CA1070305A - Methode pour la production de derives de la morpholine - Google Patents

Methode pour la production de derives de la morpholine

Info

Publication number: CA1070305A
Authority: CA; Canada
Prior art keywords: morpholine; aryl; alkyl; substituted; compound
Prior art date: 1975-06-02
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.): Expired

Application number

CA252,910A

Other languages

English (en)

Inventor

Michael E. Brennan

Ernest L. Yeakey

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Texaco Development Corp

Original Assignee

Texaco Development Corp

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.)

1975-06-02

Filing date

1976-05-20

Publication date

1980-01-22

1976-05-20 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1980-01-22 Application granted granted Critical

1980-01-22 Publication of CA1070305A publication Critical patent/CA1070305A/fr

Status Expired legal-status Critical Current

Links

YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract description 60
-1 morpholine compound Chemical class 0.000 title claims abstract description 49
238000000034 method Methods 0.000 title claims abstract description 39
150000001875 compounds Chemical class 0.000 claims abstract description 18
239000000126 substance Substances 0.000 claims abstract description 17
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 13
239000011574 phosphorus Substances 0.000 claims abstract description 13
239000007791 liquid phase Substances 0.000 claims abstract description 8
150000005840 aryl radicals Chemical class 0.000 claims abstract description 6
150000002431 hydrogen Chemical group 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims abstract description 6
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims description 13
235000011007 phosphoric acid Nutrition 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 8
150000003016 phosphoric acids Chemical class 0.000 claims description 8
GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims description 6
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical group C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
229910001463 metal phosphate Inorganic materials 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
229960004838 phosphoric acid Drugs 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 19
239000003054 catalyst Substances 0.000 description 13
239000000376 reactant Substances 0.000 description 12
150000002780 morpholines Chemical class 0.000 description 11
235000014786 phosphorus Nutrition 0.000 description 10
JPIGSMKDJQPHJC-UHFFFAOYSA-N 1-(2-aminoethoxy)ethanol Chemical compound CC(O)OCCN JPIGSMKDJQPHJC-UHFFFAOYSA-N 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 7
239000002253 acid Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
238000006297 dehydration reaction Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000012808 vapor phase Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
239000005955 Ferric phosphate Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 2
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 2
229910000149 boron phosphate Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
229940032958 ferric phosphate Drugs 0.000 description 2
239000012535 impurity Substances 0.000 description 2
WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 2
229910000399 iron(III) phosphate Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
150000003014 phosphoric acid esters Chemical group 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
SEQVGSMAFZXDPQ-UHFFFAOYSA-N 1-[2-(ethylamino)ethoxy]ethanol Chemical compound CCNCCOC(C)O SEQVGSMAFZXDPQ-UHFFFAOYSA-N 0.000 description 1
LFWVZGUDOFDLHF-UHFFFAOYSA-N 1-[2-(methylamino)ethoxy]ethanol Chemical compound CNCCOC(C)O LFWVZGUDOFDLHF-UHFFFAOYSA-N 0.000 description 1
SUUUXRQFIPTUBE-UHFFFAOYSA-N 2,6-diethyl-4-methylmorpholine Chemical compound CCC1CN(C)CC(CC)O1 SUUUXRQFIPTUBE-UHFFFAOYSA-N 0.000 description 1
XXNWGSSVJMXOTP-UHFFFAOYSA-N 2-(2-morpholin-4-ylethoxy)ethanamine Chemical compound NCCOCCN1CCOCC1 XXNWGSSVJMXOTP-UHFFFAOYSA-N 0.000 description 1
BLIMWOGCOCPQEU-UHFFFAOYSA-N 2-(2-morpholin-4-ylethoxy)ethanol Chemical compound OCCOCCN1CCOCC1 BLIMWOGCOCPQEU-UHFFFAOYSA-N 0.000 description 1
JDVZLTWRFUQQSC-UHFFFAOYSA-N 4-(1-morpholin-4-ylethyl)morpholine Chemical compound C1COCCN1C(C)N1CCOCC1 JDVZLTWRFUQQSC-UHFFFAOYSA-N 0.000 description 1
FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
101150105088 Dele1 gene Proteins 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
238000003109 Karl Fischer titration Methods 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
ZWBALHRZGYPNNG-UHFFFAOYSA-N Monomethyl phenylphosphonate Chemical compound COP(O)(=O)C1=CC=CC=C1 ZWBALHRZGYPNNG-UHFFFAOYSA-N 0.000 description 1
QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
OXDOANYFRLHSML-UHFFFAOYSA-N dimethoxyphosphorylbenzene Chemical compound COP(=O)(OC)C1=CC=CC=C1 OXDOANYFRLHSML-UHFFFAOYSA-N 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
ZUYQAYFMISSPTF-UHFFFAOYSA-N methoxy-oxo-phenylphosphanium Chemical compound CO[P+](=O)C1=CC=CC=C1 ZUYQAYFMISSPTF-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GHZKGHQGPXBWSN-UHFFFAOYSA-N methyl(propan-2-yloxy)phosphinic acid Chemical compound CC(C)OP(C)(O)=O GHZKGHQGPXBWSN-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229940005657 pyrophosphoric acid Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1

Classifications

- 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
- C07D295/027—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 containing only one hetero ring
- 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
- 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
- C07D295/027—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 containing only one hetero ring
- C07D295/033—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 containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA252,910A 1975-06-02 1976-05-20 Methode pour la production de derives de la morpholine Expired CA1070305A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US58302275A	1975-06-02	1975-06-02

Publications (1)

Publication Number	Publication Date
CA1070305A true CA1070305A (fr)	1980-01-22

Family

ID=24331364

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA252,910A Expired CA1070305A (fr)	1975-06-02	1976-05-20	Methode pour la production de derives de la morpholine

Country Status (10)

Country	Link
JP (1)	JPS51141882A (fr)
AU (1)	AU504669B2 (fr)
BE (1)	BE842468A (fr)
CA (1)	CA1070305A (fr)
DE (1)	DE2624072A1 (fr)
FR (1)	FR2313373A1 (fr)
GB (1)	GB1492359A (fr)
IT (1)	IT1063218B (fr)
NL (1)	NL7605638A (fr)
ZA (1)	ZA763137B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2025216986A1 (fr) *	2024-04-09	2025-10-16	Dow Global Technologies Llc	Production de morpholine

1976
- 1976-05-05 GB GB18423/76A patent/GB1492359A/en not_active Expired
- 1976-05-19 JP JP51056756A patent/JPS51141882A/ja active Pending
- 1976-05-20 CA CA252,910A patent/CA1070305A/fr not_active Expired
- 1976-05-24 FR FR7615662A patent/FR2313373A1/fr active Granted
- 1976-05-26 NL NL7605638A patent/NL7605638A/xx not_active Application Discontinuation
- 1976-05-26 ZA ZA763137A patent/ZA763137B/xx unknown
- 1976-05-28 DE DE19762624072 patent/DE2624072A1/de not_active Withdrawn
- 1976-05-31 AU AU14438/76A patent/AU504669B2/en not_active Expired
- 1976-06-01 BE BE167544A patent/BE842468A/fr unknown
- 1976-06-01 IT IT23855/76A patent/IT1063218B/it active

Also Published As

Publication number	Publication date
ZA763137B (en)	1977-05-25
NL7605638A (nl)	1976-12-06
FR2313373B1 (fr)	1980-01-11
FR2313373A1 (fr)	1976-12-31
GB1492359A (en)	1977-11-16
JPS51141882A (en)	1976-12-07
IT1063218B (it)	1985-02-11
BE842468A (fr)	1976-12-01
AU1443876A (en)	1977-12-08
AU504669B2 (en)	1979-10-25
DE2624072A1 (de)	1976-12-23

Legal Events

Date	Code	Title	Description
1997-01-22	MKEX	Expiry

Publication	Publication Date	Title
CA1069136A (fr)	1980-01-01	Preparation de polyalkylene polyamines
US4036881A (en)	1977-07-19	Preparation of polyalkylene polyamines
US4103087A (en)	1978-07-25	Production of di-(N,N-disubstituted amino) alkanes
EP0155926B1 (fr)	1988-08-31	Procédé pour préparer l'acide N,N-diacétique aminométhylènephosphonique
US4448997A (en)	1984-05-15	Preparation of linear polyethylenepolyamines with an aluminum phosphate catalyst
US4026935A (en)	1977-05-31	Production of bis-(morpholino-N-alkyl) ethers
US4049657A (en)	1977-09-20	Preparation of N-(aminoalkyl)piperazine
US3005010A (en)	1961-10-17	Method for preparing dihydrocarbyloxyphosphinyl formamides
US4117227A (en)	1978-09-26	Production of n-(substituted) morpholine
GB2316945A (en)	1998-03-11	Preparation of 3-amino-1-hydroxypropane-1,1-diphosphonic acid from N-protected beta-alanine using phosphorous acid and a phosphorus chloride
JPS61236752A (ja)	1986-10-22	非環状のエチレンアミン類の製造法
EP0078000B1 (fr)	1986-05-28	Procédé pour la préparation d'allylamines à partir d'allyl alcool
EP0093434B1 (fr)	1986-08-13	Préparation de polyalkylène polyamines
US4931585A (en)	1990-06-05	Process for preparing N-phosphono-methyl-imino-diacetic acid
US4092316A (en)	1978-05-30	Synthesis of C-alkyl-triethylenediamines
CS239903B2 (en)	1986-01-16	Processing of aminomethyl phosphoric acid derivatives
US5639916A (en)	1997-06-17	Amination of allylic alcohols
CA1078382A (fr)	1980-05-27	Production de composes bis-(n,n-amino disubstitue)
CA1074312A (fr)	1980-03-25	Production d'un compose a base de n,n-piperazine disubstituee
CA1074317A (fr)	1980-03-25	Production d'un compose a base de n-piperazine substituee
CA1092114A (fr)	1980-12-23	Procede d'obtention de composes de la n-(radical substitue) morpholine
CA1074314A (fr)	1980-03-25	Preparation d'un compose a base de morpholine
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HU218867B (hu)	2000-12-28	Eljárás amino-metánfoszfonsav előállítására, valamint eljárás N-(foszfono-metil)-glicin előállítására amino-metánfoszfonsavból