Isobornyl acrylate

Structural formula
	(all- R ) -Isobornyl acrylate (top) and (all- S ) -Isobornyl acrylate (bottom)
General
Surname	Isobornyl acrylate
other names	IBOA; Isobornyl acrylic ester;
Molecular formula	C 13 H 20 O 2
Brief description	colorless liquid with a characteristic odor
External identifiers / databases
EC number	227-561-6
ECHA InfoCard	100.025.055
PubChem	16212506
Wikidata	Q1559594
properties
Molar mass	208.30 g mol −1
Physical state	liquid
density	0.986 g cm −3 (25 ° C)
Melting point	<−35 ° C
boiling point	119–121 ° C (20 hPa )
solubility	almost insoluble in water (19.8 mg l −1 at 20 ° C); very soluble in alcohol and ether; soluble in other organic solvents;
Refractive index	1.476 (20 ° C)
safety instructions
H and P phrases	H: 315-319-335-411
	P: 261-273-305 + 351 + 338
Toxicological data	4890 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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

Isobornyl acrylate (IBOA) is a chemical compound from the group of acrylic acid esters .

Extraction and presentation

The ester can be prepared from (-) - isoborneol , (+) - isoborneol or (±) -isoborneol and acrylic acid . A two-step one-pot process starts with isobornyl acetate of undetermined stereochemistry, which is first hydrolyzed to isoborneol of equally undefined stereochemistry. The second step is transesterification with methyl acrylate (methyl acrylate) to give the target compound.

properties

Isobornyl acrylate is a colorless liquid that is insoluble in water. Polymerization of isobornyl acrylate can occur under the influence of heat or light or on contact with a polymerization initiator .

use

Isobornyl acrylate is a monofunctional monomer and is used as a radiation- curable reactive diluent in the chemical industry.

safety instructions

Oral ingestion of isobornyl acrylate caused tremors, dyspnoea and changes in skin and hair in rats . The LD ₅₀ in rats was 4.890 mg / kg (oral) and in rabbits over 5 g / kg (dermal).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on exo-1,7,7-trimethylbicyclo (2.2.1) hept-2-ylacrylate in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .
↑ ^a ^b ^c data sheet Isobornyl acrylate, technical grade, contains 200 ppm monomethyl ether hydroquinone as inhibitor from Sigma-Aldrich , accessed on January 10, 2012 ( PDF ).
↑ ^a ^b ^c Entry on Isobornyl Acrylate at TCI Europe, accessed on February 26, 2012.
↑ ^a ^b ^c Entry on isobornyl acrylate in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b ^c National Technical Information Service , Vol. OTS0536067.
↑ Knebel, J .; Saal, D .: Method for synthesis and process inhibition of isobornyl (meth) acrylate , Patent US6479696B1 (2002, Röhm GmbH Darmstadt); PDF .
↑ Thomas Brock, Michael Groteklaes, Peter Mischke: Textbook of paint technology . Vincentz Network, 2000, ISBN 978-3-87870-569-7 ( page 208 in Google Book Search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f Entry on exo-1,7,7-trimethylbicyclo (2.2.1) hept-2-ylacrylate in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .

[Sigma-2] ta sheet Isobornyl acrylate, technical grade, contains 200 ppm monomethyl ether hydroquinone as inhibitor from Sigma-Aldrich , accessed on January 10, 2012 ( PDF ).

[tci-3] Entry on Isobornyl Acrylate at TCI Europe, accessed on February 26, 2012.

[chemid-4] Entry on isobornyl acrylate in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[NTIS-5] National Technical Information Service , Vol. OTS0536067.

[6] Knebel, J .; Saal, D .: Method for synthesis and process inhibition of isobornyl (meth) acrylate , Patent US6479696B1 (2002, Röhm GmbH Darmstadt); PDF .

[buch-7] Thomas Brock, Michael Groteklaes, Peter Mischke: Textbook of paint technology . Vincentz Network, 2000, ISBN 978-3-87870-569-7 ( page 208 in Google Book Search).