기본 정보
- 표준 SMILES
OCCCCCCO- InChIKey
XXMIOPMDWAUFGU-UHFFFAOYSA-N- 분자식
- C6H14O2
- 평균 분자량
- 118.17 g/mol
- 단동위원소 질량
- 118.09937969
개요
Hexane-1,6-diol is a diol that is hexane substituted by hydroxy groups at positions 1 and 6. It is a primary alcohol and a diol. It derives from a hydride of a hexane.
이름 및 식별자
- 우선 이름
- 1,6-Hexanediol
- IUPAC
- hexane-1,6-diol
- 영어명
- 1,6-Hexanediol
- 분자식
- C6H14O2
- 분자량
- 118.17416
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
27236-13-1、629-11-8- PubChem CID
- 12374
- DTXSID
DTXSID1027265- ChEMBL
CHEMBL458616- ChEBI
CHEBI:43078- UNII
- ZIA319275I
- EC Number
- 211-074-0、608-061-0
- Nikkaji
- J6.886A
물성
구조 계산 물성
- XLogP
- 0.3
- 극성 표면적
- 40.5 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 8
- 형식 전하
- 0
- 복잡도
- 31.5
실험 및 물리화학적 성질
Density
0.967 g/cu cm at 25 °C
Density: 0.953 g/cm cu at 50 °C
0.96 g/cm³
0.967 @ 0°C
Solubility
Soluble in water
Soluble in alcohol; sparingly soluble in hot ether.
Solubility in water: good
Flash Point
101 °C
102 °C (216 °F) - closed cup
101 °C
Boiling Point
208 °C
208 °C
250 °C @760 [mm Hg]
Melting Point
41.5 °C
42.8 °C
Vapor Density
4.07 (Air = 1)
Relative vapor density (air = 1): 4.1
물리화학적 성질
- 녹는점
- 38 · 38-42 °C
- 끓는 점
- 208 °C · 208 °C
- 밀도
- 0.967 g/cm3 · 0.967 g/cm3(Temp: 0 °C)
- 증기압
- 0.01 hPa · < 0.01 hPa
- 인화점
- 102 · 102.0
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 14.87 · 14.87±0.10(Predicted)
- 색상
- 하얀색
- 폭발한계
- 6.6 · 6.6-16 %(V)
- 수용성
- 20 °C에서 · 20°C에서 1.000g/l
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 98.1% (4470 of 4556) of all reports.
Not Classified
Aggregated GHS information provided per 4556 reports by companies from 6 notifications to the ECHA C&L Inventory.
This chemical does not meet GHS hazard criteria for 100% (25 of 25) of all reports.
Not Classified
Aggregated GHS information provided per 25 reports by companies from 1 notifications to the ECHA C&L Inventory.
유해성 정보
Regulatory Information
Chemical: 1,6-Hexanediol
1,6-Hexanediol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,6-Hexanediol 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: 02-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15109
1,6-Hexanediol: Does not have an individual approval but may be used under an appropriate group standard
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Hexamethylene glycol is produced, as an intermediate or a final product, by process units covered under this subpart.
Hazard Classes and Categories
Not Classified
Not Classified
안전 및 보호
First Aid Measures
Fresh air, rest.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Give one or two glasses of water to drink.
Fire Fighting Procedures
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
To fight fire, use foam, /carbon dioxide/, dry chemical
Cleanup Methods
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Avoid breathing dust. Environmental precautions: No special environmental precautions required. 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.
Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.
Disposal Methods
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 quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and 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: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.
Preventive Measures
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Avoid breathing dust. Environmental precautions: No special environmental precautions required.
Precautions for safe handling: Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
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.
For more Preventive Measures (Complete) data for 1,6-Hexanediol (7 total), please visit the HSDB record page.
독성 정보
Ecotoxicity Values
LC50; Species: Leuciscus idus (Ide); Conditions: static; Concentration: >1000 mg/L for 48 hr
EC50; Species: Daphnia magna (Water flea); Concentration: >500 mg/L for 24 and 48 hr; Effect: immobilization /Conditions of bioassay not specified in source examined/
EC50; Species: Scenedesmus subspicatus (Algae); Concentration: 2200 mg/L for 72 hr; Effect: growth inhibition, biomass /Conditions of bioassay not specified in source examined/
EC50; Species: Pseudomonas putida (Bacteria); Concentration: >10000 mg/L for 17 hr; Effect: cell multiplication inhibition /Conditions of bioassay not specified in source examined/
EC50; Species: Photobacterium phosphoreum (Bacteria); Concentration: 205 mg/L for 30 min; Effect: inhibition of light emission /Conditions of bioassay not specified in source examined/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 1,6-hexanediol is expected to have very high mobility in soil(SRC). Volatilization of 1,6-hexanediol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1,6-Hexanediol is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 5.0X10-4 mm Hg(4). Results of 91 to 98% biodegradation after 28 days using aqueous biodegradation screening tests(5), suggest biodegradation is an important 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 1,6-hexanediol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.2X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.76(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Results of 91 to 98% biodegrdation after 28 days using aqueous biodegradation screening tests(6), suggest biodegradation is an important fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,6-hexanediol, which has an extrapolated vapor pressure of 5.0X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,6-hexanediol 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 28 hrs(SRC), calculated from its estimated rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,6-Hexanediol 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).
Toxicity Summary
IDENTIFICATION AND USE: 1,6-Hexanediol is a solid. It is used as intermediate in the production of nylon; to make hexamethylenediamine, polyesters, polyurethanes; in gasoline refining; as plasticizer. HUMAN STUDIES: 1,6-Hexanediol induced no intermediate filament aggregation or cytotoxicity in human fibroblasts. Cytotoxic effects in chondrocytes and lymphocytes as well as genotoxic effects in lymphocytes were dose-dependent with threshold value of 5mg/mL showing no effects. ANIMAL STUDIES: An 80% aqueous preparation was not irritating to rabbit skin after up to 20 hr occlusive exposure. It was not lethal to 3 rabbits given 3,000 mg/kg bw by gavage. Two cats dosed once with 300 mg/kg bw by gavage survived, while 2 out of 4 animals receiving 1,000 mg/kg bw died. No signs of neurotoxicity or histopathological alteration of nervous tissue was observed with 1,6-hexanediol in rats. Male and female rats received 0, 100, 400 and 1,000 mg/kg body weight hexanediol by gavage for 4 (males) to 6 (females) weeks to screen the effect of hexanediol on reproduction and developmental toxicity. Marginal retarded body weight development in males at 1,000 mg/kg bw was the only effects noted in this study. Hexandiol was not mutagenic in the Ames test when Salmonella typhimurium strains (TA 98, TA 100, TA 1535 and TA 1537) were exposed up to 5,000 ug/plate with and without metabolic activation.
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/[USEPA; ICSS Dashboard Application; Available from, as of July 27, 2017: http://actor.epa.gov/dashboard/]
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,6-hexanediol can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,6-hexanediol is expected to have very high mobility in soil.
Human Toxicity Excerpts
/GENOTOXICITY/ Tissue engineering of autologous cartilage transplants is suggested as a new approach in reconstruction of external auricular deformities. 1,6-Hexanediol (HD), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 6-hydroxyhexanoic acid (HHA) are matrices of the open-pored polyurethane three-dimensional scaffold. Since these bioresorbable materials may interact with the human organism, cytotoxic effects on human chondrocytes and lymphocytes and genotoxic effects on human lymphocytes were monitored. Staining with propidium iodide and fluorescence diacetate as well as the EZ4U proliferation assay served for the detection of cytotoxic effects of the materials on human chondrocytes. Trypan blue staining was used to monitor cytotoxicity on lymphocytes. Genotoxic effects on lymphocytes in terms of strand breaks, alkali labile sites and incomplete excision repair were determined by the alkaline single cell microgel electrophoresis (Comet) assay. Cytotoxic effects in chondrocytes and lymphocytes as well as genotoxic effects in lymphocytes were dose-dependent with threshold values of 5 mg/mL HD, 0.5 mg/mL DBU and 0.03 mg/mL HHA showing no effects. These data suggest that these matrices could be safely used for scaffolds made of polyurethane unless these compounds are not released at a rate giving higher concentrations at the site of implantation or in body fluids, respectively.
/ALTERNATIVE and IN VITRO TESTS/ The effect of ... 1,6-hexanediol on the distribution of intermediate filaments in fibroblasts was studied. Skin fibroblasts from a normal 12 year old boy were cultured in minimum essential medium. Confluent cultures were exposed to medium containing 4, 8, or 16 mM 1,6-hexanediol. 1,6-Hexanediol induced no intermediate filament aggregation or cytotoxicity.
Artificial Pollution Sources
1,6-Hexanediol's production and use as an intermediate in the production of nylon, to make hexamethylenediamine, polyesters, polyurethans, in gasoline refining and as a plasticizer(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
AEROBIC: 1,6-Hexanediol, present at 20 mg dissolved organic carbon/L, reached between 91 and 98% of its theoretical CO2 evolution in 28 days using a modified Sturm test(1). Using a modified OECD screening test, 1,6-hexanediol reached between 94 and 96% dissolved organic carbon removal after 28 days(1). Therefore, this compound is expected to biodegrade rapidly under certain environmental conditions(SRC).
규제 정보
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Hexamethylene glycol is produced, as an intermediate or a final product, by process units covered under this subpart.
안전 데이터
- 자연 발화 온도
- 320 °C at 1.013 hPaAuto-flammability
화학 및 산업
약리 정보
Metabolism/Metabolites
There are no detailed studies with respect to toxicokinetics or metabolism. However, based on the structure and shown after oral application to rabbits, oxidation of both alcohol-groups resulting in the formation of adipic acid was observed.
용도 및 제조
Uses
Used as a solvent, an intermediate for nylon and polyesters, a coupling agent, a coal coating, a plasticizer, and in gasoline refining and the production of varnishes, adhesives, drugs, and textiles; [HSDB]
Textiles (Fiber & Fabric Manufacturing) [Category: Industry]
Solvent, intermediate for high polymers (nylon, polyesters), coupling agent, coil coating.
Intermediate in the production of nylon; to make hexamethylenediamine, polyesters, polyurethanes; in gasoline refining; as plasticizer.
Used as polyester or polyurethane component-increases flexibility, hydrolytic stability, and adhesion. It is used in polyesters for industrial coating applications, for example, can coatings, coil coatings for buildings and domestic appliances, two-component polyurethane coatings for automotive applications, car repair paints and stoving enamels. It is also used for production of macrodiols, for example, adipate esters and polycarbonate diols used in elastomers and polyurethane dispersions for parquet flooring and leather coatings. The diacrylate of HDO is employed as fast-curing reactive diluent in UV-curable coatings and has good solvency, adhesion and flexibility. HDO is applied in polyester polyols to produce polyurethane foams, elastomers, and adhesives. It is also used as chain extender in elastomers and in polymeric plasticizers. The diglycidyl ether of HDO is used as reactive diluent in epoxy systems.
A new approach is developed for hydrogenolytic ring opening of biobased 5-hydroxymethylfurfural (HMF), dehydration product of hexoses, towards 1,6-hexanediol (HDO) under atmospheric pressure. The highest yield of HDO, 43%, is achieved over reusable Pd/zirconium phosphate (ZrP) catalyst at 413 K in the presence of formic acid as hydrogen source. In comparison with various Bronsted and/or Lewis acidic supports, the specific Bronsted acidity on ZrP support effectively accelerated the cleavage of C-O bond in a furan ring.
U.S. Production
2023: 10,000,000 - <50,000,000 lb
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#6026]
1,6-Hexanediol 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).
Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,6-Hexanediol. National Production Volume: 38,657,980 lb/yr.
Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,6-Hexanediol:
Methods of Manufacturing
1,6-Hexanediol is produced industrially by the catalytic hydrogenation of adipic acid or of its esters. Mixtures of dicarboxylic acids and hydroxycarboxylic acids with C6 components formed in other processes (e.g., in cyclohexane oxidation) also can be used. Esterification of "distillation heavies" with lower alcohols is ofter carried out before hydrogenation.
Hydrogenation of dimethyl adipate over Raney-promoted copper chromite at 200 °C and 10 MPa produces 1,6-hexanediol.
Formulations/Preparations
... Pure product is about 98%.
>96% purity
Use Classification
EPA Safer Chemical Functional Use Classes -> Solvents
Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern
General Manufacturing Information
Transportation Equipment Manufacturing
1,6-Hexanediol: ACTIVE
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