CA1089858A - Morpholine process - Google Patents
Morpholine processInfo
- Publication number
- CA1089858A CA1089858A CA268,311A CA268311A CA1089858A CA 1089858 A CA1089858 A CA 1089858A CA 268311 A CA268311 A CA 268311A CA 1089858 A CA1089858 A CA 1089858A
- Authority
- CA
- Canada
- Prior art keywords
- ammonia
- stream
- hydrogen
- glycol
- gaseous
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 51
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract description 35
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 182
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 239000001257 hydrogen Substances 0.000 claims abstract description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 55
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000007789 gas Substances 0.000 claims abstract description 31
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 morpholine compound Chemical class 0.000 claims abstract description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 63
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 38
- 239000007788 liquid Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 238000005201 scrubbing Methods 0.000 abstract description 24
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- 239000012530 fluid Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 21
- 229940113083 morpholine Drugs 0.000 description 17
- 238000011084 recovery Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000002699 waste material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 208000036366 Sensation of pressure Diseases 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000005915 ammonolysis reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000001577 simple distillation Methods 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
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Gas Separation By Absorption (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Industrial Gases (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US644,696 | 1975-12-29 | ||
| US05/644,696 US4091218A (en) | 1975-12-29 | 1975-12-29 | Morpholine process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1089858A true CA1089858A (en) | 1980-11-18 |
Family
ID=24585980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA268,311A Expired CA1089858A (en) | 1975-12-29 | 1976-12-20 | Morpholine process |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4091218A (en:Method) |
| JP (1) | JPS5283383A (en:Method) |
| AU (1) | AU500402B2 (en:Method) |
| BE (1) | BE849642A (en:Method) |
| BR (1) | BR7607782A (en:Method) |
| CA (1) | CA1089858A (en:Method) |
| DE (1) | DE2655549A1 (en:Method) |
| FR (1) | FR2337131A1 (en:Method) |
| GB (1) | GB1495239A (en:Method) |
| IT (1) | IT1123700B (en:Method) |
| NL (1) | NL7614005A (en:Method) |
| ZA (1) | ZA766666B (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650502A (en) * | 1979-01-26 | 1987-03-17 | United States Steel Corporation | Pressurized gaseous aqueous ammonia separation system |
| US4645834A (en) * | 1980-03-17 | 1987-02-24 | Air Products And Chemicals, Inc. | Synthesis of heterocyclic amines via the reaction of dialkylene glycol and ammonia |
| US4647663A (en) * | 1982-05-25 | 1987-03-03 | Air Products And Chemicals, Inc. | Synthesis of morpholine |
| DE3905034A1 (de) * | 1989-02-18 | 1990-08-23 | Fuderer Michael | Ammoniaksyntheseverfahren mit hochdruckstripper |
| DE10116958A1 (de) * | 2001-04-05 | 2002-10-17 | Uhde Gmbh | Verfahren zur NH¶3¶-Abscheidung aus Sythesegas sowie Vorrichtung zur Durchführung des Verfahrens |
| AR040962A1 (es) * | 2002-08-09 | 2005-04-27 | Novartis Ag | Compuestos derivados de tiazol 1,3-2-ona, composicion farmaceutica y proceso de preparacion del compuesto |
| GB0426164D0 (en) * | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| GB0613154D0 (en) * | 2006-06-30 | 2006-08-09 | Novartis Ag | Organic Compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3151112A (en) * | 1956-05-21 | 1964-09-29 | Jefferson Chem Co Inc | Process for the preparation of morpholines |
