EP3328978A1 - Composition for solubilization of organic residues - Google Patents
Composition for solubilization of organic residuesInfo
- Publication number
- EP3328978A1 EP3328978A1 EP16750704.5A EP16750704A EP3328978A1 EP 3328978 A1 EP3328978 A1 EP 3328978A1 EP 16750704 A EP16750704 A EP 16750704A EP 3328978 A1 EP3328978 A1 EP 3328978A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fatty acid
- esters
- acid esters
- composition
- weight
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 144
- 230000007928 solubilization Effects 0.000 title claims abstract description 11
- 238000005063 solubilization Methods 0.000 title claims abstract description 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 103
- 239000000194 fatty acid Substances 0.000 claims abstract description 103
- 229930195729 fatty acid Natural products 0.000 claims abstract description 103
- -1 fatty acid esters Chemical class 0.000 claims abstract description 90
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 150000004665 fatty acids Chemical class 0.000 claims description 28
- 239000003240 coconut oil Substances 0.000 claims description 21
- 235000019864 coconut oil Nutrition 0.000 claims description 21
- 239000012188 paraffin wax Substances 0.000 claims description 19
- 150000004702 methyl esters Chemical class 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 230000003381 solubilizing effect Effects 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 2
- 239000003209 petroleum derivative Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000002888 oleic acid derivatives Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 description 18
- 239000001993 wax Substances 0.000 description 17
- 238000004090 dissolution Methods 0.000 description 12
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 11
- 235000019484 Rapeseed oil Nutrition 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000005642 Oleic acid Substances 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229960002446 octanoic acid Drugs 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 235000019809 paraffin wax Nutrition 0.000 description 4
- 235000019271 petrolatum Nutrition 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000005643 Pelargonic acid Substances 0.000 description 3
- 239000010426 asphalt Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940071160 cocoate Drugs 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003346 palm kernel oil Substances 0.000 description 3
- 235000019865 palm kernel oil Nutrition 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical class CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002194 fatty esters Chemical class 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 229940073769 methyl oleate Drugs 0.000 description 2
- AOHAPDDBNAPPIN-UHFFFAOYSA-N myristicinic acid Natural products COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 2
- 150000002889 oleic acids Chemical class 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 description 1
- 235000021322 Vaccenic acid Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000001954 decanoic acid esters Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004200 deflagration Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- FIENEGBWDWHXGG-YPKPFQOOSA-N hexyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCCCC FIENEGBWDWHXGG-YPKPFQOOSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/266—Esters or carbonates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/04—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction
- C10G1/042—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction by the use of hydrogen-donor solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/667—Neutral esters, e.g. sorbitan esters
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/032—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/107—Atmospheric residues having a boiling point of at least about 538 °C
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1077—Vacuum residues
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1081—Alkanes
- C10G2300/1085—Solid paraffins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/80—Additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/16—Residues
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
- C11D2111/20—Industrial or commercial equipment, e.g. reactors, tubes or engines
Definitions
- the present invention relates to a composition that can be used to dissolve or disperse organic residues from crude oil including paraffin waxes and asphaltenes. It also relates to the uses of such a composition, as well as formulations containing such a composition in combination with other excipients.
- paraffin deposits or similar products can accumulate in the production and storage devices, thus limiting performance.
- bitumen when using petroleum fractionation products, particularly in the field of road coatings, it may be desirable to thin the bitumen to facilitate mixing with the mixes and / or spreading.
- EP 1012211 discloses detergents based on fatty acid lower alkyl esters having from 6 to 22 carbon atoms, mixed with solvents such as hydrocarbons or DMSO. It remains desirable to have compositions having good solvent properties or dispersing raw materials from the fractionation of heavy oils, but derived from renewable raw material and do not have such harmful effects.
- compositions which are not easily flammable to be able to transport them without special precautions and to use them under temperature conditions compatible with petroleum installations for example.
- compositions also have a satisfactory fluidity.
- the subject of the present invention is a composition for solubilizing organic residues of fossil material comprising a mixture of fatty acid esters of formula:
- R1 represents a C5 to C23, in particular C5 to C21, and especially C5 to C19 carbon chain, linear or branched, optionally containing one or more unsaturations,
- R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations
- composition comprising:
- the content of C8 to C14 saturated fatty acid esters is greater than or equal to 38% by weight, the percentages by weight being given relative to the total mass of fatty acid esters in the composition.
- R 1 represents a linear carbon chain.
- R2 represents a saturated carbon chain, in particular C1 to C8. It is understood that for at least a portion of the fatty acid esters present in the composition, in the formula (I) at least one of the R 1 or R 2 chains comprises at least one unsaturation, in particular at least R 1 comprises at least one unsaturation.
- the mixture comprises esters of fatty acids for which R 1 represents a C 5 to C 23 carbon chain as defined above comprising one or more unsaturations, and fatty acid esters for which R 1 represents a carbon chain in 05 to 023 as defined above, not containing any unsaturation.
- at least one unsaturation is meant in particular at least one double bond or at least one triple bond.
- the fatty acid esters mentioned in a are, in particular, fatty acid esters in the range from 0 to 10.
- fatty acid esters in the range from 0 to 10.
- methyl or ethyl esters in particular methyl esters, are used.
- the fatty acid esters mentioned in b are in particular 018 fatty acid esters containing at least one unsaturation, such as 0-18: 1 fatty acids, 018: 2 fatty acids and mixtures thereof in all proportions.
- fatty acid esters in 018 to 024 comprising at least one unsaturation, and in particular comprising at least one double bond, at least 10% by weight, and in particular at least 12% by weight, are fatty acid esters in 018: 1, the percentages by mass being given with respect to the total mass of esters of fatty acids in the composition.
- the fatty acid esters come either from an esterification of fatty acids or from a transesterification of triglycerides.
- the fatty acids and triglycerides are advantageously derived from renewable resources, such as vegetable oils and vegetable and animal fats.
- the C6 to C10 fatty acids are preferably saturated. These fatty acids may especially be chosen from hexanoic acid, caprylic acid, capric acid, pelargonic acid and mixtures thereof in all proportions.
- C8-C10 fatty acids are preferably saturated fatty acids; they may in particular be selected from caprylic acid, capric acid, pelargonic acid and mixtures thereof in all proportions.
- a mixture of caprylic acid and capric acid esters is used, in particular a mixture of methyl esters comprising 45 to 70% of caprylate and 30 to 55% of caprate.
- Such fatty acid ester fractions can in particular be obtained from coconut oil and / or palm kernel oil, advantageously from coconut oil.
- the C 8 to C 14 fatty acid esters may in particular be selected from caprylic acid, capric acid, pelargonic acid, lauric acid, myristic acid and mixtures thereof in all proportions. They can be introduced into the composition according to the invention via a particular fraction obtained from coconut oil, palm kernel oil, tallow and / or fish oil, and / or via one of these oils. vegetable / animal fats transesterified.
- the C 8 -C 14 fatty acid esters are introduced into the composition according to the invention via a coconut oil or a transesterified palm oil. It is thus possible to prepare compositions containing methyl, ethyl, isopropyl, butyl, isoamyl or 2-ethylhexyl esters of coconut oil and palm kernel oil.
- C8-C14 fatty acid esters are coconut oil esters.
- the invention thus relates to compositions comprising fatty acid esters of coconut oil and C1 to C8 alcohols at a concentration of 0 to 60% by weight.
- the total concentration of esters is greater than or equal to 35% of the total composition of esters of coconut oil.
- fatty acids and less than or equal to 85%, preferably less than or equal to 80%.
- the subject of the present invention is thus a solubilization composition for organic residues of fossil material comprising a mixture of fatty acid esters characterized in that the mixture of fatty acid esters comprises a mixture of formula : in which
- R1 represents a C5 to C23, in particular C5 to C21, and especially C5 to C19 carbon chain, linear or branched, optionally containing one or more unsaturations,
- R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations
- composition comprising:
- the total concentration of C8 to C10 fatty acid esters and coconut oil fatty acid esters being greater than or equal to 35% of the total fatty acid ester composition, and less than or equal to 85%, preferably less than or equal to 80%.
- concentrations are expressed throughout the present text by mass, based on the total mass of the composition.
- the concentration of C8 to C10 fatty acid esters is less than or equal to 25%, or even less than or equal to 21%
- the concentration of coconut oil fatty acid esters is greater than or equal to 25%. %, in particular greater than or equal to 30%.
- the C18: 2 fatty acid esters are in particular linoleic acid esters.
- the C18: 1 fatty acids may be selected from the group consisting of oleic acid, vaccenic acid and ricinoleic acid; preferably, the ester (s) of C18: 1 fatty acids present in the compositions according to the invention are chosen from oleic acid esters.
- esters may in particular be obtained by esterification or transesterification of rapeseed oil fatty acids, this oil may comprise up to 65% of oleic acid.
- the C 18: 1 fatty acid esters may also, in a manner known per se, be obtained from olive oil or avocado.
- esters may also be obtained from other oils of vegetable or animal origin which may contain at least 20% oleic acid such as: palm, peanut, corn, soya, sunflower, grape, flax, rosin, tallow or fat animal.
- the oleic acid ester is provided in the composition in the form of rapeseed oil ester.
- the subject of the invention is therefore also a solubilization composition for the organic residues of raw material of fossil origin as defined above, comprising a mixture of fatty acid esters of formula: in which
- R1 represents a linear or branched C5 to C23, in particular C17 to C21, carbon chain optionally comprising one or more unsaturations,
- R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations
- composition comprising:
- the total concentration of C 8 to C 10 fatty acid methyl esters and coconut oil fatty acid esters being greater than or equal to 35%, in particular 40% of the total composition, and less than or equal to 85%.
- the coconut oil (or cocoate) esters will comprise a mixture of lauric, myristic, caprylic, capric, oleic, linoleic, stearic and palmitic acid esters. It has been unexpectedly found that compositions having the above characteristics, which can be prepared from renewable raw materials, namely vegetable or animal raw materials, preferably plant materials, have very good properties of dissolution and dispersion of paraffin waxes and by-products of petroleum fractionation and distillation in wide temperature ranges. Generally, from 35 ° C, 70% of the organic residues are dissolved. In addition, these compositions are not flammable or combustible, as is apparent from the measurement of their flash point. Finally, the compositions according to the invention remain liquid at low temperatures, this property being objectified by the measurement of their pour point. The pour point of a product is the temperature at which the product no longer flows.
- compositions according to the invention have a pour point of less than -20 ° C.
- the flash point is the minimum temperature at which the concentration of vapors emitted is sufficient to produce a deflagration on contact with a flame or hot spot under standard conditions, but insufficient to produce the propagation of combustion in the absence of the "pilot" flame.
- a minimum temperature is demonstrated at which the emission of vapors is sufficient to form with the air the flammable gas mixture under the external action of a flame.
- This minimum temperature level is called a flash point.
- fire point There is a second temperature level, beyond the flash point, called fire point, necessary and sufficient for the combustion of the gaseous mixture to be maintained and maintained.
- compositions according to the invention have a flash point greater than 80 ° C., and especially greater than or equal to 90 ° C., advantageously greater than or equal to 93 ° C., in particular greater than or equal to 95 ° C., or even greater than or equal to 100 ° C.
- the composition contains at least 12% by weight of C 18: 1 fatty acid esters, in particular at least 15%, in particular at least 18%.
