23235-61-2

Basic information

• Product Name: Di(trimethylol propane)
• Synonyms: DI(TRIMETHYLOLPROPANE);DTMP;2,2'-OXYBIS(METHYLENE)BIS(2-ETHYL-1,3-PROPANEDIOL);2,2’-[oxybis(methylene)]bis[2-ethyl-3-propanediol;3-Propanediol,2,2’-[oxybis(methylene)]bis[2-ethyl-1;2,2'-[oxybis(methylene)]bis[2-ethylpropane-1,3-diol];Ditrimethylol;1,3-Propanediol, 2,2-oxybis(methylene)bis2-ethyl-
• CAS NO: 23235-61-2
• Molecular Formula: C₁₂H₂₆O₅
• Molecular Weight: 250.33
• EINECS: 245-509-0
• Mol File: 23235-61-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 108-111 °C(lit.)
• Boiling Point: 215 °C4 mm Hg(lit.)
• Flash Point: 217.2 °C
• Appearance: /
• Density: 1.0187 (rough estimate)
• Vapor Pressure: 2.05E-09mmHg at 25°C
• Refractive Index: 1.4560 (estimate)
• Solubility: soluble in Methanol
• PKA: 13.90±0.10(Predicted)
• Water Solubility: 21g/L at 20℃
• BRN: 1860782
• CAS DataBase Reference: Di(trimethylol propane)(CAS DataBase Reference)
• NIST Chemistry Reference: Di(trimethylol propane)(23235-61-2)
• EPA Substance Registry System: Di(trimethylol propane)(23235-61-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 23235-61-2(Hazardous Substances Data)

Usage

Uses

Used in Polymer Synthesis:
Di(trimethylol propane) is used as a core molecule for the synthesis of lipase-catalyzed hyperbranched polymers. Its tetrafunctional nature allows for the creation of complex and highly branched structures, which can be tailored for specific applications.
Used in Pharmaceutical Industry:
Di(trimethylol propane) is used as a key component in the formation of biodegradable polymers for drug delivery applications. These polymers can be designed to control the release of drugs, improving their efficacy and reducing side effects. The biodegradable nature of these polymers also minimizes the risk of long-term complications associated with traditional drug delivery methods.

Synthesis Reference(s)

Canadian Journal of Chemistry, 53, p. 1103, 1975 DOI: 10.1139/v75-154

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H26O5/c1-3-11(5-13,6-14)9-17-10-12(4-2,7-15)8-16/h13-16H,3-10H2,1-2H3

Upstream product

• 922-63-4 ethylacrolein 
• 50-00-0 formaldehyd 
• 77-99-6 1,1,1-tri(hydroxymethyl)propane 
• 75-75-2 methanesulfonic acid 
• 105-58-8 Diethyl carbonate 
• 123-72-8 butyraldehyde 

Downstream Products

• 67-56-1 methanol 
• 921601-14-1 3,3,7,7-tetra[N-methyl-N-phenyl(acetamide)-2-oxymethyl]-5-oxanonane 
• 921601-16-3 3,3,7,7-tetra[N-ethyl-N-phenyl(acetamide)-2-oxymethyl]-5-oxanonane 
• 928156-24-5 3,3,7,7-tetra[N-benzyl-N-phenyl(acetamide)-2-oxymethyl]-5-oxanonane 

Relevant articles and documents

Urea as an efficient reagent for the synthesis of 3-ethyl-3-(hydroxymethyl)oxetane: A novel component in cationic ring-opening polymerisation

Urea is a very attractive chemical raw material for large-scale production as it combines low cost with virtually unlimited supply and essentially no toxic effects. Here, we present a study on its use in the dehydration of trimethylolpropane with formation of 3-ethyl-3-(hydroxymethyl)oxetane. The reaction consists of carbonylation of trimethylolpropane and subsequent extrusion of carbon dioxide. The first step was run at a temperature of 120-160 °C at a pressure of approximately 300 mmHg for 1-5 h. Most likely, carbamates of TMP constitute the major product. In the latter step, the temperature was increased to 195-215 °C, the pressure was reduced to 10-50 mmHg, and the final product was isolated by distillation. A spiroorthocarbonate of TMP was formed as an unexpected by-product. The process has been demonstrated on a multikilogram scale. Toxicological screening revealed 3-ethyl-3-(hydroxymethyl)oxetane to be irritating to eye but not to skin.

Synthesis and solid-state structure of 2,2,2',2' -(Tetrahydroxymethyl)- dibutylether (Di-TMP), an environmentally benign polymer crosslinker and high-potential additive for lubricants

The crystal structure of the industrially relevant tetrahydroxy ether 2,2,2',2'-(tetrahydroxymethyl)-dibutylether (technically known as di(trimethylol)propane, Di-TMP; C12H26O5) was determined from single-crystal X-ray data at 123 K: monoclinic, space group C2/c (no. 15), a = 20.1202(13), b = 5.8169(4), c = 13.0323(8) A , β = 114.296(3)°, V = 1390.17(16) A3 and Z = 4. The adjacent molecules assemble into a two-dimensional framework in the solid state, linked by two intermolecular O-H...O hydrogen bonds. The compound is characterized via spectroscopic methods and mass spectrometry

A method of manufacturing a polyhydric alcohol ether

[Problem] The purpose of the invention is to react pentaerythritol, trimethylolpropane, or another such polyhydric alcohol with a carbonic acid ester to obtain dipentaerythritol, ditrimethylolpropane, or another such polyhydric alcohol ether at a good yield. [Solution] A method for producing a polyhydric alcohol ether characterized by the joint use of the following catalyst A and catalyst B when reacting a polyhydric alcohol and a carbonic acid ester and producing a polyhydric alcohol ether of a structure in which the polyhydric alcohol is dehydrated and condensed between molecules. Catalyst A: one or more compounds selected from the group consisting of compounds containing an alkali metal, compounds containing an alkaline earth metal, amines or salts thereof or complexes thereof, and semicarbazides or salts thereof. Catalyst B: one or more compounds selected from the group consisting of compounds containing boron, compounds containing titanium, and compounds containing zirconium.

Process for the manufacture of di-TMP

A method of making di-TMP includes reacting TMP and a dialkyl carbonate in the presence of a base catalyst in a reaction medium to form an oxetane of TMP in the reaction medium; providing additional TMP and an acid catalyst to the reaction mixture and reacting the oxetane in situ with the additional TMP to produce di-TMP; and recovering di-TMP. The process may be carried out in sequential reaction zones by feeding the reaction medium forward or carried out sequentially in a single reactor. Preferably, one or all of the following conditions are met: (i) said acid catalyst is a strong acid catalyst or (ii) said base catalyst is a strong base catalyst; or (iii) the molar ratio of TMP/dialkyl carbonate employed in the method is greater than 2.5.

PROCESS FOR PRODUCTION OF DITRIMETHYLOLPROPANE

Provided is a method for producing di-TMP by reacting n-butyl aldehyde (NBD), formaldehyde and a base, said method including a first step of reacting the NBD, formaldehyde (1) and a base (I) to obtain a reaction mixture solution containing trimethylolpropane (TMP), di-TMP and 2-ethyl-2-propenal (ECR); a second step of distilling the reaction mixture solution to recover the ECR therefrom; and a third step of sequentially adding the ECR recovered by distillation, and adding at least one of a base (II) and formaldehyde (2), to the reaction mixture solution from which the ECR has been recovered by distillation, and thereby allowing a reaction for production of the di-TMP to proceed gradually, in which TMP is added in any one of the first to third steps or in plural steps of the first to third steps.

METHOD FOR PRODUCING DITRIMETHYLOLPROPANE

The present invention provides a method for producing ditrimethylolpropane which is characterized by the following (1) and (2): (1) a distillation still residue separated from purified trimethylolpropane is subjected to re-distillation under specific conditions to obtain a ditrimethylolpropane-containing solution having given contents of bis-TMP and tri-TMP; and (2) when subjecting the ditrimethylolpropane-containing solution to crystallization with an organic solvent, the crystallization is initiated under pressure at a temperature exceeding a boiling point of the organic solvent as measured under normal pressures, and the resulting crystallization product solution is cooled at a temperature drop rate of 2° C./min or less. According to the above method, it is possible to produce a high-purity ditrimethylolpropane from a distillation still residue obtained upon production of trimethylolpropane in a simple, industrially useful manner.

PROCESS FOR PRODUCTION OF DITRIMETHYLOLPROPANE

The present invention provides a method for producing ditrimethylolpropane including reacting n-butyraldehyde with formaldehyde in the presence of a base catalyst to thereby produce trimethylolpropane and ditrimethylolpropane, wherein the method includes (I) a step of reacting n-butyraldehyde with formaldehyde (1) in the presence of a base catalyst (1), to thereby produce a reaction mixture containing trimethylolpropane, ditrimethylolpropane, and 2-ethyl-2-propenal; (II) a step of recovering 2-ethyl-2-propenal through distillation of the produced reaction mixture; and (III) a step of adding, to a distillation residue obtained through recovery of 2-ethyl-2-propenal, the recovered 2-ethyl-2-propenal and formaldehyde (2), and optionally a base catalyst (2), to thereby allow reaction for production of ditrimethylolpropane to proceed, wherein the amounts of formaldehyde (I) and the base catalyst (1) supplied in step I and formaldehyde (2) and the base catalyst (2) supplied in step II are controlled to specific amounts, to thereby effectively produce ditrimethylolpropane. According to the present invention, the yield of di-TMP is considerably increased, and the amount of bis-TMP by-produced can be considerably reduced with respect to the amount of di-TMP (i.e., a product of interest) produced; that is, di-TMP can be effectively produced in an industrially advantageous manner.

Method for producing ditrimethylolpropane

In the method of producing ditrimethylolpropane of the present invention, the distillation still residue obtained in the production of trimethylolpropane is subjected to crystallizing treatment while strictly regulating the amount of organic solvent to be used, the crystallization temperature and the crystallization time within the specific ranges. With the method of the present invention, a highly pure di-TMP is obtained only by a single operation of the crystallization.

Process for recovering ditrimethylolpropane

The present invention provides processes for recovering ditrimethylolpropane from a still residue obtained by extracting and then distilling off trimethylolpropane from a reaction solution obtained by reacting n-butyraldehyde with formaldehyde in the presence of a basic catalyst.One process comprises acid decomposition of formals in the still residue.A second process comprises removal from the still residue of components having a higher boiling point than that of ditrimethylolpropane followed by crystallization of the resultant product.