US2502408A - Lubricating composition - Google Patents
Lubricating composition Download PDFInfo
- Publication number
- US2502408A US2502408A US782044A US78204447A US2502408A US 2502408 A US2502408 A US 2502408A US 782044 A US782044 A US 782044A US 78204447 A US78204447 A US 78204447A US 2502408 A US2502408 A US 2502408A
- Authority
- US
- United States
- Prior art keywords
- reaction product
- ratio
- sulfur
- carbon atoms
- temperature ranging
- 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
- 239000000203 mixture Substances 0.000 title claims description 29
- 230000001050 lubricating effect Effects 0.000 title claims description 15
- 239000007795 chemical reaction product Substances 0.000 claims description 62
- 150000003997 cyclic ketones Chemical class 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 58
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 239000000654 additive Substances 0.000 description 29
- -1 phosphorus compound Chemical class 0.000 description 26
- 239000000314 lubricant Substances 0.000 description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 23
- 229910052717 sulfur Inorganic materials 0.000 description 22
- 239000011593 sulfur Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000011574 phosphorus Substances 0.000 description 16
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 14
- 229910052698 phosphorus Inorganic materials 0.000 description 14
- 150000002576 ketones Chemical class 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 10
- 238000005260 corrosion Methods 0.000 description 9
- 239000003599 detergent Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 235000010446 mineral oil Nutrition 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000007797 corrosion Effects 0.000 description 8
- 230000006866 deterioration Effects 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000010685 fatty oil Substances 0.000 description 5
- 239000010688 mineral lubricating oil Substances 0.000 description 5
- 230000009972 noncorrosive effect Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000010802 sludge Substances 0.000 description 5
- 238000005987 sulfurization reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 235000011941 Tilia x europaea Nutrition 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000004571 lime Substances 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 239000003575 carbonaceous material Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- VSAISIQCTGDGPU-UHFFFAOYSA-N phosphorus trioxide Inorganic materials O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 3
- 238000006748 scratching Methods 0.000 description 3
- 230000002393 scratching effect Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- GCRTVIUGJCJVDD-UHFFFAOYSA-N Tetrahydrocarvone Chemical class CC(C)C1CCC(C)C(=O)C1 GCRTVIUGJCJVDD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000012188 paraffin wax Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Chemical class CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 1
- NZGWDASTMWDZIW-MRVPVSSYSA-N (+)-pulegone Chemical class C[C@@H]1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-MRVPVSSYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- WALBTDFSFTVXII-UHFFFAOYSA-N 2,3,4,5,6-pentamethylphenol Chemical compound CC1=C(C)C(C)=C(O)C(C)=C1C WALBTDFSFTVXII-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 1
- DRRDTKUTHYHEKE-UHFFFAOYSA-N 2,4-dimethyl-6-octylphenol Chemical compound CCCCCCCCC1=CC(C)=CC(C)=C1O DRRDTKUTHYHEKE-UHFFFAOYSA-N 0.000 description 1
- WCWCBLDWXBFHHT-UHFFFAOYSA-N 2-amino-3-benzylphenol Chemical class NC1=C(O)C=CC=C1CC1=CC=CC=C1 WCWCBLDWXBFHHT-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- AHZRNZSJQJDAQP-UHFFFAOYSA-N 2-cyanooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C#N)C(O)=O AHZRNZSJQJDAQP-UHFFFAOYSA-N 0.000 description 1
- PGFRHDVDFUQDDV-UHFFFAOYSA-N 4,4-dibutylcyclohexan-1-one Chemical group CCCCC1(CCCC)CCC(=O)CC1 PGFRHDVDFUQDDV-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical class O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical class CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- NZGWDASTMWDZIW-UHFFFAOYSA-N Pulegone Chemical class CC1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Chemical class O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
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- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical group [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000003998 acyclic ketones Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- USMNOWBWPHYOEA-UHFFFAOYSA-N alpha-thujone Chemical class CC1C(=O)CC2(C(C)C)C1C2 USMNOWBWPHYOEA-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
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- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 229930007459 p-menth-8-en-3-one Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
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- 150000003470 sulfuric acid monoesters Chemical class 0.000 description 1
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- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- This invention relates to new and novel products which have properties of greatly improving and stabilizing lubricants. More particularly, this invention pertains to oleaginous materials, especially lubricants, such as mineral lubricating oils, synthetic lubricants of hydrocarbon and non-hydrocarbon origin, and the like, containing a multi-functional additive having detergent and anti-ringsticking properties, which additive also acts as an inhibitor of oxidation and corrosion.
- lubricants such as mineral lubricating oils, synthetic lubricants of hydrocarbon and non-hydrocarbon origin, and the like
- a multi-functional additive having detergent and anti-ringsticking properties, which additive also acts as an inhibitor of oxidation and corrosion.
- additives which have the effect or property of inhibiting deterioration of lubricants and impart to them certain beneficial properties.
- additives have been specifically designed which have the property of inhibiting corrosion of alloyed bearings such as copper-lead, cadmium-silver and the like, developed for automotive, Diesel and aircraft engines. Acidic oxidation or decomposition components formedin lubricants during use can readily attack these bearings, but are inhibited or prevented from doing this by the formation of a corrosion protective film formed with the aid of the additive on the bearing surface.
- Additives have also been developed which possess the property of modifying the carbonaceous materials formed by deterioration of lubricants on piston rods, rings and valves and other metal parts in internal combustion engines, automotive and truck engines, aviation engines, high speed Diesel engines, and the like. These additives serve a very important function because by modifying this carbonaceous material so that it can be removed easily, the tendency of engine parts to become stuck is inhibited; ringsticking, piston scufiing and scratching and wearing away of other parts and material reduction of engine efliciency is thereby prevented.
- additives have been developed which act as detergents in order to assist in the removal of soot, sludge, varnish, and/or lacquer formed from deterioration of the oil at high operating temperatures. Detergents, due to their cleansing action, prevent the build-up of these deleterious materials and assist in removing those formed.
- Anti-wear additives have the property of reducing friction of movable metal parts of the same or different metals. Due to the function exerted or property imparted by such additives on lubricants, wear caused by direct frictional contact of metals can be greatly reduced. Also additives have been developed for withstanding extreme pressures, dispersion of impurities, solubilizing of certain other additives, etc.
- a multi functional material so as to inhibit oxidation and corrosion and prevent the formation of sludge, varnish and lacquer in said lubricants even under adverse operating conditions.
- Still another object of this invention is to use in lubricating compositions a material which prevents ringsticking as well as the sticking of other engine parts due to deterioration of the lubricant. Also it is an object of this'invention to use in lubricating compositions a material which inhibits wear, scuifing, scratching and other damage to engine parts. Another object of this invention to provide novel compounds which possess multi-functional improving and enhancing properties when added to lubricants.
- oleaginous materials e. g. various lubricating bases
- a minor amount of a reaction product obtained by treating a saturated or unsaturated cyclic ketone fraction having at least 12 and preferably more than 18 carbon atoms in ,the molecule (which ketone fractions may be obtained from isophorone bottoms during its synthesis fIOm acetone by condensation as well as from other sources) with a phosphorus compound which is free from sulfur, and thereafter subjecting said phosphorized cyclic ketone to a sulfurization treatment at an elevated temperature.
- This reaction product may also be further treated with any, suitable metal such as alkali metals, alkaline earth metals, heavy metals, nitrogen containing organic bases and the like.
- suitable metal such as alkali metals, alkaline earth metals, heavy metals, nitrogen containing organic bases and the like.
- the above reaction product may be treated with such a compound as a hydroxide, carbonate or oxide'of Na, Li, K, Ca, Ba, Sr, Mg, Al, Zn, Cu, Cr, Cd, Fe, Mn, Ni, Sn, etc., or basic reagents such as ammonia, alkyl of aryl substituted ammonia, such as amines, quaternary ammonium compounds and the like.
- the preferred ketones used to obtain the oil additive of this invention are the unsaturated cyclic ketones normally obtained from isophorone bottoms produced by condensation of acetone under elevated temperature and pressure.
- the isophorone bottoms thus produced may be fractionated into various cuts each of which may be used to form the reaction product of this invention.
- specific isophorone fractions which may be used are topped crude isophorone bottoms, topped crude hydrolyzed isophorone bottoms, and the like.
- topped crude isophorone bottoms and topped crude hydrolyzed isophorone bottoms, and similar terms, which will be hereinafter used and fully described are generic and are used to identify various unsaturated cyclic ketone fractions of relatively high molecular weight obtained from acetone condensation. Unsaturated cyclic ketone fractions useable in reactions of the kind under consideration may be obtained by condensing acetone in 30% to 60% caustic so- It is still.
- the product remaining in the still is purified by filtration, solvent treatment or the like, and comprises crude unsaturated cyclic ketones of high lution at a temperature ranging betweenmolecular weight, referred to herein as crude isophorone bottoms.
- isophorone bottoms as referred to herein is thus a complex mixture of high molecular weight unsaturated cyclic ketones containing at least 12 and preferably more than 18 carbon atoms in the molecule.
- Isophorone bottoms produced by condensation of acetone under conditions referred to above included within itsscope any and all unsaturated cyclic ketones containing at least 12 and preferably more than 18 carbon atoms and having generally the chemical structural configcrude isophorone bottoms are topped crude isophorone bottoms which contain at least 15 carbon atoms in the molecule and which are obtained after removal of distillate from crude isophorone bottoms to a still head temperature of 284 F. at 10 mm. Hg pressure.
- Crude isophorone bottoms can be subected to hydrolysis with dilute sodium hydroxide, and the acetone and isophorone formed removed by distillation. The bottoms can then be filtered and purified and comprise essentially unsaturated cyclic ketones containing at least 12 carbon atoms in the molecule; these are referred to herein as crude hydrolyzed isophorone bottoms. This material can be subjected to distillation to split it into two fractions. The distilled hydrolyzed isophorone fraction has a boiling point of about 140 C. at 10 mm. Hg pressure and consists of a mixture of unsaturated cyclic ketones containing between 15 and 18 carbon atoms in the molecule.
- the residue is referred to as topped crude hydrolyzed isophorone bottoms, which is similar to topped crude isophorone bottoms.
- This residue comprises essentially unsaturated cyclic ketones of at least 15 carbon atoms in the molecule; Crude isophorone bottoms can be also subjected to condensation over solid sodium hydroxide to yield two types of resinous materials.
- the first resinous fraction or soft resin has a viscosity at 210 F. of about 25-26 centistokes and an average molecular weight of 320 to 350.
- the heavier fraction or medium resin has a viscosity at 210 F. of about to centistokes and an average molecular weight of 370 to 390.
- All of the various unsaturated cyclic ketone fractions obtained in the manner fully described above can be used for reacting with phosphorus sulfide to form a multi-functional lubricating additive.
- Other cyclic ketones having at least 12 carbon atoms are obtained by hydrogenating the above unsaturated cyclic ketones to obtain saturated cyclic ketones having at least 12 carbon atoms, alkyl cyclohexanone, i. e. dibutyl cyclohexanone, alkyl substituted carvomenthone, menthone, pulegone,
- carvone, camphor, and the like having at least 12 carbon atoms.
- the phosphorizlng agent which can be used to form the initial reaction product of this invention may be any sulfur-free phosphorus containing compound capable of reacting and introducing phosphorus into acyclic ketone.
- Specific phosphorizing agents may include elemental phosphorus, the phosphorus halides, oxyhalides, compounds of the oxygen family, e. g. P205, P203, etc.; metallic phosphides such as sodium or tin phosphides; phosphoric acid anhydride, said anhydride generally being accelerated by addition of acetyl chloride; phosphoric acid and the like.
- the type of pho-sphorizing agent used, the ratio of the two reactants, the temperature, time and condition under which the reaction is to be carried out, as well as the manner in which the reaction product is recovered, may be varied within the limits described herein provided the phosphorus-chemically combines with the cyclic ketone of this invention.
- Phosphorization may be carried out in an inert solvent and/or under inert conditions, and depending upon the nature of the two reacting materials the temperature may vary between about 170 F. and about 350 F., although the range of 200F. to 250 F. is preferred.
- the preferred phosphorizing agents are elemental phosphorus and phosphorus pentoxide, and the preferred ketone fractions which are reacted with said phosphorizing agents are topped crude isophorone bottoms which are residues remaining after removal of distillate from crude isophorone bottoms to a still head temperature of 284 F. at mm. Hg pressure, and comprising unsaturated cyclic ketones containing at least carbon atoms in the molecule.
- Another preferred fraction is a topped crude hydrolyzed isophorone bottoms obtained from crude hydrolyzed isophorone bottoms, similar to the topped crude isophorone bottoms.
- the term topped used throughout has the same meaning as in the petroleum art, namely, a distillation or fractionation step, whereby certain materials are removed as an overhead fraction.
- the mol ratio of the phosphorizing agent to ketone may vary from about 1:2 to about 1:4, and even to about 1:8, of the phosphorizing agent to ketone depending upon the reactivity of the reactants. Also in carrying out the reaction it is advisable to initially control the reaction so that the temperature does not rise too rapidly. Generally it is preferred to keep the reaction at below 176 F. until all the reactants have been added and the reaction proceeds smoothly. Thereafter the temperature can be raised rapidly to the desired or optimum temperature.
- reaction should be carried out in a substantially inert atmosphere, and the two materials can be reacted per se or disposed in a suitable inert or non-reactive diluent and then reacted under conditions described above.
- This reaction product may be purified before subjecting it to the next reaction step or the crude product may be subjected to a sulfurization process which is the next step and thereafter recovered and purified.
- the sulfurization of the phosphorized reaction product of the invention is carried out at an elevated temperature and the sulfurizing agent may be selected from the class consisting of elemental sulfur, flowers of sulfur, sulfur halides,
- alkali polysiilflde ammonium hydrogen sulfidehydrogen sulfide, sulfur dioxide and the like.
- the mol ratio of the sulfurizing agent such as sulfur and phosphorized cyclic ketone may be varied over wide limits, it is preferable to keep said reactants in a moi ratio of from about 0.5:1 to about 1:1.