- the sum of the concentrations of C 8 to C 10 fatty acid methyl esters and of the C 18: 1 fatty acid ester (s) is greater than or equal to 40%, especially greater than or equal to 45%. %, in particular greater than or equal to 50%.
- compositions particularly meeting the objectives of the invention are those for which the C 18: 1 fatty acid esters are alcohol esters for which R 2 represents a C 1 -C 8, in particular C 1 -C 5, carbon chain, more especially C1-C4.
- It may be in particular methyl, ethyl, propyl, isopropyl, butyl, pentyl or isoamyl ester, or mixtures thereof, in particular esters formed with oleic acid.
- compositions containing methyl, butyl or isoamyl esters of rapeseed oil, in particular rapeseed oil methyl esters are chosen from n-butyl oleate, methyl oleate and mixtures thereof; the methyl oleate can be added to the composition in the form of rapeseed oil methyl esters.
- the fatty acid esters mentioned in c) are advantageously chosen from methylcocoate, 2-ethylhexylcocoate and mixtures thereof in all proportions, preferably the fatty acid esters mentioned in c) are esters of coconut and 2-ethylhexanol, also called 2-ethylhexylcocoate.
- the solubilization composition contains at least 36% of methyl esters of C8 to C10 fatty acids.
- composition particularly suitable for the implementation of the invention contains a mixture of fatty acids consisting of:
- C18: 1 fatty acid esters selected from methyl esters, ethyl esters, butyl esters, isoamyl esters, 2-ethylhexyl esters and mixtures thereof, in particular from among the esters methyl, butyl esters and mixtures thereof.
- compositions will advantageously comprise a concentration of rapeseed oil methyl esters greater than or equal to 30%.
- composition may comprise:
- the solubilization composition contains:
- compositions according to any one of the embodiments according to the invention may be used in pure form, or mixed with a solvent.
- the solvent may especially be selected from xylene or mineral oils.
- compositions according to any one of the embodiments of the invention may be used to solubilize or disperse solid bitumens, especially heavy oils, such as paraffins and paraffin waxes or asphaltenes.
- paraffin means saturated hydrocarbons of formula C n H 2 n + 2 with n ranging from 8 to 40.
- the paraffin waxes generally have n greater than or equal to 20.
- the compositions according to any one of the embodiments of the invention may be used to strip and maintain the extraction, refining, transport and storage facilities for oil and its derivatives. They will also be useful for cleaning and stripping any type of device in contact with petroleum derivatives of paraffin or asphaltene type, especially for the degreasing of metal parts in industry or printing presses.
- the compositions according to any one of the embodiments of the invention may also be used in the field of painting, for example as a thinner or binder in paints, or for cleaning surfaces or tools after use.
- compositions according to any one of the embodiments of the invention will also be useful in the construction, as concrete release agent.
- a composition according to the invention can also be used in the field of road coatings, within bituminous binders, for fluidifying the bituminous composition.
- the composition acts as a fluxing agent and facilitates the spreading of the bitumen and the coating of the minerals contained in the bituminous composition.
- compositions and formulations are also included in the invention.
- the subject of the invention is also a process for the preparation of a solubilization composition of the organic residues of raw material of fossil origin, comprising the following mixture of fatty acid esters:
- the rapeseed oil methyl ester composition of the following composition is used:
- n-butyl oleate composition corresponds to a mixture comprising from 68 to 92% of n-butyl oleate, at least 8% of butyl ester of linoleic acid, and from 0 to 2% of butyl ester. of linolenic acid, the remainder being optionally constituted of saturated fatty acid ester in 016 and 018.
- the various constituents of the formulations are mixed in a container at ambient temperature until the formulation is homogenized.
- the flash point and pour point of the formulations are determined by the methods according to ASTM D92 and ASTM D97 respectively.
- Comparative Example 1 for which the total concentration of Methyl C8 / C10 and coconut oil fatty acid esters is 30%, has a pour point greater than -20 ° C, and therefore not suitable for the implementation of the invention, the content of C8 to C14 fatty acid esters of this composition is less than 38% by mass required for the compositions according to the invention.
- the 4X, 5bisX and 8X formulations all have a pour point less than or equal to -20 ° C and a flash point greater than or equal to 100 ° C,
- Example 2 Tests to Determine the Dissolution Temperature The tests are performed with solid organic residues from oil sands oilfields
- the dissolution temperatures of the waxes in the formulations tested are:
- Example 4 Thinner of a composition
- Paraffin was purchased from Panreac: Paraffin CAS [8002-74-2] EC number (EINECS): 232-315-6.
- the fatty acid ester composition is mixed with paraffin in various proportions and heated to 50 ° C.-55 ° C. with 200 rpm magnetic stirring.
- the viscosity of the resulting composition is measured with a Anton Paar Stabinger SVM 300 / G2 Viscometer.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1557410 | 2015-07-31 | ||
PCT/EP2016/068323 WO2017021365A1 (en) | 2015-07-31 | 2016-08-01 | Composition for solubilization of organic residues |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3328978A1 true EP3328978A1 (en) | 2018-06-06 |
Family
ID=54291479
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP16750704.5A Withdrawn EP3328978A1 (en) | 2015-07-31 | 2016-08-01 | Composition for solubilization of organic residues |
Country Status (4)
Country | Link |
---|---|
US (1) | US20180223227A1 (en) |
EP (1) | EP3328978A1 (en) |
CA (1) | CA3006499A1 (en) |
WO (1) | WO2017021365A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20220042348A (en) * | 2019-07-30 | 2022-04-05 | 쉘 인터내셔날 리써취 마트샤피지 비.브이. | Fuel composition with improved stability and method for preparing same |
WO2022191718A1 (en) | 2021-03-08 | 2022-09-15 | Technix EnviroCutter IP Limited | Bitumen cutback compositions and methods of use thereof |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9101850D0 (en) * | 1991-01-29 | 1991-03-13 | Du Pont Howson Ltd | Improvements in or relating to printing |
DE19737071C2 (en) | 1997-08-26 | 1999-09-09 | Henkel Kgaa | Paint remover |
US6824623B1 (en) * | 1999-09-22 | 2004-11-30 | Cognis Corporation | Graffiti remover, paint stripper, degreaser |
EP1595940A1 (en) * | 2004-05-12 | 2005-11-16 | Malaysian Palm Oil Board | High performance cleaning agent |
EP2175010A1 (en) * | 2008-10-10 | 2010-04-14 | Eco Air S.r.l. | Use of fatty acid esters as descaling and lubricating agents |
EP2368971B1 (en) * | 2010-03-18 | 2014-06-18 | DENOLLE, Yann | Use of a combination of a mixture of fatty acid methyl esters in C16-C20 castor oil with at least one ethoxylated glyceride as a cleaning agent |
WO2013073973A1 (en) | 2011-11-16 | 2013-05-23 | Technix Industries Limited | Bitumen cutback agents |
US20150197683A1 (en) * | 2014-01-16 | 2015-07-16 | Elevance Renewable Sciences, Inc. | Olefinic Ester Compositions and Their Use in Oil- and Gas-Related Applications |
-
2016
- 2016-08-01 WO PCT/EP2016/068323 patent/WO2017021365A1/en active Application Filing
- 2016-08-01 CA CA3006499A patent/CA3006499A1/en not_active Abandoned
- 2016-08-01 US US15/749,346 patent/US20180223227A1/en not_active Abandoned
- 2016-08-01 EP EP16750704.5A patent/EP3328978A1/en not_active Withdrawn
Also Published As
Publication number | Publication date |
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WO2017021365A1 (en) | 2017-02-09 |
US20180223227A1 (en) | 2018-08-09 |
CA3006499A1 (en) | 2017-02-09 |
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