1455-42-1

Basic information

• Product Name: 3,9-BIS(1,1-DIMETHYL-2-HYDROXYETHYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE
• Synonyms: 3,9-BIS(1,1-DIMETHYL-2-HYDROXYETHYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE;2,2'-(2,4,8,10-TETRAOXASPIRO[ 5.5] UNDECANE-3,9-DIYL)BIS(2,2-DIMETHYLETHANOL);BIS(HYDROXYPIVALALDEHYDE) PENTAERYTHRITOLACETAL CYCLIC ACETAL;SPIROGLYCOL;2,2-Dimethyl-3-hydroxypropionaldehyde pentaerythrityl bisacetal;3 9-BIS(1,1-DIMETHYL-2-HYDROXYETHYL)-2,4,8,10-TETRAOXASPIRO [5.5]UNDECANE 97+%;3,9-BIS(1,1-DIMETHYL-2-HYDROXYETHYL)-2,4,8,10-TETRAOXASPIRO[;3,9-Bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro5.5üundecane, 97%
• CAS NO: 1455-42-1
• Molecular Formula: C₁₅H₂₈O₆
• Molecular Weight: 304.38
• EINECS: 485-230-3
• Product Categories: Dioxanes;Dioxanes & Dioxolanes
• Mol File: 1455-42-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 198-200°C
• Boiling Point: 434.2 °C at 760 mmHg
• Flash Point: 216.4 °C
• Appearance: /
• Density: 1.16
• Vapor Pressure: 2.3E-09mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: almost transparency in hot Methanol
• PKA: 14.38±0.10(Predicted)
• Water Solubility: 168mg/L at 20℃
• BRN: 1574570
• CAS DataBase Reference: 3,9-BIS(1,1-DIMETHYL-2-HYDROXYETHYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,9-BIS(1,1-DIMETHYL-2-HYDROXYETHYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE(1455-42-1)
• EPA Substance Registry System: 3,9-BIS(1,1-DIMETHYL-2-HYDROXYETHYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE(1455-42-1)

Safety Data

• Safety Statements: 22-24/25
• TSCA: Yes
• Hazardous Substances Data: 1455-42-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C15H28O6/c1-13(2,5-16)11-18-7-15(8-19-11)9-20-12(21-10-15)14(3,4)6-17/h11-12,16-17H,5-10H2,1-4H3

Synthetic route

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + Pentaerythritol (115-77-5) → 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1)

Conditions	Yield
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; Pentaerythritol; sulfuric acid In water; xylene at 60℃; for 14h; Stage #2: With sodium hydroxide Conversion of starting material;	89%
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; Pentaerythritol; hydrogenchloride In water at 70℃; for 8h; Stage #2: With sodium hydroxide at 40℃; pH=6.5; Conversion of starting material;	83%
sulfuric acid In water at 60℃; for 6h; Conversion of starting material;	80%

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1) + chlorophosphoric acid diphenyl ester (2524-64-3) → C39H46O12P2 (1431135-47-5)

Conditions	Yield
With magnesium chloride In toluene at 100℃; for 5h; Inert atmosphere;	87%

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1) + 4-Nitrophthalonitrile (31643-49-9) → 4,4’-(((2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(2-methylpropane-2,1-diyl))bis(oxy))diphthalonitrile

Conditions	Yield
With potassium carbonate In acetonitrile for 72h; Reflux;	85%

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1) + chlorophosphoric acid diphenyl ester (2524-64-3) → C39H46O12P2 (1431135-47-5) + C60H77O20P3

Conditions	Yield
With magnesium chloride In toluene at 100℃; for 5h; Inert atmosphere; Overall yield = 87 %;

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1) + O-phenyl phosphorodichloridate (770-12-7) + chlorophosphoric acid diphenyl ester (2524-64-3) → C39H46O12P2 (1431135-47-5) + C60H77O20P3 + C81H108O28P4

Conditions	Yield
With magnesium chloride In toluene at 100℃; for 5h; Inert atmosphere;

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1) + poly(methacrylic acid) (79-41-4) → C23H36O8

Conditions	Yield
With toluene-4-sulfonic acid; copper(II) sulfate; 4-methoxy-phenol In tetrahydrofuran; toluene at 65 - 85℃; for 2h;

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1) + D-camphor-10-sulfonyl chloride (21286-54-4, 39262-22-1) → (2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(2-methylpropane-2,1-diyl) bis((7,7-dimethyl-2-oxobicyclo[2.2.1]-heptan-1-yl)methanesulfonate)

Conditions	Yield
With dmap In dichloromethane for 12h; Schlenk technique; Inert atmosphere;

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane (1455-42-1) + R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid (20445-31-2) → (2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(2-methylpropane-2,1-diyl) (2R,2'R)-bis(3,3,3-trifluoro-2-methoxy-2-phenylpropanoate)

Conditions	Yield
Stage #1: R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.0333333h; Schlenk technique; Stage #2: 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane In dichloromethane Schlenk technique; Inert atmosphere;

Upstream product

• 597-31-9 2,2-dimethyl-3-hydroxypropionaldehyde 
• 115-77-5 Pentaerythritol 

Downstream Products

• 1431135-47-5 C₃₉H₄₆O₁₂P₂ 

Relevant articles and documents

METHOD FOR PRODUCING DIOL HAVING CYCLIC ACETAL SKELETON

The present invention provides a method for producing a diol having a cyclic acetal skeleton, in which the method include an acetalization reaction step of obtaining a diol having a cyclic acetal skeleton by subjecting raw material hydroxypivalaldehyde and at least pentaerythritol and/or trimethylolpropane to an acetalization reaction under an acid catalyst and the raw material hydroxypivalaldehyde can contain a prescribed amount of at least one impurity selected from the group consisting of formaldehyde, neopentyl glycol, an ester compound having a neopentyl glycol skeleton represented by formula (III), and isobutyraldehyde.

PROCESS FOR PRODUCTION OF A SPIROGLYCOL

Disclosed is a process for production of a spiroglycol by subjecting pentaerythritol to reaction in water with hydroxypivaldehyde in presence of a catalytically active amount of at least one acid catalyst and seed particles, wherein pentaerythritol, water, at least one acid catalyst and spiroglycol seed particles are charged to a reaction vessel, equipped with heating/cooling and agitation, and under stirring heated to a predetermined reaction temperature followed by progressive addition of hydroxypivaldehyde. The spiroglycol seed particles are present in an amount of 0.5-1.0% by weight, calculated on pentaerythritol, water, acid catalyst and hydroxypivaldehyde, and the hydroxypivaldehyde is charged at a rate determined over time by monitoring growth and/or formation of yielded spiroglycol particles.