Tripropylamine

Structural formula
General
Surname	Tripropylamine
other names	Tri- n propylamine; N, N -dipropylpropan-1-amine ( IUPAC ); TPA;
Molecular formula	C 9 H 21 N
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
EC number	203-047-7
ECHA InfoCard	100.002.771
PubChem	7616
ChemSpider	7334
Wikidata	Q1637944
properties
Molar mass	143.27 g mol −1
Physical state	liquid
density	0.75 g cm −3 (20 ° C)
Melting point	−93 ° C
boiling point	156 ° C
Vapor pressure	4.3 h Pa (20 ° C)
solubility	very sparingly soluble in water (0.75 g l −1 at 25 ° C); soluble in ethanol and diethyl ether ;
Refractive index	1.4181 (20 ° C)
safety instructions
H and P phrases	H: 226-301 + 311 + 331-314-335-412
	P: 261-273-280-301 + 310-305 + 351 + 338-310
Toxicological data	96 mg kg −1 ( LD 50 , rat , oral ) ; 431 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 5.1 mg kg −1 / 4h ( LD 50 , rat , inh. ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Tripropylamine (according to IUPAC nomenclature: N, N -dipropylpropan-1-amine , also tri- n -propylamine ) is an organic-chemical compound from the group of tertiary aliphatic amines .

Extraction and presentation

The large-scale production of tripropylamine takes place in a two-stage process. First, n- propanol is reacted with ammonia in the gas phase over a copper- or nickel-containing heterogeneous catalyst at temperatures from 130 to 250 ° C. and pressures generally from 1 to 220 bar to give a product mixture of mono- , di- and tripropylamine.

In the next step, this is separated by multi-stage distillation and the tri- n- propylamine that has already formed is removed. The remaining di- n -propylamine is then in a second reactor at a with aluminum and zirconium (IV) oxide -supported copper or nickel catalyst , at temperatures of 200 to 260 ° C and pressures of 60 to 150 bar to Tri - n -propylamine and ammonia implemented. Unreacted n -propanol, ammonia, and monopropylamine is recycled to the first reaction stage.

The reactors used are mostly tube bundle reactors with a circulating gas stream and a fixed bed , in which molten salts keep the reaction at an almost constant temperature .

properties

Physical Properties

Tripropylamine has a relative gas density of 4.94 (density ratio to dry air at the same temperature and pressure ) and a relative density of the vapor-air mixture of 1.01 (density ratio to dry air at 20 ° C and normal pressure ). In addition, tripropylamine has a vapor pressure of 4.30 hPa at 20 ° C.

Chemical properties

Tripropylamine is a flammable colorless liquid belonging to the group of aliphatic tertiary amines . It is very sparingly soluble in water (0.75 g · l ⁻¹ at 25 ° C) and more easily than water. TPA is difficult or very difficult to volatilize . When heated, it decomposes to toxic nitrosamines and can react dangerously with strong oxidizing agents , acids , hydrogen peroxide , oxidizing substances, chlorinated hydrocarbons , nitriles , oxides , peroxides and phenols . At 20 ° C., an aqueous solution of 2.6 g / l has a pH value of 11.4.

use

Tripropylamine (TPA) is an important chemical intermediate in the manufacture of dyes , catalysts and corrosion inhibitors . It is also used in the pharmaceutical and cosmetics industries . Furthermore, TPA has proven itself in the production of quats that are used as phase transfer catalysts .

safety instructions

Tripropylamine is mainly absorbed through the airways and skin . Ingestion can cause severe irritation to the skin and mucous membranes . No information is known about reproductive toxicity , mutagenicity or carcinogenicity . The ignition temperature is 180 ° C. The substance therefore falls into temperature class T4. With a flash point of 35 ° C, tripropylamine is considered to be relatively easily flammable. In addition, TPA has a lower explosion limit of 0.7 vol% at 42 g / cm ³ and an upper explosion limit of 5.6 vol% at 335 g / m ³ .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on tripropylamine in the GESTIS substance database of the IFA , accessed on January 22, 2019(JavaScript required) .
↑ ^a ^b David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 562 ( limited preview in Google Book search).
↑ ^a ^b ^c Kevin Huyghe, Steven Brughmans, Falk Simon, Johann-Peter Melder, Peter Raatz: Process for the production of tri-n-propylamine (TPA). In: Google Patents. BASF SE, June 30, 2010, accessed on January 23, 2019 (German, English, French).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on tripropylamine in the GESTIS substance database of the IFA , accessed on January 22, 2019(JavaScript required) .

[David_R._Lide-2] David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 562 ( limited preview in Google Book search).

[:0-3] Kevin Huyghe, Steven Brughmans, Falk Simon, Johann-Peter Melder, Peter Raatz: Process for the production of tri-n-propylamine (TPA). In: Google Patents. BASF SE, June 30, 2010, accessed on January 23, 2019 (German, English, French).