Chemistry of Bioproducts

Abstract

Bioproducts are bio-based products derived from sustainable resources or biomass. Energy, chemicals, and various materials obtained from such resources can be classified under the umbrella of bioproducts that provide an alternate to fossil fuel-derived products. Bioproducts offer the advantage of reducing greenhouse gas emission, arresting global warming, and preventing loss of fossil fuel resources. This document has attempted to review the three major classes of bioproducts, viz. bioenergy, biochemicals, and biomaterials from the viewpoint of a chemist. The emphasis has been primarily given to the understanding of chemical structures, formations, transformations, and reactions of various classified bioproducts. Chemistry is inevitable and omnipresent in the process of making bioproducts beginning with biomass through intermediates. The proper understanding, safe manipulation, and smart application of the chemistry involved in the generation of bioproducts are essential in the smooth transition from fossil fuel products to bioproducts with the ultimate goal of making the world a safer and cleaner place.

Questions

• 1. How are bioproducts different from other products derived from petroleum resources?

• 2. Define biomass.

• 3. What is the traditional equivalent of biomass?

• 4. What are the three major classifications of bioproducts?

• 5. Do you think the modern society and governments should heavily invest in developing bioproducts? Justify your answer laying out the pros and cons supporting your arguments.

• 6. Are bioproducts always derived directly from biomass? Please explain.

• 7. Give a few examples of bioproducts that are directly obtained from nature.

• 8. Give a few examples of bioproducts that involve one or more steps between biomass and the final product.

• 9. Are all soaps bioproducts? Justify your answer.

• 10. Is it possible to produce soap from any plant or algae that produces triglyceride? Please justify your answer.

• 11. What is biodiesel? Please explain its structure and the precursor it is made from.

• 12. What are the two major components of a triglyceride?

• 13. Are all fatty acids identical?

• 14. What is the fundamental difference between saturated fat and unsaturated fat?

• 15. Should the nature of the starting fat (triglyceride) affect the nature of the biodiesel as a product?

• 16. What is the three-dimensional shape of soap in water?

Glossary

Acetylation

Chemical or biochemical reaction by which an acetyl functionality is attached to a compound.

Alcoholysis

A chemical reaction by which alcohol replaces the alcoholic part of an existing ester functionality to generate a new ester.

Aliphatic alcohols

Alcohols comprising only aliphatic branches devoid of any aromatic groups.

Alkylbenzenes

Alkyl substituted benzene-based aromatic compounds.

Amphiphilic

The property by which compounds can possess solubility properties in both aqueous and non-polar solvents.

Amylopectin

Amylopectin is a plant polysaccharide which in conjunction with amylose, constitute starch.

Amylose

A polysaccharide containing α-d-glucose monomer.

Antioxidant

Molecules that can prevent oxidation, often by being oxidized with their intrinsic reducing properties.

Arnica

Herbaceous plant in the sunflower family.

Aromatic

General: substances with ‘aroma.’ In organic chemistry terms, aromatic compounds are special cyclic molecules with alternating double bonds. These planar molecules have extra stability by virtue of their structure and electronic status.

Bioalcohols

Alcohols derived from biological/renewable resources.

Bioavailability

A pharmacokinetic property of drugs that defines the fraction of the drug reaching systemic circulation.

Bio-based

‘Bio-base’ is the type products specifically derived from biological/renewable resources.

Biocatalysts

Chemical catalysts derived from the biological resources.

Biochemical pathways

The mechanistic chemical pathways and directions for multi-step synthetic processes occurring in living organisms.

Biochemicals

Chemicals of commercial value generated from biological/renewable resources.

Biocomposites

A composite material made from natural fibers and does not contain petroleum-derived ingredients.

Biodegradability

The biologically manifested breakdown of a material into smaller fragments.

Biodegradable

The property of a substance or material that enables it to undergo biological degradation process.

Biodegradable polymer

A polymer material that can breakdown into smaller subunits by natural processes biochemically motivated.

Biodiesel

Diesel generated exclusively from biological/renewable resources.

Bioeconomic activity

The complex economic network existing in the identification, isolation, and utilization of renewable resources to generate, distribute, and use of various bioproducts.

Bioeconomy

Bioeconomy is the economy involved in the world of bioproducts: their production, distribution, usage, and waste management.

Bioefficacy

The efficiency of a medicinal drug candidate to distribute itself into the systemic circulation.

Bioenergy

Energy exclusively produced from biological or renewable resources.

Biofuel

Fuel produced from biological resources or biomass.

Biogas

The mixture of gases derived from renewable biological sources.

Biolubricant

Biomass-derived lubricants.

Biomass

Biomass is the renewable resource for commercial bioproducts. Biomass to bioproduct is equivalent to petroleum products to fossil fuel resources.

Biomaterials

Commercial materials generated from biomass.

Bioplastics

Plastics made from renewable sources.

Bioproducts

Commercial products (chemicals, energy, and materials) derived from renewable raw materials and chemicals.

Biorefinery

It is the whole process of using biomass to generate various bioproducts: biochemical, bioenergy, and biomaterial.

Biosynthesized

Biochemical process of generating chemical products.

Biotechnology

The technology developed by human to utilize biological resources in more than one way(s) to generate commercial products.

Cannabinoids

Molecules that bind with cannabinoid receptors to reduce the production of natural neurotransmitter.

Carbon cycle

It is the cyclic process by which carbon moves or exchanges through various parts of the biosphere.

Catabolize

The natural biochemical pathway by which a molecule undergoes a structural alteration toward its expulsion from the living system.

Catalysts

The process by which a natural or synthetic material can increase the rate of a chemical reaction.

Cellophane

Cellophane, a bioproduct, is a transparent or translucent polymeric sheet made from regenerated cellulose (biomass).

Cellulose

It is the most abundant biopolymer (biologically produced) with various commercial applications.

Combustion

A chemical process by which an organic compound reacts with oxygen to break down into smaller fragments releasing energy. A common example of combustion is fire.

Composites

Composite or composite materials are commercially produced from more than one materials with the final property different from that of the parent materials.

Disaccharide

A carbohydrate consisting of two identical or different monosaccharide units. Sucrose, lactose, and maltose are examples of disaccharides.

Drug metabolism

The biochemical process by which a medicinal molecule (drug) undergoes natural transformations in the living system, generally humans.

Drugs

Natural, synthetic, or hybrid compounds developed for the management, treatment, or cure of an ailment.

Emulsifier

A substance that stabilizes an emulsion.

Essential oils

Essential oils are plant products that find a wide range of direct use ranging from alternative medicines to massage oils.

Eugenol

An aromatic natural compound extracted from essential oils such as clove oil.

Fatty acids

Naturally occurring long hydrocarbon chain carboxylic acids found in lipids, fats, and other complex natural products.

Fermentation

The biochemical pathway for sugars to break down into smaller units such as acids, alcohols, and gases. Fermentation can occur without oxygen.

Fine chemicals

Synthetic chemicals with substantial commercial value often produced through multi-step chemical syntheses. Their usage varies from being building blocks for other essential chemical products, intermediates in a multi-step process toward other target molecules, and active ingredients.

Fischer esterification

The chemical transformation to convert a carboxylic acid and an alcohol into a carboxylic ester.

Fischer-Tropsch process

A chemical process developed by Franz Fischer and Hans Tropsch to convert carbon monoxide and hydrogen gases into hydrocarbons.

Flavonoid

A class of tricyclic aromatic plant biochemicals that contributes to the color of a plant’s flower.

Fluid reactor

A special chemical reactor where a gas or liquid flows through a solid at high speed.

Food additives

Substances added to food in order to enhance its nutritional quality.

Food and Drug Administration (FDA)

A federal agency under United States Department of Health and Human Services is a regulatory agency for various food and medicinal products, therapeutic agents, medical devices, cosmetics, animal foods, and veterinary products.

Food supplements

Edible products that are supposed to provide with the nutrients that could otherwise be missed.

Fossil feedstock

The non-renewable petroleum-based resources.

Fossil fuels

Petroleum-based fuels.

