4- tert -butylbenzoic acid
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | 4- tert -butylbenzoic acid | |||||||||||||||
other names |
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Molecular formula | C 11 H 14 O 2 | |||||||||||||||
Brief description |
white flakes, white scales, white-almost white crystal powder |
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properties | ||||||||||||||||
Molar mass | 178.23 g mol −1 | |||||||||||||||
Physical state |
firmly |
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density | ||||||||||||||||
Melting point | ||||||||||||||||
boiling point |
280 ° C with decomposition |
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Vapor pressure |
0.057 Pa at 20 ° C |
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solubility | ||||||||||||||||
safety instructions | ||||||||||||||||
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MAK |
Switzerland: 2 mg m −3 (measured as inhalable dust ) |
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Toxicological data | ||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
4- tert- butylbenzoic acid (TBBA or PTBBA) is an alkyl derivative of benzoic acid and is formed during the air oxidation of 4- tert- butyltoluene . The acid is used as a chain termination reagent in polycondensation reactions , its alkaline earth salts as heat stabilizers for PVC .
4- tert- butylbenzoic acid is no longer manufactured in Europe due to its toxicological concern.
presentation
The standard process for the production of 4- tert- butylbenzoic acid is the oxidation of 4- tert- butyltoluene (PTBT) in the liquid phase with atmospheric oxygen under catalysis with cobalt salts , preferably cobalt (II) acetate .
The oxidation of 4- tert- butyltoluene with concentrated nitric acid at 180 ° C is just as obsolete as the oxidation of PTBT with potassium permanganate due to the corrosiveness of hot nitric acid and the nitrous gases generated in large quantities, despite good yields .
properties
4- tert- butylbenzoic acid is usually obtained as a whitish crystalline powder with a weakly aromatic odor, which is soluble in water at a neutral pH value , but is sparingly soluble in acid. The acid dissolves in many organic solvents as well as in alkaline solvents with salt formation.
TBBA has been shown to be reprotoxic in animal experiments and must be handled with appropriate precautionary measures.
use
4- tert -Butylbenzoic acid is used to modify and improve the properties of alkyd resins , as a chain termination reagent in polyester polycondensation, as a nucleating agent for polypropylene and as a starting material for functionalized hydrazides as an extractant for divalent copper salts , and for methyl 4-tert-butyl benzoate as a synthetic building block for Avobenzone .
Salts of 4- tert- butylbenzoic acid with alkali metals such as potassium and with alkaline earth metals such as magnesium , calcium and barium are or were used - mostly as combinations of two salts in liquid form - for the thermal stabilization of flexible soft PVC . The cadmium and lead salts of aromatic and aliphatic carboxylic acids previously used as stabilizers for rigid rigid PVC do not contain any 4- tert- butylbenzoic acid.
Salts of TBBA with amines , such as. B. with diethanolamine as an antioxidant and anti-corrosion agent added cooling lubricants and lubricants .
By hydrogenation on a didymium catalyst consisting mainly of a mixture of lanthanum oxide and neodymium (III) oxide at 400 ° C., 4- tert- butylbenzaldehyde is obtained from TBBA in 80% yield, which itself smells like almond and is a starting compound for the synthesis of Lily of the valley fragrance represents Lilial .
Individual evidence
- ↑ a b Data sheet 4-tert-butylbenzoic acid from Sigma-Aldrich , accessed on August 18, 2015 ( PDF ).
- ↑ a b c d e f Entry on 4-tert-butylbenzoic acid in the GESTIS substance database of the IFA , accessed on August 18, 2015 (JavaScript required)
- ↑ a b Entry on 4-tert-Butylbenzoic Acid at TCI Europe, accessed on August 21, 2015.
- ↑ a b c d e Data sheet 4-tert-butylbenzoic acid for synthesis (PDF) from Merck , accessed on August 18, 2015.
- ↑ a b c d 4-tert-Butylbenzoic Acid, CAS No: 98-73-7, EINECS No: 202-696-3, Summary Risk Assessment Report, Final Report 2009, http://echa.europa.eu/documents / 10162 / ca851d3b-e922-4561-8419-892a746a8d30
- ↑ http://www.ecem.com/msds/PTBBA_EN.pdf (link not available)
- ↑ Entry on 4-tert-butylbenzoic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 98-73-7 or 4-tert-butylbenzoic acid ), accessed on November 2, 2015.
- ↑ GW Hearne, TW Evans, VW Buls, CG Schwarzer: Preparation of tert-Alkylbenzoic Acids by Liquid Phase Catalytic Oxidation . In: Ind. Eng. Chem. Band 47 , no. 11 , 1955, pp. 2311-2313 , doi : 10.1021 / ie50551a035 .
- ↑ Patent US4603220 : Process for the preparation of aromatic monocarboxylic acids from toluene and substituted toluenes. Applied on July 18, 1984 , published July 29, 1986 , applicant: Dynamit Nobel AG, inventor: M. Feld.
- ↑ Nanjing Chemical Plant Jianci Co., Ltd., Studies on Synthesizing P-tert-Butyl Benzoic Acid (II), Nitric acid oxidation method .
- ↑ Nanjing Jianci Chemical Plant Co., Ltd., Studies on Synthesizing P-Tert-Butyl Benzoic Acid (III), Potassium permanganate oxidation method .
- ↑ DA Pashkina, VY Gusev, AV Radushev: Physicochemical properties of 4-tert -butylbenzoic acid N ', N' -dialkylhydrazides . In: Russ. J. Gen. Chem. Band 84 , no. 6 , 2014, p. 1101-1105 , doi : 10.1134 / S1070363214060085 .
- ↑ espa, European Stabilizer Producers Association, Liquid stabilisers ( Memento from July 26, 2015 in the Internet Archive ).
- ↑ Patent US2832742 : Corrosion inhibitor composition. Applied on June 9, 1954 , published April 29, 1958 , applicant: Alox Corp., inventor: CA Weltman.
- ↑ Patent EP101111 : Process and catalytic composition for the preparation of aldehydes, and aldehydes thus prepared. Applied on July 13, 1983 , published on February 22, 1984 , applicant: Shell Internationale Research Maatschaapij BV, inventor: F. Wattimena, HJ Heijman.
- ↑ PN Davey, SA Forsyth, HQN Gunaratne, C. Hardacre, A. McKeown, SEJ McMath, KR Seddon: Synthesis of 3- (4-tert-butylphenyl) -2-propen-1-one, a precursor to Lilial®, via an aldol condensation in an ionic liquid . In: Green Chemistry . tape 7 , 2005, p. 224-229 , doi : 10.1039 / B416021E .