DE1225161B - Process for the production of polyol fatty acid esters serving as high-performance lubricants - Google Patents
Process for the production of polyol fatty acid esters serving as high-performance lubricantsInfo
- Publication number
- DE1225161B DE1225161B DEC25865A DEC0025865A DE1225161B DE 1225161 B DE1225161 B DE 1225161B DE C25865 A DEC25865 A DE C25865A DE C0025865 A DEC0025865 A DE C0025865A DE 1225161 B DE1225161 B DE 1225161B
- Authority
- DE
- Germany
- Prior art keywords
- fatty acid
- weight
- percent
- polyol
- production
- 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.)
- Pending
Links
- -1 polyol fatty acid esters Chemical class 0.000 title claims description 21
- 229920005862 polyol Polymers 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 11
- 239000000194 fatty acid Substances 0.000 title claims description 11
- 229930195729 fatty acid Natural products 0.000 title claims description 11
- 239000000314 lubricant Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 3
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 14
- 239000002253 acid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- PBCCGCZHDKGPSH-UHFFFAOYSA-N 2-butoxy-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound CCCCOP1(=O)OCCO1 PBCCGCZHDKGPSH-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- SHXZNGNFRDVQCD-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;heptanoic acid Chemical compound CCCCCCC(O)=O.CCC(CO)(CO)CO SHXZNGNFRDVQCD-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- VOWPVJACXJNHBC-UHFFFAOYSA-N methyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OC)OC1=CC=CC=C1 VOWPVJACXJNHBC-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QJAVUVZBMMXBRO-UHFFFAOYSA-N tripentyl phosphate Chemical compound CCCCCOP(=O)(OCCCCC)OCCCCC QJAVUVZBMMXBRO-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/08—Ammonium or amine salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
- C10M139/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 having a silicon-to-carbon bond, e.g. silanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/045—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution and non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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Description
BUNDESREPUBLIK DEUTSCHLAND DEUTSCHES 'MTTWt PATENTAMTFEDERAL REPUBLIC OF GERMANY GERMAN 'MTTWt PATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. α.:Int. α .:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
C 07 cC 07 c
Deutsche Kl.: 12 ο -11German class: 12 ο -11
C 25865 IV b/12 ο
29. Dezember 1961
22. September 1966C 25865 IV b / 12 ο
December 29, 1961
September 22, 1966
Die Erfindung bezieht sich auf die Herstellung von Polyol-Fettsäureestern, die als Schmiermittel im Dauerbetrieb bei hohen Temperaturen verwendet werden können.The invention relates to the production of polyol fatty acid esters which are used as lubricants in the Continuous operation at high temperatures can be used.
Fettsäureester von Polyolen mit zwei oder mehr Methylolgruppen an einem einzelnen quaternären Kohlenstoffatom, wie Trimethylolpropan, Trimethyloläthan und Pentaerythrit, können bekanntlich als Schmiermittel bei hohen Temperaturen verwendet werden. So ist z. B. aus der französischen PatentschriftFatty acid esters of polyols with two or more methylol groups on a single quaternary Carbon atom such as trimethylolpropane, trimethylolethane and pentaerythritol can be known as Lubricants are used at high temperatures. So is z. B. from the French patent
1 239 027 ein Schmiermittel für Düsenmotoren bekannt, das durch Mischen eines Alkanoldiesters einer Alkandicarbonsäure mit dem Ester aus einem Polyol mit zwei oder mehr Methylolgruppen an einem quaternären Kohlenstoff und einer Alkansäure mit wenigstens 5 Kohlenstoffatomen oder mehreren Alkansäuren mit durchschnittlich wenigstens 5 Kohlenstoffatomen hergestellt wird. Bei den üblicherweise zur Herstellung dieser Ester angewendeten Verfahren werden jedoch Produkte erhalten, die unter den extrem scharfen oxydierenden Bedingungen, denen Schmiermittel in Hochleistungsstrahlturbinen für Flugzeuge ausgesetzt sind, als Schmiermittel versagen. Ferner werden Ausbeuten in der Größenordnung von nur 87 bis 89% erhalten.1 239 027 a lubricant for jet engines known, which by mixing an alkanol diester one Alkanedicarboxylic acid with the ester of a polyol with two or more methylol groups on a quaternary Carbon and an alkanoic acid having at least 5 carbon atoms or more alkanoic acids is made with an average of at least 5 carbon atoms. In the case of the However, the processes used to prepare these esters result in products falling under the extremely harsh oxidizing conditions encountered by lubricants in high performance jet turbines for aircraft are exposed to failure as lubricants. Furthermore, yields are in the order of magnitude of only got 87 to 89%.
