2590-16-1

Basic information

• Product Name: PENTAERYTHRITOLDIALLYLETHER
• Synonyms: PENTAERYTHRITOLDIALLYLETHER
• CAS NO: 2590-16-1
• Molecular Formula: C₁₁H₂₀O₄
• Molecular Weight: 216.27
• Mol File: 2590-16-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PENTAERYTHRITOLDIALLYLETHER(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAERYTHRITOLDIALLYLETHER(2590-16-1)
• EPA Substance Registry System: PENTAERYTHRITOLDIALLYLETHER(2590-16-1)

Safety Data

• Hazardous Substances Data: 2590-16-1(Hazardous Substances Data)

Usage

General Description

Pentaerythritoldiallylether is a chemical compound that is derived from pentaerythritol and contains multiple allyl groups. It is a versatile and reactive compound that is commonly used as a crosslinking agent in various polymerization processes, including the production of resins, adhesives, and coatings. Pentaerythritoldiallylether is known for its ability to improve the mechanical and thermal properties of polymers, making it a valuable ingredient in the formulation of high-performance materials. Its high reactivity and crosslinking capabilities make it useful in the manufacturing of composites, laminates, and other structural materials. Additionally, pentaerythritoldiallylether is also utilized in the production of specialty chemicals and pharmaceuticals, further showcasing its diverse range of applications.

Synthetic route

Pentaerythritol (115-77-5) + 3-chloroprop-1-ene (107-05-1) → pentaerythritol tetraallyl ether (1471-18-7) + 2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1) + pentaerythritol triallyl ether (1471-17-6)

Conditions	Yield
Stage #1: Pentaerythritol With tetrabutylammomium bromide; sodium hydroxide In water at 90℃; Industrial scale; Stage #2: 3-chloroprop-1-ene In water at 110℃; Industrial scale;	A 6.1% B 5.3% C 87.6%
(i) DMSO, NaOH, (ii) /BRN= 635704/; Multistep reaction;

Pentaerythritol (115-77-5) + allyl bromide (106-95-6) → pentaerythritol tetraallyl ether (1471-18-7) + 2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1)

Conditions	Yield
With sodium hydroxide In water at 70℃; for 12h;	A 56% B 25%

1,4-dibromo-butane (110-52-1) + pentaerythritol tetraallyl ether (1471-18-7) → 2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1) + C18H31BrO4 (1428988-80-0)

Conditions	Yield
Stage #1: pentaerythritol tetraallyl ether With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide; mineral oil at 60℃; for 72h;	A 30% B 24%

Pentaerythritol (115-77-5) + allyl bromide (106-95-6) → 2-allyloxymethyl-2-hydroxymethylpropane-1,3-diol (3784-12-1) + 2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 45 - 47℃;	A 27.8% B 21%

Pentaerythritol (115-77-5) + 3-chloroprop-1-ene (107-05-1) → 2-allyloxymethyl-2-hydroxymethylpropane-1,3-diol (3784-12-1) + 2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1)

Conditions	Yield
With 1,4-dioxane; sodium hydroxide

Pentaerythritol (115-77-5) → 2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 12 h / 70 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 2.2: 72 h / 60 °C View Scheme

2-allyloxymethyl-2-hydroxymethylpropane-1,3-diol (3784-12-1) + 3-chloroprop-1-ene (107-05-1) → 2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1)

Conditions	Yield
Stage #1: 2-allyloxymethyl-2-hydroxymethylpropane-1,3-diol With sodium hydroxide at 120℃; for 7h; Stage #2: 3-chloroprop-1-ene at 120℃; for 10h; Temperature;

2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1) → 2,2-bis-(2,3-dihydroxy-propoxymethyl)-propane-1,3-diol (62972-05-8)

Conditions	Yield
With osmium(VIII) oxide; ethanol; dihydrogen peroxide

2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1) → nitric acid-(2,2-bis-allyloxymethyl-propanediyl ester)

2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1) → 2,2-bis-propoxymethyl-propane-1,3-diol (872826-06-7)

Conditions	Yield
With ethanol; platinum Hydrogenation;

2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1) → nitric acid-(2,2-bis-propoxymethyl-propanediyl ester)

Conditions	Yield
Multi-step reaction with 2 steps 1: platinum; ethanol / Hydrogenation View Scheme

2,2-bis(allyloxymethyl)propane-1,3-diol + acetone (67-64-1) → C14H24O4

Conditions	Yield
With toluene-4-sulfonic acid

2,2-bis(allyloxymethyl)propane-1,3-diol (2590-16-1) + 3-chloroprop-1-ene (107-05-1) → pentaerythritol triallyl ether (1471-17-6)

Conditions	Yield
Stage #1: 2,2-bis(allyloxymethyl)propane-1,3-diol With sodium hydroxide at 120℃; for 7h; Stage #2: 3-chloroprop-1-ene at 120℃; for 10h; Temperature;

Upstream product

• 115-77-5 Pentaerythritol 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 110-52-1 1,4-dibromo-butane 
• 1471-18-7 pentaerythritol tetraallyl ether 
• 3784-12-1 2-allyloxymethyl-2-hydroxymethylpropane-1,3-diol 

Downstream Products

• 1471-17-6 pentaerythritol triallyl ether 

Relevant articles and documents

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Preparation method of pentaerythritol triallyl ether

The invention provides a preparation method of pentaerythritol triallyl ether and particularly relates to the technical field of synthesis of pentaerythritol triallyl ether. The method is characterized by comprising the following steps: S1, under normal pressure, feeding pentaerythritol, pentaerythritol triallyl ether, tetrabutylammonium bromide and 50% sodium hydroxide aqueous solution into a stirring reaction kettle, and heating the mixture to dissolve pentaerythritol into liquid; S2, dropwise adding chloropropene, keeping chloropropene and water evaporated, and layering the chloropropene and water after condensation, and returning chloropropene to the stirring reaction kettle; and S3, after the reaction is finished, adding water, and cooling and standing the mixture for layering, and carrying out reduced pressure distillation on the upper organic phase to obtain the product pentaerythritol triallyl ether. According to the preparation method of pentaerythritol triallyl ether providedby the invention, pentaerythritol triallyl ether is adopted as a solvent during synthesis, the addition of an inert solvent in the existing process is optimized and removed, rectification recycling or environment-friendly treatment measures of the inert solvent are not needed, and high-pressure operation of taking water as the solvent is avoided, so that the reaction is beneficial to the generation of pentaerythritol triallyl ether.

Diphilic carbosilane dendrimers with different densities of the hydrophilic layer

A universal method for the synthesis of hydrophilic dendrimers was considered. The method is based on a combination of carbosilane dendrimers with different molecular organizations and hydrophilizing agents, viz., substituted hydride silanes containing one and three protected hydroxyl groups. The combination of a limited set of the mentioned reagents makes it possible to control the ratio of hydrophilic and hydrophobic moieties of the molecular structure in wide limits. A simple and convenient method for the removal of trimethylsilyl protection of hydroxyl groups in the surface layer of dendrimers was developed.