CA2377004A1 - New process for the purification of aldehyde impurities - Google Patents
New process for the purification of aldehyde impurities Download PDFInfo
- Publication number
- CA2377004A1 CA2377004A1 CA002377004A CA2377004A CA2377004A1 CA 2377004 A1 CA2377004 A1 CA 2377004A1 CA 002377004 A CA002377004 A CA 002377004A CA 2377004 A CA2377004 A CA 2377004A CA 2377004 A1 CA2377004 A1 CA 2377004A1
- Authority
- CA
- Canada
- Prior art keywords
- poloxamer
- process according
- acid
- solvent
- aldehydes
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 238000000746 purification Methods 0.000 title claims abstract description 17
- 239000012535 impurity Substances 0.000 title claims abstract description 11
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title abstract 3
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims abstract description 65
- 229920001983 poloxamer Polymers 0.000 claims abstract description 56
- 229960000502 poloxamer Drugs 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 229920001992 poloxamer 407 Polymers 0.000 claims abstract description 19
- 229940044476 poloxamer 407 Drugs 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 229920001993 poloxamer 188 Polymers 0.000 claims abstract description 15
- 229940044519 poloxamer 188 Drugs 0.000 claims abstract description 15
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 46
- 150000001299 aldehydes Chemical class 0.000 claims description 32
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 20
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 20
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 20
- 239000012530 fluid Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000001307 helium Substances 0.000 claims description 7
- 229910052734 helium Inorganic materials 0.000 claims description 7
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000007738 vacuum evaporation Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 8
- 230000003247 decreasing effect Effects 0.000 description 7
- 239000007921 spray Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- FVUIVHPWPXJLKV-UHFFFAOYSA-N acetaldehyde;formaldehyde;propanal Chemical compound O=C.CC=O.CCC=O FVUIVHPWPXJLKV-UHFFFAOYSA-N 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- PHOLIFLKGONSGY-CSKARUKUSA-N (e)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazine Chemical compound C1=CC=C2S\C(=N\N)N(C)C2=C1 PHOLIFLKGONSGY-CSKARUKUSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9902364-0 | 1999-06-21 | ||
| SE9902364A SE9902364D0 (sv) | 1999-06-21 | 1999-06-21 | New process |
| PCT/SE2000/001305 WO2000078841A1 (en) | 1999-06-21 | 2000-06-19 | New process for the purification of aldehyde impurities |
| US09/656,036 US6448371B1 (en) | 1999-06-21 | 2000-09-08 | Process for the purification of aldehyde impurities |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2377004A1 true CA2377004A1 (en) | 2000-12-28 |
Family
ID=26663601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002377004A Abandoned CA2377004A1 (en) | 1999-06-21 | 2000-06-19 | New process for the purification of aldehyde impurities |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6448371B1 (https=) |
| EP (1) | EP1192204B1 (https=) |
| JP (1) | JP2003503517A (https=) |
| CN (1) | CN1139615C (https=) |
| AT (1) | ATE312863T1 (https=) |
| AU (1) | AU765560B2 (https=) |
| BR (1) | BR0011815B1 (https=) |
| CA (1) | CA2377004A1 (https=) |
| DE (1) | DE60024821T2 (https=) |
| DK (1) | DK1192204T3 (https=) |
| ES (1) | ES2254200T3 (https=) |
| IL (1) | IL146746A0 (https=) |
| MX (1) | MXPA01013369A (https=) |
| NO (1) | NO318915B1 (https=) |
| NZ (1) | NZ515954A (https=) |
| SE (1) | SE9902364D0 (https=) |
| WO (1) | WO2000078841A1 (https=) |
| ZA (1) | ZA200109740B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040266983A1 (en) * | 2000-08-17 | 2004-12-30 | Reeve Lorraine E | Purified polyoxyalkylene block copolymers |
| ES2260437T3 (es) * | 2001-05-01 | 2006-11-01 | UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY CORPORATION | Composicion farmaceutica que comprende poli(oxidos de alquileno) que tienen cantidades reducidas de compuestos formicos. |
| WO2003092649A2 (en) * | 2002-04-29 | 2003-11-13 | Alza Corporation | Reduced formate poly(alkylene oxides) with secondary amines for reducing impurity formation |
| JP2005343964A (ja) * | 2004-06-01 | 2005-12-15 | Otsuka Pharmaceut Factory Inc | ポリアルキレングリコール類含有水溶液、及びその調製方法 |
| KR101343040B1 (ko) * | 2010-12-28 | 2013-12-18 | 주식회사 삼양바이오팜 | 정제된 폴록사머 및 그의 정제방법 |
| JP2013237638A (ja) * | 2012-05-15 | 2013-11-28 | Lion Corp | 眼科組成物 |
| KR102525493B1 (ko) | 2014-07-07 | 2023-04-25 | 라이프래프트 바이오사이언시즈 인코포레이티드 | 장기 순환 물질이 없는 폴록사머 조성물 및 이의 제조 방법 및 용도 |
| KR102723605B1 (ko) | 2015-12-22 | 2024-10-29 | 바스프 에스이 | 폴리에테르 블록 공중합체의 정제 방법 |
| CN110139887B (zh) * | 2017-01-06 | 2022-03-08 | 三洋化成工业株式会社 | 聚醚多元醇的制造方法和聚氨酯泡沫的制造方法 |
| WO2018145949A1 (en) | 2017-02-09 | 2018-08-16 | Basf Se | A process for purification of polyether block copolymers |
| KR20200100108A (ko) | 2017-12-20 | 2020-08-25 | 바스프 에스이 | 양친매성 그라프트 공중합체를 세포 배양 시약으로 이용하여 세포 배양 시스템을 안정화하는 방법 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036130A (en) * | 1957-09-10 | 1962-05-22 | Wyandotte Chemicals Corp | Mixtures of novel conjugated polyoxyethylene-polyoxypropylene compounds |
| US3462379A (en) * | 1965-12-02 | 1969-08-19 | Dow Chemical Co | Purification of poly(alkylene oxides) |
| US3546321A (en) * | 1967-02-08 | 1970-12-08 | Hercules Inc | Polyether graft copolymers |
| US3639574A (en) * | 1967-10-25 | 1972-02-01 | Basf Wyandotte Corp | Stable hydrogen peroxide gels |
| US3715402A (en) * | 1969-08-08 | 1973-02-06 | Basf Wyandotte Corp | Removal of catalysts from polyols |
| US3674502A (en) * | 1969-09-05 | 1972-07-04 | Firmenich Inc | Nonringing beverages containing poly(oxyethylene) - poly(oxypropylene) - poly(oxyethylene) copolymers |
| DE2755089C3 (de) * | 1977-12-10 | 1982-05-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Reinigung von Rohpolyäthern |
| DE2854541A1 (de) * | 1978-12-16 | 1980-06-26 | Bayer Ag | Verfahren zur reinigung nichtionischer emulgatoren |
| US4410447A (en) * | 1980-11-12 | 1983-10-18 | Union Carbide Corporation | Low-foaming nonionic surfactants |
| US4606918A (en) * | 1983-08-22 | 1986-08-19 | Syntex (U.S.A.) Inc. | Polyoxypropylene-polyoxyethylene block polymer based adjuvants |
| US5342541A (en) * | 1989-03-29 | 1994-08-30 | The Dow Chemical Company | Purified hydroxy-functional polyether compounds |
| DE3913937A1 (de) * | 1989-04-27 | 1990-10-31 | Hoechst Ag | Verfahren zur reinigung von alkylenoxid-addukten |
| JPH0791389B2 (ja) * | 1989-05-17 | 1995-10-04 | 信越化学工業株式会社 | 精製されたポリエーテルシリコーン及びその製造方法 |
| US5095061A (en) * | 1990-07-13 | 1992-03-10 | The Dow Chemical Company | Process to reduce propenyl polyethers in hydroxyfunctional polyethers |
| US5268510A (en) * | 1992-10-08 | 1993-12-07 | Vista Chemical Company | Process for purification of alkoxylated alcohols |
| KR0145350B1 (ko) * | 1993-09-07 | 1998-07-15 | 사또오 아키오 | 폴리옥시알킬렌폴리올의 제조방법 |
| CA2174394A1 (en) * | 1995-06-12 | 1996-12-13 | Timothy L. Lambert | Process for preparing low unsaturation polyether polyols |
| US6166266A (en) * | 1998-11-12 | 2000-12-26 | Bp Amoco Corporation | Preparation of polyoxymethylene dimethyl ethers by catalytic conversion of dimethyl ether with formaldehyde formed by oxidation of methanol |
-
1999
- 1999-06-21 SE SE9902364A patent/SE9902364D0/xx unknown
-
2000
- 2000-06-19 MX MXPA01013369A patent/MXPA01013369A/es active IP Right Grant
- 2000-06-19 IL IL14674600A patent/IL146746A0/xx active IP Right Grant
- 2000-06-19 NZ NZ515954A patent/NZ515954A/en not_active IP Right Cessation
- 2000-06-19 BR BRPI0011815-0A patent/BR0011815B1/pt not_active IP Right Cessation
- 2000-06-19 CN CNB008093067A patent/CN1139615C/zh not_active Expired - Lifetime
- 2000-06-19 AU AU60343/00A patent/AU765560B2/en not_active Expired
- 2000-06-19 CA CA002377004A patent/CA2377004A1/en not_active Abandoned
- 2000-06-19 WO PCT/SE2000/001305 patent/WO2000078841A1/en not_active Ceased
- 2000-06-19 JP JP2001505595A patent/JP2003503517A/ja active Pending
- 2000-06-19 DK DK00946611T patent/DK1192204T3/da active
- 2000-06-19 ES ES00946611T patent/ES2254200T3/es not_active Expired - Lifetime
- 2000-06-19 EP EP00946611A patent/EP1192204B1/en not_active Expired - Lifetime
- 2000-06-19 DE DE60024821T patent/DE60024821T2/de not_active Expired - Lifetime
- 2000-06-19 AT AT00946611T patent/ATE312863T1/de not_active IP Right Cessation
- 2000-09-08 US US09/656,036 patent/US6448371B1/en not_active Expired - Lifetime
-
2001
- 2001-11-27 ZA ZA200109740A patent/ZA200109740B/en unknown
- 2001-12-20 NO NO20016297A patent/NO318915B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20016297D0 (no) | 2001-12-20 |
| BR0011815A (pt) | 2002-03-19 |
| NZ515954A (en) | 2003-05-30 |
| CN1139615C (zh) | 2004-02-25 |
| SE9902364D0 (sv) | 1999-06-21 |
| NO20016297L (no) | 2002-02-04 |
| EP1192204A1 (en) | 2002-04-03 |
| AU6034300A (en) | 2001-01-09 |
| BR0011815B1 (pt) | 2010-06-15 |
| AU765560B2 (en) | 2003-09-25 |
| DK1192204T3 (da) | 2006-02-20 |
| DE60024821T2 (de) | 2006-06-14 |
| ATE312863T1 (de) | 2005-12-15 |
| IL146746A0 (en) | 2002-07-25 |
| NO318915B1 (no) | 2005-05-23 |
| ZA200109740B (en) | 2003-03-03 |
| CN1357019A (zh) | 2002-07-03 |
| DE60024821D1 (de) | 2006-01-19 |
| WO2000078841A1 (en) | 2000-12-28 |
| JP2003503517A (ja) | 2003-01-28 |
| EP1192204B1 (en) | 2005-12-14 |
| ES2254200T3 (es) | 2006-06-16 |
| US6448371B1 (en) | 2002-09-10 |
| MXPA01013369A (es) | 2002-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |