US2613205A - Product of reaction of phosphorus sulfide, and hydrocarbon, with guanidine carbonate - Google Patents
Product of reaction of phosphorus sulfide, and hydrocarbon, with guanidine carbonate Download PDFInfo
- Publication number
- US2613205A US2613205A US89370A US8937049A US2613205A US 2613205 A US2613205 A US 2613205A US 89370 A US89370 A US 89370A US 8937049 A US8937049 A US 8937049A US 2613205 A US2613205 A US 2613205A
- Authority
- US
- United States
- Prior art keywords
- hydrocarbon
- oil
- product
- reaction
- oils
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims description 29
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 28
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 27
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 title description 14
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 title description 13
- 239000000047 product Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 28
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003921 oil Substances 0.000 description 39
- 235000019198 oils Nutrition 0.000 description 38
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 31
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 16
- 239000000654 additive Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 15
- 229910052698 phosphorus Inorganic materials 0.000 description 15
- 239000011574 phosphorus Substances 0.000 description 15
- 239000000314 lubricant Substances 0.000 description 14
- 239000010687 lubricating oil Substances 0.000 description 13
- 150000001298 alcohols Chemical class 0.000 description 12
- -1 isooctyl Chemical group 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 150000001336 alkenes Chemical class 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 150000002357 guanidines Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 150000007514 bases Chemical class 0.000 description 8
- 239000003599 detergent Substances 0.000 description 8
- 150000005673 monoalkenes Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000002199 base oil Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000010688 mineral lubricating oil Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229920002367 Polyisobutene Polymers 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 235000019271 petrolatum Nutrition 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229940042472 mineral oil Drugs 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 239000011347 resin Substances 0.000 description 2
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- 239000000344 soap Substances 0.000 description 2
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- 150000003568 thioethers Chemical class 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- 101150043532 CISH gene Proteins 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
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- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- FTOSZADXYFNRQP-UHFFFAOYSA-L calcium;2,2-dichlorooctadecanoate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCC(Cl)(Cl)C([O-])=O.CCCCCCCCCCCCCCCCC(Cl)(Cl)C([O-])=O FTOSZADXYFNRQP-UHFFFAOYSA-L 0.000 description 1
- DHJGVCITGOCTCA-UHFFFAOYSA-L calcium;hexadecyl phosphate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCOP([O-])([O-])=O DHJGVCITGOCTCA-UHFFFAOYSA-L 0.000 description 1
- LSCGCDXAEHGNMD-UHFFFAOYSA-N calcium;phenyl octadecanoate Chemical compound [Ca].CCCCCCCCCCCCCCCCCC(=O)OC1=CC=CC=C1 LSCGCDXAEHGNMD-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B47/00—Methods of operating engines involving adding non-fuel substances or anti-knock agents to combustion air, fuel, or fuel-air mixtures of engines
Definitions
- This invention relates to. mineraloil compositions and particularly to lubricants containing, a
- Thes detergents are particularly useful in lubricating oil compositions which are employedin internal combustion engines used in the operations of automobiles, aircraft and similar vehicles, including Diesel engines, to improve their operation by preventing or retardingcorrosion, piston ring sticking'cylinder wear, and carbonand varnish l formation.
- the free base guanidine and its derivatives may be used as well asjbasic acting saltsof suchbases, by whichis meantsalts of acids whose strength, measured on a 1:11 scale, is less than that of theacidic phosphorus sulfide-hydrocarbon product.
- Such reclaims. (or. 260-132) isooctyl, 2-ethylhexyl,. decyl, dodecyl, .tetradecyl, cetyl and stearylradicals.
- R, R and Rf may also represent cycloalkyl, ar ylalky1,'- aryl or alkylaryl illustrating the-'above' -describ d' types are the definedby the formula -s-Blisey i l fl ei ,s-Bten su e, j l ;qyclohexylguanidine b s c acting salts are, for example, the carbonates of guanidine and its derivatives. J Alternatively, the final products may be iormedby, double decomposition of a salt-of guanidineior' guanidine derivative, e.
- guanidine' hydrochloride or sulfate With a metal salt of 'th'e phosphorus sulfide-hydrocarbon reaction product.
- guanidine and its saltsar e preferred, substituted lguanidines may be used; Broadly, the guanidine type basic compounds' which maybe reacted in accordance witht he present invention may be in whichzR, landHR"; represent hydrogen or hydrocarbon groups. containing 1-:,to, 20 carbon atoms, e. ;g.,:: straight chain alkyl'groups, such as methyl, ethyljpropyl, butyl, alsoghigher: straight and branched chain alkyl' groups,: such. as octyl,
- substituting groupa' include the symmetrical trialkyl, trinap'hthenyl, and triarylalkyl guanidines.
- highly preferred' classes of substituted guanidines include the 'monoalkyl, mononaphthenyl; and monoaralkyl guanidines; unsymmetric'al' dialkyl, di-
- The-sulfide of phosphorus-which is employed in the-reaction with hydrocarbon material may be P283, P255, P483, P481 orotherphosphorus sulfide, and is preferably phosphorus pentasulfide, P255.
- the hydrocarbon material which may be re- "acted witha phosphorus sulfide in the'first step of the production. of additives-of the present invention. may-be parafilns, olefins .or olefin poly- .zmers', diolefins, acetylenes, aromatics or alkyl aromatics, cyclic .aliphatics, petroleum fractions, .such -as lubricating oil fractions, petrolatums, 'waxesmr'acked cyclestocks; or condensation prod- .ucts. of petroleum fractions, .solvent extracts of petroleum fractions; etc.
- wessentially paraffinic hydrocarbons such as brightstock residuums,-lubricating oil distillates, .petrolatums or. parafiixrwaxes may be employed. There may also be employed. products obtained ycondensing any ofthe foregoinghydrocarbons, usual-lythrough firstihalogenating the hydrocarbon; with aromatichydrocarbons in the presence of anhydrous inorganichalides, such as aluminum-z chloride, zinc' chloride, boronfluoride-"and vthe like.
- anhydrous inorganichalides such as aluminum-z chloride, zinc' chloride, boronfluoride-"and vthe like.
- Examples of monoolefins may be mentioned isobutylene, acrolein, decene, dodecene, cetene (C octadecene (C13), cerotene (Czs),:melene (Cat), olefinie extracts: f-romgasoline or gasoline itself, cracked cycle stocks and polymers thereof, resin oils-from crude oil, hydrocarboncoalresins, rcr'acked waxes, .dehydrohalogenated chlorinated waxes, and any mixed high molecular weight alkenes obtained: by cracking petroleum oils.
- a preferred class of olefins are-those having at least -20 .carbon atoms per molecule, of-whichfrom about 12. to abouti18 carbon'atoms, andpreferably at least carbon atoms, are in a long chain.
- Such olefins may be obtained by the dehydrogenation of parafiin waxes, by the dehydrolialogenation of long chain alkylf ha-lidea' 'by 'the synthesis of hydrocarbons from' ;CO"and"H'2';"by the dehydration of alcohols, etc.
- olefinicmateriafls are the monoolefin polymers, inwhich 'the'mqlecular weight ranges from 100 to 50,000; preferablyfrom and the-like.
- monoolefinic hydrocarbons such as ethylene, propylene, butylene, isobutylene, normal and isoamylenes, or hexenes, or by the copolymer-ization of any combination of the above monoolefinic materials.
- Diolefins which may be employed include well known materials such as butadiene, isoprene, chloroprene, eyclopentadiene, 2,3-dimethylbutadi'ene, 'pentadiene-LB, hexadiene-2,4, terpenes,
- Acetylene and substituted acetylenes may similarly be employed.
- Another class'of unsaturated hydrocarbon materials whichmaybe advantageously employed in the preparation of the additives of this invention are high molecular weight copolymers of low P molecular weight monoolefins and diolefins.
- copolymer is prepared by controlled copolymerization of a low molecular weight olefin and a nonaromatic hydrocarbon showing the general formula' Ci H21L-a'l7, in which a: is 2 ora multiple of 2; in thepresence of a catalyst of the Friedel- Crafts or peroxide type.
