78-19-3

Basic information

• Product Name: 3,9-Divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane
• Synonyms: 2,4,8,10-Tetraoxaspiro[5.5]undecane, 3,9-divinyl-;2,4,8,10-Tetraoxaspiro[5.5]undecane,3,9-diethenyl-(9CI);8,10-tetraoxaspiro(5,5)undecane,3,9-diethenyl-4;8,10-tetraoxaspiro(5.5)undecane,3,9-divinyl-4;Acrolein pentaerythritol bisacetal;Acrolein, cyclic diacetal with pentaerythritol;Acrolein, cyclic neopentanetetrayl acetal;Acrolein-pentaerythritol dicyclic acetal
• CAS NO: 78-19-3
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.24
• EINECS: 201-092-7
• Product Categories: Dioxanes;Dioxanes & Dioxolanes;Acyclic;Alkenes;Organic Building Blocks;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 78-19-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 43-46 °C(lit.)
• Boiling Point: 108-110 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.251 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00512mmHg at 25°C
• Refractive Index: 1.4389 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: almost transparency in Methanol
• CAS DataBase Reference: 3,9-Divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane(CAS DataBase Reference)
• NIST Chemistry Reference: 3,9-Divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane(78-19-3)
• EPA Substance Registry System: 3,9-Divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane(78-19-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: XF0875000
• Hazardous Substances Data: 78-19-3(Hazardous Substances Data)

Usage

Description

3,9-Divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane is an acetal-type crosslinking agent comonomer that exists as white crystals or a crystalline mass. It is characterized by its ability to form crosslinks in polymers, which enhances their stability and mechanical properties.

Uses

Used in Pharmaceutical Industry:
3,9-Divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane is used as a crosslinking agent for the synthesis of acid-degradable core-crosslinked micelles. These micelles are biocompatible copolymers that can be used for loading drug models, such as indomethacin, to improve drug delivery and release profiles.
Used in Polymer Industry:
3,9-Divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane is used as a comonomer in the radical emulsion copolymerization of 2-hydroxyethyl methacrylate. Its incorporation into the polymer chain enhances the crosslinking properties, leading to improved mechanical strength and stability of the resulting polymer materials.

InChI:InChI=1/C11H16O4/c1-3-9-12-5-11(6-13-9)7-14-10(4-2)15-8-11/h3-4,9-10H,1-2,5-8H2

Upstream product

• 115-77-5 Pentaerythritol 
• 107-02-8 acrolein 

Downstream Products

• 65967-52-4 diketene acetal (3,9-bis(ethylidene)-2,4,8,10-tetraoxaspiro<5,5>undecane) 

Relevant articles and documents

Unlocking the Potential of Poly(Ortho Ester)s: A General Catalytic Approach to the Synthesis of Surface-Erodible Materials

Poly(ortho ester)s (POEs) are well-known for their surface-eroding properties and hence present unique opportunities for controlled-release and tissue-engineering applications. Their development and wide-spread investigation has, however, been severely limited by challenging synthetic requirements that incorporate unstable intermediates and are therefore highly irreproducible. Herein, the first catalytic method for the synthesis of POEs using air- and moisture-stable vinyl acetal precursors is presented. The synthesis of a range of POE structures is demonstrated, including those that are extremely difficult to achieve by other synthetic methods. Furthermore, application of this chemistry permits efficient installation of functional groups through ortho ester linkages on an aliphatic polycarbonate.