115-77-5 Usage
Uses
Used in Coatings and Surface Coating Compositions:
Pentaerythritol is used as a source of alkyd resin coating, which enhances the hardness, gloss, and durability of the coating film. It is an essential raw material for varnish, color paint, and printing ink of pine resin, as well as for smoldering coatings, drying oil, and lubricating oil.
Used in Plastics and Lubricants:
The fatty acid ester of pentaerythritol serves as an efficient lubricant and plasticizer for PVC.
Used in Explosives:
Pentaerythritol tetranitrate (PETN) is a high explosive derived from pentaerythritol.
Used in Detergents and Water Softeners:
Pentaerythritol easily forms complexes with metals, making it useful as a hard water softener in detergent formulations.
Used in Medicine and Pesticides:
Pentaerythritol is also utilized in the production of pharmaceuticals and pesticides.
Used in Cosmetics:
Pentaerythritol, particularly in its rosinate form, is used as a skin conditioning agent in lotions and creams, as well as to increase the viscosity of cosmetic formulations.
Used in Gas Chromatography:
As a gas chromatographic stationary liquid, pentaerythritol is used for the separation and analysis of low boiling point oxygen-containing compounds, amine compounds, and nitrogen or oxygen heterocyclic compounds.
Used in Organic Synthesis and Resin Production:
Pentaerythritol is a key component in the synthesis of various dendrimers, star-shaped polymers, and flame-retardant epoxy resins and polymer composites.
Used in the Synthesis of Pentaerythritol Tetranitrate:
Pentaerythritol is a compound commonly used in the manufacture of pentaerythritol tetranitrate, an explosive material.
Used in the Synthesis of Alkyd Resins:
Pentaerythritol is a versatile starting material for synthesizing alkyd resins, which are used in surface-coating compositions.
Used in the Synthesis of Pentaerythritol Triacrylate and Protective Coatings:
Pentaerythritol is also used in the production of pentaerythritol triacrylate, which is utilized in protective coatings.
Used in the Synthesis of Insecticides and Pharmaceuticals:
Pentaerythritol is employed as a starting material for the synthesis of various insecticides and pharmaceuticals.
Physical and chemical properties
Pentaerythritol is also called 2, 2-double (hydroxymethyl)-1, 3-propanediol, four hydroxymethyl methane, MetabAuxil, Penetek. White crystal powder. It was first found in 1882 by Tollens, and is colorless tetragonal crystal double tetrahedral crystal precipitated from dilute hydrochloric acid. The relative molecular mass is 136.15. Relative density is 1.399. Melting point is 262 oC (industrial products containing 10%~15% Dipentaerythritol, melting point is 180~225 oC). The boiling point is 276 oC (4.00 x 103 pa). The refractive index is 1.54~1.56. Can sublimate. Slowly soluble in cold water, soluble in hot water, insoluble in carbon tetrachloride, ethyl ether, benzene, petroleum ether, ethanol, acetone, solubility at 25 oC (g/100 g) in water, methanol, ethanol, butylamine, dimethyl sulfoxide, ethanolamine are 0.75, 7.23, 0.33, 16, 16.5 4.5, respectively. 1 g of dipentaerythritol can soluble in 18 ml of water at 15 oC. Pentaerythritol will polymerize when heated to above melting point, and generates a shrinkage second shrinkage e four season three pentaerythritol, etc. Stability in the air. The hydroxyl groups of Pentaerythritol can form complex with many kinds of metal; Can directly react with nitric acid trough nitration; Under the effect of catalyst, the hydroxy can be oxidized to acid; Can react with chlorine to generate the chloride; In acid medium, the product react with carbonyl compounds, generate cyclic acetal and ketal; Like other alcohols, can esterify with an acid or anhydride to generate four ester; The halides can dehalogenate to generate cyclic ether in the role of alkali. The addition reaction intermediate of 3-hydroxy aldehyde can react with formaldehyde through Cannizzaro reaction to generate season four amyl alcohol and formic acid. In 1938, it was first generated by United States with acetaldehyde and five times the amount of formaldehyde in the reaction of calcium hydroxide solution system. It is the only production method used in the industrial. Main purpose is to make explosives and synthetic resin (mainly used for various coatings).
The main purpose and effect
As quaternary alcohol, pentaerythritol is easily generated by esterification acid and ester, so most of the classes used in alkyd resin coatings raw materials, mainly used for architectural coatings and automotive primer. Pentaerythritol is used to esterification with nitric acid to generate pentaerythritol tetranitrate (also known as PETN) in 5~15 oC in industrial, which is a kind of high explosives and bigger than TNT explosive, most as a booster, or mix with TNT. A lot of PETN have been used in the second world war. PETN has the effect of diastolic blood vessels, is a long-term vasodilator and can treat angina pectoris. Pentaerythritol reaction with rosin acid can produce rosin pentaerythritol ester, which can be mixed with drying oil and is a kind of coating with better hardness, water resistance and weather resistance, can be used in ink of varnish, floor, etc. By esterification condensation pentaerythritol or glycerol with phthalic anhydride, fatty acid can make an alkyd resin coating. Use of different kinds and different amount of fatty acid can improve the properties of alkyd resin, making it a suitable coating of various kinds in need. It is widely used as a coating on the surface of the metal, wood, as a bridge, railway, derrick, building and other aspects of commonly used industrial paint and architectural paint. Because of the price is low, alkyd resin of reactants, easy modification, strong adaptability, good comprehensive, it has become the backbone of the coating industry since 1927.
Pentaerythritol is often used in coating industry, is of alkyd coating raw material for the production of highly cross linked coatin using four hydroxyls, the coating has good hardness and color, can improve the hardness, luster and durability of the coating film. Used as varnish, paint and ink production of rosin ester raw material, and can be used as flame retardants, drying oil, aviation lubricating oil. Pentaerythritol fatty acid ester is polyvinyl chloride (PVC), plasticizer and stabilizer is also used in medicine, pesticide, lube oil manufacture.
Pentaerythritol acrylic ester generated by Pentaerythritol and acrylic acid has a fast drying property, it is widely used in radiation-curing coatings and quick drying of printing ink, water soluble alkyd resin, the polymer can be used as adhesive. The C6~C10 fatty acid ester of Pentaerythritol are mainly used as advanced lubricant for steam turbine, automobile engine etc. The ester produced by this product with C10~C12 fatty acid, can be used as a plastic plasticizer, which has low volatility and high ageing resistance; Reaction with epoxy compound, and its product can be used as a surface active agent, widely used in detergent and cosmetics and perfume raw materials; This product is used as the material of explosives, medicine, pesticides, organic intermediates, etc.
The above information is edited by the lookchem of Duan Yalan.
Chemical additives
Pentaerythritol can be used as a stabilizing agent, and has synergistic effect with zinc salt stabilizers, can replace allyl chloride to stabilize PVC. General dosage is half serving. But the compatibility with the resin of this product is small, easy to bloom, and soluble in water, easy sublimation, easy deposit on processing equipment and interfere with the processing in the process of sublimation.
Harmful effects and symptoms of poisoning
Pentaerythritol has low toxicity, from rat infected through the mouth to the dose of 40 g/kg body weight, no obvious toxic symptoms. The US Food and Drug Administration permits it for food packaging materials (FDA121.2566), the highest dosage is 0.4%.
Someone reports and food studies showed that 85% of pentaerythritol were discharged from the urine after oral within 30 h. Generally speaking, according to the usual route of exposure even under abnormal use concentration, no significant effect to health.
Production method
It is produced using formaldehyde and acetaldehyde as raw materials, in the presence of alkaline condensation agent reaction. When using sodium hydroxide as condensing agent, it is called sodium method. The molar ratio of raw materials for acetaldehyde: formaldehyde: alkali is 1.5: 6: 1.1-1.3. Adding sodium hydroxide solution to 37% formaldehyde solution, join the acetaldehyde under stirring at 25-32 oC and react for 6 to 7 h. By the neutralization filter to obtain pentaerythritol. Raw material consumption quota: formaldehyde (37%) 2880 kg/t, acetaldehyde 350 kg/t. When using calcium hydroxide as a condensing agent, it is called calcium method. The molar ratio of raw materials for acetaldehyde: formaldehyde: lime is 1: 4.7: 0.7-0.8. Add the formaldehyde solution, 20% acetaldehyde solution and 25% lime milk to reaction pot, react at 60 oC, condensate until liquid color turned to blue from gray. Gradually cooled to 45 oC in the acidification of pan. Acidificate the condensed liquid with 60-70% of the sulfuric acid to the pH of 2-2.5, then use filter airland to calcium sulfate. Filtrate through ion exchange column to remove residual calcium ion, stress concentration, keep gas temperature under 70 oC, vacuum at 77.3 kPa. Began to crystallize, transfer concentrate in the crystallizer, mixing the cooling crystallization, centrifugal separation, washed with water to the pH of 3, drying by the airflow then obtain products. The consumption of Calcium method is high, and also has the problem of "three wastes". Raw material consumption quota: formaldehyde (36.5%) 4700 kg/t, acetaldehyde 550 kg/t.
Toxicity grading
Poisoning
Acute toxicity
Oral-LD50 in rats: 12600 mg/kg. Oral LD50 in mice: 4097 mg/kg.
Stimulus data
Skin-rabbit 500 mg/24 hours light; Eyes-rabbit 126 mg light.
