GB912926A - Process for purifying phenolic acid oils - Google Patents
Process for purifying phenolic acid oilsInfo
- Publication number
- GB912926A GB912926A GB1378160A GB1378160A GB912926A GB 912926 A GB912926 A GB 912926A GB 1378160 A GB1378160 A GB 1378160A GB 1378160 A GB1378160 A GB 1378160A GB 912926 A GB912926 A GB 912926A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- phthalocyanine
- catalysts
- treatment
- alkaline
- 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.)
- Expired
Links
- 239000003921 oil Substances 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 3
- 150000007965 phenolic acids Chemical class 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 7
- 239000003054 catalyst Substances 0.000 abstract 6
- 239000012670 alkaline solution Substances 0.000 abstract 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 4
- 150000007942 carboxylates Chemical class 0.000 abstract 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 3
- 239000000571 coke Substances 0.000 abstract 3
- 150000002989 phenols Chemical class 0.000 abstract 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 abstract 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 239000000969 carrier Substances 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000377 silicon dioxide Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 229910052720 vanadium Inorganic materials 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052792 caesium Inorganic materials 0.000 abstract 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002131 composite material Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000356 contaminant Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000003502 gasoline Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052701 rubidium Inorganic materials 0.000 abstract 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
- 229960004319 trichloroacetic acid Drugs 0.000 abstract 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C10G19/00—Refining hydrocarbon oils in the absence of hydrogen, by alkaline treatment
- C10G19/08—Recovery of used refining agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Catalysts (AREA)
Abstract
Catalysts for use in purifying alkaline solutions of acid oil, consisting substantially of phenolic compounds and carboxylic acids containing mercaptans (see Group IV(b)) comprise phthalocyanine sulphonates or carboxylates supported on a carrier. Metal phthalocyanine sulphonates and carboxylates are preferred, e.g. those of iron and copper and in particular cobalt and vanadium phthalocyanine sulphonates. Carriers specified include various charcoals, coke, silica, alumina and silica-alumina composites. The latter usually being activated by acid on heat-treatment. The catalysts are prepared by treating particles of the solid carrier with solutions of the phthalocyanines.ALSO:In a process of purifying an acid oil consisting substantially of phenolic compounds and carboxylic acids and containing mercaptans as contaminants, an alkaline solution of said acid oil containing mercaptans is subjected to an oxidizing treatment with a gas containing free oxygen in the presence of a phthalocyanine sulphonate or carboxylate catalyst at a temperature of from atmospheric to 205 DEG C. whereby the mercaptans are converted to disulphides and thereafter the resulting disulphides are separated as an upper layer or extracted by a normally liquid hydrocarbon fraction from said alkaline solution and the phenolic compounds are recovered from the purified alkaline solution. Preferred catalysts are commercial cobalt phthalocyanine disulphonate containing the monosulphonate and vanadium phthalocyanine sulphonate. Other metal phthalocyanine sulphonates and carboxylates specified include those of iron and copper. Such compounds may be prepared by reacting the corresponding phthalocyanine with fuming sulphuric acid. Carboxylated catalysts may be prepared by the action of trichloracetic acid or of phosgene and aluminium chloride or the corresponding phthalocyanines, the acid chloride formed in the latter reaction being converted to the acid by hydrolysis. As alkaline solvents are specified aqueous solutions of sodium, potassium, lithium, rubidium, caesium and ammonium hydroxides. The catalyst may be in solution in the aqueous alkali or associated with solid carriers representative of those mentioned being charcoals, coke, silica and alumina which may be activated by treatment with acid or heat. The examples relate to the treatment of alkaline solutions of acid oils obtained from cracked gasoline, kerosene and coke oils. Apparatus for carrying out the process is described with reference to a flow sheet (not shown).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US808721A US2976229A (en) | 1959-04-24 | 1959-04-24 | Purification of acid oils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB912926A true GB912926A (en) | 1962-12-12 |
Family
ID=25199533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1378160A Expired GB912926A (en) | 1959-04-24 | 1960-04-20 | Process for purifying phenolic acid oils |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB912926A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1270704A1 (en) * | 2001-06-26 | 2003-01-02 | Uop Llc | A process for removing sulfur compounds from hydrocarbon streams |
| EP2588432A4 (en) * | 2010-06-30 | 2014-07-23 | Uop Llc | Process for removing one or more sulfur compounds from a stream |
-
1960
- 1960-04-20 GB GB1378160A patent/GB912926A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1270704A1 (en) * | 2001-06-26 | 2003-01-02 | Uop Llc | A process for removing sulfur compounds from hydrocarbon streams |
| EP2588432A4 (en) * | 2010-06-30 | 2014-07-23 | Uop Llc | Process for removing one or more sulfur compounds from a stream |
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