AT404938B - Verfahren zur reinigung von o-phthaldialdehyd - Google Patents
Verfahren zur reinigung von o-phthaldialdehyd Download PDFInfo
- Publication number
- AT404938B AT404938B AT0189096A AT189096A AT404938B AT 404938 B AT404938 B AT 404938B AT 0189096 A AT0189096 A AT 0189096A AT 189096 A AT189096 A AT 189096A AT 404938 B AT404938 B AT 404938B
- Authority
- AT
- Austria
- Prior art keywords
- yield
- acid
- mbar
- phthalaldehyde
- opa
- Prior art date
Links
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 17
- 229940054441 o-phthalaldehyde Drugs 0.000 claims abstract description 25
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 6
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 230000007062 hydrolysis Effects 0.000 claims abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
- 239000012074 organic phase Substances 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 235000011007 phosphoric acid Nutrition 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 238000006705 deacetalization reaction Methods 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000005949 ozonolysis reaction Methods 0.000 description 7
- -1 aldehyde acids Chemical class 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 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
- C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
-
- 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
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0189096A AT404938B (de) | 1996-10-30 | 1996-10-30 | Verfahren zur reinigung von o-phthaldialdehyd |
| DK97118404T DK0839789T3 (da) | 1996-10-30 | 1997-10-23 | Fremgangsmåde til oprensning af o-phthaldialdehyd |
| EP97118404A EP0839789B1 (de) | 1996-10-30 | 1997-10-23 | Verfahren zur Reinigung von O-Phthaldialdehyd |
| AT97118404T ATE187711T1 (de) | 1996-10-30 | 1997-10-23 | Verfahren zur reinigung von o-phthaldialdehyd |
| ES97118404T ES2139418T3 (es) | 1996-10-30 | 1997-10-23 | Procedimiento para la purificacion de dialdehido o-ftalico. |
| DE59700844T DE59700844D1 (de) | 1996-10-30 | 1997-10-23 | Verfahren zur Reinigung von O-Phthaldialdehyd |
| CN97122766A CN1116268C (zh) | 1996-10-30 | 1997-10-29 | 纯化邻苯二醛的方法 |
| JP29722197A JP3968158B2 (ja) | 1996-10-30 | 1997-10-29 | ｏ− フタルアルデヒドの精製方法 |
| US08/960,618 US5874637A (en) | 1996-10-30 | 1997-10-29 | Process for the purification of o-phthalaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0189096A AT404938B (de) | 1996-10-30 | 1996-10-30 | Verfahren zur reinigung von o-phthaldialdehyd |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA189096A ATA189096A (de) | 1998-08-15 |
| AT404938B true AT404938B (de) | 1999-03-25 |
Family
ID=3523232
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0189096A AT404938B (de) | 1996-10-30 | 1996-10-30 | Verfahren zur reinigung von o-phthaldialdehyd |
| AT97118404T ATE187711T1 (de) | 1996-10-30 | 1997-10-23 | Verfahren zur reinigung von o-phthaldialdehyd |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT97118404T ATE187711T1 (de) | 1996-10-30 | 1997-10-23 | Verfahren zur reinigung von o-phthaldialdehyd |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5874637A (https=) |
| EP (1) | EP0839789B1 (https=) |
| JP (1) | JP3968158B2 (https=) |
| CN (1) | CN1116268C (https=) |
| AT (2) | AT404938B (https=) |
| DE (1) | DE59700844D1 (https=) |
| DK (1) | DK0839789T3 (https=) |
| ES (1) | ES2139418T3 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT413537B (de) | 2001-05-15 | 2006-03-15 | Dsm Fine Chem Austria Gmbh | Verbessertes verfahren zur reinigung und formulierung von o-phthalaldehyd |
| US20050136086A1 (en) * | 2003-12-19 | 2005-06-23 | Rafael Herruzo | Efficacy enhancers for germicides |
| US20050238732A1 (en) * | 2003-12-19 | 2005-10-27 | Kaitao Lu | Carbonated germicide with pressure control |
| US20050136118A1 (en) * | 2003-12-19 | 2005-06-23 | Wu Su-Syin S. | Distribution and preparation of germicidal compositions |
| US7390837B2 (en) | 2004-01-30 | 2008-06-24 | Ethicon, Inc. | Germicidal compositions containing phenylmalonaldehyde-type compounds, or mixtures of phenylmalonaldehyde-type compounds and phthalaldehydes, and methods of using such compositions for disinfection or sterilization |
| US7476767B2 (en) * | 2004-01-30 | 2009-01-13 | Ethicon, Inc. | Alpha-hydroxy sulfonate aldehydes, germicidal compositions containing the alpha-hydroxy sulfonate aldehydes, or mixtures of alpha-hydroxy sulfonate aldehydes and phthalaldehydes, and methods of using the compounds or compositions for disinfection or sterilization |
| AT501448B1 (de) * | 2005-03-02 | 2006-11-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von wässrigen ortho-phthalaldehyd-lösungen |
| AT502144A1 (de) | 2005-06-28 | 2007-01-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von hochreinem, halogenfreien o-phthalaldehyd |
| US7291649B2 (en) * | 2005-06-29 | 2007-11-06 | Ethicon, Inc. | Forming germicidal aromatic dialdehydes with acetals |
| CN104317165B (zh) * | 2014-09-22 | 2016-05-25 | 村上精密制版（昆山）有限公司 | 丝网印刷用印版的补强剂及其应用方法和补强后的印版 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT380008B (de) * | 1983-12-23 | 1986-03-25 | Chemie Linz Ag | Verfahren zur herstellung von mono- oder biscarbonylverbindungen |
| EP0522312A1 (de) * | 1991-07-05 | 1993-01-13 | BASF Aktiengesellschaft | o-Phthaldialdehydtetraalkylacetale, ihre Herstellung und ihre Verwendung als Depotverbindung |
| DE4407986A1 (de) * | 1993-03-19 | 1994-09-22 | Basf Ag | Verfahren zur Herstellung von o-Phthalaldehydtetraalkylacetalen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3492356A (en) * | 1966-05-31 | 1970-01-27 | Marathon Oil Co | Method of recovering aldehydes and ketones |
-
1996
- 1996-10-30 AT AT0189096A patent/AT404938B/de not_active IP Right Cessation
-
1997
- 1997-10-23 ES ES97118404T patent/ES2139418T3/es not_active Expired - Lifetime
- 1997-10-23 DE DE59700844T patent/DE59700844D1/de not_active Expired - Lifetime
- 1997-10-23 DK DK97118404T patent/DK0839789T3/da active
- 1997-10-23 AT AT97118404T patent/ATE187711T1/de not_active IP Right Cessation
- 1997-10-23 EP EP97118404A patent/EP0839789B1/de not_active Expired - Lifetime
- 1997-10-29 JP JP29722197A patent/JP3968158B2/ja not_active Expired - Lifetime
- 1997-10-29 US US08/960,618 patent/US5874637A/en not_active Expired - Lifetime
- 1997-10-29 CN CN97122766A patent/CN1116268C/zh not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT380008B (de) * | 1983-12-23 | 1986-03-25 | Chemie Linz Ag | Verfahren zur herstellung von mono- oder biscarbonylverbindungen |
| EP0522312A1 (de) * | 1991-07-05 | 1993-01-13 | BASF Aktiengesellschaft | o-Phthaldialdehydtetraalkylacetale, ihre Herstellung und ihre Verwendung als Depotverbindung |
| DE4407986A1 (de) * | 1993-03-19 | 1994-09-22 | Basf Ag | Verfahren zur Herstellung von o-Phthalaldehydtetraalkylacetalen |
Also Published As
| Publication number | Publication date |
|---|---|
| DK0839789T3 (da) | 2000-05-08 |
| EP0839789A1 (de) | 1998-05-06 |
| DE59700844D1 (de) | 2000-01-20 |
| ATE187711T1 (de) | 2000-01-15 |
| ATA189096A (de) | 1998-08-15 |
| JPH10182542A (ja) | 1998-07-07 |
| CN1116268C (zh) | 2003-07-30 |
| EP0839789B1 (de) | 1999-12-15 |
| US5874637A (en) | 1999-02-23 |
| JP3968158B2 (ja) | 2007-08-29 |
| ES2139418T3 (es) | 2000-02-01 |
| CN1181369A (zh) | 1998-05-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| ELJ | Ceased due to non-payment of the annual fee |