JP2012511534A5 - - Google Patents
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- Publication number
- JP2012511534A5 JP2012511534A5 JP2011540042A JP2011540042A JP2012511534A5 JP 2012511534 A5 JP2012511534 A5 JP 2012511534A5 JP 2011540042 A JP2011540042 A JP 2011540042A JP 2011540042 A JP2011540042 A JP 2011540042A JP 2012511534 A5 JP2012511534 A5 JP 2012511534A5
- Authority
- JP
- Japan
- Prior art keywords
- polymethylol
- column
- distillation
- evaporator
- temperature
- 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.)
- Granted
Links
- 238000004821 distillation Methods 0.000 claims description 34
- 238000001704 evaporation Methods 0.000 claims description 27
- 230000008020 evaporation Effects 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 13
- 150000003512 tertiary amines Chemical class 0.000 claims description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000005575 aldol reaction Methods 0.000 claims description 3
- -1 amine formates Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 claims 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000003541 multi-stage reaction Methods 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- 229930000044 secondary metabolite Natural products 0.000 claims 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- 238000012856 packing Methods 0.000 description 12
- 239000011552 falling film Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 9
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 5
- JJMOMMLADQPZNY-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanal Chemical compound OCC(C)(C)C=O JJMOMMLADQPZNY-UHFFFAOYSA-N 0.000 description 4
- 238000003491 array Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000004065 wastewater treatment Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- APUQIHKCZFWODD-UHFFFAOYSA-N hydroxymethyl formate Chemical compound OCOC=O APUQIHKCZFWODD-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- YYKMQUOJKCKTSD-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanal Chemical compound CCC(CO)(CO)C=O YYKMQUOJKCKTSD-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- 229910000851 Alloy steel Inorganic materials 0.000 description 1
- HSYWLFXQDVFKGD-UHFFFAOYSA-N CC[O](C)N(C)C Chemical compound CC[O](C)N(C)C HSYWLFXQDVFKGD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08171040.2 | 2008-12-09 | ||
| EP08171040 | 2008-12-09 | ||
| PCT/EP2009/066522 WO2010066674A2 (de) | 2008-12-09 | 2009-12-07 | Verfahren zur herstellung von polymethylolen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012511534A JP2012511534A (ja) | 2012-05-24 |
| JP2012511534A5 true JP2012511534A5 (enExample) | 2013-01-31 |
| JP5783905B2 JP5783905B2 (ja) | 2015-09-24 |
Family
ID=42111165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011540042A Expired - Fee Related JP5783905B2 (ja) | 2008-12-09 | 2009-12-07 | ポリメチロールの製造方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8884076B2 (enExample) |
| EP (1) | EP2376413B2 (enExample) |
| JP (1) | JP5783905B2 (enExample) |
| KR (2) | KR20110094211A (enExample) |
| CN (1) | CN101747143B (enExample) |
| BR (1) | BRPI0923291B1 (enExample) |
| ES (1) | ES2599328T3 (enExample) |
| MY (1) | MY176941A (enExample) |
| RU (1) | RU2531613C2 (enExample) |
| SG (1) | SG171403A1 (enExample) |
| TW (1) | TWI494294B (enExample) |
| WO (1) | WO2010066674A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY153850A (en) | 2008-12-09 | 2015-03-31 | Basf Se | Method for purifying crude polymethylols |
