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Dilauryl thiodipropionate

Catalog Number
ACM123284-1
CAS
123-28-4
Structure
IUPAC Name
Dodecyl 3-(3-dodecoxy-3-oxopropyl)sulfanylpropanoate
Synonyms
Propanoic acid, 3,3'-thiobis-, didodecyl ester
Molecular Weight
514.84
Molecular Formula
C30H58O4S
Canonical SMILES
CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC
InChI
GHKOFFNLGXMVNJ-UHFFFAOYSA-N
InChI Key
InChI=1S/C30H58O4S/c1-3-5-7-9-11-13-15-17-19-21-25-33-29(31)23-27-35-28-24-30(32)34-26-22-20-18-16-14-12-10-8-6-4-2/h3-28H2,1-2H3
Boiling Point
570 °C
Melting Point
40-42 °C(lit.)
Flash Point
>110°C
Density
0.915g/ml
Solubility
water, 4.94e-008 mg/L @ 25 °C (est)
Appearance
White crystalline powder
Active Content
95%
Physical State
Solid
Typical Applications
Use as antioxidant.
Use as sulfur-based extreme pressure lubricant.
Use as dispersing agent, emulsion stabilizer.
Spec Sheet
Case Study

Dilauryl Thiodipropionate (DLTDP) Used as a Regeneration Agent for Reclaimed Asphalt Pavement (RAP) Binders

Dilauryl Thiodipropionate (DLTDP) Used as a Regeneration Agent for Reclaimed Asphalt Pavement (RAP) Binders Camargo, Ingrid, et al. Construction and Building Materials 365 (2023): 130049.

Dilauryl thiodipropionate (DLTDP), a thioether-based antioxidant, has demonstrated promising potential as a regeneration agent for aged reclaimed asphalt pavement (RAP) binders. In this study, two types of RAP binders-one artificially aged and one field-aged-were rejuvenated with DLTDP to evaluate its effectiveness in restoring critical performance characteristics lost due to oxidation and aging.
To prepare the DLTDP-modified binders, 100 ± 25 g of RAP binder was first heated at 145 °C for 60 minutes in a covered container to minimize further oxidative aging. DLTDP was then added slowly by hand to prevent aggregation, followed by high-shear mixing at 1200 ± 20 rpm and 150 ± 5 °C for 45 minutes to ensure uniform dispersion. Identically treated RAP binders without DLTDP served as controls.
The blends underwent Rolling Thin Film Oven Test (RTFOT) aging and further long-term aging using the Pressure Aging Vessel (PAV). Rheological testing via Dynamic Shear Rheometer (DSR), chemical analysis using FTIR, and SARA fractionation revealed that DLTDP effectively increased maltene content while reducing asphaltenes. These changes improved binder workability and resistance to oxidative aging. Bitumen Bond Strength (BBS) tests showed that the regenerated binders retained strong adhesion under both dry and wet conditions.
Overall, DLTDP partially restored the chemical and rheological properties of RAP binders, enabling high RAP content usage without compromising performance-highlighting its utility in sustainable asphalt pavement design.

Dilauryl Thiodipropionate Used for Anti-Aging Modification of Asphalt Binders: Rheological Evaluation and Performance Limitations

Dilauryl Thiodipropionate Used for Anti-Aging Modification of Asphalt Binders: Rheological Evaluation and Performance Limitations Camargo, Ingrid, Bernhard Hofko, and Johannes Mirwald. Construction and Building Materials 314 (2022): 125489.

Dilauryl thiodipropionate (DLTDP), a sulfur-containing antioxidant, has recently gained attention as a potential anti-aging additive for asphalt binder formulations. In a two-phase experimental investigation, the effects of DLTDP, both alone and in combination with furfural, were systematically studied to assess their influence on binder rheology and Performance Grade (PG).
In Phase I, DLTDP was dosed based on achieving a minimum rheological aging index. Asphalt samples modified with varying concentrations of DLTDP exhibited binder-type-dependent softening, negatively impacting rutting resistance. Fourier-transform infrared spectroscopy (FTIR) indicated compositional changes post-modification, complicating functional group quantification. When used alongside furfural, evaporative losses were observed during short-term aging at 163 °C, exceeding furfural's boiling point, limiting its efficacy.
Phase II focused on the PG-grade implications of the additive combination. Although improvements in fatigue and thermal cracking resistance were observed at intermediate and low temperatures, the overall PG span narrowed. This shrinkage was primarily attributed to the disproportionate softening at high temperatures, thereby undermining the benefits of long-term aging resistance.
The results suggest that while DLTDP softens asphalt binders and may contribute to anti-aging effects, its combined use with volatile agents like furfural may not be suitable for hot-mix applications. Further investigation into binder-additive interactions using broader analytical techniques and binder sources is warranted.

Dilauryl Thiodipropionate Used for Enhancing Thermal-Oxidative Stability of PAO10 Lubricants via Synergistic Antioxidant Mechanism

Dilauryl Thiodipropionate Used for Enhancing Thermal-Oxidative Stability of PAO10 Lubricants via Synergistic Antioxidant Mechanism Chao, Mianran, Weimin Li, and Xiaobo Wang. Journal of Thermal Analysis and Calorimetry 117.2 (2014): 925-933.

Dilauryl thiodipropionate (DLTDP), a sulfur-containing secondary antioxidant, has been investigated for its ability to enhance the oxidative resistance of synthetic base oils. In this study, DLTDP was employed in combination with an oil-soluble primary antioxidant, alkylated diphenylamine (ADPA), to improve the thermal-oxidative stability of polyalphaolefin (PAO10) base oil. The evaluation employed a multi-technique approach, including rotary bomb oxidation test (RBOT), pressurized differential scanning calorimetry (PDSC), hot oil oxidation test, thermogravimetric analysis (TGA), and kinetic parameter analysis using the Kissinger method.
Experimental results revealed that while both DLTDP and ADPA independently enhanced the oxidation induction time (OIT) of PAO10 (250 min and 287 min, respectively), their combination exhibited a pronounced synergistic effect. A formulation of 0.9 wt% ADPA and 0.1 wt% DLTDP extended the OIT to 1,054 min-nearly 20 times that of neat PAO10 (53 min). Kinetic analysis further confirmed that the ADPA-DLTDP blend significantly increased the activation energy of the thermal-oxidative degradation process, indicating a reduced oxidation rate.
The synergy is attributed to the distinct antioxidant mechanisms: ADPA acts as a radical scavenger while DLTDP decomposes hydroperoxides, thereby interrupting oxidation propagation. This study demonstrates that DLTDP is a highly effective co-antioxidant in lubricant formulations, particularly when paired with aromatic amine-type primary antioxidants.

Custom Q&A

What is the product name of CAS number 123-28-4?

The product name is Dilauryl thiodipropionate.

What is the synonym for Dilauryl thiodipropionate?

The synonym is Propanoic acid, 3,3'-thiobis-, didodecyl ester.

What is the IUPAC name of Dilauryl thiodipropionate?

The IUPAC name is Dodecyl 3-(3-dodecoxy-3-oxopropyl)sulfanylpropanoate.

What is the molecular weight of Dilauryl thiodipropionate?

The molecular weight is 514.84 g/mol.

What is the molecular formula of Dilauryl thiodipropionate?

The molecular formula is C30H58O4S.

What is the appearance of Dilauryl thiodipropionate?

It appears as a white crystalline powder.

What are the typical applications of Dilauryl thiodipropionate?

Some typical applications include use as an antioxidant, use as a sulfur-based extreme pressure lubricant, and use as a dispersing agent and emulsion stabilizer.

What is the boiling point of Dilauryl thiodipropionate?

The boiling point is 570°C.

What is the melting point of Dilauryl thiodipropionate?

The melting point is 40-42°C.

What is the physical state of Dilauryl thiodipropionate?

It is in a solid physical state.

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