CA1187508A - Additifs sulfures a base d'huile adipeuses - Google Patents

Additifs sulfures a base d'huile adipeuses

Info

Publication number: CA1187508A
Authority: CA; Canada
Prior art keywords: mole; acids; triglyceride; sulfurized; additive composition
Prior art date: 1982-09-23
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

Application number

CA000412035A

Other languages

English (en)

Inventor

Karl P. Kammann, Jr.

Marvin J. Den Herder

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Vibrantz Corp

Original Assignee

Ferro Corp

Priority date (The priority date 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 date listed.)

1982-09-23

Filing date

1982-09-23

Publication date

1985-05-21

1982-09-23 Application filed by Ferro Corp filed Critical Ferro Corp

1982-09-23 Priority to CA000412035A priority Critical patent/CA1187508A/fr

1985-05-21 Application granted granted Critical

1985-05-21 Publication of CA1187508A publication Critical patent/CA1187508A/fr

Status Expired legal-status Critical Current

Links

239000000654 additive Substances 0.000 title claims abstract description 58
239000010685 fatty oil Substances 0.000 title abstract description 9
239000000203 mixture Substances 0.000 claims abstract description 89
230000000996 additive effect Effects 0.000 claims abstract description 40
150000003626 triacylglycerols Chemical class 0.000 claims abstract description 25
239000000446 fuel Substances 0.000 claims abstract description 24
239000003921 oil Substances 0.000 claims abstract description 24
239000002253 acid Substances 0.000 claims description 69
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 46
150000007513 acids Chemical class 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 29
239000000047 product Substances 0.000 claims description 29
238000000034 method Methods 0.000 claims description 27
125000001931 aliphatic group Chemical group 0.000 claims description 24
238000005809 transesterification reaction Methods 0.000 claims description 19
239000003054 catalyst Substances 0.000 claims description 18
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
235000014113 dietary fatty acids Nutrition 0.000 claims description 16
239000000194 fatty acid Substances 0.000 claims description 16
229930195729 fatty acid Natural products 0.000 claims description 16
150000004665 fatty acids Chemical class 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
239000011593 sulfur Substances 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
238000005987 sulfurization reaction Methods 0.000 claims description 11
-1 aliphatic primary alcohols Chemical class 0.000 claims description 10
230000032050 esterification Effects 0.000 claims description 9
238000005886 esterification reaction Methods 0.000 claims description 9
238000010438 heat treatment Methods 0.000 claims description 9
230000007928 solubilization Effects 0.000 claims description 9
238000005063 solubilization Methods 0.000 claims description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
229940098779 methanesulfonic acid Drugs 0.000 claims description 8
235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
150000001336 alkenes Chemical class 0.000 claims description 7
239000010687 lubricating oil Substances 0.000 claims description 7
239000007795 chemical reaction product Substances 0.000 claims description 6
238000002485 combustion reaction Methods 0.000 claims description 5
235000021122 unsaturated fatty acids Nutrition 0.000 claims description 5
150000004670 unsaturated fatty acids Chemical class 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
235000021281 monounsaturated fatty acids Nutrition 0.000 claims description 4
239000002199 base oil Substances 0.000 claims description 3
YWFUVTMPYOLBDB-UHFFFAOYSA-M butyl(chloro)tin;dihydrate Chemical compound O.O.CCCC[Sn]Cl YWFUVTMPYOLBDB-UHFFFAOYSA-M 0.000 claims description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 claims description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
235000011152 sodium sulphate Nutrition 0.000 claims description 2
239000004246 zinc acetate Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
239000002283 diesel fuel Substances 0.000 claims 1
125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
125000005457 triglyceride group Chemical group 0.000 claims 1
239000000314 lubricant Substances 0.000 abstract description 13
239000003879 lubricant additive Substances 0.000 abstract description 5
238000005461 lubrication Methods 0.000 abstract description 3
235000019198 oils Nutrition 0.000 description 21
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
239000000306 component Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 8
239000010699 lard oil Substances 0.000 description 8
239000002480 mineral oil Substances 0.000 description 8
239000003784 tall oil Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
229910001651 emery Inorganic materials 0.000 description 6
235000010446 mineral oil Nutrition 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 5
230000008569 process Effects 0.000 description 5
235000013162 Cocos nucifera Nutrition 0.000 description 4
244000060011 Cocos nucifera Species 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
239000010705 motor oil Substances 0.000 description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
230000009467 reduction Effects 0.000 description 4
230000003381 solubilizing effect Effects 0.000 description 4
229910014033 C-OH Inorganic materials 0.000 description 3
229910014570 C—OH Inorganic materials 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
241000196324 Embryophyta Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
239000004440 Isodecyl alcohol Substances 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000005233 alkylalcohol group Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003138 primary alcohols Chemical group 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
239000002966 varnish Substances 0.000 description 2
238000010792 warming Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
241000415246 Callisia navicularis Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
235000019482 Palm oil Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000010692 aromatic oil Substances 0.000 description 1
230000000712 assembly Effects 0.000 description 1
238000000429 assembly Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
229940073769 methyl oleate Drugs 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
238000010248 power generation Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000010689 synthetic lubricating oil Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000010913 used oil Substances 0.000 description 1

Landscapes

Lubricants (AREA)
Liquid Carbonaceous Fuels (AREA)

CA000412035A 1982-09-23 1982-09-23 Additifs sulfures a base d'huile adipeuses Expired CA1187508A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000412035A CA1187508A (fr)	1982-09-23	1982-09-23	Additifs sulfures a base d'huile adipeuses

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000412035A CA1187508A (fr)	1982-09-23	1982-09-23	Additifs sulfures a base d'huile adipeuses

Publications (1)

Publication Number	Publication Date
CA1187508A true CA1187508A (fr)	1985-05-21

Family

ID=4123650

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000412035A Expired CA1187508A (fr)	1982-09-23	1982-09-23	Additifs sulfures a base d'huile adipeuses

Country Status (1)

Country	Link
CA (1)	CA1187508A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113913229A (zh) *	2021-10-18	2022-01-11	武汉工程大学	一种基于黑水虻油脂的环境友好型抗磨添加剂及其制备方法
CN114058431A (zh) *	2021-11-01	2022-02-18	梧州市澳拿科技有限公司	一种环保非活性硫化猪油及其制备方法

1982
- 1982-09-23 CA CA000412035A patent/CA1187508A/fr not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113913229A (zh) *	2021-10-18	2022-01-11	武汉工程大学	一种基于黑水虻油脂的环境友好型抗磨添加剂及其制备方法
CN114058431A (zh) *	2021-11-01	2022-02-18	梧州市澳拿科技有限公司	一种环保非活性硫化猪油及其制备方法
CN114058431B (zh) *	2021-11-01	2023-02-24	梧州市澳拿科技有限公司	一种环保非活性硫化猪油及其制备方法

Legal Events

Date	Code	Title	Description
2002-05-22	MKEC	Expiry (correction)
2002-09-23	MKEX	Expiry

Publication	Publication Date	Title
US4380499A (en)	1983-04-19	Sulfurized fatty oil additives and their use in a lubricating oil and a fuel
DE69831887T2 (de)	2006-07-27	Aus Pflanzenölen stammende Ester zur Verwendung als Kraftstoffezusätze
CA2540435C (fr)	2012-11-13	Esters d'acides gras derives de tallol pour utilisation dans des lubrifiants et des combustibles
DE3887693T2 (de)	1994-05-11	Gemische von partialestern von fettsäuren mit mehrwertigen alkoholen und sulfurisierten zusammensetzungen und ihre verwendung als schmiermittelzusätze.
DE3876438T2 (de)	1993-06-09	Sulfurizierte zusammensetzungen und diese enthaltende zusatzkonzentrate und schmieroele.
CN1085243C (zh)	2002-05-22	可生物降解的润滑基础油,含该油的组合物及其用途
CA1111017A (fr)	1981-10-20	Composes pouvant remplacer l'huile de blanc de baleine
RU2449005C2 (ru)	2012-04-27	Смазывающие композиции для углеводородной смеси и полученные продукты
CA2141102A1 (fr)	1995-07-29	Huiles de type triglycerides epaissies avec des estolides de triglycerides a groupes hydroxyles
US4152278A (en)	1979-05-01	Wax esters of vegetable oil fatty acids useful as lubricants
US4921624A (en)	1990-05-01	Modified fatty amides and sulfurized fatty oils as lubricant additives
EP0193870B1 (fr)	1990-06-27	Lubrifiant pour le laminage à froid et procédé de fabrication de tôles en acier
US4380498A (en)	1983-04-19	Sulfurized, transesterified oil additives and their use in a lubricating oil and a fuel
US4664826A (en)	1987-05-12	Metal salt esters of hydrocarbyl substituted succinic acid or anhydride and thio alkanols
US20050112267A1 (en)	2005-05-26	Lubricant base from palm oil and its by-products
US2563609A (en)	1951-08-07	Lubricating oil additives
DE69017002T2 (de)	1995-06-22	Methode zur herstellung von monothiophosphorsäure durch umsetzung eines phosphites mit schwefel in gegenwart eines amids.
US4684473A (en)	1987-08-04	Lubricant oil composition with improved friction reducing properties
CA1187508A (fr)	1985-05-21	Additifs sulfures a base d'huile adipeuses
JP2552092B2 (ja)	1996-11-06	燐含有金属塩／オレフィン組成物と活性硫黄との反応生成物
US4485044A (en)	1984-11-27	Sulfurized esters of polycarboxylic acids
EP0102425B1 (fr)	1986-04-09	Additif pour huiles à base de triglycérides et méthode pour préparer cet additif
CN113056545B (zh)	2023-04-04	润滑剂组合物
US4589993A (en)	1986-05-20	Power transmission shift fluids containing two-component friction modifier additive
US2852540A (en)	1958-09-16	Oil soluble alkali and alkaline earth metal salts of p-acylamino phenols