EP0495941A1 - Procede empechant la solubilisation dans l'eau d'alcools, a l'etat pur ou melanges a des hydrocarbures, et additifs utilises a cet effet - Google Patents
Procede empechant la solubilisation dans l'eau d'alcools, a l'etat pur ou melanges a des hydrocarbures, et additifs utilises a cet effetInfo
- Publication number
- EP0495941A1 EP0495941A1 EP91913064A EP91913064A EP0495941A1 EP 0495941 A1 EP0495941 A1 EP 0495941A1 EP 91913064 A EP91913064 A EP 91913064A EP 91913064 A EP91913064 A EP 91913064A EP 0495941 A1 EP0495941 A1 EP 0495941A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alcohols
- water
- alcohol
- process according
- hydrocarbons
- 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.)
- Ceased
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 38
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 37
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 15
- 230000007928 solubilization Effects 0.000 title claims abstract description 14
- 238000005063 solubilization Methods 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 title claims description 20
- 239000000654 additive Substances 0.000 title description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000003112 inhibitor Substances 0.000 claims abstract description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 12
- 239000003792 electrolyte Substances 0.000 claims description 11
- 239000000446 fuel Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 5
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 4
- 230000002195 synergetic effect Effects 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 3
- 230000008014 freezing Effects 0.000 claims description 3
- 238000007710 freezing Methods 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000013535 sea water Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 238000006664 bond formation reaction Methods 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/94—Use of additives, e.g. for stabilisation
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
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- C10L1/1233—Inorganic compounds oxygen containing compounds, e.g. oxides, hydroxides, acids and salts thereof
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
- C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
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- C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
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- C10L1/14—Organic compounds
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- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
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- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
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- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
Definitions
- phase alcohols + water is heavier and goes to the bottom of the tank of the automobile; once intaken this causes the engine to stop, damaging it.
- solubilization will be inhibited if in the water there will be present a compound that will form a hydrogen bond with it, stronger than that of water-alcohol.
- the phenol can be dissolved in an opportune solvent that notably lowers the freezing point.
- the solvents that increase the water tolerance of the alcohols can be alcohols superior to butyl alcohol, benzene, toluene, xylene, 4 methylpentane 2-1, cumene , hexane. They can furthermore be considered compounds of synergic action as the organic acetates (of methyl, of ethyl, of isoamyl, of t-butyl, etc.), the methylcyclopentane, the triethylamine , etc.
- the aniline can be used, or, better still, the N-methylaniline.
- Such compounds have an effect that is comparable to phenol as regards to the alcoholic phase and/or hydrocarbon phase mentioned.
- the N-methylaniline has a low freezing point (-57°C) therefore it can be used together with phenol both as a solvent and as a compound of synergic action.
- the addition to phenol of aniline and/or of N-methylaniline has furthermore the advantage of diminishing the copper corrosion (ASTM D 130) of gasoline.
- NaCl or KC1 dissolved in the fuel by means of alcohol, would in fact become a solution in water if they came into contact with water that was not very inhibited, thus contributing a limited solubilization of the alcohol in a water phase.
- Such a solution would furthermore have the advantage of "inhibiting" eventual water carry-over present in the nydrocarbon compound of blending.
- this type of electrolytes can also be used in the storage tank at the production site. Since a certain amount of water is always present in the storage tanks, it is necessary that prior to the storage of the alcohols, or of their mixtures with HC , the tank shoul ⁇ be emptied and totally drained of water that is p r e s e n t .
- the dosage of the inhibitor in alcohol/HC phase is carried out on the ground of the water present in the tank, maintaining themselves conservative to keep count of eventual water carry-over in the blending components.
- the fuel maintains its retentive properties with regards to the alcohols in case it should come into contact with water that has been totally untreated.
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Liquid Carbonaceous Fuels (AREA)
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Abstract
Le procédé décrit empêche la solubilisation dans l'eau d'alcools, à l'état pur ou mélangés à des hydrocarbures, grâce à la présence d'inhibiteurs de formation de liaisons hydrogéne dans la phase alcool et/ou dans la phase hydrocarbure et/ou dans la phase eau, ce qui permet d'exploiter la teneur en octane et les faibles émissions des alcools, pour formuler ainsi un nouveau type d'essence sans plomb.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT01870890A IT1243220B (it) | 1990-07-24 | 1990-07-24 | Procedimento per impedire la solubilizzazione in acqua di alcoli, da soli o in miscela con idrocarburi ed additivii a tale scopo |
IT1870890 | 1990-07-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0495941A1 true EP0495941A1 (fr) | 1992-07-29 |
Family
ID=11153301
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91913064A Ceased EP0495941A1 (fr) | 1990-07-24 | 1991-07-22 | Procede empechant la solubilisation dans l'eau d'alcools, a l'etat pur ou melanges a des hydrocarbures, et additifs utilises a cet effet |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0495941A1 (fr) |
IT (1) | IT1243220B (fr) |
WO (1) | WO1992001770A1 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2726827C1 (ru) * | 2019-09-17 | 2020-07-15 | Единый Евгений Васильевич | Высокооктановое топливо |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2966029A (en) * | 1957-04-24 | 1960-12-27 | Gulf Research Development Co | Corrosion inhibited fuels containing vanadium |
US3082070A (en) * | 1959-01-28 | 1963-03-19 | Texaco Inc | Motor fuel containing synergistic octane appreciator |
DE2216880C2 (de) * | 1971-05-05 | 1983-08-25 | Österreichische Hiag-Werke AG, Wien | Treibstoffzusatz |
US3955938A (en) * | 1973-08-21 | 1976-05-11 | Exxon Research And Engineering Company | Gasoline composition containing a sodium additive |
FR2241610A1 (en) * | 1973-08-22 | 1975-03-21 | Svenka Utvecklingsaktiebolaget | Hydrocarbon fuels contg. water in micro-emulsion form - and soluble inorganic salts to increase octane ratings |
DE2440521A1 (de) * | 1973-08-28 | 1975-03-06 | Svenska Utvecklings Ab | Treibstoffmaterial mit erhoehter octanzahl |
FR2453210A1 (fr) * | 1979-04-06 | 1980-10-31 | Ugine Kuhlmann | Procede de stabilisation des melanges d'essence et de methanol |
US4568354A (en) * | 1985-06-03 | 1986-02-04 | Texaco Inc. | Conversion of hazy gasoline to clear stable gasoline |
EP0288296B2 (fr) * | 1987-04-23 | 1999-03-31 | Lubrizol Adibis Holdings (Uk) Limited | Composition de combustible contenant un additif pour diminuer le recul de l'assise de soupape |
ATE107347T1 (de) * | 1988-01-27 | 1994-07-15 | Lubrizol Corp | Brennstoffzusammensetzung. |
-
1990
- 1990-07-24 IT IT01870890A patent/IT1243220B/it active IP Right Grant
-
1991
- 1991-07-22 WO PCT/IT1991/000062 patent/WO1992001770A1/fr not_active Application Discontinuation
- 1991-07-22 EP EP91913064A patent/EP0495941A1/fr not_active Ceased
Non-Patent Citations (1)
Title |
---|
See references of WO9201770A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO1992001770A1 (fr) | 1992-02-06 |
IT1243220B (it) | 1994-05-24 |
IT9018708A1 (it) | 1992-01-24 |
IT9018708A0 (it) | 1990-07-24 |
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