Diisobutyl phthalate

Structural formula
General
Surname	Diisobutyl phthalate
other names	Diisobutyl phthalate; DIBP; 1,2-Benzene dicarboxylic acid bis (2-methylpropyl) ester;
Molecular formula	C 16 H 22 O 4
Brief description	colorless liquid with a faint odor
External identifiers / databases
EC number	201-553-2
ECHA InfoCard	100.001.412
PubChem	6782
ChemSpider	6524
Wikidata	Q162259
properties
Molar mass	278.35 g mol −1
Physical state	liquid
density	1.04 g cm −3
Melting point	−64 ° C
boiling point	296.5 ° C
Vapor pressure	<1 Pa (20 ° C)
solubility	almost insoluble in water (20 mg l −1 at 20 ° C); soluble in most organic solvents and oils, miscible with other plasticizers and phthalic acid esters;
Refractive index	1.49 (at 20 ° C)
safety instructions
H and P phrases	H: 360Df-410
	P: 201-273-308 + 313-391-501
Authorization procedure under REACH	of particular concern : toxic for reproduction ( CMR ), serious effects on human health are considered probable; subject to approval
Toxicological data	15,000 mg kg −1 ( LD 50 , rat , oral ) ; 0.9 mg l −1 ( LC 50 , Pimephales promelas , 96 hours ) ;
	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

Diisobutyl phthalate (abbreviated DIBP) is an organic chemical compound from the group of phthalates that is mainly used as a plasticizer . It is a colorless liquid with a very faint odor.

Extraction and presentation

The technical production of diisobutyl phthalate takes place in a two-stage synthesis from phthalic anhydride and isobutanol . The first step is rapid alcoholysis to form the phthalic acid half- ester. The second esterification step is slower as an equilibrium reaction and requires the use of acidic catalysts and, in order to complete the conversion, the distillative separation of the water formed.

properties

Physical Properties

Diisobutyl phthalate has a kinematic viscosity of 40.95 mm ² · s ^-1 and its vapors are ten times as heavy as air.

Chemical properties

Diisobutyl phthalate is very stable to light and heat. It has a lower density and melting point than dibutyl phthalate , but has similar properties so that it can be used as a substitute for them.

use

Diisobutyl phthalate has been used in many ways. So it served

as odorless plasticizers for plastics ( PVC , polyvinyl acetate , polyvinyl butyral , cellulose acetate , cellulose nitrate , ethyl cellulose , polyurethane , acrylics , chlorinated rubber and nitrile rubber ) as well as for coatings and polyvinyl acetate water-based adhesives
as an additive (with a content of 60%) to dibenzoyl peroxide-containing hardeners for unsaturated polyester resins
as a marking additive (mixed with nonylphenols ) of heating oils for tax purposes
for the production of titanium catalysts
as a carrier material for odor improvers
as an additive in hydraulic fluids and lubricants
indirectly in the food sector as a flexibilizing component in printing inks for food packaging.

Health hazards

Diisobutyl phthalate is toxic to reproduction and has been classified as Reprotox 1B. On January 13, 2010, diisobutyl phthalate was classified as a substance of very high concern because of this property and was subsequently made subject to authorization . Diisobutyl phthalate was allowed to be used until February 21, 2015. Since no applications for approval have been submitted, the use of diisobutyl phthalate is no longer permitted.

On March 31, 2015, with the delegated directive (EU) 2015/863, diisobutyl phthalate was added to the RoHS substance list. As of July 22, 2019, electrical and electronic devices containing parts with more than 0.1% by weight DIBP in the homogeneous material may no longer be sold in the EU.

Web links

Report on plastics and phthalates with reference to DIBP (PDF file; 217 kB)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on diisobutyl phthalate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ ^a ^b Data sheet diisobutyl phthalate from GisChem, accessed on April 13, 2016.
↑ ^a ^b Data sheet diisobutyl phthalate from Sigma-Aldrich , accessed on March 25, 2011 ( PDF ).
↑ Entry on diisobutyl phthalate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b Entry in the SVHC list of the European Chemicals Agency , accessed on July 7, 2017.
↑ ^a ^b Entry in the register of substances subject to authorization of the European Chemicals Agency , accessed on July 7, 2017.
↑ ^a ^b P.M. Lorz, FK Towae, W. Enke, R. Jäckh, N. Bhargava, W. Hillesheim: Phthalic Acid and Derivatives in Ullmann's Encyclopedia of Industrial Chemistry, 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007 .a20_181.pub2 .
↑ AM Saillenfait, JP Sabaté, F. Gaallissot: Developmental Toxic Effects of Diisobutyl Phthalate, the Methyl-branched Analogue of Di-n-butyl Phthalate, Administered by Gavage to Rats. In: Toxicology Letters . 165, 2016, pp. 39-46, doi : 10.1016 / j.toxlet.2006.01.013 .
↑ List of accepted authorization applications on the ECHA website , accessed on April 13, 2016.
↑ Commission Delegated Directive (EU) 2015/863 of March 31, 2015 amending Annex II of Directive 2011/65 / EU of the European Parliament and of the Council with regard to the list of substances subject to restrictions (text with EEA relevance ) . OJ L, 32015L0863, June 4, 2015 ( europa.eu [accessed June 28, 2019]).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on diisobutyl phthalate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[GisChem-2] Data sheet diisobutyl phthalate from GisChem, accessed on April 13, 2016.

[Sigma-3] Data sheet diisobutyl phthalate from Sigma-Aldrich , accessed on March 25, 2011 ( PDF ).

[CLP_100.001.412-4] Entry on diisobutyl phthalate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[SVHC-5] Entry in the SVHC list of the European Chemicals Agency , accessed on July 7, 2017.

[Zulassungspflicht-6] Entry in the register of substances subject to authorization of the European Chemicals Agency , accessed on July 7, 2017.

[Ullmann-7] P.M. Lorz, FK Towae, W. Enke, R. Jäckh, N. Bhargava, W. Hillesheim: Phthalic Acid and Derivatives in Ullmann's Encyclopedia of Industrial Chemistry, 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007 .a20_181.pub2 .

[8] AM Saillenfait, JP Sabaté, F. Gaallissot: Developmental Toxic Effects of Diisobutyl Phthalate, the Methyl-branched Analogue of Di-n-butyl Phthalate, Administered by Gavage to Rats. In: Toxicology Letters . 165, 2016, pp. 39-46, doi : 10.1016 / j.toxlet.2006.01.013 .

[9] List of accepted authorization applications on the ECHA website , accessed on April 13, 2016.

[10] Commission Delegated Directive (EU) 2015/863 of March 31, 2015 amending Annex II of Directive 2011/65 / EU of the European Parliament and of the Council with regard to the list of substances subject to restrictions (text with EEA relevance ) . OJ L, 32015L0863, June 4, 2015 ( europa.eu [accessed June 28, 2019]).