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Pentaerythritol(CAS No. 115-77-5)

Pentaerythritol C5H12O4 (cas 115-77-5) Molecular Structure

115-77-5 Structure

Identification and Related Records

【Name】
Pentaerythritol
【CAS Registry number】
115-77-5
【Synonyms】
Pentaerythritol Tech Grade
Tetrahydroxymethylmethane
1,3-propanediol, 2,2-bis(hydroxymethyl)-
Methane tetramethylol
Pentaerythrite
Pentaerythritol(PE)
Pentaerythritol, technical grade
Petaerythritol
Mo-pentaerythritol
New plasticizer Polyol benzoate
Sell Pentaerythritol
pentaerythritol (mono-penta)
Mono- Pentaerythritol
Pentaerythritol

Pentaerythritol(Micronized)
Pentaerythritol for Sale
Pentaerithritol
Penetek
Pentek
1,3-Propanediol, 2, 2-bis (hydroxymethyl)-
2,2-bis(hydroxymethyl)propane-1,3-diol
Tetramethylolmethane
1,3-Propanediol,2,2-bis(hydroxymethyl)-
2,2-Bishydroxymethyl-1,3-propanediol
Tetrakis(hydroxymethyl)methane
【EINECS(EC#)】
204-104-9
【Molecular Formula】
C5H12O4 (Products with the same molecular formula)
【Molecular Weight】
136.15
【Inchi】
InChI=1/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2
【Canonical SMILES】
C(C(CO)(CO)CO)O
【MOL File】
115-77-5.mol

Chemical and Physical Properties

【Appearance】
white crystalline solid
【Density】
1.396
【Melting Point】
257-263℃
【Boiling Point】
276℃ (30 mmHg)
【Vapour】
2.38E-07mmHg at 25°C
【Refractive Index】
1.548
【Flash Point】
240℃
【Water】
1 g/18 mL (15℃)
【Solubilities】
1 g/18 mL (15 °C) in water
【Color/Form】
Ditetragonal crystals from dilute hydrochloric acid
White, crystalline powder
Colorless to white, crystalline powder [Note: Technical grade is 88% monopentaerythritol & 12% dipentaerythritol].
【Stability】
Stable. Incompatible with strong acids, strong oxidizing agents, acid chlorides, acid anhydrides. Combustible.
【HS Code】
29054200
【Storage temp】
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
【Spectral properties】
Index of refraction: 1.548 at 25 deg C/D
SADTLER REF NUMBER: 2480 (IR, PRISM)
IR: 5580 (Coblentz Society Spectral Collection)
1H NMR: 17054 (Sadtler Research Laboratories Spectral Collection)
MASS: 3414 (NIST/EPA/MSDC Mass Spectral database, 1990 version); 233 (Aldermaston, Eoght Peak Index of Mass Spectra, U.K.)
【Computed Properties】
Molecular Weight:136.14638 [g/mol]
Molecular Formula:C5H12O4
XLogP3-AA:-2.4
H-Bond Donor:4
H-Bond Acceptor:4
Rotatable Bond Count:4
Exact Mass:136.073559
MonoIsotopic Mass:136.073559
Topological Polar Surface Area:80.9
Heavy Atom Count:9
Formal Charge:0
Complexity:51.8
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:4
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:7

Safety and Handling

【Risk Statements】
R33
【Safety Statements 】
S24/25
【Safety】

Risk Statements: 33
R33:Danger of cumulative effects.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: RZ2490000
HS Code: 29054200

【PackingGroup 】
Z01
【Sensitive】
Hygroscopic
【Skin, Eye, and Respiratory Irritations】
Irritation of eyes, respiratory system
【Cleanup Methods】
Spill Handling: Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.
【Transport】
无资料?
【Fire Fighting Procedures】
This chemical is a combustible solid. Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or the shows any signs of deforming), withdraw immediately to a secure position.
【Fire Potential】
Flammable from heat or flame or oxidizers.
【Formulations/Preparations】
Grades: Technical, nitration, CP. Technical grade is 88% monopentaerythritol and 12% dipentaerythritol.
Essentially three grades of pentaerythritol are manufactured: (1) "Mono" pentaerythritol containing a minimum of 97.0-98.0% pentaerythritol and small amounts of dipentaerythritol and the linear form of pentaerythritol; (2) technical-grade pentaerythritol containing 81-91% pentaerythritol, 8-18% dipentaerythritol, and small amounts of tripentaerythritol and linear form of pentaerythritol; and (3) nitration-grade pentaerythritol which is a highly purified grade and has a minimum assay of 98-99% pentaerythritol.
CHEMICAL PROFILE: Pentaerythritol. Production usually includes three grades of pentaerythritol; mono (97-98%, with di- and tri-pentaerythritol impurities), technical (88%, with 8-10% dipentaerythritol, balance tri-) and nitration (98-99%, with di- and tripentaerythritol impurities).
【Reactivities and Incompatibilities】
Mixtures with thiophosphoryl chloride react when heated to form a product that ignites and then explodes on contact with air.
Organic acids, oxidizers
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Contact lenses should not be worn when working with this chemical.
【Protective Equipment and Clothing】
Irritation of eyes, respiratory system
【Specification】

?Pentaerythritol (CAS NO.115-77-5) is the organic compound with the formula C(CH2OH)4. It belongs to the class of polyhydric alcohols or polyols. And it?is moderately soluble in water.?Pentaerythritol (CAS NO.115-77-5) is a versatile building block for the preparation of many polyfunctionalized compounds such as the explosive PETN and pentaerythritol triacrylate. Derivatives of pentaerythritol are components of alkyd resins, varnishes, PVC stabilizers, tall oil esters and olefin antioxidants.

【Octanol/Water Partition Coefficient】
log Kow = -1.69
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
The following wastewater treatment technology has been investigated for pentaerythritol: Concentration process: Biological treatment.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

CHEMICAL PROFILE: Pentaerythritol. Commercial production is from formaldehyde and acetaldehyde.
CHEMICAL PROFILE: Pentaerythritol. The synthesis of pentaerythritol involves reacting four moles of formaldehyde and one mole of acetaldehyde in two differentiated steps. The first is an aldol condensation to give pentaerythritose. Then, the aldehyde obtained is subjected to a crossed Cannizzaro reaction, whereby one molecule of the pentaerythritose is reduced to pentaerythritol, which is then separated. The raw pentaerythritol is dissolved again and subjected to high temperature acid hydrolysis, then purified in an activated carbon bed, concentrated and crystallized.
Reaction of acetaldehyde with an excess of formaldehyde in an alkaline medium. [Lewis RJ Sr; Hawley's Condensed Chemical Dictionary 15th ed Wiley (2007)
U.S. Exports

(1972) Negligible
(1975) Negligible
(1984) 5.48 X 10+8 g
CHEMICAL PROFILE: Pentaerythritol. US Exports: 1988: 15 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Exports: 1991: 25 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Exports: 1994: 17 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Exports: 1997: 25 million pounds; averaged 20 million pounds annually during the 1992-1996 period.
CHEMICAL PROFILE: Pentaerythritol. US Exports: 1998: 26.1 million pounds; 1999: 31 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Exports: 2001: 31 million pounds; 2002: 27 million pounds..
CHEMICAL PROFILE: Pentaerythritol. US Exports: 2004: 20 million pounds; 2005: 16 million pounds..
U.S. Imports

(1972) 6.36 X 10+8 g
(1975) 1.7 X 10+9 g
(1984) 7.20 X 10+9 g /Dipentaerythritol and Pentaerythritol/
CHEMICAL PROFILE: Pentaerythritol. US Imports: 1988: 15 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Imports: 1991: 17 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Imports: 1994: 26 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Imports: 1997: 24 million pounds; averaged 25 million pounds per year during the 1992-1996 period.
CHEMICAL PROFILE: Pentaerythritol. US Imports: 1998: 36.5 million pounds; 1999: 34 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Imports: 2001: 36 million pounds; 2002: 18 million pounds.
CHEMICAL PROFILE: Pentaerythritol. US Imports: 2004: 22 million pounds; 2005: 33 million pounds.
U.S. Production

(1972) 5.0 X 10+10 g
(1975) 4.57 X 10+10 g
(1984) 4.80 X 10+10 g
(1991) 158 million lb
CHEMICAL PROFILE: Pentaerythritol. US Production Capacity: 1986: 158 million pounds/year.
CHEMICAL PROFILE: Pentaerythritol. US Production Capacity: 1989: 158 million pounds/year.
CHEMICAL PROFILE: Pentaerythritol. US Production Capacity: 1992: 158 million pounds/year.
CHEMICAL PROFILE: Pentaerythritol. US Production Capacity: 1995: 158 million pounds/year.
CHEMICAL PROFILE: Pentaerythritol. US Production Capacity: 1997: 158 million pounds/year.
CHEMICAL PROFILE: Pentaerythritol. US Production Capacity: 2000: 168 million pounds/year.
CHEMICAL PROFILE: Pentaerythritol. US Production Capacity: 2003: 169 million pounds/year.
CHEMICAL PROFILE: Pentaerythritol. US Production Capacity: 2006: 90 million pounds/year.
CHEMICAL PROFILE: Pentaerythritol. Global capacity was 465,400 tonnes/year in 2006, with 161,100 tonnes/year in Asia-Pacific (excluding Japan), 115,450 tonnes/year in Western Europe, 76,400 tonnes/year in the US, ... and 31,500 tonnes/year in Japan.
1,3-Propanediol, 2,2-bis(hydroxymethyl)- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >50 million - 100 million 1990 >100 million - 500 million 1994 >100 million - 500 million 1998 >100 million - 500 million 2002 >100 million - 500 million
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,3-Propanediol, 2,2-bis(hydroxymethyl)-. Aggreated National Production Volume: 100 to
Consumption Patterns

