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zinc dithiophosphate wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 applications toggle applications subsection 1 1 tribofilm formation mechanism 2 synthesis and structure 3 references toggle the table of contents zinc dithiophosphate 5 languages čeština français italiano 日本語 nederlands edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia lubricant additive structure of an ligand l adduct of a typical zinc bis dithiophosphate complex such zinc dithiophosphate complexes are usually pentacoordinate 1 zinc dialkyldithiophosphates often referred to as zddp are a family of coordination compounds classified as members of transition metal dithiophosphate complexes these compounds were introduced in the 1940s as oil additives they are uncharged compounds not salts they are soluble in nonpolar solvents and the longer chain derivatives easily dissolve in mineral and synthetic oils used as lubricants they come under cas number 68649 42 3 in aftermarket oil additives the percentage of zddp ranges approximately between 2 and 15 2 zinc dithiophosphates have many names including zddp zndtp and zdp applications edit selected zinc dithiophosphates r group compound registry number melting point c ch 3 zn s 2 p ome 2 2 25502 69 6 c 2 h 5 zn s 2 p oet 2 2 7268 60 2 ch ch 3 2 zn s 2 p oc i pr 2 2 2929 95 5 131 c 4 h 9 zn s 2 p obu 2 2 6990 43 8 36 8 ch 2 ch ch 3 2 zn s 2 p och 2 chme 2 2 2 4563 55 7 107 the main application of zddps are as anti wear additives in lubricants including greases hydraulic oils and motor oils zddps also act as corrosion inhibitors and antioxidants concentrations in lubricants range from 600 ppm for modern energy conserving low viscosity oils to 3000 ppm in some racing oils 3 it has been reported that zinc and phosphorus emissions may damage catalytic converters and standard formulations of lubricating oils for gasoline engines now have reduced amounts of the additive due to the api limiting the concentration of this additive in new api sm and sn oils however this affects only 20 and 30 grade ilsac oils grades 40 and higher have no regulation regarding the concentration of zddp except for diesel oils meeting the api cj 4 specification which have had the level of zddp reduced slightly although most diesel heavy duty engine oils still have a higher concentration of this additive 4 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 main bearings and piston rings and pins roller camshafts followers are more commonly used to reduce camshaft lobe friction in modern engines 5 there are additives such as stp oil treatment and some racing oils such as purol penngrade 1 and valvoline vr 1 kixx hydraulic oil which are available in the retail market with the necessary amount of zddp for engines using increased valve spring pressures tribofilm formation mechanism edit various mechanisms have been proposed for how zddp forms protective tribofilms on solid surfaces 6 in situ atomic force microscopy afm experiments show that the growth of zddp tribofilms increases exponentially with both the applied pressure and temperature consistent with a stress promoted thermal activation reaction rate model 7 subsequently experiments with negligible solid solid contact demonstrated that film formation rate depends on the applied shear stress 8 synthesis and structure edit with the formula zn s 2 p or 2 2 zinc dithiophosphate features diverse r groups typically r is a branched or linear alkyl between 1 14 carbons in length examples include 2 butyl pentyl hexyl 1 3 dimethylbutyl heptyl octyl isooctyl 2 ethylhexyl 6 methylheptyl 1 methylpropyl dodecylphenyl and others a list of examples with their cas numbers is here zinc dithiophosphate are often produced in two steps first phosphorus pentasulfide is heated with suitable alcohols roh to 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 dithiophosphoric acid is then neutralized e g with ammonia or by adding zinc oxide 9 10 p 2 s 5 4 roh 2 ro 2 ps 2 h h 2 s 2 ro 2 ps 2 h zno zn s 2 p or 2 2 h 2 o monomeric zn s 2 p or 2 2 appear not to exist instead these complexes exist as dimers in solution or polymers in the solid form 9 the dissociation constant for the dimers at room temperature is 10 2 m 11 zn s 2 p or 2 2 2 2 zn s 2 p or 2 2 the dimers dissociate in the donor solvents ethanol or upon treatment with lewis bases forming adducts zn s 2 p or 2 2 2 2 l 2 lzn s 2 p or 2 2 the polymers zn s 2 p or 2 2 n n 1 have also been characterized for example zinc diethyldithiophosphate zn s 2 p oet 2 2 crystallizes as a polymers consisting of linear chains 12 reaction of zn s 2 p or 2 2 with additional zinc oxide gives rise to the oxygen centered cluster zn 4 o s 2 p or 2 6 which adopts the structure seen for basic zinc acetate 9 ball and stick model of part