DE2104206B2 - Verfahren zur kontinuierlichen herstellung von orthoameisensaeuremethyloder aethylester - Google Patents
Verfahren zur kontinuierlichen herstellung von orthoameisensaeuremethyloder aethylesterInfo
- Publication number
- DE2104206B2 DE2104206B2 DE19712104206 DE2104206A DE2104206B2 DE 2104206 B2 DE2104206 B2 DE 2104206B2 DE 19712104206 DE19712104206 DE 19712104206 DE 2104206 A DE2104206 A DE 2104206A DE 2104206 B2 DE2104206 B2 DE 2104206B2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- chloroform
- alkali
- reactor
- acid methyl
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 14
- 239000002253 acid Substances 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 title 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000003513 alkali Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 7
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical group COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 150000002905 orthoesters Chemical class 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical class Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- -1 orthoformic acid ester Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction 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
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/32—Compounds having groups or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712104206 DE2104206B2 (de) | 1971-01-29 | 1971-01-29 | Verfahren zur kontinuierlichen herstellung von orthoameisensaeuremethyloder aethylester |
| JP3036671A JPS565727B1 (enExample) | 1971-01-29 | 1971-05-07 | |
| IT4775672A IT949653B (it) | 1971-01-29 | 1972-01-15 | Procedimento per la produzione continua di orto formiati alchilici |
| BE778412A BE778412A (fr) | 1971-01-29 | 1972-01-24 | Procede de preparation en continu d'esters alcoyliques d'acide orthoformique |
| CH99872A CH566950A5 (enExample) | 1971-01-29 | 1972-01-24 | |
| NL7201170A NL7201170A (enExample) | 1971-01-29 | 1972-01-28 | |
| GB424572A GB1360541A (en) | 1971-01-29 | 1972-01-28 | Preparation of alkyl esters of orthoformic acid |
| FR7202991A FR2123538B1 (enExample) | 1971-01-29 | 1972-01-28 | |
| US462163A US3901946A (en) | 1971-01-29 | 1974-04-18 | Method for the continuous manufacture of orthoformic acid alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712104206 DE2104206B2 (de) | 1971-01-29 | 1971-01-29 | Verfahren zur kontinuierlichen herstellung von orthoameisensaeuremethyloder aethylester |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2104206A1 DE2104206A1 (de) | 1972-08-24 |
| DE2104206B2 true DE2104206B2 (de) | 1973-03-08 |
| DE2104206C3 DE2104206C3 (enExample) | 1973-10-11 |
Family
ID=5797289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712104206 Granted DE2104206B2 (de) | 1971-01-29 | 1971-01-29 | Verfahren zur kontinuierlichen herstellung von orthoameisensaeuremethyloder aethylester |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS565727B1 (enExample) |
| BE (1) | BE778412A (enExample) |
| CH (1) | CH566950A5 (enExample) |
| DE (1) | DE2104206B2 (enExample) |
| FR (1) | FR2123538B1 (enExample) |
| GB (1) | GB1360541A (enExample) |
| IT (1) | IT949653B (enExample) |
| NL (1) | NL7201170A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3606472A1 (de) * | 1986-02-28 | 1987-09-03 | Huels Chemische Werke Ag | Verfahren zur herstellung von orthoameisensaeureester |
| DE19853089A1 (de) * | 1998-11-18 | 2000-05-25 | Basf Ag | Verfahren zur Herstellung von Orthoestern |
-
1971
- 1971-01-29 DE DE19712104206 patent/DE2104206B2/de active Granted
- 1971-05-07 JP JP3036671A patent/JPS565727B1/ja active Pending
-
1972
- 1972-01-15 IT IT4775672A patent/IT949653B/it active
- 1972-01-24 CH CH99872A patent/CH566950A5/xx not_active IP Right Cessation
- 1972-01-24 BE BE778412A patent/BE778412A/xx not_active IP Right Cessation
- 1972-01-28 FR FR7202991A patent/FR2123538B1/fr not_active Expired
- 1972-01-28 NL NL7201170A patent/NL7201170A/xx not_active Application Discontinuation
- 1972-01-28 GB GB424572A patent/GB1360541A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS565727B1 (enExample) | 1981-02-06 |
| FR2123538A1 (enExample) | 1972-09-08 |
| BE778412A (fr) | 1972-05-16 |
| DE2104206C3 (enExample) | 1973-10-11 |
| DE2104206A1 (de) | 1972-08-24 |
| NL7201170A (enExample) | 1972-08-01 |
| CH566950A5 (enExample) | 1975-09-30 |
| GB1360541A (en) | 1974-07-17 |
| FR2123538B1 (enExample) | 1974-06-28 |
| IT949653B (it) | 1973-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS AG, 4370 MARL, DE |