KR960007532A - 아민류의 제조방법 - Google Patents
아민류의 제조방법 Download PDFInfo
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- KR960007532A KR960007532A KR1019950024756A KR19950024756A KR960007532A KR 960007532 A KR960007532 A KR 960007532A KR 1019950024756 A KR1019950024756 A KR 1019950024756A KR 19950024756 A KR19950024756 A KR 19950024756A KR 960007532 A KR960007532 A KR 960007532A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
- B01J23/885—Molybdenum and copper
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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Abstract
본 발명은 80 내지 250℃의 온도에서 수소를 이용한 1 내지 400bar의 압력하에, 촉매적 활성 물질에 ZrO2로 계산하여 20 내지 85 중량%의 산소-함유 지르코늄 화합물, CuO로 계산하여 1 내지 30 중량%의 산소-함유 구리 화합물, NiO로 계산하여 30 내지 70 중량%%의 산호- 함유 니켈 화합물, MoO3로 계산하여 0.1 내지 5중량%의 산소-함유 몰리브덴 화합물, 그리고 Al2O3또는 MnO2를 기준으로 각각 알루미늄 및/또는 망간의 산소-함유 화합물이 0 내지 10 중량% 함유되어 있는 지르코늄/구리/니켈 촉매의 존재 상태에서, 암모니아와 1차 및 2차 아민류로 이루어진 군으로부터 선택된 1차 또는 2차 알코올류 및 질소 화합물로부터 아민류를 제조하는 신규하고도 개선된 방법에 관한 것이다.
본 발명에 따르면, 다음의 일반식(ⅱ)의 1차 또는 2차 알코올과
R4-CHR3-OH (ⅱ)
다음의 일반식(ⅲ)의 질소 화합물로부터
(ⅲ)
다음의 일반식 (ⅰ)의 아민류를 제조하는 바람직한 방법이 제공되는데,
(ⅰ)
상기 식들에서, R1및 R2는 수소, C1-C20알킬, C3-C12시클로알킬, 아릴, C7-C20아르알킬 및 C7-C20알킬아릴이거나, 함께 (CH2)l-X-(CH2)m을 형성하고, R3및 R4는 수소, C1-C20알킬, C3-C12시클로알킬, C1-C20히드록시알킬, 아미노 및/또는 히드록시로 치환된 C1-C20알킬, C2-C30알콕시알킬, R5-(OCR6R7CR8R9)n-(OCR6R7), 아릴, C7-C2아르알킬, C7-C20알킬아릴, (R5)2N-(CH2)q및 Y-(CH2)m-NR5-(CH2)q이거나, 함께 (CH2)l-X(CH2)m을 형성하거나, R2및 R4는 함께 (CH2)l-X-(CH2)m을 형성하고, R5는 수소, C1-C4알킬, C12-C40알킬페닐을 나타내고, R6, R7, R8, 및 R9는 수소, 메틸 또는 에틸을 나타내고, R10은 수소 또는 C1-C4알킬을 나타내고, X는 CH2, 산소 또는 N-R6를 나타내고, Y는 (R5)2, 히드록시, C2-C20알킬아미노알킬 또는 C3-C20디알킬아미노알킬을 나타내고, n은 1 내지 30의 정수이고, 1은 2내지 4의 정수이고, m과 q는 1 내지 4의 정수이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 아민의 제조 방법으로서, 80 내지 250℃의 온도에서 수소를 이용한 1 내지 400bar의 압력하에, 촉매적 활성 물질에 ZrO2로 계산하여 20 내지 85 중량%의 산소-함유 지르코늄 화합물, CuO로 계산하여 1 내지 30 중량%의 산소-함유 구리 화합물, NiO로 계산하여 30 내지 70 중량%%의 산호- 함유 니켈 화합물, MoO3로 계산하여 0.1 내지 5중량%의 산소-함유 몰리브덴 화합물, 그리고 Al2O3또는 MnO2를 기준으로 각각 알루미늄 및/또는 망간의 산소-함유 화합물이 0 내지 10 중량% 함유되어 있는 지르코늄/구리/니켈 촉매의 존재 상태에서, 암모니아와 1차 및 2차 아민류로 이루어진 군으로부터 선택된 1차 또는 2차 알코올류 및 질소 화합물로부터 아민류를 제조하는 방법.
- 아민의 제조방법으로서, 다음의 일반식(ⅱ)의 1차 또는 2차 알코올과R4-CHR3-OH (ⅱ)다음의 일반식(ⅲ)의 질소 화합물로부터(ⅲ)80 내지 250℃의 온도에서 수소를 이용한 1 내지 400bar의 압력하에, 촉매적 활성 물질에 ZrO2로 계산하여 20 내지 85 중량%의 산소-함유 지르코늄 화합물, CuO로 계산하여 1 내지 30 중량%의 산소-함유 구리 화합물, NiO로 계산하여 30 내지 70 중량%%의 산호- 함유 니켈 화합물, MoO3로 계산하여 0.1 내지 5중량%의 산소-함유 몰리브덴 화합물, 그리고 Al2O3또는 MnO2를 기준으로 각각 알루미늄 및/또는 망간의 산소-함유 화합물이 0 내지 10 중량% 함유되어 있는 지르코늄/구리/니켈 촉매의 존재 상태에서, 다음의 일반식(i)의 아민류를 제조하는 방법.(i)상기 식들에서, R1및 R2는 수소, C1-C20알킬, C3-C12시클로알킬, 아릴, C7-C20아르알킬 및 C7-C20알킬아릴이거나, 함께 (CH2)l-X-(CH2)m을 형성하고, R3및 R4는 수소, C1-C20알킬, C3-C12시클로알킬, C1-C20히드록시알킬, 아미노 및/또는 히드록시로 치환된 C1-C20알킬, C2-C30알콕시알킬, R5-(OCR6R7CR8R9)n-(OCR6R7), 아릴, C7-C2아르알킬, C7-C20알킬아릴, (R5)2N-(CH2)q및 Y-(CH2)m-NR5-(CH2)q이거나, 함께 (CH2)l-X(CH2)m을 형성하거나, R2및 R4는 함께 (CH2)l-X-(CH2)m을 형성하고, R5는 수소, C1-C4알킬, C12-C40알킬페닐을 나타내고, R6, R7, R8, 및 R9는 수소, 메틸 또는 에틸을 나타내고, R10은 수소 또는 C1-C4알킬을 나타내고, X는 CH2, 산소 또는 N-R6를 나타내고, Y는 (R5)2, 히드록시, C2-C20알킬아미노알킬 또는 C3-C20디알킬아미노알킬을 나타내고, n은 1 내지 30의 정수이고, 1은 2내지 4의 정수이고, m과 q는 1 내지 4의 정수이다.
- 제1항에서 정의된 지르코늄/구리/니켈 촉매의 존재하에 수소를 사용하여 알코올 및 질소 화합물로 부터 아민을 제조하는 방법에 있어서, 촉매적 활성물질에 NiO를 기준으로 계산하여 40 내지 70 중량%의 산소-함유 니켈 화합물이 함유되어 있는 것을 특징으로 하는 아민의 제조방법.
- 제1항에서 정의된 지르코늄/구리/니켈 촉매의 존재하에 수소를 사용하여 알코올 및 질소 화합물로 부터 아민을 제조하는 방법에 있어서, 촉매적 활성물질에 NiO를 기준으로 계산하여 45 내지 60 중량%의 산소-함유 니켈 화합물이 함유되어 있는 것을 특징으로 하는 아민의 제조방법.
- 제1항에서 정의된 지르코늄/구리/니켈 촉매의 존재하에 수소를 사용하여 알코올 및 질소 화합물로 부터 아민을 제조하는 방법에 있어서, 촉매적 활성물질에 MoO3를 기준으로 계산하여 0.5 내지 3.5 중량%의 산소-함유 니켈 화합물이 함유되어 있는 것을 특징으로 하는 아민의 제조방법.
- 제1항에서 정의된 지르코늄/구리/니켈 촉매의 존재하에 수소를 사용하여 알코올 및 질소 화합물로 부터 아민을 제조하는 방법에 있어서, 촉매적 활성물질에 ZrO2를 기준으로 계산하여 25 내지 60 중량%의 산소-함유 니켈 화합물이 함유되어 있는 것을 특징으로 하는 아민의 제조방법.
- 제 1항에서 정의된 지르코늄/구리/니켈 촉매의 존재하에 수소를 사용하여 알코올 및 질소 화합물로 부터 아민을 제조하는 방법에 있어서, 촉매적 활성물질에 CuO를 기준으로 계산하여 10 내지 25 중량%의 산소-함유 니켈 화합물이 함유되어 있는 것을 특징으로 하는 아민의 제조방법.
- 제1항에서 정의된 지르코늄/구리/니켈 촉매의 존재하에 수소를 사용하여 알코올 및 질소 화합물로 부터 아민을 제조하는 방법에 있어서, 반응을 120° 내지 230°의 온도에서 수행하는 것을 특징으로 하는 아민의 제조방법.
- 제1항에서 정의된 지르코늄/구리/니켈 촉매의 존재하에 수소를 사용하여 알코올 및 질소 화합물로 부터 아민을 제조하는 방법에 있어서, 반응을 10 내지 250bar의 압력에서 수행하는 것을 특징으로 하는 아민의 제조방법.
- 제1항에서 정의된 지르코늄/구리/니켈 촉매의 존재하에 수소를 사용하여 알코올 및 질소 화합물로 부터 아민을 제조하는 방법에 있어서, 반응을 30 내지 220bar의 압력하에 수행하는 것을 특징으로 하는 아민의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4428004A DE4428004A1 (de) | 1994-08-08 | 1994-08-08 | Verfahren zur Herstellung von Aminen |
DEP4428004.1 | 1994-08-08 |
Publications (2)
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KR960007532A true KR960007532A (ko) | 1996-03-22 |
KR100376641B1 KR100376641B1 (ko) | 2003-05-22 |
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KR1019950024756A KR100376641B1 (ko) | 1994-08-08 | 1995-08-08 | 아민의제조방법 |
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US (1) | US5530127A (ko) |
EP (1) | EP0696572B1 (ko) |
JP (1) | JP3809963B2 (ko) |
KR (1) | KR100376641B1 (ko) |
CN (1) | CN1078200C (ko) |
AT (1) | ATE158788T1 (ko) |
CA (1) | CA2155171C (ko) |
DE (2) | DE4428004A1 (ko) |
DK (1) | DK0696572T3 (ko) |
ES (1) | ES2107885T3 (ko) |
ZA (1) | ZA956574B (ko) |
Families Citing this family (174)
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DE4429547A1 (de) * | 1994-08-19 | 1996-02-22 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE19516940A1 (de) * | 1995-05-09 | 1996-11-14 | Rwe Dea Ag | Herstellung von primären Guerbetaminen |
JP3361414B2 (ja) * | 1995-09-22 | 2003-01-07 | 花王株式会社 | N,n−ジメチル−n−アルキルもしくはアルケニルアミンの製造方法 |
US5679862A (en) * | 1996-03-25 | 1997-10-21 | Chemical Research & Licensing Company | Amination process |
DE19645430A1 (de) * | 1996-11-04 | 1998-05-07 | Basf Ag | Polyolefine und deren funktionalisierte Derivate |
DE19742911A1 (de) * | 1997-09-29 | 1999-04-01 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE19905837A1 (de) * | 1999-02-12 | 2000-08-17 | Basf Ag | Verfahren zur Racemisierung von optisch aktiven Aminen |
DE19910960A1 (de) * | 1999-03-12 | 2000-09-14 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE19916512A1 (de) * | 1999-04-13 | 2000-10-19 | Basf Ag | Polyalkenalkohol-Polyetheramine und deren Verwendung in Kraft- und Schmierstoffen |
EP1106601B1 (de) * | 1999-12-06 | 2004-02-25 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Monoisopropylamin |
DE50007278D1 (de) | 1999-12-06 | 2004-09-09 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE10145119A1 (de) | 2001-09-13 | 2003-04-03 | Basf Ag | Verfahren zur Herstellung von Aminen |
US7196033B2 (en) | 2001-12-14 | 2007-03-27 | Huntsman Petrochemical Corporation | Advances in amination catalysis |
DE10211101A1 (de) * | 2002-03-14 | 2003-09-25 | Basf Ag | Katalysatoren und Verfahren zur Herstellung von Aminen |