70% as a chemical intermediate for alkyd resins; 13% as a chemical intermediate for rosin and tall oil esters; 7% as a chemical intermediate for synthetic lubricants; 3.5% as a chemical intermediate for pentaerythritol tetranitrate; 6.5% in miscellaneous applications (1974)
Pentaerythritol finds its main use in surface-coating compositions, especially in the manufacture of alkyd resins (1978).
CHEMICAL PROFILE: Pentaerythritol: US End-use Pattern for Pentaerythritol in 1986 End-use Pattern for pentaerythritol in 1986 End-use Percent Alkyd resins 60 Synthetic lubricants and additives 12 Rosin and tall oil esters 9 Pentaerythritol tetranitrate 3 Other, including flame retardants, pentaerythritol triacrylate and protective coatings 16
CHEMICAL PROFILE: Pentaerythritol: US End-use Pattern for Pentaerythritol in 1989 End-use Pattern for pentaerythritol in 1989 End-use Percent Alkyd resins 60 Synthetic lubricants and additives 10 Rosin and tall oil esters 10 Pentaerythritol tetranitrate 5 Other, including flame retardants, pentaerythritol triacrylate and protective coatings 15
CHEMICAL PROFILE: Pentaerythritol: End-use Pattern for Pentaerythritol in 1992 End-use Pattern for pentaerythritol in 1992 End-use Percent Alkyd resins 63 Fatty acid esters 11 Rosin and tall oil esters 10 Pentaerythritol tetranitrate 4 Other, including flame retardants, polyvinyl chloride stabilizers, antioxidant for olefins, and pentaerythritol triacrylate 12
CHEMICAL PROFILE: Pentaerythritol: End-use Pattern for Pentaerythritol in 1995 End-use Pattern for pentaerythritol in 1995 End-use Percent Alkyd resins 61 Fatty acid esters 12 Rosin and tall oil esters 12 Pentaerythritol tetranitrate (PETN) 4 Miscellaneous, including polyurethanes, flame retardants, polyvinyl chloride stabilizers, olefins antioxidant, and pentaerythritol triacrylate 11
CHEMICAL PROFILE: Pentaerythritol: End-use Pattern for Pentaerythritol in 1997 End-use Pattern for pentaerythritol in 1997 End-use Percent Alkyd resins 60 Fatty acid esters 15 Rosin and tall oil esters 10 Miscellaneous, including pentaerythritol tetranitrate, urethane coatings, flame retardant paints, polyvinyl chloride stabilizers, olefins antioxidant, and pentaerythritol triacrylate 15
CHEMICAL PROFILE: Pentaerythritol: End-use Pattern for Pentaerythritol in 2000 End-use Pattern for pentaerythritol in 2000 End-use Percent Alkyd resins 50 Fatty acid esters 23 Rosin and tall oil esters 12 Miscellaneous, including urethane coatings, flame retardant paints, polyvinyl chloride stabilizers, olefin antioxidants, and pentaerythritol triacrylate 12
CHEMICAL PROFILE: Pentaerythritol: End-use Pattern for Pentaerythritol in 2003 End-use Pattern for pentaerythritol in 2003 End-use Percent Alkyd resins 60 Neopolyol esters for lubricants 16 Rosin and tall oil esters 11 Pentaerythritol tetranitrate (PETN) 4 Miscellaneous, including urethane coatings, flame retardant paints, polyvinyl chloride stabilizers, olefins antioxidants, and pentaerythritol triacrylate 9
CHEMICAL PROFILE: Pentaerythritol: End-use Pattern for Pentaerythritol in 2006 End-use Pattern for pentaerythritol in 2006 End-use Percent Alkyd resins 58 Neopolyol esters for lubricants 16 Rosin and tall oil esters 12 Pentaerythritol tetranitrate (PETN) 4 Miscellaneous, including urethane coatings, flame retardant paints, polyvinyl chloride stabilizers, olefins antioxidant, and pentaerythritol triacrylate 10
CHEMICAL PROFILE: Pentaerythritol: Worldwide End-use Pattern for Pentaerythritol in 2006 Worldwide End-use Pattern for pentaerythritol in 2006 End-use Percent Alkyd paints 37 Alkyd inks 14.5 Alkyd adhesives/sealants 11 Plasticizers 9 Alkyd varnishes for floors and woodwork 8 Radiation cure coatings 7 Lubricants 4 Explosives 1.3 Other applications 8.2
CHEMICAL PROFILE: Pentaerythritol. US Demand: 1985: 124 million pounds; 1986: 125 million pounds; 1990: 132 million pounds /projected/.
CHEMICAL PROFILE: Pentaerythritol. US Demand: 1988: 125 million pounds; 1989: 125 million pounds; 1993: 130 million pounds /projected/.
CHEMICAL PROFILE: Pentaerythritol. US Demand: 1991: 116.9 million pounds; 1992: 119 million pounds; 1996: 126 million pounds /projected/.
CHEMICAL PROFILE: Pentaerythritol. US Demand: 1994: 125 million pounds; 1995: 127 million pounds; 1999: 135 million pounds /projected/.
CHEMICAL PROFILE: Pentaerythritol. US Demand: 1996: 135 million pounds; 1997: 140 million pounds; 2001: 160 million pounds /projected/.
CHEMICAL PROFILE: Pentaerythritol. US Demand: 1998: 155.4 million pounds; 1999: 157.4 million pounds; 2003: 165.7 million pounds /projected/.
CHEMICAL PROFILE: Pentaerythritol. US Demand: 2001: 150 million pounds; 2002: 136 million pounds; 2006: 140 million pounds, projected.
CHEMICAL PROFILE: Pentaerythritol. US Demand: 2004: 130 million pounds; 2005: 128 million pounds; 2009: 131 million pounds, projected.
CHEMICAL PROFILE: Pentaerythritol. Global Demand: Global demand in 2006 was 376,460 tonnes/year. Asia-Pacific was the largest exporter at 25,270 tonnes/year and the US was the largest importer with 21,860 tonnes/year.
CHEMICAL PROFILE: Pentaerythritol. Asia-Pacific is the largest consumer, at about 118,900 tonnes/year, followed by Western Europe at 88,400 tonnes/year and the US at 70,700 tonnes/year. Asia/Middle East, Japan, and Eastern Europe consume 26,740 tonnes/year, 23,510 tonnes/year, and 21,120 tonnes/year, respectively.
【Usage】

Chemical intermediate for alkylated resins, synth lubricants, pentaerythritol tetranitrate & resin & tall oil esters.

Biomedical Effects and Toxicity

【Pharmacological Action】
Non-toxic; no symptoms likely
【Biomedical Effects and Toxicity】
10 mg/kg (14)C-pentaerythrite, administered orally to 12 mice (females), was absorbed and excreted rapidly. Half of the administered dose left the gastrointestinal tract within 15 min and 68% of the dose appeared in the urine and feces after 4 hr. The compound detected was pentaerythrite.
In ... experiments with (14)carbon pentaerythritol, 69% of (14)carbon was excreted, probably as unchanged compound, in 24 hr urine and 23% in feces /after oral administration to dogs/. Blood levels were greatest after 1 hr.
Kinetics of urinary excretion of pentaerythritol were first order and apparently dose-independent ...
Feeding studies in human volunteers revealed that about 85% of pentaerythritol fed was eliminated unchanged in urine. Elimination was essentially complete in 30 hr.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.5(SRC), determined from a log Kow of -1.69(2) and a regression-derived equation(3), indicates that pentaerythritol is expected to have very high mobility in soil(SRC). Volatilization of pentaerythritol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Pentaerythritol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-8 mm Hg at 25 deg C(SRC), determined from a fragment constant method(5). Utilizing the Japanese MITI test, 13.2% of the Theoretical BOD was reached in 25 days(6) indicating that biodegradation is not an important environmental fate process in soil(SRC). However, aerobic biodegradation test results for pentaerythritol do show varying results(7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.5(SRC), determined from a log Kow of -1.69(2) and a regression-derived equation(3), indicates that pentaerythritol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 4.1X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), a BCF range of 0.3-2.1 using carp (Cyprinus carpio)(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 13.2% of the Theoretical BOD was reached in 25 days(7) indicating that biodegradation is not an important environmental fate process in water(SRC). However, aerobic biodegradation test results for pentaerythritol do show varying results(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pentaerythritol, which has an estimated vapor pressure of 2.5X10-8 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase pentaerythritol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 26 hrs(SRC), calculated from its rate constant of 1.48X10-11 cu cm/molecule-sec at 25 deg C(3). Particulate-phase pentaerythritol may be removed from the air by wet or dry deposition(SRC). Pentaerythritol does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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