Structure of 101-87-1
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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. : | 101-87-1 |
| Formula : | C18H22N2 |
| M.W : | 266.38 |
| SMILES Code : | C1(NC2CCCCC2)=CC=C(NC3=CC=CC=C3)C=C1 |
| English Name : | N1-Cyclohexyl-N4-phenylbenzene-1,4-diamine |
| MDL No. : | MFCD00046341 |
| InChI Key : | ZRMMVODKVLXCBB-UHFFFAOYSA-N |
| Pubchem ID : | 92093 |
* 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 hydrogenchloride; sodium nitrite |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With Perbenzoic acid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With acetic acid; platinum at 120℃; Hydrogenation; | ||
| With nickel at 200 - 220℃; Hydrogenation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With platinum on activated charcoal at 160℃; Hydrogenation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With nickel at 60 - 100℃; Hydrogenation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With K3Fe(CN)6 in an alkaline medium | ||
| With silver(II) oxide |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| der Photooxidation in Cyclohexan; | ||
| der Photooxidation in Cyclohexan; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Cycloheyl-4-nitro-anilin, Cyclohexanon, PdCl; | ||
| N-Phenyl-p-phenylendiamin, Cyclohexanon/Zn/HCO2H; | ||
| N-Phenyl-p-phenylendiamin (I), Cyclohexanon, Zn-Pulver/HCO2H; |
| 4-Nitro-diphenylamin + Cyclohexanon + H2 <NiCr2O3; Autoklav>; | ||
| 4-Nitrodiphenylamin, Cyclohexanon, H2, Adkins-Katalysator; | ||
| 4-Nitro-N-nitroso-diphenylamin, Cyclohexanon, H2 (Pt), 100at, 160grad; | ||
| 4-Nitrodiphenylamin, entspr. Keton, H2; | ||
| Nitro-diphenylamin, Alkyl./H2; | ||
| p-Nitrodiphenylamin, Keton, H2; | ||
| Examples of N-substituted-p-phenylenediamines which may be prepared according to the present invention include ... N-decyl-N'-phenyl-p-phenylenediamine, N-cyclooctyl-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, N-methylcyclohexyl-N'-phenyl-p-phenylenediamine, and ... | ||
| EXAMPLES OF AMINE ANTIOXIDANTS ... 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 4-(p-Toluene-sulfonamido)-diphenylamine N,N'-Dimethyl-N,N'-di-sec.-butyl-p-phenylenediamine 4-Isopropoxy-diphenylamine ... | ||
| Examples of amine antioxidants ... 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 4-(p-toluene-sulfonamido)-diphenylamine N,N'-dimethyl-N,N'-di-sec.-butyl-p-phenylenediamine diphenylamine 4-isopropoxy-diphenylamine ... | ||
| EXAMPLES OF AMINE ANTIOXIDANTS ... 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 4-(p-Toluol-sulfonamido)-diphenylamine N,N'-dimethyl-N,N'-di-sec.-butyl-p-phenylenediamine 4-Isopropoxy-diphenylamine ... | ||
| 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'-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. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 63% | Stage #1: N-cyclohexyl-N'-phenyl-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: 63 percent / ethanol / 25 °C 2.1: 53 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: 63 percent / ethanol / 25 °C 2.1: 11 percent / 150 - 155 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With methanesulfonic acid In toluene | 5 Preparation of N-phenyl-N'-cyclohexyl-p-phenylenediamine EXAMPLE 5 Preparation of N-phenyl-N'-cyclohexyl-p-phenylenediamine Into a three neck 500 ml flask equipped with a thermometer, stirrer, Dean Stark trap and condenser was charged 18.4 grams of N-phenylquinoneimine, 150 ml toluene, 19.9 cyclohexylamine and 5 drops methanesulfonic acid. The reaction was conducted at 110°C. for 1.5 hours after which time the product was washed with 200 ml water containing 10 grams of Na2 S2 O4. The product was decanted, filtered and stripped at a pot temperature of 100°C. at 4 mm Hg. 27 grams of N-phenyl-N'-cyclohexyl-p-phenylenediamine were recovered. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 94% | With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; sodium t-butanolate In toluene at 110℃; for 19h; Inert atmosphere; chemoselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 45% | With Pd/C; sodium formate In toluene at 100℃; for 24h; Inert atmosphere; |

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