Acetyl tributyl citrate

Structural formula
General
Surname	Acetyl tributyl citrate
other names	Tributyl- O- acetyl citrate; O- acetylcitric acid tributyl ester; Tributyl-2-acetyl citrate; Tributyl acetyl citrate; TBAC; Acetyl tributyl citrate; ATBC; Acetyl Tributyl Citrate ( INCI name );
Molecular formula	C 20 H 34 O 8
Brief description	colorless liquid
External identifiers / databases
EC number	201-067-0
ECHA InfoCard	100,000,971
PubChem	6505
Wikidata	Q4673294
properties
Molar mass	402.48 g mol −1
Physical state	liquid
density	1.05 g cm −3
Melting point	−80 ° C
boiling point	170–173 ° C (at 1 hPa); 331 ° C at 976.4 hPa;
Vapor pressure	0.07 hPa (20 ° C); 17.9 hPa at 20 ° C; 55.2 hPa at 55 ° C;
solubility	practically insoluble in water (5 mg / L at 20 ° C); soluble in ethanol and other organic solvents;
Refractive index	1.443 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 31,500 mg kg −1 ( LD 50 , rat , oral ) ; > 4000 mg kg −1 ( LD 50 , mouse , intraperitoneal ) ;
	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

Acetyl tributyl citrate is a chemical compound from the group of carboxylic acid esters .

Extraction and presentation

Acetyl tributyl citrate can be obtained by the catalytic synthesis of tributyl citrate with acetic anhydride .

properties

Acetyl tributyl citrate is a flammable, hardly inflammable, colorless liquid with a slightly sweet odor that is practically insoluble in water.

use

Acetyl tributyl citrate is used as a biologically safe plasticizer for PVC and other polymers to replace some phthalates that were banned in early 2015 . In particular, it can be used as a replacement for DEHP and DINP . According to studies, very little is transferred from PVC film to food. However, there is little migration from PVC plastic dishes into liquids such as milk. The compound is also used as a plasticizer for the PVDC / PVC copolymer . In the cosmetics sector it is used for the production of nail polishes . Acetyl tributyl citrate reduces the hardness and thus the brittleness of the film and gives the film more elasticity. Furthermore, acetyl tributyl citrate facilitates the evaporation of solvents, e.g. B. ethyl acetate , in nail polish.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry for CAS no. 77-90-7 in the GESTIS substance database of the IFA , accessed on December 30, 2015(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g data sheet Tributyl O-acetylcitrate, 98% from Sigma-Aldrich , accessed on December 30, 2015 ( PDF ).
↑ ^a ^b tecnosintesi.com: ATBC, Acetyl Tributyl Citrate, CAS number: 77-90-7 - Tecnosintesi SpA, Raw Materials in bulk , accessed on December 30, 2015.
↑ globethesis.com: Catalytic Synthesis Of Tri-n-butyl Citrate And Acetyl Tri-n-butyl Citrate , accessed December 30, 2015.
↑ Britt E. Erickson: Regulators And Retailers Raise Pressure On Phthalates , Chemical & Engineering News 93 (25), 2015, pp. 11-15.
↑ V. Lajqi-Makolli, M. Kerolli-Mustafa, I. Malollari, J. Lajqi: Migration of di- (2-ethylhexyl) adipate (DEHA) and acetyl tributyl citrate (ATBC) Plasticizers from PVC movie into the food stimulant of isooctane. In: Materials Science and Technology. 46, 2015, p. 16, doi : 10.1002 / mawe.201400256 .
↑ Victor O. Sheftel: Indirect Food Additives and Polymers Migration and Toxicology . CRC Press, 2000, ISBN 978-1-56670-499-1 , pp. 194 ( limited preview in Google Book search).
↑ Kenichi Nara, Kazusa Nishiyama, Hideaki Natsugari, Akira Takeshita, Hideyo Takahashi: Leaching of the Plasticizer, Acetyl Tributyl Citrate: (ATBC) from Plastic Kitchen Wrap. In: JOURNAL OF HEALTH SCIENCE. 55, 2009, p. 281, doi : 10.1248 / jhs.55.281 .
^ Kettil Svensson: Packaging Materials and Cookware for Food Contact at High Temperatures . Nordic Council of Ministers, 1993, ISBN 978-92-9120-380-2 , pp. 15 ( limited preview in Google Book search).
↑ Entry on acetyl tributyl citrate. In: Römpp Online . Georg Thieme Verlag, accessed December 30, 2015.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry for CAS no. 77-90-7 in the GESTIS substance database of the IFA , accessed on December 30, 2015(JavaScript required) .

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet Tributyl O-acetylcitrate, 98% from Sigma-Aldrich , accessed on December 30, 2015 ( PDF ).

[tecnosintesi.com-3] tecnosintesi.com: ATBC, Acetyl Tributyl Citrate, CAS number: 77-90-7 - Tecnosintesi SpA, Raw Materials in bulk , accessed on December 30, 2015.

[globethesis.com-4] thesis.com: Catalytic Synthesis Of Tri-n-butyl Citrate And Acetyl Tri-n-butyl Citrate , accessed December 30, 2015.

[5] Britt E. Erickson: Regulators And Retailers Raise Pressure On Phthalates , Chemical & Engineering News 93 (25), 2015, pp. 11-15.

[DOI10.1002/mawe.201400256-6] V. Lajqi-Makolli, M. Kerolli-Mustafa, I. Malollari, J. Lajqi: Migration of di- (2-ethylhexyl) adipate (DEHA) and acetyl tributyl citrate (ATBC) Plasticizers from PVC movie into the food stimulant of isooctane. In: Materials Science and Technology. 46, 2015, p. 16, doi : 10.1002 / mawe.201400256 .

[Victor_O._Sheftel-7] Victor O. Sheftel: Indirect Food Additives and Polymers Migration and Toxicology . CRC Press, 2000, ISBN 978-1-56670-499-1 , pp. 194 ( limited preview in Google Book search).

[DOI10.1248/jhs.55.281-8] Kenichi Nara, Kazusa Nishiyama, Hideaki Natsugari, Akira Takeshita, Hideyo Takahashi: Leaching of the Plasticizer, Acetyl Tributyl Citrate: (ATBC) from Plastic Kitchen Wrap. In: JOURNAL OF HEALTH SCIENCE. 55, 2009, p. 281, doi : 10.1248 / jhs.55.281 .

[Kettil_Svensson-9] Kettil Svensson: Packaging Materials and Cookware for Food Contact at High Temperatures . Nordic Council of Ministers, 1993, ISBN 978-92-9120-380-2 , pp. 15 ( limited preview in Google Book search).

[RömppOnline-10] Entry on acetyl tributyl citrate. In: Römpp Online . Georg Thieme Verlag, accessed December 30, 2015.