78-24-0

Basic information

• Product Name: TRIPENTAERYTHRITOL
• Synonyms: TRIPENTAERYTHRITOL;2,2-bis[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-3-propanediol;3-Propanediol,2,2-bis[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-1;4,8-dioxa-2,2,6,6,10,10-hexahydroxymethylundecane-1,11-diol;TRIPENTAERYTHRITOL, TECH.;Tripentaerythritol, hydroxyl content min. 35%, tech.;1,3-Propanediol, 2,2-bis3-hydroxy-2,2-bis(hydroxymethyl)propoxymethyl-;Tripentaerythritol: (Tripenek)
• CAS NO: 78-24-0
• Molecular Formula: C₁₅H₃₂O₁₀
• Molecular Weight: 372.41
• EINECS: 201-097-4
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 78-24-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 225 °C (dec.)(lit.)
• Boiling Point: 421.87°C (rough estimate)
• Flash Point: 359.5 °C
• Appearance: ivory white to beige crystalline powder
• Density: 1.2442 (rough estimate)
• Vapor Pressure: 7.28E-21mmHg at 25°C
• Refractive Index: 1.5376 (estimate)
• PKA: 13.38±0.10(Predicted)
• CAS DataBase Reference: TRIPENTAERYTHRITOL(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPENTAERYTHRITOL(78-24-0)
• EPA Substance Registry System: TRIPENTAERYTHRITOL(78-24-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 78-24-0(Hazardous Substances Data)

Usage

Chemical Properties

White to ivory powder; has eight primary hydroxyl groups, all esterifiable. Combustible.

Uses

Hard resins, varnishes, and fast-drying tall-oil vehicles.

InChI:InChI=1/C15H32O10/c16-1-13(2-17,3-18)9-24-11-15(7-22,8-23)12-25-10-14(4-19,5-20)6-21/h16-23H,1-12H2

Synthetic route

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → tripentaerythritol (78-24-0)

Conditions	Yield
With sodium hydroxide; Pentaerythritol; water at 58℃;
With sodium hydroxide; Pentaerythritol; water at 58℃;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → Pentaerythritol (115-77-5) + tri(hydroxymethyl)acetaldehyde (3818-32-4) + Dipentaerythritol (126-58-9) + tripentaerythritol (78-24-0) + 3-(3-Hydroxy-2,2-bis-hydroxymethyl-propoxy)-2,2-bis-hydroxymethyl-propionaldehyde + 3-[3-(3-Hydroxy-2,2-bis-hydroxymethyl-propoxy)-2,2-bis-hydroxymethyl-propoxy]-2,2-bis-hydroxymethyl-propionaldehyde

Conditions	Yield
With sodium hydroxide at 30℃; Product distribution; Mechanism; pH=12.5; different initial acetaldehyde concentrations;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → tripentaerythritol (78-24-0) + pentaerythritol and dipentaerythritol

Conditions	Yield
With alkali
With alkali

2-bromophenylacetic acid (4870-65-9) + tripentaerythritol (78-24-0) → bromo-phenyl-acetic acid 3-(bromo-phenyl-acetoxy)-2-[3-(bromo-phenyl-acetoxy)-2-[3-(bromo-phenyl-acetoxy)-2,2-bis-(bromo-phenyl-acetoxymethyl)-propoxymethyl]-2-(bromo-phenyl-acetoxymethyl)-propoxymethyl]-2-(bromo-phenyl-acetoxymethyl)-propyl ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃;	100%

tripentaerythritol (78-24-0) + cyclohexanone (108-94-1) → {3-[3-(3-hydroxymethyl-1,5-dioxa-spiro[5.5]undec-3-ylmethoxymethyl)-1,5-dioxa-spiro[5.5]undec-3-ylmethoxymethyl]-1,5-dioxa-spiro[5.5]undec-3-yl}-methanol

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 5h; Heating;	96%

tripentaerythritol (78-24-0) + 2-chloro-5,5-dimethyl-[1,3,2]dioxaphosphinane (2428-06-0) → octa(5,5-dimethyl-O,O-1,3-propylenephosphite)-2,2-bis(3-hydroxy-2,2-bis-hydroxymethylpropoxymethyl)propane-1,3-diol

Conditions	Yield
With pyridine In 1,4-dioxane at 20℃; Inert atmosphere;	75%

tripentaerythritol (78-24-0) + propargyl bromide (106-96-7) → C39H48O10

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; toluene; mineral oil at 0 - 50℃; for 48h; Inert atmosphere;	65%

2-bromoisobutyric acid bromide (20769-85-1) + tripentaerythritol (78-24-0) → (Octa-O-(2-bromo-2-methylpropionyl)-tripentaerythritol)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 48h; Cooling with ice;	61%
With pyridine In dichloromethane at 0 - 20℃; for 48h;	45%

Dimethoxymethane (109-87-5) + tripentaerythritol (78-24-0) → C19H32O10 (1186366-70-0) + 2',2'':6',6'':10',10''-tri-O-methylene-2,2,6,6,10,10-hexakis(hydroxymethyl)-4,8-dioxa-1,11-undecane-diol (84808-77-5)

Conditions	Yield
With toluene-4-sulfonic acid for 1.5h; Heating;	A 30% B 55%

tripentaerythritol (78-24-0) + hexaethylphosphoric triamide (2283-11-6) → 1,7-bis(2',6',7'-trioxa-1'-phosphabicyclo[2.2.2]-octyl-4')-4,4-bishydrohymethyl-2,6-dioxaheptane (68294-31-5)

Conditions	Yield
With pyridine at 120 - 125℃; for 24h; Inert atmosphere; regioselective reaction;	47%

Dimethoxymethane (109-87-5) + tripentaerythritol (78-24-0) → C19H32O10 (1186366-70-0) + C18H32O10 (1235861-89-8) + 2',2'':6',6'':10',10''-tri-O-methylene-2,2,6,6,10,10-hexakis(hydroxymethyl)-4,8-dioxa-1,11-undecane-diol (84808-77-5)

Conditions	Yield
With toluene-4-sulfonic acid at 110 - 115℃; for 3.5h;	A 33% B 25% C 30%

tripentaerythritol (78-24-0) + benzaldehyde (100-52-7) → {5-[5-(5-hydroxymethyl-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl)-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl]-2-phenyl-[1,3]dioxan-5-yl}-methanol + {5-[5-(5-hydroxymethyl-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl)-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl]-2-phenyl-[1,3]dioxan-5-yl}-methanol + {5-[5-(5-hydroxymethyl-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl)-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl]-2-phenyl-[1,3]dioxan-5-yl}-methanol + {5-[5-(5-hydroxymethyl-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl)-2-phenyl-[1,3]dioxan-5-ylmethoxymethyl]-2-phenyl-[1,3]dioxan-5-yl}-methanol

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 12h; Heating;	A 16% B 19% C 21% D 22%

methyl lactate (547-64-8) + tripentaerythritol (78-24-0) → 2,18-bis-propionyloxy-6,6,10,10,14,14-hexakis-(2-propionyloxy-propionyloxymethyl)-4,8,12,16-tetraoxa-nonadecane-3,17-dione

Conditions	Yield
With sulfuric acid und Behandeln des Reaktionsprodukts mit Propionsaeure-anhydrid und wenig Schwefelsaeure;

tripentaerythritol (78-24-0) → 2',2'':6',6'':10',10''-tri-O-methylene-2,2,6,6,10,10-hexakis(hydroxymethyl)-4,8-dioxa-1,11-undecane-diol (84808-77-5)

Conditions	Yield
With hydrogenchloride; formaldehyd

formaldehyd (50-00-0) + tripentaerythritol (78-24-0) → 2',2'':6',6'':10',10''-tri-O-methylene-2,2,6,6,10,10-hexakis(hydroxymethyl)-4,8-dioxa-1,11-undecane-diol (84808-77-5) + Tripentaerythrit-diformal (84808-76-4)

Conditions	Yield
With hydrogenchloride In water for 3h; Heating;

formaldehyd (50-00-0) + tripentaerythritol (78-24-0) → Tripentaerythrit-monoformal (84808-75-3) + Tripentaerythrit-diformal (84808-76-4)

Conditions	Yield
With hydrogenchloride In water for 3h; Heating;	A 34 % Chromat. B 17 % Chromat.

tripentaerythritol (78-24-0) + benzaldehyde (100-52-7) → 2-[3-(3-benzyloxy-2,2-bis-hydroxymethyl-propoxy)-2-benzyloxymethyl-2-hydroxymethyl-propoxymethyl]-2-benzyloxymethyl-propane-1,3-diol

Conditions	Yield
Stage #1: tripentaerythritol; benzaldehyde With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 12h; Heating; Stage #2: With triethylsilane; ethylaluminum dichloride In dichloromethane at -78℃; for 0.666667h;	65 mg

tripentaerythritol (78-24-0) + p-toluenesulfonyl chloride (98-59-9) → C71H80O26S8

nickel(II) chloride hexahydrate + Na9[A-α-PW9O34]·7H2O + tripentaerythritol (78-24-0) + sodium acetate (127-09-3) + ethylenediamine (107-15-3) → [Ni(en)2(H2O)2][Ni0.5(en)][Ni6(en)3(Ac)2(Tris4)(H2O)2PW9O34]*OH*6H2O

Conditions	Yield
With acetic acid In water High Pressure; hydrothermal react.; mixt. 1.0 g Na9(PW9O34)*7H2O, 0.8 g NiCl2*6H2O, 0.3ml (NH2CH2)2, 0.2 g tripentaerythritol, 10 ml AcOH/AcONa buffer (pH 4.5 ) stirred for 1 h; heated in Teflon-lined steel autoclave at 170°C for 3 d; cooled to room temp.;

tripentaerythritol (78-24-0) + methyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)acrylate (27574-90-9) → Tripentaerythritol-octakis-<3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionat> (16993-81-0)

Conditions	Yield
With sodium methylate at 100℃; under 4.87549 Torr; for 8h; Reagent/catalyst; Temperature; Time;

tripentaerythritol (78-24-0) + 3-mercaptopropionic acid (107-96-0) → tripentaerythritol octa(3-mercaptopropionate)

Conditions	Yield
With SO42-/ Al2O3-ZrO2 at 80 - 100℃;	537 g

tripentaerythritol (78-24-0) + 2,4,5-triiodobenzoic acid (35674-21-6) → C71H40I24O18

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 12h;

tripentaerythritol (78-24-0) + stearic acid (57-11-4) → C159H304O18

Conditions	Yield
With dmap In tetrahydrofuran for 12h;

Upstream product

• 50-00-0 formaldehyd 
• 75-07-0 acetaldehyde 

Downstream Products

• 16993-81-0 Tripentaerythritol-octakis-<3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionat> 

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