TW201325723A - 使用碘化氫及醋酸之水溶液的觸媒回收法 - Google Patents

使用碘化氫及醋酸之水溶液的觸媒回收法 Download PDF

Info

Publication number: TW201325723A
Authority: TW; Taiwan
Prior art keywords: tar; acetic acid; catalyst; aqueous; location
Prior art date: 2011-12-28

Application number

TW101131070A

Other languages

English (en)

Chinese (zh)

Inventor

Bradley Alan Steinhoff

Chad Moore

Original Assignee

Eastman Chem 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.)

2011-12-28

Filing date

2012-08-27

Publication date

2013-07-01

2012-08-27 Application filed by Eastman Chem Co filed Critical Eastman Chem Co

2013-07-01 Publication of TW201325723A publication Critical patent/TW201325723A/zh

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 416
239000003054 catalyst Substances 0.000 title claims abstract description 124
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 title claims abstract description 40
229910000043 hydrogen iodide Inorganic materials 0.000 title claims abstract description 39
238000011084 recovery Methods 0.000 title claims description 24
239000007788 liquid Substances 0.000 claims abstract description 93
238000000034 method Methods 0.000 claims abstract description 74
239000007864 aqueous solution Substances 0.000 claims abstract description 43
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 79
239000008346 aqueous phase Substances 0.000 claims description 49
239000012074 organic phase Substances 0.000 claims description 41
229910052740 iodine Inorganic materials 0.000 claims description 37
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 35
239000011630 iodine Substances 0.000 claims description 34
239000000243 solution Substances 0.000 claims description 26
229910052751 metal Inorganic materials 0.000 claims description 21
239000002184 metal Substances 0.000 claims description 21
239000010948 rhodium Substances 0.000 claims description 16
239000000463 material Substances 0.000 claims description 7
150000002739 metals Chemical class 0.000 claims description 5
229910052703 rhodium Inorganic materials 0.000 claims description 5
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
239000011269 tar Substances 0.000 description 147
238000000605 extraction Methods 0.000 description 84
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
239000000203 mixture Substances 0.000 description 42
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 37
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 34
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 30
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 30
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 21
238000005810 carbonylation reaction Methods 0.000 description 17
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 16
230000006315 carbonylation Effects 0.000 description 16
239000010410 layer Substances 0.000 description 16
229910052707 ruthenium Inorganic materials 0.000 description 16
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
230000000052 comparative effect Effects 0.000 description 8
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 8
238000012545 processing Methods 0.000 description 8
230000003197 catalytic effect Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000008901 benefit Effects 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000006227 byproduct Substances 0.000 description 5
239000000523 sample Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
229910003460 diamond Inorganic materials 0.000 description 4
239000010432 diamond Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
230000001186 cumulative effect Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052741 iridium Inorganic materials 0.000 description 3
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052704 radon Inorganic materials 0.000 description 3
SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000011144 upstream manufacturing Methods 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
150000001845 chromium compounds Chemical class 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002642 lithium compounds Chemical class 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910052762 osmium Inorganic materials 0.000 description 2
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
150000003304 ruthenium compounds Chemical class 0.000 description 2
229910052712 strontium Inorganic materials 0.000 description 2
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000012327 Ruthenium complex Substances 0.000 description 1
LEKJTGQWLAUGQA-UHFFFAOYSA-N acetyl iodide Chemical compound CC(I)=O LEKJTGQWLAUGQA-UHFFFAOYSA-N 0.000 description 1
238000010923 batch production Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000000571 coke Substances 0.000 description 1
239000012468 concentrated sample Substances 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000011143 downstream manufacturing Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000002816 nickel compounds Chemical class 0.000 description 1
-1 nitrogen-containing compound Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
230000009182 swimming Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
- B01J38/60—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using acids
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/96—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the noble metals
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
- B01J38/60—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using acids
- B01J38/62—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using acids organic
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/464—Rhodium

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

TW101131070A 2011-12-28 2012-08-27 使用碘化氫及醋酸之水溶液的觸媒回收法 TW201325723A (zh)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US201161580759P	2011-12-28	2011-12-28

Publications (1)

Publication Number	Publication Date
TW201325723A true TW201325723A (zh)	2013-07-01

Family

ID=48698255

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW101131070A TW201325723A (zh)	2011-12-28	2012-08-27	使用碘化氫及醋酸之水溶液的觸媒回收法

Country Status (5)

Country	Link
EP (1)	EP2797694A4 (fr)
JP (1)	JP5894297B2 (fr)
CN (1)	CN104023848A (fr)
TW (1)	TW201325723A (fr)
WO (1)	WO2013101015A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9302975B1 (en) *	2015-07-01	2016-04-05	Celanese International Corporation	Process for flashing a reaction medium
US9302974B1 (en) *	2015-07-01	2016-04-05	Celanese International Corporation	Process for producing acetic acid
JP7128965B2 (ja) *	2018-12-21	2022-08-31	エルジー・ケム・リミテッド	表面改質処理による廃有機亜鉛触媒の再生方法
CN119614887B (zh) *	2024-12-20	2025-09-02	河南龙宇煤化工有限公司	低压甲醇羰基化合成醋酸工艺中贵金属催化剂的回收方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4388217A (en) *	1980-11-24	1983-06-14	Eastman Kodak Company	Process for the recovery of catalyst values
EP0064989B1 (fr) *	1980-11-24	1986-06-18	EASTMAN KODAK COMPANY (a New Jersey corporation)	Procede de recuperation d'un catalyseur de rhodium
US4578368A (en) *	1985-05-06	1986-03-25	Eastman Kodak Company	Catalyst recovery process
GB8618710D0 (en) *	1986-07-31	1986-09-10	Bp Chem Int Ltd	Recovering metals
DE68921224T2 (de) *	1989-11-20	1995-06-14	Eastman Chem Co	Verfahren zur wiedergewinnung von katalysatorwerten.
US5100850A (en) *	1991-05-03	1992-03-31	Eastman Kodak Company	Oxidative secondary rhodium recovery process
US5420088A (en) *	1993-01-26	1995-05-30	Battelle Memorial Institute	Electrochemical catalyst recovery method
US6046125A (en) *	1998-04-06	2000-04-04	Coastal Catalyst Technology, Inc.	Methods for enhancing the acid sites of FCC catalysts

2011
- 2011-12-29 EP EP11879116.9A patent/EP2797694A4/fr not_active Withdrawn
- 2011-12-29 JP JP2014550257A patent/JP5894297B2/ja not_active Expired - Fee Related
- 2011-12-29 CN CN201180076028.8A patent/CN104023848A/zh active Pending
- 2011-12-29 WO PCT/US2011/067702 patent/WO2013101015A1/fr not_active Ceased
2012
- 2012-08-27 TW TW101131070A patent/TW201325723A/zh unknown

Also Published As

Publication number	Publication date
JP2015507535A (ja)	2015-03-12
EP2797694A4 (fr)	2015-10-14
WO2013101015A1 (fr)	2013-07-04
EP2797694A1 (fr)	2014-11-05
JP5894297B2 (ja)	2016-03-23
CN104023848A (zh)	2014-09-03

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