1-isopropyl-2,2-dimethyltrimethylene diisobutyrate

Structural formula
1: 1 mixture of two enantiomers
General
Surname	1-isopropyl-2,2-dimethyltrimethylene diisobutyrate
other names	2,2,4-trimethyl-1,3-pentanediol diisobutyrate Texanol diisobutyrate
Molecular formula	C 16 H 30 O 4
Brief description	colorless liquid with a faint odor
External identifiers / databases
CAS number 6846-50-0 EC number 229-934-9 ECHA InfoCard 100.027.213 PubChem 23284 Wikidata Q27162056
properties
Molar mass	286.41 g mol −1
Physical state	liquid
density	0.945 g cm −3
Melting point	−70 ° C
boiling point	281.5 ° C
Vapor pressure	0.004 hPa (25 ° C)
solubility	practically insoluble in water (11.46 mg l −1 at 25 ° C)
Refractive index	1.434 (20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: 412 P: 273-501
Toxicological data	0.7 mg l −1 ( NOEC ,  Daphnia magna , 21 days ) > 3200 mg / kg ( LD 50 ,  rat ,  oral )
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

1-Isopropyl-2,2-dimethyltrimethylene diisobutyrate is a 1: 1 mixture of two stereoisomeric chemical compounds from the group of carboxylic acid esters .

Extraction and presentation

1-Isopropyl-2,2-dimethyltrimethylene diisobutyrate can be obtained by acid-catalyzed cleavage and esterification of 2,4-diisopropyl-5,5-dimethylmetadioxane . The preparation of isobutyraldehyde and subsequent transesterification of 3-hydroxy-2,2,4-trimethylpentyl isobutyrate is also possible by means of the Claisen-Tiščenko reaction .

properties

1-Isopropyl-2,2-dimethyltrimethylene diisobutyrate is a flammable, hardly inflammable, colorless liquid with a faint odor, which is practically insoluble in water.

use

1-Isopropyl-2,2-dimethyltrimethylene diisobutyrate can be used as a plasticizer (for example in the production of highly plasticized polyvinyl chloride which is crosslinked by gamma radiation). It has also been used as a component in the coating of pressure-sensitive copy paper and has been detected as a component of volatile compounds (VOC) in the air inside new cars.

See also

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

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on 1-isopropyl-2,2-dimethyltrimethylene diisobutyrate in the GESTIS substance database of the IFA , accessed on October 1, 2017(JavaScript required) .
2. ↑ ^{a b} data sheet 2,2,4-trimethyl-1,3-pentanediol diisobutyrate, ≥98.5% from Sigma-Aldrich , accessed on October 1, 2017 ( PDF ).
3. ↑ Registration dossier on 1-isopropyl-2,2-dimethyltrimethylene diisobutyrate (section Long-term toxicity to aquatic invertebrates ) at the European Chemicals Agency (ECHA), accessed on October 1, 2017.
4. ↑ Anna Wypych: Databook of Plasticizers . Elsevier, 2017, ISBN 978-1-927885-15-4 ( books.google.de ).
5. ↑ Patent US4110539 : Process for the preparation of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate. Published August 29, 1978 . ‌
6. ↑ James A. Kent, Tilak V. Bommaraju, Scott D. Barnicki: Handbook of Industrial Chemistry and Biotechnology . Springer, 2017, ISBN 978-3-319-52287-6 , pp. 500 ( Google Books ).
7. ↑ OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Propanoic acid, 2-methyl-, 2,2-dimethyl-1- (1-methylethyl) -1,3-propanediyl ester , accessed October 1 2017.
8. ↑ Werner Baumann, Herberg-Liedtke: Paper chemicals: data and facts on environmental protection . Springer-Verlag, 2013, ISBN 978-3-642-58040-6 , pp. 555 ( books.google.de ).
9. ↑ Wolfgang Legrum: Fragrances, between stench and fragrance: Occurrence, properties and use of fragrances and their mixtures . Springer-Verlag, 2015, ISBN 978-3-658-07310-7 , pp. 181 ( books.google.de ).