Dodecylbenzenesulphonic acid

• CAS: 27176-87-0
• Catalog Number: ACM27176870-1
• Category: Main Products
• Molecular Weight: 326.49
• Molecular Formula: C18H30O3S
• Description: Dodecylbenzenesulfonic acid is a colorless liquid. It is soluble in water. It is corrosive to metals and tissue. It is used to make detergents.;Liquid;YELLOW-TO-BROWN LIQUID.
• Synonyms: Dodecylbenzenesulfonic A
• IUPAC Name: 2-Dodecylbenzenesulfonic acid
• Canonical SMILES: CCCCCCCCCCCCC1=CC=CC=C1S(=O)(=O)O
• InChI: WBIQQQGBSDOWNP-UHFFFAOYSA-N
• InChI Key: InChI=1S/C18H30O3S/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)
• Boiling Point: 82 °C
• Melting Point: 10 °C
• Flash Point: 300 °F (USCG, 1999);300 °F open cup;148.9 °C o.c.
• Density: 1.06g/ml
• Solubility: Solubility in water: very good
• Appearance: Brown viscous liquid
• Active Content: 95%
• Color/Form: Light yellow to brown
• Complexity: 359
• Corrosivity: Dodecylbenzenesulfonic acid is corrosive to metals.
• Covalently-Bonded Unit Count: 1
• Decomposition: >204.5 °C
• Defined Atom Stereocenter Count: 0
• EC Number: 248-289-4
• Exact Mass: 326.19156599
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Heavy Atom Count: 22
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• ICSC Number: 1470
• Monoisotopic Mass: 326.19156599
• Physical State: Solid
• Rotatable Bond Count: 12
• Topological Polar Surface Area: 62.8 Ų
• UNII: QMO4A07H35
• UN Number: 2584;2586;2584
• XLogP3: 6.9

Case Study

Study of asphaltene destabilization in the presence of dodecylbenzenesulfonic acid

Huffman, Mitchell, and H. Scott Fogler. Fuel 304 (2021): 121320.

Asphaltenes are molecules in crude oil that can be dissolved in aromatic solvents such as toluene but precipitate in the presence of n-alkanes such as heptane. There are a large number of different molecules in crude oil that are classified as asphaltenes. The effect of amphiphilic head groups on asphaltene destabilization and aggregation was investigated. The experimental results showed that dodecylphenol (DDCP) delayed asphaltene aggregation in all 3 crude oils studied. On the other hand, dodecylbenzenesulfonic acid (DBSA) delayed the detection of asphaltene aggregation in two crude oils and accelerated it in one crude oil. In this study, the effect of polar head groups on additives was investigated using two compounds: dodecylbenzenesulfonic acid (DBSA) and dodecylphenol (DDCP). These two compounds have the same tail, but different functional groups.
In studying the effect of amphiphilic additives on asphaltene aggregation kinetics, dodecylbenzenesulfonic acid (DBSA) or dodecylphenol (DDCP) was added to crude oil. To prepare the oil-amphiphile mixture, the volume of oil required for the experiment was added to a glass bottle with a headspace smaller than the volume of oil in it. The necessary volume of amphiphile was added to the oil using a microdispenser to achieve a concentration of 0.000425 mol of amphiphile per gram of asphaltene in the mixture (grams of additive per liter of oil equivalent are shown in Table 2). The oil-amphiphile mixture was stirred at 200 rpm for 12 hours at room temperature (22°C) using an orbital shaker. After stirring for 12 hours, the mixture was used for detection time, centrifugation, and sedimentation experiments.

Liquid crystal phases formed by linear dodecylbenzenesulfonic acid

Ramaraju, S. M., et al. Colloids and Surfaces A: Physicochemical and Engineering Aspects 288.1-3 (2006): 77-85.

The liquid crystals and other phases formed when dodecylbenzenesulfonic acid (DBSA) was "dry neutralized" with sodium carbonate to form sodium dodecylbenzenesulfonate (NaDBS) were studied using optical microscopy, X-ray diffraction, and differential scanning calorimetry. In addition, the phases formed by DBSA with water were studied using the same methods. For the DBSA/water system, the surfactant-rich and water-rich samples formed liquid phases, while lamellar phases appeared in an intermediate composition range of about 100%. Fully neutralized NaDBS is a soft solid that contains at least three different intermediate phase structures, probably lamellar, at ambient temperature. These phases exist to ca. 80% neutralization and merge into a single phase above about 40%. Several low-intensity, high-angle X-ray reflections were also observed at low temperatures, implying that at least one of the phases has more order than the simple lamellar phase.
Stoichiometric proportions of solid sodium carbonate powder were added to DBSA in a closed container to achieve the desired degree of neutralization after the above reaction. This results in the formation of a viscous paste with a lot of foam, which requires further shearing to ensure the reaction is complete. Determining the endpoint of neutralization is not easy. To estimate the stoichiometric weights of reactants to be added, the average molecular weight of the DBSA isomers can be used. However, there is additional sulfuric acid present as an impurity, as well as undetermined organic matter. Therefore, the DBSA is titrated with sodium carbonate solution to determine the final endpoint, which gives an effective molecular weight of 324.3.

Study of dodecylbenzenesulfonic acid (DBSA) as a bitumen modifier

Ortega, Francisco J., Francisco J. Navarro, and Moisés García-Morales. Energy & Fuels 31.5 (2017): 5003-5010.

Traditionally, bitumen degradation is addressed by modification with polymers, but sometimes unstable mixtures are produced due to the lack of affinity between them. A new and different approach based on the use of dodecylbenzenesulfonic acid (DBSA) is reported. DSBA is a surfactant containing strong acid groups capable of interacting with asphaltene molecules and is commonly used as a dispersant for asphaltenes in crude oil. However, the opposite effect can also be obtained as long as the critical concentration is not exceeded. In this paper, the effects of additive concentration and processing temperature on the thermomechanical behavior of DBSA-modified bitumen were evaluated by rheological, thermal and thermogravimetric analysis. Within the concentration range used (0.4 to 3 wt.%), the binding of DBSA to asphaltene molecules
promoted the binding of asphaltene molecules/aggregates into larger clusters in bitumen, and 3 wt.% dodecylbenzenesulfonic acid (DBSA) significantly improved the rheological properties of bitumen. The asphaltene fractions in pure bitumen and bitumen modified with 3 wt.% DBSA were obtained by precipitation and centrifugation following the following steps. The bitumen was first dissolved in n-heptane (1 g/20 mL) in a conical flask and heated under reflux for 1 h. Then, the solution was cooled to room temperature under ambient conditions and then centrifuged at 3000 rpm for 5 min. The supernatant was removed and the precipitate (asphaltenes) was washed by resuspension and centrifugation again until the supernatant was clear enough. Finally, the asphaltenes were dried and placed in a glass flask.

Molecular dynamics simulation of the molecular mechanism of asphaltene inhibition by dodecylbenzenesulfonic acid

Jiang, Bin, et al. Energy & Fuels 33.6 (2019): 5067-5080.

The behavior of the asphaltene model compound N-(1-undecyldodecyl)-N'-(5-carboxypentyl)-perylene-3,4,9,10-tetracarboxybisimide (C5PeC11) in n-heptane and toluene solutions in the absence and presence of the asphaltene inhibitor dodecylbenzenesulfonic acid (DBSA) was studied using molecular dynamics (MD) simulations. It was found that the presence of DBSA reduced the rate and extent of C5PeC11 aggregation while increasing the solvation of C5PeC11 molecules in the studied solvents. The higher the concentration of DBSA molecules, the better the dispersion of C5PeC11 molecules. It was found that core-core stacking between PAH cores is the main driving force for C5PeC11 aggregation, while the association between polar groups is a factor that enhances aggregation. Adding DBSA molecules after the C5PeC11 aggregates can destroy the hydrogen bonds between C5PeC11 molecules in the aggregates and weaken the C5PeC11 aggregates. Due to the interaction between DBSA and C5PeC11 and the self-association of DBSA molecules, a protective shell of DBSA molecules is formed around the C5PeC11 aggregates, which is beneficial to inhibit the flocculation of C5PeC11 aggregates.
The simulation box was constructed by first placing the required number of C5PeC11 molecules in a cubic box with a side length of 12 nm. Three-dimensional periodic boundary conditions were used in the MD simulation to avoid problems related to the limited size of the simulation box, making the simulation system more like the real system. Different numbers of DBSA molecules were added at different times to achieve different simulation purposes. The box was then solvated with n-heptane and toluene molecules and then energy minimized. A total of five simulation boxes were constructed. These systems represent high concentrations (about 30 g/L) of asphaltene to ensure the formation of nanoaggregates. After the simulation, the structural and dynamic characteristics of the system were analyzed using the GROMACS built-in analysis tools.

Custom Q&A

What is the molecular formula of dodecylbenzenesulphonic acid?

The molecular formula of dodecylbenzenesulphonic acid is C18H30O3S.

What is the molecular weight of dodecylbenzenesulphonic acid?

The molecular weight of dodecylbenzenesulphonic acid is 326.5 g/mol.

Is dodecylbenzenesulphonic acid soluble in water?

Yes, dodecylbenzenesulphonic acid is soluble in water.

What is the role of dodecylbenzenesulphonic acid as listed in ChEBI?

Dodecylbenzenesulphonic acid has a role as an animal metabolite.

What are some synonyms for dodecylbenzenesulphonic acid?

Some synonyms for dodecylbenzenesulphonic acid include 2-DODECYLBENZENESULFONIC ACID, Dodecylbenzenesulphonic acid, and DODECYL BENZENE SULFONIC ACID.

What is the Canonical SMILES representation of dodecylbenzenesulphonic acid?

The Canonical SMILES representation of dodecylbenzenesulphonic acid is CCCCCCCCCCCCC1=CC=CC=C1S(=O)(=O)O.

What is the InChIKey of dodecylbenzenesulphonic acid?

The InChIKey of dodecylbenzenesulphonic acid is WBIQQQGBSDOWNP-UHFFFAOYSA-N.

What is the CAS number of dodecylbenzenesulphonic acid?

The CAS number of dodecylbenzenesulphonic acid is 27176-87-0.

How many hydrogen bond donors does dodecylbenzenesulphonic acid have?

Dodecylbenzenesulphonic acid has 1 hydrogen bond donor.

What is the topological polar surface area of dodecylbenzenesulphonic acid?

The topological polar surface area of dodecylbenzenesulphonic acid is 62.8 Ų.