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

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

Uses

Used in Coatings Industry:
TRIPENTAERYTHRITOL is used as a crosslinking agent for its ability to react with isocyanates, which enhances the durability and performance of coatings. This application is particularly relevant in the production of automotive coatings, wood coatings, and industrial maintenance coatings.
Used in Plastics Industry:
In the plastics industry, TRIPENTAERYTHRITOL is used as a plasticizer for polyvinyl chloride (PVC) to improve its flexibility and workability. Its esterification properties allow it to form strong bonds with the polymer chains, resulting in improved mechanical properties and resistance to environmental factors.
Used in Adhesives Industry:
TRIPENTAERYTHRITOL is used as a reactive diluent in the formulation of adhesives, particularly in the production of polyurethane-based adhesives. Its high reactivity and compatibility with various polymers contribute to the development of strong, durable, and fast-setting adhesives.
Used in Lubricant Additives Industry:
TRIPENTAERYTHRITOL is used as a component in the synthesis of various lubricant additives, such as extreme pressure additives and antioxidants. Its esterification properties enable it to form stable and effective additives that enhance the performance and longevity of lubricants.
Used in Explosives Industry:
In the explosives industry, TRIPENTAERYTHRITOL is used as a component in the production of certain types of explosives due to its high energy content and compatibility with other explosive materials.
Used in Hard Resins, Varnishes, and Fast-Drying Tall-Oil Vehicles:
TRIPENTAERYTHRITOL is used as a reactive diluent and crosslinking agent in the production of hard resins, varnishes, and fast-drying tall-oil vehicles. Its ability to form strong bonds with other components in these formulations results in improved hardness, durability, and drying times.

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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