1,4-BUTANEDIOIC ACID

CAS NO:110-15-6
EC NO:203-740-4

1,4-Butanedioic acid  is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. The name derives from Latin succinum, meaning amber. In living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state.

1,4-Butanedioic acid is marketed as food additive E363. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). 
1,4-Butanedioic acid can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling. As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome, and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury.

Properties:
Chemical formula:    C4H6O4
Molar mass:    118.088 g·mol−1
Density:    1.56 g/cm3
Melting point:    184–190 °C (363–374 °F; 457–463 K)
Boiling point:    235 °C (455 °F; 508 K)
Solubility in water:    58 g/L (20 °C)or 100 mg/mL

Physical properties
1,4-Butanedioic acid is a white, odorless solid with a highly acidic taste. In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate . As a diprotic acid, succinic acid undergoes two successive deprotonation reactions:

(CH2)2(CO2H)2 → (CH2)2(CO2H)(CO2)− + H+(CH2)2(CO2H)(CO2)− → (CH2)2(CO2)22− + H+
The pKa of these processes are 4.3 and 5.6, respectively. Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2. In living organisms, primarily succinate, not succinic acid, is found.

As a radical group it is called a succinyl group.

Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes.

Commercial production
Historically, 1,4-Butanedioic acid was obtained from amber by distillation and has thus been known as spirit of amber. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. Succinate is also produced from butane via maleic anhydride.Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%.

Genetically engineered Escherichia coli and Saccharomyces cerevisiae are proposed for the commercial production via fermentation of glucose.

Chemical reactions
1,4-Butanedioic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. This diethyl ester is a substrate in the Stobbe condensation. Dehydration of succinic acid gives succinic anhydride. 
1,4-Butanedioic acid can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran.

Applications

1,4-Butanedioic acid is a precursor to some polyesters and a component of some alkyd resins. 1,4-Butanediol (BDO) can be synthesized using 1,4-Butanedioic acid as a precursor.The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams.
1,4-Butanedioic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications.

Acylation with succinic acid is called succination. Oversuccination occurs when more than one succinate adds to a substrate.

Food and dietary supplement
As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration.
1,4-Butanedioic acid is used primarily as an acidity regulator in the food and beverage industry. 
1,4-Butanedioic acid is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. As an excipient in pharmaceutical products, it is also used to control acidity or as a counter ion. Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate.

1,4-Butanedioic acid, also known as ethylenesuccinate or butanedionic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. 
1,4-Butanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 
1,4-Butanedioic acid exists in all living species, ranging from bacteria to humans. 
1,4-Butanedioic acid is a potentially toxic compound.

Uses
1,4-Butanedioic acid is an acidulant that is commercially prepared by the hydrogenation of maleic or fumaric acid. 
1,4-Butanedioic acid is a nonhygroscopic acid but is more soluble in 25°c water than fumaric and adipic acid. 
1,4-Butanedioic acid has low acid strength and slow taste build-up; it is not a substitute for normal acidulants. 
1,4-Butanedioic acid combines with proteins in modifying the plasticity of bread dough. 
1,4-Butanedioic acid functions as an acidulant and flavor enhancer in relishes, beverages, and hot sausages.

1,4-Butanedioic acid is a dicarboxylic acid. 
1,4-Butanedioic acid is a common intermediate in the metabolic pathway of several anaerobic and facultative micro-organisms.
1,4-Butanedioic acid is used as a dietary supplement for symptoms related to menopause such as hot flashes and irritability. 
1,4-Butanedioic acid is used as a flavoring agent for food and beverages. 
1,4-Butanedioic acid is used to manufacture polyurethanes, paints and coatings, adhesives, sealants, artificial leathers, cosmetics and personal care products, biodegradable plastics, nylons, industrial lubricants, phthalate-free plasticizers, and dyes & pigments. In the pharmaceutical industry, it is used in the preparation of active calcium succinate, as a starting material for active pharmaceutical ingredients (adipic acid, N-methyl pyrrolidinone, 2-pyrrolidinone, succinate salts, etc.), as an additive in drug formation, for medicines of sedative, antispasmer, antiplegm, antiphogistic, anrhoter, contraception and cancer curing, in the preparation of vitamin A and anti-Inflammatory, and as antidote for toxic substance.

Chemical Properties
1,4-Butanedioic acid is a normal constituent of almost all plant and animal tissues. 
1,4-Butanedioic acid is the dehydration product of the acid. 
1,4-Butanedioic acid was first obtained as the distillate from amber (Latin, Succinum) for which it is named. 
1,4-Butanedioic acid occurs in beet, brocoli, rhubarb, sauerkraut, cheese, meat, molasses, eggs, peat, coal, fruits, honey, and urine (Gardner, 1972; Winstrom, 1978; Doores, 1989). 
1,4-Butanedioic acid is formed by the chemical and biochemical oxidation of fats, by alcoholic fermentation of sugar, and in numerous catalyzed oxidation processes. 
1,4-Butanedioic acid is also a major byproduct in the manufacture of adipic acid.
1,4-Butanedioic acid, a dicarboxylic acid, is a relatively new nonhygroscopic product approved for food uses. 
1,4-Butanedioic acids apparent taste characteristics in foods appear to be very similar to the other acidulants of this type, although pure aqueous solutions tend to have a slightly bitter taste. 
1,4-Butanedioic acid, in contrast, is the only commercially available anhydride for food uses (Gardner, 1972).

Uses
1,4-Butanedioic acid (COOH(CH2)2COOH) is a carboxylic acid used in food (as an acidulant), pharmaceutical (as an excipient), personal care (soaps) and chemical (pesticides, dyes and lacquers) industries. Bio-based succinic acid is seen as an important platform chemical for the production of biodegradable plastics and as a substitute of several chemicals (such as adipic acid).
1,4-Butanedioic acid is widely used in the food industry as a chelating agent and as a pH adjuster. The FDA has granted Succinic Acid with the GRAS status (Generally Recognised as Safe Substance). 
1,4-Butanedioic acid is also used as an intermediate to manufacture several chemicals, amongst which raw materials for the cosmetic and personal-care industry, e.g. emollients, surfactants and emulsifiers.

Preparation
1,4-Butanedioic acid can also be manufactured by catalytic hydrogenation of malic or fumaric acids. 
1,4-Butanedioic acid has also been produced commercially by aqueous acid or alkalihydrolysis of succinonitrile derived from ethylene bromide and potassium cyanide (Gergel and Revelise, 1952; Gardner, 1972).
Today succinic acid is mainly produced from fossil resources through maleic acid hydrogenation. 
1,4-Butanedioic acid can also be produced through fermentation of sugars. In that case, in addition to succinic acid, other carboxylic acids (such as lactic acid, formic acid, propionic acid) and alcohols (such as ethanol) are also obtained.

1,4-Butanedioic acid is a dicarboxylic acid with chemical formula (CH2)2(CO2H)2.
1,4-Butanedioic acid is a white, odorless solid. In an aqueous solution, it ionizes to anions (that is, conjugates to a conjugate base) called succinate, which plays a role in the citric acid cycle, an energy-yielding process in all living organisms. As a radical group it is called a succinyl group. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.

1). In basic organic chemical raw materials, 1,4-Butanedioic acid could be used in painting, dyes, adhesive, medicine and so on; 
1,4-Butanedioic acid could also be used in the usage of paper manufacturing and textile industry; This chemical could be applied as the raw material for lubricant, photographic chemicals and surface active agent.

2).In medicine industry, Succinic acid（cas 110-15-6） could be used in the synthesis of sedative, diuretic, vitamin, contraceptive and cancer drugs.

3). In chemical industry, 1,4-Butanedioic acid could be used as the modifier of PH value when in electroplating, strengthening agent for plastics. And it is also applied in productions of spray paint, dyes, ion exchange resin, pesticide and so on. Secondly, this could be used as the intermediate of fine chemicals and organic synthesis. This chemical has wide application, including dyes, organic pigments, rubber vulcanization accelerator, alkyd resin, adhesive, lubricants, papermaking chemicals, plant growth promoters, photographic chemicals, surface active agent, ion/change resin, pesticide, fungicide and cosmetics.

4). 1,4-Butanedioic acid could be applied as one kind of standard reagent for Alkalimetry, buffer and contrast samples for gas chromatography. Besides, it could be used in the synthesis of dyes and paintings.

5). In food industry, Succinic acid（cas 110-15-6） could be used with slight dose. 1,4-Butanedioic acid is one kind of food acids which is applied in the seasoning of wine, feed, and candy. And we would like to introduce one kind of food-grade 1,4-Butanedioic acid, with the detailed information below:
Appearance colourless to white crystal or white crystal powder

1,4-Butanedioic acid acts as a leaching agent in extracting lithium, cobalt from used Li-ion batteries and magnesium from magnesite ore. 
1,4-Butanedioic acid is used as a starting material in the synthesis of new elastic polyesters, fumaric acid, succinic anhydride and alkyd resins. 
1,4-Butanedioic acid plays an important role as an acidity regulator in the food and beverage industry, as an excipient in pharmaceutical products and acts as a cocrystallising agent in organic synthesis. 
1,4-Butanedioic acids derivative viz diethyl ester is used as a substrate in the Stobbe condensation.

1,4-Butanedioic acid appears as white crystals or shiny white odorless crystalline powder.
1,4-Butanedioic acid is an alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. 
1,4-Butanedioic acid is an intermediate metabolite in the citric acid cycle. 
1,4-Butanedioic acid has a role as a nutraceutical, a radiation protective agent, an anti-ulcer drug, a micronutrient and a fundamental metabolite. 
1,4-Butanedioic acid is an alpha,omega-dicarboxylic acid and a C4-dicarboxylic acid. 
1,4-Butanedioic acid is a conjugate acid of a succinate(1-).

Industry Uses:    
-Adsorbents and absorbents
-Corrosion inhibitors and anti-scaling agents
-Intermediates
-Plasticizers
-Processing aids, not otherwise listed

Consumer Uses:    
-Adhesives and sealants
-Water treatment products

Industry Processing Sectors:
-All other basic organic chemical manufacturing
-Plastic material and resin manufacturing
-Utilities

Use    
-1,4-Butanedioic acid is mainly used for the preparation of succinic anhydride, succinic acid esters and other derivatives, used as raw materials for coatings, dyes, adhesives, drugs and so on
-1,4-Butanedioic acid is used as an alkaline method standard reagent, a buffer, and a gas chromatography comparative sample. For the determination of cerium, copper, lanthanum, scandium, ytterbium, yttrium, nitrite, determination of iron, lead.

About 1,4-Butanedioic acid
Helpful information
1,4-Butanedioic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.

1,4-Butanedioic acid is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses
1,4-Butanedioic acid is used in the following products: adsorbents, fertilisers, inks and toners, washing & cleaning products, water softeners, adhesives and sealants, coating products, fillers, putties, plasters, modelling clay, perfumes and fragrances, pharmaceuticals, polymers and cosmetics and personal care products.
Other release to the environment of 1,4-Butanedioic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Article service life
ECHA has no public registered data on the routes by which 1,4-Butanedioic acid is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers
1,4-Butanedioic acid is used in the following products: pH regulators and water treatment products, anti-freeze products, metal surface treatment products, heat transfer fluids, hydraulic fluids, washing & cleaning products, fertilisers, water softeners and cosmetics and personal care products. 1,4-Butanedioic acid is used in the following areas: printing and recorded media reproduction, health services and scientific research and development. 1,4-Butanedioic acid is used for the manufacture of: plastic products. Other release to the environment of 1,4-Butanedioic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids).

Formulation or re-packing
1,4-Butanedioic acid is used in the following products: washing & cleaning products, water softeners, cosmetics and personal care products, non-metal-surface treatment products, inks and toners, paper chemicals and dyes and polymers.
Release to the environment of 1,4-Butanedioic acid can occur from industrial use: formulation of mixtures.

Uses at industrial sites
1,4-Butanedioic acid is used in the following products: pH regulators and water treatment products, metal surface treatment products, leather treatment products, metal working fluids and laboratory chemicals.
1,4-Butanedioic acid is used in the following areas: municipal supply (e.g. electricity, steam, gas, water) and sewage treatment, scientific research and development and printing and recorded media reproduction.
1,4-Butanedioic acid is used for the manufacture of: chemicals, plastic products and textile, leather or fur.
Release to the environment of 1,4-Butanedioic acid can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture, in the production of articles and as processing aid.

Manufacture
Release to the environment of 1,4-Butanedioic acid can occur from industrial use: manufacturing of the substance.

IUPAC names:
1,4-Butanedioic acid
Butanedioic Acid
Butanedioic acid
butanedioic acid
Butanedionic acid
Ethanedicarboxylic acid
Succinic
SUCCINIC ACID
Succinic Acid
Succinic acid
succinic acid
Succinic Acid
Succinic acid
succinic acid

SYNONYMS:
1,2-Ethanedicarboxylic acid
1,4-Butanedioic acid
110-15-6 [RN]
203-740-4 [EINECS]
4-02-00-01908 [Beilstein]
Acide butanedioique [French]
Acide succinique [French] [ACD/IUPAC Name]
Acido succinico [Italian]
ácido succínico [Spanish]
Ácido succínico [Portuguese]
acidum succinicum [Latin]
Bernsteinsaeure [German]
Bernsteinsäure [German] [ACD/IUPAC Name]
Butanedioic acid [ACD/Index Name]
HOOC-CH2-CH2-COOH [Formula]
Kyselina jantarova [Czech]
MFCD00002789 [MDL number]
QV2VQ [WLN]
Succinic acid [ACD/IUPAC Name] [Wiki]
Succinic acid
Ηλεκτρικό οξύ [Modern Greek (1453-)]
Янтарная кислота [Russian]
コハク酸 [Japanese]
琥珀酸 [Chinese]
14493-42-6 [RN]
152556-05-3 [RN]
21668-90-6 [RN]
61128-08-3 [RN]
acidum succinicum
amber acid
asuccin
Bernsteinsaeure
Bernsteinsaure
Butandisaeure
BUTANE DIACID
BUTANEDIOICACID
CpeE protein
DB00139
Dihydrofumaric acid
Ethanedicarboxylic acid
Ethylene dicarboxylic acid
Ethylene succinic acid
FMR
fum
Fumaric acid [Wiki]