Flammability hazard characteristics
Flammable. Combustion produces stimulation of smoke.
Storage Characteristics
Warehouse ventilation, dry at low temperature.
Extinguishing agent
Dry powder, foam, sandy soil, and water.
Occupational standards
The TLV-TWA 10 mg/cubic meter.
Air & Water Reactions
Water soluble.
Reactivity Profile
Pentaerythritol is an alcohol. Pentaerythritol is incompatible with the following: Organic acids, oxidizers [Note: Explosive compound is formed when a mixture of PE & thiophosphoryl chloride is heated.] .
Health Hazard
Non-toxic; no symptoms likely
Flammability and Explosibility
Notclassified
Safety Profile
Mildly toxic by ingestion. A nuisance dust. Flammable from heat or flame or oxidizers. Wxtures with thiophosphoryl chloride react when heated to form a product that ignites and then explodes on contact with air. Used in coatings, stabdizers, explosives, P.E.T.N resins, drugs, insecticides, and lubricants When heated to decomposition it emits acrid smoke and irritating fumes
Potential Exposure
Pentaerythritol is used in coatings and
stabilizers; in the formation of alkyd resins and varnishes.
It is used as an intermediate in the manufacture of plasticizers,
explosives (PETN),and pharmaceuticals.
Shipping
UN1987 Alcohols, n.o.s., Hazard Class: 3;
Labels: 3-Flammable liquid.
Purification Methods
Reflux pentaerythritol with an equal volume of MeOH, then cool, and the precipitate is collected and dried at 90o. It can also be crystallised from dilute aqueous HCl. After sublimation under high vacuum at 200o it has m 265.5o. Its solubility in H2O is 10%. [Beilstein 18 III 2361, 1 IV 2812.]
Incompatibilities
Dust may form explosive mixture with
air. Incompatible with oxidizers (chlorates, nitrates, peroxides,
permanganates, perchlorates, chlorine, bromine, fluorine,
etc.); contact may cause fires or explosions. Keep
away from alkaline materials, strong acids, organic acids,
strong bases. Aquesous solution is acidic. Explosive
compound is formed when a mixture of Pentaerythritol and
thiophosphoryl chloride (CAS 3892-91-0) is heated.
Check Digit Verification of cas no
The CAS Registry Mumber 115-77-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 5 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 115-77:
(5*1)+(4*1)+(3*5)+(2*7)+(1*7)=45
45 % 10 = 5
So 115-77-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2
115-77-5Relevant articles and documents
SELECTIVE FORMOSE REACTION CATALYZED BY DIETHYLAMINOETHANOL
Matsumoto, Toshihiko,Komiyama, Makoto,Inoue, Shohei
, p. 839 - 842 (1980)
Selective formose reactions were achieved by diethylaminoethanol as catalyst at 100 deg C in the presence and the absence of D-fructose as co-catalyst.The reaction in the presence of the co-catalyst gave 2-hydroxymethylglycerol and other three main products in high yields, whereas in its absence pentaerythritol was the sole product.
SELECTIVE FORMOSE REACTION INITIATED BY PHOTO- AND γ-IRRADIATION
IRIE, Setsuko
, p. 2153 - 2156 (1984)
A selective formose synthesis was achieved by photo- and γ-irradiation of formaldehyde in the presence of base.Photoirradiation of aqueous formaldehyde solution gave pentaerythritol as a single product, while γ-irradiation resulted in the formation of glycolaldehyde as the main product.These results suggest that the formose reaction under photo- and γ-irradiation is considerably different from the thermal formose reaction.
Photoreductive formation of acetaldehyde from aqueous formaldehyde
Schwartz, Alan W.,De Graaf
, p. 2201 - 2202 (1993)
A novel reaction is described in which acetaldehyde is formed by ultraviolet irradiation of mildly basic formaldehyde solutions. In 0.05 M potassium carbonate, the acetaldehyde produced is converted to pentaerythritol in a subsequent dark reaction.
A redox-metric study of the formation of coloring substances in the synthesis of pentaerythritol
Demchenko,Belkin
, p. 1398 - 1403 (2011)
The redox potentials of the reaction mixtures in the course of pentaerythritol synthesis and of transformations of formaldehyde and glucose in a NaOH solution without catalyst and in the presence of copper prepared by reduction of CuO were measured. Pleiades Publishing, Ltd., 2011.
PROCESS FOR PRODUCTION OF PENTAERYTHRITOL WITH AN INCREASED YIELD OF DI-PENTAERYTHRITOL
-
Page/Page column 7-10, (2020/05/13)
The present invention refers to a process for production of pentaerythritol with an increased yield of di-pentaerythritol, wherein acetaldehyde, formaldehyde, calcium hydroxide and a formose inhibitor are reacted in an aqueous solution.
