1,4-Bis(2-hydroxyethoxy)-2-butyne

• CAS: 1606-85-5
• Catalog Number: ACM1606855-4
• Category: Main Products
• Molecular Weight: 174.19
• Molecular Formula: C8H14O4
• Synonyms: 2,2'-(But-2-yne-1,4-diylbis(oxy))diethanol
• IUPAC Name: 2-[4-(2-Hydroxyethoxy)but-2-ynoxy]ethanol
• Canonical SMILES: C(COCC#CCOCCO)O
• InChI: InChI=1S/C8H14O4/c9-3-7-11-5-1-2-6-12-8-4-10/h9-10H,3-8H2
• InChI Key: IXAWTPMDMPUGLV-UHFFFAOYSA-N
• Boiling Point: 225.17 °C
• Appearance: Liquid
• Storage: Sealed in dry, room temperature
• Exact Mass: 174.08920892
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 2
• Monoisotopic Mass: 174.08920892
• Rotatable Bond Count: 6
• Topological Polar Surface Area: 58.9 Ų

Case Study

Synthesis of 1,4-Bis(2-Hydroxyethoxy)-2-Butyne-Modified Polysiloxanes

Du, Zhiping, et al. The Journal of Physical Chemistry B, 2015, 119(44), 14180-14187.

Five different butynediol ethoxylated polysiloxanes (PSi-EO) were designed and synthesized via a two-step reaction: low-hydrogen silicone oil (LPMHS) was prepared by acid-catalyzed polymerization followed by hydrosilylation with 1,4-bis(2-hydroxyethoxy)-2-butyne (BEO). The different effects of the siloxane chains and 1,4-bis(2-hydroxyethoxy)-2-butane (BEO) units on the surface activity and aggregation behavior were elucidated using various techniques.
· Synthesis of PSi-EO
In a 250 mL four-necked flask fitted with a reflux condenser, thermometer, and nitrogen inlet/outlet, BEO (17.4 g) and LPMHS (52.6 g; Si-H content of 0.19%) were combined with Speier's reagent. The reaction was maintained at reflux at 130 °C for 2 hours. Following the removal of low boiling substances, the resulting product achieved a total yield of 97.2%.
· Surface Activity and Aggregation Behavior
The aqueous solution of PSi-EO exhibited a relatively low critical aggregation concentration of 15-34 mg·L-1 and a surface tension of approximately 25 mN·m-1. The reduction in surface tension was found to increase with higher concentrations of PSi-EO and a greater proportion of hydrophilic groups in the synthesized compounds. Additionally, dynamic light scattering (DLS) and transmission electron microscopy (TEM) analyses demonstrated that PSi-EO self-assembled into spherical aggregates in the aqueous environment.

1,4-Bis(2-Hydroxyethoxy)-2-Butyne for the Synthesis of Trisiloxane Surfactant

Wang, Guoyong, et al. Journal of Molecular Liquids, 2014, 197, 197-203.

In this work, a new butynediol ethoxylated trisiloxane (BDET) surfactant was prepared by the hydrosilylation reaction of 1,1,1,3,5,5,5-heptamethyltrisiloxane and 1,4-bis(2-hydroxyethoxy)-2-butyne using H2PtCl6 as a catalyst.
· Synthesis of BDET Surfactant
A 250 mL four-neck round-bottom flask was set up with a stirrer, condenser, thermometer, and nitrogen inlet/outlet. The flask was charged with 43.5 g (0.25 mol) of BEO, 55.5 g (0.25 mol) of HMTS, and 8 mL of an isopropanol solution of H2PtCl6 (1 mg/L). The mixture was heated to 110 °C and stirred under nitrogen for 3 hours.
· BDET Surfactant Performance
The surface tension of the trisiloxane surfactant at its critical aggregate concentration (CAC) was notably lower than that of the acetylene diol-based surfactant. The aggregates formed by this nonionic surfactant in an aqueous solution were identified as spherical assemblies. Furthermore, its spreading capabilities at the interface of low-energy polytetrafluoroethylene and paraffin films were assessed, highlighting its potential usefulness as a spreading agent in industrial applications.