CH498828A - Verfahren zur Herstellung von Äthylenketalen von y-Ketocarbonsäureestern - Google Patents
Verfahren zur Herstellung von Äthylenketalen von y-KetocarbonsäureesternInfo
- Publication number
- CH498828A CH498828A CH607868A CH607868A CH498828A CH 498828 A CH498828 A CH 498828A CH 607868 A CH607868 A CH 607868A CH 607868 A CH607868 A CH 607868A CH 498828 A CH498828 A CH 498828A
- Authority
- CH
- Switzerland
- Prior art keywords
- ester
- ketocarboxylic acid
- ethylene
- ethyl
- ethylene glycol
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 35
- 239000002253 acid Substances 0.000 title claims abstract description 32
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000005977 Ethylene Substances 0.000 title claims abstract description 31
- 239000000543 intermediate Substances 0.000 title abstract description 5
- 239000003814 drug Substances 0.000 title abstract description 4
- 239000002917 insecticide Substances 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 11
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000006227 byproduct Substances 0.000 claims abstract description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 84
- -1 ethylene glycol diester Chemical class 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 229940058352 levulinate Drugs 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000003905 agrochemical Substances 0.000 abstract description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 235000019441 ethanol Nutrition 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 15
- 125000004185 ester group Chemical group 0.000 description 15
- 238000005755 formation reaction Methods 0.000 description 15
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- 238000005907 ketalization reaction Methods 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 229930194542 Keto Natural products 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229940040102 levulinic acid Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000008282 halocarbons Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- JOOXCMJARBKPKM-UHFFFAOYSA-N laevulinic acid Natural products CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2677367 | 1967-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH498828A true CH498828A (de) | 1970-11-15 |
Family
ID=12202600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH607868A CH498828A (de) | 1967-04-25 | 1968-04-24 | Verfahren zur Herstellung von Äthylenketalen von y-Ketocarbonsäureestern |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE714139A (en:Method) |
| BR (1) | BR6898523D0 (en:Method) |
| CH (1) | CH498828A (en:Method) |
| CS (1) | CS162615B2 (en:Method) |
| DE (1) | DE1768268C3 (en:Method) |
| DK (1) | DK121126B (en:Method) |
| FR (1) | FR1560177A (en:Method) |
| GB (1) | GB1196202A (en:Method) |
| IL (1) | IL29862A (en:Method) |
| NL (1) | NL6805723A (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010138907A1 (en) | 2009-05-29 | 2010-12-02 | Segetis Inc. | Solvent, solution, cleaning composition and methods |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8828917B2 (en) * | 2010-08-12 | 2014-09-09 | Segetis, Inc. | Carboxy ester ketal removal compositions, methods of manufacture, and uses thereof |
| WO2014047428A1 (en) | 2012-09-21 | 2014-03-27 | Segetis, Inc. | Cleaning, surfactant, and personal care compositions |
| CN110922445A (zh) * | 2018-09-20 | 2020-03-27 | 天津金耀集团有限公司 | 一种制备孕甾16，17位缩酮的合成方法 |
-
1968
- 1968-04-22 IL IL29862A patent/IL29862A/en unknown
