pentaerythritol

C5H12O4

115-77-5

Applications:

1. Mainly used in the paint industry, can be used to manufacture alkyd resin paint, can make the paint film hardness, gloss and durability can be improved.

2. Used as the raw material of rosin ester for color paints, varnishes, printing inks, etc. It can also be used to make dry oil, anionic paints and aviation lubricants.

3. The fatty acid esters of pentaerythritol are efficient lubricants and PVC plasticizers, and its epoxy derivatives are raw materials for the production of non-ionized surfactants.

Names and Identifiers

Name	Pentaerythritol
Synonyms	THME PETP PE 200 Maxinutril herculesp6 Monopentek Metab-Auxil Hercules P 6 Pentaerythritol Pentaertyhritol Penta Erythritol Monopentaerythritol methanetetramethylol Tetramethylolmethane Methane tetramethylol Tetrakis(hydroxymethyl)methane Methane, tetrakis(hydroxymethyl)-, 2,2-bis(hydroxymethyl)-1,3-Propanediol 2,2-bis(hydroxymethyl)propane-1,3-diol
CAS	115-77-5
EINECS	204-104-9
InChI	InChI=1/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2
InChIKey	WXZMFSXDPGVJKK-UHFFFAOYSA-N

​Physico-chemical Properties

Molecular Formula	C5H12O4
Molar Mass	136.15
Density	1.396
Melting Point	253-258 °C (lit.)
Boling Point	276 °C/30 mmHg (lit.)
Flash Point	240 °C
Water Solubility	1 g/18 mL (15 ºC)
Solubility	H2O: 0.1g/mL, clear, colorless
Vapor Presure	<1 mm Hg ( 20 °C)
Appearance	Crystals
Color	White
Exposure Limit	ACGIH: TWA 10 mg/m3OSHA: TWA 15 mg/m3; TWA 5 mg/m3NIOSH: TWA 10 mg/m3; TWA 5 mg/m3
Merck	14,7111
BRN	1679274
pKa	13.55±0.10(Predicted)
PH	3.5-4.5 (100g/l, H2O, 35℃)
Storage Condition	Store below +30°C.
Stability	Stable. Incompatible with strong acids, strong oxidizing agents, acid chlorides, acid anhydrides. Combustible.
Sensitive	Hygroscopic
Refractive Index	1.548
Physical and Chemical Properties	Character white powder crystal. Melting Point: 261~262 ℃ Boiling Point: 276 ℃ relative density: 1.395g/cm3 refractive index: 1.548 when the solubility is 15 ℃, 1g is dissolved in 18ml of water. Soluble in ethanol, glycerol, ethylene glycol, formamide. Insoluble in acetone, benzene, carbon tetrachloride, ether and petroleum ether.
Use	Used in the coating industry, can also be used to prepare Aviation Lubricants, explosives, plasticizers, stabilizers

Risk and Safety

Risk Codes	33 – Danger of cumulative effects
Safety Description	24/25 – Avoid contact with skin and eyes.
WGK Germany	1
RTECS	RZ2490000
TSCA	Yes
HS Code	29054200
Toxicity	LD50 orally in Rabbit: > 5110 mg/kg LD50 dermal Rabbit > 10000 mg/kg

Upstream Downstream Industry

Raw Materials	Formaldehyde Formic acid Sodium hydroxide Acetaldehyde
Downstream Products	Pentaerythrityl tetrastearate 9-Octadecenoic acid (Z)-, ester with 2,2-bis(hydroxymethyl)-1,3-propanediol Monostearin Sodium formate

Nature

white powder crystals. Density 1.395G/cm3. The melting point was 261-262 °c. Boiling Point (4kPa) 276. Refractive index 548. Ignition point <370 °c. Heat of vaporization <92kJ/mol, exothermic heat 13L skj/mol. It is easy to be esterified with common organic acids, and has no reaction with dilute caustic soda solution. lg was dissolved in 18rnL water at 15 °c. Soluble in ethanol, glycerol, ethylene glycol, formamide. Insoluble in acetone, benzene, carbon tetrachloride, ether and petroleum ether.

Preparation Method

with formaldehyde and acetaldehyde as raw materials, generally in 40~70 deg C in the presence of alkaline catalyst condensation, and then with acetic acid neutralized excess alkali, the excess of formaldehyde was distilled off and then evaporated under vacuum, cooled and filtered to obtain a finished product.M is an alkali metal or alkaline earth metal. If NaOH is used as a condensing agent, neutralization and filtration are sufficient, which is referred to as sodium method. Such as the use of calcium hydroxide as a condensing agent, need to sulfuric acid or oxalic acid neutralization, so as to become calcium salt precipitation filtration in addition to calcium, referred to as calcium method. The filtrate was concentrated under reduced pressure, crystallized, centrifuged and dried to give a finished product.

Use

commonly used in the coating industry, is the raw material of Alkyd Coatings, can make the coating film hardness, gloss and durability can be improved. It is also used as the raw material of modified rosin alcohol required for varnish, paint and printing ink, and can be used for the preparation of flame retardant coatings, drying oil and aviation lubricating oil. Pentaerythritol tetranitrate made from pentaerythritol is a highly explosive explosive. Pentaerythritol fatty acid ester can be used as plasticizer and stabilizer for polyvinyl chloride resin. In addition, it can also be used in the manufacture of medicines, surfactants, adhesives, pesticides and lubricating oils.

Safety

basically non-toxic. In the human body does not produce metabolic changes, but taking high doses, there will be high blood sugar or Diarrhea phenomenon. Skin and eye contact with a saturated solution of pentaerythritol also does not occur irritation or inflammation.the use of plastic bag jacket polypropylene woven bag or bag packaging, each 25kg. Pentaerythritol dust in the air concentration of more than 30g/m3, can form an explosive mixture with air, when more than 400 ℃ explosion occurs. Therefore, it should be stored in a cool, dry, ventilated place, moisture, fire. According to the general provisions of the storage and transportation of chemicals.

Reference Information

LogP	-1.7 at 22℃
main uses and functions	pentaerythritol, as a quaternary alcohol, is easy to esterify to form acids and esters, so it is mostly used as raw materials for alkyd resin coatings, mainly used as architectural coatings and automobile primers. In industry, pentaerythritol and concentrated nitric acid are esterified at 5~15 ℃ to obtain pentaerythritol tetranitrate (also known as PETN, Taien). It is a high-performance high explosive with greater explosive power than TNT. It is mostly used as an explosive, or mixed with TNT. Used extensively in the Second World War. Taien also has the effect of relaxing blood vessels. It is a long-acting vasodilator that can treat angina pectoris. The reaction of pentaerythritol and rosin acid can produce pentaerythritol rosin ester. It can be mixed with dry oil to obtain a coating with good hardness, water resistance and weather resistance. It is used for varnish, floor ink, etc. An alkyd resin coating can be made by esterification polycondensation of pentaerythritol or glycerol with phthalic anhydride and fatty acids. The use of different kinds and different amounts of fatty acids can improve the properties of alkyd resin, making it a coating suitable for various needs. It is widely used as a coating for metal and wood surfaces. It is a commonly used industrial paint and architectural paint for bridges, railways, derricks, housing construction, etc. Due to the low price of alkyd resin, easy availability of raw materials, easy modification, strong adaptability and good comprehensiveness, it has developed rapidly since it entered industrial production in 1927 and has become the backbone of the coating industry. Pentaerythritol is commonly used in the coating industry. It is the raw material of alkyd coatings. It uses four hydroxyl groups to produce highly cross-linked coatings. This coating has excellent hardness and color, and can improve the hardness, gloss and durability of the coating film. It is also used as a raw material for varnish, paint and ink to produce rosin ester, and can be used as flame retardant, dry oil and aviation lubricating oil. Pentaerythritol fatty acid esters are polyvinyl chloride plasticizers and stabilizers, and are also used in the manufacture of medicines, pesticides, and lubricants. pentaerythritol acrylate produced by pentaerythritol and acrylic acid has quick-drying properties and is widely used in radiation-curing coatings and quick-drying printing inks to produce water-soluble alkyd resins. Its polymers can be used as adhesives. C6 ~ C10 fatty acid esters of pentaerythritol are mainly used as advanced lubricants for steam turbines, automobile engines, etc. The ester synthesized by this product and C10 ~ C12 fatty acid can be used as a plasticizer for plastics, with low volatility and aging resistance; it reacts with epoxy compounds, and its products can be used as surfactants, widely used in detergents, cosmetics and perfume raw materials; this product is also used as raw materials for explosives, medicines, pesticides, etc.; organic intermediates, etc.
chemical additive	pentaerythritol can be used as a stabilizing additive for polyvinyl chloride. it has a synergistic effect when used with zinc salt stabilizer, and can replace allyl chloride to stabilize polyvinyl chloride. The general dosage is 0.5 parts. However, this product has little compatibility with resin, is easy to spray frost, and is easily soluble in water and easy to sublimate. During the processing, the sublimation is deposited on the processing equipment, which hinders the processing.