Fumaric acid

A 4 carbon-containing natural diacid that is used in the food and medicinal world.

Global warming

The gradual and steady increase of the average temperature in Earth’s climate.

Gluconic acid

A natural poly-hydroxy carboxylic acid often used as a food additive to maintain pH.

Glucose

The simplest sugar formed by plants during photosynthesis.

Glycerin, Glycerol

A trihydroxy small organic molecule that is the backbone of several natural triglycerides (fat). It has multipurpose uses spanning from the food, chemical, and medicinal industry.

Green chemistry

Green chemistry is the environmentally safe chemical method of producing commercially viable products employing safer and less harmful reactants, reagents, solvents, methodology, and producing less hazardous waste materials.

Green diesel

Diesel produced from biomass in a less hazardous process.

Green practice

The overall practice giving maximum priority to environmentally safe procedures.

Guaiacols

Naturally occurring phenolic compounds that use in food and medical industry.

Hemicellulose

Non-crystalline, amorphous mix of polysaccharides.

Hydrolysis

Water-mediated degradation of organic compounds containing primarily ester and amide bonds.

Insect-repellants

Natural and synthetic compounds that repel insects.

Intellectual property

Intellectual property (IP) is the technical know-how of an invention pertaining to the individual(s) responsible for the particular invention. IP is often legally protected in the form of patents, trademarks, and copyrights on behalf of the inventor(s).

Isoprene

2-Methyl butadiene, a small 4-carbon chain alkene, emitted by the green vegetation. Isoprene is often found to be the building blocks for many natural chemical products.

Isosorbide

A bicyclic alcohol derived from glucose and used as a diuretic.

Itaconic acid

A naturally occurring dicarboxylic acid produced from glucose fermentation.

Lactic acid

Nature-made small organic acid produced during metabolism and exercise.

Levulinic acid

An organic keto acid (contains a ketone functionality) produced from cellulose.

Lignin

A highly complex biopolymer often obtained from tree barks. It has great potential to be used as biomass to generate bioproducts.

Linoleic acid

A natural polyunsaturated omega-6 fatty acid.

Lipophilic

The property of non-polar molecule to be soluble in hydrocarbon-rich, non-polar, lipid and lipid-like compounds.

Lubricants

A material developed to enhance the mobility of two moving surfaces that are in mutual contact, reduce friction, and heat in order to prevent wear and tear of the moving parts.

Macerated oils

Macerated oils are extracted directly from plants and ready for use with an oil base.

Maltose

A disaccharide made from two glucose units.

Menthol

A cyclic organic alcohol isolated from mint plants and has various medical applications.

Micelle

A spherical assembly of amphiphilic compounds with a polar head and non-polar tails organized with the polar tips around the exposed surface.

Monolaurin

A monoglyceride meaning a glycerol molecule with one of its three hydroxy groups forming an ester bond with a long chain fatty acid.

Monosaccharides

The smallest sugars containing one cyclic group, viz. glucose, fructose, and galactose.

Naphthalene

A bicyclic, crystalline, volatile aromatic compound often used as an insect repellant.

Nylon

A commercially viable synthetic polymer containing an amide bond attaching the monomers together.

Octane value

A measure of the performance of a liquid fuel relevant to the type of the engine it is being used for.

Organic catalysts

Organic molecules capable of catalyzing a chemical reaction by increasing the rate of the reaction.

Organometallic catalysts

Organometallic catalysts differ from organic catalysts by having one or more metal elements.

Oxidant

A compound capable of reacting with another compound by either providing with oxygen or removing hydrogens. An oxidant removes electron(s) from the other compound.

Pesticides

Synthetic or natural compounds that eliminate pests.

Petrochemicals

Commercially useful chemicals derived from fossil fuels.

Petrodiesel

Diesel derived from fossil fuels.

Petroproducts

Commercial products made from fossil fuel-resourced ingredients.

Pharmacokinetic (PK)

Pharmacokinetic (PK) properties describe the properties of a medicinal agent moving through a living system.

Phenol

An acidic aromatic alcohol originally isolated from coal tar. It is widely used in polymer and medicinal industries.

