JP2009191067A - 4−アミノ−2,2,6,6−テトラメチルピペリジンの製造方法 - Google Patents
4−アミノ−2,2,6,6−テトラメチルピペリジンの製造方法 Download PDFInfo
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- JP2009191067A JP2009191067A JP2009015170A JP2009015170A JP2009191067A JP 2009191067 A JP2009191067 A JP 2009191067A JP 2009015170 A JP2009015170 A JP 2009015170A JP 2009015170 A JP2009015170 A JP 2009015170A JP 2009191067 A JP2009191067 A JP 2009191067A
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- tetramethylpiperidine
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- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 17
- 239000010941 cobalt Substances 0.000 claims abstract description 17
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 13
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 64
- 230000008569 process Effects 0.000 claims description 53
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 6
- 238000006268 reductive amination reaction Methods 0.000 claims description 6
- 238000010533 azeotropic distillation Methods 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000000701 coagulant Substances 0.000 claims 1
- 241001550224 Apha Species 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 6
- 238000004040 coloring Methods 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- -1 2,2,6,6-tetrasubstituted 4-aminopiperidine Chemical class 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005054 agglomeration Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- ZEPOIZSLOVHVIP-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidin-4-one Chemical compound CC1C(=O)CCN(C)C1(C)C ZEPOIZSLOVHVIP-UHFFFAOYSA-N 0.000 description 1
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
【解決手段】ニッケル触媒またはコバルト触媒および水の存在下で2,2,6,6−テトラメチルピペリジン−4−オンとアンモニアおよび水素を反応させることによる4−アミノ−2,2,6,6−テトラメチルピペリジンの製造方法において、主反応を最大50barの圧力および最大120℃の温度で、少なくとも80%の2,2,6,6−テトラメチルピペリジン−4−オンの変換率まで実施し、引き続き、後反応を主反応の圧力および温度と比較してより高い温度で、かつより高い圧力で行うことを特徴とする製造法によって解決される。
【選択図】なし
Description
従って本発明の対象は、主反応が最大50barの圧力および最大120℃の温度で、少なくとも80%の2,2,6,6−テトラメチルピペリジン−4−オンの変換率まで実施され、引き続き、後反応が主反応の圧力および温度と比較してより高い温度で、かつより高い圧力で行われることを特徴とする、ニッケル触媒またはコバルト触媒および水の存在下で2,2,6,6−テトラメチルピペリジン−4−オンとアンモニアおよび水素を反応させることによる4−アミノ−2,2,6,6−テトラメチルピペリジンの製造法である。
プロペラ攪拌機、電熱装置、空気冷却器および水素−質量流量調節装置を有する1lの攪拌式オートクレーブ中に、2,2,6,6−テトラメチルピペリジン−4−オン300g、脱イオン水および触媒11gをアルゴン下で装入する。触媒として、一方ではEvonik Degussa GmbHのB113W(活性金属 ニッケル)を、かつ他方ではB2112Z(活性金属 コバルト)を使用した。引き続き、オートクレーブを三回、窒素で洗浄した。攪拌機を、300rpmの回転数に調整する。それから液体アンモニア83gを計量供給する。引き続き、水素によって圧力を主反応の所望された圧力に調整し、さらに温度を調整する。後反応を、150℃の温度および50barの圧力で約3時間行う。それとは相違する後反応のための条件は、以下の第1表の中に記載されている。第1表は、試験パラメータのみならず実施された例の結果も示す。
ブレード式攪拌機および加熱された二重ケーシングを有する2lの攪拌式オートクレーブ中に、2,2,6,6−テトラメチルピペリジン−4−オン450g、脱イオン水250gおよびコバルト触媒(型:Evonik Degussa GmbH B2112Z、水湿)33gをアルゴン下で装入する。引き続き、オートクレーブを密閉し、かつ三回、窒素で洗浄する。攪拌機を、500rpmの回転数に調整する。それから液体アンモニア125gを計量供給し、かつ内部温度90℃に加熱する。引き続き、水素によって40barの圧力に調整する。後反応を、150℃およびH250barで約1時間行う。その後に冷却し、かつオートクレーブを内部温度約50℃で放圧し、二回、窒素で洗浄し、かつ反応生成物をアルゴン下で放出する。
Claims (15)
- 4−アミノ−2,2,6,6−テトラメチルピペリジンを、ニッケル触媒またはコバルト触媒および水の存在下で2,2,6,6−テトラメチルピペリジン−4−オンとアンモニアおよび水素との反応によって製造する方法において、主反応を最大50barの圧力および最大120℃の温度で、少なくとも80%の2,2,6,6−テトラメチルピペリジン−4−オンの変換率まで実施し、引き続き、後反応を主反応の圧力および温度と比較してより高い温度で、かつより高い圧力で行うことを特徴とする、4−アミノ−2,2,6,6−テトラメチルピペリジンの製造方法。
- 水および2,2,6,6−テトラメチルピペリジン−4−オンを、2.5:1〜9:1のモル比で使用することを特徴とする、請求項1記載の方法。
- 水および2,2,6,6−テトラメチルピペリジン−4−オンを、3:1〜7:1のモル比で使用することを特徴とする、請求項2記載の方法。
- 活性金属のコバルトおよび/またはニッケルを有する骨格金属触媒を使用することを特徴とする、請求項1から3までのいずれか1項記載の方法。
- 使用される2,2,6,6−テトラメチルピペリジン−4−オンに対して骨格金属触媒0.5〜15質量%を使用することを特徴とする、請求項4記載の方法。
- 主反応を40℃〜110℃の温度で実施することを特徴とする、請求項1から5までのいずれか1項記載の方法。
- 主反応を5〜50barの圧力で実施することを特徴とする、請求項1から6までのいずれか1項記載の方法。
- 後反応を130〜200℃の温度で実施することを特徴とする、請求項1から7までのいずれか1項記載の方法。
- 後反応を35〜150barの圧力で実施することを特徴とする、請求項1から8までのいずれか1項記載の方法。
- 後反応を主反応と同じ反応器中で実施することを特徴とする、請求項1から9までのいずれか1項記載の方法。
- 反応混合物の後処理を、主反応の後および後反応の前に行わないことを特徴とする、請求項1から10までのいずれか1項記載の方法。
- アンモニアおよび2,2,6,6−テトラメチルピペリジン−4−オンを、1.5:1〜4:1のモル比で使用することを特徴とする、請求項1から11までのいずれか1項記載の方法。
- 触媒を液相から傾瀉することによって分離除去し、その際、あらかじめ反応混合物に凝集助剤を添加することを特徴とする、請求項1から12までのいずれか1項記載の方法。
- 触媒を懸濁液として、さらなる還元アミノ化に供給することを特徴とする、請求項13記載の方法。
- 液相に共沸添加剤を添加し、引き続き共沸蒸留を実施することを特徴とする、請求項13または14記載の方法。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008000214.3 | 2008-02-01 | ||
DE102008000214 | 2008-02-01 | ||
DE102008040045A DE102008040045A1 (de) | 2008-02-01 | 2008-07-01 | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
DE102008040045.9 | 2008-07-01 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009191067A true JP2009191067A (ja) | 2009-08-27 |
JP5522951B2 JP5522951B2 (ja) | 2014-06-18 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2009015170A Active JP5522951B2 (ja) | 2008-02-01 | 2009-01-27 | 4−アミノ−2,2,6,6−テトラメチルピペリジンの製造方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US8252934B2 (ja) |
JP (1) | JP5522951B2 (ja) |
KR (1) | KR101658666B1 (ja) |
CN (1) | CN101497583B (ja) |
AT (1) | ATE478846T1 (ja) |
DE (2) | DE102008040045A1 (ja) |
MX (1) | MX2009000854A (ja) |
SG (1) | SG154402A1 (ja) |
SI (1) | SI2085385T1 (ja) |
TW (1) | TWI449694B (ja) |
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EP2319832A1 (en) * | 2009-10-20 | 2011-05-11 | Basf Se | Sterically hindered amines |
CN109836370A (zh) * | 2019-03-20 | 2019-06-04 | 萧县新秀新材料有限公司 | 特定pH范围的2,2,6,6-四甲基哌啶胺的合成法 |
CN110526860B (zh) * | 2019-07-27 | 2022-10-28 | 宁夏沃凯珑新材料有限公司 | 一种制备中间体2,2,6,6–四甲基哌啶胺的方法 |
CN111689893B (zh) * | 2020-07-08 | 2021-08-31 | 江苏富比亚化学品有限公司 | 一种2,2,6,6-四甲基-4-氨基哌啶的制备方法 |
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GB2176473A (en) * | 1985-06-13 | 1986-12-31 | Khim Dlya Polimernykh Material | Method for preparing 4-amino-2,2,6,6-tetramethylpiperidine |
WO1997046529A1 (de) * | 1996-06-03 | 1997-12-11 | Basf Aktiengesellschaft | Verfahren zur reinigung von sterisch gehinderten 4-amino-piperidinen |
JPH10291976A (ja) * | 1997-03-06 | 1998-11-04 | Basf Ag | 4−アミノ−2,2,6,6−テトラメチルピペリジン及び2,2,6,6−テトラメチル−4−ピペリジンイミンの製造方法 |
WO1999016749A1 (de) * | 1997-10-01 | 1999-04-08 | Basf Aktiengesellschaft | Verfahren zur reinigung von 4-amino-piperidinen |
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GB216473A (en) * | 1923-02-21 | 1924-05-21 | Elyria Iron And Steel Company | Improvements in tube-supporting and compressing devices for apparatus for welding tubing and the like |
