6PPD

6PPD
Names
	Preferred IUPAC name N1-(4-Methylpentan-2-yl)-N4-phenylbenzene-1,4-diamine
	Other names N-(1,3-dimethylbutyl)-N'-phenyl-1,4-benzenediamine; 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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H317, H360, H410
Precautionary statements	P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P333+P313, 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 that is widely used as an antiozonant and antioxidant in rubber tires.^[1] It is one of several p-phenylenediamine (PPD) additives used to protect various rubber materials.^[2]

Manufacturing[]

6PPD is prepared by reductive amination of methyl isobutyl ketone with 4-aminodiphenylamine.^[3]

Environmental Impact[]

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.^[4]^[5]^[6]

A synthetic route to the 6PPD-quinone has been posted on ChemRxiv.^[7]

References[]

^ U.S. Tire Manufacturers Association (July 15, 2021). "Statement of Sarah E. Amick Vice President EHS&S and Senior Counsel U.S. Tire Manufacturers Association". Committee on Natural Resources Subcommittee on Oversight and Investigations United States House of Representatives.
^ 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. S2CID 10548886.
^ 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, 371 (6525): 185–189, doi:10.1126/science.abd6951, PMID 33273063, S2CID 227281491, ... 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". ChemRxiv. doi:10.26434/chemrxiv.13698985.v1.

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[1] U.S. Tire Manufacturers Association (July 15, 2021). "Statement of Sarah E. Amick Vice President EHS&S and Senior Counsel U.S. Tire Manufacturers Association". Committee on Natural Resources Subcommittee on Oversight and Investigations United States House of Representatives.

[2] 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. S2CID 10548886.

[3] 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

[4] 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, 371 (6525): 185–189, doi:10.1126/science.abd6951, PMID 33273063, S2CID 227281491, ... 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 ...

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

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

[7] 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". ChemRxiv. doi:10.26434/chemrxiv.13698985.v1.

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6PPD

Contents

Manufacturing[]

Environmental Impact[]

See also[]

References[]

Names

Preferred IUPAC name N¹-(4-Methylpentan-2-yl)-N⁴-phenylbenzene-1,4-diamine
Other names N-(1,3-dimethylbutyl)-N'-phenyl-1,4-benzenediamine 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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H317, H360, H410
Precautionary statements	P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P333+P313, 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