- the reaction should be carried out in substantially inert atmosphere .at a temperature of between about 250 F. and about 450 F., and preferably between 300 F. and 350 F.
- the sulfurization of the initial reaction product namely a phosphorized ketone, may be carried cut progressively in the same-vessel, by simply adding the required amount of sulfur or the like and adjusting the reaction condition. Iithe initial reaction product has been purified first, it may be redispersed in a suitable diluent and then reacted with sulfur or the like in the manner described.
- the final reaction product of this invention may be neutralized by treatment with-a suitable basic compound such as hydroxide, oxide or carbonate of an alkaline earth metal, alkali metal or other suitable basic reagent such as ammonia, alkyl or aryl amines, quaternary ammonium compounds or heavy metals such as Al, Cr, Fe, Sn and the like.
- suitable basic compound such as hydroxide, oxide or carbonate of an alkaline earth metal, alkali metal or other suitable basic reagent
- ammonia alkyl or aryl amines, quaternary ammonium compounds or heavy metals such as Al, Cr, Fe, Sn and the like.
- Preferred reagents are Ca, Ba, Mg, Na, K, Al and Zn.
- the entire reaction procedure of this invention is relatively simple and requires no elaborate or special equipment, undueprecaution or skill.
- the obtainment of the initial reaction product simply requires stirring an unsaturated cyclic ketone with phosphorus or phosphorus pentoxide, in an inert atmosphere, such as nitrogen or carbon dioxide.
- the temperature of the reaction should be increased gradually up to about F.
- reaction product may be extracted with a non-aromatic solvent and the extracting medium removed by distillation or the like.
- the phosphorized ketone is then dispersed in a suitable solvent and a calculated amount of sulfur added under inert conditions and the mixture reacted for 2 to 8 hours at a temperature above about 250 F. to 300 F. or higher.
- the sludge like material formed during the reaction is removed and the product purified by solvent extraction, blowing and washing.
- salts may be formed by agitating the reaction product in a suitable diluent such as mineral oil with a calculated amount of lime or any other desired neutralizing 7 agent at a temperature of above about 250 F. for about 2 hours.
- a stream of inert gas is usually blown through the mixture to remove any entrained moisture or other contaminates.
- the neutralized reaction product can be recovered from the oil by filtration and may be refiltered to remove excess lime, and other impurities.
- EXAMPLE I Part A A mixture of approximately, one mol of cyclic unsaturated ketones containing at least 18 carbon atoms in the molecule, obtained by topping bottoms from crude isophorone bottoms at a kettle temperature of between about 284 F. and mm. Hg pressure, and one mol of phosphorus pentoxide were stirred and heated in an inert atmosphere of carbon dioxide for about five hours at around 200 F. The mixture was initially maintained at about 140 F. and then heated to about 300 F. At the end of the reaction period, the reaction product was extracted with a non-aromatic hydrocarbon and the solvent removed by evaporation at steam temperature in a current of carbon dioxide.
- Part B The above phosphorized reaction product was dispersed in a light hydrocarbon and reacted with sulfur for about 2 to 4 hours at between about 350 F. and 400 F. with constant stirring until the reaction was complete. The sludge formed during the reaction was removed and the sulfurized reaction product was recovered by extraction. It was soluble in mineral oil and contained a substantial amount of chemically bond sulfur and a minute amount of phosphorus.
- Example I A mixture of a ketone as used in Example I and phosphorus were reacted under the, conditions and isolated in the manner indicated in Example I (Part A). This phosphorized product was then reacted with sulfur for about four hours at between about 350 F. and 400 F. with constant stirring until the reaction was completed. The resultant product contained a substantial amount of sulfur and was readily soluble in mineral oil.
- EXAMPLE III Approximately 10 parts of the reaction product of Example II was dissolved in a desired amount of mineral lubricating oil by gentle heating at about 190 F. to 212 F. To the mixture about parts of lime was added and a minor amount of water and the product heated for about two to three hours at about 212 F. The mixture was filtered to remove excess lime and the filtrate reheated for about two hours at between 250 and 270 F. A stream of nitrogen gas was blown through the mixture to remove entrained foreign matter, moisture and the like. This concentrate of Ca salt of the reaction product of this invention may be diluted with a desired mineral oil and used as an improved lubricant.
- Reaction products of this invention are noncorrosive, possess the property of stabilizing lubricants against deterioration, and inhibit engine wear.
- Reaction products 01' this invention are excellent oil improving agents, imparting to oil fllm strength and extreme pressure properties as well as stabilizing said 011 against oxidation, corrosion, deterioration and the like.
- Reaction products of this invention can be used as valuable additives to or constituents of heavy duty oils, motor oils, Diesel oils, aviation oils, synthetic oils, and the like, because of their anti-corrosion, anti-oxidation, and anti-wear properties.
- the reaction products of this invention may be used as stabilizing agents for other organic materials such as rubber, fuels, fatty oils, greases and the like.
- the amount of additive used can be varied over relatively wide limits but generally it is not necessary to use more than 5% by weight of the reaction product and preferably only between about 0.1% to 2.0% by weight is added to base lubricants.
- the reaction product of this invention can be combined with other additives in lubricants, such as blooming agents, pour point depressants, viscosity improvers, extreme pressure agents, anti-foaming agents, and the like.
- oil-soluble detergents which include oil-soluble salts of various bases with detergent-forming acids.
- bases include metal as well as organic bases.
- Metallic bases includes the hydroxides, etc. of the alkali metals, Cu, Mg, Ca, Sr, Ba, Zn, Cd, A1, Sn, Pb, Cr, Mn, Fe, Ni, Co, etc.
- Organic bases include various nitrogen bases as primary, secondary, tertiary and quaternary amines.
- detergent forming acids are the various fatty acids of, say 10 to 30 carbon atoms, wool fat acids, paraffin wax acids (produced by oxidation of paraiiln wax), chlorinated fatty acids, rosin acids, aromatic carboxylic acids including aromatic fatty acids, aromatic hydroxy fatty acids, parafiln wax benzoic acids, various alkyl salicyclic acids, phthalic acid monoesters, aromatic keto acids, aromatic ether acids; diphenols as di(alkyl phenol) sulfides and di-sulfides, methylene bis alkyl phenols; sulfonic acids such as may be produced by treatment of' alkyl aryl hydrocarbons or high boiling petroleum oils with sulfuric acid; sulfuric acid mono-esters; phosphoric, arsenic and antimony acid mono and di-esters, including the corresponding thiophosphoric, arsenic and antimony acids; phosphonic and arsenic acids and the like.
- Additional detergents are the alkaline earth phosphate di-esters, including the thiophosphate di-ester; the alkaline earth diphenolates, specifically the calcium and barium salts of diphenol mono and polysulfides.
- Non-metallic detergents include compounds such as the phosphatides such as lecithin and cepholin, certain fatty oils as rapeseed oils, volatilized fatty or mineral oils and the like.
- An excellent metallic detergentfor the present purpose is the calcium salt of oil-soluble petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash. Also alkaline metal salts of alkyl phenol-aldehyde condensation reaction products are excellent detergents.
