DE2225243A1 - - Google Patents
Info
- Publication number
- DE2225243A1 DE2225243A1 DE19722225243 DE2225243A DE2225243A1 DE 2225243 A1 DE2225243 A1 DE 2225243A1 DE 19722225243 DE19722225243 DE 19722225243 DE 2225243 A DE2225243 A DE 2225243A DE 2225243 A1 DE2225243 A1 DE 2225243A1
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- low molecular
- acid
- mixture
- parts
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 238000006386 neutralization reaction Methods 0.000 claims description 11
- 230000003472 neutralizing effect Effects 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 101150065749 Churc1 gene Proteins 0.000 claims description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 7
- 102100038239 Protein Churchill Human genes 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 235000019645 odor Nutrition 0.000 claims 1
- 239000002253 acid Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 14
- 238000009833 condensation Methods 0.000 description 14
- 230000005494 condensation Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000001241 acetals Chemical class 0.000 description 9
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 7
- 229940043353 maltol Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000003512 Claisen condensation reaction Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- SMCVPMKCDDNUCQ-UHFFFAOYSA-N methyl 3,3-dimethoxypropanoate Chemical compound COC(OC)CC(=O)OC SMCVPMKCDDNUCQ-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- -1 methyl- Chemical group 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PMCYKVQJIDOBRK-UHFFFAOYSA-N (6-methyl-4-oxopyran-3-yl) acetate Chemical compound CC(=O)OC1=COC(C)=CC1=O PMCYKVQJIDOBRK-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000159 acid neutralizing agent Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical class OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- SIALOQYKFQEKOG-UHFFFAOYSA-N ethyl 3,3-diethoxypropanoate Chemical compound CCOC(OCC)CC(=O)OCC SIALOQYKFQEKOG-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/175—Saturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46035981A JPS5114484B1 (enrdf_load_stackoverflow) | 1971-05-26 | 1971-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2225243A1 true DE2225243A1 (enrdf_load_stackoverflow) | 1972-12-14 |
Family
ID=12457047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722225243 Pending DE2225243A1 (enrdf_load_stackoverflow) | 1971-05-26 | 1972-05-24 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5114484B1 (enrdf_load_stackoverflow) |
| CA (1) | CA956325A (enrdf_load_stackoverflow) |
| CH (1) | CH538438A (enrdf_load_stackoverflow) |
| DE (1) | DE2225243A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2139173B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1386166A (enrdf_load_stackoverflow) |
| IT (1) | IT955938B (enrdf_load_stackoverflow) |
| NL (1) | NL7207200A (enrdf_load_stackoverflow) |
-
1971
- 1971-05-26 JP JP46035981A patent/JPS5114484B1/ja active Pending
-
1972
- 1972-05-24 DE DE19722225243 patent/DE2225243A1/de active Pending
- 1972-05-24 CH CH765772A patent/CH538438A/fr not_active IP Right Cessation
- 1972-05-25 GB GB2457672A patent/GB1386166A/en not_active Expired
- 1972-05-25 CA CA143,031A patent/CA956325A/en not_active Expired
- 1972-05-26 FR FR7219001A patent/FR2139173B1/fr not_active Expired
- 1972-05-26 IT IT2495572A patent/IT955938B/it active
- 1972-05-26 NL NL7207200A patent/NL7207200A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2139173A1 (enrdf_load_stackoverflow) | 1973-01-05 |
| CA956325A (en) | 1974-10-15 |
| IT955938B (it) | 1973-09-29 |
| FR2139173B1 (enrdf_load_stackoverflow) | 1977-06-17 |
| GB1386166A (en) | 1975-03-05 |
| JPS5114484B1 (enrdf_load_stackoverflow) | 1976-05-10 |
| CH538438A (fr) | 1973-06-30 |
| NL7207200A (enrdf_load_stackoverflow) | 1972-11-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2721264C2 (de) | Verfahren zur Herstellung von Di-n-propylessigsäure und deren nichttoxischen Alkali- und Erdalkalimetallsalzen | |
| DE3002678A1 (de) | Verfahren zur herstellung von p-n-alkylbenzoesaeure | |
| EP1250301A1 (de) | Verfahren zur herstellung von trimethylolalkanen | |
| EP0246581B1 (de) | Verfahren zur Herstellung von alpha-substituierten gamma-Butyrolactonen | |
| DE2811480C2 (de) | Verfahren zur Gewinnung von Glyoxylsäure-hemiacetalestern aus Destillationsrückständen | |
| CH661268A5 (de) | Verfahren zur herstellung von arylalkansaeureestern und deren umwandlung in arylalkancarbonsaeuren. | |
| CH628012A5 (de) | Verfahren zur herstellung von cyklopentenonderivaten. | |
| CH702298B1 (de) | Verfahren zur Herstellung von Cyanoalkylpropionat-Derivaten. | |
| DD239591A5 (de) | Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoesaeure | |
| DE2726393C2 (de) | Verfahren zur Herstellung von 5-(quartär-Alkyl)resorcinen | |
| DE1793570C3 (de) | Verfahren zur Herstellung von Methylveratrylketon. Ausscheidung aus: 1518037 | |
| DE2852975C2 (de) | 5-Cyano-1-alkylpyrrol-2-essigsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1951294C3 (de) | Verfahren zur Herstellung von 3-Hydroxy-2-methyl-y-pyron (Maltol) | |
| DE2225243A1 (enrdf_load_stackoverflow) | ||
| EP0061669B1 (de) | Verbessertes Verfahren zur Herstellung von Cyclohexan-1,3-dionen sowie einige neue bicyclische Cyclohexan-1,3-dione | |
| DE2721265C2 (de) | Verfahren zur Herstellung von Di- n-propylacetonitril | |
| DE707426C (de) | Herstellung von ungesaettigten Aldehyden | |
| DE3824518A1 (de) | Verfahren zur herstellung von 4,4-dimethyl-1-(p-chlor-phenyl)-pentan-3-on | |
| DE2731543B2 (de) | Verfahren zur Herstellung von Cyclopentadecanolid | |
| DE3338547C2 (de) | Verfahren zur Herstellung von 2,2,4-Trimethyl-1,3-pentandioldiisobutyrat | |
| DE1643195C (enrdf_load_stackoverflow) | ||
| CH656610A5 (de) | Verfahren zur herstellung von 2-cyclopentenonen. | |
| DE1154095B (de) | Verfahren zur Herstellung von O, O-Dialkyldithiophosphorylessigsaeureestern | |
| DE2065698A1 (de) | Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon | |
| DE1643281C (de) | Verfahren zur Herstellung von Zearalan |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |