Dodecylbenzene

HCID 31237

Basic information

CAS
123-01-3
Standard SMILES
CCCCCCCCCCCCc1ccccc1
InChIKey
KWKXNDCHNDYVRT-UHFFFAOYSA-N
Molecular formula
C18H30
Average molar mass
246.4 g/mol
Monoisotopic mass
246.23475096

Overview

Dodecylbenzene is a colorless liquid with a weak oily odor. Floats on water. (USCG, 1999)

Names & identifiers

Preferred name
Dodecylbenzene
IUPAC
dodecylbenzene
English name
Dodecylbenzene
Molecular formula
C18H30
Molecular weight
246.43

Names & synonyms

DODECYLBENZENE123-01-31-Phenyldodecanen-DodecylbenzeneBenzene, dodecyl-LaurylbenzeneMarlicanDodecane, 1-phenyl-PhenyldodecanDodecylbenzene, crudeDTXSID7026994DTXCID706994
Show more names
AlkaneALKYLBENZENEAlkylate P 1alkylatep1nalkylene500Nalkylene 500
RefChem:135513204-591-8PhenyldodecaneDodecane, phenyl-1-dodecylbenzene29986-57-0MFCD00008974NSC 102805

Database identifiers

CAS
123-01-3、29986-57-0、68442-69-3
PubChem CID
31237
DTXSID
DTXSID7026994
ChEMBL
CHEMBL3187866
UNII
A2AX003680
EC Number
204-591-8
Nikkaji
J5.538G

Properties

Computed structural properties

XLogP
8.8
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
11
Heavy atoms
18

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aromatic Hydrocarbons
SpringerMaterials PropertiesBoiling point
LogPlog Kow= 8.26
OdorWEAK OILY ODOR
Density · 3 items

0.86 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8851 @ 20 °C/4 °C

Relative density (water = 1): 0.86

Color/FormCOLORLESS LIQUID

Physicochemical properties

Melting point
3 °C · 3 °C (lit.)
Boiling point
185 · 185-188 °C/15 mmHg (lit.) 331 °C (lit.)
Density
0.856 g/mL · 0.856 g/mL at 25 °C (lit.)
vapor pressure
0.1 hPa · 0.1 hPa (50 °C)
refractive index
20 · n20/D 1.482(lit.)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 46.9% (53 of 113) of reports.

Warning

H315 (17.7%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P273, P280, P302+P352, P321, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 113 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Benzene, dodecyl-

Benzene, dodecyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzene, dodecyl-: Human health tier I assessment
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible.

Fire PotentialCOMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.
Health HazardsLiquid causes mild irritation of eyes and may cause allergenic responses on repeated contact with skin. Ingestion causes nausea. (USCG, 1999)
Hazards SummaryA skin and eye irritant; [ICSC] Linear alkylbenzenes are not acutely toxic. [Reference #1] Oral LDLo (mouse) = 20,000 mg/kg; Effects in lethal dose studies include liver changes and EEG changes; [RTECS] A mild eye irritant; [MSDSonline]

Safety & protection

Fire Fighting · 2 items

Fire Extinguishing Agents Not to Be Used: Water may be ineffective.

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

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. Do NOT induce vomiting. Give one or two glasses of water to drink.

First Aid · 1 item

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.

Fire Fighting Procedures · 2 items

To fight fire, use foam, carbon dioxide, dry chemical.

WATER OR FOAM MAY CAUSE FROTHING. /DODECYL BENZENE (CRUDE)/

Storage Conditions · 1 item

IN GENERAL, MATERIALS...TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS...SHOULD BE STORED IN COOL...VENTILATED PLACE, OUT OF...SUN, AWAY FROM...FIRE HAZARD...BE PERIODICALLY INSPECTED & MONITORED. INCOMPATIBLE MATERIAL SHOULD BE ISOLATED...

Cleanup Methods...IT CAN BE SULFONATED IN WASTES & RECYCLED.

Toxicology

Interactions · 3 items

...OWING TO ITS SOLVENCY CHARACTERISTICS, IT MAY PROMOTE TUMORIGENIC & PROCARCINOGENIC POTENTIAL OF MATERIALS SUCH AS DIMETHYLBENZANTHRACENE.

ADULT RHESUS MONKEYS GIVEN 2 ML OF 1% 7,12-DMBA IN ACETONE PLUS 100% DDB 3 TIMES/WK FOR 6.5 YR & UV IRRADIATED FOR 5 MIN 3 TIMES/WK FOR 6.5 MO BEGINNING 1 MO AFTER DMBA & DDB SKIN TREATMENT. MULTIPLE SINGLE PAPILLOMAS, DERMAL MELANOSIS & BASAL CELL EPITHELIOMAS FOUND.

IN GALAGOS GIVEN 0.2 ML OF 7,12-DMBA (2.5% SOLN IN ACETONE) IMMEDIATELY FOLLOWED BY 0.5 ML DDB APPLIED TO SAME AREA OF SKIN 3 TIMES/WK FOR 9 WK FOLLOWED BY DMBA & 100% DDB 2 TIMES/WK FOR 4 YR, BENIGN TUMORS (KERATOACANTHOMAS & PIGMENTED PAPILLOMA) WERE OBSERVED.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7.4X10+5(SRC), determined from a log Kow of 8.26(2) and a regression-derived equation(3), indicates that dodecylbenzene is expected to be immobile in soil(SRC). Volatilization of dodecylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.13 atm-cu m/mole(SRC), using a fragment constant estimation method(4), but adsorption may severely attenuate this process. Dodecylbenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.1X10-5 mm Hg(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7.4X10+5(SRC), determined from a log Kow of 8.26(2) and a regression-derived equation(3), indicates that dodecylbenzene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4), but adsorption may severely attenuate this process(SRC). Volatilization half-lives for a model river and model lake are 4.5 hours and 6 days, respectively(SRC), using an estimation method(3) if adsorption is neglected. The estimated volatilization half-life from a model pond is 21 years if adsorption is considered(5). According to a classification scheme(6), a measured BCF value of 35(7) suggests that bioconcentration in aquatic organisms is moderate. River die-away tests have shown linear alkylbenzenes are readily biodegradable, with half-lives of 4.8 and 10.1 days for C-12 alkyl chain isomers in river water(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dodecylbenzene, which has a vapor pressure of 5.1X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dodecylbenzene 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 19 hours(SRC) from its estimated rate constant of 2X10-11 cu cm/molecule-sec at 25 °C(3). Particulate-phase dodecylbenzene may be removed from the air by wet and dry deposition(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 RoutesThe substance can be absorbed into the body by ingestion.
Signs and Symptoms · 4 items

Cough. Sore throat.

Redness.

Redness.

Nausea.

Effluent Concentrations · 1 item

Dodecylbenzene was detected in wastewater effluents in Tokyo, Japan at concns of 0.39-2.76 ng/l(1). Dodecylbenzene was detected in leachate from a surfactant manufacturing plant in Barcelona, Spain at concns of less than 0.5 ppm to 5 ppm(2).

Safety data

PPE
Eyeshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
CZ9540000
ridadr
UN 3082 9/PG 3
hs_code
29029030

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used to make linear alkylbenzenesulfonate surfactants, dodecylnitrobenzene, dodecylaniline, and dodecylbenzyl chloride; as vehicle and solvent for polynuclear aromatics in carcinogenesis studies; as solvent for organophosphorus insecticides; to make arylalkyl sulfonates in soap and detergent industry; [HSDB] Not produced in commercial quantity as pure substance, rather as mixtures of long-chain linear alkylbenzenes with alkyl group containing from 10 to 16 carbon atoms; The detergent surfactant LAS uses more than 98% of all linear alkylbenzenes; [eChemPortal: SIDSUNEP]

Farming (Pesticides) [Category: Industry]

CHEM INT FOR LINEAR ALKYLBENZENESULFONATE SURFACTANTS, DODECYLNITROBENZENE, DODECYLANILINE, DODECYLBENZYL CHLORIDE

AS VEHICLE & SOLVENT FOR POLYNUCLEAR AROMATICS IN CARCINOGENESIS STUDIES

SOLVENT FOR ORGANOPHOSPHORUS INSECTICIDES

USED TO PRODUCE ARYLALKYL SULFONATES IN SOAP & DETERGENT INDUSTRY; HAS BEEN APPLIED AS SOLVENT & CHEM VEHICLE

U.S. Exports(1975) 8.62X10+10 GRAMS
U.S. Imports · 2 items

(1972) NEGLIGIBLE

(1975) NEGLIGIBLE

U.S. Production · 2 items

(1972) 2.4X10+11 G (LINEAR ALKYLBENZENES)

(1975) 2.25X10+11 GRAMS

Consumption PatternsUSES OTHER THAN AS A CHEM INT FOR SULFONATES ARE BELIEVED TO CONSUME ONLY SMALL QUANTITIES (1975)
Methods of Manufacturing · 2 items

Alkylation of benzene with isomeric dodecenes, obtained by polymerization of propylene.

...BY ALKYLATION OF BENZENE WITH PROPYLENE TETRAMER...

Applications · 2 items

Usesn-Dodecylbenzene, is a precursor to sodium dodecylbenzenesulfonate, a surfactant that is a key ingredient of household laundry detergents, such as Tide. It is a widely used cleaner, dyeing assistant in textile industrial, degrease agent in electroplate, leather, de- inking agent in papering, rubber and plastic, break emulsion agent in oil industry, artesian well foaming agent in oil well.

General DescriptionDodecylbenzene is a colorless liquid with a weak oily odor. Floats on water. (USCG, 1999)

Preparation methods

Preparationn-Dodecylbenzene was prepared by lauroyl chloridation, Friedel-Crafts acylation and Huang Minglong deoxidization, followed by purification with vacuum distillation and recrystallization procedures.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

Related reactions

17 records

Compound notes

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