Neopentyl glycol

HCID 31344CAS 126-30-7

基本情報

標準SMILES
CC(C)(CO)CO
InChIKey
SLCVBVWXLSEKPL-UHFFFAOYSA-N
分子式
C5H12O2
平均分子量
104.15 g/mol
単同位体質量
104.08372962

概要

2,2-dimethylpropane-1,3-diol is a white crystalline solid. Melting point 130 °C.

名称と識別子

優先名称
Neopentyl glycol
IUPAC
2,2-dimethylpropane-1,3-diol
現地名
2,2-ジメチル-1,3-プロパンジオール
英語名
neopentyl glycol
分子式
C5H12O2
分子量
104.15

名称と別名

Neopentyl glycol126-30-72,2-Dimethylpropane-1,3-diol2,2-DIMETHYL-1,3-PROPANEDIOLDimethylolpropaneNeopentanediolNeopentylene glycol1,3-Propanediol, 2,2-dimethyl-NeopentylglycolNeolDimethyltrimethylene glycolHydroxypivalyl alcohol
名称をさらに表示
2,2-ジメチル-1,3-プロパンジオール2,2-ジメチルプロパン-1,3-ジオール2,2-ジメチルトリメチレングリコールネオペンチルグリコールネオールネオペンチルグリコル2-2,ジメチル-1,3-プロパンジオ-ル2,2ジメチルプロパン1,3ジオルネオペンチルグリコール(2,2-ジメチル-1,3-プロパンジオール)ジメチルトリメチレングリコール2,2-ジヒドロキシ-2,2-ジメチルプロパン2,2-ビス(ヒドロキシメチル)プロパン2,2‐ジメチル‐1,3‐プロパンジオールネオペンチレングリコールNEOPENTYL GLYCONPG Glycol2,2-Dimethyl-1
2,2-Dimethyltrimethylene glycolNexcoat 6002,2-Dimethyl-1,3 propanediolDTXSID8027036QI80HXD6S5ORISTAR NPGNSC-63661,3-Dihydroxy-2,2-dimethylpropane

データベース識別子

CAS
126-30-7
PubChem CID
31344
DTXSID
DTXSID8027036
ChEMBL
CHEMBL3184801
ChEBI
CHEBI:143768
UNII
QI80HXD6S5
EC Number
204-781-0
Nikkaji
J2.511I

物性

構造計算による物性

XLogP
0
極性表面積
40.5 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
2
重原子数
7

実験および物理化学的性質

PolymersOther Classes -> Alcohols and Polyols, Other
SpringerMaterials PropertiesBoiling point
LogP · 2 件

log Kow = 0.12

-0.84

OdorSweetish
Density · 4 件

1.1 g/cu cm

1.1 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

1.06 @25 °C

Color/Form · 2 件

Needles from benzene

Crystalline solid

物理化学的性質

融点
126 · 126-128 °C
沸点
208 °C · 208 °C
比重(密度)
1.06 · 1.06
蒸気密度
3.6 · 3.6 (vs air)
蒸気圧
0.8 mm · <0.8 mm Hg ( 20 °C)
屈折率
1.4406 · 1.4406 (estimate)

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 1.9% (19 of 1013) of reports.

Danger

H315 (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.

Danger

危険有害性情報

Regulatory Information · 4 件

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/15079

1,3-Propanediol, 2,2-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1,3-Propanediol, 2,2-dimethyl-: Human health tier I assessment
DOT LabelPoison
Fire Hazards · 2 件

Special Hazards of Combustion Products: Emits toxic fumes under fire condition. (USCG, 1999)

Combustible. Finely dispersed particles form explosive mixtures in air.

Fire PotentialCombustible when exposed to heat or flame.
Health Hazards · 1 件

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)

安全と保護具

Fire Fighting · 2 件

Fire Extinguishing Agents: Water sprays, dry chemical powder, alcohol or polymer foam. (USCG, 1999)

Use water spray, powder.

First Aid Measures · 4 件

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.

First AidEYES: Flush with copious amounts of water.
Safe StorageSeparated from oxidants. Dry.
Fire Fighting Procedures · 2 件

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.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Hygroscopic.

毒性情報

Environmental Fate · 3 件

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).

Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Toxicity Summary · 1 件

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 · 4 件

Cough.

Redness.

Redness. Pain.

Burning sensation.

Ongoing Test Status · 1 件

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/[USEPA; ICSS Dashboard Application; Available from, as of August 9, 2018: http://actor.epa.gov/dashboard/]

Effluent Concentrations · 1 件

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).

安全データ

F
3
wgk
1
tsca
TSCA listed
rtecs
TY5775000
毒性
rat,LCLo,inhalation,39000ppm/6H (39000ppm),Kodak Company Reports. Vol. 21MAY1971,
hs_code
29053990

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

4 rabbits were gavaged with 1000 -1500 mg/kg bw unlabelled neopentyl glycol and excretion of the test substance and their metabolites via urine was determined the following 24 hr (pooled data). After oral application 62% (range 53-67%) of the applied dose was found in the 24-hr urine as the conjugate of glucuronic acid indicating rapid absorption. Only 1.9% of the applied dose was excreted as 3-hydroxy-2,2-dimethylpropionic acid and 0.7% as unchanged neopentyl glycol. Conclusion: Rapid absorption of the test substance after oral exposure followed by conjugation with glucuronic acid and excretion via urine.

Absorption, Distribution and Excretion · 1 件

4 rabbits were gavaged with 1000 -1500 mg/kg bw unlabelled neopentyl glycol and excretion of the test substance and their metabolites via urine was determined the following 24 hr (pooled data). After oral application 62% (range 53-67%) of the applied dose was found in the 24-hr urine as the conjugate of glucuronic acid indicating rapid absorption. Only 1.9% of the applied dose was excreted as 3-hydroxy-2,2-dimethylpropionic acid and 0.7% as unchanged neopentyl glycol. Conclusion: Rapid absorption of the test substance after oral exposure followed by conjugation with glucuronic acid and excretion via urine.

用途と製造

Uses · 6 件

Used to make plasticizers and polyesters and as modifier of alkyd resins; [Merck Index] Used in chemical synthesis and in the polymers industry; [IUCLID] Used to make large scale and fine chemicals, rubber products, plastic products, textiles, leather, fur, wood and wood products, pulp-paper and paper products, non-metallic mineral products (i.e. plasters and cement), in printing and reproduction of recorded media, building and construction work, scientific research and development, and consumer construction chemicals; [ECHA REACH Registrations]

Pulp and Paper Processing [Category: Industry]

In the manufacture of plasticizers, polyesters, as modifier of alkyd resins.

Used in polyester manufacture. An insect repellent.

Application: 2,2-Dimethyl-1,3-propanediol may be used in the synthesis of: 2,2-dimethyl-1,3-propanediol cyclic phosphorochloridate; 2,2-dimethyl-1,3-propanediol cyclic phenylphosphonate; [1',3'-(2',2'-dimethylpropylene)]-2-iodo-3-octyl-5-thienylboronate; cyclic carbonate; 2,2-dimethyl-1,3-propanediol bis(cyclic-2,2-dimethyltrimethylene phosphite)

Synthetic lubricants.

ImpuritiesImpurities may include neopentyl glycol monoformate, neopentyl glycol monoisobutyrate, 2,2,4-trimethyl-1,3-pentanediol, and the cyclic acetal from the reaction of hydroxypivaldehyde and neopentyl glycol.
U.S. Production · 2 件

2023: 100,000,000 - <250,000,000 lb

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,3-Propanediol, 2,2-dimethyl-:

Consumer UsesPlasticizer
Industry UsesIntermediate
Methods of Manufacturing · 1 件

The aldol addition of isobutyraldehyde (2-methylpropanal) and formaldehyde gives hydroxypivaldehyde (3-hydroxy-2,2- dimethylpropanal), which is then reduced to neopentyl glycol. ... Both aldol addition and subsequent reduction are exothermic. Hydroxypivaldehyde can be reduced either by a crossed Cannizzaro reaction with equimolar amounts of formaldehyde and a base, or by catalytic hydrogenation.

応用分野 · 2 件

使用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)

一般的な説明White crystalline solid. Melting point 130°C.

調製方法

純化方法Crystallise the diol from *benzene or acetone/water (1:1). [Beilstein 1 IV 2551.]

サプライヤー50 社

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補足説明

定義本品は、次の化学式で表される有機化合物である。

関連反応

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