- 1968-04-23 DK DK184868AA patent/DK121126B/da unknown
- 1968-04-23 BR BR198523/68A patent/BR6898523D0/pt unknown
- 1968-04-23 GB GB19219/68A patent/GB1196202A/en not_active Expired
- 1968-04-23 FR FR1560177D patent/FR1560177A/fr not_active Expired
- 1968-04-23 DE DE1768268A patent/DE1768268C3/de not_active Expired
- 1968-04-23 NL NL6805723A patent/NL6805723A/xx unknown
- 1968-04-23 CS CS2997A patent/CS162615B2/cs unknown
- 1968-04-24 BE BE714139D patent/BE714139A/xx unknown
- 1968-04-24 CH CH607868A patent/CH498828A/de not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010138907A1 (en) | 2009-05-29 | 2010-12-02 | Segetis Inc. | Solvent, solution, cleaning composition and methods |
| EP2435552A4 (en) * | 2009-05-29 | 2014-03-26 | Segetis Inc | Solvent, solution, cleaning composition and methods |
Also Published As
| Publication number | Publication date |
|---|---|
| BE714139A (en:Method) | 1968-09-16 |
| CS162615B2 (en:Method) | 1975-07-15 |
| FR1560177A (en:Method) | 1969-03-14 |
| GB1196202A (en) | 1970-06-24 |
| IL29862A (en) | 1972-01-27 |
| BR6898523D0 (pt) | 1973-01-16 |
| DE1768268B2 (de) | 1973-04-05 |
| IL29862A0 (en) | 1968-06-20 |
| NL6805723A (en:Method) | 1968-10-28 |
| DE1768268C3 (de) | 1973-10-31 |
| DE1768268A1 (de) | 1972-02-24 |
| DK121126B (da) | 1971-09-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO1999050221A2 (de) | Verfahren zur herstellung von (meth)acrylsäure und (meth)acrylsäureestern | |
| EP0847976B1 (de) | Verfahren zur Herstellung von Glyoxalmonoacetalen | |
| DE102004060541A1 (de) | Verfahren zur Herstellung von Alkandiolen und Alkantriolen mit einer vicinalen Diol-Gruppe | |
| DE2811480A1 (de) | Verfahren zur herstellung und rueckgewinnung von glyoxylsaeurehemiacetalestern in verbesserten ausbeuten | |
| DE2159882C3 (de) | Verfahren zur Herstellung niederer Alkylester der cis-Chrysanthemum-monocarbonsäure | |
| DE1816386C3 (de) | Verfahren zur Herstellung von Vanadiumoxitri alkoholaten | |
| CH498828A (de) | Verfahren zur Herstellung von Äthylenketalen von y-Ketocarbonsäureestern | |
| WO1999044975A1 (de) | Verfahren zur destillation butandiolhaltiger gemische | |
| EP0335221B1 (de) | Verfahren zur Gewinnung von 2-Methylalkanalen aus Gemischen isomerer Aldehyde | |
| EP0286981B1 (de) | Verfahren zur Herstellung von Carbonsäuremethylestern | |
| EP1099697A1 (de) | Verfahren zur Herstellung von Alkalisalzen der L-Ascorbinsäure | |
| DE2519990C3 (de) | Verfahren zur Herstellung von Humulonen | |
| DE2058519B2 (de) | Verfahren zur gewinnung von ditrimethylolpropan aus einem dasselbe enthaltende reaktionsgemisch | |
| DE2658283A1 (de) | Verfahren zur herstellung von 1,1-dihalogen-4-methyl-1,3-pentadienen und ihren zwischenprodukten | |
| DE707426C (de) | Herstellung von ungesaettigten Aldehyden | |
| DE1668609A1 (de) | Verfahren zur Herstellung konzentrierter Acrylsaeure | |
| DE10002835C1 (de) | Verfahren zur Herstellung von 4-Methylpyrimidin | |
| AT413537B (de) | Verbessertes verfahren zur reinigung und formulierung von o-phthalaldehyd | |
| DE1643195C (en:Method) | ||
| AT392468B (de) | Verfahren zur herstellung lagerstabiler laevulinsaeure | |
| DE19922722A1 (de) | Verfahren zur Herstellung von (Meth)acrylsäureestern | |
| DE3325976C2 (en:Method) | ||
| DE19853089A1 (de) | Verfahren zur Herstellung von Orthoestern | |
| DE1545689C2 (de) | Verfahren zur Herstellung von 2-Methyl-3-carbäthoxy-5,6-dihydropyran | |
| CH495309A (de) | Verfahren zur Herstellung von Dihydromyrcenol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |