NL8601965A - Werkwijze voor de bereiding van ep-toevoegsels. - Google Patents
Werkwijze voor de bereiding van ep-toevoegsels. Download PDFInfo
- Publication number
- NL8601965A NL8601965A NL8601965A NL8601965A NL8601965A NL 8601965 A NL8601965 A NL 8601965A NL 8601965 A NL8601965 A NL 8601965A NL 8601965 A NL8601965 A NL 8601965A NL 8601965 A NL8601965 A NL 8601965A
- Authority
- NL
- Netherlands
- Prior art keywords
- reaction
- product
- process according
- parts
- sulfur
- Prior art date
Links
- 239000000654 additive Substances 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 60
- 239000011593 sulfur Substances 0.000 claims description 52
- 229910052717 sulfur Inorganic materials 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 49
- 239000000047 product Substances 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 24
- 239000012071 phase Substances 0.000 claims description 21
- 239000005069 Extreme pressure additive Substances 0.000 claims description 20
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 15
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000008096 xylene Substances 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002798 polar solvent Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000011877 solvent mixture Substances 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical class CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 claims description 7
- 230000001050 lubricating effect Effects 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 238000005555 metalworking Methods 0.000 claims description 6
- 150000002896 organic halogen compounds Chemical class 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000005077 polysulfide Substances 0.000 claims description 5
- 229920001021 polysulfide Polymers 0.000 claims description 5
- 150000008117 polysulfides Polymers 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000010720 hydraulic oil Substances 0.000 claims description 4
- 239000010687 lubricating oil Substances 0.000 claims description 4
- 239000002826 coolant Substances 0.000 claims description 3
- 239000005068 cooling lubricant Substances 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 claims description 2
- ISXDOPCKEDRLAY-UHFFFAOYSA-N 1-chlorotridecylbenzene Chemical compound CCCCCCCCCCCCC(Cl)C1=CC=CC=C1 ISXDOPCKEDRLAY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000007265 chloromethylation reaction Methods 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000118 dimethyl group Chemical class [H]C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims description 2
- 238000005352 clarification Methods 0.000 claims 3
- VQRBXYBBGHOGFT-UHFFFAOYSA-N 1-(chloromethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CCl VQRBXYBBGHOGFT-UHFFFAOYSA-N 0.000 claims 1
- LZBOHNCMCCSTJX-UHFFFAOYSA-N 1-(chloromethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CCl)=C1 LZBOHNCMCCSTJX-UHFFFAOYSA-N 0.000 claims 1
- DUBCVXSYZVTCOC-UHFFFAOYSA-N 1-(chloromethyl)-4-ethylbenzene Chemical compound CCC1=CC=C(CCl)C=C1 DUBCVXSYZVTCOC-UHFFFAOYSA-N 0.000 claims 1
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 claims 1
- 229910020275 Na2Sx Inorganic materials 0.000 claims 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims 1
- 229940073608 benzyl chloride Drugs 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- 239000013049 sediment Substances 0.000 claims 1
- 238000007086 side reaction Methods 0.000 claims 1
- 230000007797 corrosion Effects 0.000 description 11
- 238000005260 corrosion Methods 0.000 description 11
- 125000004434 sulfur atom Chemical group 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 150000008116 organic polysulfides Chemical class 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000003466 welding Methods 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MZMVVHAHSRJOEO-UHFFFAOYSA-N 1-chloropropylbenzene Chemical compound CCC(Cl)C1=CC=CC=C1 MZMVVHAHSRJOEO-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012208 gear oil Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- ZDEZSEZTNVSIKC-UHFFFAOYSA-N C=1(C(=CC=CC1)C)C.O.C(C)O.[S-2].[Na+].[Na+] Chemical group C=1(C(=CC=CC1)C)C.O.C(C)O.[S-2].[Na+].[Na+] ZDEZSEZTNVSIKC-UHFFFAOYSA-N 0.000 description 1
- 101100369802 Caenorhabditis elegans tim-1 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/02—Sulfurised compounds
- C10M135/04—Hydrocarbons
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8610896 | 1986-07-28 | ||
| FR8610896A FR2602785B1 (fr) | 1986-07-28 | 1986-07-28 | Procede de preparation d'additifs ep (extreme pression) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8601965A true NL8601965A (nl) | 1988-02-16 |
Family
ID=9337786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8601965A NL8601965A (nl) | 1986-07-28 | 1986-07-31 | Werkwijze voor de bereiding van ep-toevoegsels. |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE905181A (enrdf_load_stackoverflow) |
| CH (1) | CH675121A5 (enrdf_load_stackoverflow) |
| FR (1) | FR2602785B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2193958B (enrdf_load_stackoverflow) |
| NL (1) | NL8601965A (enrdf_load_stackoverflow) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2185008A (en) * | 1937-12-30 | 1939-12-26 | Hooker Electrochemical Co | Di-alkylbenzenoid sulphides and process for their production |
| GB548150A (en) * | 1941-03-25 | 1942-09-28 | Elliott Alfred Evans | Improvements in or relating to the production of alkyl, aralkyl and arylacyl organic compounds containing divalent sulphur |
| GB706566A (en) * | 1950-06-09 | 1954-03-31 | Bataafsche Petroleum | Improvements in or relating to lubricant and hydraulic fluids compositions |
| US2726236A (en) * | 1953-02-02 | 1955-12-06 | Shell Dev | Production of sulfur-containing high molecular weight hydrocarbon derivatives |
| BE541222A (enrdf_load_stackoverflow) * | 1954-09-13 | |||
| IT1003925B (it) * | 1974-03-27 | 1976-06-10 | Chimasa Chimica Organica Spa | Procedimento per la preparazione di solfuri organici |
-
1986
- 1986-07-18 CH CH288686A patent/CH675121A5/de not_active IP Right Cessation
- 1986-07-28 FR FR8610896A patent/FR2602785B1/fr not_active Expired - Lifetime
- 1986-07-28 BE BE1/011528A patent/BE905181A/fr not_active IP Right Cessation
- 1986-07-31 NL NL8601965A patent/NL8601965A/nl not_active Application Discontinuation
- 1986-08-14 GB GB8619835A patent/GB2193958B/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2193958B (en) | 1991-02-06 |
| GB8619835D0 (en) | 1986-09-24 |
| GB2193958A (en) | 1988-02-24 |
| FR2602785A1 (fr) | 1988-02-19 |
| BE905181A (fr) | 1987-01-28 |
| CH675121A5 (enrdf_load_stackoverflow) | 1990-08-31 |
| FR2602785B1 (fr) | 1990-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |