AU2009260402B2 - Preparation of glutaraldehyde - Google Patents
Preparation of glutaraldehyde Download PDFInfo
- Publication number
- AU2009260402B2 AU2009260402B2 AU2009260402A AU2009260402A AU2009260402B2 AU 2009260402 B2 AU2009260402 B2 AU 2009260402B2 AU 2009260402 A AU2009260402 A AU 2009260402A AU 2009260402 A AU2009260402 A AU 2009260402A AU 2009260402 B2 AU2009260402 B2 AU 2009260402B2
- Authority
- AU
- Australia
- Prior art keywords
- glutaraldehyde
- alkoxydihydropyran
- process according
- catalyst
- heterogeneous catalyst
- 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.)
- Ceased
Links
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 27
- 238000004821 distillation Methods 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 20
- 230000002378 acidificating effect Effects 0.000 claims abstract description 18
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- XCYWUZHUTJDTGS-UHFFFAOYSA-N 2-methoxy-3,4-dihydro-2h-pyran Chemical compound COC1CCC=CO1 XCYWUZHUTJDTGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012508 resin bead Substances 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 12
- 229960000587 glutaral Drugs 0.000 abstract 2
- 238000011109 contamination Methods 0.000 abstract 1
- 230000003247 decreasing effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000002952 polymeric resin Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- FHBAGVNIWPLUOK-UHFFFAOYSA-N 1,1,5,5-tetramethoxypentane Chemical compound COC(OC)CCCC(OC)OC FHBAGVNIWPLUOK-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- DNLONCVMTWHJOV-UHFFFAOYSA-N 2,6-dimethoxyoxane Chemical compound COC1CCCC(OC)O1 DNLONCVMTWHJOV-UHFFFAOYSA-N 0.000 description 1
- USXHLNDEUDDSKZ-UHFFFAOYSA-N 5,5-dimethoxypentanal Chemical compound COC(OC)CCCC=O USXHLNDEUDDSKZ-UHFFFAOYSA-N 0.000 description 1
- ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical group [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000011800 void material Substances 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
-
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7388508P | 2008-06-19 | 2008-06-19 | |
| US61/073,885 | 2008-06-19 | ||
| PCT/US2009/046730 WO2009155169A1 (en) | 2008-06-19 | 2009-06-09 | Preparation of glutaraldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2009260402A1 AU2009260402A1 (en) | 2009-12-23 |
| AU2009260402B2 true AU2009260402B2 (en) | 2014-05-22 |
Family
ID=40888256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009260402A Ceased AU2009260402B2 (en) | 2008-06-19 | 2009-06-09 | Preparation of glutaraldehyde |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7709686B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2300406B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5576366B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102066302B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2009260402B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0910026A2 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2495019C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009155169A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102992975B (zh) * | 2012-12-19 | 2015-03-04 | 湖北微控生物科技有限公司 | 一种连续制备戊二醛的方法 |
| CN105622375B (zh) * | 2016-03-17 | 2017-12-19 | 湖北荆洪生物科技股份有限公司 | 一种合成医用戊二醛的工艺路线 |
| CN106365971A (zh) * | 2016-08-27 | 2017-02-01 | 湖北荆洪生物科技股份有限公司 | 一种连续生产戊二醛的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6559346B1 (en) * | 1999-08-30 | 2003-05-06 | Basf Aktiengesellschaft | Method for the continuous production of glutaraldehyde |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB653765A (en) | 1947-09-06 | 1951-05-23 | Bataafsche Petroleum | A process for the preparation of dialdehydes and diols |
| US2546018A (en) | 1947-09-06 | 1951-03-20 | Shell Dev | Production of glutaraldehyde and csubstituted glutaraldehyde from dihydro pyrans |
| CH545781A (cg-RX-API-DMAC7.html) | 1970-02-21 | 1974-02-15 | ||
| US4448977A (en) | 1978-11-17 | 1984-05-15 | Union Carbide Corporation | Stabilized acetal-acid compositions |
| US4244876A (en) | 1978-11-17 | 1981-01-13 | Union Carbide Corporation | Acetal-acid compositions |
| SU878760A1 (ru) * | 1979-08-13 | 1981-11-07 | Армянский Филиал Ордена Трудового Красного Знамени Всесоюзного Научно-Исследовательского Института Химических Реактивов И Особо Чистых Веществ | Способ получени глутарового альдегида |
| JPS59108734A (ja) * | 1982-12-13 | 1984-06-23 | Daicel Chem Ind Ltd | グルタルアルデヒドの製造方法 |
| JP3289464B2 (ja) | 1994-02-10 | 2002-06-04 | 日本電信電話株式会社 | 高周波高出力トランジスタ |
| JP3415277B2 (ja) * | 1994-08-01 | 2003-06-09 | ダイセル化学工業株式会社 | グルタルアルデヒドの製造方法 |
| DE4429262A1 (de) * | 1994-08-18 | 1996-02-22 | Basf Ag | Verfahren zur Herstellung von Glutardialdehyd |
| DE4444709A1 (de) | 1994-12-15 | 1996-06-20 | Basf Ag | Verfahren zur Herstellung von Glutardialdehyd |
| WO1999023088A1 (en) | 1997-11-04 | 1999-05-14 | Union Carbide Chemicals & Plastics Technology Corporation | Vinyl ether derivatives |
| DE102004004716A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Isomerisierung von cis-2-Pentennitril zu 3-Pentennitril in einer Reaktivdestillation |
-
2009
- 2009-06-09 CN CN2009801226125A patent/CN102066302B/zh not_active Expired - Fee Related
- 2009-06-09 WO PCT/US2009/046730 patent/WO2009155169A1/en not_active Ceased
- 2009-06-09 BR BRPI0910026A patent/BRPI0910026A2/pt active Search and Examination
- 2009-06-09 US US12/481,181 patent/US7709686B2/en not_active Expired - Fee Related
- 2009-06-09 JP JP2011514698A patent/JP5576366B2/ja not_active Expired - Fee Related
- 2009-06-09 RU RU2011101714/04A patent/RU2495019C2/ru not_active IP Right Cessation
- 2009-06-09 AU AU2009260402A patent/AU2009260402B2/en not_active Ceased
- 2009-06-09 EP EP09767479.0A patent/EP2300406B1/en not_active Not-in-force
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6559346B1 (en) * | 1999-08-30 | 2003-05-06 | Basf Aktiengesellschaft | Method for the continuous production of glutaraldehyde |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2495019C2 (ru) | 2013-10-10 |
| CN102066302A (zh) | 2011-05-18 |
| JP5576366B2 (ja) | 2014-08-20 |
| EP2300406A1 (en) | 2011-03-30 |
| JP2011524910A (ja) | 2011-09-08 |
| BRPI0910026A2 (pt) | 2015-12-29 |
| CN102066302B (zh) | 2013-11-20 |
| EP2300406B1 (en) | 2016-12-07 |
| AU2009260402A1 (en) | 2009-12-23 |
| RU2011101714A (ru) | 2012-07-27 |
| WO2009155169A1 (en) | 2009-12-23 |
| US20090318735A1 (en) | 2009-12-24 |
| US7709686B2 (en) | 2010-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |