NO321348B1 - Fremgangsmate for fremstilling av trimetylolpropan eller trmetyloletan. - Google Patents
Fremgangsmate for fremstilling av trimetylolpropan eller trmetyloletan. Download PDFInfo
- Publication number
- NO321348B1 NO321348B1 NO20015861A NO20015861A NO321348B1 NO 321348 B1 NO321348 B1 NO 321348B1 NO 20015861 A NO20015861 A NO 20015861A NO 20015861 A NO20015861 A NO 20015861A NO 321348 B1 NO321348 B1 NO 321348B1
- Authority
- NO
- Norway
- Prior art keywords
- tmp
- tme
- mcf
- bmlf
- acid
- Prior art date
Links
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 title claims abstract description 99
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 50
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003377 acid catalyst Substances 0.000 claims abstract description 16
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract description 16
- 239000006227 byproduct Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 238000000746 purification Methods 0.000 claims abstract description 13
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 229910001868 water Inorganic materials 0.000 claims description 24
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 16
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000001241 acetals Chemical class 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003729 cation exchange resin Substances 0.000 claims description 8
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical group CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 4
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- WDEVXRIFJZNMKM-UHFFFAOYSA-N 2-(propan-2-yloxymethoxy)propane Chemical compound CC(C)OCOC(C)C WDEVXRIFJZNMKM-UHFFFAOYSA-N 0.000 claims description 2
- DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 claims description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 2
- 125000006091 1,3-dioxolane group Chemical group 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract description 22
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 2
- -1 ethylene glycol Chemical compound 0.000 abstract 1
- 238000004817 gas chromatography Methods 0.000 description 18
- 238000010306 acid treatment Methods 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000004457 water analysis Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- HILNBNGLDIFMAH-UHFFFAOYSA-N 1,3-dioxan-5-ylmethanol Chemical compound OCC1COCOC1 HILNBNGLDIFMAH-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000006223 plastic coating Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
- Cleaning Or Drying Semiconductors (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/324,435 US6096905A (en) | 1999-06-01 | 1999-06-01 | Treatment of a composition comprising a trimethylolalkane bis-monolinear formal |
| PCT/US2000/014643 WO2000073250A1 (en) | 1999-06-01 | 2000-05-26 | Treatment of a composition comprising a trimetlylohalkane bis-monolinear formal |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20015861L NO20015861L (no) | 2001-11-30 |
| NO20015861D0 NO20015861D0 (no) | 2001-11-30 |
| NO321348B1 true NO321348B1 (no) | 2006-05-02 |
Family
ID=23263574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20015861A NO321348B1 (no) | 1999-06-01 | 2001-11-30 | Fremgangsmate for fremstilling av trimetylolpropan eller trmetyloletan. |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6096905A (es) |
| EP (1) | EP1181263B1 (es) |
| JP (1) | JP5069388B2 (es) |
| KR (1) | KR100748797B1 (es) |
| CN (1) | CN1217896C (es) |
| AT (1) | ATE276221T1 (es) |
| AU (1) | AU762408B2 (es) |
| BR (1) | BR0010837B1 (es) |
| CA (1) | CA2373974C (es) |
| CZ (1) | CZ20014303A3 (es) |
