Structure of 4-Isopropylaminodiphenylamine
CAS No.: 101-72-4
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Godlewska, Klaudia ; Białk-Bielińska, Anna ; Rostkowski, Pawel ; Paszkiewicz, Monika ;
Abstract: Tire wear particles are generated during driving a vehicle as a result of friction between tires and road surfaces and are released into environment. Knowledge of their environmental occurrence and fate is still limited. In this study, we investigated the presence of 16 tire wear contaminants (TWCs) and their transformation products in the surface waters, tap water and soils in Poland.The developed extraction methods were used with recoveries in the range of 71–100% (except for 2-methylthio-benzothiazole - 51%) for water samples and in the range of 62–97% for soil samples. Ten TWCs were detected in soil samples, with the highest concentration of benzothiazole (BTH)(387 ng/g). Meanwhile, all analytes were detected in water samples, also with the highest concentration of BTH (326 ng/L). N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine-quinone (6PPD-Q), 1,3-diphenylguanidine (DPG) and BTH were detected in all examined surface waters. P-phenylenediamine-quinones(PPD-Qs)were detected in higher concentrations (1.85–297 ng/l) compared to the parent compounds (0.50–58 ng/l) in surface waters. Conversely, for soil samples, PPDs (0.170–116 ng/g) were more prevalent than PPD-Qs (0.167–4.71 ng/g). 6PPD-Q showed high ecological risks at all surface water sites. This is the first report on the TWCs levels in the environment in Poland.
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Keywords: Tire wear contaminants ; Transformation products ; 6PPD-Q ; Environmental analysis ; Environmental risk assessment
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| CAS No. : | 101-72-4 |
| Formula : | C15H18N2 |
| M.W : | 226.32 |
| SMILES Code : | CC(NC1=CC=C(NC2=CC=CC=C2)C=C1)C |
| English Name : | N1-Isopropyl-N4-phenylbenzene-1,4-diamine |
| MDL No. : | MFCD00026348 |
| InChI Key : | OUBMGJOQLXMSNT-UHFFFAOYSA-N |
| Pubchem ID : | 7573 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With platinum on activated charcoal; isopropyl alcohol at 50 - 150℃; Hydrogenation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With platinum on activated charcoal; isopropyl alcohol at 50 - 150℃; Hydrogenation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With copper oxide-chromium oxide at 160℃; Hydrogenation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With platinum on activated charcoal; isopropyl alcohol at 50 - 150℃; Hydrogenation; | ||
| With hydrogenchloride; sodium cyanoborohydride 1) methanol; 2) methanol, 16 h; Yield given. Multistep reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With K3Fe(CN)6 in an alkaline medium |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | at 60℃; for 4h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With oxygen at 35℃; Irradiation; study of the retardant efficiency of I on rate of oxidation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Rk. m. O2: Kinetik; | ||
| Oxidationshemmung v. n-C15H32, Inhibitionskonst.; | ||
| Oxid.: Inhibierungskonst.; |
| Rk. m. 2,2'-Azoisobuttersaeuredinitril/C6H5C2H5; | ||
| der Loeschung von Singulett-Sauerstoff (1Δg) in Loesung bei 25grad (Table 6); | ||
| Rk. Antiozonkonstant in CCl4; 25grad; K=12E-6 dm3/mol; | ||
| Rk. mit Cumol-peroxidradikalen; Kinetik; k, E, Desaktivierungskoeff.; | ||
| Rk.m. O3; | ||
