PL112578B1 - Method of selective isolation of dienes from dienes containing mixtures - Google Patents
Method of selective isolation of dienes from dienes containing mixtures Download PDFInfo
- Publication number
- PL112578B1 PL112578B1 PL1977195313A PL19531377A PL112578B1 PL 112578 B1 PL112578 B1 PL 112578B1 PL 1977195313 A PL1977195313 A PL 1977195313A PL 19531377 A PL19531377 A PL 19531377A PL 112578 B1 PL112578 B1 PL 112578B1
- Authority
- PL
- Poland
- Prior art keywords
- column
- head
- line
- mixture
- hydrocarbons
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 57
- 238000000034 method Methods 0.000 title claims description 27
- 238000002955 isolation Methods 0.000 title description 4
- 150000001993 dienes Chemical class 0.000 title 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 150000002430 hydrocarbons Chemical class 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 14
- -1 diene hydrocarbons Chemical class 0.000 claims description 14
- 238000000895 extractive distillation Methods 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000008096 xylene Substances 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003738 xylenes Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 238000005336 cracking Methods 0.000 claims description 3
- 238000002407 reforming Methods 0.000 claims description 3
- 238000000197 pyrolysis Methods 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 238000002386 leaching Methods 0.000 claims 2
- 238000000605 extraction Methods 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000010586 diagram Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 229930195734 saturated hydrocarbon Natural products 0.000 description 6
- 238000005201 scrubbing Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-MICDWDOJSA-N 1-deuteriopent-1-ene Chemical compound [2H]C=CCCC YWAKXRMUMFPDSH-MICDWDOJSA-N 0.000 description 1
- BOFLDKIFLIFLJA-UHFFFAOYSA-N 2-methylbut-1-en-3-yne Chemical group CC(=C)C#C BOFLDKIFLIFLJA-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- VADUDTKCGJKNDY-UHFFFAOYSA-N 4-Methyl-4-penten-2-one Chemical compound CC(=C)CC(C)=O VADUDTKCGJKNDY-UHFFFAOYSA-N 0.000 description 1
- FGQBGDBLZZPFCM-UHFFFAOYSA-N 4-methylmorpholin-3-one Chemical compound CN1CCOCC1=O FGQBGDBLZZPFCM-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 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
- 238000002156 mixing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008674 spewing Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
- C10G21/20—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19241/76A IT1063231B (it) | 1976-01-14 | 1976-01-14 | Impiego di n-metil-morfolin-3-one quale solvente per la separazione di idrocarburi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL112578B1 true PL112578B1 (en) | 1980-10-31 |
Family
ID=11156044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977195313A PL112578B1 (en) | 1976-01-14 | 1977-01-14 | Method of selective isolation of dienes from dienes containing mixtures |
Country Status (35)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107074688B (zh) * | 2014-09-05 | 2020-12-01 | Scg化学有限公司 | 用于c8芳香族混合物的分离方法 |
| EP3189023B1 (en) * | 2014-09-05 | 2021-08-04 | SCG Chemicals Company Limited | Process for the enhanced separation of ethylbenzene |
-
1976
- 1976-01-14 IT IT19241/76A patent/IT1063231B/it active
-
1977
- 1977-01-07 GR GR52529A patent/GR59765B/el unknown
- 1977-01-07 ZA ZA770096A patent/ZA7796B/xx unknown
- 1977-01-07 AU AU21127/77A patent/AU508405B2/en not_active Expired
- 1977-01-11 CH CH30377A patent/CH631203A5/it not_active IP Right Cessation
- 1977-01-11 TR TR19071A patent/TR19071A/xx unknown
- 1977-01-12 LU LU76552A patent/LU76552A1/xx unknown
- 1977-01-12 EG EG21/77A patent/EG12337A/xx active
- 1977-01-12 SE SE7700250A patent/SE423535B/xx unknown
- 1977-01-12 AR AR266162A patent/AR214059A1/es active
- 1977-01-12 NO NO770098A patent/NO148370C/no unknown
- 1977-01-13 CA CA269,662A patent/CA1091615A/en not_active Expired
- 1977-01-13 AT AT16277A patent/AT356790B/de not_active IP Right Cessation
- 1977-01-13 GB GB1402/77A patent/GB1523412A/en not_active Expired
- 1977-01-13 PT PT66065A patent/PT66065B/pt unknown
- 1977-01-13 FR FR7700935A patent/FR2338235A1/fr active Granted
- 1977-01-13 IN IN43/CAL/77A patent/IN145336B/en unknown
- 1977-01-13 YU YU83/77A patent/YU39984B/xx unknown
- 1977-01-13 IE IE63/77A patent/IE45113B1/en unknown
- 1977-01-13 RO RO7789042A patent/RO70373A/ro unknown
- 1977-01-13 HU HU77SA3004A patent/HU178726B/hu unknown
- 1977-01-13 DK DK12577A patent/DK12577A/da not_active Application Discontinuation
- 1977-01-14 ES ES455306A patent/ES455306A1/es not_active Expired
- 1977-01-14 MW MW1/77A patent/MW177A1/xx unknown
- 1977-01-14 DD DD7700196937A patent/DD128592A5/xx unknown
- 1977-01-14 NL NL7700405A patent/NL7700405A/xx not_active Application Discontinuation
- 1977-01-14 BE BE174097A patent/BE850400A/xx not_active IP Right Cessation
- 1977-01-14 PL PL1977195313A patent/PL112578B1/pl unknown
- 1977-01-14 DE DE2701466A patent/DE2701466C3/de not_active Expired
- 1977-01-14 MX MX167704A patent/MX144633A/es unknown
- 1977-01-14 ZM ZM6/77A patent/ZM677A1/xx unknown
- 1977-01-14 JP JP253277A patent/JPS5288278A/ja active Pending
- 1977-01-14 CS CS77242A patent/CS200504B2/cs unknown
- 1977-01-14 BR BR7700296A patent/BR7700296A/pt unknown
- 1977-01-14 PH PH19358A patent/PH13737A/en unknown
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