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PENTAERYTHRITOL
CAS: 115-77-5
European Community (EC) Number: 204-104-9
Molecular Formula: C5H12O4
Molecular Weight: 136.15
IUPAC Name: 2,2-bis(hydroxymethyl)propane-1,3-diol
Pentaerythritol is an organic compound with the formula C(CH2OH)4.
Classified as a polyol, Pentaerythritol is a white solid.
Pentaerythritol is a building block for the synthesis and production of explosives, plastics, paints, appliances, cosmetics, and many other commercial products.
The word pentaerythritol is a blend of penta- in reference to its 5 carbon atoms and erythritol, which also possesses 4 alcohol groups.
Pentaerythritol was first reported in 1891 by German chemist Bernhard Tollens and his student P. Wigand.
Pentaerythritol may be prepared via a base-catalyzed multiple-addition reaction between acetaldehyde and 3 equivalents of formaldehyde to give pentaerythrose (CAS: 3818-32-4), followed by a Cannizzaro reaction with a fourth equivalent of formaldehyde to give the final product.
Pentaerythritol is an odorless white solid. Sinks and mixes slowly with water.
Pentaerythritol is a tetrol that is neopentane in which one of the methyl hydrogens of all four methyl groups are replaced by hydroxy groups.
Pentaerythritol is a chemical intermediate used in the production of explosives, plastics, paints, appliances, and cosmetics.
Pentaerythritol has a role as a flame retardant and a laxative.
Pentaerythritol is a primary alcohol and a tetrol.
Pentaerythritol derives from a hydride of a neopentane.
Pentaerythritol is a simple five-carbon tetraol used in the fabrication of resins, alkylated resins, varnishes, PVC stabilizers, tall oil esters, and olefin antioxidants.
Pentaerythritol is also known under names Hercules P6, monopentaerythritol, tetramethylolmethane, THME, PETP, pentaerythrite, Pentek, etc.
Pentaerythritol is an interesting compound that allows for the attachment of four (similar or different) groups and, hence, the construction of highly branched structures.
Accordingly, Pentaerythritol has received considerable interest as an orthogonally protected handle useful for the generation of combinatorial libraries and as a building block that fits well in the general structure of oligonucleotides and peptides, providing additional functionalities.
Pentaerythritol (Penta) is a white crystalline polyhydric alcohol containing four primary hydroxyl groups.
Applications are building block in Alkyd resins, radiation curing monomers, polyurethanes, rosin esters and synthetic lubricants.
Mono Pentaerythritol (also known as PETP; tetramethylolmethane, and THME) is a polyhydric alcohol that contains four primary hydroxyl groups.
Pentaerythritol has the formula C5H12O4 and is a white, odourless, crystalline solid however it can also be a white, crystalline free-flowing powder.
Pentaerythritol is moderately soluble in cold water, is freely soluble in hot water, and is slightly soluble in alcohol.
Pentaerythritols primary role in industry is as a chemical intermediate.
There are many grades of Pentaerythritol available commercially but Mono Pentaerythritol has the largest market share as it accounts for approximately 85% of worldwide sales.
Pentaerythritol is composed of 98% pure Mono Pentaerythritol.
Mono Pentaerythritol is synthesized from the aldol condensation of formaldehyde and acetaldehyde.
The aldehyde that is produced then undergoes a cross- Cannizzaro reaction where one molecule of pentaerythritose is reduced to pentaerythritol.
The raw pentaerythritol is then separated out, dissolved, and is then subjected to high temperature acid hydrolysis.
It is then purified in an active carbon bed, after which it is concentrated and crystallised.
The main commercial and industrial role for Mono Pentaerythritol is as a chemical intermediate as it is a basic material for polymer production.
Pentaerythritol is mainly employed in the manufacture of alkyd resins and paints, where it enhances the drying speed, hardness, and the water resistance of these paints.
The second largest market for mono pentaerythritol is in the production of neopolyol esters for synthetic lubricants.
Pentaerythritol ensures both the hydrolytic resistance, and the viscosity control, of these lubricants.
Pentaerythritol is also employed in the preparation of polyvinyl chloride stabilisers, plasticisers, antioxidants, adhesives and sealants, varnishes and inks.
Pentaerythritol is also used to make radiation-curing monomers, and rosin esters.
Pentaerythritol (Penta-Mono grade) is a white crystalline powder.
