6PPD

6PPD
Names
	IUPAC name N-(1,3-dimethylbutyl)-N'-phenyl-1,4-benzenediamine
	Other names N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine; 6PPD; DMBPPD;
Identifiers
CAS Number	793-24-8;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1558796;
ChemSpider	12553;
ECHA InfoCard	100.011.222
EC Number	212-344-0;
PubChem CID	13101;
UN number	3077
CompTox Dashboard (EPA)	DTXSID9025114 ;
	InChI InChI=1S/C18H24N2/c1-14(2)13-15(3)19-17-9-11-18(12-10-17)20-16-7-5-4-6-8-16/h4-12,14-15,19-20H,13H2,1-3H3 Key: ZZMVLMVFYMGSMY-UHFFFAOYSA-N;
	SMILES CC(C)CC(C)NC1=CC=C(C=C1)NC2=CC=CC=C2;
Properties
Chemical formula	C18H24N2
Molar mass	268.404 g·mol−1
Appearance	brown or violet solid powder
Density	1.07
Melting point	45 °C (113 °F; 318 K)
Boiling point	260 °C (500 °F; 533 K)
log P	3.972
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H317, H360, H400, H410
GHS precautionary statements	P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+312, P302+352, P308+313, P321, P330, P333+313, P363, P391, P405, P501
Flash point	204 °C (399 °F; 477 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

6PPD is an organic chemical used as an antiozonant in rubber tires. It is one of several p-phenylenediamine (PPD) additives used to protect various rubber materials.[1] 6PPD is prepared by reductive amination of methyl isobutyl ketone with 4-aminodiphenylamine.[2]

A 2020 study found that 6PPD released from vehicle tires gets converted by ozone to a previously unknown quinone analog 6PPD-quinone:

and that 6PPD-quinone is the toxic chemical in storm water runoff responsible for killing coho salmon before they spawn in freshwater streams.[3][4][5]

The 6PPD-quinone compound has been prepared in quantity for scientific study by chemists at the University of California.[6]

References

Krüger, R H; Boissiére, C; Klein-Hartwig, K; Kretzschmar, H-J (2005). "New phenylenediamine antiozonants for commodities based on natural and synthetic rubber". Food Addit Contam. 22 (10): 968–974. doi:10.1080/02652030500098177. PMID 16227180.
Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a23_365.pub2
Tian, Zhenyu; Zhao, Haoqi; Peter, Katherine T.; Gonzalez, Melissa; Wetzel, Jill; Wu, Christopher; Hu, Ximin; Prat, Jasmine; Mudrock, Emma; Hettinger, Rachel; Cortina, Allan E.; Biswas, Rajshree Ghosh; Kock, Flávio Vinicius Crizóstomo; Soong, Ronald; Jenne, Amy; Du, Bowen; Hou, Fan; He, Huan; Lundeen, Rachel; Gilbreath, Alicia; Sutton, Rebecca; Scholz, Nathaniel L.; Davis, Jay W.; Dodd, Michael C.; Simpson, Andre; McIntyre, Jenifer K. (3 December 2020), "A ubiquitous tire rubber–derived chemical induces acute mortality in coho salmon", Science: eabd6951, doi:10.1126/science.abd6951, PMID 33273063, ... existing TWP [tire wear particle] loading, leaching, and toxicity assessments are clearly incomplete. ... Accordingly, the human health effects of such exposures merit evaluation. ... It is unlikely that coho salmon are uniquely sensitive ...
"Pollution from car tires is killing off salmon on US west coast, study finds". The Guardian. 3 December 2020.
"Scientists solve mystery of mass coho salmon deaths. The killer? A chemical from car tires". Los Angeles Times. 3 December 2020.
Agua, Alon; Stanton, Ryan; Pirrung, Michael (2021-02-04). "Preparation of 2-((4-Methylpentan-2-Yl)amino)-5-(Phenylamino)cyclohexa-2,5-Diene-1,4-Dione (6PPD-Quinone), an Environmental Hazard for Salmon". figshare. doi:10.26434/chemrxiv.13698985.v1. Retrieved 2021-02-05.

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[1] Krüger, R H; Boissiére, C; Klein-Hartwig, K; Kretzschmar, H-J (2005). "New phenylenediamine antiozonants for commodities based on natural and synthetic rubber". Food Addit Contam. 22 (10): 968–974. doi:10.1080/02652030500098177. PMID 16227180.

[2] Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a23_365.pub2

[3] Tian, Zhenyu; Zhao, Haoqi; Peter, Katherine T.; Gonzalez, Melissa; Wetzel, Jill; Wu, Christopher; Hu, Ximin; Prat, Jasmine; Mudrock, Emma; Hettinger, Rachel; Cortina, Allan E.; Biswas, Rajshree Ghosh; Kock, Flávio Vinicius Crizóstomo; Soong, Ronald; Jenne, Amy; Du, Bowen; Hou, Fan; He, Huan; Lundeen, Rachel; Gilbreath, Alicia; Sutton, Rebecca; Scholz, Nathaniel L.; Davis, Jay W.; Dodd, Michael C.; Simpson, Andre; McIntyre, Jenifer K. (3 December 2020), "A ubiquitous tire rubber–derived chemical induces acute mortality in coho salmon", Science: eabd6951, doi:10.1126/science.abd6951, PMID 33273063, ... existing TWP [tire wear particle] loading, leaching, and toxicity assessments are clearly incomplete. ... Accordingly, the human health effects of such exposures merit evaluation. ... It is unlikely that coho salmon are uniquely sensitive ...

[4] "Pollution from car tires is killing off salmon on US west coast, study finds". The Guardian. 3 December 2020.

[5] "Scientists solve mystery of mass coho salmon deaths. The killer? A chemical from car tires". Los Angeles Times. 3 December 2020.

[6] Agua, Alon; Stanton, Ryan; Pirrung, Michael (2021-02-04). "Preparation of 2-((4-Methylpentan-2-Yl)amino)-5-(Phenylamino)cyclohexa-2,5-Diene-1,4-Dione (6PPD-Quinone), an Environmental Hazard for Salmon". figshare. doi:10.26434/chemrxiv.13698985.v1. Retrieved 2021-02-05.

6PPD

See also

References