- Anti-oxidants comprise several types, for example, alkyl phenols such as 2,4,6-trimethyl phenol, pentamethyl phenol, 2,4-dimethyl-6-ter tiary butyl phenol, 2,4-dimethyl-6-octyl phenol, 2,6-ditertiary butyl-4-Inethyl phenol, 2,4,6-tritertiary butyl phenol and the like; amino phenols as benzyl amino phenols; amines such as dibutylphenylene diamine, diphenyl amine, phenyl-betanaphthyl amine, phenyl-alpha-naphthyl amine, dinaphthyl amine.
- alkyl phenols such as 2,4,6-trimethyl phenol, pentamethyl phenol, 2,4-dimethyl-6-ter tiary butyl phenol, 2,4-dimethyl-6-octyl phenol, 2,6-
- Corrosion inhibitors or anti-rusting compounds may also be present, such as dicarboxylic acids of 16 and more carbon atoms; alkali metal and alkaline earth salts of sulfonic acids and fatty acids; organic compounds containing an acidic radical in close proximity to a nitrile, nitro or nitroso group (e. g. alpha cyano stearic acid).
- Extreme pressure agents which may be used comprise: esters of phosphorous acids such as triaryl, alkyl hydroxy aryl, or aralkyl phosphates, thiophosphates or phosphites and the like; neutral aromatic sulfur compounds of relatively high boiling temperatures such as diaryl sulfides, diaryl disulfides, alkyl aryl disulfides, e. g.
- diphenyl sulfide diphenol sulfide, dicresol sulfide, dixylenol sulfide, methyl butyl diphenol sulfide, dibenzyl sulfide, corresponding diand trisulfides, and the like; sulfurized fatty oils or estersof fatty acids and monohydric alcohols, e. g.
- sulfurized long chain olefins such as may be obtained by dehydrogenation or cracking of wax
- chlorinated hydrocarbons such as chlorinated paraffin, aromatic hydrocarbons, terpenes, mineral lubricating oil, etc., or chlorinated esters of fatty acids containing the chlorine in position other than alpha position.
- Additional ingredients may comprise oil-soluble urea or thiourea derivative, e. g. urethanes, allophates, carbazides, carbazones, etc., polyisobutylene polymers, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds.
- oil-soluble urea or thiourea derivative e. g. urethanes, allophates, carbazides, carbazones, etc.
- polyisobutylene polymers unsaturated polymerized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds.
- the amount of additive used may vary from 0.01% to 2% or higher. However, substantial improvement is obtained by using amounts ranging from 0.1% to 0.5% in combination with phosphorus sulfide-unsaturated cyclic ketone reaction products of this invention.
- a composition comprising a major amount of an oleaginous lubricating material and between about 0.1% and of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., a sulfur-free phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1 :2 to 1:8, and thereafter treating the resulting reaction product with a suifurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a composition comprising a major amount of an oleaginous lubricating material and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature'ranging from 170 F. to about 350 F., a sulfur-free phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms and derived from condensation of acetone to higher molecular weight isophorone type products in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.521 to 1: at a temperature ranging from 240 to 450 F.
- a composition comprising a major amount of an oleaginous lubricating material and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature ranging from F. to about 350 F., a phosphorus oxide with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating .the resulting reaction product with sulfur in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., a phosphorus oxide with a high molecular weigh unsaturated cyclic ketone fraction containing a least 12 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in a ratio of from 0.5:1
- a composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., phosphorus pentoxide with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in the ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., phosphorus pentoxide wlth a high molecular weight unsaturated cyclic ketone fraction containing at least 18 carbon atoms in a ratio 01 from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a composition comprising a major amount of an oleaginous lubricating material and between about 0.1% and 5% of a metal salt of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., a sulfurfree phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1:2 to 1:8 and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a metal salt of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., phosphorus pentoxide with a high molecular weight unsaturated cyclic ketone fraction containing at least 18 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a calcium salt of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., phosphorus pentoxide with a high molecular weight unsaturated cyclic ketone fraction containing at least 18 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a composition comprising a major amount of an oleaginous lubricating material and a minor amount sufiicient to stabilize said oleaginous material against deterioration and corrosion of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., a sulfur-free phosphorizl'ng agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a process of producing a stable, non-corrosive reaction product comprising reacting at a temperature ranging from 170 F. to about 350 F. a sulfur-free phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms, in a ratio of from 1:2 to 1:8, and thereafter treating th resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to450 F.
- a process of producing a stable, non-corrosive reaction product comprising reacting at a temperature ranging from 170 F. to about 350 F. a sulfur-free phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms, in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F., and finally neutralizing th product with a metal compound.
- a sulfur-free phosphorus-containing unsaturated cyclic ketone fraction having at least 12 carbon atoms in the molecule obtained by reacting said unsaturated cyclic ketone fraction with a sulfur-free phosphorizing agent in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
- a metal salt of a sulfur-free phosphorus-containing unsaturated cyclic ketone fraction having at least 12 carbon atoms in the molecule obtained by reacting said unsaturated cyclic ketone fraction with a sulfurfree phosphorizing agent in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F., and finally neutralizing the product with a metal compound.
- a calcium salt of a sulfur-free phosphorus-containing unsaturated cyclic ketone fraction having at least 12 carbon atoms in the molecule obtained by reacting said unsaturated cyclic ketone fraction with a sulfurfree phosphorizing agent in a ratio of from 1:2 to 1:8, thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F., and finally neutralizing the product with a calcium compound.
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Description
Patented Apr. 4, 1950 LUBRICATING COMPOSITION David E. Adelson, Berkeley, Calif., assignor to Shell Development Company, San Francisco, Calif., a corporation of Delaware No Drawing. ,Application October 24, 1947, Serial No. 782,044
Claims. 1
This invention relates to new and novel products which have properties of greatly improving and stabilizing lubricants. More particularly, this invention pertains to oleaginous materials, especially lubricants, such as mineral lubricating oils, synthetic lubricants of hydrocarbon and non-hydrocarbon origin, and the like, containing a multi-functional additive having detergent and anti-ringsticking properties, which additive also acts as an inhibitor of oxidation and corrosion.
It is ,well known that various lubricants, whether doped or undoped, tend to oxidize and form corrosive bodies and sludge when used in modern engines and machines operating under ordinary conditions, and especially at high speeds, elevated temperatures, heavy loads and other adverse conditions. Also, as lubricants deteriorate during use, hard carbonaceous materials are formed on engine and machine parts, causing scratching and scuffing of movable metal parts, and sticking of valves and piston rings in engines. In addition, lubricants prepared and sold until now are generally incapable of maintaining a continuous lubricating film between movable metal parts; this results in a gradual or even rapid wearing away of the metal parts. The damage thus caused requires replacement of such parts, or even a complete overhauling of the engines-and machines, resulting in expensive loss I of production and time.
In the case of the highest quality non-corrosive, stable undoped mineral lubricating oils, which are highly refined for specific uses, or synthetic lubricants developed for special uses, it has been found that such oils and lubricants are generally highly susceptible to oxidation and deterioration, becoming progressively more and more corrosive in engines and machines even under ordinary operating conditions.
To improve the lubricating properties of oils and synthetic lubricants, it has become the practice to blend therewith one or more additives which have the effect or property of inhibiting deterioration of lubricants and impart to them certain beneficial properties. Thus additives have been specifically designed which have the property of inhibiting corrosion of alloyed bearings such as copper-lead, cadmium-silver and the like, developed for automotive, Diesel and aircraft engines. Acidic oxidation or decomposition components formedin lubricants during use can readily attack these bearings, but are inhibited or prevented from doing this by the formation of a corrosion protective film formed with the aid of the additive on the bearing surface. Additives have also been developed which possess the property of modifying the carbonaceous materials formed by deterioration of lubricants on piston rods, rings and valves and other metal parts in internal combustion engines, automotive and truck engines, aviation engines, high speed Diesel engines, and the like. These additives serve a very important function because by modifying this carbonaceous material so that it can be removed easily, the tendency of engine parts to become stuck is inhibited; ringsticking, piston scufiing and scratching and wearing away of other parts and material reduction of engine efliciency is thereby prevented.
Other additives have been developed which act as detergents in order to assist in the removal of soot, sludge, varnish, and/or lacquer formed from deterioration of the oil at high operating temperatures. Detergents, due to their cleansing action, prevent the build-up of these deleterious materials and assist in removing those formed. Anti-wear additives have the property of reducing friction of movable metal parts of the same or different metals. Due to the function exerted or property imparted by such additives on lubricants, wear caused by direct frictional contact of metals can be greatly reduced. Also additives have been developed for withstanding extreme pressures, dispersion of impurities, solubilizing of certain other additives, etc.
The large number of additives thus developed has been due to the fact that an additive is capable of functioning mainly in only one specific manner: very few lubricant additives have the ability of improving a lubricant in more than just one respect. Thus, a good anti-oxidant might not be able to inhibit lacqu'er and varnish formation on piston rods, or to act as a detergent or corrosion inhibitor. In many cases, it is found that whereas an additive possesses very good properties in one respect, this same additive is the cause of harmful deposits in another respect. A second and third additive is therefore frequcntly required in order to obtain a good stable lubricant. The combination of additives in lubricants wherein each additive exerts its influence without interfering with the function of other additives present is a difficult matter to attain because in most cases additives co-react or interfere with each other. occurring great care must be taken in selecting the additives, mixing them in specific proportions, and continuously watching and replacing additives which have stopped functioning or have deteriorated.
To prevent this from I to add to mineral lubricating oils, synthetic lubricants, and" the like, a multi functional material so as to inhibit oxidation and corrosion and prevent the formation of sludge, varnish and lacquer in said lubricants even under adverse operating conditions. Still another object of this invention is to use in lubricating compositions a material which prevents ringsticking as well as the sticking of other engine parts due to deterioration of the lubricant. Also it is an object of this'invention to use in lubricating compositions a material which inhibits wear, scuifing, scratching and other damage to engine parts. another object of this invention to provide novel compounds which possess multi-functional improving and enhancing properties when added to lubricants.
The above and other objects may be attained in accordance with the present invention by adding to oleaginous materials, e. g. various lubricating bases, a minor amount of a reaction product obtained by treating a saturated or unsaturated cyclic ketone fraction having at least 12 and preferably more than 18 carbon atoms in ,the molecule (which ketone fractions may be obtained from isophorone bottoms during its synthesis fIOm acetone by condensation as well as from other sources) with a phosphorus compound which is free from sulfur, and thereafter subjecting said phosphorized cyclic ketone to a sulfurization treatment at an elevated temperature. This reaction product may also be further treated with any, suitable metal such as alkali metals, alkaline earth metals, heavy metals, nitrogen containing organic bases and the like. Specifically, the above reaction product may be treated with such a compound as a hydroxide, carbonate or oxide'of Na, Li, K, Ca, Ba, Sr, Mg, Al, Zn, Cu, Cr, Cd, Fe, Mn, Ni, Sn, etc., or basic reagents such as ammonia, alkyl of aryl substituted ammonia, such as amines, quaternary ammonium compounds and the like.
The preferred ketones used to obtain the oil additive of this invention are the unsaturated cyclic ketones normally obtained from isophorone bottoms produced by condensation of acetone under elevated temperature and pressure. The isophorone bottoms thus produced may be fractionated into various cuts each of which may be used to form the reaction product of this invention. Among the specific isophorone fractions which may be used are topped crude isophorone bottoms, topped crude hydrolyzed isophorone bottoms, and the like.
The terms topped crude isophorone bottoms and topped crude hydrolyzed isophorone bottoms, and similar terms, which will be hereinafter used and fully described are generic and are used to identify various unsaturated cyclic ketone fractions of relatively high molecular weight obtained from acetone condensation. Unsaturated cyclic ketone fractions useable in reactions of the kind under consideration may be obtained by condensing acetone in 30% to 60% caustic so- It is still.
subjected to distillation to remove low boiling ketones having less than about 12 carbon atoms and other constituents and impurities. The product remaining in the still is purified by filtration, solvent treatment or the like, and comprises crude unsaturated cyclic ketones of high lution at a temperature ranging betweenmolecular weight, referred to herein as crude isophorone bottoms. The term isophorone bottoms as referred to herein is thus a complex mixture of high molecular weight unsaturated cyclic ketones containing at least 12 and preferably more than 18 carbon atoms in the molecule. The product formed is not to be confused with straight isophorone which is specifically 3,5,5-trimethyl cyclohexene-2-one-1, an unsaturated cyclic ketone containing only nine carbon atoms in the molecule. Isophorone bottoms produced by condensation of acetone under conditions referred to above included within itsscope any and all unsaturated cyclic ketones containing at least 12 and preferably more than 18 carbon atoms and having generally the chemical structural configcrude isophorone bottoms are topped crude isophorone bottoms which contain at least 15 carbon atoms in the molecule and which are obtained after removal of distillate from crude isophorone bottoms to a still head temperature of 284 F. at 10 mm. Hg pressure. Crude isophorone bottoms can be subected to hydrolysis with dilute sodium hydroxide, and the acetone and isophorone formed removed by distillation. The bottoms can then be filtered and purified and comprise essentially unsaturated cyclic ketones containing at least 12 carbon atoms in the molecule; these are referred to herein as crude hydrolyzed isophorone bottoms. This material can be subjected to distillation to split it into two fractions. The distilled hydrolyzed isophorone fraction has a boiling point of about 140 C. at 10 mm. Hg pressure and consists of a mixture of unsaturated cyclic ketones containing between 15 and 18 carbon atoms in the molecule. The residue is referred to as topped crude hydrolyzed isophorone bottoms, which is similar to topped crude isophorone bottoms. This residue comprises essentially unsaturated cyclic ketones of at least 15 carbon atoms in the molecule; Crude isophorone bottoms can be also subjected to condensation over solid sodium hydroxide to yield two types of resinous materials. The first resinous fraction or soft resin has a viscosity at 210 F. of about 25-26 centistokes and an average molecular weight of 320 to 350. The heavier fraction or medium resin has a viscosity at 210 F. of about to centistokes and an average molecular weight of 370 to 390. All of the various unsaturated cyclic ketone fractions obtained in the manner fully described above can be used for reacting with phosphorus sulfide to form a multi-functional lubricating additive. Other cyclic ketones having at least 12 carbon atoms are obtained by hydrogenating the above unsaturated cyclic ketones to obtain saturated cyclic ketones having at least 12 carbon atoms, alkyl cyclohexanone, i. e. dibutyl cyclohexanone, alkyl substituted carvomenthone, menthone, pulegone,
carvone, camphor, and the like having at least 12 carbon atoms.
The phosphorizlng agent which can be used to form the initial reaction product of this invention may be any sulfur-free phosphorus containing compound capable of reacting and introducing phosphorus into acyclic ketone. Specific phosphorizing agents may include elemental phosphorus, the phosphorus halides, oxyhalides, compounds of the oxygen family, e. g. P205, P203, etc.; metallic phosphides such as sodium or tin phosphides; phosphoric acid anhydride, said anhydride generally being accelerated by addition of acetyl chloride; phosphoric acid and the like.
The type of pho-sphorizing agent used, the ratio of the two reactants, the temperature, time and condition under which the reaction is to be carried out, as well as the manner in which the reaction product is recovered, may be varied within the limits described herein provided the phosphorus-chemically combines with the cyclic ketone of this invention. Phosphorization may be carried out in an inert solvent and/or under inert conditions, and depending upon the nature of the two reacting materials the temperature may vary between about 170 F. and about 350 F., although the range of 200F. to 250 F. is preferred.
The preferred phosphorizing agents are elemental phosphorus and phosphorus pentoxide, and the preferred ketone fractions which are reacted with said phosphorizing agents are topped crude isophorone bottoms which are residues remaining after removal of distillate from crude isophorone bottoms to a still head temperature of 284 F. at mm. Hg pressure, and comprising unsaturated cyclic ketones containing at least carbon atoms in the molecule. Another preferred fraction is a topped crude hydrolyzed isophorone bottoms obtained from crude hydrolyzed isophorone bottoms, similar to the topped crude isophorone bottoms. The term topped used throughout has the same meaning as in the petroleum art, namely, a distillation or fractionation step, whereby certain materials are removed as an overhead fraction.
The mol ratio of the phosphorizing agent to ketone may vary from about 1:2 to about 1:4, and even to about 1:8, of the phosphorizing agent to ketone depending upon the reactivity of the reactants. Also in carrying out the reaction it is advisable to initially control the reaction so that the temperature does not rise too rapidly. Generally it is preferred to keep the reaction at below 176 F. until all the reactants have been added and the reaction proceeds smoothly. Thereafter the temperature can be raised rapidly to the desired or optimum temperature.
Although not essential, the reaction should be carried out in a substantially inert atmosphere, and the two materials can be reacted per se or disposed in a suitable inert or non-reactive diluent and then reacted under conditions described above. This reaction product may be purified before subjecting it to the next reaction step or the crude product may be subjected to a sulfurization process which is the next step and thereafter recovered and purified.
The sulfurization of the phosphorized reaction product of the inventionis carried out at an elevated temperature and the sulfurizing agent may be selected from the class consisting of elemental sulfur, flowers of sulfur, sulfur halides,
- non-corrosive.
alkali polysiilflde, ammonium hydrogen sulfidehydrogen sulfide, sulfur dioxide and the like. Although the mol ratio of the sulfurizing agent such as sulfur and phosphorized cyclic ketone may be varied over wide limits, it is preferable to keep said reactants in a moi ratio of from about 0.5:1 to about 1:1.
The reaction should be carried out in substantially inert atmosphere .at a temperature of between about 250 F. and about 450 F., and preferably between 300 F. and 350 F. The sulfurization of the initial reaction product, namely a phosphorized ketone, may be carried cut progressively in the same-vessel, by simply adding the required amount of sulfur or the like and adjusting the reaction condition. Iithe initial reaction product has been purified first, it may be redispersed in a suitable diluent and then reacted with sulfur or the like in the manner described.
The exact mechanism of the sulfurization process is at present not understood. It appears however that the sulfur substantially replaces the phosphorus in the reaction product and becomes bonded in such a manner to the ketone as to be A great deal more sulfur enters into the reaction by this process than if cyclic ketone were simply sulfurized. It might be surmised that the sulfur causes the phosphorus to split out of the initial reaction resulting in an increase in the degree of unsaturation of the ketone thereby allowing more sulfur to react with the ketone. The final reaction product contains a major or substantial amount of chemically bond sulfur and a minor or minute amount of phosphorus which appears to be in the form of entrained material rather than as a chemically bond constituent of the final reaction product of this invention.
The final reaction product of this invention may be neutralized by treatment with-a suitable basic compound such as hydroxide, oxide or carbonate of an alkaline earth metal, alkali metal or other suitable basic reagent such as ammonia, alkyl or aryl amines, quaternary ammonium compounds or heavy metals such as Al, Cr, Fe, Sn and the like. Preferred reagents are Ca, Ba, Mg, Na, K, Al and Zn.
The entire reaction procedure of this invention is relatively simple and requires no elaborate or special equipment, undueprecaution or skill. The obtainment of the initial reaction product simply requires stirring an unsaturated cyclic ketone with phosphorus or phosphorus pentoxide, in an inert atmosphere, such as nitrogen or carbon dioxide. The temperature of the reaction should be increased gradually up to about F.
and maintained there until the reaction proceeds in an orderly manner. Thereafter it can be increased rapidly to above 300 Rand maintained there until the reaction is complete. The reaction product may be extracted with a non-aromatic solvent and the extracting medium removed by distillation or the like. The phosphorized ketone is then dispersed in a suitable solvent and a calculated amount of sulfur added under inert conditions and the mixture reacted for 2 to 8 hours at a temperature above about 250 F. to 300 F. or higher. The sludge like material formed during the reaction is removed and the product purified by solvent extraction, blowing and washing. If desired salts may be formed by agitating the reaction product in a suitable diluent such as mineral oil with a calculated amount of lime or any other desired neutralizing 7 agent at a temperature of above about 250 F. for about 2 hours. A stream of inert gas is usually blown through the mixture to remove any entrained moisture or other contaminates. The neutralized reaction product can be recovered from the oil by filtration and may be refiltered to remove excess lime, and other impurities.
To more clearly illustrate the present invention, the following examples are presented. It is to be understood, however, that various modifications can be resorted to without departing from the spirit of the invention as presented in the subjoined claims.
EXAMPLE I Part A A mixture of approximately, one mol of cyclic unsaturated ketones containing at least 18 carbon atoms in the molecule, obtained by topping bottoms from crude isophorone bottoms at a kettle temperature of between about 284 F. and mm. Hg pressure, and one mol of phosphorus pentoxide were stirred and heated in an inert atmosphere of carbon dioxide for about five hours at around 200 F. The mixture was initially maintained at about 140 F. and then heated to about 300 F. At the end of the reaction period, the reaction product was extracted with a non-aromatic hydrocarbon and the solvent removed by evaporation at steam temperature in a current of carbon dioxide.