Das erfindungsgemäße Verfahren zur Herstellung von als Hochleistungsschmiermittel dienenden Fettsäure-Polyolestern durch Umsetzung von Polyolen, die mindestens zwei, vorzugsweise drei an ein einziges quaternäres Kohlenstoffatom gebundene Methylolgruppen enthalten, mit gesättigten Fettsäuren mit 4 bis 12 Kohlenstoffatomen ist dadurch gekennzeichnet, daß man als Veresterungskatalysatoren Phosphorverbindungen der allgemeinen Formel O = P(OR)3 verwendet, in der R Wasserstoffatome, Alkyl-, Alkylen- oder Arylreste bedeuten, wobei jedoch nicht mehr alsThe process according to the invention for the production of fatty acid polyol esters serving as high-performance lubricants by reacting polyols which contain at least two, preferably three methylol groups bonded to a single quaternary carbon atom, with saturated fatty acids having 4 to 12 carbon atoms is characterized in that the esterification catalysts used are phosphorus compounds general formula O = P (OR) 3 used, in which R denotes hydrogen atoms, alkyl, alkylene or aryl radicals, but not more than
2 Sauerstoffatome an Arylresten gebunden sind. Man erhält hierbei eine Ausbeute von beispielsweise2 oxygen atoms are bonded to aryl radicals. A yield of, for example, is obtained
mehr als 93% eines Esters von außergewöhnlicher Beständigkeit gegenüber oxydierenden Bedingungen bei hohen Temperaturen. Die für die Zwecke der Erfindung verwendeten Phosphorverbindungen umfassen z. B. Phosphorsäure, deren Alkylteilester, Trialkyl-, Alkylenalkyl-, Alkylen-bis-(dialkyl)-, Monoaryldialkyl- und Diarylmonoalkylphosphate. Zu den Verbindungen, die vorzugsweise verwendet werden können, gehören außer Phosphorsäure Butylphosphorsäure, Dipropylphosphorsäure, Tripropylphosphat, Tributylphosphat, Triamylphosphat, Phenyldibutylphosphat, Diphenylmethylphosphat, Äthylenbutylphosphat und Äthylen-bis-(dibutylphosphat). Bevorzugt werden Trialkylphosphate, deren Alkylreste 1 bisgreater than 93% of an ester with exceptional resistance to oxidizing conditions at high temperatures. The phosphorus compounds used for the purpose of the invention include z. B. phosphoric acid, its partial alkyl esters, trialkyl, Alkylene alkyl, alkylene bis (dialkyl), monoaryldialkyl and diaryl monoalkyl phosphates. To the Compounds that can preferably be used include, besides phosphoric acid, butyl phosphoric acid, Dipropyl phosphoric acid, tripropyl phosphate, tributyl phosphate, triamyl phosphate, phenyl dibutyl phosphate, Diphenylmethyl phosphate, ethylene butyl phosphate and ethylene bis (dibutyl phosphate). Preferred are trialkyl phosphates whose alkyl radicals 1 to
Verfahren zur Herstellung von als Hochleistungsschmiermittel dienenden Polyol-FettsäureesternProcess for the production of as a high-performance lubricant serving polyol fatty acid esters
Anmelder:Applicant:
Celanese Corporation of America,Celanese Corporation of America,
New York, N. Y. (V. St. A.)New York, N.Y. (V. St. A.)
Vertreter:Representative:
Dr.-Ing. A. ν. Kreisler, Dr.-Ing. K. Schönwald,
Dr.-Ing. Th. Meyer und Dr. J. F. Fues,
Patentanwälte, Köln 1, DeichmannhausDr.-Ing. A. ν. Kreisler, Dr.-Ing. K. Schönwald,
Dr.-Ing. Th. Meyer and Dr. JF Fues,
Patent attorneys, Cologne 1, Deichmannhaus
Als Erfinder benannt:Named as inventor:
James D. Atwood,James D. Atwood,
Ronald H. WiIe, Gallipolis Ferry, W. Va.;Ronald H. WiIe, Gallipolis Ferry, W. Va .;
Paul C. Pearson, Newark, N. J. (V. St. A.)Paul C. Pearson, Newark, N.J. (V. St. A.)
Beanspruchte Priorität:Claimed priority:
V. St. ν. Amerika vom 3. Januar 1961 (80 046)V. St. ν. America January 3, 1961 (80 046)
Kohlenstoffatome enthalten, insbesondere Tributylphosphat. Gewöhnlich verwendet man die Phosphorverbindung in einer Menge von etwa 0,2 bis 1,0 Gewichtsprozent, bezogen auf das Gewicht des Polyolesters, der theoretisch gebildet werden kann. Bevorzugt werden 0,3 bis 0,6 Gewichtsprozent.Contain carbon atoms, especially tributyl phosphate. The phosphorus compound is usually used in an amount of about 0.2 to 1.0 percent by weight, based on the weight of the polyol ester, which can be formed theoretically. 0.3 to 0.6 percent by weight is preferred.
Die zur Herstellung der Polyolester verwendeten gesättigten Fettsäuren enthalten vorzugsweise gerade Ketten mit einer Länge von 5 bis 9 Kohlenstoffatomen, oder es sind Gemische solcher Säuren mit einer mittleren Kettenlänge von 5 bis 9 Kohlenstoffatomen. Wenn Gemische verwendet werden, können die einzelnen Säuren Kohlenstoffketten von 2 bis 18 Atomen enthalten. Bevorzugt werden geradkettige Säuren, jedoch können auch verzweigte Fettsäuren verwendet werden, besonders solche mit nicht mehr als 2 Kohlenstoffatomen in den Seitenketten. Bei Verwendung von Trimethylolpropan als Polyol werden gewöhnlich C6-C9-Säuren verwendet, wobei reine Heptansäure (= Önanthsäure, C7H14O2) bevorzugt wird.The saturated fatty acids used to produce the polyol esters preferably contain straight chains with a length of 5 to 9 carbon atoms, or they are mixtures of such acids with an average chain length of 5 to 9 carbon atoms. When mixtures are used, the individual acids can contain carbon chains of 2 to 18 atoms. Straight-chain acids are preferred, but branched fatty acids can also be used, especially those with no more than 2 carbon atoms in the side chains. When using trimethylolpropane as the polyol, C 6 -C 9 acids are usually used, with pure heptanoic acid (= enanthic acid, C 7 H 14 O 2 ) being preferred.
Als Polyole werden solche mit wenigstens zwei, vorzugsweise mit drei Methylolgruppen an einem quaternären Kohlenstoffatom verwendet. Zu den geeigneten Polyolen gehören Trimethylolpropan, Trimethyloläthan, Neopentylglykol, Pentaerythrit, 2-Butyl-2-äthyl-1,3-propandiol und 2,2,4-Trimethyl-l,3-pentandiol.The polyols used are those with at least two, preferably three, methylol groups on a quaternary Carbon atom used. Suitable polyols include trimethylolpropane, trimethylolethane, Neopentyl glycol, pentaerythritol, 2-butyl-2-ethyl-1,3-propanediol and 2,2,4-trimethyl-1,3-pentanediol.
609 667/427609 667/427
3 43 4
Die Polyolester werden im allgemeinen hergestellt, und 250° C bei 1 mm Hg sieden. Es hat den Anschein,The polyol esters are generally made and boil at 250 ° C. at 1 mm Hg. It looks like,
indem das Polyol mit einem geringen Überschuß der daß auch die schlechteren Ausbeuten der bekanntenby the polyol with a small excess of that also the poorer yields of the known
Fettsäure unter Entfernung des Wassers durch Ab- Verfahren durch die stabilisierende Wirkung der Re-Fatty acid with removal of the water by ab- process due to the stabilizing effect of the re-
destillieren, vorzugsweise in Gegenwart eines Mittels, aktionsprodukte _ des Phosphors verbessert werden,distill, preferably in the presence of an agent, action products _ of phosphorus are improved,
das mit Wasser ein azeotropes Gemisch bildet, z. B. 5 Es scheint ferner, daß gewöhnlich zunächst das ge-which forms an azeotropic mixture with water, e.g. B. 5 It also seems that usually first
einem flüchtigen Kohlenwasserstoff, umgesetzt wird. samte Polyol bei- der Veresterung in Gegenwart einesa volatile hydrocarbon. entire polyol - esterification in the presence of one
Bei Trimethylolpropan können beispielsweise 3,3 bis Säureüberschusses in den Ester übergeführt wird, derIn the case of trimethylolpropane, for example, 3.3 to excess acid can be converted into the ester, which
3,6 Mol Fettsäure je Mol Trimethylolpropan verwendet jedoch zum Teil während der Veresterung und desHowever, 3.6 moles of fatty acid per mole of trimethylolpropane used in part during the esterification and the
werden. Die mit Wasser ein azeotropes Gemisch bil- anschließenden Erhitzens unter den angewendetenwill. The subsequent heating under the applied water forms an azeotropic mixture
dende Verbindung, z. B. Xylol, kann in einer Menge io scharfen Bedingungen wieder abgebaut wird. Die An-the connection, e.g. B. xylene, can be broken down again in a lot in harsh conditions. The arrival
von 2 bis etwa 12 Gewichtsteilen je 100 Teile Reak- Wesenheit einer der erfindurigsgemäßen Phosphor-from 2 to about 12 parts by weight per 100 parts of Reak essence of one of the inventive phosphorus
tionsgemisch zugesetzt werden. Vorzugsweise wird zu verbindungen oder deren Reaktionsprodukte scheinttion mixture are added. Preferably it appears to compounds or their reaction products
diesem Zweck ein zwischen 80 und 15O0C siedender den Abbau zu verringern und ermöglicht auf diesea boiling to reduce this, between 80 and 15O 0 C degradation and thus allows
Kohlenwasserstoff verwendet. Neben Xylol werden Weise eine Ausbeutesteigerung.Used hydrocarbon. In addition to xylene, there will be an increase in yield.
Toluol, Cyclohexan, Benzol und Gemische von ali- 15 Die gemäß der Erfindung hergestellten Ester könnenToluene, cyclohexane, benzene and mixtures of ali- 15 The esters prepared according to the invention can
phatischen Kohlenwasserstoffen, wie geeigneten Erd- mit Zusatzstoffen gemischt werden, von denen bekanntPhatic hydrocarbons, such as suitable soil, are mixed with additives, of which are known
ölfraktionen, bevorzugt. ist, daß sie die thermische Stabilität, Oxydätions-oil fractions, preferred. is that it enhances thermal stability, oxidation
Die Veresterungsreaktion wird gewöhnlich bei beständigkeit und Schmierfähigkeit verbessern, Me-The esterification reaction will usually improve durability and lubricity, m
Normaldruck unter Rückfluß bei einer Temperatur talle deaktivieren und die Bleikorrosion verhindern,Deactivate normal pressure under reflux at a temperature and prevent lead corrosion,
zwischen etwa 140 und 350° C durchgeführt. Das 20 Besonders vorteilhaft als oxydationsverhütendecarried out between about 140 and 350 ° C. The 20 particularly advantageous as an anti-oxidant
Wasser wird in dem Maße, in dem es gebildet wird, Mittel ist ein Zusatz von 0,5 bis 3 GewichtsprozentWater is added to the extent to which it is formed, an additive of 0.5 to 3 percent by weight
zusammen mit dem Schleppmittel abdestilliert. Die eines sekundären Amins, wie Phenyl-a-naphthylamin,distilled off together with the entrainer. That of a secondary amine, such as phenyl-a-naphthylamine,
Reaktion wird so lange durchgeführt, bis der Hydro- und 0,5 bis 3 Gewichtsprozent einer Phenosilazin-The reaction is carried out until the hydro and 0.5 to 3 percent by weight of a phenosilazine
xylgehalt des Reaktionsgemisches nicht mehr als verbindung, ζ. B. N-Äthylphenodiphenylsilazin.xyl content of the reaction mixture no more than compound, ζ. B. N-ethylphenodiphenylsilazine.
0,1 Gewichtsprozent beträgt. Dies erfordert gewöhn- 250.1 weight percent. This requires habitual 25
lieh 4 bis 20 Stunden. Beispiel!.borrowed 4 to 20 hours. Example!.
Nach Beendigung der Veresterungsreaktion kannAfter completion of the esterification reaction can
der Druck auf 5 bis 10 mm Hg gesenkt werden, wobei 250 Gewichtsteile Trimethylolpropan, 800 Gewichts-the pressure can be reduced to 5 to 10 mm Hg, with 250 parts by weight of trimethylolpropane, 800 parts by weight
das Endprodukt bis auf eine Temperatur von 240° C teile Heptansäure und 4 Gewichtsteile Tributylphos-the end product up to a temperature of 240 ° C parts heptanoic acid and 4 parts by weight tributylphosphorus
erhitzt wird, um den als Schleppmittel für Wasser 30 phat wurden in einen Destillierkolben gegeben, deris heated to the as an entrainer for water 30 phat were placed in a still, the
verwendeten Kohlenwasserstoff und die überschüssige mit einer 5-Böden-Kolonne versehen war, und unterused hydrocarbon and the excess was provided with a 5-tray column, and below
Säure zu entfernen. Der Säuregehalt ist auf einen Stickstoff erhitzt, bis Rückfluß einsetzte. Nach ZusatzRemove acid. The acidity is heated to nitrogen until reflux began. After addition
Wert von nicht mehr als 2 Gewichtsprozent zu senken, von 120 Gewichtsteilen einer Erdölfraktion vomLower the value of not more than 2 percent by weight, of 120 parts by weight of a petroleum fraction dated
um eine Emulsionsbildung während des anschließen- Siedebereich 115 bis 130° C wurde etwa 4 StundenAn emulsion formation during the subsequent boiling range 115 to 130 ° C was about 4 hours
den Auswaschens zu vermeiden. 35 erhitzt, bis das gesamte Wasser entfernt war. Dannto avoid washing out. 35 heated until all the water was removed. then
Nach dem Erhitzen kann der Ester mit Natrium- wurde noch 1 Stunde bei einer Kolbentemperatur von hydroxyd- und dann mit Natriumchloridlösung ge- 280° C und geringem Überdruck (0,21 bis 0,42 kg/cma) waschen und abschließend zur Entfernung des Wassers weiter erhitzt. Schleppmittel und überschüssige Säure nochmals im Vakuum erhitzt werden. Es können auch wurden dann bei 240°C/5 bis 10 mm Hg abgetriebeü andere Methoden zur Senkung des Säuregehalts an- 40 und das Gemisch mit 3%iger wäßriger Natriumgewendet werden, z. B. Waschen mit einer Natrium- carbonatlösung gewaschen. Die Ölschicht wurde abcarbonatlösung, Rühren mit einer wäßrigen Auf- getrennt, bei 100 bis 105° C/10mm Hg völlig entwässert, schlämmung eines alkalischen Stoffs von geringer mit Kohle behandelt und schließlich filtriert. Die Aus-Löslichkeit, z. B. Calciumoxyd, oder Behandlung mit beute an Trimethylolpropan—Triheptylester betrug einem Ionenaustauscherharz. 45 96,5 %> bezogen auf Trimethylolpropan.After heating, the ester can be washed with sodium for 1 hour at a flask temperature of hydroxide and then with sodium chloride solution 280 ° C and a slight excess pressure (0.21 to 0.42 kg / cm a ) and finally to remove the Water further heated. Entrainer and excess acid are reheated in vacuo. It can also were then / 5 to 10 mm Hg abgetriebeü other methods for reducing the acidity present at 240 ° C 40, and the mixture extracted with 3% strength aqueous sodium he be turned, z. B. Wash washed with a sodium carbonate solution. The oil layer was separated from carbonate solution, stirring with an aqueous solution, completely dehydrated at 100 to 105 ° C./10 mm Hg, slurry of an alkaline substance of less than carbon was treated and finally filtered. The off solubility, e.g. B. calcium oxide, or treatment with loot of trimethylolpropane triheptyl ester was an ion exchange resin. 45 96.5%> based on trimethylolpropane.
Das entwässerte Produkt kann dann mit Entfärber- In einem Vergleichsversuch, der auf die gleicheThe dehydrated product can then be used in a comparative experiment based on the same
kohle behandelt und abschließend durch Diatomeen- Weise durchgeführt wurde, wurde das Tributylphos-treated carbon and finally carried out by diatoms, the tributylphosphorus was
erde filtriert werden, phat weggelassen. Die Ausbeute in diesem Fall betrugearth filtered, phat omitted. The yield in this case was
Die als Katalysator verwendete Phosphorverbindung nur 87 %> bezogen auf Trimethylpropan.The phosphorus compound used as a catalyst only 87%> based on trimethylpropane.
muß wenigstens während eines Teils der Veresterungs- 50 Proben der in den beiden Versuchen erhaltenenmust during at least part of the esterification 50 samples obtained in the two experiments
<■ reaktion, jedoch vorzugsweise während der ganzen Ester wurden jeweils mit 1 Gewichtsprozent Phenyl-<■ reaction, but preferably during the entire ester, were each with 1 percent by weight of phenyl
Reaktionsdauer als solche vorliegen. Einem fertigen a-naphthylamin und 1 Gewichtsprozent N-Äthyl-Reaction time as such. A finished a-naphthylamine and 1 percent by weight of N-ethyl
Ester zugesetztes Trialkylphosphat erhöht nicht dessen phenodiphenylsilazin gemischt. Die Mischungen wur-Trialkyl phosphate added to ester does not increase its phenodiphenylsilazine mixed. The mixtures were
Oxydationsbeständigkeit. Triarylphosphate, wie Tri- den in einem mit Thermostat und HeizvorrichtungResistance to oxidation. Triaryl phosphates, such as tridene in one with thermostat and heating device
kresylphosphat, sind weder als Zusatz zum fertigen 55 versehenen Aluminiumblock mit sechs Löchern aufcresyl phosphate, are not available as an additive to the finished aluminum block with six holes
Ester noch als Veresterungskatalysatoren brauchbar. ihre Oxydationsbeständigkeit geprüft. Die PrüfungenEsters can still be used as esterification catalysts. their resistance to oxidation checked. The exams
Es wird angenommen, daß die Phosphorverbindung wurden nach der Vorschrift »Revised MÜ-L-9236A«It is assumed that the phosphorus compounds were according to the specification "Revised MÜ-L-9236A"
nicht selbst als stabilisierender Stoff wirksam ist, durchgeführt, wobei 961 Luft stündlich durch die beiis not itself effective as a stabilizing substance, carried out with 961 air hourly through the at
sondern daß sie bei der Veresterung unter Bildung 218° C gehaltenen 250-cm3-Proben geleitet wurden. Der but rather that they were passed 250 cm 3 samples held at 218 ° C. during the esterification process. Of the
eines Produkts von stabilisierender Wirkung reagiert. 60 Gewichtsverlust an flüchtigen Stoffen, die währendof a product with a stabilizing effect. 60 volatile weight loss during
Es wurde festgestellt, daß der fertige Ester selbst nach der Prüfung aus den Proben abgetrieben wurden,It was found that the finished ester was stripped from the samples even after testing,
der Destillation und sonstigen Reinigungsmaßnahmen wurde in Abständen von 5 Stunden durch das gleiche etwa die Hälfte des ursprünglich im Reaktionsgemisch Volumen einer frischen Probe ersetzt. Die Prüfungenthe distillation and other purification measures were carried out at intervals of 5 hours by the same about half of the volume of a fresh sample originally in the reaction mixture is replaced. The exams
vorhandenen Phosphors enthält. Dieser Phosphor ist wurden fortgesetzt, bis ein scharfer Anstieg vonContains existing phosphorus. This phosphorus has continued until a sharp rise in
offensichtlich Bestandteil von Verbindungen, deren 65 Viskosität, Azidität und Gewichtsverlust den Abbauobviously constituent of compounds whose viscosity, acidity and weight loss break down
Siedepunkt bei 1 mm Hg bis zu etwa 20°C über dem der geprüften Probe erkennen ließ. Die erhaltenenBoiling point at 1 mm Hg up to about 20 ° C above that of the sample tested. The received
Siedepunkt des Polyolesters liegt, die also z. B. im Ergebnisse sind in den .folgenden Tabellen aufgeführt;Boiling point of the polyol ester, which is z. B. in the results are listed in the following tables;
Falle von Trimethylolpropanheptanoat zwischen 230 in denen (a) der gemäß der Erfindung hergestellteCase of trimethylol propane heptanoate between 230 in which (a) that prepared according to the invention
Ester und (b) der im Vergleichsversuch hergestellte Ester ist.Ester and (b) is the ester prepared in the comparative experiment.
25Time (p
25th
30hours)
30th
17,3931.80
17.39
0,040.02
0.04
0,232.49
0.23
15Time
15th
20t (hour
20th
25en)
25th
15,9015.78
15.90
9,610.6
9.6
6,215.6
6.2
9,221.2
9.2
8,619.7
8.6
(a)* (b)
(a)
8,511.0
8.5
(a)(b)
(a)
(a)(b)
(a)
Azidität der flüchtigen Stoffe insgesamt (mg KOH/g)Total volatile acidity (mg KOH / g)
(b) 54,2(b) 54.2
(a) 9,10(a) 9.10
335 Gewichtsteile Trimethylolpropan, 1072,5 Gewichtsteile Heptansäure und 7,0 Gewichtsteile Phosphorsäure wurden auf 24O0C erhitzt und 22 Stunden bei dieser Temperatur gehalten. Während dieser Zeit335 parts by weight of trimethylolpropane, 1072.5 parts by weight of heptanoic acid and 7.0 parts by weight of phosphoric acid was heated to 24O 0 C and held for 22 hours at this temperature. During this time
ίο wurde das Wasser unter Verwendung von Xylol als Schleppmittel abdestilliert. Dann wurden bei einer Temperatur von 230° C und einem Druck von 1 mm Hg flüchtige Stoffe entfernt, abgekühlt und fünfmal mit l°/oigeva. wäßrigem Natriumcarbonat und zweimal mit Wasser gewaschen. Schließlich wurde das Produkt bei 100° C und einem Druck von lmm Hg von Wasser befreit, mit Kohle behandelt und filtriert.ίο the water was distilled off using xylene as an entrainer. Then, at a temperature of 230 ° C and a pressure of 1 mm Hg volatiles were removed, cooled and washed five times with l ° / o igeva. aqueous sodium carbonate and washed twice with water. Finally, the product was freed from water at 100 ° C. and a pressure of 1 mm Hg, treated with charcoal and filtered.
Der auf die beschriebene Weise erhaltene EsterThe ester obtained in the manner described
wurde mit 1 Gewichtsprozent-Phenyl-a-naphthylaminwas with 1 weight percent phenyl-a-naphthylamine
ao und 1 Gewichtsprozent N-Äthylphenodiphenylsilazin gemischt und auf die oben geschriebene Weise auf Oxydationsbeständigkeit geprüft. Die Ergebnisse sind nachstehend angegeben:ao and 1 percent by weight of N-ethylphenodiphenylsilazine and mixed in the manner described above Oxidation resistance tested. The results are given below:
Testtest
Viskosität (cSt bei 37,8°C) Viscosity (cSt at 37.8 ° C)
Azidität (mg KOH/g) Acidity (mg KOH / g)
Ergänzung von flüchtigen Stoffen (g) Supplement of volatile substances (g)
Azidität der flüchtigen Stoffe insgesamt (mg KOH/g).Total volatile acidity (mg KOH / g).
Claims (5)
0,43
8
5,819.51
0.43
8th
5.8
USA.-Patentschrift Nr. 2 798 083;
französische Patentschriften Nr. 1251027,1251028.Considered publications:
U.S. Patent No. 2,798,083;
French patent specification No. 1251027,1251028.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US80046A US3215720A (en) | 1961-01-03 | 1961-01-03 | Methods of producing phosphorus esters of polyol alkanoic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1225161B true DE1225161B (en) | 1966-09-22 |
Family
ID=46968431
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEC25865A Pending DE1225161B (en) | 1961-01-03 | 1961-12-29 | Process for the production of polyol fatty acid esters serving as high-performance lubricants |
Country Status (3)
Country | Link |
---|---|
US (1) | US3215720A (en) |
DE (1) | DE1225161B (en) |
GB (1) | GB988051A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3325567A (en) * | 1963-05-17 | 1967-06-13 | Lubrizol Corp | Phosphorus esters and process |
US3800002A (en) * | 1970-03-20 | 1974-03-26 | Japan Synthetic Rubber Co Ltd | Process for preventing the polymerization of conjugated dienes |
US4229310A (en) * | 1978-03-16 | 1980-10-21 | Mobil Oil Corporation | Lubricant compositions |
JPS5845293A (en) * | 1981-09-10 | 1983-03-16 | Idemitsu Kosan Co Ltd | Fluid composition for shock absorber |
US4857215A (en) * | 1986-03-25 | 1989-08-15 | Wong John L | Semi-fluid lubricant for extreme climates |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2798083A (en) * | 1954-02-03 | 1957-07-02 | Eastman Kodak Co | Synthetic ester lubricants |
FR1251027A (en) * | 1959-03-12 | 1961-01-13 | Heyden Newport Chemical Corp | Lubricating esters |
FR1251028A (en) * | 1960-03-11 | 1961-01-13 | Heyden Newport Chemical Corp | Lubricating compositions |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2177983A (en) * | 1935-12-30 | 1939-10-31 | Benjamin R Harris | Phosphate esters |
US2177984A (en) * | 1937-02-11 | 1939-10-31 | Benjamin R Harris | Phosphoric acid esters and method of producing them |
US2492955A (en) * | 1946-08-31 | 1950-01-03 | Shell Dev | Polyoxyalkylene compounds |
US2643261A (en) * | 1948-10-01 | 1953-06-23 | Standard Oil Dev Co | Phosphorus-containing lubricating oil additives |
US3036005A (en) * | 1959-04-23 | 1962-05-22 | Celanese Corp | High temperature lubricant composition |
-
1961
- 1961-01-03 US US80046A patent/US3215720A/en not_active Expired - Lifetime
- 1961-12-29 DE DEC25865A patent/DE1225161B/en active Pending
-
1962
- 1962-01-03 GB GB228/62A patent/GB988051A/en not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2798083A (en) * | 1954-02-03 | 1957-07-02 | Eastman Kodak Co | Synthetic ester lubricants |
FR1251027A (en) * | 1959-03-12 | 1961-01-13 | Heyden Newport Chemical Corp | Lubricating esters |
FR1251028A (en) * | 1960-03-11 | 1961-01-13 | Heyden Newport Chemical Corp | Lubricating compositions |
Also Published As
Publication number | Publication date |
---|---|
US3215720A (en) | 1965-11-02 |
GB988051A (en) | 1965-04-07 |
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