DE3003843A1 (de) | 1980-02-02 | 1981-08-13 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von 4-amino-2,2,6,6-tetramethylpiperidin |
DE3021955A1 (de) | 1980-06-12 | 1981-12-24 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung primaerer mono- und diamine aus oxoverbindungen |
SU1088304A1 (ru) * | 1982-01-29 | 1987-11-07 | Научно-исследовательский институт химикатов для полимерных материалов | Способ получени 2,2,6,6-тетраметил-4-аминопиперидина |
DE4442990A1 (de) | 1994-12-02 | 1996-06-05 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
DE19544599A1 (de) | 1995-11-30 | 1997-06-05 | Huels Chemische Werke Ag | Kontinuierliches Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
DE19704460A1 (de) * | 1997-02-06 | 1998-08-13 | Huels Chemische Werke Ag | Kontinuierliches Verfahren zur Herstellung von 4-Aminopiperidinen |
CN1141296C (zh) | 2000-12-13 | 2004-03-10 | 北京化工大学 | 4-哌啶胺的合成及其催化剂与其制备方法 |
GB0212808D0 (en) * | 2002-05-10 | 2002-07-10 | Bisset David I | Improved means to disconnect and/or isolate an electrical appliance |
EP1787989A1 (de) * | 2005-11-17 | 2007-05-23 | Degussa GmbH | Triazinverbindungen mit Aminogruppen- und Carboxygruppen-haltigen Substituenten |
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2008
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- 2009-01-23 TW TW098103081A patent/TWI449694B/zh active
- 2009-01-24 CN CN200910009950XA patent/CN101497583B/zh active Active
- 2009-01-27 JP JP2009015170A patent/JP5522951B2/ja active Active
- 2009-01-27 DE DE502009000072T patent/DE502009000072D1/de active Active
- 2009-01-27 SI SI200930013T patent/SI2085385T1/sl unknown
- 2009-01-27 AT AT09151410T patent/ATE478846T1/de active
- 2009-01-29 US US12/362,136 patent/US8252934B2/en active Active
- 2009-01-30 KR KR1020090007510A patent/KR101658666B1/ko active IP Right Grant
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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GB2176473A (en) * | 1985-06-13 | 1986-12-31 | Khim Dlya Polimernykh Material | Method for preparing 4-amino-2,2,6,6-tetramethylpiperidine |
WO1997046529A1 (de) * | 1996-06-03 | 1997-12-11 | Basf Aktiengesellschaft | Verfahren zur reinigung von sterisch gehinderten 4-amino-piperidinen |
JPH10291976A (ja) * | 1997-03-06 | 1998-11-04 | Basf Ag | 4−アミノ−2,2,6,6−テトラメチルピペリジン及び2,2,6,6−テトラメチル−4−ピペリジンイミンの製造方法 |
WO1999016749A1 (de) * | 1997-10-01 | 1999-04-08 | Basf Aktiengesellschaft | Verfahren zur reinigung von 4-amino-piperidinen |
Also Published As
Publication number | Publication date |
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JP5522951B2 (ja) | 2014-06-18 |
CN101497583A (zh) | 2009-08-05 |
TW200948781A (en) | 2009-12-01 |
SI2085385T1 (sl) | 2010-12-31 |
US8252934B2 (en) | 2012-08-28 |
DE502009000072D1 (de) | 2010-10-07 |
SG154402A1 (en) | 2009-08-28 |
US20090209766A1 (en) | 2009-08-20 |
DE102008040045A1 (de) | 2009-08-06 |
MX2009000854A (es) | 2009-08-24 |
TWI449694B (zh) | 2014-08-21 |
ATE478846T1 (de) | 2010-09-15 |
KR101658666B1 (ko) | 2016-09-21 |
KR20090084751A (ko) | 2009-08-05 |
CN101497583B (zh) | 2012-11-14 |
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