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Butylcyclohexylphthalat

Butyl cyclohexyl phthalate

HCID 6779
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Grundinformationen

CAS
84-64-0
Standard-SMILES
CCCCOC(=O)c1ccccc1C(=O)OC1CCCCC1
InChIKey
BHKLONWXRPJNAE-UHFFFAOYSA-N
Summenformel
C18H24O4
Durchschnittliche Molmasse
304,4 g/mol
Monoisotopische Masse
304,16745924

Überblick

Butyl cyclohexyl phthalate is a clear brown slightly viscous liquid with a very mild odor. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Butyl cyclohexyl phthalate
IUPAC
1-O-butyl 2-O-cyclohexyl benzene-1,2-dicarboxylate
Lokaler Name
Butylcyclohexylphthalat
Englischer Name
Butyl cyclohexyl phthalate
Summenformel
C18H24O4
Molmasse
304.38

Namen und Synonyme

BUTYL CYCLOHEXYL PHTHALATECyclohexyl butyl phthalate1,2-Benzenedicarboxylic acid, butyl cyclohexyl esterPhthalic acid, butyl cyclohexyl esterCCRIS 6189HSDB 44881-O-butyl 2-O-cyclohexyl benzene-1,2-dicarboxylateEINECS 201-548-5NSC 69994Elastex 50BUNII-BI70L704B7BI70L704B7
Weitere Namen anzeigen
cyclohexylbutylphthalateN-BUTYL-CYCLOHEXYLPHTHALATECyclohexyl n-butyl phthalatephthalicacid,butylcyclohexylesterButyl cyclohexyl phthalate SolutionButyl Cyclohexyl Phthalate (Tech Mix)
NSC-699941-Butyl 2-cyclohexyl phthalateDTXSID50246891,2-Benzenedicarboxylic acid, 1-butyl 2-cyclohexyl esterBUTYL CYCLOHEXYL PHTHALATE [HSDB]RefChem:1222411-butyl 2-cyclohexyl benzene-1,2-dicarboxylateButyl cyclohexyl phthalic acid

Datenbank-Bezeichner

CAS
84-64-0

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,3
Polarare Oberfläche (TPSA)
52,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
8
Schwere Atome
22
Formalladung
0
Komplexität
360

Experimentelle und physikochemische Eigenschaften

PolymersPlastics & Rubber -> Phthalate Esters
SpringerMaterials PropertiesBoiling point
OdorVery mild odor
Density · 2 Einträge

1.078 (NTP, 1992) - Denser than water; will sink

1.076 at 25 °C

Color/Form · 2 Einträge

Colorless liquid

Clear liquid

Solubility · 3 Einträge

Insoluble (<1 mg/ml at 68 °F) (NTP, 1992)

Phthalate esters are soluble to various extents in many common organic solvents and oils, but have a relatively low solubility in water. /Phthalate esters/

Miscible with most organic solvents

Flash Pointgreater than 200 °F (NTP, 1992)
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point189-222 °C at 5 mm Hg

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationChemical: 1,2-Benzenedicarboxylic acid, butyl cyclohexyl ester
Other Safety InformationIMAP assessments - Phthalate esters: Environment tier II assessment
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Fire PotentialCombustible.
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the eyes, nose and mucous membranes.
Hazards SummarySee PHTHALATE ESTERS.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special Reports · 4 Einträge

USEPA; Ambient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067

Woodward KN (ed); Phthalate Esters: Toxicity and Metabolism (1988)

Phthalate Esters; Environ Health Perspect 45: 1-210 (1982)

USEPA/ECAO; Atlas Document for: Phthalate Esters (1980)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Phthalate esters are first hydrolyzed to their monoester derivative. Once formed, the monoester derivative can be further hydrolyzed in vivo to phthalic acid or conjugated to glucuronide, both of which can then be excreted. The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. The monoester and oxidative metabolites are excreted in the urine and faeces. (A2884)

Verwendung und Herstellung

Uses · 4 Einträge

Used as plasticizer for polymers, elastomers, and nitrocellulose lacquers; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Plasticizer for polymers and elastomers; nitrocellulose lacquers.

Phthalate esters are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are used in a variety of household applications such as shower curtains, vinyl upholstery, adhesives, floor tiles, food containers and wrappers, and cleaning materials. Personal care items containing phthalates include perfume, eye shadow, moisturizer, nail polish, liquid soap, and hair spray. (L1903)

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4946]
General Manufacturing Information · 2 Einträge

1,2-Benzenedicarboxylic acid, 1-butyl 2-cyclohexyl ester: ACTIVE

The first step, alcoholysis of phthalic anhydride (PA) to give the monoester, is rapid and goes to completion. The reaction generally starts at elevated temperatures and proceeds exothermically. The second step is the conversion of the monoester to a diester with the formation of water. This is a reversible reaction and proceeds more slowly than the first, thus determining the overall rate of reaction. To shift the equilibrium towards the diester, the water of reaction is removed by distillation. The rate of reaction can be influenced by the choice of catalyst and the reaction temperature. For fast conversion rates, high reaction temperatures are generally used. However, these are influenced by the boiling point of the alcohol and/or the type of catalyst. ... Currently, nearly all major phthalate producers use amphoteric catalysts for the esterification of high boiling alcohols. ... The reaction temperatures for the amphoteric catalysts are about 200 °C. At this temperature side reactions are minimized, and the alcohol can be recycled without purification. By using this type of catalyst, over 99.5 % conversion to diester can be achieved. /Phthalates/

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PubChem CID
6779
DTXSID
DTXSID5024689
UNII
BI70L704B7
EC Number
201-548-5
Nikkaji
J192.617I
Physical Description · 2 Einträge

Butyl cyclohexyl phthalate is a clear brown slightly viscous liquid with a very mild odor. (NTP, 1992)

Insoluble in water (0.28 mg/L at 25 deg C); [ChemIDplus] Clear liquid; [HSDB] Clear brown liquid; [CAMEO]

Other Experimental Properties · 3 Einträge

Saponification number 369; acidity (as phthalic acid) 0.01% max

Phthalate esters would be expected to have UV maxima in the 230 nm and 270 nm regions. /Phthalate esters/

... Resistance to migration from polymers, low temperature flexibility ... compatibility with polar polymers and additives over a wide range of compositions. /Phthalate esters/

Physikochemische Eigenschaften

Schmelzpunkt
25 °C · 25°C
Siedepunkt
405.2 °C · 405.2°C (rough estimate)
Dichte
1.1027 · 1.1027 (rough estimate)
Brechungsindex
1.54 · 1.5400 (estimate)
storage temp.
Sealed in dry,Room Temperature
Löslichkeit
Chloroform (Slightly), Ethyl Acetate (Slightly)
Aggregatzustand
Oil
Farbe
Clear Colourless
Henry's Law Constant
1 · 1.0×101 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Stable. Hydrolyzes under low or high pH conditions. Incompatible with strong oxidizing agents.
EPA chemische Informationen
Butyl cyclohexyl phthalate (84-64-0)
TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Butyl cyclohexyl phthalate is included on this list. Effective date 10/04/82; Sunset date 10/04/92.

Reactivity Profile · 1 Eintrag

An ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Air and Water ReactionsInsoluble in water. This compound will hydrolyze under high or low pH conditions. (NTP, 1992).

Sicherheit und Schutzausrüstung

Fire FightingFires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 Eintrag

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.

Preventive Measures · 1 Eintrag

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Personal Protective Equipment (PPE) · 1 Eintrag

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxikologische Informationen

Health Effects · 1 Eintrag

Phthalate esters are endocrine disruptors. Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility. The combination of effects associated with phthalates is called 'phthalate syndrome’. (A2883)

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5,100(SRC), determined from a structure estimation method(2), indicates that butyl cyclohexyl phthalate is expected to be immobile in soil(SRC). Volatilization of butyl cyclohexyl phthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.5X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Butyl cyclohexyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.77X10-6 mm Hg(4). Biodegradation data for butyl cyclohexyl phthalate were not available(SRC, 2008). However, by analogy to dicyclohexylphthalate which reached 68.5% of its theoretical BOD in the Japanese MITI test(5), butylcyclohexyl phthalate may be subject to biodegradation in the environment(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5100(SRC), determined from a structure estimation method(2), indicates that butyl cyclohexyl phthalate is 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 9.5X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 2900(SRC), from an estimated log Kow of 5.41(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(8). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 5.3 years and 190 days at pHs 7 and 8, respectively(9). Biodegradation data for butyl cyclohexyl phthalate were not available(SRC, 2008). However, by analogy to dicyclohexylphthalate which reached 68.5% of its theoretical BOD in the Japanese MITI test(10), butylcyclohexyl phthalate may be subject to biodegradation in the environment(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butyl cyclohexyl phthalate, which has a vapor pressure of 4.77X10-6 mm Hg at 25deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase butyl cyclohexyl phthalate 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). Particulate-phase butyl cyclohexyl phthalate may be removed from the air by wet or dry deposition(SRC). Butyl cyclohexyl phthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesOral (L1903) ; inhalation (L1903) ; dermal (L1903)
Toxicity Summary · 1 Eintrag

Phthalate esters are endocrine disruptors. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Some phthalates have also been shown to reduce the expression of insulin-like peptide 3 (insl3), an important hormone secreted by the Leydig cell necessary for development of the gubernacular ligament. Animal studies have shown that these effects disrupt reproductive development and can cause a number of malformations in affected young. (A2883)

Signs and SymptomsPhthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (A2883)
Ongoing Test Status · 1 Eintrag

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=84-64-0][Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=84-64-0]

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc of butyl cyclohexyl phthalate can be estimated to be 5,100(SRC). According to a classification scheme(2), this estimated Koc value suggests that butyl cyclohexyl phthalate is expected to be immobile in soil.

Artificial Pollution SourcesButyl cyclohexyl phthalate's production and use as a plasticizer(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

AEROBIC: Biodegradation data for butyl cyclohexyl phthalate were not available(SRC, 2008). However, by analogy to dicyclohexylphthalate which when present at 100 mg/L reached 68.5% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1), butylcyclohexyl phthalate may be subject to biodegradation in the environment(SRC).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 2,900 was calculated in fish for butyl cyclohexyl phthalate(SRC), using an estimated log Kow of 5.41(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(4).

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Butyl cyclohexyl phthalate is included on this list. Effective date 10/04/82; Sunset date 10/04/92.

Sicherheitsdaten

tsca
TSCA listed
Giftige Stoffe Daten
84-64-0(Hazardous Substances Data)

Anwendungen

VerwendenCyclohexyl Butyl Phthalate is an phthalate ester derivative that exhibits potential estrogenic activities.

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