Part B The above phosphorized reaction product was dispersed in a light hydrocarbon and reacted with sulfur for about 2 to 4 hours at between about 350 F. and 400 F. with constant stirring until the reaction was complete. The sludge formed during the reaction was removed and the sulfurized reaction product was recovered by extraction. It was soluble in mineral oil and contained a substantial amount of chemically bond sulfur and a minute amount of phosphorus.
EXAIVIPLEII A mixture of a ketone as used in Example I and phosphorus were reacted under the, conditions and isolated in the manner indicated in Example I (Part A). This phosphorized product was then reacted with sulfur for about four hours at between about 350 F. and 400 F. with constant stirring until the reaction was completed. The resultant product contained a substantial amount of sulfur and was readily soluble in mineral oil.
EXAMPLE III Approximately 10 parts of the reaction product of Example II was dissolved in a desired amount of mineral lubricating oil by gentle heating at about 190 F. to 212 F. To the mixture about parts of lime was added and a minor amount of water and the product heated for about two to three hours at about 212 F. The mixture was filtered to remove excess lime and the filtrate reheated for about two hours at between 250 and 270 F. A stream of nitrogen gas was blown through the mixture to remove entrained foreign matter, moisture and the like. This concentrate of Ca salt of the reaction product of this invention may be diluted with a desired mineral oil and used as an improved lubricant.
Reaction products of this invention are noncorrosive, possess the property of stabilizing lubricants against deterioration, and inhibit engine wear. I
Reaction products 01' this invention are excellent oil improving agents, imparting to oil fllm strength and extreme pressure properties as well as stabilizing said 011 against oxidation, corrosion, deterioration and the like.
Reaction products of this invention can be used as valuable additives to or constituents of heavy duty oils, motor oils, Diesel oils, aviation oils, synthetic oils, and the like, because of their anti-corrosion, anti-oxidation, and anti-wear properties. In addition, the reaction products of this invention may be used as stabilizing agents for other organic materials such as rubber, fuels, fatty oils, greases and the like. The amount of additive used can be varied over relatively wide limits but generally it is not necessary to use more than 5% by weight of the reaction product and preferably only between about 0.1% to 2.0% by weight is added to base lubricants.
The reaction product of this invention can be combined with other additives in lubricants, such as blooming agents, pour point depressants, viscosity improvers, extreme pressure agents, anti-foaming agents, and the like. Among the specific additives which can be used are oil-soluble detergents which include oil-soluble salts of various bases with detergent-forming acids. Such bases include metal as well as organic bases. Metallic bases includes the hydroxides, etc. of the alkali metals, Cu, Mg, Ca, Sr, Ba, Zn, Cd, A1, Sn, Pb, Cr, Mn, Fe, Ni, Co, etc. Organic bases include various nitrogen bases as primary, secondary, tertiary and quaternary amines.
Examples of detergent forming acids are the various fatty acids of, say 10 to 30 carbon atoms, wool fat acids, paraffin wax acids (produced by oxidation of paraiiln wax), chlorinated fatty acids, rosin acids, aromatic carboxylic acids including aromatic fatty acids, aromatic hydroxy fatty acids, parafiln wax benzoic acids, various alkyl salicyclic acids, phthalic acid monoesters, aromatic keto acids, aromatic ether acids; diphenols as di(alkyl phenol) sulfides and di-sulfides, methylene bis alkyl phenols; sulfonic acids such as may be produced by treatment of' alkyl aryl hydrocarbons or high boiling petroleum oils with sulfuric acid; sulfuric acid mono-esters; phosphoric, arsenic and antimony acid mono and di-esters, including the corresponding thiophosphoric, arsenic and antimony acids; phosphonic and arsenic acids and the like.
Additional detergents are the alkaline earth phosphate di-esters, including the thiophosphate di-ester; the alkaline earth diphenolates, specifically the calcium and barium salts of diphenol mono and polysulfides.
Non-metallic detergents include compounds such as the phosphatides such as lecithin and cepholin, certain fatty oils as rapeseed oils, volatilized fatty or mineral oils and the like.
An excellent metallic detergentfor the present purpose is the calcium salt of oil-soluble petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash. Also alkaline metal salts of alkyl phenol-aldehyde condensation reaction products are excellent detergents.
Anti-oxidants comprise several types, for example, alkyl phenols such as 2,4,6-trimethyl phenol, pentamethyl phenol, 2,4-dimethyl-6-ter tiary butyl phenol, 2,4-dimethyl-6-octyl phenol, 2,6-ditertiary butyl-4-Inethyl phenol, 2,4,6-tritertiary butyl phenol and the like; amino phenols as benzyl amino phenols; amines such as dibutylphenylene diamine, diphenyl amine, phenyl-betanaphthyl amine, phenyl-alpha-naphthyl amine, dinaphthyl amine.
Corrosion inhibitors or anti-rusting compounds may also be present, such as dicarboxylic acids of 16 and more carbon atoms; alkali metal and alkaline earth salts of sulfonic acids and fatty acids; organic compounds containing an acidic radical in close proximity to a nitrile, nitro or nitroso group (e. g. alpha cyano stearic acid).
Extreme pressure agents which may be used comprise: esters of phosphorous acids such as triaryl, alkyl hydroxy aryl, or aralkyl phosphates, thiophosphates or phosphites and the like; neutral aromatic sulfur compounds of relatively high boiling temperatures such as diaryl sulfides, diaryl disulfides, alkyl aryl disulfides, e. g. diphenyl sulfide, diphenol sulfide, dicresol sulfide, dixylenol sulfide, methyl butyl diphenol sulfide, dibenzyl sulfide, corresponding diand trisulfides, and the like; sulfurized fatty oils or estersof fatty acids and monohydric alcohols, e. g. sperm oil, jojoba oil, etc., in which the sulfur is strongly bonded; sulfurized long chain olefins such as may be obtained by dehydrogenation or cracking of wax; sulfurized phosphorized fatty oils or acids, phosphorous acid esters having sulfurized organic radicals, such as esters of phosphoric or phosphorous acids with sulfurized hydroxy fatty acids; chlorinated hydrocarbons such as chlorinated paraffin, aromatic hydrocarbons, terpenes, mineral lubricating oil, etc., or chlorinated esters of fatty acids containing the chlorine in position other than alpha position.
Additional ingredients may comprise oil-soluble urea or thiourea derivative, e. g. urethanes, allophates, carbazides, carbazones, etc., polyisobutylene polymers, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds.
Depending upon the additive used and conditions under which it is used, the amount of additive used may vary from 0.01% to 2% or higher. However, substantial improvement is obtained by using amounts ranging from 0.1% to 0.5% in combination with phosphorus sulfide-unsaturated cyclic ketone reaction products of this invention.
It is to be understood that while the features of the invention have been described and illustrated in connection with certain specific examples, the invention, however, is not to be limited thereto or otherwise restricted, except by the prior art and the scope of the appended claims.
I claim as my invention:
' 1. A composition comprising a major amount of an oleaginous lubricating material and between about 0.1% and of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., a sulfur-free phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1 :2 to 1:8, and thereafter treating the resulting reaction product with a suifurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
2. A composition comprising a major amount of an oleaginous lubricating material and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature'ranging from 170 F. to about 350 F., a sulfur-free phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms and derived from condensation of acetone to higher molecular weight isophorone type products in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.521 to 1: at a temperature ranging from 240 to 450 F.
3. A composition comprising a major amount of an oleaginous lubricating material and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature ranging from F. to about 350 F., a phosphorus oxide with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating .the resulting reaction product with sulfur in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
4. A composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., a phosphorus oxide with a high molecular weigh unsaturated cyclic ketone fraction containing a least 12 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in a ratio of from 0.5:1
to 1: at a temperature ranging from 240 to 5. A composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., phosphorus pentoxide with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in the ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
6. A composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., phosphorus pentoxide wlth a high molecular weight unsaturated cyclic ketone fraction containing at least 18 carbon atoms in a ratio 01 from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
7. A composition comprising a major amount of an oleaginous lubricating material and between about 0.1% and 5% of a metal salt of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., a sulfurfree phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1:2 to 1:8 and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
8. A composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a metal salt of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., phosphorus pentoxide with a high molecular weight unsaturated cyclic ketone fraction containing at least 18 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
9. A composition comprising a major amount of a mineral oil and between about 0.1% and 5% of a calcium salt of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., phosphorus pentoxide with a high molecular weight unsaturated cyclic ketone fraction containing at least 18 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with sulfur in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
10. A composition comprising a major amount of an oleaginous lubricating material and a minor amount sufiicient to stabilize said oleaginous material against deterioration and corrosion of a reaction product obtained by reacting at a temperature ranging from 170 F. to about 350 F., a sulfur-free phosphorizl'ng agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
11. A process of producing a stable, non-corrosive reaction product comprising reacting at a temperature ranging from 170 F. to about 350 F. a sulfur-free phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms, in a ratio of from 1:2 to 1:8, and thereafter treating th resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to450 F.
12. A process of producing a stable, non-corrosive reaction product comprising reacting at a temperature ranging from 170 F. to about 350 F. a sulfur-free phosphorizing agent with a high molecular weight unsaturated cyclic ketone fraction containing at least 12 carbon atoms, in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F., and finally neutralizing th product with a metal compound.
13. As a new composition, a sulfur-free phosphorus-containing unsaturated cyclic ketone fraction having at least 12 carbon atoms in the molecule obtained by reacting said unsaturated cyclic ketone fraction with a sulfur-free phosphorizing agent in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F.
14. As a new composition, a metal salt of a sulfur-free phosphorus-containing unsaturated cyclic ketone fraction having at least 12 carbon atoms in the molecule obtained by reacting said unsaturated cyclic ketone fraction with a sulfurfree phosphorizing agent in a ratio of from 1:2 to 1:8, and thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F., and finally neutralizing the product with a metal compound.
15. As a new composition, a calcium salt of a sulfur-free phosphorus-containing unsaturated cyclic ketone fraction having at least 12 carbon atoms in the molecule obtained by reacting said unsaturated cyclic ketone fraction with a sulfurfree phosphorizing agent in a ratio of from 1:2 to 1:8, thereafter treating the resulting reaction product with a sulfurizing agent in a ratio of from 0.5:1 to 1:1, at a temperature ranging from 240 to 450 F., and finally neutralizing the product with a calcium compound.
DAVID E. ADELSON;
REFERENCES CITED The following references are of record in the Otto t al Jan. 11, 1949
Claims (2)
1. A COMPOSITION COMPRISING A MAJOR AMOUNT OF AN OLEAGINOUS LUBRICATING MATERIAL AND BETWEEN ABOUT 0.1% AND 5% OF A REACTION PRODUCT OBTAINED BY REACTING AT A TEMPERATURE RANGING FROM 170* F. TO ABOUT 350*F., A SULFUR-FREE PHOSPHORIZING AGENT WITH A HIGH MOLECULAR WEIGHT UNSATURATED CYCLIC KETONE FRACTION CONTAINING AT LEAST 12 CARBON ATOMS IN A RATIO OF FROM 1:2 TO 1:8, AND THEREAFTER TREATING THE RESULTING REACTION PRODUCT WITH A SULFURIZING AGENT IN A RATIO OF FROM 0.5:1 TO 1:1, AT A TEMPERATURE RANGING FROM 240* TO 450*F.
7. A COMPOSITION COMPRISING A MAJOR AMOUNT OF AN OLEAGINOUS LUBRICATING MATERIAL AND BETWEEN ABOUT 0.1% AND 5% OF A METAL SALT OF A REACTION PRODUCT OBTAINED BY REACTING AT A TEMPERATURE RANGING FROM 170*F. TO ABOUT 350*F., A SULFURFREE PHOSPHORIZING AGENT WITH A HIGH MOLECULAR WEIGHT UNSATURATED CYCLIC KETONE FRACTION CONTAINING AT LEAST 12 CARBON ATOMS IN A RATIO OF FROM 1:2 TO 1:8 AND THEREAFTER TREATING THE RESULTING REACTION PRODUCT WITH A SULFURIZING AGENT IN A RATIO OF FROM 0.5:1 TO 1:1, AT A TEMPERATURE RANGING FROM 240* TO 450*F.
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US782044A US2502408A (en) | 1947-10-24 | 1947-10-24 | Lubricating composition |
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US2631129A (en) * | 1949-06-02 | 1953-03-10 | Tide Water Associated Oil Comp | Sulfurized tall oil-containing compositions |
US4154779A (en) * | 1976-03-04 | 1979-05-15 | Rhein-Chemie Rheinau Gmbh | Sulphurized phosphoric acid ester salts and method of preparation |
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US2383498A (en) * | 1943-07-10 | 1945-08-28 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2383494A (en) * | 1943-06-23 | 1945-08-28 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2383497A (en) * | 1943-07-08 | 1945-08-28 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2419153A (en) * | 1943-04-09 | 1947-04-15 | Standard Oil Co | Lubricant and the like |
US2459090A (en) * | 1945-07-25 | 1949-01-11 | Socony Vacuum Oil Co Inc | Products obtained by reacting phosphorus pentasulfide with sulfurized ketones |
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US2419153A (en) * | 1943-04-09 | 1947-04-15 | Standard Oil Co | Lubricant and the like |
US2383494A (en) * | 1943-06-23 | 1945-08-28 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2383497A (en) * | 1943-07-08 | 1945-08-28 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2383498A (en) * | 1943-07-10 | 1945-08-28 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2459090A (en) * | 1945-07-25 | 1949-01-11 | Socony Vacuum Oil Co Inc | Products obtained by reacting phosphorus pentasulfide with sulfurized ketones |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US2631129A (en) * | 1949-06-02 | 1953-03-10 | Tide Water Associated Oil Comp | Sulfurized tall oil-containing compositions |
US4154779A (en) * | 1976-03-04 | 1979-05-15 | Rhein-Chemie Rheinau Gmbh | Sulphurized phosphoric acid ester salts and method of preparation |
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