of a chain of zinc diethyldithiophosphate color code yellow s references edit ellis carol a ng seik weng tiekink edward r t 2007 μ 1 4 diazabicyclo 2 2 2 octane κ 2 n n bis bis o o diisopropyl dithiophosphato κ 2 s s zinc ii acta crystallographica section e structure reports online 63 m108 m110 doi 10 1107 s1600536806052007 allyson m barnes keith d bartle and vincent r a thibo a review of zinc dialkyldithiophosphates zddps characterisation and role in the lubricating oil tribology international 2001 pp 389 395 doi 10 1016 s0301 679x 01 00028 7 zinc dialkyl dithiophosphates molecule of the week archive zddp engine oil the zinc factor mustang monthly archived from the original on 2009 09 12 retrieved 2009 09 19 mcgean terry 1 march 2004 roller camshafts roll with it www hotrod com retrieved 26 january 2016 spikes h 2004 10 01 the history and mechanisms of zddp tribology letters 17 3 469 489 doi 10 1023 b tril 0000044495 26882 b5 issn 1023 8883 s2cid 7163944 gosvami n n bares j a mangolini f konicek a r yablon d g carpick r w 2015 04 03 mechanisms of antiwear tribofilm growth revealed in situ by single asperity sliding contacts pdf science 348 6230 102 106 bibcode 2015sci 348 102g doi 10 1126 science 1258788 issn 0036 8075 pmid 25765069 zhang jie spikes hugh 2016 08 01 on the mechanism of zddp antiwear film formation tribology letters 63 2 24 doi 10 1007 s11249 016 0706 7 hdl 10044 1 33668 issn 1023 8883 1 2 3 d johnson and j hils 2013 phosphate esters thiophosphate esters and metal thiophosphates as lubricant additives lubricants 1 4 132 148 doi 10 3390 lubricants1040132 randolph a mcdonald 2003 zinc dithiophosphates google books excerpt in leslie r rudnick ed lubricant additives chemistry and applications crc press isbn 9780824747404 harrison philip g kikabhai thakor 1987 proton and phosphorus 31 nuclear magnetic resonance study of zinc ii o o dialkyl dithiophosphates in solution j chem soc dalton trans 4 807 814 doi 10 1039 dt9870000807 t ito t igarashi h hagihara 1969 the crystal structure of metal diethyldithiophosphates i zinc diethyldithiophosphate pdf acta crystallogr b 25 11 2303 2309 bibcode 1969accrb 25 2303i doi 10 1107 s0567740869005619 v t e zinc compounds zinc i organozinc i compounds zn 2 c 5 ch 3 5 2 zinc ii zn acac 2 zn 3 sb 2 zn 3 as 2 zn n 3 2 znbr 2 znco 3 zn cn 2 zncl 2 zn clo 3 2 zncro 4 znf 2 znh 2 zni 2 znmoo 4 zn 3 n 2 zn no 3 2 zno zno 2 zn 2 p 2 o 7 zn 3 p 2 znp 2 zn 3 po 4 2 zn clo 4 2 zn oh 2 zns znso 4 znse znseo 4 znte znwo 4 organozinc ii compounds zn ch 3 2 zn c 2 h 5 2 zn ch 3 coo 2 zn ch ch 3 2 2 zn c ch 3 3 2 zn c 6 h 5 2 zn c 3 h 5 o 3 2 znich 2 i c 24 h 46 zno 4 v t e sulfur compounds sulfides and disulfides al 2 s 3 as 2 s 2 as 2 s 3 as 2 s 5 as 4 s 4 au 2 s au 2 s 3 b 2 s 3 bas bes bi 2 s 3 cs 2 c 3 s 2 c 6 s 6 cas cds ces cos cr 2 s 3 csse cste cufes 2 cus d 2 s dy 2 s 3 er 2 s 3 eus fes 2 gas h 2 s hfs 2 hgs in 2 s 3 k 2 s las li 2 s mgs mos 2 mos 3 nahs na 2 s nh 4 hs nis p 4 s x pbs pbs 2 pscl 3 psi 3 pts res 2 re 2 s 7 sis srs tls vs ses 2 s 2 u ws 2 ws 3 sb 2 s 3 sb 2 s 5 sb 4 s 3 o 3 sm 2 s 3 y 2 s 3 zrs 2 la 2 o 2 s gd 2 o 2 s sulfur halides s 2 br 2 sbr 2 s 2 cl 2 scl 2 scl 4 s 2 f 2 sf 2 sf 4 s 2 f 10 sf 6 s 2 i 2 sulfur oxides and oxyhalides brso 3 f s 2 o 5 cl 2 f 2 s 5 o 2 fclo 5 s 2 f 2 os 3 iso 3 f f 2 o 6 s 2 so 2 so 3 sobr 2 socl 2 sof 2 sof 4 so 2 f 2 so 2 brf so 2 clf so 2 cl 2 h 2 s 3 o 6 i 3 so 3 f s 3 o 8 cl 2 s 3 o 8 f 2 h 2 so 3 h 2 so 4 h 2 s 2 o 7 h 2 so 5 sulfites nh 4 2 so 3 li 2 so 3 na 2 so 3 k 2 so 3 mgso 3 caso 3 baso 3 cdso 3 ag 2 so 3 sulfates ag 2 so 4 caso 4 cuso 4 cs 2 so 4 er 2 so 4 3 eu 2 so 4 3 hgso 4 k 2 so 4 kal so 4 2 naal so 4 2 raso 4 snso 4 srso 4 ti so 4 2 tm 2 so 4 3 yb 2 so 4 3 zr so 4 2 sulfur nitrides sn s 2 n 2 s 4 n 4 thiocyanates hscn kscn co scn 2 polythionates nas 3 o 6 nas 4 o 6 nas 5 o 6 nas 6 o 6 nas 7 o 6 organic compounds thiol ch 3 sh ccl 3 sh ch 3 ch 2 sh cysteine coenzyme b coenzyme m glutathione organic sulfide ch 3 sch 3 methionine heterocycles c 2 h 4 s c 4 h 4 s thiamine biotin thia crown ether sulfonium s adenosyl methionine s methylmethionine dimethylsulfoniopropionate disulfide c 32 h 66 s 2 heterocycles lipoic acid trisulfide ch 3 sssch 3 thiosulfinate allicin sulfinic acid hypotaurine sulfone cfno 3 s c 2 n 2 o 4 s sulfonate coenzyme m taurine 3 phosphoadenosine 5 phosphosulfate organic thiocyanates c 2 h 3 sn retrieved from https en wikipedia org w index php title zinc_dithiophosphate oldid 1312881309 categories zinc compounds phosphorothioates lubricants corrosion inhibitors hidden categories articles with short description short description is different from wikidata this page was last edited on 23 september 2025 at 03 56 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of 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