CA1171812A - Process for the isolation of monochloroacetaldehyde - Google Patents
Process for the isolation of monochloroacetaldehydeInfo
- Publication number
- CA1171812A CA1171812A CA000374936A CA374936A CA1171812A CA 1171812 A CA1171812 A CA 1171812A CA 000374936 A CA000374936 A CA 000374936A CA 374936 A CA374936 A CA 374936A CA 1171812 A CA1171812 A CA 1171812A
- Authority
- CA
- Canada
- Prior art keywords
- chloroacetaldehyde
- column
- acetaldehyde
- distillation
- containing fraction
- 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
Links
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000002955 isolation Methods 0.000 title claims abstract description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000004821 distillation Methods 0.000 claims abstract description 19
- 238000000605 extraction Methods 0.000 claims abstract description 10
- 238000000746 purification Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims abstract description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005977 Ethylene Substances 0.000 claims abstract description 7
- 239000006286 aqueous extract Substances 0.000 claims abstract description 6
- 239000006227 byproduct Substances 0.000 claims abstract description 6
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- 229960003280 cupric chloride Drugs 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims description 8
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 8
- YSMYHWBQQONPRD-UHFFFAOYSA-N 2-chlorofuran Chemical compound ClC1=CC=CO1 YSMYHWBQQONPRD-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- NWQWQKUXRJYXFH-UHFFFAOYSA-N 2,2-Dichloroacetaldehyde Chemical compound ClC(Cl)C=O NWQWQKUXRJYXFH-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229940029273 trichloroacetaldehyde Drugs 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- GMUIHGWBQIUCST-RQOWECAXSA-N (z)-2-chlorobut-2-enal Chemical compound C\C=C(/Cl)C=O GMUIHGWBQIUCST-RQOWECAXSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- CGCJBAIEQANINV-UHFFFAOYSA-N 1,1,1-trichloro-2,2-diethoxyethane Chemical compound CCOC(C(Cl)(Cl)Cl)OCC CGCJBAIEQANINV-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- OVXJWSYBABKZMD-UHFFFAOYSA-N 2-chloro-1,1-diethoxyethane Chemical compound CCOC(CCl)OCC OVXJWSYBABKZMD-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 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
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3013817A DE3013817C2 (de) | 1980-04-10 | 1980-04-10 | Verfahren zur Isolierung von Mono-chlor-acetaldehyd |
| DEP3013817.1 | 1980-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1171812A true CA1171812A (en) | 1984-07-31 |
Family
ID=6099681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000374936A Expired CA1171812A (en) | 1980-04-10 | 1981-04-08 | Process for the isolation of monochloroacetaldehyde |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4311563A (OSRAM) |
| JP (1) | JPS5827253B2 (OSRAM) |
| CA (1) | CA1171812A (OSRAM) |
| DE (1) | DE3013817C2 (OSRAM) |
| FR (1) | FR2480277A1 (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3460813D1 (en) * | 1983-06-13 | 1986-10-30 | Babcock Hitachi Kk | Process for producing acetaldehyde |
| US4826600A (en) * | 1987-06-24 | 1989-05-02 | Amoco Corporation | Process for treatment of wastewater |
| JPH02223575A (ja) * | 1988-11-09 | 1990-09-05 | Kureha Chem Ind Co Ltd | モノクロルアセトアルデヒド三量体の製造方法 |
| US5558747A (en) * | 1993-06-25 | 1996-09-24 | Amvac Chemical Corporation | Process for azeotropic distillation of aqueous chloral mixtures |
| US7562481B2 (en) | 2005-04-12 | 2009-07-21 | Brian Esch | Sling mounts for firearms |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2702783A (en) * | 1952-03-14 | 1955-02-22 | Gulf Research Development Co | Process of separating mixtures of organic compounds |
| US2947671A (en) * | 1958-06-23 | 1960-08-02 | Allied Chem | Purification of dichloroacetaldehyde |
| DE1130426B (de) | 1961-06-27 | 1962-05-30 | Consortium Elektrochem Ind | Verfahren zur Abtrennung von Monochloracetaldehyd aus Mischungen von chlorierten Acetaldehyden |
| DE1147211B (de) | 1961-06-27 | 1963-04-18 | Consortium Elektrochem Ind | Verfahren zur Reinigung von Acetaldehyd und gleichzeitige Gewinnung von chlorierten Acetaldehyden |
-
1980
- 1980-04-10 DE DE3013817A patent/DE3013817C2/de not_active Expired
-
1981
- 1981-02-06 JP JP56015866A patent/JPS5827253B2/ja not_active Expired
- 1981-03-31 US US06/249,324 patent/US4311563A/en not_active Expired - Fee Related
- 1981-04-02 FR FR8106623A patent/FR2480277A1/fr active Granted
- 1981-04-08 CA CA000374936A patent/CA1171812A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56145237A (en) | 1981-11-11 |
| FR2480277B1 (OSRAM) | 1984-01-13 |
| DE3013817A1 (de) | 1981-10-15 |
| FR2480277A1 (fr) | 1981-10-16 |
| JPS5827253B2 (ja) | 1983-06-08 |
| DE3013817C2 (de) | 1983-01-27 |
| US4311563A (en) | 1982-01-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20010731 |