JP3968160B2 - ｏ−フタルアルデヒド− グルタルアルデヒド水溶液の製造方法 - Google Patents
ｏ−フタルアルデヒド− グルタルアルデヒド水溶液の製造方法 Download PDFInfo
- Publication number
- JP3968160B2 JP3968160B2 JP32316997A JP32316997A JP3968160B2 JP 3968160 B2 JP3968160 B2 JP 3968160B2 JP 32316997 A JP32316997 A JP 32316997A JP 32316997 A JP32316997 A JP 32316997A JP 3968160 B2 JP3968160 B2 JP 3968160B2
- Authority
- JP
- Japan
- Prior art keywords
- solution
- opa
- phthalaldehyde
- acetal
- glutaraldehyde
- 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 - Fee Related
Links
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 19
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000243 solution Substances 0.000 claims abstract description 43
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract description 14
- 229940054441 o-phthalaldehyde Drugs 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 18
- -1 o-phthalaldehyde acetal Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical compound CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000005949 ozonolysis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation 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
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT2053/96 | 1996-11-26 | ||
| AT0205396A AT404592B (de) | 1996-11-26 | 1996-11-26 | Verfahren zur herstellung von wässrigen o-phthalaldehyd-glutaraldehydlösungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10182539A JPH10182539A (ja) | 1998-07-07 |
| JP3968160B2 true JP3968160B2 (ja) | 2007-08-29 |
Family
ID=3526769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32316997A Expired - Fee Related JP3968160B2 (ja) | 1996-11-26 | 1997-11-25 | ｏ−フタルアルデヒド− グルタルアルデヒド水溶液の製造方法 |
Country Status (9)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040071592A1 (en) * | 2002-10-10 | 2004-04-15 | Ioana Annis | Fast dissolving solid ortho-phthalic aldehyde formulations |
| AT501448B1 (de) * | 2005-03-02 | 2006-11-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von wässrigen ortho-phthalaldehyd-lösungen |
| US7291649B2 (en) * | 2005-06-29 | 2007-11-06 | Ethicon, Inc. | Forming germicidal aromatic dialdehydes with acetals |
| EP2563411B9 (en) | 2010-04-27 | 2017-07-12 | Whiteley Corporation Pty Ltd | Synergystic, non-equilibrium aldehyde biocides |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244876A (en) * | 1978-11-17 | 1981-01-13 | Union Carbide Corporation | Acetal-acid compositions |
| DE3108790A1 (de) * | 1981-03-07 | 1982-09-16 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von bis(dialkoximethyl)benzolen |
| US4847304A (en) * | 1987-05-21 | 1989-07-11 | Surgikos, Inc. | Disinfecting and sterilizing composition |
| DE4122314A1 (de) * | 1991-07-05 | 1993-01-07 | Basf Ag | O-phthaldialdehydtetraalkylacetale, ihre herstellung und ihre verwendung als depotverbindung |
| US5128051A (en) * | 1991-09-30 | 1992-07-07 | Union Carbide Chemicals & Plastics Technology Corporation | Method for the control of biofouling |
| DE4407986A1 (de) * | 1993-03-19 | 1994-09-22 | Basf Ag | Verfahren zur Herstellung von o-Phthalaldehydtetraalkylacetalen |
| US5723498A (en) * | 1994-11-21 | 1998-03-03 | Degussa Aktiengellschaft | Composition capable of releasing acrolein and its use |
-
1996
- 1996-11-26 AT AT0205396A patent/AT404592B/de not_active IP Right Cessation
-
1997
- 1997-11-17 IN IN3284DE1997 patent/IN187090B/en unknown
- 1997-11-18 DK DK97120163T patent/DK0843966T3/da active
- 1997-11-18 ES ES97120163T patent/ES2180877T3/es not_active Expired - Lifetime
- 1997-11-18 DE DE59708182T patent/DE59708182D1/de not_active Expired - Fee Related
- 1997-11-18 EP EP97120163A patent/EP0843966B1/de not_active Expired - Lifetime
- 1997-11-18 AT AT97120163T patent/ATE223647T1/de not_active IP Right Cessation
- 1997-11-25 JP JP32316997A patent/JP3968160B2/ja not_active Expired - Fee Related
- 1997-11-25 CN CN97126296A patent/CN1093850C/zh not_active Expired - Fee Related
- 1997-11-26 US US08/979,952 patent/US5872153A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE223647T1 (de) | 2002-09-15 |
| DK0843966T3 (da) | 2002-10-07 |
| US5872153A (en) | 1999-02-16 |
| DE59708182D1 (de) | 2002-10-17 |
| ES2180877T3 (es) | 2003-02-16 |
| IN187090B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2002-01-26 |
| ATA205396A (de) | 1998-05-15 |
| JPH10182539A (ja) | 1998-07-07 |
| EP0843966B1 (de) | 2002-09-11 |
| CN1185428A (zh) | 1998-06-24 |
| CN1093850C (zh) | 2002-11-06 |
| AT404592B (de) | 1998-12-28 |
| EP0843966A1 (de) | 1998-05-27 |
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