CA1053601A - Distillation extractive - Google Patents

Distillation extractive

Info

Publication number: CA1053601A
Authority: CA; Canada
Prior art keywords: solvent; stream; sulfolane; feedstock; aromatics
Prior art date: 1974-05-30
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

Application number

CA225,704A

Other languages

English (en)

Inventor

Martin R. Cines

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Phillips Petroleum Co

Original Assignee

Phillips Petroleum Co

Priority date (The priority date 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 date listed.)

1974-05-30

Filing date

1975-04-29

Publication date

1979-05-01

1975-04-29 Application filed by Phillips Petroleum Co filed Critical Phillips Petroleum Co

1979-05-01 Application granted granted Critical

1979-05-01 Publication of CA1053601A publication Critical patent/CA1053601A/fr

Status Expired legal-status Critical Current

Links

238000000895 extractive distillation Methods 0.000 title claims abstract description 48
239000002904 solvent Substances 0.000 claims abstract description 128
238000000034 method Methods 0.000 claims abstract description 59
238000010992 reflux Methods 0.000 claims abstract description 54
239000007791 liquid phase Substances 0.000 claims abstract description 34
238000000926 separation method Methods 0.000 claims description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 22
150000001336 alkenes Chemical class 0.000 claims description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
239000003502 gasoline Substances 0.000 claims description 15
239000007788 liquid Substances 0.000 claims description 14
238000009835 boiling Methods 0.000 claims description 11
239000012071 phase Substances 0.000 claims description 10
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 8
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
238000004064 recycling Methods 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
238000000197 pyrolysis Methods 0.000 claims description 5
239000008096 xylene Substances 0.000 claims description 5
150000003738 xylenes Chemical class 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
235000013844 butane Nutrition 0.000 claims description 4
238000004508 fractional distillation Methods 0.000 claims description 4
-1 glycol ethers Chemical class 0.000 claims description 4
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical group O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 claims description 3
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
DYGJDTCGUUMUBL-UHFFFAOYSA-N 2,3-dihydrothiophene 1,1-dioxide Chemical compound O=S1(=O)CCC=C1 DYGJDTCGUUMUBL-UHFFFAOYSA-N 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
150000002334 glycols Chemical class 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
UGDAWAQEKLURQI-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;hydrate Chemical compound O.OCCOCCO UGDAWAQEKLURQI-UHFFFAOYSA-N 0.000 claims 4
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
239000001273 butane Substances 0.000 claims 1
238000004523 catalytic cracking Methods 0.000 claims 1
239000006184 cosolvent Substances 0.000 claims 1
239000003208 petroleum Substances 0.000 claims 1
238000004227 thermal cracking Methods 0.000 claims 1
238000002485 combustion reaction Methods 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 description 10
229910052717 sulfur Inorganic materials 0.000 description 9
229930195733 hydrocarbon Natural products 0.000 description 8
150000002430 hydrocarbons Chemical class 0.000 description 8
239000004215 Carbon black (E152) Substances 0.000 description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000004821 distillation Methods 0.000 description 7
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
239000011593 sulfur Substances 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
101150034533 ATIC gene Proteins 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
238000013459 approach Methods 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000446 fuel Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
235000020030 perry Nutrition 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical compound CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
241000357297 Atypichthys strigatus Species 0.000 description 1
101100114362 Caenorhabditis elegans col-7 gene Proteins 0.000 description 1
101100150284 Caenorhabditis elegans sre-8 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
102100025597 Caspase-4 Human genes 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
101100273284 Homo sapiens CASP4 gene Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229940078552 o-xylene Drugs 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 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
229920001451 polypropylene glycol Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000002407 reforming Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
229910052815 sulfur oxide Inorganic materials 0.000 description 1
ISNYUQWBWALXEY-OMIQOYQYSA-N tsg6xhx09r Chemical compound O([C@@H](C)C=1[C@@]23CN(C)CCO[C@]3(C3=CC[C@H]4[C@]5(C)CC[C@@](C4)(O)O[C@@]53[C@H](O)C2)CC=1)C(=O)C=1C(C)=CNC=1C ISNYUQWBWALXEY-OMIQOYQYSA-N 0.000 description 1
OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/40—Extractive distillation
- 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

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)
Analytical Chemistry (AREA)
Water Supply & Treatment (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Medicines Containing Plant Substances (AREA)

CA225,704A 1974-05-30 1975-04-29 Distillation extractive Expired CA1053601A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US47449874A	1974-05-30	1974-05-30

Publications (1)

Publication Number	Publication Date
CA1053601A true CA1053601A (fr)	1979-05-01

Family

ID=23883787

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA225,704A Expired CA1053601A (fr)	1974-05-30	1975-04-29	Distillation extractive

Country Status (9)

Country	Link
BE (1)	BE829720A (fr)
CA (1)	CA1053601A (fr)
DE (1)	DE2523704A1 (fr)
ES (1)	ES437977A1 (fr)
FR (1)	FR2275234A1 (fr)
GB (1)	GB1505722A (fr)
IT (1)	IT1038564B (fr)
NO (1)	NO140619C (fr)
ZA (1)	ZA753433B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA81448B (en) *	1980-01-28	1982-02-24	Int Synthetic Rubber	Polymerisation purification
GB2163773B (en) *	1984-08-31	1988-04-20	El Paso Products Co	Process for recovering tertiary butylstyrene
US4514261A (en) *	1984-08-31	1985-04-30	El Paso Products Company	Refining of tertiary butylstyrene
DE3528071A1 (de) *	1985-08-05	1987-02-05	Linde Ag	Verfahren zur zerlegung eines kohlenwasserstoffgemisches
ES2043551B1 (es) *	1992-05-18	1994-07-01	Consejo Superior Investigacion	Dispositivo para la separacion y concentracion de componentes volatiles de muestras termosensibles por destilacion y extraccion simultanea mediante disolventes organicos.
US6551502B1 (en) *	2000-02-11	2003-04-22	Gtc Technology Corporation	Process of removing sulfur compounds from gasoline
CN104718276B (zh)	2012-08-09	2017-08-25	科学工业研究委员会	用于通过从含有机过氧化物的未加工的裂化汽油馏分回收高纯度苯来制备贫苯汽油的方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL64177C (fr) *	1943-02-08

1975
- 1975-04-29 CA CA225,704A patent/CA1053601A/fr not_active Expired
- 1975-05-16 GB GB20909/75A patent/GB1505722A/en not_active Expired
- 1975-05-27 ZA ZA00753433A patent/ZA753433B/xx unknown
- 1975-05-28 DE DE19752523704 patent/DE2523704A1/de not_active Withdrawn
- 1975-05-28 ES ES437977A patent/ES437977A1/es not_active Expired
- 1975-05-28 IT IT23858/75A patent/IT1038564B/it active
- 1975-05-29 NO NO751906A patent/NO140619C/no unknown
- 1975-05-30 BE BE156895A patent/BE829720A/fr unknown
- 1975-05-30 FR FR7517017A patent/FR2275234A1/fr active Granted

Also Published As

Publication number	Publication date
ES437977A1 (es)	1977-01-16
NO751906L (fr)	1975-12-02
GB1505722A (en)	1978-03-30
FR2275234A1 (fr)	1976-01-16
BE829720A (fr)	1975-12-01
ZA753433B (en)	1976-04-28
NO140619B (no)	1979-07-02
NO140619C (no)	1979-10-10
FR2275234B1 (fr)	1980-05-23
DE2523704A1 (de)	1975-12-04
IT1038564B (it)	1979-11-30

Publication	Publication Date	Title
US4053369A (en)	1977-10-11	Extractive distillation
US3723256A (en)	1973-03-27	Aromatic hydrocarbon recovery by extractive distillation, extraction and plural distillations
US5849982A (en)	1998-12-15	Recovery of styrene from pyrolysis gasoline by extractive distillation
US5399244A (en)	1995-03-21	Process to recover benzene from mixed hydrocarbons by extractive distillation
US5354430A (en)	1994-10-11	Staged purification of contaminated propylene oxide
US4401517A (en)	1983-08-30	Vapor-liquid extractive distillation with dialkyl sulfone/water combination
GB1582146A (en)	1980-12-31	Polar hydrocarbon extraction with solvent recovery and regeneration
US4948470A (en)	1990-08-14	Extractive distillation of alkane/cycloalkane feed employing mixed solvent
USRE26255E (en)	1967-08-29	Recovery of aromatics
EP1280869A2 (fr)	2003-02-05	Purification d'elements aromatiques issus d'ecoulements de petrole
US3338824A (en)	1967-08-29	Water-washing raffinate to recover the sulfolane solvent
US5262017A (en)	1993-11-16	Plural stage purification of propylene oxide
CA1077967A (fr)	1980-05-20	Production de benzene par extraction de solvant et hydroalkylation
US3642614A (en)	1972-02-15	Reduction of soluble contaminants in lean solvent
CA1053601A (fr)	1979-05-01	Distillation extractive
US2831905A (en)	1958-04-22	Gamma-butyrolactone as a selective solvent for hydrocarbons
US3844902A (en)	1974-10-29	Combination of extractive distillation and liquid extraction process for separation of a hydrocarbon feed mixture
US3763037A (en)	1973-10-02	Aromatic hydrocarbon
US5073669A (en)	1991-12-17	Method for aromatic hydrocarbon recovery
US2711433A (en)	1955-06-21	Process for extraction and recovery of aromatic hydrocarbons from hydrocarbon mixtures
US3544453A (en)	1970-12-01	Process for the extraction and recovery of aromatic hydrocarbons
US3435087A (en)	1969-03-25	Recovery of aromatics
EP0645381B1 (fr)	1997-11-12	Procédé multi-étapes de séchage et purification de l'oxyde de propylène
US3883420A (en)	1975-05-13	Edible oil solvent production
US4083772A (en)	1978-04-11	Aromatic hydrocarbon separation process