CH622489A5 - Process for the preparation of 2-amino-1-alcohols - Google Patents

Process for the preparation of 2-amino-1-alcohols Download PDF

Info

Publication number: CH622489A5
Authority: CH; Switzerland
Prior art keywords: ammonia; hydroxy; formula; compound; amino
Prior art date: 1975-10-24

Application number

CH1331276A

Other languages

German (de)

English (en)

Inventor

Walter Dr Himmele

Leopold Dr Hupfer

Herbert Dr Toussaint

Gerhard Dr Paul

Original Assignee

Basf Ag

Priority date (The priority date 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 date listed.)

1975-10-24

Filing date

1976-10-21

Publication date

1981-04-15

1976-10-21 Application filed by Basf Ag filed Critical Basf Ag

1981-04-15 Publication of CH622489A5 publication Critical patent/CH622489A5/de

Links

238000000034 method Methods 0.000 title claims description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 50
229910021529 ammonia Inorganic materials 0.000 claims description 24
239000003054 catalyst Substances 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 16
239000011541 reaction mixture Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 5
239000010941 cobalt Substances 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
150000001298 alcohols Chemical class 0.000 claims 2
150000001412 amines Chemical class 0.000 claims 2
150000000180 1,2-diols Chemical class 0.000 claims 1
150000001299 aldehydes Chemical class 0.000 claims 1
238000010924 continuous production Methods 0.000 claims 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
150000002576 ketones Chemical class 0.000 claims 1
238000006268 reductive amination reaction Methods 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims 1
239000007789 gas Substances 0.000 description 11
238000005576 amination reaction Methods 0.000 description 10
238000009835 boiling Methods 0.000 description 6
ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-UHFFFAOYSA-N 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
DDPRYTUJYNYJKV-UHFFFAOYSA-N 1,4-diethylpiperazine Chemical compound CCN1CCN(CC)CC1 DDPRYTUJYNYJKV-UHFFFAOYSA-N 0.000 description 5
BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
150000001414 amino alcohols Chemical class 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 3
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
238000001125 extrusion Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
150000002918 oxazolines Chemical class 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910000428 cobalt oxide Inorganic materials 0.000 description 2
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 2
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
241001473877 Biserrula isolate Species 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
239000012971 dimethylpiperazine Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
229960000285 ethambutol Drugs 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Chemical class 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
239000002912 waste gas Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives

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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CH1331276A 1975-10-24 1976-10-21 Process for the preparation of 2-amino-1-alcohols CH622489A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2547654A DE2547654C2 (de)	1975-10-24	1975-10-24	Herstellung von 2-Amino-1-alkoholen und 3-Oxalin-Derivate

Publications (1)

Publication Number	Publication Date
CH622489A5 true CH622489A5 (en)	1981-04-15

Family

ID=5960008

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1331276A CH622489A5 (en)	1975-10-24	1976-10-21	Process for the preparation of 2-amino-1-alcohols

Country Status (8)

Country	Link
JP (1)	JPS6013020B2 (2)
BE (1)	BE847568A (2)
CH (1)	CH622489A5 (2)
DE (1)	DE2547654C2 (2)
FR (1)	FR2328701A1 (2)
GB (1)	GB1554176A (2)
IL (1)	IL50634A (2)
IT (1)	IT1068266B (2)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3516028A1 (de) *	1985-05-04	1986-11-06	Hüls AG, 4370 Marl	Di-(tert.-butanol)-amin und verfahren zu seiner herstellung durch hydrierung von 2(1-hydroxy-1-methyl-ethyl)-5,5-dimethyl-1,3-oxazolin
DE3609978A1 (de) *	1986-03-25	1987-10-01	Merck Patent Gmbh	Verfahren zur herstellung von hydroxyaminen
US7619118B2 (en)	2006-06-07	2009-11-17	The Procter & Gamble Company	Process for the conversion of glycerol to propylene glycol and amino alcohols
MX2008015685A (es) *	2006-06-07	2009-01-12	Procter & Gamble	Procesos para convertir glicerol en aminoalcoholes.
US7619119B2 (en)	2006-06-07	2009-11-17	The Procter & Gamble Company	Processes for converting glycerol to amino alcohols
WO2016038632A1 (en) *	2014-09-12	2016-03-17	Council Of Scientific And Industrial Research	A one pot process for synthesis of oxazoline and imidazole compounds from glycerol

1975
- 1975-10-24 DE DE2547654A patent/DE2547654C2/de not_active Expired
1976
- 1976-09-08 IT IT27005/76A patent/IT1068266B/it active
- 1976-10-07 IL IL50634A patent/IL50634A/xx unknown
- 1976-10-20 FR FR7631584A patent/FR2328701A1/fr active Granted
- 1976-10-21 CH CH1331276A patent/CH622489A5/de not_active IP Right Cessation
- 1976-10-22 BE BE171735A patent/BE847568A/xx not_active IP Right Cessation
- 1976-10-22 GB GB43919/76A patent/GB1554176A/en not_active Expired
- 1976-10-25 JP JP51127410A patent/JPS6013020B2/ja not_active Expired

Also Published As

Publication number	Publication date
IT1068266B (it)	1985-03-21
JPS5253807A (en)	1977-04-30
GB1554176A (en)	1979-10-17
FR2328701B1 (2)	1980-03-14
DE2547654A1 (de)	1977-04-28
IL50634A0 (en)	1976-12-31
DE2547654C2 (de)	1982-09-09
JPS6013020B2 (ja)	1985-04-04
FR2328701A1 (fr)	1977-05-20
BE847568A (fr)	1977-04-22
IL50634A (en)	1979-09-30

Legal Events

Date	Code	Title	Description
1995-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0070397B1 (de)	1985-04-10	Verfahren und Katalysator zur Herstellung von cyclischen Iminen
EP0033529A1 (de)	1981-08-12	Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin
EP1270543B1 (de)	2009-10-07	Verfahren zur Herstellung von sekundären Aminen aus primären Aminen
EP2855443B1 (de)	2016-03-30	Verfahren zur herstellung eines mono-n-alkyl-piperazins
DE10357718A1 (de)	2005-07-21	Verfahren zur Herstellung von Tricyclodecandialdehyd
EP0235651B1 (de)	1990-10-24	Verfahren zur Herstellung von N-Methylpiperazin
DE1941536A1 (de)	1970-03-05	1-Alkyl-2-aminomethylpyrrolidine sowie Verfahren zur Herstellung dieser Verbindungen und deren Zwischenprodukte
CH622489A5 (en)	1981-04-15	Process for the preparation of 2-amino-1-alcohols
DE69228114T2 (de)	1999-06-02	Verfahren zur Herstellung von Gamma-Butyrolacton
EP0328920B1 (de)	1991-12-04	Verfahren zur Herstellung von 1,2,4-Butantriol
US4105669A (en)	1978-08-08	Manufacture of 2-amino-1-alcohols
EP0435072B1 (de)	1994-04-27	Verfahren zur Herstellung von N,N-Dimethylaminen
EP0300323B1 (de)	1992-03-04	Verfahren zur Herstellung von aliphatischen N,N-dialkylsubstituierten Aminoalkoholen
EP0767769A1 (de)	1997-04-16	Verfahren zur herstellung von 1,4-butandiol
EP0111861A2 (de)	1984-06-27	Verfahren zur Herstellung von Aminen
EP0931046B1 (de)	2001-06-27	VERFAHREN ZUR HERSTELLUNG VON n-BUTYLALKYLETHERN
EP0105146A1 (de)	1984-04-11	Verfahren zur Herstellung von Diaminen oder Diamingemischen
DE4141222A1 (de)	1993-06-17	Verfahren zur herstellung von 4-hydroxymethyl- tetrahydropyranan
DE2430038C3 (de)	1980-02-14	Verfahren zur Herstellung von Acetoxybutanol
DE69318738T2 (de)	1998-09-24	Katalytische Synthese von Alkylmorpholinonen
DE69316825T2 (de)	1998-09-10	Prozess zur Herstellung von Diphenylamin oder kern-substitierten Derivaten
EP0436860A1 (de)	1991-07-17	Verfahren zur Herstellung von 2-(4-Chlorphenyl)-3-methyl-buttersäure
DE2703077A1 (de)	1978-07-27	Verfahren zur herstellung von cyclohexandion-(1,4)-tetramethyl- diketal
EP0007041B1 (de)	1981-11-25	Verfahren zur Herstellung von Anthron
DE2504981B2 (de)	1977-10-27	Verfahren zur herstellung von propylenoxid und/oder allylalkohol und/oder propionaldehyd und/oder aceton