| WO2010066674A2 (de) | 2008-12-09 | 2010-06-17 | Basf Se | Verfahren zur herstellung von polymethylolen |
| WO2010079187A1 (de) | 2009-01-12 | 2010-07-15 | Basf Se | Verfahren zur herstellung von polymethylolen |
| US8853465B2 (en) | 2010-05-12 | 2014-10-07 | Basf Se | Process for preparing neopentyl glycol |
| WO2013026758A1 (de) | 2011-08-23 | 2013-02-28 | Basf Se | Verfahren zur herstellung von neopentylglykol |
| DE102011118956A1 (de) * | 2011-11-19 | 2013-05-23 | Oxea Gmbh | Verfahren zur Gewinnung von Di-Trimethylolpropan und mit Trimethylolpropan angereicherten Produktströmen aus den Nebenströmen der Trimethylolpropanherstellung |
| DE102011118953B4 (de) * | 2011-11-19 | 2014-06-05 | Oxea Gmbh | Destillatives Verfahren zur Gewinnung von Di-Trimethylolpropan |
| US8710278B1 (en) | 2013-01-31 | 2014-04-29 | Eastman Chemical Company | Process for producing polyols |
| US9056824B2 (en) | 2013-01-31 | 2015-06-16 | Eastman Chemical Company | Preparation of hydroxy aldehydes |
| DE102014100996B4 (de) * | 2014-01-28 | 2018-11-15 | Oxea Gmbh | Verfahren zur Herstellung von Neopentylglykol |
| EP3580290B1 (en) * | 2017-02-07 | 2024-05-01 | PPG Industries Ohio, Inc. | Low-temperature curing coating compositions |
| KR102245932B1 (ko) | 2017-10-23 | 2021-04-28 | 주식회사 엘지화학 | 트리메틸올프로판의 제조방법 |
| CN109180428B (zh) * | 2018-08-06 | 2020-06-05 | 吉林市道特化工科技有限责任公司 | 一种2，2-二甲基-1，3-丙二醇的生产工艺 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU125552A1 (ru) * | 1959-03-03 | 1959-11-30 | Поблотивернер Винцер Хельмут | Способ очистки триметилолпропана |
| BE754868A (fr) | 1969-08-16 | 1971-02-15 | Basf Ag | Procede pour la mise en oeuvre de reactions exothermiques entreun gaz et un liquide |
| BE758910A (fr) | 1969-11-15 | 1971-05-13 | Basf Ag | Preparation de dimethyl-2, 2-propanediol-1, 3 |
| DE2040501C3 (de) | 1970-08-14 | 1984-01-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Durchführung von exothermen Reaktionen zwischen einem Gas und einer Flüssigkeit |
| DE2702582C3 (de) | 1977-01-22 | 1980-12-04 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Trimethylolalkanen |
| DE2813201A1 (de) | 1978-03-25 | 1979-10-04 | Bayer Ag | Verfahren zur herstellung von 2,2-dimethylolalkanalen |
| DE3027890A1 (de) | 1980-07-23 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | Hydrierkatalysatoren fuer die herstellung von propandiolen und verfahren zur herstellung von propandiolen mit solchen katalysatoren |
| US5532417A (en) | 1991-04-26 | 1996-07-02 | Aristech Chemical Corporation | Manufacture of neopentyl glycol (IV) |
| DE69218309T3 (de) * | 1991-06-28 | 2000-07-13 | Aristech Chemical Corp., Pittsburgh | Herstellung von Neopentylglykol (IV) |
| JP3175360B2 (ja) | 1992-12-10 | 2001-06-11 | 三菱化学株式会社 | １，４−ブタンジオールの精製方法 |
| ES2171539T3 (es) | 1994-05-19 | 2002-09-16 | Basf Ag | Procedimiento para la elaboracion de alcoholes. |
| JPH0987273A (ja) * | 1995-09-22 | 1997-03-31 | Mitsubishi Gas Chem Co Inc | ε−カプロラクトンの精製方法 |
| DE19542036A1 (de) | 1995-11-10 | 1997-05-15 | Basf Ag | Verfahren zur Herstellung von Polyalkoholen |
| DE19653093A1 (de) * | 1996-12-20 | 1998-06-25 | Basf Ag | Verfahren zur Herstellung von Polyalkoholen |
| DE19963437A1 (de) * | 1999-12-28 | 2001-07-05 | Basf Ag | Verfahren zur Zersetzung von bei der Synthese mehrwertiger Alkohole gebildeter hochsiedender Nebenprodukte |
