N,N,N',N'-Tetramethyl-1,3-butanediamine

• CAS: 97-84-7
• Catalog Number: ACM97847
• Category: Other Products; Main Products
• Molecular Weight: 144.26
• Molecular Formula: C₈H₂₀N₂
• Synonyms: Tetramethylbutanediamine, NIAX catalyst TMBDA, 1,3-Bis(dimethylamino)butane, Tetramethyl butanediamine, Tetramethylbutane-1,3-diamine, CCRIS 4869, 14740_ALDRICH, N,N,N,N-Tetramethyl-1,3-diaminobutane, N,N,N,N-TETRAMETHYL-1,3-BUTANEDIAMINE, NSC35411, 14740_FLUKA, EINECS 202-610-4, 1,3-Butanediamine, N,N,N,N-tetramethyl-, CID7350, MolPort-003-926-533, NSC 35411, BRN 1698054, N,N,N1,N1-Tetramethyl-1,3-diaminobutane, 1,3-Diaminobutane, N,N,N,N-tetramethyl-, AI3-26039
• IUPAC Name: 1-N,1-N,3-N,3-N-tetramethylbutane-1,3-diamine
• SMILES: CC(CCN(C)C)N(C)C
• InChI Key: AXFVIWBTKYFOCY-UHFFFAOYSA-N
• Boiling Point: 165ºC(lit.)
• Flash Point: 105 °F
• Density: 0.787 g/mL at 25ºC(lit.)
• Appearance: Colorless to Light Yellow Liquid
• EC Number: 202-610-4
• Exact Mass: 144.16300
• Hazard Statements: T
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Packing Group: III
• Safety Description: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .; S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .; S45:In case of accident or if you feel unwell, seek medical advice immediately
• UN Number: 1993
• WGK Germany: 3

Case Study

N,N,N',N'-Tetramethyl-1,3-butanediamine as Catalyst in the Reliable Synthesis of Polymer Curing Agent

Eastwood, Eric. Kansas City Plant (KCP), 2009, 613-8526.

This study detailed the manufacturing process for diphenol-4,4'-methylenebis (phenylcarbamate), a critical blocked diisocyanate curing agent used in crosslinking ethylene/vinyl acetate/vinyl alcohol (VCE) terpolymers. The synthesis relies on the reaction of phenol with methylenebis(4-phenylisocyanate) (MDI) in toluene, with N,N,N',N'-tetramethyl-1,3-butanediamine (TMBDA) serving as the essential amine catalyst.
Small-Scale Reaction Procedures
· A 2-liter glass reactor was loaded with 1195 grams of toluene and 2.8 grams of TMBDA. Next, 140.5 grams of phenol were melted at 150°F and combined with the toluene and TMBDA mixture. The complete melting of phenol took around 60 minutes at this temperature.
· Additionally, 140.5 grams of MDI and 61.1 grams of toluene were combined and placed in an oven at 150°F to facilitate dissolution. This MDI/toluene solution was heated for 60 minutes until it became fully homogeneous, after which it was transferred to a one-liter addition flask.
· While the phenol/TMBDA/toluene mixture was stirred vigorously, the MDI/toluene solution was gradually dripped into the 2-liter reactor. The volume and temperature of the MDI/toluene solution were monitored during the process. About 200 mL of MDI/toluene solution was added to the phenol/TMBDA/toluene solution in 25 min at the average rate of 8 mL/min.

N,N,N',N'-Tetramethyl-1,3-butanediamine as a Key Electrolyte Component for Optimizing Protein Separations in Capillary Zone Electrophoresis

Corradini, Danilo, et al. Chromatographia 73.Suppl 1 (2011): 103-111.

Background Electrolytes (BGEs) for the capillary zone electrophoresis (CZE) of proteins contain one or more anions. This study evaluated the influence of the anionic component of BGEs on the separation performance of proteins. BGEs with 20 mM N,N,N',N'-tetramethyl-1,3-butanediamine (TMBD) were titrated to pH 4.0 or 6.5 with a series of common monoprotic or polyprotic acids (except hydrochloric acid) often used in high performance liquid chromatography (HPLC) or CZE for protein analysis.
TMBD was selected for its ability to minimize protein adsorption onto bare fused-silica capillary walls. Separation performance was assessed using four basic model proteins (pI range: 9.5-11.0; molecular mass range: 12,400-25,000 Da).
Key Findings
· Anion-Dependent Performance: The choice of acid used with TMBD significantly impacted protein migration times and peak shapes, despite identical TMBD concentration.
· Enhanced Performance with Phosphates: While TMBD alone improved separations, the combination of TMBD and DETA in phosphate-containing BGEs yielded superior separation performance at pH 4.0.
· pH Relevance: Performance differences were observed across the tested pH range (4.0 and 6.5), indicating pH-dependent interactions.

Study of N,N,N',N'-tetramethyl-1,3-butanediamine as an effective electrolyte additive

Dell'Aquila, Caterina. Journal of pharmaceutical and biomedical analysis 30.2 (2002): 341-350.

Five tricyclic antidepressants (TADs)-desipriamide, nortriptyline, imipramine, doxepin, and amitriptyline-were separated in a background electrolyte solution using N,N,N,N-tetramethyl-1,3-butanediamine (TMBD) as an additive. Because TADs are similar in structure, mass, and pKa values, their separation by capillary zone electrophoresis requires careful control of parameters such as pH and electrolyte composition. Different concentrations of TMBD (40, 60, 100, and 150 mM) were used at pH 9.5, but only 100 mM TMBD achieved good separation and high efficiency for all TADs. Separation was impossible without the additive at this pH. Before capillary electrophoresis, new bare capillaries were conditioned by rinsing with water, 1 M HCl, water, 1 M NaOH, water, and running buffer for 30 minutes. The running electrolyte solutions were: potassium borate; potassium phosphate; N,N,N',N'-tetramethyl-1,3-butanediamine phosphate; and N,N,N',N'-tetramethyl-1,3-butanediamine phosphate. pH was measured using a glass electrode. All solutions were filtered through a membrane filter and degassed by sonication before use. The running electrolyte was refreshed after three to four runs, and the capillary was rinsed with running electrolyte for 3 minutes before each run.

Excess volumes, excess enthalpies, and vapor-liquid equilibrium studies of mixtures of N,N,N',N'-tetramethyl-1,3-butanediamine

Dahmani, Abdallah, Ilham Mokbel, and Jacques Jose. Fluid phase equilibria 203.1-2 (2002): 193-204.

Experimental data report the excess molar volumes and excess molar enthalpies of binary mixtures of N,N,N',N'-tetramethyl-1,3-butanediamine with either n-heptane or cyclohexane at 298.15 K. The vapor pressures of the same binaries were also measured using a static method at 10 K intervals between 273.15 and 363.15 K. The molar excess Gibbs energies and molar excess enthalpies calculated from the vapor-liquid equilibrium data were used to test the applicability of the group contribution model. In particular, the possibility of analyzing intramolecular effects was tested.
The vapor pressures of n-heptane and cyclohexane were determined by fractionation on a 40-plate column and were found to be consistent with literature values. N,N,N',N'-tetramethyl-1,3-butanediamine (TMBD) was also distilled under nitrogen in the presence of sodium, and its purity was checked by gas chromatography. The excess molar volume was determined based on the density, ρ, measured using a vibrating tube densitometer. The densities of the pure components, ρ (heptane) (g cm) = 0.67943 and ρ (cyclohexane) (g cm) = 0.77418, agree well with literature values. The density of the pure diamine, ρ (TMBD) (g cm) = 0.79714.