DE947792C - Verfahren zur Herstellung reiner aromatischer Kohlenwasserstoffe - Google Patents
Verfahren zur Herstellung reiner aromatischer KohlenwasserstoffeInfo
- Publication number
- DE947792C DE947792C DES28334A DES0028334A DE947792C DE 947792 C DE947792 C DE 947792C DE S28334 A DES28334 A DE S28334A DE S0028334 A DES0028334 A DE S0028334A DE 947792 C DE947792 C DE 947792C
- Authority
- DE
- Germany
- Prior art keywords
- fraction
- xylene
- toluene
- boiling
- reformate
- 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
- 238000000034 method Methods 0.000 title claims description 24
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 144
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 102
- 239000008096 xylene Substances 0.000 claims description 61
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 54
- 238000009835 boiling Methods 0.000 claims description 51
- 238000004821 distillation Methods 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 35
- 239000003463 adsorbent Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 239000001273 butane Substances 0.000 claims description 16
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 16
- 238000001179 sorption measurement Methods 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006073 displacement reaction Methods 0.000 claims description 2
- 230000000274 adsorptive effect Effects 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 239000007792 gaseous phase Substances 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 238000003795 desorption Methods 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- 238000002407 reforming Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000006096 absorbing agent Substances 0.000 description 9
- 238000006356 dehydrogenation reaction Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 150000003738 xylenes Chemical class 0.000 description 7
- 239000000470 constituent Substances 0.000 description 6
- 239000010779 crude oil Substances 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000001833 catalytic reforming Methods 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005899 aromatization reaction Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- QWHNJUXXYKPLQM-UHFFFAOYSA-N dimethyl cyclopentane Natural products CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000004992 fission Effects 0.000 description 2
- -1 occur.If desired Chemical compound 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C07C15/067—C8H10 hydrocarbons
- C07C15/08—Xylenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/367—Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
- C07C5/387—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation of cyclic compounds containing non six-membered ring to compounds containing a six-membered aromatic ring
-
- 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
- C10G61/00—Treatment of naphtha by at least one reforming process and at least one process of refining in the absence of hydrogen
- C10G61/02—Treatment of naphtha by at least one reforming process and at least one process of refining in the absence of hydrogen plural serial stages only
- C10G61/06—Treatment of naphtha by at least one reforming process and at least one process of refining in the absence of hydrogen plural serial stages only the refining step being a sorption process
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1059961XA | 1951-05-04 | 1951-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE947792C true DE947792C (de) | 1956-08-23 |
Family
ID=22308923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES28334A Expired DE947792C (de) | 1951-05-04 | 1952-04-29 | Verfahren zur Herstellung reiner aromatischer Kohlenwasserstoffe |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE511130A (en, 2012) |
| DE (1) | DE947792C (en, 2012) |
| FR (1) | FR1059961A (en, 2012) |
| GB (1) | GB712712A (en, 2012) |
| NL (1) | NL78811C (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190300801A1 (en) * | 2018-03-30 | 2019-10-03 | Exxonmobil Research And Engineering Company | Staged removal of aromatics in naphtha reforming |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2509486A (en) * | 1946-04-26 | 1950-05-30 | Universal Oil Prod Co | Separation of hydrocarbons |
| US2514580A (en) * | 1948-04-14 | 1950-07-11 | Sun Oil Co | Separation of hydrocarbons |
| US2528693A (en) * | 1947-03-04 | 1950-11-07 | Shell Dev | Production of aromatic hydrocarbons by dehydrogenation of naphthenes |
| US2545153A (en) * | 1947-11-12 | 1951-03-13 | Kellogg M W Co | Preparation of aromatics from petroleum distillates |
-
1952
- 1952-04-17 FR FR1059961D patent/FR1059961A/fr not_active Expired
- 1952-04-24 GB GB10334/52A patent/GB712712A/en not_active Expired
- 1952-04-29 DE DES28334A patent/DE947792C/de not_active Expired
- 1952-04-29 NL NL78811D patent/NL78811C/xx active
- 1952-05-02 BE BE511130D patent/BE511130A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2509486A (en) * | 1946-04-26 | 1950-05-30 | Universal Oil Prod Co | Separation of hydrocarbons |
| US2528693A (en) * | 1947-03-04 | 1950-11-07 | Shell Dev | Production of aromatic hydrocarbons by dehydrogenation of naphthenes |
| US2545153A (en) * | 1947-11-12 | 1951-03-13 | Kellogg M W Co | Preparation of aromatics from petroleum distillates |
| US2514580A (en) * | 1948-04-14 | 1950-07-11 | Sun Oil Co | Separation of hydrocarbons |
Also Published As
| Publication number | Publication date |
|---|---|
| NL78811C (en, 2012) | 1955-08-15 |
| BE511130A (en, 2012) | 1953-11-20 |
| GB712712A (en) | 1954-07-28 |
| FR1059961A (fr) | 1954-03-30 |
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