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2,2-Dimethylpropan-1,3-diol
2,2-Dimethylpropane-1,3-diol · NEOPENTYL GLYCOL · 2,2-DIMETHYL-1,3-PROPANEDIOL · 1,3-Dihydroxy-2,2-dimethylpropane · NEOPENTYL GLYCO · Neol · NPG Glycol · 2,2-Dimethyl-1
Identifikatoren & physikalische Daten
| CAS No. | 126-30-7 |
|---|---|
| Summenformel | C5H12O2 |
| Durchschnittliche Molmasse | 104,15 g/mol |
| Monoisotopische Masse | 104,08372962 g/mol |
| SMILES | CC(C)(CO)CO |
| InChIKey | SLCVBVWXLSEKPL-UHFFFAOYSA-N |
| PubChem CID | 31344 |
| ChEMBL | CHEMBL3184801 |
| ChEBI | CHEBI:143768 |
| EC No. | 204-781-0 |
| DTXSID | DTXSID8027036 |
| Lokaler Name | 2,2-Dimethylpropan-1,3-diol |
Chemische & physikalische Eigenschaften
| XLogP | 0 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 44 |
| Polymers | Other Classes -> Alcohols and Polyols, Other |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = 0.12-0.84 |
| Geruch | Sweetish |
| Dichte | 1.1 g/cu cm1.1 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.01.06 @25 °C |
| Color/Form | Needles from benzeneCrystalline solid |
| Löslichkeit | In water, 83 g/100 mL at 20 °CSolubility in water approximately 65% wet weightSoluble in waterFreely soluble in alcohol, etherFor more Solubility (Complete) data for Neopentyl glycol (6 total), please visit the HSDB record page.Solubility in water, g/100ml at 20 °C: 83830g/l830 g/L (20 ºC) |
| Flammpunkt | 225 °F (USCG, 1999)265 °F (129 °C) (open cup)107 °C |
| Siedepunkt | 406.4 °F at 760 mmHg (USCG, 1999)207 °C210 °C206 °C @760 [mm Hg]208 °C |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 260.6 °F (USCG, 1999)129.3 °C127 °C126-128 °C |
| Dampfdichte | 3.6 (Air =1)Relative vapor density (air = 1): 3.63.6 (vs air) |
| Dampfdruck | <0.8 mm Hg ( 20 °C) |
| Brechungsindex | 1.4406 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | Crystalline Chunks |
| pKa (Säurekonstante) | 14.57±0.10(Predicted) |
| Farbe | White |
| Explosionsgrenze | 1.34%, 149°F |
| Merck | 14,6458 |
| BRN | 605291 |
| Henry-Konstante | 4.0×102 mol/(m3Pa) at 25℃, Wang et al. (2017) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, acetic anhydride, acid chlorides, moisture. Combustible. |
| Kosmetik-Inhaltsstoffe Funktionen | SOLVENTPLASTICISER |
| InChI | 1S/C5H12O2/c1-5(2,3-6)4-7/h6-7H,3-4H2,1-2H3 |
| InChIKey | SLCVBVWXLSEKPL-UHFFFAOYSA-N |
| SMILES | CC(C)(CO)CO |
| LogP (Verteilungskoeffizient) | -0.15 at 25℃ |
| CAS Datenbank | 126-30-7(CAS DataBase Reference) |
| NIST chemische Informationen | 1,3-Propanediol, 2,2-dimethyl-(126-30-7) |
| EPA chemische Informationen | Neopentyl glycol (126-30-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.9% (19 of 1013) of reports.DangerH315 (21.1%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P305+P354+P338, P317, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 1013 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1,3-Propanediol, 2,2-dimethyl-1,3-Propanediol, 2,2-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanediol, 2,2-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 28-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/150791,3-Propanediol, 2,2-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1,3-Propanediol, 2,2-dimethyl-: Human health tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Special Hazards of Combustion Products: Emits toxic fumes under fire condition. (USCG, 1999)Combustible. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | Combustible when exposed to heat or flame. |
| Gesundheitsgefahren | May be harmful by ingestion or skin absorption. Causes eye and skin irritation. Material is irritating to mucous membrane and upper respiratory tract. INHALATION: Call for medical aid. Remove to fresh air. If breathing has stopped, give artificial respiration. If breathing is difficult, give oxygen. (USCG, 1999) |
| Gefahrenübersicht | An eye and respiratory tract irritant[ICSC] Effects to male liver and kidney but no reproductive or developmental toxicity observed in oral study of rats[JECDB] An irritantMay cause smarting and reddening of skin if spilled and allowed to remain on clothesHigh vapor concentrations may cause mild smarting of eyes and respiratory system[CHRIS] A severe eye irritant that may cause injury[Alfa Aesar MSDS] |
| Reaktive Gruppe | Alcohols and Polyols |
| EPA Safer Chemical | Chemical: Neopentyl glycol |
| Reactivity Profile | 2,2-DIMETHYLPROPANE-1,3-DIOL may generate toxic gases in combination of with alkali metals, nitrides, and strong reducing agents. Reacts with inorganic acids and carboxylic acids to form esters plus water. Converted to aldehydes or acids by oxidizing agents. May initiate the polymerization of isocyanates and epoxides. |
| Chemical Dangers | Reacts violently with oxidants. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Brandbekämpfung | Fire Extinguishing Agents: Water sprays, dry chemical powder, alcohol or polymer foam. (USCG, 1999)Use water spray, powder. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. |
| Erste Hilfe | EYES: Flush with copious amounts of water. |
| Sichere Lagerung | Separated from oxidants. Dry. |
| Brandbekämpfungsverfahren | Water or foam may cause frothing.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. |
| Freisetung ohne Brand | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Entsorgungsverfahren | SRP: 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Contact a licensed professional waste disposal service to dispose of this material. Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Personal protection: P2 filter respirator for harmful particles. Sweep spilled substance into covered containers. Remove gas with fine water spray. |