Photosynthesis

The natural process by which plants use chlorophyll as a biocatalyst to convert light energy into storable chemical energy in carbohydrate molecules.

Plant oils

Oily natural compounds extracted from plants ready for human use with or without other substances.

Plasticizers

Additives to increase plasticity of materials.

Polyester

Synthetic polymer containing repetitive ester bonds in between the monomeric units.

Polyglycols

Polymers containing repeating monomeric units of glycols (1,2,3-trihydroxy propane).

Polylactides

Polymers containing repeating monomeric lactic acid units.

Polysaccharides

Natural polymeric compounds made of repeating monomeric units of monosaccharides connected together with a glycosidic bond.

Polyurethane

Synthetic polymer containing urea bonds between the repeating monomeric units.

Producer gas

Commercial gases or mixture of gases, viz. town gas and syngas.

Pyrolysis oil

Renewable biomass-derived synthetic fuel and a possible alternative to fossil fuel.

Quercetin

Naturally occurring flavonol (tricyclic polyphenolic compound) used in supplements and foods.

Renewable biomass

The natural feedstock alternative to fossil fuel-derived substances for the generation of commercial products.

Renewable feedstocks

See renewable biomass.

Resins

Thick, often sticky liquid secretions from specific plants and trees that have commercial use.

Salicylic acid

A nature-made aromatic phenolic carboxylic acid. It is widely used in variety of organic synthesis and contributes significantly to the structure of aspirin.

Saponification

Base-catalyzed hydrolysis of an ester moiety (functionality/bond) into an alcohol and carboxylate salts of the free carboxylic acid.

Short-chain fatty acids (SCFA)

Natural carboxylic acids with the aliphatic hydrocarbon chain not exceeding six carbons.

Sodium dodecyl sulfate (SDS)

It is the sodium salt of dodecyl sulfate—an amphiphilic molecule that has widespread usage as a surfactant.

Sorbitol

A straight-chain poly-alcohol derived from glucose and used as a sweetener.

Starch

It is a natural polysaccharide and a plant product stitched together from glucose units. It is one of the most common carbohydrate sources for humans.

Succinic acid

A natural diacid containing four carbons used in food and polymer industries.

Sugar

The natural, water-soluble carbohydrates can be mono- or disaccharides with a sweetening property.

Surfactants

Generally long hydrocarbon chain containing molecules with polar heads. They possess the amphiphilic property of liking both aqueous and non-polar media, thus can form micelles and act as surfactants.

Sustainable biomass

Biological feedstock or starting materials for the generation of various commercial end products that can be regenerated. The production, isolation, use, and waste management of sustainable biomass are expected to be environment friendly and less hazardous.

Sustainable chemistry

Energy produced from sustainable biomass and not fossil fuel-related resources.

Syngas

Synthetic gas that is a mixture of hydrogen and carbon monoxide primarily.

Synthetic building blocks

Unnatural smaller chemical fragments that can be used as segments or blocks in the synthesis of a larger target molecule.

Synthetic schemes

The multi-step chemical process starting from commercially accessible starting materials to produce the final target molecule is generally known as the synthetic scheme. A plan or strategy could constitute a ‘chemical scheme’ as well.

Synthons

Synthetic building blocks or pieces that are joined together carefully in a multi-step chemical process to yield the final target product.

Terpenoid

Large natural organic molecules where repeating monomeric isoprene units can be found as building blocks.

Thymol

A natural monoterpene phenolic compound responsible for the distinctive smell of thyme.

Trans -esterification

Conversion of an existing ester molecule to a different ester by an exchange reaction with an alcohol catalyzed by a base or an acid.

Triglyceride (TG)

A naturally occurring fat or lipid containing one unit of glycerol and three units of identical or different fatty acids bonded together through three ester bonds.

Vanillin

A natural monocyclic, aromatic, phenolic aldehyde often used as a flavoring agent.

Vegetable fats

A triglyceride fat found or extracted from a plant.

Vegetable oil

See vegetable fat.

Zein

It is a natural protein found in corn.