- the low molecular weight olefin is preferably an isoolefin or'a tertiary base olefin preferably one having less than 7- carbon atoms per molecule.
- olefins examples include isobutylene, Z-methylbutene-1,2-ethylbutene-l, secondary and tertiary base amylene, hexylenes, andzthe like.
- non- :aromatic hydrocarbons of the above formula which can .be used are the conjugated diolefins listed in the preceding paragraph, diolefins such asrlA-hexadiene, in which the double bond is not conjugated,.as well as the acetylenes.
- the .copolymerization is preferably carried out in the presence of aluminum chloride, boron fluoride, or benzoyl peroxide, and the copolymer is preferably one having a molecular weight of about 1,000 to 30,000.
- hydrocarbons which may be employed in a similar manner are aromatic hydrocarbons, such as benzene, naphthalene; anthracene', toluene, xylene, diphenyl, and the like, as well as aromatic hydrocarbons having alkyl .substituents, and aliphatic hydrocarbons having 'aryl substituents.
- Astill further class of hydrocarbons which maybe employed in the'reaction with sulfides ofphosphorus are condensation products of halogenated aliphatic hydrocarbons with an aromaticcompoun'd, produced by condensation. in the presence'of aluminum chloride or other Friedel-Crafts ty ecatalyst.
- the halogenated aliphatic hydrocarbon is preferably ahalogenated. long "chain paraffin. hydrocarbon having more-thanr8 carbon atoms, such as 'para'flin' wax, petrolatum, ozoceritewax, etc.
- High viscosity .parafiln .oils, particularly heavy residual: oil whichvhas been treated: with chemicals or extracted with'pro'pane or other solvents for :the removal .of asphalts may be employed.
- aromatic constituent may be naphthalene, fluorene, phenanthrene; anthracene, coal tar residues, and the like.
- Another i type of hydrocarbon material which maymbe similarly employed is a resin-like oil wlii'cli has a molecular-'wei'ght'of from about 1,000 toll-000 or highenobtained preferably'from a paraflinlc oil-which has been dewaxed and which is-"then treated with a liquefied normallygaseous hydrocarbon, e. 'propane, to precipitate a heavy propane-insoluble fraction.
- the latter is asubstantially-wax-free"and asphalt-free prod- 1 ctliaVing-a Saybol't 'viscosity'at 210 F. of about about 250 to about 10,000.
- 'rhete 101mm:rs'- may 112000 to f i llll conds or'more.
- e -m 'Ihe additive employed in the present inven- ;tion is the neutralized-reaction productobtained .by reacting one or more of the hereindescribed hydrocarbons with a phosphorus sulfide, preferablyphosphorus pentasulfide.
- Theiphosphorus sulfide-hydrocarbon reaction product may be readily obtained by reacting the phosphorus sulfide with. the hydrocarbon at a temperature of about 200-E. to about 600 F., and preferably from about 300 F.
- the eifect of adding compounds of the type described above to a lubricating oil will be to increase the detergent effect of the oil without sufficiently monoolefin polymers the preferred ratio is one molecular proportion of the sulfide of phosphorus to two, to five molecular proportions of polymer.
- reaction product may be further treated by blowin with steam, alcohol, ammonia, or anamine at an elevated temperature of about 200 F. to about 600 F. to improve the odor thereof.
- the neutralized phosphorus sulfide-hydrocarbon reaction product may then be prepared by reacting the above phosphorus sulfideehydrocarbon reaction product with the organic basic compound,such as guanidine or guanidine derivative of the type described above.
- This reaction may becarried out, preferablyin a non-oxidizing atmosphere, by contacting the phosphorus sulfide.- ihydrocarbonreaction product, eitheriassuch or d-issolved in asuitable solvent such as naphtha, with the basic compound, preferably at .a, temperature of about 100 F.
- additives-of the present invention are to be dissolvedin mineral oils, the hydrocarbons which are reacted with a sulfide of phosphorus and the guanyl compounds will be chosen with a View to provide a product which is solublein the oil base or which has such marginal solubility that it can be plasticized with a high molecular weight alcohol, ester, or other plastif 'cizers. 1
- silicone fluid was added to minimize foaming during this operation. After the guanidine carbonate was added the temperature was raised to 144 C. and then retained at this point for two hours, after which the solution was filtered.
- Example 2 A guanidine product in the form of a concentrate was prepared in the manner and from the materials described in Example 1, except thatin the step of neutralization with guanidine carbonate 88 grams of the concentrate of PzSa-ootadecene product wastreated with a mixture-of 5 I 7 grams; ofguanidine carbonate-and lgram of water; I
- Example 3 Reactions were. .carried out. as in Example '2, ,exceptthat amixture of 5..grams of'guanidine carbonate. and? grams of.water was ,used in the neutralization reaction.
- Ezvample 5 152.5 grams ofpolyethylene of molecular weight of about 400 was placed in a reaction flask-asin Example 4 and heated to300 F. 30 grams of phosphorus pentasulfide was added and the temperature raised to400 F. and held at this point for 6 /2 hours, after which the reaction mixture -Wasfiltered. 'The product was diluted with 150 "grams ofa solvent extracted Mid-Continent distillate oil of 150 seconds (Saybolt) viscosity at 100F. 200 grams of this solutionwastreated-at 1300" F.
- Example' 8 Ablend-containing z4r%.;by weight oj,the:5'0% concentrate of guanidine. product prepared asidescribedin Example .1 (2%.- ofxactive ingredient) 1 in a solvent extracted. paraflinic type: of mineral lubricating oil of SA'E:- 30zviscosity gradeanda :sample. of the unblende'di oil base were employed as the crankcase lubricant in 36 hourxiests' with a Chevroletengine operated. at 30' brake" horsepower, 3150 R. P. M. speed, 280 F. oil temperature and 200 F.
- the products ofthepresent invention may be employednot only in ordinary hydrocarbon lubricatingoils but also in the'ffheavy duty type of lubricating" oils which have been compounded with such detergent type additives as metal soaps, metal petroleum sulfonates, metalphenates, metal alcoholates, metal alkyl phenol sulfides, metalorgano phosphates, thiophosphates, phosphites and thiophosphites, metal salicyl-ates, metal xanthates and thioxanthates, metal thiocarbamates, aminesand amine derivatives, reaction products of metal phenates andsulfur, reaction products ofmetalphenates and phosphorus sulfides, metal phenolsulfonates and the like.
- detergent type additives as metal soaps, metal petroleum sulfonates, metalphenates, metal alcoholates, metal alkyl phenol sulfides, metalorgano phosphates, thiophosphates, phos
- the additives of the present invention maybe used in lubricating oils containing such otheraddition agents as barium tert.-octy1- phenol sulfide, calciumtert-amylphenol sulfide, nickel oleate, barium octadecylate, calcium phenyl stearate, zinc diisopropyl .salicylate, alu minum naphthenate, calcium cetyl phosphate, barium di-tert.-amylphenol sulfide, calcium petroleum sulfonate, zinc methyl cyclohexyl thiophosphate, calcium dichlorostearate, etc.
- Other types of additives such' as phenols and henol sulfides may be employed.
- the lubricating oil base stocks used in the compositions of this invention may be straight mineral lubricatingoils or idistillates derived from paraffinic, naphthenic, asphaltic, or mixed base crudes, or, if desired, various blended oils may be employed as well as residuals, particularly those from which asphaltic constituents have beencarefully removed.
- the oils maybe refined by conventional methods using acid, alkali and/or clay'or other agentssuch as aluminum chloride, or they may be extracted oils produced; for example, by solvent extraction with solvents of the type ofphenol, sulfur dioxide, furfural, dichlorodiethyl ether, nitrobenzene, crotonaldehyde, etc.
- Hydrogenated oils, White oils, or shale oilfl may be employed as well as synthetic oils, such as esters and polyethers as well as those prepared, for example, by the polymerization of olefins or by the reaction of oxides of carbon with hydrogen or by the hydrogenation of coal or its products.
- synthetic oils such as esters and polyethers as well as those prepared, for example, by the polymerization of olefins or by the reaction of oxides of carbon with hydrogen or by the hydrogenation of coal or its products.
- animal, vegetable or fish oils or their hpdrogenated or voltolized products may be employed in admixture with mineral oils.
- the base stock chosen should normally be that oil which without the new additive present gives the optimum per iormance in the service contemplated.
- the oil must possess the viscosity and volatility characteristics known to be required for the service contemplated.
- the oil must be a satisfactory solvent for the additive, although in some cases auxiliary solvent agents may be used.
- the lubricating oils may have been produced, may vary considerably in viscosity and other properties depending upon the particular use for which they are desired, but they usually range from about 40 to 150 seconds Saybolt viscosity at 210 F. For the lubricating of certain low and medium speed diesel engines the general practice has often been to use a lubricating oil base stock prepared from naphthenic or aromatic crudes and having a Saybolt viscosity at 210 F.
- oils of higherviscosity index are often preferred, for example, up
- agents may also be'usedsuch as dyes, pour depressors, Lhe'at thickened fatty oils, sulfurized fatty oils, organo metallic compounds, metallic or other soaps,
- cosity index im'provers such as esters, ketones, alcohols, .aldehydes, halogenated or vnitrated compounds, and the like .may also be employed.
- Assisting agents which are particularly desirable'as plasticizers anddefoamers are the higher alcohols having 8 or more carbon atoms and preferably V12 to-20 carbon atoms.
- the alcohols may be saturated straight and branched chain aliphatic.
- alcohols such as octyl alcohol (CsH1'iOH lauryl alcohol (C12H25OH) cetyl alcohol (CisHasOH), stearyl alcohol; sometimes referred to as octadecyl alcohol, (CisHs'zOH), heptadecyl alcohol (C1'1H35OH), and the like; the corresponding olefinic alcohols such as oleyl alcohol;
- cyclic alcohols such as naphthenicalcohols
- aryl substituted alkyl alcohols for instance,
- Products prepared synthetically by: chemical processes may also be used, such as alcohols pre-" pared by the oxidation of petroleum hydrocar bons, e. g. parafiin Wax, petrolatum, etc.
- the additives of the present invention may also be used in motor fuels, hydraulic fluids, torque converter fluids, cutting oils, flushing oils, turbine 011s or transformer oils, industrial oils, process oils and generally as anti-oxidants in mineral oil products. They may also be used in gear lubricants and greases. Since they are powerful surface active agents, they have practical use in dry cleaning fluids; mineral, spirit and aqueous paints, in flotation agents, and as dispersants for insecticides in aqueous and non-aqueous solu tions. They are also valuable anti-oxidants for natural and synthetic rubbers.
- R; R 'and R" each represent an alkyl group.
- composition according to claim 1 in which the. phosphorus sulfide-hydrocarbon reaction product is neutralized with guanidine carbonate.
- composition according to claim 1 in which the acidic reaction product is obtained by reactingphosphorus pentasulfide with a monoolefin.
- composition according to claim 6 in which the monoolefin is polyisobutylene.
- composition accordingto claim 8 in which thefguanidine carbonate is added in the form of a-mixture with water, such mixture containing 30-"70 by weight'of'guanidine carbonate.
- the processwhic h comprises reacting one molecular proportion of a phosphorus sulfide with about 1 to about 10'molecular proportionszof a hydrocarbon at-a temperature of about 200 to about 600"F. and neutralizing the acidic reaction productwith an organic basic reactingrcompound selectedfro'm the group consisting of: (1) free bases-0f the composition N-R Rz' 7/NR2 inwhich R, R and" R are each members of the group consisting of hydrogen and hydrocarbon radicals containing 1'-20 carbon atoms, and (2) basic reacting salts of the aforementioned free bases; 7
- Aoprocess which comprises reacting about one molecular proportion of phosphorus pentasulfide with two to'five' molecular proportions of polyisobutyleneare temperature of' about 300 to about 550? F., and then'neutralizingthe product'thus obtained with guanidine carbonate.
- a process accordingto claim 14 in which the guanidine carbonate is employed in the form of a mixture'withwater, such mixtur'e'containing 3'0-70% by weight of 'guanidine' carbonate.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Lubricants (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE495190D BE495190A (de) | 1949-04-23 | ||
NL75832D NL75832C (de) | 1949-04-23 | ||
US89370A US2613205A (en) | 1949-04-23 | 1949-04-23 | Product of reaction of phosphorus sulfide, and hydrocarbon, with guanidine carbonate |
GB4735/50A GB684168A (en) | 1949-04-23 | 1950-02-23 | Improvements in or relating to lubricating compositions |
FR1017810D FR1017810A (fr) | 1949-04-23 | 1950-03-21 | Produit lubrifiant |
CH301451D CH301451A (de) | 1949-04-23 | 1950-04-20 | Schmiermittel. |
DEST2129A DE863980C (de) | 1949-04-23 | 1950-09-14 | Mineralschmieroele |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89370A US2613205A (en) | 1949-04-23 | 1949-04-23 | Product of reaction of phosphorus sulfide, and hydrocarbon, with guanidine carbonate |
Publications (1)
Publication Number | Publication Date |
---|---|
US2613205A true US2613205A (en) | 1952-10-07 |
Family
ID=22217294
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US89370A Expired - Lifetime US2613205A (en) | 1949-04-23 | 1949-04-23 | Product of reaction of phosphorus sulfide, and hydrocarbon, with guanidine carbonate |
Country Status (7)
Country | Link |
---|---|
US (1) | US2613205A (de) |
BE (1) | BE495190A (de) |
CH (1) | CH301451A (de) |
DE (1) | DE863980C (de) |
FR (1) | FR1017810A (de) |
GB (1) | GB684168A (de) |
NL (1) | NL75832C (de) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2735817A (en) * | 1956-02-21 | Stabilized lubricating oil additives | ||
US2738340A (en) * | 1952-05-20 | 1956-03-13 | Sinclair Refining Co | Urea-pinene-sulfide reaction product |
US2742429A (en) * | 1952-03-11 | 1956-04-17 | Sinclair Refining Co | Lubricating oil compositions |
US2765277A (en) * | 1951-11-21 | 1956-10-02 | Exxon Research Engineering Co | Lubricating oil additives |
US2812319A (en) * | 1951-11-21 | 1957-11-05 | Exxon Research Engineering Co | Lubricating oil additives |
US2929828A (en) * | 1955-09-28 | 1960-03-22 | Exxon Research Engineering Co | Lubricant additives |
US3003964A (en) * | 1954-03-01 | 1961-10-10 | Exxon Research Engineering Co | Radiochemical production of phosphosulfurized hydrocarbons |
DE1157330B (de) * | 1960-12-23 | 1963-11-14 | Shell Int Research | Kohlenwasserstoffschmieroel |
US4295982A (en) * | 1980-05-12 | 1981-10-20 | Mobil Oil Corporation | Sulfurized aminoguanidine reaction product and lubricant compositions containing same |
US20030168224A1 (en) * | 2000-05-22 | 2003-09-11 | Eva Freudenthaler | Novel phosphorous-nitrogen compounds used as fireproofing agents in theroplastic molding materials and the production thereof |
US20030176714A1 (en) * | 2001-09-25 | 2003-09-18 | Curphey Thomas J. | Compositions and methods for thionation during chemical synthesis reactions |
CN108570331A (zh) * | 2017-03-08 | 2018-09-25 | 上海梅山钢铁股份有限公司 | 一种配用废橡胶的焦炭及炼焦方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US2400786A (en) * | 1946-05-21 | Method of preventing silverware | ||
US2401733A (en) * | 1945-01-26 | 1946-06-11 | Wyandotte Chemicals Corp | Corrosion inhibitor |
US2403474A (en) * | 1944-10-10 | 1946-07-09 | Standard Oil Co | Additive for lubricants |
US2449933A (en) * | 1943-11-27 | 1948-09-21 | Socony Vacuum Oil Co Inc | Method of making phosphorus-and sulfur-containing organic reaction products |
US2449934A (en) * | 1945-08-08 | 1948-09-21 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2506572A (en) * | 1946-04-19 | 1950-05-09 | Standard Oil Co | Lubricant composition |
-
0
- BE BE495190D patent/BE495190A/xx unknown
- NL NL75832D patent/NL75832C/xx active
-
1949
- 1949-04-23 US US89370A patent/US2613205A/en not_active Expired - Lifetime
-
1950
- 1950-02-23 GB GB4735/50A patent/GB684168A/en not_active Expired
- 1950-03-21 FR FR1017810D patent/FR1017810A/fr not_active Expired
- 1950-04-20 CH CH301451D patent/CH301451A/de unknown
- 1950-09-14 DE DEST2129A patent/DE863980C/de not_active Expired
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2400786A (en) * | 1946-05-21 | Method of preventing silverware | ||
US2449933A (en) * | 1943-11-27 | 1948-09-21 | Socony Vacuum Oil Co Inc | Method of making phosphorus-and sulfur-containing organic reaction products |
US2403474A (en) * | 1944-10-10 | 1946-07-09 | Standard Oil Co | Additive for lubricants |
US2401733A (en) * | 1945-01-26 | 1946-06-11 | Wyandotte Chemicals Corp | Corrosion inhibitor |
US2449934A (en) * | 1945-08-08 | 1948-09-21 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2506572A (en) * | 1946-04-19 | 1950-05-09 | Standard Oil Co | Lubricant composition |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2735817A (en) * | 1956-02-21 | Stabilized lubricating oil additives | ||
US2765277A (en) * | 1951-11-21 | 1956-10-02 | Exxon Research Engineering Co | Lubricating oil additives |
US2812319A (en) * | 1951-11-21 | 1957-11-05 | Exxon Research Engineering Co | Lubricating oil additives |
US2742429A (en) * | 1952-03-11 | 1956-04-17 | Sinclair Refining Co | Lubricating oil compositions |
US2738340A (en) * | 1952-05-20 | 1956-03-13 | Sinclair Refining Co | Urea-pinene-sulfide reaction product |
US3003964A (en) * | 1954-03-01 | 1961-10-10 | Exxon Research Engineering Co | Radiochemical production of phosphosulfurized hydrocarbons |
US2929828A (en) * | 1955-09-28 | 1960-03-22 | Exxon Research Engineering Co | Lubricant additives |
DE1157330B (de) * | 1960-12-23 | 1963-11-14 | Shell Int Research | Kohlenwasserstoffschmieroel |
US4295982A (en) * | 1980-05-12 | 1981-10-20 | Mobil Oil Corporation | Sulfurized aminoguanidine reaction product and lubricant compositions containing same |
US20030168224A1 (en) * | 2000-05-22 | 2003-09-11 | Eva Freudenthaler | Novel phosphorous-nitrogen compounds used as fireproofing agents in theroplastic molding materials and the production thereof |
US20030176714A1 (en) * | 2001-09-25 | 2003-09-18 | Curphey Thomas J. | Compositions and methods for thionation during chemical synthesis reactions |
US7012148B2 (en) * | 2001-09-25 | 2006-03-14 | Trustees Of Dartmouth College | Compositions and methods for thionation during chemical synthesis reactions |
CN108570331A (zh) * | 2017-03-08 | 2018-09-25 | 上海梅山钢铁股份有限公司 | 一种配用废橡胶的焦炭及炼焦方法 |
Also Published As
Publication number | Publication date |
---|---|
DE863980C (de) | 1953-01-22 |
GB684168A (en) | 1952-12-10 |
BE495190A (de) | |
CH301451A (de) | 1954-09-15 |
FR1017810A (fr) | 1952-12-19 |
NL75832C (de) |
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