Fumaric acid is a dicarboxylic acid that occurs naturally in some plants and fungi. The chemical formula is HO2CCH=CHCO2H. It is a colorless crystalline solid that is slightly soluble in water and very soluble in alcohol. In this article, we will discuss the properties, uses and production of fumaric acid.
Chemical Properties
Fumaric acid belongs to the family of unsaturated dicarboxylic acids. It has a double bond between the two carboxyl groups which gives it unique reactivity. Some key chemical properties of fumaric acid include:
– It exists as a white crystalline solid at room temperature. Its melting point is 286°C.
– It is odorless and possesses a slightly acidic taste.
– Being an unsaturated compound, it is prone to addition reactions. It readily reacts with halogens, hydrogen halides, etc by addition to the double bond.
– It undergoes dimerization reaction under certain conditions to form maleic acid, which has an anhydride functional group.
– Its salts known as fumarates are colorless crystalline compounds. Fumaric Acid forms 1:1 salts with metals and organic bases.
– It is stable under normal pH and temperatures but slowly decomposes above 200°C producing volatile products like carbon dioxide and water.
Natural Occurrence and Production
Fumaric acid was first isolated from fungi-infected fumitory plants, which is how it derives its name. It occurs naturally in some plant species like lichens and Iceland moss. On an industrial scale, it is produced by fermentation. Some ways fumaric acid is obtained include:
– Fermentation of carbohydrate feedstocks: Glucose is fermented by fungi like Rhizopus species to produce fumaric acid in large fermentation tanks along with other organic acids. This is the predominant production method.
– Dehydration of maleic acid: Heating maleic acid above 200°C causes loss of a water molecule to form fumaric acid in a chemical dehydration reaction.
– Decarboxylation of malic acid: Malic acid undergoes thermal decarboxylation to lose one carbon dioxide molecule forming fumaric acid. However, this route is not economically viable.
The global fumaric acid production capacity is over 200 kilo tons per year. China is currently the largest producer followed by markets like Germany, Italy and the United States.
Uses and Applications
The versatility of fumaric acid arises from its two carboxylic acid functional groups as well as the double bond present. It has wide commercial applications mainly as:
Unsaturated polyester resin production: Fumaric acid is used to make unsaturated polyester resins which are used to manufacture products like builders’ putty, fiberglass reinforced plastics, sinks, tubs, etc. The double bond in fumaric acid backbone reacts with and crosslinks styrene monomers during resin synthesis.
Alkyd resin manufacturing: The crosslinking ability of fumaric acid also makes it a common component in alkyd resins formulations which are used in paints, coatings and varnishes industries. Fumaric acid improves the properties of finished resins.
Food additive: It has been approved by the FDA as a food additive called E297. In the food industry, fumaric acid is used as an acidity regulator, pH buffer and flavoring agent in products like processed meats, baked goods, snacks and beverages. Its E number and acidity makes it suitable.
Animal feed: A small amount of fumaric acid is mixed in animal feed as a preservative and to improve nutrient digestion. It acts against microbes and protects proteins from degradation in the feed.
Pharmaceuticals: In pharmacy, it is applied as an ingredient in medications ranging from ointments, gels to supplements owing to its antimicrobial effects. It helps treat skin conditions, assists growth and strengthens immunity.
As is evident, the unique double bond and acid groups of fumaric acid allow its incorporation in a diverse array industries and applications utilizing its crosslinking, buffering and antimicrobial attributes. With growing worldwide demand, its production and usage will further rise in the foreseeable future.
Health Benefits and Side Effects
Along with industrial uses, fumaric acid has certain health benefits when consumed as a nutritional supplement:
– It may help reduce psoriasis symptoms as its identical structure to citric acid allows it to slow skin cell division aiding psoriasis treatment. However, no definitive evidence yet.
– Being an organic acid, it works as an antioxidant and fights against free radicals in the body conferring some heart and brain health protections.
– Preliminary research hints it may benefit people with multiple sclerosis (MS) by reduction of inflammation and repair of damaged myelin sheaths. However, clinical trials are still ongoing.
– Supplementation strengthens bone health and joint function. It provides a natural joint lubricant and repair aid for arthritis patients.
– At the same time, in excessive doses fumaric acid can lead to minor gastrointestinal side effects like nausea, vomiting, abdominal pain due to its acidic property on intestinal lining.
– Long term intake in very high amounts above recommended levels may potentially damage kidney function over time. More safety data is required for such risks.
Despite promising results, more rigorous human studies are still warranted to verify all health outcomes and any potential side effects from chronic usage, optimal dosage, duration etc. but overall it is considered generally safe.
Future Outlook
Going forward, with development of new technologies and expansion of existing industries, the fumaric acid market demand is projected to keep growing steadily. Expanding biosynthetic routes, improving fermentation yields and recovery methods can help bolster production abilities to meet the rising needs. Some expected future trends include:
– Novel polymeric applications in biodegradable plastics, coatings, foams with enhanced sustainability.
– Development of micronutrient dietary supplements and cosmeceuticals leveraging its antioxidant functions.
– Use as building block chemical in producing precursors for agrochemicals, pharmaceutical intermediates, fuel additives expanding scope.
– Genetic engineering of efficient microbial strains for industrial scale fumaric acid biosynthesis through fermentation at lower costs.
– Recovery technologies to retrieve and reuse unutilized fumaric acid from various industrial processes improving process efficiencies.
Note:
1. Source: Coherent Market Insights, Public sources, Desk research
2. We have leveraged AI tools to mine information and compile it
