DE3608716A1 - Verfahren zur herstellung von polyoxyalkylen-polyaminen - Google Patents
Verfahren zur herstellung von polyoxyalkylen-polyaminenInfo
- Publication number
- DE3608716A1 DE3608716A1 DE19863608716 DE3608716A DE3608716A1 DE 3608716 A1 DE3608716 A1 DE 3608716A1 DE 19863608716 DE19863608716 DE 19863608716 DE 3608716 A DE3608716 A DE 3608716A DE 3608716 A1 DE3608716 A1 DE 3608716A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- molybdenum
- raney nickel
- weight
- aluminum
- 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.)
- Withdrawn
Links
- 229920000768 polyamine Polymers 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 57
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 56
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 49
- 229910052750 molybdenum Inorganic materials 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 35
- 239000011733 molybdenum Substances 0.000 claims description 34
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 31
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 24
- 229910021529 ammonia Inorganic materials 0.000 claims description 23
- 239000007868 Raney catalyst Substances 0.000 claims description 22
- 229910052782 aluminium Inorganic materials 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 6
- 238000006268 reductive amination reaction Methods 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- -1 aliphatic amines Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 229920001451 polypropylene glycol Polymers 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 150000003141 primary amines Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 239000011651 chromium Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 5
- 238000005576 amination reaction Methods 0.000 description 5
- 229910000838 Al alloy Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910000990 Ni alloy Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 229910001182 Mo alloy Inorganic materials 0.000 description 1
- 229910017318 Mo—Ni Inorganic materials 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000004000 hexols Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000013022 venting Methods 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
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
- C08G65/3255—Ammonia
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73959585A | 1985-05-31 | 1985-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3608716A1 true DE3608716A1 (de) | 1986-12-04 |
Family
ID=24973003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863608716 Withdrawn DE3608716A1 (de) | 1985-05-31 | 1986-03-15 | Verfahren zur herstellung von polyoxyalkylen-polyaminen |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS61278528A (enrdf_load_stackoverflow) |
| DE (1) | DE3608716A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2175910B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7696385B2 (en) | 2005-06-28 | 2010-04-13 | Clariant Produkte (Deutschland) Gmbh | Polyetheramine production method |
| US8071814B2 (en) | 2006-12-06 | 2011-12-06 | Clariant Finance (Bvi) Limited | Process for preparing polyetheramines |
| US8889814B2 (en) | 2006-08-03 | 2014-11-18 | Clariant Finance (Bvi) Limited | Polyetheramine macromonomers comprising two neighboring hydroxyl groups and their use for producing polyurethanes |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0273545A1 (en) * | 1987-01-02 | 1988-07-06 | Texaco Development Corporation | Novel reaction product and ORI-inhibited motor fuel composition |
| GB8819661D0 (en) * | 1988-08-18 | 1988-09-21 | Bp Chem Int Ltd | Novel compounds |
| GB8819663D0 (en) * | 1988-08-18 | 1988-09-21 | Bp Chem Int Ltd | Chemical process |
| JP2756000B2 (ja) * | 1989-08-25 | 1998-05-25 | 花王株式会社 | 第３級アミノアルコール及びその製造方法 |
| US4992590A (en) * | 1989-10-02 | 1991-02-12 | Texaco Chemical Company | Polyamines by amination of polyamino initiated polyoxyalkylene glycols |
| DE3941789A1 (de) * | 1989-12-19 | 1991-06-20 | Bayer Ag | Verfahren zur herstellung von aminopolyalkylenoxiden |
| FR2710856B1 (fr) * | 1993-10-07 | 1995-12-29 | Rhone Poulenc Chimie | Composition de matière utile comme catalyseur de type Raney, pour l'hydrogénation d'halogénonitroaromatiques en halogénoaminoaromatiques et procédé en faisant application. |
| DE19902942A1 (de) * | 1999-01-26 | 2000-07-27 | Creavis Tech & Innovation Gmbh | Aminofunktionalisierte Polyoxyalkane |
| JP2005048086A (ja) | 2003-07-30 | 2005-02-24 | Kao Corp | ポリオキシアルキレントリアミンの製造方法 |
| CN102336903A (zh) * | 2011-07-07 | 2012-02-01 | 中国石油化工集团公司 | 脂肪族聚醚胺生产工艺 |
| CN102408559A (zh) * | 2011-07-07 | 2012-04-11 | 中国石油化工集团公司 | 端氨基聚醚制备工艺 |
| CN102389802B (zh) * | 2011-09-20 | 2013-08-28 | 中国石油化工集团公司 | 一种端氨基聚醚合成催化剂及其制备方法 |
| CN102964586A (zh) * | 2012-12-06 | 2013-03-13 | 盘锦科隆精细化工股份有限公司 | 一种用于聚醚胺的催化剂的制备方法 |
| CN104099069B (zh) * | 2013-04-12 | 2017-02-08 | 中国石油化工股份有限公司 | 一种抗温型粘土防膨剂及其制备工艺 |
| CN108003041A (zh) * | 2016-10-28 | 2018-05-08 | 中国石油化工股份有限公司 | 一种分离聚醚醇和聚醚胺的方法 |
| FR3073843A1 (fr) | 2017-11-21 | 2019-05-24 | Arkema France | Additifs de rheologie a base de di- ou tri-amides et de leurs melanges |
| CN107964094B (zh) * | 2017-11-28 | 2020-04-07 | 中国科学院长春应用化学研究所 | 一种用于合成端伯氨基聚醚的催化剂、其制备方法及应用 |
| FR3094367B1 (fr) | 2019-03-29 | 2023-03-03 | Arkema France | Additifs de rhéologie à base de di- ou tri-amides hydroxyles et de leurs mélanges |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3847992A (en) * | 1973-03-12 | 1974-11-12 | Jefferson Chem Co Inc | Partially aminated polyoxyalkylene polyols |
-
1986
- 1986-03-15 DE DE19863608716 patent/DE3608716A1/de not_active Withdrawn
- 1986-04-10 GB GB8608710A patent/GB2175910B/en not_active Expired
- 1986-05-15 JP JP10971686A patent/JPS61278528A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7696385B2 (en) | 2005-06-28 | 2010-04-13 | Clariant Produkte (Deutschland) Gmbh | Polyetheramine production method |
| US8889814B2 (en) | 2006-08-03 | 2014-11-18 | Clariant Finance (Bvi) Limited | Polyetheramine macromonomers comprising two neighboring hydroxyl groups and their use for producing polyurethanes |
| US8071814B2 (en) | 2006-12-06 | 2011-12-06 | Clariant Finance (Bvi) Limited | Process for preparing polyetheramines |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2175910B (en) | 1989-06-28 |
| GB2175910A (en) | 1986-12-10 |
| GB8608710D0 (en) | 1986-05-14 |
| JPS61278528A (ja) | 1986-12-09 |
| JPH0140049B2 (enrdf_load_stackoverflow) | 1989-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |