2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacetoacetate

Base Information

• Chemical Name: 2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacetoacetate
• CAS No.: 22208-25-9
• Molecular Formula: C₁₈H₂₆O₉
• Molecular Weight: 386.399
• Hs Code.: 2918300090
• European Community (EC) Number: 422-630-9,682-782-9
• DSSTox Substance ID: DTXSID5051868
• Nikkaji Number: J64.285A
• Wikidata: Q81984850
• Mol file: 22208-25-9.mol

Synonyms:22208-25-9;Trimethylolpropane triacetoacetate;2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacetoacetate;2,2-bis(3-oxobutanoyloxymethyl)butyl 3-oxobutanoate;BRN 4332148;BUTANOIC ACID, 3-OXO-, 2-[(1,3-DIOXOBUTOXY)METHYL]-2-ETHYL-1,3-PROPANDIYL ESTER;Acetoacetic acid, 1,1,1-trihydroxy-methylpropane triester;Butanoic acid, 3-oxo-, 2-((1,3-dioxobutoxy)methyl)-2-ethyl-1,3-propanediyl ester;1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)-, triacetoacetate;Acetoacetic acid, triester with 2-ethyl-2-(hydroxymethyl)-1,3-propanediol;Butanoic acid, 3-oxo-, 1,1'-(2-((1,3-dioxobutoxy)methyl)-2-ethyl-1,3-propanediyl) ester;Butanoic acid, 3-oxo-, 2-[(1,3-dioxobutoxy)methyl]-2-ethyl-1,3-propanediyl ester;SCHEMBL651229;DTXSID5051868;LS-120410;1,1,1-Tri((1,3-dioxobutoxy)-methyl)-propane;Tris(3oxobutanoic acid) Propane-1,1,1-trimethyl;Butanoic acid,3-oxo-,2-[(1,3-dioxobutoxy)methyl]-2-ethyl-1,3-propandiyl ester

Chemical Property of 2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacetoacetate

Chemical Property:

• Vapor Pressure: 1.43E-10mmHg at 25°C
• Boiling Point: 511.3°Cat760mmHg
• PKA: 9.79±0.46(Predicted)
• Flash Point: 221.9°C
• PSA: 130.11000
• Density: 1.179g/cm³
• LogP: 0.94970
• Water Solubility.: 22g/L at 20℃
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 16
• Exact Mass: 386.15768240
• Heavy Atom Count: 27
• Complexity: 513

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s): A poison by ingestion and skin contact.
• Hazard Codes: A poison by ingestion and skin contact.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(COC(=O)CC(=O)C)(COC(=O)CC(=O)C)COC(=O)CC(=O)C
• Uses: LONZAMON(R) AATMP is a trifunctional crosslinker with reactive methylene groups for adhesives, sealants or coatings and a curative for waterborne coating systems. Furthermore it acts as catalyst for amine based epoxy hardeners. WWW Link

Technology Process of 2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacetoacetate

There total 3 articles about 2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacetoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

tert-butyl acetoacetate (1694-31-1) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) → Trimethylolpropane trisacetoacetate (22208-25-9)

Guidance literature:

at 135 ℃; under 1.50015 Torr;

DOI:10.1002/anie.202113872

Reference yield: 85.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) → C14H22O7 + Trimethylolpropane trisacetoacetate (22208-25-9)

Guidance literature:

With 2-(N,N-dimethylamino)ethanol; at 65 - 70 ℃; for 7h; Reagent/catalyst; Temperature; Overall yield = 423.0 g;

Reference yield:

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) → Trimethylolpropane trisacetoacetate (22208-25-9)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; at 125 ℃;

upstream raw materials:

tert-butyl acetoacetate

1,1,1-tri(hydroxymethyl)propane

2,2,6-trimethyl-4H-1,3-dioxin-4-one

4-methyleneoxetan-2-one

Refernces

• 1、 -. "METHOD FOR PREPARATION OF ACETOACETATE ESTER COMPOUNDS". Page/Page column 27; 28. . Retrieved 2021/01/29.
• 2、 Witzeman, J. Stewart,Nottingham, W. Dell. "Transacetoacetylation with tert-Butyl Acetoacetate: Synthetic Apllications". . p. 1713 - 1718. Retrieved 2007/10/02.