Dodecenylsuccinic anhydride
[CAS 25377-73-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Carboxylic anhydride
• Name: Dodecenylsuccinic anhydride
• Synonyms: 3-[(E)-dodec-1-enyl]oxolane-2,5-dione
• Molecular Formula: C₁₆H₂₆O₃
• Molecular Weight: 266.38
• CAS Registry Number: 25377-73-5
• EC Number: 246-917-1
• SMILES: CCCCCCCCCC/C=C/C1CC(=O)OC1=O

Properties

• Boiling point: 386.3±31.0 °C 760 mmHg (Calc.)^*, 180 - 182 °C (Expl.)
• Flash point: 173.6±22.0 °C (Calc.)^*, 177 °C (Expl.)
• Index of refraction: 1.517 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H317-H319-H332-H412
• Safety Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P317-P321-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H332
Skin sensitization	Skin Sens.	1A	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Respiratory sensitization	Resp. Sens.	1	H334
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

chemBlink Chemical Story

Why does a sheet of paper resist a drop of water instead of immediately behaving like blotting paper? One answer lies in alkenylsuccinic anhydride chemistry. Dodecenylsuccinic anhydride, or DDSA, is a C12 alkenyl-substituted succinic anhydride and belongs to the same reactive family used to make paper surfaces less wettable.

The molecule contains two personalities. Its cyclic anhydride is highly reactive toward nucleophiles such as water and alcohol groups. Its long dodecenyl chain is strongly hydrophobic. In papermaking, alkenylsuccinic anhydride sizing agents are dispersed into the aqueous fiber slurry and deposited onto cellulose. During drying and heating, the hydrophobic alkenyl group becomes associated with the fiber surface, reducing the tendency of water to spread and penetrate.

For decades, the textbook explanation was especially elegant: the anhydride reacts directly with cellulose hydroxyl groups to form ester bonds, permanently attaching the hydrophobic chain to the fiber. Recent work has shown that the real story is more complicated. ASA hydrolyzes rapidly in water, and researchers still debate how much covalent esterification with cellulose is required for effective sizing. A 2023 study revisited this question and found that the relationship between covalent bonding and water repellency is not as simple as the traditional diagram suggests.

That controversy is scientifically valuable. It reminds us that a successful industrial process can precede complete molecular agreement about why it works. Papermakers know how to control emulsion quality, retention, pH, drying, and dosage to obtain sizing. Surface chemists continue to ask exactly how hydrolyzed and unhydrolyzed ASA species organize on fibers and which interactions dominate the final hydrophobic effect.

DDSA is also used beyond paper. The same anhydride ring can react with epoxide systems, so long-chain alkenylsuccinic anhydrides can function in epoxy curing and modification. The hydrophobic chain then influences flexibility and compatibility, while the anhydride provides the reactive functionality. Related derivatives are also used as intermediates in lubricants, fuel additives, and modified starch chemistry.

The memorable feature of DDSA is the pairing of a reactive head with a hydrophobic tail. The anhydride gives chemists a way to attach or interact with polar substrates; the C12 alkenyl chain changes how the treated material deals with oil and water. In paper sizing, that small molecular design helps determine whether a liquid spreads into a fiber network or beads on the surface.

References:
1. PubChem, Dodecenylsuccinic anhydride, CID 6433892, CAS 25377-73-5.
2. Ntifafa Y. et al. Alkenyl Succinic Anhydride: The Question of Covalent Bonding with Cellulose. BioResources / related open-access study, 2023.
3. Literature on alkenylsuccinic anhydride reactive paper sizing.
4. Industrial references on DDSA and related ASA derivatives in epoxy and paper applications.

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