| DE19963435A1 (de) * | 1999-12-28 | 2001-07-05 | Basf Ag | Verfahren zur Reinigung von durch Hydrierung hergestelltem Trimethylolpropan durch kontinuierliche Destillation |
| DE19963444A1 (de) * | 1999-12-28 | 2001-07-12 | Basf Ag | Verfahren zur Umwandlung von bei der Trimethylolalkan-Herstellung anfallendem Trimethylolalkanformiat |
| DE10058303A1 (de) | 2000-11-24 | 2002-05-29 | Basf Ag | Verfahren zur Reinigung von durch Hydrierung hergestelltem Trimethylolpropan durch Kombination einer kontinuierlichen Destillation mit einer Ionentauscherbehandlung |
| DE10160180A1 (de) * | 2001-12-07 | 2003-06-18 | Basf Ag | Verfahren zur Isolierung von Trimethylolpropan aus einem Reaktionsgemisch |
| DE10234016A1 (de) | 2002-07-26 | 2004-02-05 | Basf Ag | Verfahren zur Ausbeuteerhöhung bei der Herstellung von mehrwertigen Alkoholen durch Spaltung acetalhaltiger Nebenprodukte |
| DE102005032430A1 (de) * | 2005-07-12 | 2007-01-25 | Bayer Materialscience Ag | Verfahren zur Herstellung von Toluylendiamin |
| US7462747B2 (en) | 2007-01-05 | 2008-12-09 | Basf Aktiengesellschaft | Process for preparing polyalcohols from formaldehyde having a low formic acid content |
| JP2010518174A (ja) | 2007-02-15 | 2010-05-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 極めて純粋な１，４−ブタンジオールの製造方法 |
| CN101657397B (zh) | 2007-03-02 | 2013-04-10 | 巴斯夫欧洲公司 | 制备羟基新戊醛和新戊二醇的方法 |
| CN101675022B (zh) | 2007-03-23 | 2013-01-23 | 巴斯夫欧洲公司 | 通过蒸馏获得马来酸酐的方法 |
| JP2010529159A (ja) | 2007-06-14 | 2010-08-26 | ビーエーエスエフ ソシエタス・ヨーロピア | ε−カプロラクトンの製造法 |
| JP5453289B2 (ja) | 2007-11-05 | 2014-03-26 | ビーエーエスエフ ソシエタス・ヨーロピア | ε−カプロラクトンの製造方法 |
| WO2009080504A1 (de) | 2007-12-21 | 2009-07-02 | Basf Se | Verfahren zur herstellung epsilon-caprolacton |
| CA2714574A1 (en) | 2008-02-15 | 2009-08-20 | Basf Se | Process for preparing 6-hydroxycaproic esters |
| PL2310483T3 (pl) | 2008-07-07 | 2016-09-30 | Kompozycja enzymatyczna zawierająca cząstki polimerowe zawierające enzym | |
| US9174201B2 (en) | 2008-09-19 | 2015-11-03 | Basf Se | Method for the continuous production of an amine using an aluminum—copper catalyst |
| MY153850A (en) | 2008-12-09 | 2015-03-31 | Basf Se | Method for purifying crude polymethylols |
| WO2010066674A2 (de) | 2008-12-09 | 2010-06-17 | Basf Se | Verfahren zur herstellung von polymethylolen |
| WO2010079187A1 (de) * | 2009-01-12 | 2010-07-15 | Basf Se | Verfahren zur herstellung von polymethylolen |
-
2009
- 2009-12-07 WO PCT/EP2009/066522 patent/WO2010066674A2/de not_active Ceased
- 2009-12-07 ES ES09764533.7T patent/ES2599328T3/es active Active
- 2009-12-07 MY MYPI2011002442A patent/MY176941A/en unknown
- 2009-12-07 KR KR1020117015794A patent/KR20110094211A/ko not_active Ceased
- 2009-12-07 EP EP09764533.7A patent/EP2376413B2/de active Active
- 2009-12-07 KR KR1020177001598A patent/KR101773327B1/ko not_active Expired - Fee Related
- 2009-12-07 JP JP2011540042A patent/JP5783905B2/ja not_active Expired - Fee Related
- 2009-12-07 BR BRPI0923291-5A patent/BRPI0923291B1/pt not_active IP Right Cessation
- 2009-12-07 US US13/133,861 patent/US8884076B2/en active Active
- 2009-12-07 RU RU2011128047/04A patent/RU2531613C2/ru not_active IP Right Cessation
- 2009-12-07 SG SG2011037611A patent/SG171403A1/en unknown
- 2009-12-08 TW TW098141959A patent/TWI494294B/zh not_active IP Right Cessation
- 2009-12-09 CN CN200910258005.3A patent/CN101747143B/zh not_active Ceased
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