| DE (1) | DE60013814T2 (es) |
| ES (1) | ES2226849T3 (es) |
| HU (1) | HUP0201517A3 (es) |
| MX (1) | MXPA01012324A (es) |
| NO (1) | NO321348B1 (es) |
| NZ (1) | NZ515480A (es) |
| RU (1) | RU2247704C2 (es) |
| WO (1) | WO2000073250A1 (es) |
| ZA (1) | ZA200109382B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6096905A (en) * | 1999-06-01 | 2000-08-01 | Celanese International Corporation | Treatment of a composition comprising a trimethylolalkane bis-monolinear formal |
| DE10223054A1 (de) * | 2002-05-24 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von Polyetherolen |
| DE10223055A1 (de) * | 2002-05-24 | 2003-12-11 | Basf Ag | Verfahren zur Herstellung von Polyesterpolyolen mehrwertiger Alkohole |
| DE10234016A1 (de) * | 2002-07-26 | 2004-02-05 | Basf Ag | Verfahren zur Ausbeuteerhöhung bei der Herstellung von mehrwertigen Alkoholen durch Spaltung acetalhaltiger Nebenprodukte |
| SE525080C2 (sv) * | 2003-03-21 | 2004-11-23 | Perstorp Specialty Chem Ab | Förfarande för framställning av en allyleter |
| CN101092410B (zh) * | 2007-05-21 | 2010-04-14 | 吉化集团公司 | 用三羟甲基丙烷重质残液制备环状三羟甲基丙烷缩甲醛的方法及设备 |
| CN100534967C (zh) * | 2007-06-12 | 2009-09-02 | 无锡百川化工股份有限公司 | 烷氧基化三羟甲基丙烷的生产方法 |
| CN101239320B (zh) * | 2008-01-17 | 2010-11-17 | 复旦大学 | 用于合成戊二醛的含钨超大介孔泡沫催化剂及其制造方法 |
| CN101671233B (zh) * | 2009-09-14 | 2012-12-12 | 无锡百川化工股份有限公司 | 一种生产甲酸钠的方法 |
| JP2012041310A (ja) * | 2010-08-20 | 2012-03-01 | Hitachi Chem Co Ltd | ヒドロキシアルキル（メタ）アクリル酸エステルの製造方法 |
| DE102011118993A1 (de) * | 2011-11-19 | 2013-05-23 | Oxea Gmbh | Verfahren zur Gewinnung von Di-Trimethylpropan und mit Trimethylpropan angereicherten Produktströmen aus den Nebenströmen der Trimethylolpropanherstellung |
| JP6321656B2 (ja) * | 2012-09-17 | 2018-05-09 | オクシア・ビショップ・エルエルシー | 精製残留物からのトリメチロールプロパンの回収 |
| US8921618B2 (en) | 2012-09-17 | 2014-12-30 | Oxea Bishop Llc | Recovery of trimethylolpropane from purification residue |
| US8759593B2 (en) | 2012-09-17 | 2014-06-24 | Oxea Bishop Llc | Recovery of alcohols from purification residue |
| RU2616004C1 (ru) * | 2016-03-10 | 2017-04-12 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Способ переработки высококипящих побочных продуктов процесса получения этриола |
| CN115850028A (zh) * | 2022-12-16 | 2023-03-28 | 赤峰瑞阳化工有限公司 | 一种三羟甲基丙烷多塔串联萃取精馏除杂精制的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE142184C (es) * | ||||
| US3076854A (en) * | 1955-12-05 | 1963-02-05 | Heyden Newport Chemical Corp | Recovery of trimethylolpropane |
| JPS509B1 (es) * | 1969-11-28 | 1975-01-06 | ||
| JPS4924043B1 (es) * | 1969-11-29 | 1974-06-20 | ||
| DD142184A1 (de) * | 1979-02-27 | 1980-06-11 | Helmut Dietze | Gewinnung von trimethylolpropan |
| DD287250A5 (de) * | 1989-08-21 | 1991-02-21 | Veb Leuna-Werke "Walter Ulbricht",De | Verfahren zur gewinnung von trimethylolpropan |
| DD287251A5 (de) * | 1989-08-21 | 1991-02-21 | Veb Leuna-Werke "Walter Ulbricht",De | Verfahren zur gewinnung von trimethylolpropan |
| SE9502355L (sv) * | 1995-06-29 | 1996-12-30 | Perstorp Ab | Spaltning av cykloalkyletrar |
| US6096905A (en) * | 1999-06-01 | 2000-08-01 | Celanese International Corporation | Treatment of a composition comprising a trimethylolalkane bis-monolinear formal |
-
1999
- 1999-06-01 US US09/324,435 patent/US6096905A/en not_active Expired - Lifetime
-
2000
- 2000-05-26 CA CA002373974A patent/CA2373974C/en not_active Expired - Fee Related
- 2000-05-26 JP JP2000621318A patent/JP5069388B2/ja not_active Expired - Fee Related
- 2000-05-26 WO PCT/US2000/014643 patent/WO2000073250A1/en active Application Filing
- 2000-05-26 ES ES00936359T patent/ES2226849T3/es not_active Expired - Lifetime
