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Zinc dithiophosphateFrom Wikipedia, the free encyclopedia

Structure of a monomeric zinc dialkyldithiophosphate

Zinc dialkyldithiophosphates (often referred to as ZDDP) are a family ofcoordination

compoundsinvented byCastrolthat featurezincbound to the anion of dithiophosphoric acid.

These uncharged compounds are not salts. They are soluble in nonpolar solvents, and the longerchain derivatives easily dissolve inmineralandsynthetic oilsused aslubricants. They come

underCAS number[68649-42-3]. In aftermarket oil additives, the percentage of ZDDP ranges

approximately between 2-15%.[1]

The alkyl groups can be branched and linear alkanes between 1-14 carbons length, 2-butyl, pentyl,

hexyl, 1,3-dimethylbutyl, heptyl, octyl, isooctyl (2-ethylhexyl), 6-methylheptyl, 1-methylpropyl,

dodecylphenyl, and others. A mix of zinc dialkyl(C3-C6)dithiophosphates come under CAS number

[84605-29-8]. List of other examples with their CAS numbers ishere.

Contents

1 Coordination chemistry

2 Applications

3 Naming

4 References

5 External links

Coordination chemistry

These species are produced in two steps. Firstphosphorus pentasulfideis treated with

suitablealcoholsto give the dithiophosphoric acid. A wide variety of alcohols can be employed,

which allows the lipophilicity of the final zinc product to be fine-tuned. The resulting

dithiophosphate is then neutralized by addingzinc oxide:

2 (RO)2PS2H + ZnO Zn[(S2P(OR)2]2 + H2O

In Zn[(S2P(OR)2]2, the zinc is tetrahedral. This monomeric compound also exists in equilibrium

with dimers andoligomerscaused by opening of the four-membered ZnS2P ring. Partial

http://en.wikipedia.org/wiki/Coordination_compoundhttp://en.wikipedia.org/wiki/Coordination_compoundhttp://en.wikipedia.org/wiki/Coordination_compoundhttp://en.wikipedia.org/wiki/Coordination_compoundhttp://en.wikipedia.org/wiki/Castrolhttp://en.wikipedia.org/wiki/Castrolhttp://en.wikipedia.org/wiki/Castrolhttp://en.wikipedia.org/wiki/Zinchttp://en.wikipedia.org/wiki/Zinchttp://en.wikipedia.org/wiki/Zinchttp://en.wikipedia.org/wiki/Mineral_oilhttp://en.wikipedia.org/wiki/Mineral_oilhttp://en.wikipedia.org/wiki/Mineral_oilhttp://en.wikipedia.org/wiki/Synthetic_oilhttp://en.wikipedia.org/wiki/Synthetic_oilhttp://en.wikipedia.org/wiki/Synthetic_oilhttp://en.wikipedia.org/wiki/Lubricanthttp://en.wikipedia.org/wiki/Lubricanthttp://en.wikipedia.org/wiki/Lubricanthttp://en.wikipedia.org/wiki/CAS_numberhttp://en.wikipedia.org/wiki/CAS_numberhttp://en.wikipedia.org/wiki/CAS_numberhttp://www.emolecules.com/cgi-bin/search?t=ss&q=68649-42-3&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=68649-42-3&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=68649-42-3&c=1&v=http://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-0http://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-0http://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-0http://www.emolecules.com/cgi-bin/search?t=ss&q=84605-29-8&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=84605-29-8&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=84605-29-8&c=1&v=http://apps.kemi.se/flodessok/floden/kemamne_eng/zinkdialkyl_eng.htmhttp://apps.kemi.se/flodessok/floden/kemamne_eng/zinkdialkyl_eng.htmhttp://apps.kemi.se/flodessok/floden/kemamne_eng/zinkdialkyl_eng.htmhttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Coordination_chemistryhttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Coordination_chemistryhttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Applicationshttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Applicationshttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Naminghttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Naminghttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Referenceshttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Referenceshttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#External_linkshttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#External_linkshttp://en.wikipedia.org/wiki/Phosphorus_pentasulfidehttp://en.wikipedia.org/wiki/Phosphorus_pentasulfidehttp://en.wikipedia.org/wiki/Phosphorus_pentasulfidehttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Zinc_oxidehttp://en.wikipedia.org/wiki/Zinc_oxidehttp://en.wikipedia.org/wiki/Zinc_oxidehttp://en.wikipedia.org/wiki/Oligomerhttp://en.wikipedia.org/wiki/Oligomerhttp://en.wikipedia.org/wiki/Oligomerhttp://en.wikipedia.org/wiki/Oligomerhttp://en.wikipedia.org/wiki/Oligomerhttp://en.wikipedia.org/wiki/Zinc_oxidehttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Phosphorus_pentasulfidehttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#External_linkshttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Referenceshttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Naminghttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Applicationshttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#Coordination_chemistryhttp://apps.kemi.se/flodessok/floden/kemamne_eng/zinkdialkyl_eng.htmhttp://www.emolecules.com/cgi-bin/search?t=ss&q=84605-29-8&c=1&v=http://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-0http://www.emolecules.com/cgi-bin/search?t=ss&q=68649-42-3&c=1&v=http://en.wikipedia.org/wiki/CAS_numberhttp://en.wikipedia.org/wiki/Lubricanthttp://en.wikipedia.org/wiki/Synthetic_oilhttp://en.wikipedia.org/wiki/Mineral_oilhttp://en.wikipedia.org/wiki/Zinchttp://en.wikipedia.org/wiki/Castrolhttp://en.wikipedia.org/wiki/Coordination_compoundhttp://en.wikipedia.org/wiki/Coordination_compoundhttp://en.wikipedia.org/wiki/File:Zn(dtp)2.pnghttp://en.wikipedia.org/wiki/File:Zn(dtp)2.png

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hydrolysis gives the cluster Zn4O[(S2P(OR)2]6, which adopts the structure seen forbasic zinc

acetate.

Zinc diethyldithiophosphate, Zn[(S2P(OEt)2]2, is a polymeric solid consisting of linear chains.[2]

Applications

The main use of ZDDP is inanti-wear additivestolubricantssuch asgreases,gear oils,

andmotor oils, which often contain less than 1% of this additive. It has been reported that

zinc and phosphorus emissions may damagecatalytic convertersand standard

formulations of lubricating oils for gasoline engines now have reduced amounts of the

additive, though diesel engine oils remain at higher levels.[3]

. Crankcase oils with reduced

ZDDP have been cited as causing damage to, or failure of, classic/collector car flat tappet

camshafts and lifters which undergo very high boundary layer pressures and/or shear

forces at their contact faces, and in other regions such as big-end/main bearings, and

piston rings and pins. Rollercamshaftsare more commonly used to reduce camshaft

lobe friction in modern engines. There are additives, such as STP(R) Oil Treatment, and

some racing oils such as Valvoline ZR-1, are available in the retail market with the

necessary amount of ZDDP for engines using increased valvespringpressures. See

"external links" in this article. The same ZDDP compounds serve also ascorrosion

inhibitorsandantioxidants.

Naming

These compounds are widely used and correspondingly have numerous names,

including ZDDP, ZnDTP, and ZDP.

http://en.wikipedia.org/wiki/Zinc_acetatehttp://en.wikipedia.org/wiki/Zinc_acetatehttp://en.wikipedia.org/wiki/Zinc_acetatehttp://en.wikipedia.org/wiki/Zinc_acetatehttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-1http://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-1http://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-1http://en.wikipedia.org/wiki/AW_additivehttp://en.wikipedia.org/wiki/AW_additivehttp://en.wikipedia.org/wiki/AW_additivehttp://en.wikipedia.org/wiki/Lubricanthttp://en.wikipedia.org/wiki/Lubricanthttp://en.wikipedia.org/wiki/Lubricanthttp://en.wikipedia.org/wiki/Grease_(lubricant)http://en.wikipedia.org/wiki/Grease_(lubricant)http://en.wikipedia.org/wiki/Grease_(lubricant)http://en.wikipedia.org/wiki/Gear_oilhttp://en.wikipedia.org/wiki/Gear_oilhttp://en.wikipedia.org/wiki/Gear_oilhttp://en.wikipedia.org/wiki/Motor_oilhttp://en.wikipedia.org/wiki/Motor_oilhttp://en.wikipedia.org/wiki/Motor_oilhttp://en.wikipedia.org/wiki/Catalytic_converterhttp://en.wikipedia.org/wiki/Catalytic_converterhttp://en.wikipedia.org/wiki/Catalytic_converterhttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-2http://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-2http://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-2http://en.wikipedia.org/wiki/Camshafthttp://en.wikipedia.org/wiki/Camshafthttp://en.wikipedia.org/wiki/Camshafthttp://en.wikipedia.org/wiki/Spring_(device)http://en.wikipedia.org/wiki/Spring_(device)http://en.wikipedia.org/wiki/Spring_(device)http://en.wikipedia.org/wiki/Corrosion_inhibitorhttp://en.wikipedia.org/wiki/Corrosion_inhibitorhttp://en.wikipedia.org/wiki/Corrosion_inhibitorhttp://en.wikipedia.org/wiki/Corrosion_inhibitorhttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Corrosion_inhibitorhttp://en.wikipedia.org/wiki/Corrosion_inhibitorhttp://en.wikipedia.org/wiki/Spring_(device)http://en.wikipedia.org/wiki/Camshafthttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-2http://en.wikipedia.org/wiki/Catalytic_converterhttp://en.wikipedia.org/wiki/Motor_oilhttp://en.wikipedia.org/wiki/Gear_oilhttp://en.wikipedia.org/wiki/Grease_(lubricant)http://en.wikipedia.org/wiki/Lubricanthttp://en.wikipedia.org/wiki/AW_additivehttp://en.wikipedia.org/wiki/File:Zinc-diethyldithiophosphate-chain-from-xtal-3D-balls.pnghttp://en.wikipedia.org/wiki/Zinc_dithiophosphate#cite_note-1http://en.wikipedia.org/wiki/Zinc_acetatehttp://en.wikipedia.org/wiki/Zinc_acetate