Pentaerythritol is a synthetic polyhydric alcohol containing four primary hydroxyl groups (tetra functional compound).
Pentaerythritol provides the outstanding properties due to the nature of compact structure and high density of hydroxyl groups.
Pentaerythritol is used in production of Alkyd resin, Pentaerythritol tetranitrate (PETN – an explosive), Pentrinitrol (Petrin), Normosterol (PAG), Pentaerythritol tetraacrylate (polymer cross-linking agent).
Major application for Penta is branching of monomer for alkyd resin that provides the excellent performance related to drying speed, viscosity, water resistance properties of the paints.
Pentaerythritol, commonly known in the Chemical Industry simply as “Penta,” is a white, odorless, crystalline powder.
Pentaerythritol is soluble in water, slightly soluble in alcohol and insoluble in most hydrocarbons.
Higher homologues of Penta, including Di- and Tripentaerythritol are also produced in the manufacturing process.
Dipentaerythritol is an off-white powder that is less soluble than Pentaerythritol.
Pentaerythritol is manufactured from formaldehyde and acetaldehyde in the presence of an alkaline catalyst, such as sodium or calcium hydroxide.
Pentaerythrose is initially formed from three sequential aldol reactions and then subsequently reduced in a crossed Cannizarro reaction with formaldehyde to produce Pentaerythritol.
Pentaerythritol is a five-carbon, with four reactive alcohol groups.
Pentaerythritol (2,2-bis (hydroxymethyl) propane-1,3-diol) as white crystalline odorless solid has been synthesized in 1891.
Pentaerythritol is multifaceted species in many compounds, which are wildly utilized in medicine and industry.
Also, multicomponent reactions (MCRs) play a crucial role in organic and medicinal chemistry.
Hence, in these reactions, pentaerythritol is a versatile substrate for the synthesis of many polyfunctionalized products, because of the presence of the neopentane core and one hydroxyl group in each of the four terminal carbons.
A process for the preparation of pentaerythritol, comprising reacting formaldehyde, acetaldehyde and sodium hydroxide and acidification with formic acid.
These steps take place in a reactor with supplies of formaldehyde, sodium hydroxide, acetaldehyde and formic acid and at the end the solution formed is evacuated to a buffer tank of larger capacity than the reactor.
In the reactor new reactions and acidifications are successively reinitiated by new supplies.
In the first place a formaldehyde solution is added, followed by simultaneous but separate additions of sodium hydroxide solution and acetaldehyde, forming a reaction mixture in such a way that the flowrates of the solutions vary with the time and that the temperature at which the reactions are conducted also varies with the time.
The outflow from the buffer tank is constant and continuous.
Pentaerythritol (PE) is primarily used to produce resins and lubricants that are used in refrigeration, high quality surface coatings, explosives and other applications.
Our formaldehyde offering for PE production includes:
Pentaerythritol is often used as a thickening agent in food.
Pentaerythritol can be used as a substitute for sugar in foods because it is about two-thirds as sweet as sugar.
Pentaerythritol is also used as a thickening agent in paints, in the production of polyester fibers, and as a component in the production of polyurethane foams.
Pentaerythritol is a type of polyhydric alcohol.
Pentaerythritol is odorless and free flowing white crystalline powder, which is non-hygroscopic and stable in storage.
Pentaerythritol is used primarily in the production of alkyd resins as well as a variety of other products such as rosin esters, oil-modified urethane resins, modified drying oils, synthetic lubricants, plasticizers, intumescent paints, plastics and stabilizers for plastics
In addition, pentaerythritol polymers function as cryoprotectants.
Protein crystals grown in high concentrations of these precipitants can be frozen directly from the crystallization drop. The successful application of pentaerythritol polymers to yield protein crystals was first described by Gulick et al. .
Furthermore, this class of precipitants has been used for membrane crystallization: The X-ray structure of cbb3 Cytochrome Oxidase was published in Science in 2010.
Crystals of this proton pumping membrane protein were successfully grown using pentaerythritol ethoxylate as precipitation agent.
Uses
Pentaerythritol is a versatile building block for the preparation of many polyfunctionalized compounds.
Derivatives of pentaerythritol are components of alkyd resins, varnishes, polyvinyl chloride stabilizers, tall oil esters, antioxidants (e.g. Anox 20).
Pentaerythritol can be found in transformer oil, plastics, paints, cosmetics, and many other applications.
Polyester derivatives
Pentaerythritol is a precursor to esters of the type C(CH2OX)4.
One such derivative is pentaerythritol tetranitrate (PETN), a vasodilator and explosive.
The trinitrate derivative is called pentrinitrol (Petrin).
The tetraacetate is called normosterol (PAG).
The polymer cross-linking agent pentaerythritol tetraacrylate.
Fire retardants
Pentaerythritol is used as a fire retardant, such as in plastics.
Pentaerythritol produces a thick carbon barrier upon heating, protecting the surface substrate.
Pentaerythritol is one of the most common main active components in intumescent paints and coatings.
Pentaerythritol acts as a carbon donor and together with an acid donor, most commonly ammonium polyphosphate (APP), and a blowing agent, most commonly melamine.
As a raw-material for alkyd resins; Pentaerythritol used in the manufacture of high quality oil based surface coatings.
As a raw-material for rosin and tall oil esters, Pentaerythritol used in the manufacture of high quality oil based varnishes.
As a raw-material to C5 - C11 mono carboxylic acid esters, components for synthetic aircraft gas turbine lubricants.
Pentaerythritol is a raw-material for plasticizers, heat stabilizers, intumescents used in flame retardent paints, chlorinated polyether resins and multifunctional acrylatemonomers.
APPLICATIONS
-Alkyd-based coatings
-Synthetic lubricants
-Hot-melt adhesives
-Rosin esters
-Antioxidants
-Explosives
-Radiation curing monomers
-Pigment treatment
-Polyurethanes
-PVC stabilizers
-Lubricants
-Plasticizers
-Synthetic drying oil
Alkyd Resins
Alkyds are used in paints and in moulds for casting.
They are the dominant resin or "binder" in most commercial "oil-based" coatings.
Approximately 200,000 tons of alkyd resins are produced each year.
Rosin and Tall Oil Esters
Rosin is an ingredient in printing inks, photocopying and laser printing paper, varnishes, adhesives (glues), soap, paper sizing, soda, soldering fluxes, and sealing wax.
The tall oil rosin finds use as a component of adhesives, rubbers, and inks, and as an emulsifier.
Special Varnishes
Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials.
Varnish is traditionally a combination of a drying oil, a resin, and a thinner or solvent.
Plasticizers
Plasticizers or dispersants are additives that increase the plasticity or fluidity of the material to which they are added; these include plastics, cement, concrete, wallboard, and clay.
Insecticides
An insecticide is a pesticide used against insects.
They include ovicides and larvicides used against the eggs and larvae of insects respectively.
Insecticides are used in agriculture, medicine, industry and the household.
The use of insecticides is believed to be one of the major factors behind the increase in agricultural productivity in the 20th century
Synthetic Lubricants
Synthetic lubricants can be manufactured using chemically modified petroleum components rather than whole crude oil, but can also be synthesized from other raw materials.
Synthetic lubricant is used as a substitute for lubricant refined from petroleum when operating in extremes of temperature, because it generally provides superior mechanical and chemical properties than those found in traditional mineral oils.
Aircraft turbines, for example, require the use of synthetic oils, whereas aircraft piston engines don't.
Explosives
Explosive is a substance that contains a great amount of stored energy that can produce an explosion, a sudden expansion of the material after initiation, usually accompanied by the production of light, heat, sound, and pressure.
Antioxidants
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules.
Oxidation is a chemical reaction that transfers electrons from a substance to an oxidizing agent.
Oxidation reactions can produce free radicals.
In turn, these radicals can start chain reactions that damage cells.
Antioxidants terminate these chain reactions by removing free radical intermediates, and inhibit other oxidation reactions.
Ink
Ink can be a complex medium, composed of solvents, pigments, dyes, resins, lubricants, solubilizers, surfactants, particulate matter, fluorescers, and other materials.
Ink is a liquid that contains pigments and/or dyes and is used to colour a surface to produce an image, text, or design.
Ink is used for drawing and/or writing with a pen, brush, or quill.
Thicker inks, in paste form, are used extensively in letterpress and lithographic printing.
PVC Stabilizers
Polyvinyl chloride is the third most widely produced plastic, after polyethylene and polypropylene.
PVC is widely used in construction because it is cheap, durable, and easy to assemble.
The stabilizers are barium, calcium and zinc salts of dicarboxylic acid esters of Penta, such as the zinc salt of pentaerythritol di-phthalic acid ester or di-terephthalic acid ester.