DE10261193A1 (de) | 2002-12-20 | 2004-07-01 | Basf Ag | Verfahren zur Herstellung eines Armins |
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WO2022179864A1 (en) | 2021-02-25 | 2022-09-01 | Basf Se | Process for the production of polyalkylene-polyamines by condensation of alkylene-diamines |
KR20240072249A (ko) | 2021-10-07 | 2024-05-23 | 바스프 에스이 | 액체 상에서의 비스(피롤리디노)부탄의 제조 방법 |
WO2023135035A1 (en) | 2022-01-14 | 2023-07-20 | Basf Se | Method for the manufacture or conversion of alkanolamines |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE757840A (fr) | 1969-10-23 | 1971-04-22 | Basf Ag | Procede de preparation d'amines a partir d'alcools |
US4014933A (en) * | 1969-10-23 | 1977-03-29 | Basf Aktiengesellschaft | Production of amines from alcohols |
US4151204A (en) | 1975-06-27 | 1979-04-24 | Teijin Limited | Process for preparing amino alcohols |
SE457608B (sv) | 1986-07-11 | 1989-01-16 | Berol Kemi Ab | Foerfarande foer framstaellning av en ruteniumdopad nickel- och/eller koboltkatalysator paa en poroes metalloxidbaerare samt anvaendning av katalysatorn i en hydrerings- och/eller dehydreringsreaktion |
DE3903367A1 (de) | 1989-02-04 | 1990-08-16 | Basf Ag | Katalysator und verfahren zur hydrierenden aminierung von alkoholen |
US5166433A (en) * | 1989-02-04 | 1992-11-24 | Basf Aktiengesellschaft | Catalyst and the amination of alcohols under hydrogenating conditions |
DE4116367A1 (de) * | 1991-05-18 | 1992-11-19 | Basf Ag | Verfahren zur herstellung von aminen |
-
1994
- 1994-08-08 DE DE4428004A patent/DE4428004A1/de not_active Withdrawn
-
1995
- 1995-07-29 AT AT95111954T patent/ATE158788T1/de not_active IP Right Cessation
- 1995-07-29 ES ES95111954T patent/ES2107885T3/es not_active Expired - Lifetime
- 1995-07-29 EP EP95111954A patent/EP0696572B1/de not_active Expired - Lifetime
- 1995-07-29 DK DK95111954.4T patent/DK0696572T3/da active
- 1995-07-29 DE DE59500748T patent/DE59500748D1/de not_active Expired - Lifetime
- 1995-08-01 CA CA002155171A patent/CA2155171C/en not_active Expired - Fee Related
- 1995-08-01 US US08/509,997 patent/US5530127A/en not_active Expired - Lifetime
- 1995-08-07 ZA ZA9506574A patent/ZA956574B/xx unknown
- 1995-08-08 JP JP20205395A patent/JP3809963B2/ja not_active Expired - Lifetime
- 1995-08-08 CN CN95116324A patent/CN1078200C/zh not_active Expired - Lifetime
- 1995-08-08 KR KR1019950024756A patent/KR100376641B1/ko not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE59500748D1 (de) | 1997-11-06 |
EP0696572B1 (de) | 1997-10-01 |
ES2107885T3 (es) | 1997-12-01 |
KR100376641B1 (ko) | 2003-05-22 |
US5530127A (en) | 1996-06-25 |
JPH08176074A (ja) | 1996-07-09 |
DE4428004A1 (de) | 1996-02-15 |
ATE158788T1 (de) | 1997-10-15 |
CA2155171C (en) | 2006-03-14 |
ZA956574B (en) | 1997-02-07 |
CN1123789A (zh) | 1996-06-05 |
EP0696572A1 (de) | 1996-02-14 |
DK0696572T3 (da) | 1997-10-27 |
CN1078200C (zh) | 2002-01-23 |
CA2155171A1 (en) | 1996-02-09 |
JP3809963B2 (ja) | 2006-08-16 |
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