DE2913677C2 - Verfahren zur Herstellung von Acetaldehyddimethylacetal - Google Patents
Verfahren zur Herstellung von AcetaldehyddimethylacetalInfo
- Publication number
- DE2913677C2 DE2913677C2 DE2913677A DE2913677A DE2913677C2 DE 2913677 C2 DE2913677 C2 DE 2913677C2 DE 2913677 A DE2913677 A DE 2913677A DE 2913677 A DE2913677 A DE 2913677A DE 2913677 C2 DE2913677 C2 DE 2913677C2
- Authority
- DE
- Germany
- Prior art keywords
- cobalt
- nickel
- dimethyl acetal
- methanol
- reaction
- 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
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 24
- 229910017052 cobalt Inorganic materials 0.000 claims description 12
- 239000010941 cobalt Substances 0.000 claims description 12
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 18
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- 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 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- -1 Jotlide Chemical compound 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- NVIVJPRCKQTWLY-UHFFFAOYSA-N cobalt nickel Chemical compound [Co][Ni][Co] NVIVJPRCKQTWLY-UHFFFAOYSA-N 0.000 description 1
- AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2913677A DE2913677C2 (de) | 1979-04-05 | 1979-04-05 | Verfahren zur Herstellung von Acetaldehyddimethylacetal |
| GB8010023A GB2046262B (en) | 1979-04-05 | 1980-03-25 | Process for the production of an acetal |
| NL8001911A NL8001911A (nl) | 1979-04-05 | 1980-04-01 | Werkwijze voor de bereiding van aceetaldehyde- dimethylacetaal. |
| FR8007333A FR2453127A1 (fr) | 1979-04-05 | 1980-04-01 | Procede de preparation du dimethylacetal de l'acetaldehyde |
| US06/136,415 US4278819A (en) | 1979-04-05 | 1980-04-02 | Process for the production of acetaldehyde dimethyl acetal |
| JP4367780A JPS55141425A (en) | 1979-04-05 | 1980-04-04 | Manufacture of acetoaldehyde dimethylacetal |
| BE0/200125A BE882655A (fr) | 1979-04-05 | 1980-04-04 | Procede de fabrication de dimethylacetal d'acetaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2913677A DE2913677C2 (de) | 1979-04-05 | 1979-04-05 | Verfahren zur Herstellung von Acetaldehyddimethylacetal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2913677A1 DE2913677A1 (de) | 1980-10-16 |
| DE2913677C2 true DE2913677C2 (de) | 1983-03-03 |
Family
ID=6067502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2913677A Expired DE2913677C2 (de) | 1979-04-05 | 1979-04-05 | Verfahren zur Herstellung von Acetaldehyddimethylacetal |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4278819A (enExample) |
| JP (1) | JPS55141425A (enExample) |
| BE (1) | BE882655A (enExample) |
| DE (1) | DE2913677C2 (enExample) |
| FR (1) | FR2453127A1 (enExample) |
| GB (1) | GB2046262B (enExample) |
| NL (1) | NL8001911A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3042633C2 (de) * | 1980-11-12 | 1983-03-24 | Union Rheinische Braunkohlen Kraftstoff AG, 5000 Köln | Verfahren zur Herstellung von Acetaldehyddimethylacetal |
| US4388477A (en) * | 1981-06-02 | 1983-06-14 | Eastman Kodak Company | Hydroformylation process employing unmodified rhodium-cobalt catalyst |
| FR2577920B1 (fr) * | 1985-02-25 | 1987-04-17 | Rhone Poulenc Spec Chim | Procede de preparation d'acetals |
| DE3919890A1 (de) * | 1989-06-19 | 1990-12-20 | Huels Chemische Werke Ag | Verfahren zur herstellung von arylacetaldehyd-dialkylacetalen |
| US5202500A (en) * | 1989-06-19 | 1993-04-13 | Huels Aktiengesellschaft | Process for the preparation of arylacetaldehyde-dialkylacetals |
| US5011859A (en) * | 1990-03-30 | 1991-04-30 | Merrell Dow Pharmaceuticals Inc. | Di- and tetra-fluoro analogs of squalene as inhibitors of squalene epoxidase |
| US5064864A (en) * | 1990-03-30 | 1991-11-12 | Merrell Dow Pharmaceuticals Inc. | Di- and tetra-fluoro analogs of squalene as inhibitors of squalene epoxidase |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727902A (en) * | 1951-12-18 | 1955-12-20 | Basf Ag | Process for the production of aliphatic oxygen compounds by carbonylation of alcohols and ethers |
| US3631111A (en) * | 1968-12-17 | 1971-12-28 | Gulf Research Development Co | Oxo process |
| BE842430A (nl) * | 1975-06-09 | 1976-12-01 | Werkwijze ter bereiding van ethanol uit methanol koolmonoxyde en waterstof | |
| JPS52133914A (en) * | 1976-04-30 | 1977-11-09 | Mitsubishi Gas Chem Co Inc | Preparation of acetaldehyde |
| US4190729A (en) * | 1977-09-19 | 1980-02-26 | Monsanto Company | Carbonylation process with stabilized catalyst |
-
1979
- 1979-04-05 DE DE2913677A patent/DE2913677C2/de not_active Expired
-
1980
- 1980-03-25 GB GB8010023A patent/GB2046262B/en not_active Expired
- 1980-04-01 NL NL8001911A patent/NL8001911A/nl not_active Application Discontinuation
- 1980-04-01 FR FR8007333A patent/FR2453127A1/fr active Granted
- 1980-04-02 US US06/136,415 patent/US4278819A/en not_active Expired - Lifetime
- 1980-04-04 BE BE0/200125A patent/BE882655A/fr not_active IP Right Cessation
- 1980-04-04 JP JP4367780A patent/JPS55141425A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB2046262B (en) | 1983-03-30 |
| BE882655A (fr) | 1980-07-31 |
| DE2913677A1 (de) | 1980-10-16 |
| FR2453127A1 (fr) | 1980-10-31 |
| US4278819A (en) | 1981-07-14 |
| JPS55141425A (en) | 1980-11-05 |
| GB2046262A (en) | 1980-11-12 |
| NL8001911A (nl) | 1980-10-07 |
| FR2453127B1 (enExample) | 1984-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| AG | Has addition no. |
Ref country code: DE Ref document number: 3042633 Format of ref document f/p: P |
|
| AG | Has addition no. |
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| D2 | Grant after examination | ||
| AG | Has addition no. |
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|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |