TW201609632A - 用於c8芳香族混合物之分離製程 - Google Patents
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- TW201609632A TW201609632A TW104127868A TW104127868A TW201609632A TW 201609632 A TW201609632 A TW 201609632A TW 104127868 A TW104127868 A TW 104127868A TW 104127868 A TW104127868 A TW 104127868A TW 201609632 A TW201609632 A TW 201609632A
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- ethylbenzene
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- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 238000000926 separation method Methods 0.000 title claims description 11
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 32
- 238000004821 distillation Methods 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 27
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims description 19
- 238000000605 extraction Methods 0.000 claims description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 10
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 claims description 4
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims description 4
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 4
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 4
- BDJAEZRIGNCQBZ-UHFFFAOYSA-N methylcyclobutane Chemical compound CC1CCC1 BDJAEZRIGNCQBZ-UHFFFAOYSA-N 0.000 claims description 4
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 claims description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 3
- 229940078552 o-xylene Drugs 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- -1 polychlorobenzenes Chemical compound 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 claims description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 2
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 claims description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims description 2
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 2
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- 229960001047 methyl salicylate Drugs 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 claims 2
- SYTQFBVTZCYXOV-UHFFFAOYSA-N 3,5,5-trimethylcyclohex-2-en-1-one Chemical compound CC1=CC(=O)CC(C)(C)C1.CC1=CC(=O)CC(C)(C)C1 SYTQFBVTZCYXOV-UHFFFAOYSA-N 0.000 claims 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 claims 1
- 238000007700 distillative separation Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 150000003738 xylenes Chemical class 0.000 description 6
- 238000000895 extractive distillation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical group CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N 3-methyl-2-pentanone Chemical compound CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MHVRVZYTOYAHNI-UHFFFAOYSA-N 2,5,7,10-tetramethylundecan-6-one Chemical compound CC(CCC(C)C)C(=O)C(CCC(C)C)C MHVRVZYTOYAHNI-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000005194 ethylbenzenes Chemical class 0.000 description 1
- PWVDFPINYKVAFM-UHFFFAOYSA-N fluoren-4-one Chemical compound C1=CC=CC2=C3C(=O)C=CC=C3C=C21 PWVDFPINYKVAFM-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
Classifications
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- 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
-
- 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
-
- 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
- B01D3/36—Azeotropic distillation
-
- 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
- B01D3/38—Steam distillation
-
- 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
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- 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
- 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
- C07C7/06—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by azeotropic distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一種用於自一包含乙苯與至少一種其他C8芳香族化合物之混合物中蒸餾分離乙苯的製程,包含將該混合物在一萃取溶劑存在下於一蒸餾塔中蒸餾,其特徵在於該蒸餾塔係於一低大氣壓力下操作。
Description
本發明係關於一種藉由蒸餾分離自一包含乙苯與至少一種其他C8芳香族化合物之混合物中分離乙苯的製程。
乙苯係一種具有高經濟利用與價值的烴類化合物。其主要用途為製造苯乙烯,而苯乙烯為製造聚苯乙烯的一中間物。乙苯係由苯與乙烯的烷化反應而商業製造。然而,乙烯與苯的成本與競爭需求促使了對於自以含有乙苯的多種C8芳香族進料流中回收乙苯的新嘗試。該等進料流通常為數種石化製程的副產物流,且通常含有一或多種沸點與乙苯的沸點相近的烴類化合物,尤其是C8芳香族異構物。
已知有自其他沸點相近的C8芳香族化合物中,尤其是二甲苯異構物中,分離乙苯的方法。
舉例而言,美國專利第3,917,734號揭露一種用於自包含乙苯及至少一種二甲苯異構物的進料混合物中分離乙苯的吸附分離製程,該製程包含將該進料混合物與晶性鋁矽酸鹽吸附劑接觸以選擇性吸附二甲苯異構物並實質排除吸附乙苯,以及其後回收純化的乙苯作為產物。此製成的分離效率主要依賴吸附劑的吸附容量,且因此較佳使用逆流移動床系統的複雜操作。並且,
在進料流中的雜質含量需要謹慎控制,以避免干擾選擇性吸附製程。
當然,乙苯可藉由分餾自二甲苯異構物中分離,但由於其彼此沸點非常接近,分餾僅能以更為複雜且能量密集的系統達成。
英國專利第1,198,592號揭露一種使用單一多功能蒸餾塔以分離C8芳香族異構物的製程。該蒸餾係於具有至少250且較佳365個板(tray)的多板塔(multiplate column)中以迴流比100至250:1進行,以達成商業上可接受純度的乙苯。
萃取蒸餾為將沸點相近的化合物彼此分離的方法,其藉由在添加的溶劑,或所謂萃取劑的存在下進行蒸餾。該等萃取劑在蒸餾系統中的存在改變了相對揮發度,且因此使沸點相近的化合物之較大分離程度成為可能。
美國專利第3,105,017號揭露一種用於自二甲苯異構物中分離乙苯的製程,藉由將該混合物在一含有單一苯環且環上至少兩個位置被氯基取代的化合物存在下,於條件下萃取蒸餾以分離一富含乙苯的餾分。
本發明涉及一種用於製造乙苯之替代的且改進的製程,其藉由將乙苯由烴類混合物物流中回收。該製程包含將包含乙苯與至少一種其他C8芳香族化合物之混合物在一萃取溶劑存在下且於一低大氣壓力(sub-atmospheric pressure)操作下於蒸餾塔中蒸餾。
本發明係關於一種用於分離乙苯的萃取蒸餾製程,包含將包含乙苯與至少一種其他C8芳香族化合物之混合物在一萃取溶劑存在下且於一低大氣壓力操作下於蒸餾塔中蒸餾。
主要包含C8烴類化合物的烴類物流中經常含有乙苯。根據本發明的製程可以有效將乙苯自與之沸點相近的混合物中分離,尤其是C8芳香族化合物。在本發明一實施態樣中,該至少一種其他C8芳香族化合物包含選自對二甲苯、間二甲苯、鄰二甲苯及其混合物的化合物。該混合物可進一步包含其他組分,尤其是C5至C10範圍的烴類,且芳香族及非芳香族的種類皆含在內。舉例而言,該混合物可含有小量的苯、甲苯、及C5至C10石蠟、烯烴類、或萘類。混合物中的該等其他組分較佳少於20重量%,更佳少於15重量%,甚至更佳少於10重量%,且最佳少於5重量%。
可用作為萃取溶劑的溶劑應能夠改變目標系統中的相對揮發度。此外,其應與進料流中的組分具有適當的沸點差距,以使其可方便地回收並重複使用。適合本發明的萃取溶劑具有高於150℃的沸點,更佳為151至290℃。多種有機化合物適格作為本發明的萃取溶劑。在一實施態樣中,萃取溶劑包含一有機化合物,選自含有Cl之化合物、含有S之化合物、含有N之化合物、含有O之化合物、及其混合物。
該含有Cl之化合物可選自2,4-二氯苯、1,2,4-三氯苯、1,2,4,5-四氯苯、多氯苯(polychlorobenzenes)、六氯苯、2,3,4,6-四氯酚、1,2,3-三氯丙烷、及其混合物,較佳1,2,3-三氯苯及1,2,4-
三氯苯。
該含有S的化合物較佳係選自二甲亞碸(dimethylsulfoxide)、環丁碸(sulfolane)、甲基環丁碸、及其混合物。
該含有N的化合物較佳係選自N-甲醯嗎啉(N-formylmorpholine)、苯胺、2-吡咯啶酮(2-pyrolidinone)、喹啉酮(quinolone)、N-甲基-2-吡咯啶酮(N-methyl-2-pyrrolidone)、N-甲基苯胺、苄腈、硝基苯、及其混合物。
該含有O之化合物係選自柳酸甲酯、苯甲酸甲酯、N-甲基-2-吡咯啶酮、1,2-丙二醇、1,2-丁二醇、1,3-丁二醇、苯甲醛、酚、四氫呋喃甲醇(tetrahydrofurfuryl alcohol)、馬來酸二乙酯、乙醯乙酸乙酯、4-甲氧基苯乙酮、異佛酮(isophorone)、5-甲基-2-己酮、2-庚酮、環己酮、2-辛酮、2-壬酮、3-庚酮、二異丁酮、5-壬酮、苄醇、及其混合物。
萃取溶劑較佳包含含有Cl之化合物。更佳地,萃取溶劑包含含有Cl之化合物,其係選自1,2,3-三氯苯及1,2,4-三氯苯,最佳1,2,4-三氯苯。
已令人驚訝地發現,根據本發明將蒸餾塔的操作壓力減低至低大氣壓層級可顯著改進分離乙苯的效率。特定而言,令人驚訝地發現在低大氣壓下操作蒸餾塔可達成自包含乙苯及至少一種其他C8芳香族化合物的混合物中分離乙苯的高分離效率。然而,太低的真空壓力將導致超高蒸汽流速且因此降低塔的填充或板效率。在一實施態樣中,該低大氣壓力係10至900毫巴範圍,較佳50至500毫巴,更佳100至300毫巴。
蒸餾塔於由塔頂部至底部分布的溫度下操作,該溫度使得較易揮發的餾分(於此情況下為乙苯)得以於塔中向上蒸餾,而較不易揮發的餾分得以向下蒸餾,導致理想分離的結果。在一較佳實施態樣中,蒸餾塔於50至250℃溫度範圍下操作,較佳60至200℃,更佳70至180℃。
該萃取溶劑與該包含乙苯與至少一種其他C8芳香族化合物之混合物於蒸餾塔中的質量比較佳係1:1至10:1之範圍,較佳2:1至8:1,且最佳3:1至7:1。
較佳地,本發明製程可於一含水環境下操作。為創造含水環境,水及/或蒸汽可被加入蒸餾塔中,較佳基於所使用的該萃取溶劑之流量(mass flow),該水及/或蒸汽以0.1至25重量%的用量添加。
在某些實施態樣中,可採用額外溶劑,藉由引入蒸餾塔中,進一步改變乙苯與需分離的沸點相近組分的相對揮發度。額外溶劑可選自含有Cl之化合物、含有S之化合物、含有N之化合物、含有O之化合物、或其混合物。較佳地,該額外溶劑係選自由以下所組成之群組:氯仿、四氯化碳、二甲胺、二乙胺、乙腈、乙醛、1-丙醛、甲基異丙基酮、3-甲基-2-戊酮、3,3-二甲基-2-丁酮、2-戊酮、2-甲基丙醛、1-丁醛、環戊酮、丙酮、乙醇、及其混合物。通常,該額外溶劑與該包含乙苯及至少一種其他C8芳香族化合物的混合物同時被引入蒸餾塔中。
本發明的一具體實施態樣可進一步涉及將相對於進入蒸餾塔的混合物而言為富含乙苯的頂部流,由蒸餾塔的上方部分抽出。此富含乙苯的流可直接輸送至需要乙苯作為原料的下游
製程。在更特定的情況下,富含乙苯的流可在進入某些需要更為純化的乙苯的下游工業製程之前進行進一步處理,例如進一步純化。在一較佳實施態樣中,至少部分的富含乙苯的頂部流被濃縮並作為迴流送回蒸餾塔。根據所採用的操作條件,頂部流中的乙苯濃度可相當廣。
本發明製程亦可進一步涉及將底部流由蒸餾塔的下方部分抽出。此底部流較佳為貧乙苯的(ethylbenzene lean),且主要包含萃取溶劑及較乙苯重的C8芳香族化合物。較佳地,底部流經過後續分離單元,以自此物流回收萃取溶劑並製造C8芳香族產物。所回收的萃取溶劑之後於蒸餾塔中再利用。在特定的實施態樣中,其中C8芳香族化合物包含顯著部分的對二甲苯,當使用最佳化的操作條件時,C8芳香族產物可含有少於20重量%的乙苯,且可進一步作為混合二甲苯異構物等級而利用。
本發明亦關於一種低大氣壓力於一蒸餾塔中自一包含乙苯與至少一種其他C8芳香族化合物之混合物蒸餾分離該乙苯的製程中之用途,其係用於增加該分離的效率,使得可降低例如迴流比(reflux ratio)。
將進一步以下列實施例例示本發明實施態樣,但不限制發明之申請專利範圍。
實施例1
電腦模擬係使用模擬軟體「Aspen HYSYS®」進行,模擬含有64.93重量%乙苯、7.9重量%對二甲苯、18.14重量%間二甲苯、及9.02重量%鄰二甲苯的進料流以進料速率15000公斤
/小時進料至具有130個塔板(stage)的萃取蒸餾塔中。如表1所示的多種萃取溶劑在塔板7被引入萃取蒸餾塔中,即,在進料流於塔板74引入的點的上方。作為比較實施例,進行沒有引入溶劑的模擬。塔的操作溫度模擬為75℃至175℃範圍。塔中壓力分別模擬為200毫巴及1000毫巴(見下表1)。溶劑與進料流的重量比固定為5:1。模擬模型進一步包括富乙苯物流由塔頂抽出且貧乙苯物流由塔底抽出的特徵。部分來自塔頂的富乙苯物流模擬為作為迴流回到塔中,迴流比為8.5。
由表1可見,將蒸餾塔中壓力由1000毫巴降低至200毫巴,即降至低大氣壓力時,製成的分離效率被改進。具體而言,即使沒有使用溶劑,當塔中壓力降低,頂部流中的乙苯濃度即顯著上升。
在以下表1中,TCB係1,2,4-三氯苯,NMP係N-甲基-2-吡咯啶酮,且NFM係N-甲醯嗎啉。
Claims (15)
- 一種用於自一包含乙苯與至少一種其他C8芳香族化合物之混合物中蒸餾分離乙苯的製程,包含將該混合物在一萃取溶劑存在下於一蒸餾塔中蒸餾,其特徵在於該蒸餾塔係於一低大氣壓力(sub-atmospheric pressure)下操作。
- 如請求項1所述之製程,其中該萃取溶劑係具有高於150℃之沸點。
- 如請求項1或2所述之製程,其中該萃取溶劑包含選自如下之一有機化合物:含有Cl之化合物、含有S之化合物、含有N之化合物、含有O之化合物、及其混合物。
- 如請求項3所述之製程,其中該含有Cl之化合物係選自2,4-二氯苯、1,2,3-三氯苯、1,2,4-三氯苯、1,2,4,5-四氯苯、多氯苯(polychlorobenzenes)、六氯苯、2,3,4,6-四氯酚、1,2,3-三氯丙烷。
- 如請求項3所述之製程,其中該含有S之化合物係選自二甲亞碸(dimethylsulfoxide)、環丁碸(sulfolane)、甲基環丁碸、及其混合物。
- 如請求項3所述之製程,其中該含有N之化合物係選自N-甲醯嗎啉(N-formylmorpholine)、苯胺、2-吡咯啶酮(2-pyrolidinone)、喹啉酮(quinolone)、N-甲基-2-吡咯啶酮(N-methyl-2-pyrrolidone)、N-甲基苯胺、苄腈、硝基苯、及其混合物。
- 如請求項3所述之製程,其中該含有O之化合物係選自柳酸甲酯、苯甲酸甲酯、N-甲基-2-吡咯啶酮、1,2-丙二醇、1,2- 丁二醇、1,3-丁二醇、苯甲醛、酚、四氫呋喃甲醇(tetrahydrofurfuryl alcohol)、馬來酸二乙酯、乙醯乙酸乙酯、4-甲氧基苯乙酮、異佛酮(isophorone)、5-甲基-2-己酮、2-庚酮、環己酮、2-辛酮、2-壬酮、3-庚酮、二異丁酮、5-壬酮、苄醇、及其混合物。
- 如請求項1或2所述之製程,其中該低大氣壓力係10至900毫巴範圍。
- 如請求項8所述之製程,其中該低大氣壓力係50至600毫巴範圍。
- 如請求項1或2所述之製程,其中該蒸餾塔係於50至250℃溫度範圍下操作。
- 如請求項1或2所述之製程,其中該萃取溶劑與該包含乙苯與至少一種其他C8芳香族化合物之混合物的質量比係1:1至10:1範圍。
- 如請求項1或2所述之製程,其中該至少一種其他C8芳香族化合物包含選自如下之一化合物:對二甲苯、間二甲苯、鄰二甲苯、或其混合物。
- 如請求項1或2所述之製程,其中該製程包含將水及/或蒸汽加入該蒸餾塔。
- 如請求項13所述之製程,其中基於所使用的該萃取溶劑之流量(mass flow),該水及/或蒸汽係以0.1至25重量%的用量添加。
- 一種低大氣壓力於一蒸餾塔中自一包含乙苯與至少一種其他C8芳香族化合物之混合物蒸餾分離該乙苯的製程中之用途, 其係用於增加該分離的效率。
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US2532031A (en) * | 1948-04-06 | 1950-11-28 | Shell Dev | Separation of c8h10 aromatic hydrocarbons by extractive distillation |
US3105017A (en) * | 1960-06-22 | 1963-09-24 | Exxon Research Engineering Co | Extractive distillation of ethylbenzene |
US3522153A (en) | 1968-04-04 | 1970-07-28 | Badger Co | Method of separating xylene isomers by distillation with crystallization and isomerization of a side stream |
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US3917734A (en) | 1974-04-08 | 1975-11-04 | Universal Oil Prod Co | Process for the separation of ethylbenzene |
IT1063231B (it) * | 1976-01-14 | 1985-02-11 | Snam Progetti | Impiego di n-metil-morfolin-3-one quale solvente per la separazione di idrocarburi |
US4283587A (en) * | 1980-06-16 | 1981-08-11 | Uop Inc. | Adsorptive separation of aromatic isomers |
US4299668A (en) | 1981-02-23 | 1981-11-10 | International Synthetic Rubber Co., Ltd. | Separation of ethylbenzene from para- and meta-xylenes by extractive distillation |
US5135620A (en) * | 1991-09-04 | 1992-08-04 | Phillips Petroleum Company | Separation of ethylbenzene from xylenes by extractive distillation |
US5425855A (en) * | 1994-04-08 | 1995-06-20 | Lloyd Berg | Separation of ethyl benzene from p-xylene by extractive distillation |
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