JP4471976B2 - アンモニアとエチレンオキサイドとの反応により得られる混合物からのトリエタノールアミンの分離方法 - Google Patents
アンモニアとエチレンオキサイドとの反応により得られる混合物からのトリエタノールアミンの分離方法 Download PDFInfo
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- JP4471976B2 JP4471976B2 JP2006530076A JP2006530076A JP4471976B2 JP 4471976 B2 JP4471976 B2 JP 4471976B2 JP 2006530076 A JP2006530076 A JP 2006530076A JP 2006530076 A JP2006530076 A JP 2006530076A JP 4471976 B2 JP4471976 B2 JP 4471976B2
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- triethanolamine
- tea
- distillation
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 title claims abstract description 63
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 26
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 229910021529 ammonia Inorganic materials 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 title abstract description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 60
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000004821 distillation Methods 0.000 claims abstract description 24
- 238000009835 boiling Methods 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 238000005192 partition Methods 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 9
- 238000001944 continuous distillation Methods 0.000 claims description 2
- -1 ethanolamine ethers Chemical class 0.000 abstract description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 238000012856 packing Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001550224 Apha Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VARKIGWTYBUWNT-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanol Chemical compound OCCN1CCN(CCO)CC1 VARKIGWTYBUWNT-UHFFFAOYSA-N 0.000 description 1
- BZUDVELGTZDOIG-UHFFFAOYSA-N 2-ethyl-n,n-bis(2-ethylhexyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CC(CC)CCCC BZUDVELGTZDOIG-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 244000110556 Cyclopia subternata Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 239000003054 catalyst Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
図1は、以下の構成を含むプラントを概略的に示しており、そのプラントは、
(1)以下の(2)及び(3)を含む第1の塔、
(2)ストリッピング部、
(3)富化部(enrichment section)、
(4)流下薄膜型蒸発缶、
(5)第1の塔への供給管、
(6)頂部取り出し部、
(7)底部取り出し部、及び
(8)以下の(9)及び(10)を介して接続された第2の塔、
(9)第1の接続管、
(10)第1の塔への第2の接続管、
(11)純粋なTEAを取り出すための頂部取り出し部、を含み、
図2は、隔壁塔(12)を示しており、隔壁塔(12)は、
(13)以下の(14)及び(15)を形成する中央の隔壁、
(14)流入部、
(15)取り出し部、
(16)流下薄膜型蒸発缶、
(17)塔への供給管、
(18)頂部取り出し部、
(19)底部取り出し部、
(20)純粋なTEAを取り出すための側方取り出し部、及び
(21)DEAが豊富な低沸点流を取り出すための側方取り出し部、を備えている。
76.4%のTEA、22.4%のDEA、1.1%のエタノールアミンエーテル、0.02%の水及び0.1%のリン酸を含む340kg/時の供給混合物を、第1の塔(1)の供給点(5)から180℃の流入温度で液体の状態にて供給した。塔を、頂部において2ミリバールの圧力で運転した。塔の底部取り出し部(7)において、93%のTEAと6.9%のエタノールアミンエーテルとの50kg/時の混合物を190℃の温度で排出した。塔の底部における液体の滞留時間は約45分であった。塔の頂部取り出し部(6)から、67%のDEA、32.4%のTEA及び0.4%のエタノールアミンエーテルを含む120kg/時の混合物を排出し、出発混合物に戻した。流れの温度は99℃であり、還流比は0.2であった。240kg/時のTEAリッチ流(TEAが豊富に含まれる流れ)を第1の接続管(9)を介して気体の状態で取り出し、第2の塔(8)に供給した。
1800kgのTEA、490kgのDEA、20kgのエタノールアミンエーテル、500ppmの水及び500ppmのリン酸を含む2300kg/時の混合物を、供給管(17)によって図2に示されているような隔壁塔(12)に供給した。塔を、3ミリバールの頂部圧力で運転した。流入温度は約100℃であった。約2400kg/時のDEAリッチ流(DEAが豊富に含まれる流れ)を、頂部取り出し部(18)から取り出した。この流れの約800kg/時を、DEA後処理部に再循環させた。残りの1600kg/時をランバックとして隔壁塔に戻したが、半分は流入部(14)へ行き、半分は取り出し部(15)に行った。約450kg/時の高沸点成分が塔の底部で凝集し、これを底部取り出し部(19)から190℃の温度で排出した。TEAを隔壁塔(12)の取り出し部(15)で濃縮し、側方取り出し部(20)を介して1050kg/時の速度で液体の状態にて取り出した。99.5%の純度を有するTEAを得た。DEA含有率は0.1%であった。
(2)ストリッピング部
(3)富化部(enrichment section)
(4)流下薄膜型蒸発缶
(5)第1の塔への供給管
(6)頂部取り出し部
(7)底部取り出し部
(8)第2の塔
(9)第1の接続管
(10)第1の塔への第2の接続管
(11)純粋なTEAを取り出すための頂部取り出し部
(13)中央の隔壁
(14)流入部
(15)取り出し部
(16)流下薄膜型蒸発缶
(17)塔への供給管
(18)頂部取り出し部
(19)底部取り出し部
(20)純粋なTEAを取り出すための側方取り出し部
(21)DEAが豊富な低沸点流を取り出すための側方取り出し部
Claims (4)
- アンモニアとエチレンオキサイドとを過圧及び高温条件下に液相中で反応させることにより得られる、モノエタノールアミン、ジエタノールアミン及びトリエタノールアミンの混合物と、エタノールアミンエーテル及び水とから連続的に蒸留することによってトリエタノールアミンを分離する方法であって、
混合物を2段階で蒸留する工程を含み、且つ第1段階で、低沸点留分及び高沸点留分を取り出して、排出し、そして第2段階で、中位の沸点の留分を蒸留することにより、99.4質量%を超えるトリエタノールアミンと0.2質量%未満のジエタノールアミンを含む生成物を得ることを特徴とするトリエタノールアミンの分離方法。 - 混合物の蒸留が第1の塔と該第1の塔に接続されている第2の塔で行われる請求項1に記載の方法。
- 混合物を2段階で蒸留する工程を、流入部と取り出し部とに分割する縦方向の隔壁を有する隔壁塔において、第1段階を流入部で行い、第2段階を取り出し部で行う請求項1に記載の方法。
- 混合物を隔壁塔において隔壁の中央の領域に供給し、隔壁塔からトリエタノールアミンを排出する請求項3に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10346779A DE10346779A1 (de) | 2003-10-08 | 2003-10-08 | Verfahren zur Abtrennung von Triethanolamin aus einem durch die Umsetzung von Ammoniak mit Ethylenoxid erhaltenen Stoffgemisch |
PCT/EP2004/011022 WO2005035481A2 (de) | 2003-10-08 | 2004-10-02 | Verfahren zur abtrennung von triethanolamin aus einem durch die umsetzung von ammoniak mit ethylenoxid erhaltenen stoffgemisch |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007508257A JP2007508257A (ja) | 2007-04-05 |
JP4471976B2 true JP4471976B2 (ja) | 2010-06-02 |
Family
ID=34428244
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006530076A Active JP4471976B2 (ja) | 2003-10-08 | 2004-10-02 | アンモニアとエチレンオキサイドとの反応により得られる混合物からのトリエタノールアミンの分離方法 |
Country Status (13)
Country | Link |
---|---|
US (1) | US7279602B2 (ja) |
EP (1) | EP1675816B1 (ja) |
JP (1) | JP4471976B2 (ja) |
KR (1) | KR101036382B1 (ja) |
CN (1) | CN100364960C (ja) |
AT (1) | ATE365153T1 (ja) |
CA (1) | CA2540246C (ja) |
DE (2) | DE10346779A1 (ja) |
ES (1) | ES2286669T3 (ja) |
MX (1) | MXPA06003484A (ja) |
MY (1) | MY138351A (ja) |
TW (1) | TWI331989B (ja) |
WO (1) | WO2005035481A2 (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101139296B (zh) * | 2007-09-29 | 2010-05-26 | 吴兆立 | 增设气提拔头段的乙醇胺蒸馏的方法 |
US8674140B2 (en) | 2008-09-17 | 2014-03-18 | Basf Se | Devices and method for continuous distillative separation of a mixture containing one or more alkanolamine(s) |
US8466323B2 (en) | 2008-12-19 | 2013-06-18 | Basf Se | Process for preparing pure triethanolamine (TEOA) |
EP2794581B1 (en) | 2011-12-22 | 2016-05-25 | Dow Global Technologies LLC | Reductive amination of diethanolamine and resulting product mixture |
CN103271238B (zh) * | 2013-05-10 | 2014-04-02 | 中国科学院亚热带农业生态研究所 | 一种饲料添加剂一乙醇胺的制备方法及应用 |
CN106132920A (zh) * | 2014-04-04 | 2016-11-16 | 沙特基础工业全球技术有限公司 | 最小化乙醇胺产物流股中的水含量 |
CN106164043A (zh) * | 2014-04-08 | 2016-11-23 | 沙特基础工业全球技术有限公司 | 最小化乙醇胺产物流股中的水含量 |
EP3148965A1 (en) | 2014-05-27 | 2017-04-05 | SABIC Global Technologies B.V. | Production of tea 85% directly without blending with pure cut of dea 99% |
CN106414395A (zh) | 2014-05-30 | 2017-02-15 | 沙特基础工业全球技术有限公司 | 通过降低三乙醇胺塔处的温度改善乙醇胺产物流的质量和颜色 |
EP3386943B1 (en) | 2015-12-11 | 2024-01-03 | SABIC Global Technologies B.V. | Methods of reducing color in alkanolamine compositions |
WO2017115256A1 (en) | 2015-12-29 | 2017-07-06 | Sabic Global Technologies B.V. | Methods of reducing color in alkanolamine compositions and compositions produced thereby |
CN114276255A (zh) * | 2021-12-17 | 2022-04-05 | 湖北仙粼化工有限公司 | 一种乙醇胺多段管式反应节能生产系统及生产工艺 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1968512A (en) * | 1931-12-07 | 1934-07-31 | Carbide & Carbon Chem Corp | Process for purifying liquids |
US3453183A (en) * | 1964-12-29 | 1969-07-01 | Nippon Catalytic Chem Ind | Method of purifying ethanolamines |
US3742059A (en) * | 1971-05-24 | 1973-06-26 | Dow Chemical Co | Color-stabilized alkanolamines |
IT967651B (it) * | 1972-09-20 | 1974-03-11 | Sir Soc Italiana Resine Spa | Perfezionamenti nei procedimenti per la preparazione di etanolam mine |
US4381223A (en) * | 1981-09-30 | 1983-04-26 | Union Carbide Corporation | Process for the treatment of organic amine compositions |
JPS6219558A (ja) | 1985-07-19 | 1987-01-28 | Mitsui Toatsu Chem Inc | 安定化高品質トリエタノ−ルアミンの製造方法 |
US4673762A (en) * | 1986-05-27 | 1987-06-16 | Texaco Inc. | Decolorizing ethanolamines with alkylene oxides |
FR2804109B1 (fr) * | 2000-01-24 | 2002-08-16 | Bp Chemicals Snc | Procede de fabrication en continu de triethanolamine, et produit obtenu |
DE10011942A1 (de) * | 2000-03-11 | 2001-09-13 | Basf Ag | Verfahren zur Herstellung von Alkanolaminen mit verbesserter Farbqualität |
TWI303242B (en) * | 2003-02-03 | 2008-11-21 | Nippon Catalytic Chem Ind | Process for producing high purity trialkanolamine |
-
2003
- 2003-10-08 DE DE10346779A patent/DE10346779A1/de not_active Withdrawn
-
2004
- 2004-09-23 MY MYPI20043895A patent/MY138351A/en unknown
- 2004-09-30 TW TW093129661A patent/TWI331989B/zh not_active IP Right Cessation
- 2004-10-02 WO PCT/EP2004/011022 patent/WO2005035481A2/de active IP Right Grant
- 2004-10-02 MX MXPA06003484A patent/MXPA06003484A/es active IP Right Grant
- 2004-10-02 AT AT04765773T patent/ATE365153T1/de active
- 2004-10-02 EP EP04765773A patent/EP1675816B1/de active Active
- 2004-10-02 JP JP2006530076A patent/JP4471976B2/ja active Active
- 2004-10-02 KR KR1020067006826A patent/KR101036382B1/ko active IP Right Grant
- 2004-10-02 CN CNB2004800295290A patent/CN100364960C/zh active Active
- 2004-10-02 CA CA2540246A patent/CA2540246C/en not_active Expired - Fee Related
- 2004-10-02 US US10/573,498 patent/US7279602B2/en active Active
- 2004-10-02 ES ES04765773T patent/ES2286669T3/es active Active
- 2004-10-02 DE DE502004004156T patent/DE502004004156D1/de active Active
Also Published As
Publication number | Publication date |
---|---|
ATE365153T1 (de) | 2007-07-15 |
KR101036382B1 (ko) | 2011-05-23 |
WO2005035481A3 (de) | 2005-06-02 |
US7279602B2 (en) | 2007-10-09 |
EP1675816B1 (de) | 2007-06-20 |
TWI331989B (en) | 2010-10-21 |
DE502004004156D1 (de) | 2007-08-02 |
CA2540246A1 (en) | 2005-04-21 |
KR20060120026A (ko) | 2006-11-24 |
ES2286669T3 (es) | 2007-12-01 |
MXPA06003484A (es) | 2006-06-08 |
WO2005035481A2 (de) | 2005-04-21 |
EP1675816A2 (de) | 2006-07-05 |
DE10346779A1 (de) | 2005-05-12 |
MY138351A (en) | 2009-05-29 |
CN1863761A (zh) | 2006-11-15 |
US20060293541A1 (en) | 2006-12-28 |
CN100364960C (zh) | 2008-01-30 |
CA2540246C (en) | 2011-06-07 |
JP2007508257A (ja) | 2007-04-05 |
TW200523233A (en) | 2005-07-16 |
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