Propionic acid

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Contents

Propionic acid
Simplified skeletal formula Propionic acid chemical structure.svg
Simplified skeletal formula
Full structural formula Propionic acid flat structure.png
Full structural formula
Ball-and-stick model Propionic-acid-3D-balls.png
Ball-and-stick model
Space-filling model Propionic acid spheres.png
Space-filling model
Propionic acid.jpg
Names
Preferred IUPAC name
Propanoic acid
Other names
Carboxyethane
Ethanecarboxylic acid
Ethylformic acid
Metacetonic acid
Methylacetic acid
C3:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.070 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • Propionic acid:201-176-3
E number E280 (preservatives)
  • Propionic acid: 1062
PubChem CID
RTECS number
  • Propionic acid:UE5950000
UNII
  • InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5) Yes check.svgY
    Key: XBDQKXXYIPTUBI-UHFFFAOYSA-N Yes check.svgY
  • Propionic acid:CCC(=O)O
  • Propionate:CCC(=O)[O-]
Properties
C3H6O2
Molar mass 74.079 g·mol−1
AppearanceColorless, oily liquid [1]
Odor Pungent, rancid, unpleasant [1]
Density 0.98797 g/cm3 [2]
Melting point −20.5 °C (−4.9 °F; 252.7 K) [3]
Boiling point 141.15 °C (286.07 °F; 414.30 K) [3]
Sublimes at −48 °C
ΔsublHo = 74 kJ/mol [4]
8.19 g/g (−28.3 °C)
34.97 g/g (−23.9 °C)
Miscible (≥ −19.3 °C) [5]
Solubility Miscible in EtOH, ether, CHCl
3 [6]
log P 0.33 [7]
Vapor pressure 0.32 kPa (20 °C) [8]
0.47 kPa (25 °C) [7]
9.62 kPa (100 °C) [4]
4.45·10−4 L·atm/mol [7]
Acidity (pKa)4.88 [7]
-43.50·10−6 cm3/mol
1.3843 [2]
Viscosity 1.175 cP (15 °C) [2]
1.02 cP (25 °C)
0.668 cP (60 °C)
0.495 cP (90 °C) [7]
Structure
Monoclinic (−95 °C) [9]
P21/c [9]
a = 4.04 Å, b = 9.06 Å, c = 11 Å [9]
α = 90°, β = 91.25°, γ = 90°
0.63 D (22 °C) [2]
Thermochemistry
152.8 J/mol·K [6] [4]
Std molar
entropy (S⦵298)
191 J/mol·K [4]
−510.8 kJ/mol [4]
1527.3 kJ/mol [2] [4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive
GHS labelling: [8]
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H314 [8]
P280, P305+P351+P338, P310 [8]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 54 °C (129 °F; 327 K) [8]
512 °C (954 °F; 785 K)
Lethal dose or concentration (LD, LC):
1370 mg/kg (mouse, oral) [6]
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
TWA 10 ppm (30 mg/m3) ST 15 ppm (45 mg/m3) [1]
IDLH (Immediate danger)
N.D. [1]
Related compounds
Acetic acid
Lactic acid
3-Hydroxypropionic acid
Tartronic acid
Acrylic acid
Butyric acid
Related compounds
 1-Propanol
Propionaldehyde
Sodium propionate
Propionic anhydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Propionic acid ( /proʊpiˈɒnɪk/ , from the Greek words πρῶτος : prōtos, meaning "first", and πίων : píōn, meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH
3CH
2CO
2H. It is a liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH
3CH
2CO−
2 as well as the salts and esters of propionic acid are known as propionates or propanoates.

About half of the world production of propionic acid is consumed as a preservative for both animal feed and food for human consumption. It is also useful as an intermediate in the production of other chemicals, especially polymers.

History

Propionic acid was first described in 1844 by Johann Gottlieb, who found it among the degradation products of sugar. [10] Over the next few years, other chemists produced propionic acid by different means, none of them realizing they were producing the same substance. In 1847, French chemist Jean-Baptiste Dumas established all the acids to be the same compound, which he called propionic acid, from the Greek words πρῶτος (prōtos), meaning first, and πίων (piōn), meaning fat, because it is the smallest H(CH
2)
nCOOH acid that exhibits the properties of the other fatty acids, such as producing an oily layer when salted out of water and having a soapy potassium salt. [11]

Properties

Propionic acid has physical properties intermediate between those of the smaller carboxylic acids, formic and acetic acids, and the larger fatty acids. It is miscible with water, but can be removed from water by adding salt. As with acetic and formic acids, it consists of hydrogen bonded pairs of molecules in both the liquid and the vapor.

Propionic acid displays the general properties of carboxylic acids: it can form amide, ester, anhydride, and chloride derivatives. It undergoes the Hell–Volhard–Zelinsky reaction that involves α-halogenation of a carboxylic acid with bromine, catalysed by phosphorus tribromide, in this case to form 2-bromopropanoic acid, CH
3CHBrCOOH. [12] This product has been used to prepare a racemic mixture of alanine by ammonolysis. [13] [14]

Preparation of alanine from propionic acid.png

Manufacture

Chemical

In industry, propionic acid is mainly produced by the hydrocarboxylation of ethylene using nickel carbonyl as the catalyst: [15]

Industrial synthesis of propionic acid (hydrocarboxylation process).svg

It is also produced by the aerobic oxidation of propionaldehyde. In the presence of cobalt or manganese salts (manganese propionate is most commonly used), this reaction proceeds rapidly at temperatures as mild as 40–50 °C:

Industrial synthesis of propionic acid (oxidation process).svg

Large amounts of propionic acid were once produced as a byproduct of acetic acid manufacture. At the current time, the world's largest producer of propionic acid is BASF, with approximately 150 kt/a production capacity.

Biotechnological

Biotechnological production of propionic acid mainly uses Propionibacterium strains. [16] However, large scale production of propionic acid by Propionibacteria faces challenges such as severe inhibition of end-products during cell growth and the formation of by-products (acetic acid and succinic acid). [17] One approach to improve productivity and yield during fermentation is through the use of cell immobilization techniques, which also promotes easy recovery, reuse of the cell biomass and enhances microorganisms' stress tolerance. [18] In 2018, 3D printing technology was used for the first time to create a matrix for cell immobilization in fermentation. Propionic acid production by Propionibacterium acidipropionici immobilized on 3D-printed nylon beads was chosen as a model study. It was shown that those 3D-printed beads were able to promote high density cell attachment and propionic acid production, which could be adapted to other fermentation bioprocesses. [19] Other cell immobilization matrices have been tested, such as recycled-glass Poraver and fibrous-bed bioreactor. [20] [21]

Alternative methods of production have been trialled, by genetically engineering strains of Escherichia coli to incorporate the necessary pathway, the Wood-Werkman cycle. [22]

Industrial uses

Propionic acid inhibits the growth of mold and some bacteria at levels between 0.1 and 1% by weight. As a result, some propionic acid produced is consumed as a preservative for both animal feed and food for human consumption. For animal feed, it is used either directly or as its ammonium salt. This application accounts for about half of the world production of propionic acid. The antibiotic monensin is added to cattle feed to favor propionibacteria over acetic acid producers in the rumen; this produces less carbon dioxide and feed conversion is better. Another major application is as a preservative in baked goods, which use the sodium and calcium salts. [15] As a food additive, it is approved for use in the EU, [23] US, [24] Australia and New Zealand. [25]

Propionic acid is also useful as an intermediate in the production of other chemicals, especially polymers. Cellulose-acetate-propionate is a useful thermoplastic. Vinyl propionate is also used. In more specialized applications, it is also used to make pesticides and pharmaceuticals. The esters of propionic acid have fruit-like odors and are sometimes used as solvents or artificial flavorings. [15]

In biogas plants, propionic acid is a common intermediate product, which is formed by fermentation with propionic acid bacteria. Its degradation in anaerobic environments (e.g. biogas plants) requires the activity of complex microbial communities. [26]

In production of the Jarlsberg cheese a propionic acid bacteria is used to give both taste and holes. [27]

Biology

Propionic acid is produced biologically as its coenzyme A ester, propionyl-CoA, from the metabolic breakdown of fatty acids containing odd numbers of carbon atoms, and also from the breakdown of some amino acids. Bacteria of the genus Propionibacterium produce propionic acid as the end-product of their anaerobic metabolism. This class of bacteria is commonly found in the stomachs of ruminants and the sweat glands of humans, and their activity is partially responsible for the odor of Emmental cheese, American "Swiss cheese" and sweat.

The metabolism of propionic acid begins with its conversion to propionyl coenzyme A, the usual first step in the metabolism of carboxylic acids. Since propionic acid has three carbons, propionyl-CoA cannot directly enter either beta oxidation or the citric acid cycles. In most vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is isomerised to L-methylmalonyl-CoA. A vitamin B12-dependent enzyme catalyzes rearrangement of L-methylmalonyl-CoA to succinyl-CoA, which is an intermediate of the citric acid cycle and can be readily incorporated there. [28]

Propionic acid serves as a substrate for hepatic gluconeogenesis via conversion to succinyl-CoA. [29] [30] Additionally, exogenous propionic acid administration results in more endogenous glucose production than can be accounted for by gluconeogenic conversion alone. [31] Exogenous propionic acid may upregulate endogenous glucose production via increases in norepinephrine and glucagon, suggesting that chronic ingestion of propionic acid may have adverse metabolic consequences. [32]

In propionic acidemia, a rare inherited genetic disorder, propionate acts as a metabolic toxin in liver cells by accumulating in mitochondria as propionyl-CoA and its derivative, methylcitrate, two tricarboxylic acid cycle inhibitors. Propanoate is metabolized oxidatively by glia, which suggests astrocytic vulnerability in propionic acidemia when intramitochondrial propionyl-CoA may accumulate. Propionic acidemia may alter both neuronal and glial gene expression by affecting histone acetylation. [33] [34] When propionic acid is infused directly into rodents' brains, it produces reversible behavior (e.g., hyperactivity, dystonia, social impairment, perseveration) and brain changes (e.g., innate neuroinflammation, glutathione depletion) that may be used as a means to model autism in rats. [33]

Human occurrence

The human skin is host of several species of Propionibacteria. The most notable one is the Cutibacterium acnes (formerly known as Propionibacterium acnes), which lives mainly in the sebaceous glands of the skin and is one of the principal causes of acne. [35] Propionate is observed to be among the most common short-chain fatty acids produced in the large intestine of humans by gut microbiota in response to indigestible carbohydrates (dietary fiber) in the diet. [36] [37] The role of the gut microbiota and their metabolites, including propionate, in mediating brain function has been reviewed. [38]

A study in mice suggests that propionate is produced by the bacteria of the genus Bacteroides in the gut, and that it offers some protection against Salmonella there. [39] Another study finds that fatty acid propionate can calm the immune cells that drive up blood pressure, thereby protecting the body from damaging effects of high blood pressure. [40]

Bacteriology

The Bacteria species Coprothermobacter platensis produces propionate when fermenting gelatin. [41] Prevotella brevis and Prevotella ruminicola also generate propionate when fermenting glucose. [42]

Propionate salts and esters

The propionate /ˈproʊpiəneɪt/ , or propanoate, ion is C
2 H
5COO−
, the conjugate base of propionic acid. It is the form found in biological systems at physiological pH. A propionic, or propanoic, compound is a carboxylate salt or ester of propionic acid. In these compounds, propionate is often written in shorthand, as CH
3CH
2CO
2 or simply EtCO
2.

Propionates should not be confused with propenoates (commonly known as acrylates), the ions/salts/esters of propenoic acid (also known as 2-propenoic acid or acrylic acid).

Examples

Salts

Esters

See also

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, containing the group –SO2OH, are relatively stronger acids. Alcohols, with –OH, can act as acids but they are usually very weak. The relative stability of the conjugate base of the acid determines its acidity. Other groups can also confer acidity, usually weakly: the thiol group –SH, the enol group, and the phenol group. In biological systems, organic compounds containing these groups are generally referred to as organic acids.

<span class="mw-page-title-main">Butyric acid</span> Chemical compound

Butyric acid, also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid is an isomer. Salts and esters of butyric acid are known as butyrates or butanoates. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical and an important component in the mammalian gut.

<i>Cutibacterium acnes</i> Species of bacterium

Cutibacterium acnes is the relatively slow-growing, typically aerotolerant anaerobic, gram-positive bacterium (rod) linked to the skin condition of acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. Its genome has been sequenced and a study has shown several genes can generate enzymes for degrading skin and proteins that may be immunogenic.

<i>Propionibacterium</i> Genus of bacteria

Propionibacterium is a gram-positive, anaerobic, rod-shaped genus of bacteria named for their unique metabolism: They are able to synthesize propionic acid by using unusual transcarboxylase enzymes.

In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups. The general molecular formula for dicarboxylic acids can be written as HO2C−R−CO2H, where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.

Acidogenesis is the second stage in the four stages of anaerobic digestion:

Calcium propanoate or calcium propionate has the formula Ca(C2H5COO)2. It is the calcium salt of propanoic acid.

<span class="mw-page-title-main">Bioconversion of biomass to mixed alcohol fuels</span>

The bioconversion of biomass to mixed alcohol fuels can be accomplished using the MixAlco process. Through bioconversion of biomass to a mixed alcohol fuel, more energy from the biomass will end up as liquid fuels than in converting biomass to ethanol by yeast fermentation.

Propionyl-CoA is a coenzyme A derivative of propionic acid. It is composed of a 24 total carbon chain and its production and metabolic fate depend on which organism it is present in. Several different pathways can lead to its production, such as through the catabolism of specific amino acids or the oxidation of odd-chain fatty acids. It later can be broken down by propionyl-CoA carboxylase or through the methylcitrate cycle. In different organisms, however, propionyl-CoA can be sequestered into controlled regions, to alleviate its potential toxicity through accumulation. Genetic deficiencies regarding the production and breakdown of propionyl-CoA also have great clinical and human significance.

<span class="mw-page-title-main">Methylmalonic acid</span> Chemical compound

Methylmalonic acid (MMA) is a chemical compound from the group of dicarboxylic acids. It consists of the basic structure of malonic acid and also carries a methyl group. The salts of methylmalonic acid are called methylmalonates.

Short-chain fatty acids (SCFAs) are fatty acids of two to six carbon atoms. The SCFAs' lower limit is interpreted differently, either with one, two, three or four carbon atoms. Derived from intestinal microbial fermentation of indigestible foods, SCFAs in human gut are acetic, propionic and butyric acid. They are the main energy source of colonocytes, making them crucial to gastrointestinal health. SCFAs all possess varying degrees of water solubility, which distinguishes them from longer chain fatty acids that are immiscible.

<span class="mw-page-title-main">Free fatty acid receptor 3</span> Protein-coding gene in the species Homo sapiens

Free fatty acid receptor 3 protein is a G protein coupled receptor that in humans is encoded by the FFAR3 gene. GPRs reside on cell surfaces, bind specific signaling molecules, and thereby are activated to trigger certain functional responses in their parent cells. FFAR3 is a member of the free fatty acid receptor group of GPRs that includes FFAR1, FFAR2, and FFAR4. All of these FFARs are activated by fatty acids. FFAR3 and FFAR2 are activated by certain short-chain fatty acids (SC-FAs), i.e., fatty acids consisting of 2 to 6 carbon atoms whereas FFFAR1 and FFAR4 are activated by certain fatty acids that are 6 to more than 21 carbon atoms long. Hydroxycarboxylic acid receptor 2 is also activated by a SC-FA that activate FFAR3, i.e., butyric acid.

<span class="mw-page-title-main">Free fatty acid receptor 2</span> Protein-coding gene in the species Homo sapiens

Free fatty acid receptor 2 (FFAR2), also known as G-protein coupled receptor 43 (GPR43), is a rhodopsin-like G-protein coupled receptor (GPCR) encoded by the FFAR2 gene. In humans, the FFAR2 gene is located on the long arm of chromosome 19 at position 13.12 (19q13.12).

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

Propionibacterium freudenreichii is a gram-positive, non-motile bacterium that plays an important role in the creation of Emmental cheese, and to some extent, Jarlsberg cheese, Leerdammer and Maasdam cheese. Its concentration in Swiss-type cheeses is higher than in any other cheese. Propionibacteria are commonly found in milk and dairy products, though they have also been extracted from soil. P. freudenreichii has a circular chromosome about 2.5 Mb long. When Emmental cheese is being produced, P. freudenreichii ferments lactate to form acetate, propionate, and carbon dioxide

(3 C3H6O3 → 2 C2H5CO2 + C2H3O2 + CO2).
<span class="mw-page-title-main">Eyes (cheese)</span> Round holes in cheese

Eyes are the round holes that are a characteristic feature of Swiss-type cheese and some Dutch-type cheeses. The eyes are bubbles of carbon dioxide gas. The gas is produced by various species of bacteria in the cheese.

Odd-chain fatty acids are those fatty acids that contain an odd number of carbon atoms. In addition to being classified according to their saturation or unsaturation, fatty acids are also classified according to their odd or even numbers of constituent carbon atoms. With respect to natural abundance, most fatty acids are even chain, e.g. palmitic (C16) and stearic (C18). In terms of physical properties, odd and even fatty acids are similar, generally being colorless, soluble in alcohols, and often somewhat oily. The odd-chain fatty acids are biosynthesized and metabolized slightly differently from the even-chained relatives. In addition to the usual C12-C22 long chain fatty acids, some very long chain fatty acids (VLCFAs) are also known. Some of these VLCFAs are also of the odd-chain variety.

Symbiotic fermentation is a form of fermentation in which multiple organisms interact in symbiosis in order to produce the desired product. For example, a yeast may produce ethanol, which is then consumed by an acetic acid bacterium. Described early on as the fermentation of sugars following saccharification in a mixed fermentation process.

Propionate fermentation is a form of fermentation with propionic acid as one of the products. This process is done through the fermentation pathway of bacteria. It is used in a variety of industrial, food-making, and medical applications. Growing interest in the petroleum and chemical industries has led consideration for bioplastic and other chemical applications. All of this has a significant environmental and economic impact.

References

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  10. ↑ Johann Gottlieb (1844) "Ueber die Einwirkung von schmelzendem Kalihydrat auf Rohrzucker, Gummi, Stärkmehl und Mannit" (On the effect of molten potassium hydroxide on raw sugar, rubber, starch powder, and mannitol), Annalen der Chemie und Pharmacie, 52 : 121–130. After combining raw sugar with an excess of potassium hydroxide and distilling the result, Gottlieb obtained a product that he called "Metacetonsäure" (meta-acetone acid) on p. 122: "Das Destillat ist stark sauer und enthält Ameisensäure, Essigsäure und eine neue Säure, welche ich, aus unten anzuführenden Gründen, Metacetonsäure nenne." (The distillate is strongly acidic and contains formic acid, acetic acid, and a new acid, which for reasons to be presented below I call "meta-acetone acid".)
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  18. ↑ Alonso, Saúl; Rendueles, Manuel; Díaz, Mario (2015). "A novel approach to monitor stress-induced physiological responses in immobilized microorganisms". Applied Microbiology and Biotechnology. 99 (8): 3573–3583. doi:10.1007/s00253-015-6517-1. PMID   25776062. S2CID   860853.
  19. ↑ Belgrano, Fabricio dos Santos; Diegel, Olaf; Pereira, Nei; Hatti-Kaul, Rajni (2018). "Cell immobilization on 3D-printed matrices: A model study on propionic acid fermentation". Bioresource Technology. 249: 777–782. Bibcode:2018BiTec.249..777B. doi:10.1016/j.biortech.2017.10.087. PMID   29136932.
  20. ↑ Dishisha, Tarek; Alvarez, Maria Teresa; Hatti-Kaul, Rajni (2012). "Batch- and continuous propionic acid production from glycerol using free and immobilized cells of Propionibacterium acidipropionici" (PDF). Bioresource Technology. 118: 553–562. Bibcode:2012BiTec.118..553D. doi:10.1016/j.biortech.2012.05.079. PMID   22728152. S2CID   29658955.
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