JPH0351696B2 - - Google Patents
Info
- Publication number
- JPH0351696B2 JPH0351696B2 JP56184533A JP18453381A JPH0351696B2 JP H0351696 B2 JPH0351696 B2 JP H0351696B2 JP 56184533 A JP56184533 A JP 56184533A JP 18453381 A JP18453381 A JP 18453381A JP H0351696 B2 JPH0351696 B2 JP H0351696B2
- Authority
- JP
- Japan
- Prior art keywords
- acetaldehyde
- column
- methanol
- methyl acetate
- mixture
- Prior art date
- 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 - Lifetime
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 78
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 32
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 22
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 22
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 150000005527 organic iodine compounds Chemical class 0.000 claims description 11
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 150000002497 iodine compounds Chemical class 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 239000011260 aqueous acid Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 230000000630 rising effect Effects 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 3
- 238000000354 decomposition reaction Methods 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 26
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000011905 homologation Methods 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000003889 chemical engineering Methods 0.000 description 2
- 229940011182 cobalt acetate Drugs 0.000 description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 238000007163 homologation reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 238000005852 acetolysis reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001868 cobalt Chemical class 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
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/84—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by azeotropic distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803045105 DE3045105A1 (de) | 1980-11-29 | 1980-11-29 | Verfahren zur abtrennung organischer jod-verbindungen von acetaldehyd |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57120544A JPS57120544A (en) | 1982-07-27 |
| JPH0351696B2 true JPH0351696B2 (en, 2012) | 1991-08-07 |
Family
ID=6117937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56184533A Granted JPS57120544A (en) | 1980-11-29 | 1981-11-19 | Separation of organic iodine compound from acetaldehyde |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4383894A (en, 2012) |
| EP (1) | EP0053245B1 (en, 2012) |
| JP (1) | JPS57120544A (en, 2012) |
| CA (1) | CA1172988A (en, 2012) |
| DE (2) | DE3045105A1 (en, 2012) |
| ES (1) | ES8207113A1 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1327077C (zh) * | 2004-08-31 | 2007-07-18 | 苏州宝富塑料制品有限公司 | 晒衣杆支撑架 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3107731A1 (de) * | 1981-02-28 | 1982-09-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur abtrennung organischer jod-verbindungen von carbonylierungsprodukten des methanols, methylacetates und dimethylethers |
| US12162830B2 (en) * | 2019-04-01 | 2024-12-10 | Celanese International Corporation | Aldehyde removal process for methanol carbonylation |
| WO2021202270A1 (en) * | 2020-04-01 | 2021-10-07 | Celanese International Corporation | Processes for removing and/or reducing permanganate reducing compounds and alkyl iodides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA593719A (en) * | 1960-03-01 | L. Aldridge Clyde | Aldehyde purification | |
| US3062889A (en) * | 1962-11-06 | Process for purifying acetaldehyde | ||
| US2452797A (en) * | 1944-05-29 | 1948-11-02 | Us Ind Chemicals Inc | Stripping of acetaldehyde from aldol by hydrocarbon vapors |
| US2707165A (en) * | 1952-06-24 | 1955-04-26 | Celanese Corp | Purification of aldehydes |
-
1980
- 1980-11-29 DE DE19803045105 patent/DE3045105A1/de not_active Withdrawn
-
1981
- 1981-10-12 DE DE8181108200T patent/DE3161560D1/de not_active Expired
- 1981-10-12 EP EP81108200A patent/EP0053245B1/de not_active Expired
- 1981-10-29 US US06/316,301 patent/US4383894A/en not_active Expired - Fee Related
- 1981-11-03 CA CA000389309A patent/CA1172988A/en not_active Expired
- 1981-11-19 JP JP56184533A patent/JPS57120544A/ja active Granted
- 1981-11-27 ES ES507520A patent/ES8207113A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1327077C (zh) * | 2004-08-31 | 2007-07-18 | 苏州宝富塑料制品有限公司 | 晒衣杆支撑架 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES507520A0 (es) | 1982-09-01 |
| JPS57120544A (en) | 1982-07-27 |
| DE3161560D1 (en) | 1984-01-05 |
| DE3045105A1 (de) | 1982-07-01 |
| ES8207113A1 (es) | 1982-09-01 |
| EP0053245B1 (de) | 1983-11-30 |
| US4383894A (en) | 1983-05-17 |
| CA1172988A (en) | 1984-08-21 |
| EP0053245A1 (de) | 1982-06-09 |
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