| US3151113A (en) * | 1962-02-19 | 1964-09-29 | Jefferson Chem Co Inc | Nu-alkyl morpholine production |
| US3344585A (en) * | 1967-05-12 | 1967-10-03 | Eugene G Hollowell | Method for recovering ammonia from gaseous mixture |
| DE2317603C3 (de) * | 1973-04-07 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zur zumindest teilweisen Trennung von Ammoniak und Kohlendioxid enthaltenden Gasgemischen |
-
1975
- 1975-12-29 US US05/644,696 patent/US4091218A/en not_active Expired - Lifetime
-
1976
- 1976-10-15 JP JP12304176A patent/JPS5283383A/ja active Pending
- 1976-11-04 GB GB45851/76A patent/GB1495239A/en not_active Expired
- 1976-11-08 ZA ZA00766666A patent/ZA766666B/xx unknown
- 1976-11-15 AU AU19634/76A patent/AU500402B2/en not_active Expired
- 1976-11-22 BR BR7607782A patent/BR7607782A/pt unknown
- 1976-12-08 DE DE19762655549 patent/DE2655549A1/de not_active Ceased
- 1976-12-17 NL NL7614005A patent/NL7614005A/xx not_active Application Discontinuation
- 1976-12-17 FR FR7638116A patent/FR2337131A1/fr active Granted
- 1976-12-20 BE BE173463A patent/BE849642A/xx unknown
- 1976-12-20 CA CA268,311A patent/CA1089858A/en not_active Expired
- 1976-12-28 IT IT30932/76A patent/IT1123700B/it active
-
1977
- 1977-10-19 US US05/843,400 patent/US4119412A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BR7607782A (pt) | 1977-10-11 |
| BE849642A (fr) | 1977-06-20 |
| IT1123700B (it) | 1986-04-30 |
| FR2337131A1 (fr) | 1977-07-29 |
| FR2337131B1 (en:Method) | 1981-01-23 |
| JPS5283383A (en) | 1977-07-12 |
| ZA766666B (en) | 1978-03-29 |
| AU500402B2 (en) | 1979-05-17 |
| NL7614005A (nl) | 1977-07-01 |
| DE2655549A1 (de) | 1977-07-07 |
| US4091218A (en) | 1978-05-23 |
| GB1495239A (en) | 1977-12-14 |
| US4119412A (en) | 1978-10-10 |
| AU1963476A (en) | 1978-05-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4368059A (en) | Process of removing H2 S, CO2, COS and mercaptans from gases by absorption | |
| US4545965A (en) | Process of selective separation of hydrogen sulfide from gaseous mixtures containing also carbon dioxide | |
| CA1246606A (en) | Process for the preparation of formic acid | |
| US5304361A (en) | Removal of hydrogen sulfide | |
| US4497967A (en) | Process for the preparation of ethanol from methanol, carbon monoxide _and hydrogen | |
| SU893126A3 (ru) | Способ очистки уксусной кислоты | |
| AU667434B2 (en) | Fusel oil stripping | |
| GB1560905A (en) | Removal of co2 and/or h2s and/or cos from gases containing these constituents | |
| EP0088485B1 (en) | A process for the removal of hydrogen sulfide from gaseous mixtures with strongly basic tertiary amino compounds | |
| EP0059516B1 (en) | Process for the removal of urea, ammonia and carbon dioxide from dilute aqueous solutions | |
| CA1089858A (en) | Morpholine process | |
| WO1995003874A1 (en) | Solvent composition for removing acid gases | |
| US20160068404A1 (en) | Process for heat recovery from ammonia stripper in andrussow process | |
| US5137702A (en) | Regeneration of used alkanolamine solutions | |
| EP0084943B2 (en) | Secondary and tertiary amino alcohols | |
| US4367363A (en) | Production of acetylene | |
| WO1991001960A1 (en) | Process | |
| USRE27377E (en) | Synthesis of urea | |
| US3807138A (en) | Recovery and purification of vinyl chloride venting from pvc reactors | |
| US3664930A (en) | Process for the regeneration of alkanolamines by distillation, alkali hydroxide treatment, heat, phase separation and distillation | |
| KR840001860B1 (ko) | 메탄올과 고급알콜의 "연료급" 혼합물의 제조방법 | |
| US4514379A (en) | Catalytic process for converting 2-oxazolidinones to their corresponding alkanolamines | |
| US4504675A (en) | Method for making isobutyric acid or esters thereof | |
| EP0597151A1 (en) | Method for preparing formic acid | |
| KR20190103377A (ko) | 아세트산의 제조 방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |