Identification and Related Records
- 【Name】
- Dodecylbenzenesulfonic Acid
- 【Registry number】
- 27176-87-0 (CAS DataBase Reference)
- 【Synonyms】
-
n-Dodecylbenzenesulfonic acid
Dodecylbenzensulfonic acid (soft type)
LABSA
LINEAR ALKYL BENZENE
Linear alkylbenzenesulfonic acid
- 【EINECS(EC#)】
- 248-289-4
- 【Molecular Formula】
- C18H30O3S (Products with the same molecular formula)
- 【Molecular Weight】
- 348.47583
- 【Inchi】
- InChI=1S/C18H30O3S.Na/c1-2-3-4-5-6-7-8-9-10-11-14-17-15-12-13-16-18(17)22(19,20)21;/h12-13,15-16H,2-11,14H2,1H3,(H,19,20,21);/q;+1/p-1
- 【InChIKey】
- HFQQZARZPUDIFP-UHFFFAOYSA-M
- 【Canonical SMILES】
- CCCCCCCCCCCCC1=CC=CC=C1S(=O)(=O)[O-].[Na+]
Chemical and Physical Properties
- 【Appearance】
- brown or tan solid
- 【Density】
- 1.2
- 【Melting Point】
- 10℃
- 【Boiling Point】
- 315℃
- 【Refractive Index】
- n20/D 1.51
- 【Flash Point】
- 85 °F
- 【Water】
- soluble in water, alcohols, glycol ethers, glycols, esters, ketones, aromatic and aliphatic hydrocarbons
- 【Solubilities】
- soluble in water, alcohols, glycol ethers, glycols, esters, ketones, aromatic and aliphatic hydrocarbons
- 【Color/Form】
- White to light yellow flakes, granules, or powder
- 【Stability】
- Stable. Hygroscopic. Incompatible with bases, oxidizing agents, metals.
- 【Storage temp】
- Store in a cool, dry place. Keep container closed when not in use. Keep from contact with oxidizing materials. Keep away from metals. Corrosives area. Do not store near alkaline substances.
- 【Computed Properties】
- Molecular Weight:348.47583 [g/mol]
Molecular Formula:C18H29NaO3S
H-Bond Donor:0
H-Bond Acceptor:3
Rotatable Bond Count:12
Exact Mass:348.17351
MonoIsotopic Mass:348.17351
Topological Polar Surface Area:65.6
Heavy Atom Count:23
Formal Charge:0
Complexity:365
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2
Safety and Handling
- 【Hazard Codes】
- C:Corrosive
- 【Risk Statements】
- R10;R22;R34
- 【Safety Statements 】
- S16;S26;S36/37/39;S45
- 【HazardClass】
- 8
- 【Safety】
-
Safety Information about?Laurylbenzenesulfonic acid of (CAS NO.27176-87-0):
Hazard Codes:?
C
Risk Statements: 34-22-10?
R10: Flammable.?
R22: Harmful if swallowed.?
R34: Causes burns.
Safety Statements: 26-36/37/39-45-16
S16: Keep away from sources of ignition.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2924 3/PG 3
WGK Germany: 2
RTECS? DB6600000
HazardClass: 8
PackingGroup: III
Moderately toxic by ingestion. A corrosive. When heated to decomposition it emits toxic vapors of SOx.
- 【PackingGroup 】
- III
- 【Skin, Eye, and Respiratory Irritations】
- May cause skin irritation.
- 【Cleanup Methods】
- Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Water spill: If dissolved, apply activated carbon at ten times the spilled amount in region of 10 ppm or greater concentration. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
- 【Transport】
- UN 2584/2924
- 【Formulations/Preparations】
- VET: AS WETTING AGENT OR DETERGENT IN INSECTICIDAL DIPS FOR DOGS (0.2-0.5% IN FINAL DILUTION) & WITH SANITIZERS FOR POULTRY DRINKING WATER (30 MG/GAL), WASHING EGGS (150 MG/GAL), & ON PREMISES & EQUIPMENT (300 MG/GAL).
81% PURE, 13% SODIUM SULFATE
Grades of purity: 40% water; varies with manufacturer and use.
ARYLAN SBC
C 550
CONOCO C 550
CONOCO C-50
CONOCO C-60
CONOCO SD 40
DETERLON
ELFAN WA POWDER
F 90
HS 85S
KB
KB (SURFACTANT)
MARANIL
MARLON 375
MARLON A
MARLON A 350
MARLON A 375
MERPISAP AP 90P
NACCONOL 35SL
NANSA HS 80
NANSA HS 85S
NANSA SL
NANSA SS
NEOPELEX 05
PELOPON A
RICHONATE 1850
SANDET 60
SANTOMERSE ME
SINNOZON
SIPONATE DS 10
STEINARYL NKS 50
STEPAN DS 60
SULFRAMIN 1240
SULFRAMIN 85
SULFURIL 50
TREPOLATE F 40
TREPOLATE F 95
ULTRAWET 99LS
ULTRAWET 1T
X 2073
- 【Reactivities and Incompatibilities】
- ... ON CONTACT WITH ACID OR ACID FUMES, THEY EMIT HIGHLY TOXIC FUMES OF SO(X). /SULFONATES/
- 【Other Preventative Measures】
- If material not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Personnel protection: Avoid breathing vapors, or dusts. Keep upwind. Wash away any material which may have contacted the body with copious amounts of soap and water.
- 【Protective Equipment and Clothing】
- Rubber gloves, safety glasses.
Personnel protection: Wear appropriate chemical boots, protective gloves, and goggles.
- 【Specification】
-
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use foam, dry chemical, or carbon dioxide.?
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Do not ingest or inhale. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container. Corrosives area.
- 【Octanol/Water Partition Coefficient】
- log Kow = 0.45
- 【Report】
-
Reported in EPA TSCA Inventory.
- 【Disposal Methods】
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
- 【Use and Manufacturing】
- Methods of Manufacturing
REACTION OF A MIXTURE OF MONOCHLOROPARAFFINS HAVING PREDOMINANTLY TWELVE CARBON CHAIN LENGTHS WITH BENZENE IN THE PRESENCE OF AN ALUMINUM CHLORIDE CATALYST, FOLLOWED BY SULFONATION WITH SULFURIC ACID OR SULFUR TRIOXIDE & REACTION WITH SODIUM HYDROXIDE
BENZENE IS ALKYLATED WITH DODECENE, TO WHICH IT ATTACHES ITSELF IN ANY SECONDARY POSITION. RESULTING DODECYLBENZENE IS SULFONATED WITH SULFURIC ACID ... FOR LINEAR ALKYL SULFONATE (STRAIGHT-CHAIN ALKYL), THE DODECENE MAY BE REMOVED FROM KEROSINE OR CRUDES BY MOLECULAR SIEVE, MAY BE FORMED BY ZIEGLER POLYMERIZATION OF ETHYLENE, OR BY CRACKING WAX PARAFFINS TO ALPHA-OLEFINS.U.S. Exports
(1984) 3.05X10+9 g /ALKYL BENZENE SULFONIC ACID AND SALTS/
(1974) NegligibleU.S. Imports
(1984) 4.54X10+9 g /ANIONIC SURFACE ACTIVE AGENTS/
(1974) NegligibleU.S. Production
(1972) 1.65X10+11 G
(1975) 1.51X10+11 G
(1984) 9.32X10+10 g
(1974) 364.1 Million lbs/year
2.34X10+8 kg (1992)Consumption Patterns
HEAVY DUTY POWDER DETERGENTS, 50%; HEAVY DUTY LIQUID DETERGENTS, 12%; LIGHT DUTY LIQUID DETERGENTS, 15%; MISCELLANEOUS HOUSEHOLD CLEANER, 5%; INDUSTRIAL, INSTITUTIONAL, COMMERICAL CLEANERS, 13%; INDUSTRIAL PROCESSES AND AGRICULTURAL, 5% (1981)
- 【Usage】
-
Used as an impregnation medium for detection of amino acids and dipeptides by use of thin layer chromatography. Surface active agent.
Biomedical Effects and Toxicity
- 【Biomedical Effects and Toxicity】
- LABELED SODIUM ALKYLBENZENESULFONATE AT CONCN CLOSE TO THOSE FOUND IN POLLUTED WATER WERE READILY ABSORBED BY CARPS. ROUTE OF ABSORPTION WAS GILL OR SKIN. THE BIOCONCENTRATION COEFFICIENTS CORRELATED WITH MOLECULAR STRUCTURES OF THE SURFACTANTS TESTED.
THE UPTAKE, TISSUE DISTRIBUTION, & ELIMINATION OF SODIUM LAURYLBENZENESULFONATE WERE INVESTIGATED IN CARP (CYPRINUS CARPIO). CONCN FACTORS FOR HEPATOPANCREAS & GALLBLADDER 30 & 9000 RESPECTIVELY. MAX WHOLE-BODY LEVELS WERE REACHED @ 24-72 HR. UPTAKE INCR WITH INCREASING WATER HARDNESS; SURVIVAL TIME DECR WITH INCR WATER HARDNESS.
UPTAKE IN TEST ORGANISMS (DAPHNIDS AND FATHEAD MINNOWS) , AS MEASURED BY (14)CARBON ACTIVITY, WAS FUNCTION OF CHAIN LENGTH & EXPOSURE CONCN. APPROX 100% CLEARANCE WITHIN 10 DAYS.
IN RATS, BLOOD LEVELS OF SODIUM-PARA-DODECYLBENZENESULFONATE WAS MAX @ 2 HR, NEGLIGIBLE @ 48 HR, WHILE EXCRETION RATE OF RADIOACTIVE LABEL WAS 99.4% AFTER 48 HR. /SODIUM PARA-DODECYLBENZENESULFONATE/
(14)C-labeled sodium dodecylbenzenesufonate (DBS) ... administered daily in the diet at a concn of 1.4 mg/kg to male rats for 5 weeks. ... From a total uptake of 1.213 + or - 0.08 mg/animal of DBS, 81.8% was excreted during the dosing period; 52.4% in feces and 29.4% in urine. Low levels of (14)C-DBS-derived residues were detected in all tissues analyzed on day 35 of the /study/. Following 1 week on normal diet only 7.8% of the nominally stored amount of (14)C was found in the excreta. Single injections of 0.385 mg (14)C DBS/rat 2.26 + or - 0.15 mg/kg body weight resulted in total elimination of 94.5% within 10 days. 84.7% of the dose was eliminated the first 24 hr. All (14)C DBS fecal and renal metabolites were ... highly polar. [Lay JP et al; Toxicol Lett 17 (1-2): 187-92 (1983)] PubMed Abstract
After single oral dose of /(35)S-labeled/ sodium dodecylbenzenesulfonate, rats excreted 64% and 24% of the dose in urine and feces, respectively. A similar study of repeated doses of /(14)C-labeled/ alkylbenzenesulfonate (mean molecular wt 349, a major constituent of detergents) to rhesus monkeys has shown that radioactivity did not accumulate in the tissues. /Aromatic, sulfur-containig cmpd/
(14)C-Labelled sodium dodecylbenzene sulfonate was administered daily in the diet at a concentration of 1.4 mg/kg to male rats for 5 weeks. From the total uptake (1.213 +/- 0.08 mg/animal) of sodium dodecylbenzene sulfonate, 81.8% was excreted during the dosing period; 52.4% in feces and 29.4% in urine. Low levels of (14)C sodium dodecylbenzene sulfonate derived residues were detected in all tissues analyzed on day 35 of the experiment. Following 1 week on normal diet only 7.8% of the nominally stored amount of (14)C was found in the excreta. Single ip application of 0.385 mg (14)C sodium dodecylbenzene sulfonate/rat (2.26 +/- 0.15 mg/kg body wt) resulted in a total elimination of 94.5% within 10 days. 84.7% of the dose was eliminated in the first 24 hr. All fecal and renal (14)C sodium dodecylbenzene sulfonate derived activity consisted of highly polar metabolites. [Lay JP et al; Toxicol Lett 17 (1-2): 187 (1983)] PubMed Abstract
Environmental Fate and Exposure Potential
- 【Environmental Fate/Exposure Summary】
- TERRESTRIAL FATE: Based on a recommended classification scheme(2), sodium dodecylbenzenesulfonate should have high mobility(SRC) in soil based on an estimated Koc value of 110.5(1,SRC). Biodegradation of sodium dodecylbenzenesulfonic acid is expected to be an important fate process for aerobic conditions based on a variety of biodegradation studies(5-20). Volatilization of sodium dodecylbenzenesulfonic acid is not expected from moist or dry soils based on an estimated vapor pressure of approximately 2.29X10-15 mm Hg at 25 deg C(3) and an estimated Henry's Law constant of 6.27X10-8 atm-cu m/mole(4).
AQUATIC FATE: Sodium dodecylbenzenesulfonate is expected to be essentially non-volatile from water(2) based upon an estimated Henry's Law constant of 6.27x10-8 atm cu m/mol(1,SRC). Biodegradation of sodium dodecylbenzenesulfonate is expected to be an important fate process for aerobic conditions based on a variety of biodegradation studies(3-18). Aquatic bioconcentration, adsorption to sediment, and hydrolysis are not expected to be important fate processes in aquatic environments(SRC).
ATMOSPHERIC FATE: Based on an estimated vapor pressure of approximately 2.29x10-15 mm Hg at 25 deg C(1), sodium dodecylbenzenesulfonate will exist in the atmosphere in the particulate phase(2). Removal of sodium dodecylbenzenesulfonate from the atmosphere can occur through wet deposition(SRC).
Aquatic: Water temperature affects biodegration. The rate of sodium-C12 linear alkylbenzene sulfonic acids biodegradation in Chesapeake Bay water was max at 25-30 deg C and decreased at lower incubation temperatures. /Sodium-C12 linear alkylbenzene sulfonic acids/
Terrestrial: The adsorption of sodium-C12 linear alkylbenzene sulfonic acids is affected by the type of soil. The affinity of the soil for surfactants competes with microbial attack, slowing biodegradation. /Sodium-C12 linear alkylbenzene sulfonic acids/
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