TW201247301A - Extractive distillation of crude alcohol product - Google Patents

Extractive distillation of crude alcohol product Download PDF

Info

Publication number: TW201247301A
Authority: TW; Taiwan
Prior art keywords: ethanol; acetic acid; residue; stream; water
Prior art date: 2011-04-26

Application number

TW101114975A

Other languages

English (en)

Chinese (zh)

Inventor

R Jay Warner

Victor J Johnston

David Lee

Adam Orosco

Original Assignee

Celanese Int Corp

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.)

2011-04-26

Filing date

2012-04-26

Publication date

2012-12-01

2011-04-26 Priority claimed from US13/094,588 external-priority patent/US8686200B2/en

2011-06-16 Priority claimed from US13/162,034 external-priority patent/US8748675B2/en

2012-04-26 Application filed by Celanese Int Corp filed Critical Celanese Int Corp

2012-12-01 Publication of TW201247301A publication Critical patent/TW201247301A/zh

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 618
238000000895 extractive distillation Methods 0.000 title abstract description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 501
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 221
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 124
238000004821 distillation Methods 0.000 claims description 94
239000000047 product Substances 0.000 claims description 70
238000000034 method Methods 0.000 claims description 62
239000002253 acid Substances 0.000 claims description 52
230000008569 process Effects 0.000 claims description 51
239000000203 mixture Substances 0.000 claims description 41
239000000052 vinegar Substances 0.000 claims description 19
235000021419 vinegar Nutrition 0.000 claims description 19
-1 diamine oxime Chemical class 0.000 claims description 18
238000005886 esterification reaction Methods 0.000 claims description 12
230000032050 esterification Effects 0.000 claims description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
239000012043 crude product Substances 0.000 claims description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
229920001223 polyethylene glycol Polymers 0.000 claims description 4
239000002202 Polyethylene glycol Substances 0.000 claims description 3
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 2
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 1
239000001273 butane Substances 0.000 claims 1
238000005660 chlorination reaction Methods 0.000 claims 1
238000010899 nucleation Methods 0.000 claims 1
BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 claims 1
238000005984 hydrogenation reaction Methods 0.000 abstract description 25
238000011084 recovery Methods 0.000 abstract description 11
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract description 2
235000019441 ethanol Nutrition 0.000 description 206
238000010025 steaming Methods 0.000 description 87
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
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239000003054 catalyst Substances 0.000 description 32
238000000926 separation method Methods 0.000 description 31
239000007789 gas Substances 0.000 description 26
238000004519 manufacturing process Methods 0.000 description 24
239000007788 liquid Substances 0.000 description 23
239000000463 material Substances 0.000 description 22
239000001257 hydrogen Substances 0.000 description 20
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229910052751 metal Inorganic materials 0.000 description 20
239000002184 metal Substances 0.000 description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
238000000855 fermentation Methods 0.000 description 11
239000012071 phase Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
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239000006227 byproduct Substances 0.000 description 7
239000012528 membrane Substances 0.000 description 7
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241000282320 Panthera leo Species 0.000 description 6
238000009835 boiling Methods 0.000 description 6
229910002091 carbon monoxide Inorganic materials 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
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229910044991 metal oxide Inorganic materials 0.000 description 6
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238000007254 oxidation reaction Methods 0.000 description 6
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 5
150000001241 acetals Chemical class 0.000 description 5
239000001569 carbon dioxide Substances 0.000 description 5
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229910052802 copper Inorganic materials 0.000 description 5
239000010949 copper Substances 0.000 description 5
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150000002430 hydrocarbons Chemical class 0.000 description 5
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238000000746 purification Methods 0.000 description 5
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238000000066 reactive distillation Methods 0.000 description 5
239000002028 Biomass Substances 0.000 description 4
244000025254 Cannabis sativa Species 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
229930182558 Sterol Natural products 0.000 description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
238000007664 blowing Methods 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
238000010586 diagram Methods 0.000 description 4
229910052742 iron Inorganic materials 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
239000003345 natural gas Substances 0.000 description 4
230000000737 periodic effect Effects 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
241000894007 species Species 0.000 description 4
150000003432 sterols Chemical class 0.000 description 4
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BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 4
229910052718 tin Inorganic materials 0.000 description 4
IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
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240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
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150000001242 acetic acid derivatives Chemical class 0.000 description 3
RFQIWHDNNZFRBL-UHFFFAOYSA-N acetic acid;ethanol;hydrate Chemical compound O.CCO.CC(O)=O RFQIWHDNNZFRBL-UHFFFAOYSA-N 0.000 description 3
UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 3
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229910052918 calcium silicate Inorganic materials 0.000 description 3
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OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)

TW101114975A 2011-04-26 2012-04-26 Extractive distillation of crude alcohol product TW201247301A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US13/094,588 US8686200B2 (en)	2011-04-26	2011-04-26	Process to recover alcohol from an acidic residue stream
US13/162,034 US8748675B2 (en)	2011-06-16	2011-06-16	Extractive distillation of crude alcohol product
US201161566442P	2011-12-02	2011-12-02

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Publication Number	Publication Date
TW201247301A true TW201247301A (en)	2012-12-01

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Country Status (7)

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EP (1)	EP2702026A1 (fr)
CN (1)	CN103270010B (fr)
AR (1)	AR086129A1 (fr)
BR (1)	BR112013027348A2 (fr)
MX (1)	MX2013012539A (fr)
TW (1)	TW201247301A (fr)
WO (1)	WO2012149148A1 (fr)

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2012
- 2012-04-26 MX MX2013012539A patent/MX2013012539A/es not_active Application Discontinuation
- 2012-04-26 WO PCT/US2012/035196 patent/WO2012149148A1/fr not_active Ceased
- 2012-04-26 TW TW101114975A patent/TW201247301A/zh unknown
- 2012-04-26 BR BR112013027348A patent/BR112013027348A2/pt not_active IP Right Cessation
- 2012-04-26 AR ARP120101469 patent/AR086129A1/es not_active Application Discontinuation
- 2012-04-26 EP EP12720331.3A patent/EP2702026A1/fr not_active Withdrawn
- 2012-04-26 CN CN201280003019.0A patent/CN103270010B/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP2702026A1 (fr)	2014-03-05
MX2013012539A (es)	2013-12-02
AR086129A1 (es)	2013-11-20
CN103270010A (zh)	2013-08-28
CN103270010B (zh)	2016-01-20
BR112013027348A2 (pt)	2017-01-17
WO2012149148A1 (fr)	2012-11-01

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