2,2,4-trimethyl-1,3-pentanediol monoisobutyrate

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Structural formula
Structural formulas from Texanol
Mixture of the two monoisobutyric acid esters of 2,2,4-trimethylpentane-1,3-diol. Both esters are also racemates; the stereochemistry is not given here.
General
Surname 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate
other names
  • Texanol
  • Trimethylpentanediol isobutyrate
  • Isobutyric acid, monoester with 2,2,4-trimethylpentane-1,3-diol
  • 2-methylpropionic acid-2,2,4-trimethyl-1,3-pentanediester
  • TMPD-MIB
  • TRIMETHYL HYDROXYPENTYL ISOBUTYRATE ( INCI )
Molecular formula C 12 H 24 O 3
Brief description

colorless liquid with a faint characteristic odor

External identifiers / databases
CAS number 25265-77-4
EC number 246-771-9
ECHA InfoCard 100.042.505
PubChem 6490
ChemSpider 6245
Wikidata Q2575511
properties
Molar mass 216.32 g mol −1
Physical state

liquid

density

0.95 g cm −3

Melting point

−50 ° C

boiling point

244 ° C

Vapor pressure
  • 1.33 Pa (20 ° C)
  • 0.6 Pa (20 ° C)
solubility

very sparingly soluble in water: 0.5–0.858 g l −1 (18–22 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

3200 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is a mixture of several chemical compounds from the group of ester alcohols. It is also an ester of isobutyric acid .

The mixture of substances was brought onto the market in 1961 by Eastman Chemical under the brand name "Texanol".

Extraction and presentation

2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate can be prepared starting from isobutanal .

Structural isomerism and stereoisomers

Since Texanol is a monoester of racemic 2,2,4-trimethyl-1,3-pentanediol with isobutyric acid , apart from minor impurities (2,2,4-trimethyl-1,3-pentanediol and its diisobutyric acid ester ) it contains a total of four different ones Ester. The ( RS ) - (±) -ester [1: 1 mixture of two substances, the ( R ) -enantiomer and the ( S ) -enantiomer] - is obtained by esterification of the primary hydroxyl group of the diol :

  • ( R ) -enantiomer

  • ( S ) -enantiomer

Furthermore, a second ( RS ) - (±) -ester [1: 1 mixture of two substances, the ( R ) -enantiomer and ( S ) -enantiomer] is produced - obtained by esterification of the secondary hydroxyl group of the diol:

  • ( R ) -enantiomer

  • ( S ) -enantiomer

use

2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is used as a coalescing agent (film-forming aid) for latex paints . The annual production volume in 1995 was almost 100,000 t.

Individual evidence

  1. ↑ Entry on TRIMETHYL HYDROXYPENTYL ISOBUTYRATE in the CosIng database of the EU Commission, accessed on June 22, 2020.
  2. ↑ a b c Entry on 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate in the GESTIS substance database of the IFA , accessed on August 31, 2015(JavaScript required) .
  3. ↑ a b Texanol . In: Chemical & Engineering News . tape 39 , no. 48 , November 27, 1961, pp. 71 , doi : 10.1021 / cen-v039n048.p071 ( PDF ). Also: now Available! Linear Alpha Olefins in Commercial Quantities . In: Chemical & Engineering News Archive . tape

     41 , no. 10 , March 11, 1963, ISSN  0009-2347 , pp. 35 , doi : 10.1021 / cen-v041n010.p035 . We call it Texanol . In: Chemical & Engineering News Archive . tape
     41 , no. 10 , March 11, 1963, ISSN  0009-2347 , pp. 18 , doi : 10.1021 / cen-v041n010.p018 .
  4. ↑ a b c d e OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Propanoic acid, 2-methyl-, monoester with 2,2,4-trimethyl-1,3-pentanediol , accessed on September 1 2015.
  5. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of isobutyric acid, monoester with 2,2,4-trimethylpentane-1,3-diol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on September 1, 2015 , is reproduced from a self-classification by the distributor .
  6. ↑ Eastman Texanol ester alcohol - The premier coalescent .
  7. ↑ Patent DE10207747 : Process for the production of 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate or 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate-containing mixtures. Registered on February 22, 2002 , published on September 5, 2002 , applicant: BASF , inventor: Frank Funke, Klaus Breuer, Detlef Kratz, Ralf Boehling, Helmut Horn. ‌
  8. ↑ C.-C. Lin, RL Corsi: Texanol® ester alcohol emissions from latex paints: Temporal variations and multi-component recoveries . In: Atmospheric Environment . tape 41 , no. 15 May 2007, p. 3225–3234 , doi : 10.1016 / j.atmosenv.2006.07.057 ( PDF ).