US2951886A - Recovery and purification of benzene - Google Patents
Recovery and purification of benzene Download PDFInfo
- Publication number
- US2951886A US2951886A US728620A US72862058A US2951886A US 2951886 A US2951886 A US 2951886A US 728620 A US728620 A US 728620A US 72862058 A US72862058 A US 72862058A US 2951886 A US2951886 A US 2951886A
- Authority
- US
- United States
- Prior art keywords
- benzene
- approximately
- temperature
- stock
- catalyst
- 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 - Lifetime
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims description 160
- 238000011084 recovery Methods 0.000 title description 5
- 238000000746 purification Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 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 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 7
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 6
- 238000004523 catalytic cracking Methods 0.000 claims description 6
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 6
- 238000006396 nitration reaction Methods 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000003921 oil Substances 0.000 description 31
- 239000011280 coal tar Substances 0.000 description 21
- 239000012535 impurity Substances 0.000 description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 239000011593 sulfur Substances 0.000 description 14
- 239000008096 xylene Substances 0.000 description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 11
- 238000004517 catalytic hydrocracking Methods 0.000 description 8
- 239000000571 coke Substances 0.000 description 8
- 238000005336 cracking Methods 0.000 description 8
- 239000012263 liquid product Substances 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000017858 demethylation Effects 0.000 description 5
- 238000010520 demethylation reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 150000003577 thiophenes Chemical class 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000001066 destructive effect Effects 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000005172 methylbenzenes Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 alkyl benzene compounds Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- IHICGCFKGWYHSF-UHFFFAOYSA-N C1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1C Chemical group C1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1C IHICGCFKGWYHSF-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- WHDPTDWLEKQKKX-UHFFFAOYSA-N cobalt molybdenum Chemical compound [Co].[Co].[Mo] WHDPTDWLEKQKKX-UHFFFAOYSA-N 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/04—Benzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
- C07C4/18—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/26—Chromium
-
- 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
- C10G2400/30—Aromatics
Definitions
- This invention relates to the recovery and purification of benzene from crude coke oven or coal tar light oils.
- While the invention has been disclosed principally in relation to the recovery of purified benzene from coal tar light oil, the invention is also useful for the treatment of other types of charge stocks containing benzene such as relatively high boiling catalytic reformate fractions.
- a catalytic reformate boiling in the 300- 400 F. range containing 80-85% alkyl substituted benzenes and 15-20% parattins may be used as the charge stock in the practice of the present invention to produce a hikh yield of benzene, thereby up-grading the commercial value of the reformate.
- the process of recovering benzene of at least nitration grade purity from an impure hydrocarbon stock containing benzene and alkyl benzene components which '6 process comprises subjecting the said stock, in a single pass, to catalytic cracking conditions in the presence of hydrogen and a catalyst consisting of approximately to by weight of chromium oxide on a high purity 5 low sodium content gamma-type alumina support, at a temperature above approximately 1200 F. whereby a 7 high yield of benzene is obtained.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL113125D NL113125C (sv) | 1958-04-15 | ||
BE577729D BE577729A (sv) | 1958-04-15 | ||
US728620A US2951886A (en) | 1958-04-15 | 1958-04-15 | Recovery and purification of benzene |
DEP1270A DE1270017B (de) | 1958-04-15 | 1959-04-13 | Verfahren zur Gewinnung von hochgereinigtem Benzol |
ES0248649A ES248649A1 (es) | 1958-04-15 | 1959-04-14 | Un procedimiento de recuperacion y purificacion de benceno |
FR792137A FR1221539A (fr) | 1958-04-15 | 1959-04-15 | Procédé de récupération et de purification du benzène |
GB12817/59A GB916597A (en) | 1958-04-15 | 1959-04-15 | Process of recovering and purifying benzene |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US728620A US2951886A (en) | 1958-04-15 | 1958-04-15 | Recovery and purification of benzene |
Publications (1)
Publication Number | Publication Date |
---|---|
US2951886A true US2951886A (en) | 1960-09-06 |
Family
ID=24927590
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US728620A Expired - Lifetime US2951886A (en) | 1958-04-15 | 1958-04-15 | Recovery and purification of benzene |
Country Status (7)
Country | Link |
---|---|
US (1) | US2951886A (sv) |
BE (1) | BE577729A (sv) |
DE (1) | DE1270017B (sv) |
ES (1) | ES248649A1 (sv) |
FR (1) | FR1221539A (sv) |
GB (1) | GB916597A (sv) |
NL (1) | NL113125C (sv) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3055956A (en) * | 1959-10-05 | 1962-09-25 | Ashland Oil Inc | Process for the separation of naphthalene |
US3081259A (en) * | 1963-03-12 | Coke oven light oil purification | ||
US3207802A (en) * | 1960-12-14 | 1965-09-21 | Air Prod & Chem | Purification of coke-oven light oil |
US3213151A (en) * | 1962-07-27 | 1965-10-19 | Phillips Petroleum Co | Recovery of hydrogen from gaseous mixtures and improved hydrogenation process |
US3284522A (en) * | 1964-04-20 | 1966-11-08 | Air Prod & Chem | Cyclohexane production |
US3285986A (en) * | 1962-03-12 | 1966-11-15 | Phillips Petroleum Co | Separation process |
EP0098538A2 (en) * | 1982-07-06 | 1984-01-18 | Air Products And Chemicals, Inc. | Process for the hydrodealkylation of alkyl-aromatic hydrocarbons, process for the hydrodesulfurization of a hydrocarbon gas stream, and catalyst therefor |
US4451687A (en) * | 1982-07-06 | 1984-05-29 | Air Products And Chemicals, Inc. | Catalyst for the hydrodealkylation of alkylaromatic compounds |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB667145A (en) * | 1949-10-26 | 1952-02-27 | Peter William Reynolds | Improvements in and relating to the production of alumina |
US2705733A (en) * | 1950-05-20 | 1955-04-05 | Basf Ag | Purification of crude benzene |
US2734929A (en) * | 1956-02-14 | Dealkylation of hydrocarbons | ||
US2773917A (en) * | 1952-09-16 | 1956-12-11 | Socony Mobil Oil Co | Demethylation over chromia or molybdena catalysts |
US2780661A (en) * | 1951-08-15 | 1957-02-05 | Exxon Research Engineering Co | Reforming followed by hydrodealkylation |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2402854A (en) * | 1940-06-13 | 1946-06-25 | Universal Oil Prod Co | Hydrocarbon conversion |
US2774801A (en) * | 1952-09-16 | 1956-12-18 | Socony Mobil Oil Co Inc | Conversion of methylnaphthalenes |
-
0
- BE BE577729D patent/BE577729A/xx unknown
- NL NL113125D patent/NL113125C/xx active
-
1958
- 1958-04-15 US US728620A patent/US2951886A/en not_active Expired - Lifetime
-
1959
- 1959-04-13 DE DEP1270A patent/DE1270017B/de active Pending
- 1959-04-14 ES ES0248649A patent/ES248649A1/es not_active Expired
- 1959-04-15 FR FR792137A patent/FR1221539A/fr not_active Expired
- 1959-04-15 GB GB12817/59A patent/GB916597A/en not_active Expired
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2734929A (en) * | 1956-02-14 | Dealkylation of hydrocarbons | ||
GB667145A (en) * | 1949-10-26 | 1952-02-27 | Peter William Reynolds | Improvements in and relating to the production of alumina |
US2705733A (en) * | 1950-05-20 | 1955-04-05 | Basf Ag | Purification of crude benzene |
US2780661A (en) * | 1951-08-15 | 1957-02-05 | Exxon Research Engineering Co | Reforming followed by hydrodealkylation |
US2773917A (en) * | 1952-09-16 | 1956-12-11 | Socony Mobil Oil Co | Demethylation over chromia or molybdena catalysts |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3081259A (en) * | 1963-03-12 | Coke oven light oil purification | ||
US3055956A (en) * | 1959-10-05 | 1962-09-25 | Ashland Oil Inc | Process for the separation of naphthalene |
US3207802A (en) * | 1960-12-14 | 1965-09-21 | Air Prod & Chem | Purification of coke-oven light oil |
US3285986A (en) * | 1962-03-12 | 1966-11-15 | Phillips Petroleum Co | Separation process |
US3213151A (en) * | 1962-07-27 | 1965-10-19 | Phillips Petroleum Co | Recovery of hydrogen from gaseous mixtures and improved hydrogenation process |
US3284522A (en) * | 1964-04-20 | 1966-11-08 | Air Prod & Chem | Cyclohexane production |
EP0098538A2 (en) * | 1982-07-06 | 1984-01-18 | Air Products And Chemicals, Inc. | Process for the hydrodealkylation of alkyl-aromatic hydrocarbons, process for the hydrodesulfurization of a hydrocarbon gas stream, and catalyst therefor |
US4436836A (en) | 1982-07-06 | 1984-03-13 | Air Products And Chemicals, Inc. | Catalyst for the hydrodealkylation of alkylaromatic compounds |
US4451687A (en) * | 1982-07-06 | 1984-05-29 | Air Products And Chemicals, Inc. | Catalyst for the hydrodealkylation of alkylaromatic compounds |
EP0098538A3 (en) * | 1982-07-06 | 1984-06-06 | Air Products And Chemicals, Inc. | Process for the hydrodealkylation of alkyl-aromatic hydrocarbons, process for the hydrodesulfurization of a hydrocarbon gas stream, and catalyst therefor |
Also Published As
Publication number | Publication date |
---|---|
GB916597A (en) | 1963-01-23 |
ES248649A1 (es) | 1959-09-16 |
FR1221539A (fr) | 1960-06-02 |
BE577729A (sv) | |
NL113125C (sv) | |
DE1270017B (de) | 1968-06-12 |
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