been used for some time already, blended with conventional fuels or transformed into ethyl tert-butyl ether. However, if one considers the energy content of the different biomass products, terpenes top the list, followed by vegetable oils, lignin, and sugars. Since the production of terpenes is too low to meet the requirements for biofuels, it is not surprising that the most attention has been focused on vegetable oils. However, the limited amounts of triglycerides available, together with ethical reasons, has directed future development for large-scale production of biofuels toward lignocellulose as the most interesting source. If lignocellulose can be used for biofuels, then the more valuable sugars, vegetable oils, and terpenes

2.1.1. Lactic Acid Platform 2413 2.1.2. Succinic Acid Platform 2417 2.1.3. 3-Hydroxypropionic Acid Platform 2421 2.1.4. Itaconic Acid Platform 2422 2.1.5. Glutamic Acid Platform 2423

2.2. Chemical Transformations of Monosaccharides

2424

2.2.1. Dehydration of Monosaccharides 2424 2.3. Chemical Transformation of Disaccharides: 2443

Sucrose

2.3.1. Hydrolysis 2443

2.3.2. Esterification 2444

2.3.3. Etherification 2445

2.3.4. Oxidation 2446

2.3.5. Glucosyl Shift: Production of Isomaltulose and Isomalt

2.3.6. Polymers

3. Vegetable Oils and Animal Fats 2449

3.1. Reaction of the Carboxy Group 2449 3.1.1. Fatty Acids 2449 3.1.2. Fatty Amines 2450 3.1.3. Fatty Alcohols 2452 3.1.4. Glycerol 2453

3.2. Reaction of the Fatty Chain 2463

3.2.1. Epoxidation 2464

3.2.2. Ring-Opening of Epoxidized Fatty Acid 2466

Derivatives

3.2.3. Hydroformylation 2467

3.2.4. Dimerization 2468

3.2.5. Oxidative Cleavage and Ozonolysis

3.2.6. Metathesis 2470

4. Terpenes 4.1. Pinene

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2472 4.1.1. Isomerization: R-Pinene 2472 4.1.2. Epoxidation of R-Pinene 2475 4.1.3. Isomerization of R-Pinene Oxide 2477 4.1.4. Hydration of R-Pinene: R-Terpineol 2478 4.1.5. Dehydroisomerization 2479 4.2. Limonene 2480 4.2.1. Isomerization 2480 4.2.2. Epoxidation: Limonene Oxide 2480 4.2.3. Isomerization of Limonene Oxide 2481

10.1021/cr050989d CCC: $65.00

Published on Web 05/30/2007

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© 2007 American Chemical Society

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