Basic information
- Standard SMILES
C1CCCCCCCCCCC1- InChIKey
DDTBPAQBQHZRDW-UHFFFAOYSA-N- Molecular formula
- C12H24
- Average molar mass
- 168.32 g/mol
- Monoisotopic mass
- 168.18780077
Overview
cyclododecane has been reported in Terminalia chebula with data available.
Names & identifiers
- Preferred name
- Cyclododecane
- IUPAC
- cyclododecane
- English name
- CYCLODODECANE
- Molecular formula
- C12H24
- Molecular weight
- 168.32
Names & synonyms
Show more names
Database identifiers
- CAS
294-62-2- PubChem CID
- 9268
- DTXSID
DTXSID9021552- ChEMBL
CHEMBL3185808- UNII
- 97CN13ZD83
- EC Number
- 206-033-9
- Nikkaji
- J43.296B
Properties
Computed structural properties
- XLogP
- 6.7
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 43
Experimental & physicochemical properties
Vapor Pressure
0.03 [mmHg]
0.0295 mm Hg at 25 °C
Physicochemical properties
- Melting point
- 59 · 59-61°C
- Boiling point
- 111 °C · 111 °C / 17mmHg
- Density
- 0.79 · 0.790
- vapor pressure
- 9.83 Pa · 9.83Pa at 20℃
- refractive index
- 1.486 · 1.4860 (estimate)
- Flash point
- 88 ℃ · 88℃
- storage temp.
- Sealed in dry,Room Temperature
- Appearance
- White to off-white Solid
- Water Solubility
- 16 μg/L · 16μg/L at 20℃
- Henry's Law Constant
- 6.4 · 6.4×10-6 mol/(m3Pa) at 25℃, HSDB (2015)
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- InChI
- InChI=1S/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2
- InChIKey
- DDTBPAQBQHZRDW-UHFFFAOYSA-N
- SMILES
- C1CCCCCCCCCCC1
- LogP
- 7.6 at · 7.6 at 25℃
- CAS DataBase Reference
- 294 · 294-62-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 97 CN13ZD83 · 97CN13ZD83
- EPA Substance Registry System
- Cyclododecane (294-62-2)
- Symbol(GHS)
- 7 · GHS07,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 413 · H413
- Precautionary statements
- 273 · P273-P501
- Safety Statements
- 24 · 24/25
- RIDADR
- 1325 · 1325
- RTECS
- 2295000 · GV2295000
- TSCA
- TSCA listed
- HazardClass
- 4.1 · 4.1
- PackingGroup
- III
- HS Code
- 29021990 · 29021990
- Hazardous Substances Data
- 294 · 294-62-2(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 75% (3 of 4) of all reports.
H413 (25%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Status: Active Update: 18-02-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/2097
Cyclododecane: Does not have an individual approval but may be used under an appropriate group standard
Safety & protection
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.
Toxicology
Body Burden
The expired air of 62 non-smoking humans was examined for the presence of environmental pollutants and other chemical constituents(1); cyclododecane was detected in the expired air of all three subject groups (diabetic, pre-diabetic and control)(1).
Ecotoxicity Values
EC50; Species: Daphnia pulex (Water flea, neaonate <24 hr old); Conditions: freshwater, static, 17 °C, hard water; Concentration: 21000 ug/L for 48 hr; Effect: intoxication, immobilization /> or =96% purity/
EC50; Species: Scenedesmus subspicatus (Algae); Concentration: >2.1 mg/L for 72 hr; Effect: No effects on biomass or growth rate were observed. The range of test concentrations was limited by the water solubility. /Conditions of bioassay not specified in source examined/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5,300(SRC), determined from a structure estimation method(2), indicates that cyclododecane is expected to be immobile(SRC). Volatilization of cyclododecane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.54 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Cyclododecane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). A 6% of theoretical BOD using activated sludge in the Japanese MITI test(5), suggests 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 5,300(SRC), determined from a structure estimation method(2), indicates that cyclododecane is 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 1.54 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 hours and 5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 9 years if adsorption is considered(5). According to a classification scheme(6), a BCF range of 1,100-14,400(7) suggests that bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). A 6% of theoretical BOD using activated sludge in the Japanese MITI test(7), suggests 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), cyclododecane, which has an estimated vapor pressure of 0.029 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyclododecane 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 23 hours(SRC), calculated from its rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Cyclododecane 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).
Ecotoxicity Excerpts
/AQUATIC SPECIES/ We have provided a hazard ranking for 19 classes of compounds representing many of the nearly 500 organic compounds identified by gas chromatography-mass spectrometry in lake trout (Salvelinus namaycush) and walleye (Stizostedion vitreum vitreum) from the Great Lakes and Lake St. Clair. We initially made a provisional hazard ranking based on available published and unpublished information on aquatic toxicity, bioaccumulation, occurrence and sources. Acute toxicity tests with Daphnia pulex at 17 °C in reconstituted hard water were performed with 30 compounds representative of the 19 classes that were highest in the provisional ranking. The resulting toxicity data, along with information on the compounds' occurrence in Great Lakes fish and their sources, were ranked and weighted and then used in calculating the revised hazard ranking. The 10 most hazardous classes, in descending order, are as follows (values shown are mean 48-hr EC50s, in ug/mL): arene halides (e.g., polychlorinated biphenyls, DDT), 0.0011; phthalate esters, 0.133; chlorinated camphenes (toxaphene), 0.0082; polyaromatic hydrocarbons (PAHs; e.g., dimethyl-naphthalene) and reduced derivatives, 1.01; chlorinated fused polycyclics (e.g., trans-nonachlor), 0.022; nitrogen-containing compounds (e.g., O-methylhydroxylamine), 1.35; alkyl halides (e.g., (bromomethyl)cyclohexene), 10.1; cyclic alkanes (e.g., cyclododecane), 20.9; silicon-containing compounds (e.g., dimethyldiethoxy silane), 1.25; and heterocyclic nitrogen compounds (e.g., nicotine), 2.48. We recommend that chronic bioassays be conducted with fish and invertebrates to determine the sublethal effects of the following classes of compounds, for which few toxicity data are available: PAHs, heterocyclic nitrogen compounds, other nitrogen-containing compounds, alkyl halides, cyclic alkanes and silicon-containing compounds. Information from these types of studies will aid researchers in determining the possible causal role these contaminants play in the decline and reproductive impairment of Great Lakes fish.
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of cyclododecane can be estimated to be 5,300(SRC). According to a classification scheme(2), this estimated Koc value suggests that cyclododecane is expected to be immobile in soil.
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Cyclooctane and other volatile cycloalkanes are CNS depressants and have been identified as aspiration hazards.
/OTHER TOXICITY INFORMATION/ Cyclododecane is not a skin irritant.
Environmental Bioconcentration
A BCF range of 1,100-11,1000 and 1,800-14,400 was measured in fish for cyclododecane using a test chemical concentration of 30 and carp (Cyprinus carpio) which were exposed over an 10-week period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).
Volatilization from Water/Soil
The Henry's Law constant for cyclododecane is estimated as 1.54 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that cyclododecane is expected to volatilize rapidly 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 4 hours(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 5 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 9 years if adsorption is considered. Cyclododecane's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Cyclododecane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.029 mm Hg(SRC), determined from a fragment constant method(4).
Safety data
- tsca
- TSCA listed
- rtecs
- GV2295000
- ridadr
- 1325
- hs_code
- 29021990
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08,GHS09
- safety_code
- 24/25
- hazard_class
- 4.1
- packing_group
- III
- Hazard statements
- H413
- REACH Registrations
- Active
- Precautionary statements
- P273-P501
- Hazardous Substances Data
- 294-62-2(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as an intermediate for the production of chemicals to make polyamides, polyesters, synthetic lubricating oils, and nylon 12; as a high-purity solvent; as a mothproofing agent; [HSDB]
Intermediate for the production of chemicals used to make polyamides, polyesters, synthetic lubricating oils, and nylon 12; high-purity solvent. Also used as a moth proofing agent
An intermediate for the production of nylon 12
U.S. Production
Cyclododecane 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. [Table#5435]
Methods of Manufacturing
Cyclododecane is produced by liquid-phase hydrogenation of 1,5,9-cyclododecatriene over nickel catalysts.
Cyclododecane ... is obtained by catalytic hydrogenation of 1,5,9-cyclododecatriene.
General Manufacturing Information
Cyclododecane: ACTIVE
THE SUBLIMATING COMPOUND CYCLODODECANE CAN BE EMULSIFIED IN WATER IN THE PRESENCE OF SURFACTANTS. THE EMULSION CAN BE USED TO EMULSIFY PESTICIDES.
Applications
UsesCyclododecane is considered as a new product in the conservation industry that is utilized as a temporary fixative, consolidant, barrier layer, and masking material in numerous fields of specialization. As a consolidant, it protects fragile ceramics while moving; therefore, allowing packaging and handling without any damage. As a temporary adhesive, cyclododecane has also been used remove subsequent of an adhesive without causing any damage. Its film-forming properties are one of the desirable working characteristics. The compound has been employed as a fixative for moisture-sensitive media on paper in the process of aqueous treatment. Due to its non-polar quality, cyclododecane can be used to protect materials that are solvent-sensitive during local solvent treatment. At room temperature, cyclododecane has the ability form a typically rigid solid, therefore, it has been used to secure friable substrates or flaking paint during transportation or during cleaning in surrounding. Moreover, it has been used to isolate the surface of an object when making mold.
UsesCyclooctane and cyclononane are used as starting materials for organic synthesis. The major use of cyclododecane is as an intermediate for the production of chemicals used to make polyamides, polyesters, synthetic lubricating oils, and nylon 12; it is also used as a high-purity solvent. An emulsion of cyclododecane can be used to emulsify pesticides. It is also used as a mothproofing agent.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
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