harmful effects and toxic symptoms	pentaerythritol is low in toxicity. rats are exposed to oral toxicity at a dose of 40 g/kg body weight, and no obvious toxic symptoms are found. The U.S. Food and Drug Administration licenses it for food packaging materials (FDA121.2566) with a maximum dosage of 0.4%. It has been reported that ingestion studies have shown that 85% pentaerythritol is excreted from the urine within 30 hours after oral administration. Generally speaking, there is no significant effect on health according to the usual exposure route or even at abnormal concentration.
Uses	Mainly used in the production of alkyd resins, and also used as raw materials for manufacturing inks, lubricants, plasticizers, surfactants, explosives and drugs Used as resins and synthetic fiber antistatic agents, solvent conditioners, fiber oils, etc. Pentaerythritol is mainly used in the coating industry and is the raw material for alkyd resin coatings, it can improve the hardness, gloss and durability of the coating film. It is also used as the raw material of rosin grease required for varnish, color paint and printing ink, and can be used to make smoldering coatings, dry oil and air lubricating oil. The tetranitrate of pentaerythritol is a high explosive (ie Tai’an); its fatty acid ester is a high-efficiency lubricant and polyvinyl chloride plasticizer; its epoxy derivative is the production of non-free surfactants The raw material of pentaerythritol is easy to form authoritative complexes with metals. It is also used as a hard water softener in detergent formulations. In addition, it should also be produced in medicines and pesticides. used in the coating industry, can also prepare aviation lubricating oil, explosives, plasticizer, stabilizer used as gas chromatography reagent and insecticide gas chromatography stationary liquid, separation and analysis of low boiling point oxygen compounds, amine compounds, nitrogen or oxygen heterocyclic compounds. Organic synthesis, polyol preparation, resin synthesis. gas chromatography stationary solution [the maximum service temperature is 150 ℃, the solvent is chloroform butanol (1:1)], separation and analysis of low boiling point oxygenates, amine compounds, nitrogen or oxygen heterocyclic compounds. Organic synthesis, polyol preparation, resin synthesis.
production method	formaldehyde and acetaldehyde are used as raw materials and reacted in the presence of alkaline condensing agent. When sodium hydroxide is used as the condensing agent, it is called the sodium method. The molar ratio of raw materials is acetaldehyde: formaldehyde: alkali = 1.5:6:1.1-1.3. Add sodium hydroxide solution into 37% formaldehyde solution, add acetaldehyde under stirring, and react at 25-32 ℃ for 6-7h. After neutralization and filtration to obtain pentaerythritol. Raw material consumption quota: formaldehyde (37%)2880kg/t, acetaldehyde 350kg/t. When calcium hydroxide is used as a condensing agent, it is called calcium method. The molar ratio of raw materials is acetaldehyde: formaldehyde: lime = 1:4.7:0.7-0.8. Add formaldehyde solution, 20% acetaldehyde solution and 25% lime milk to the reaction pot and react below 60 ℃. The color of the condensation solution changes from gray to green. Gradually cool down to 45 ℃ and put it in an acidizing pot. The condensation solution was acidified with 60-70% sulfuric acid to a pH of 2-2.5, and then the calcium sulfate was reduced with a filter press. The filtrate was removed from the residual calcium ions by ion-effect exchange column, and concentrated under reduced pressure in drought. The gas phase temperature was maintained below 70 ℃ and the vacuum degree was maintained at 77.3kPa. At the beginning of crystallization, the concentrated solution is put into the crystallization tank, stirred to cool the crystallization, centrifuged and separated, washed with water to pH 3, and the wet finished product is dried by air flow to obtain the finished product. The consumption of calcium method is high, and there are many problems with three wastes. Raw material consumption quota: formaldehyde (36.5%)4700kg/t, acetaldehyde 550kg/t.
category	flammable liquid
toxicity classification	poisoning
acute toxicity	oral-rat LD50: 12600 mg/kg; Oral-mouse LD50: 4097 mg/kg
stimulation data	skin-rabbit 500 mg/24 hours mild; Eye-rabbit 126 mg mild
flammability hazard characteristics	flammable; combustion produces stimulating smoke
storage and transportation characteristics	warehouse ventilation and low temperature drying
fire extinguishing agent	dry powder, foam, sand, water
occupational standard	TLV-TWA 10 mg/m3
spontaneous combustion temperature	490°C

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