A new type of pH-sensitive phospholipid
Zhan, Li,Chang, Shuyuan,Liu, Ting,Yu, Shanbao,Li, Hui,Lu, Minjie,Zhu, Yong,Luo, Yu,Yu, Jiahui,Yang, Fan,Tang, Jie
supporting information, p. 4724 - 4727 (2017/11/17)
We describe the synthesis and characterization of a type of pH-sensitive pentaerythritol phospholipids, using a trialkoxybenzylidene acetal as the acid-labile moiety. This lipid was prepared by an eight-step synthesis via a latentiation strategy. Liposomes were prepared via the thin film extrusion method. The changes of liposomal sizes were measured by dynamic light scattering. Content release rates of the liposomes as a function of pH were monitored by using a calcein fluorescence dequenching assay. These results indicated that this new liposomal system was capable of releasing its contents under mildly acidic conditions. At last, in vitro cytotoxicity was assayed against three cell lines, suggesting this type of phospholipids was low toxic.
Low ash content method for preparing calcium method for pentaerythritol (by machine translation)
-
Paragraph 0022-0024, (2017/04/03)
The present invention relates to calcium method method for preparing pentaerythritol. A low-ash content calcium method for method for preparing pentaerythritol, with formaldehyde, acetaldehyde as raw material, to calcium hydroxide is used as catalyst and reactant preparing pentaerythritol, in the condensation process, adding formaldehyde chitosan inhibitors, in order to reduce formaldehyde chitosan reaction. The formaldehyde chitosan inhibitor is alkali metal molybdate, alkaline earth metal molybdate, alkali metal tungstate and manganese salt in one or any of the several kinds of mixed, formaldehyde chitosan inhibitors of the quality of the amount of formaldehyde 1-10ppm. Low ash calcium method of the present invention method for preparing pentaerythritol, is mainly characterized in that in the condensation process by adding inhibitors, inhibit formaldehyde chitosan, calcined products can be decreased, improving the quality of products. The invention solves the problem of the calcium french season pentaerythritol ash content and high, higher quality problem of calcined, solves the problem that the pentaerythritol alcoholysis, esterification process in the presence of high calcium ash decomposition accelerating pentaerythritol, problems such as impact on the quality of the alkyd resin, has good prospects for industrial development and extension. (by machine translation)
Formaldehyde fifth heavenly stem four mellow Shan Suo double-quarter of the six-ester
-
Paragraph 0127-0128, (2017/03/21)
wherein the carboxylic acids comprise C9 branched aliphatic monocarboxylic acid, and any one of carboxylic acids selected from C4 to C8 aliphatic monocarboxylic acids. The hexaester is used as one component of a refrigerant oil composition, and gives excellent characteristics, such as oxidation stability, lubricity, and low temperature properties, to a refrigerant oil composition.
POLYOXYALKYLENE POLYOL OR MONOOL AND POLYURETHANE RESIN
-
, (2012/02/01)
An object of the present invention is to provide a polyoxyalkylene polyol and a polyoxyalkylene monool, capable of producing a urethane elastomer and a urethane foam which are sufficiently excellent in mechanical properties and moisture resistance. The present invention is directed to a polyoxyalkylene polyol or monool (S), which is an alkylene oxide adduct of an active hydrogen-containing compound (H), wherein 40% or more of hydroxyl groups located at the terminal are primary hydroxyl group-containing groups represented by the general formula (1) shown below, and a hydroxyl value x, the total degree of unsaturation y and the content of ethylene oxide z satisfy a relationship of the mathematical expression (1). [In the general formula (1), R1 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group or a phenyl group, each of which may be substituted with a halogen atom or an aryl group.] [in-line-formulae]y≦28.3×x?2×(100?z)/100??(1)[/in-line-formulae] [In the mathematical expression (1), x represents a hydroxyl value, y represents the total degree of unsaturation, and z is the content of ethylene oxide based on the weight of (S) and is from 0 to 50% by weight.
METHOD OF PREPARING PENTAERYTHRITOL
-
Page/Page column 2, (2010/06/22)
A method of preparing monopentaerythritol, dipentaerthritol, and sodium formate through high temperature condensation and cascade recrystallization is disclosed. The method lowers the energy consumption dramatically and improves the cost-effectiveness by carrying out the reaction in a non-low-temperature zone, and thereby avoiding the requirement for refrigeration. The method alleviates the difficulty of separation and improves the product quality by means of cascade separation process, and thereby avoiding the low purity from a single separation. In addition, the mother liquor obtained after each separation step is recycled to the previous step as the recycling liquor, which avoids discharging waste, increases the product yield and lowers raw materials consumption.
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