The role is to solubilize the barium and zinc in the PVC so these salts can remove labile chloride groups on the PVC resin.
Paint Swelling Agents
Penta and its esters are used as ingredients in paint stripping formulations that also contains solvents, wetting agents, and swelling agents.
The swelling agents help to separate the paint from substrate.
The polyol portion of the Penta ester can also act as a redistribution compound via transesterification.
Radiation Curing Monomers
End-capping of isocyanate terminated polyurethane prepolymer with a monofunctional acrylate like pentaerythritol triacrylate renders the polyurethane radiation curable.
Other UV-curable penta-based acrylates are pentaerythritol tetraacrylate and ethoxylated pentaerythritol tetraacrylate.
Urethane acrylates have very good flexibility and very good adhesion.
Acrylatyed dipentaerythritol exhibits increased crosslinking and high reactivity and offers very good hardness, scratch resistance and chemical resistance.
PROPERTIES
-White
-Crystalline powder
-Odorless
-Non-hazardous
-Solid compound
-Water-soluble
-Slightly soluble in alcohol
-Insoluble in most hydrocarbons
-Also called monopentaerythritol
SYNONYMS:
PENTAERYTHRITOL
115-77-5
2,2-bis(hydroxymethyl)propane-1,3-diol
Pentek
Tetramethylolmethane
Monopentaerythritol
Pentaerythrite
Auxinutril
Maxinutril
Monopentek
Penetek
Metab-Auxil
Hercules P6
Tetrahydroxymethylmethane
Methane tetramethylol
2,2-Bis(hydroxymethyl)-1,3-propanediol
Tetrakis(hydroxymethyl)methane
1,3-Propanediol, 2,2-bis(hydroxymethyl)-
tetra(hydroxymethyl)methane
THME
PE 200
Auxitrans
1,1,1-Tris(hydroxymethyl)ethanol
NSC 8100
UNII-SU420W1S6N
MFCD00004692
Pentaerythritol, 98%
SU420W1S6N
DSSTox_CID_6943
DSSTox_RID_78264
DSSTox_GSID_26943
1,3-Propanediol, 2,2-bis(hydroxymethyl)-, homopolymer
pentaerithrityl
Pentaerythrital
54640-10-7
CAS-115-77-5
Black cohosh extract
Charmor PM 15
CCRIS 2306
HSDB 872
EINECS 204-104-9
BRN 1679274
Auxenutril
Pentaertyhritol
Hydrafuca
AI3-19571
Hercules Mono-PE
Auxitrans (TN)
mono pentaerythritol
3SY
Pentaerythritol, CP
tetramethylol methane
334974-06-0
Pentaerythritol, 99%
MONOPENTAERYTHRITO
Pentaerythritol-[13C]
EC 204-104-9
Pentaerythritol, sodium salt
ACMC-1C8V3
SCHEMBL15049
WLN: Q1X1Q1Q1Q
4-01-00-02812 (Beilstein Handbook Reference)
C(CH2OH)4
1, 2,2-bis(hydroxymethyl)-
CHEMBL3186112
DTXSID2026943
1,2-Diacylglycerol-LD-PE-pool
NSC8100
CHEBI:134760
DAMIANA Powder & Powder Extract
ZINC391843
Methane, tetrakis(hydroxymethyl)-,
AMY40485
NSC-8100
Pentaerythritol, calcium, zinc salt
Tox21_201921
Tox21_303573
ANW-16903
SBB060192
STL483077
AKOS009166690
DB13526
MCULE-7635228253
2,2-bis-hydroxymethyl-propane-1,3-diol
NCGC00249136-01
NCGC00257496-01
NCGC00259470-01
BP-13392
2,2-bis(hydroxymethyl)-propane-1,3-diol
FT-0652275
FT-0673583
P0039
ST51046424
BLACK COHOSH ROOT Powder & Powder Extract
D08331
55474-EP2269996A1
55474-EP2270101A1
55474-EP2284165A1
55474-EP2292597A1
55474-EP2295399A2
55474-EP2295438A1
55474-EP2301919A1
55474-EP2301924A1
55474-EP2302015A1
55474-EP2305808A1
55474-EP2308857A1
55474-EP2308865A1
55474-EP2371805A1
55474-EP2372017A1
55474-EP2374895A1
A803483
Q421828
Q-201541
Q-201892
F0001-0283