| Rk.mit Cumolperoxidradikal: Kinetik (Tab.1); |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| The following phenyldiamines are particularly preferred: N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6-PPD), N-(isopropyl)-N'-phenyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-ditolyl-p-phenylenediamine and N'-phenyl-N'-tolyl-p-phenylenediamine, | ||
| Examples of N-substituted-p-phenylenediamines which may be prepared according to the present invention include ... N-ethyl-N'-phenyl-p-phenylenediamine, N-propyl-N'-phenyl-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-n-butyl-N'-phenyl-p-phenylenediamine, ... | ||
| EXAMPLES OF AMINE ANTIOXIDANTS ... N,N'-Bis(1-methyl-heptyl)-p-phenylenediamine N,N'-Dicyclohexyl-p-phenylenediamine N,N'-Diphenyl-p-phenylenediamine N,N'-Di-(naphthyl-2-)-p-phenylenediamine N-Isopropyl-N'-phenyl-p-phenylenediamine N-(1,3-Dimethyl-butyl)-N'-phenyl-p-phenylenediamine N-(1-Methyl-heptyl)-N'-phenyl-p-phenylenediamine N-Cyclohexyl-N'-phenyl-p-phenylenediamine ... |
| Examples of amine antioxidants ... N,N'-bis(1-methyl-heptyl)-p-phenylenediamine N,N'-dicyclohexyl-p-phenylenediamine N,N'-diphenyl-p-phenylenediamine N,N'-di-(naphthyl-2-)-p-phenylenediamine N-isopropyl-N'-phenyl-p-phenylenediamine N-(1,3-dimethyl-butyl)-N'-phenyl-p-phenylenediamine N-(1-methyl-heptyl)-N'-phenyl-p-phenylenediamine N-cyclohexyl-N'-phenyl-p-phenylenediamine ... | ||
| EXAMPLES OF AMINE ANTIOXIDANTS ... N,N'-Bis(1-methyl-heptyl)-p-phenylenediamine N,N'-Dicyclohexyl-p-phenylenediamine N,N'-Diphenyl-p-phenylenediamine N,N'-Di-(naphthyl-2-)-p-phenylenediamine N-Isopropyl-N'-phenyl-p-phenylenediamine N-(1,3-dimethyl-butyl)-N'-phenyl-p-phenylenediamine N-(1-Methyl-heptyl)-N'-phenyl-p-phenylenediamine N-Cyclohexyl-N'-phenyl-p-phenylenediamine ... | ||
| Illustrative examples of satisfactory N-alkyl-N'-phenyl-phenylenediamines are: N-methyl-N'-phenyl-p-phenylenediamine N-ethyl-N'-phenyl-p-phenylenediamine N-propyl-N'-phenyl-p-phenylenediamine N-isopropyl-N'-phenyl-p-phenylenediamine N-butyl-N'-phenyl-p-phenylenediamine N-isobutyl-N'-phenyl-p-phenylenediamine N-sec.butyl-N'butyl-N'-phenyl-p-phenylenediamine N-n-pentyl-N'-phenyl-p-phenylenediamine N-n-hexyl-N'-phenyl-p-phenylenediamine ... | ||
| A method for producing vinyl norbornene as claimed in claim 1, in which said p-phenylenediamine compound is a member selected from the group consisting of: ... N,n'-bis(β-nitro-α-phenylethyl)-p-phenylenediamine, N,n'-bis-p-diphenyl-p-phenylenediamine, N,n'-di-o-tolyl-p-phenylenediamine, N,n'-di-β-naphthyl-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-butyl-N'-benzyl-p-phenylenediamine, and N-cyclohexyl-N'-phenyl-p-phenylenediamine. | ||
| N-phenyl -N'-cyclohexyl-p-phenylenediamine; N-phenyl-N'-sec-butyl-p-phenylenediamine; N-phenyl-N'-isopropyl-p-phenylenediamine; N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine; N,N'-bis-(1,4-dimethylpentyl)-p-phenylenediamine; N,N'-diphenyl-p-phenylenediamine; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 90 % Spectr. 2: 10 % Spectr. | With hydrogen at 120℃; for 5h; | |
| 1: 49 % Spectr. 2: 51 % Spectr. | With hydrogen at 120℃; for 5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99% | With magnesium sulfate; silver(l) oxide In toluene for 20h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 67% | Stage #1: N-phenyl-N'-isopropyl-p-phenylenediamine With magnesium sulfate; silver(l) oxide In toluene at 25℃; for 15h; Stage #2: prop-2-ene-1-thiol In ethanol at 25℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1.1: Ag2O; MgSO4 / toluene / 15 h / 25 °C 1.2: 67 percent / ethanol / 25 °C 2.1: 54 percent / 150 - 155 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1.1: Ag2O; MgSO4 / toluene / 15 h / 25 °C 1.2: 67 percent / ethanol / 25 °C 2.1: 11 percent / 150 - 155 °C |