| Preventive Measures | Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains.Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that neopentyl glycol is expected to have very high mobility in soil(SRC). Volatilization of neopentyl glycol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X1-07 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Neopentyl glycol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.27X10-2 mm Hg at 25 °C(3). Utilizing the Japanese MITI test, 1.2% of the Theoretical BOD was reached in 2 weeks(4) indicating that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that neopentyl glycol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.1X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 122 and 890 days, respectively(SRC). According to a classification scheme(4), a BCF range of 0.3-0.5(5) suggests bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 1.2% of the Theoretical BOD was reached in 2 weeks(5) indicating that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), neopentyl glycol, which has a estimated vapor pressure of 1.27X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase neopentyl glycol 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 44 hrs(SRC), calculated from its rate constant of 8.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Neopentyl glycol 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). |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol and by ingestion. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Neopentyl glycol (NPG) is a solid. It is used in chemical synthesis, and in polyester manufacture. An insect repellent. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: NPG was not irriating to skin in rabbits, and non sensitizing to the skin in the Murine Local Lymph Node Assay. NPG was practically non-toxic in acute studies in rats and guinea pigs. No treatment-related, adverse findings were observed at clinical examinations, clinical pathology and pathology up to a dose level of 1000 mg/kg bw/d in 90 day oral gavage studies in rats. In other rat study reproductive performance of the parent generation and development of the F1 generation were not affected after oral application of dose levels up to 1000 mg/kg bw/day. In male rats single i.p. injection of 2000 mg/kg bw resulted in a mid level of ataxia but no loss of righting reflex. NPG had no mutagenic activity in Salmonella typhimurium TA 100, TA 1535, TA 98, TA 1537, or in Escherichia coli WP2 uvrA tested with and without metabolic activation at dose levels up to 5000 ug/plate. NPG was not mutagenic in the HPRT locus assay under in vitro conditions in CHO cells in the absence and the presence of metabolic activation. |
| Signs and Symptoms | Cough.Redness.Redness. Pain.Burning sensation. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of August 9, 2018: http://actor.epa.gov/dashboard/] |
| Effluent Concentrations | Neopentyl glycol was detected at a concentraiton of 14.7 ug/L in an industrial landfill leachate sampled Decemeber 1996. It was not detected in in an industrial effluent from a petrochemical plant taken in July 1996, January 1997, or March 1997 (landfill leachate)detection limit = 1.0 ug/L(1). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of neopentyl glycol can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that neopentyl glycol is expected to have very high mobility in soil(SRC). |
| Human Toxicity Excerpts | /BIOMONITORING/ Patients attending a general hospital for various reasons were screened for raised serum gamma glutamyltransferase (gamma-GT) and positive blood alcohol concentration (BAC). The results served as objective biochemical tests of heavy drinking. Among 419 individuals, 50 (11.9%) met these requirements and blood samples were used to determine the presence of low molecular mass aliphatic diols. 1,2-Propanediol, 2,3-butanediol and 2,2-dimethyl-1,3-propanediol were determined by gas liquid chromatography-mass spectrometry (GC-MS). In patients with blood ethanol concentration less than 2 mmol/L, 1,2-propanediol and 2,2-dimethyl-1, 3-propanediol mainly occurred together at median concentrations of about 200 umol/L. When blood ethanol was 2-42 mmol/L, 2,3-butanediol was also present covering a wide concentration range: three patients had concentrations between 6 and 10 mmol/L. There was no apparent correlation between the concentration of 2,3-butanediol and the concentration of blood ethanol. The diols were below the limits of detection in blood from nonintoxicated control individuals and hospital in-patients. |
| Artificial Pollution Sources | Neopentyl glycol's production and use in the production of plasticizers and polyesters and as a modifier of alkyd resins(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Neopently glycol has been identified as considered nonbiodegradable in a relatively short time frame(1). Neopentyl glycol, present at 100 mg/L, reached 1.2% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(2).ANAEROBIC: Neopentyl glycol was 1% biodegraded following a lag of >60 days when incubated with an anaerobic digesting sludge from the Reading Sewage Works, Berkshire, UK(1). |
| Environmental Bioconcentration | A BCF range of 0.3-0.5 was calculated in fish for neopentyl glycol at 10 ppm using carp (Cyprinus carpio) which were exposed over an 6-week period(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for neopentyl glycol is estimated as 3.1X10-7 atm-cu m/mole(SRC) developed using a fragment constant estimation method(1). This Henry's Law constant indicates that neopentyl glycol is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 122 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 890 days(SRC). Neopentyl glycol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Neopentyl glycol is is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.27X10-2 mm Hg(3). |
| F | 3 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29053990 |
| RTECS-Nr. | TY5775000 |
| R-Sätze (R) | 36/37/38-36-41 |
| Toxizität | rat,LCLo,inhalation,39000ppm/6H (39000ppm),Kodak Company Reports. Vol. 21MAY1971, |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 126-30-7(Hazardous Substances Data) |
| Gefahrenklasse | Eye Dam. 1 |
| Selbstentzündungstemperatur | 750 °F |
Anwendungen & Verwendung
Verwenden
2,2-Dimethyl-1,3-propanediol may be used in the synthesis of:2,2-dimethyl-1,3-propanediol cyclic phosphorochloridate2,2-dimethyl-1,3-propanediol cyclic phenylphosphonate[1′,3′-(2′,2′-dimethylpropylene)]-2-iodo-3-octyl-5-thienylboronatecyclic carbonate2,2-dimethyl-1,3-propanediol bis(cyclic-2,2-dimethyltrimethylene phosphite)