- 2000-05-26 MX MXPA01012324A patent/MXPA01012324A/es active IP Right Grant
- 2000-05-26 NZ NZ515480A patent/NZ515480A/en not_active IP Right Cessation
- 2000-05-26 CZ CZ20014303A patent/CZ20014303A3/cs unknown
- 2000-05-26 CN CN008083681A patent/CN1217896C/zh not_active Expired - Fee Related
- 2000-05-26 EP EP00936359A patent/EP1181263B1/en not_active Expired - Lifetime
- 2000-05-26 DE DE60013814T patent/DE60013814T2/de not_active Expired - Lifetime
- 2000-05-26 HU HU0201517A patent/HUP0201517A3/hu unknown
- 2000-05-26 KR KR1020017015332A patent/KR100748797B1/ko not_active IP Right Cessation
- 2000-05-26 RU RU2001135811/04A patent/RU2247704C2/ru not_active IP Right Cessation
- 2000-05-26 US US09/579,743 patent/US6316679B1/en not_active Expired - Lifetime
- 2000-05-26 AU AU51683/00A patent/AU762408B2/en not_active Ceased
- 2000-05-26 BR BRPI0010837-5A patent/BR0010837B1/pt not_active IP Right Cessation
- 2000-05-26 AT AT00936359T patent/ATE276221T1/de not_active IP Right Cessation
-
2001
- 2001-11-14 ZA ZA200109382A patent/ZA200109382B/en unknown
- 2001-11-30 NO NO20015861A patent/NO321348B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU762408B2 (en) | 2003-06-26 |
| AU5168300A (en) | 2000-12-18 |
| ES2226849T3 (es) | 2005-04-01 |
| NZ515480A (en) | 2003-08-29 |
| BR0010837B1 (pt) | 2010-11-03 |
| CZ20014303A3 (cs) | 2002-05-15 |
| BR0010837A (pt) | 2002-03-05 |
| CN1217896C (zh) | 2005-09-07 |
| HUP0201517A2 (en) | 2002-08-28 |
| MXPA01012324A (es) | 2002-07-22 |
| DE60013814T2 (de) | 2005-09-29 |
| US6096905A (en) | 2000-08-01 |
| WO2000073250A1 (en) | 2000-12-07 |
| EP1181263B1 (en) | 2004-09-15 |
| RU2247704C2 (ru) | 2005-03-10 |
| JP5069388B2 (ja) | 2012-11-07 |
| US6316679B1 (en) | 2001-11-13 |
| JP2003500463A (ja) | 2003-01-07 |
| KR20020003400A (ko) | 2002-01-12 |
| CA2373974C (en) | 2008-07-08 |
| NO20015861L (no) | 2001-11-30 |
| CA2373974A1 (en) | 2000-12-07 |
| DE60013814D1 (de) | 2004-10-21 |
| CN1353682A (zh) | 2002-06-12 |
| EP1181263A1 (en) | 2002-02-27 |
| ZA200109382B (en) | 2002-12-17 |
| ATE276221T1 (de) | 2004-10-15 |
| HUP0201517A3 (en) | 2003-08-28 |
| NO20015861D0 (no) | 2001-11-30 |
| KR100748797B1 (ko) | 2007-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO321348B1 (no) | Fremgangsmate for fremstilling av trimetylolpropan eller trmetyloletan. | |
| JP2000191568A (ja) | 高純度トリメチロ―ルプロパンの製造法 | |
| EP3008046B1 (en) | Process for the manufacture of epoxy-monomers and epoxides | |
| CA2951930C (en) | Process for producing low voc coalescing aids | |
| TWI843779B (zh) | 製備碳酸二烷酯及烷二醇之方法 | |
| US4675082A (en) | Recovery of propylene glycol mono t-butoxy ether | |
| NL8202030A (nl) | Werkwijze voor de bereiding van carbonzuuresters uit onverzadigde en meerwaardige alcoholen. | |
| US4547583A (en) | Process for esterifying phenol-containing carboxylic acids | |
| CN103097372A (zh) | 用于生产二氧戊环的方法 | |
| US6494996B2 (en) | Process for removing water from aqueous methanol | |
| KR100532269B1 (ko) | 알킬렌 글리콜 모노알킬 에테르의 카르복실산 에스테르의연속적인 제조방법 | |
| AU2002301312B2 (en) | Treatment of a composition comprising a trimethylolalkane bis-monolinear formal | |
| RU2186053C2 (ru) | Способ получения моноэтиленгликоля волоконной чистоты | |
| US4695410A (en) | Recovery of phenol from aqueous solution | |
| EP0101620A2 (en) | Production of low color refined isophorone | |
| JPS6377841A (ja) | アクリル酸又はメタクリル酸のフエニルエステル類の製法 | |
| SU1006425A1 (ru) | Способ получени концентрированных водных растворов формальдегида | |
| JP2003238480A (ja) | エチレングリコールの回収蒸留釜残の処理方法 | |
| WO2013005636A1 (ja) | ジトリメチロールプロパンの製造方法 | |
| JPH10158203A (ja) | ブタンジオールの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |