CA2336461A1 - Production d'un diacide aliphatique et d'oxyde nitreux - Google Patents
Production d'un diacide aliphatique et d'oxyde nitreux Download PDFInfo
- Publication number
- CA2336461A1 CA2336461A1 CA002336461A CA2336461A CA2336461A1 CA 2336461 A1 CA2336461 A1 CA 2336461A1 CA 002336461 A CA002336461 A CA 002336461A CA 2336461 A CA2336461 A CA 2336461A CA 2336461 A1 CA2336461 A1 CA 2336461A1
- Authority
- CA
- Canada
- Prior art keywords
- nitrous oxide
- ammonia
- stream
- reactor
- product stream
- 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.)
- Abandoned
Links
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 title claims abstract description 317
- 239000001272 nitrous oxide Substances 0.000 title claims abstract description 140
- 238000000034 method Methods 0.000 title claims abstract description 82
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 156
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 62
- 230000003647 oxidation Effects 0.000 claims abstract description 24
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 24
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract 3
- 239000007789 gas Substances 0.000 claims description 91
- 239000000047 product Substances 0.000 claims description 74
- 239000003054 catalyst Substances 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- 229910001868 water Inorganic materials 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 230000001590 oxidative effect Effects 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 16
- 229910001882 dioxygen Inorganic materials 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 239000011261 inert gas Substances 0.000 claims description 11
- 239000007800 oxidant agent Substances 0.000 claims description 10
- -1 alcohol compound Chemical class 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 238000004064 recycling Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- 230000000640 hydroxylating effect Effects 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims 2
- 229910002089 NOx Inorganic materials 0.000 claims 1
- ATNZEYOLAMGQPU-UHFFFAOYSA-N azane nitrous oxide Chemical compound N.[O-][N+]#N ATNZEYOLAMGQPU-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 71
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 56
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 23
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 16
- 239000012467 final product Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000000926 separation method Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 230000033444 hydroxylation Effects 0.000 description 6
- 238000005805 hydroxylation reaction Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- KYAZRUPZRJALEP-UHFFFAOYSA-N bismuth manganese Chemical compound [Mn].[Bi] KYAZRUPZRJALEP-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229960003753 nitric oxide Drugs 0.000 description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
- 239000012495 reaction gas Substances 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- PRORZGWHZXZQMV-UHFFFAOYSA-N azane;nitric acid Chemical compound N.O[N+]([O-])=O PRORZGWHZXZQMV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- CVAXSQLWEFGANM-UHFFFAOYSA-N N#[N+][O-].C1=CC=CC=C1 Chemical compound N#[N+][O-].C1=CC=CC=C1 CVAXSQLWEFGANM-UHFFFAOYSA-N 0.000 description 1
- PDNNQADNLPRFPG-UHFFFAOYSA-N N.[O] Chemical compound N.[O] PDNNQADNLPRFPG-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitrogen oxide(NO) Natural products O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 235000018087 Spondias lutea Nutrition 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000010543 cumene process Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/245—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of keto groups or secondary alcohol groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/20—Nitrogen oxides; Oxyacids of nitrogen; Salts thereof
- C01B21/22—Nitrous oxide (N2O)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
La présente invention concerne un procédé aboutissant à la production d'un diacide aliphatique et d'oxyde nitreux. L'acide dibasique aliphatique produit résulte de l'oxydation d'un composé aromatique hydrolylé avec de l'oxyde nitreux résultant de la réduction d'un mélange contenant un courant de gaz renfermant un NOx réutilisé pour la fabrication du diacide aliphatique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11064198A | 1998-07-06 | 1998-07-06 | |
| US09/110,641 | 1998-07-06 | ||
| PCT/US1999/013745 WO2000001654A1 (fr) | 1998-07-06 | 1999-06-17 | Production d'un diacide aliphatique et d'oxyde nitreux |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2336461A1 true CA2336461A1 (fr) | 2000-01-13 |
Family
ID=22334120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002336461A Abandoned CA2336461A1 (fr) | 1998-07-06 | 1999-06-17 | Production d'un diacide aliphatique et d'oxyde nitreux |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1115685A1 (fr) |
| JP (1) | JP2002519399A (fr) |
| KR (1) | KR20010071732A (fr) |
| CN (1) | CN1314877A (fr) |
| AU (1) | AU4576199A (fr) |
| BR (1) | BR9911867A (fr) |
| CA (1) | CA2336461A1 (fr) |
| PL (1) | PL345383A1 (fr) |
| WO (1) | WO2000001654A1 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6312657B1 (en) * | 1998-08-25 | 2001-11-06 | Exxonmobil Oil Corporation | Production of nitrous oxide |
| DE102004046167A1 (de) | 2004-09-23 | 2006-04-06 | Basf Ag | Verfahren zur Reinigung und Aufkonzentrierung von Distickstoffmonoxid |
| DE102005055588A1 (de) | 2005-11-22 | 2007-05-24 | Basf Ag | Verfahren zur Isolierung von N2O |
| EP2091866B1 (fr) | 2006-12-11 | 2013-07-10 | Basf Se | Procédé d'isolement de n2o |
| KR101579997B1 (ko) | 2008-04-02 | 2015-12-23 | 바스프 에스이 | Ｎ２０의 정제 방법 |
| ES2384751T3 (es) | 2008-04-02 | 2012-07-11 | Basf Se | Proceso para purificar óxido nitroso |
| EP2334629B1 (fr) * | 2008-08-29 | 2016-08-10 | Basf Se | Procédé de préparation de cétones cycliques |
| US8475571B2 (en) | 2010-04-23 | 2013-07-02 | General Electric Company | System for gas purification and recovery with multiple solvents |
| GB201019701D0 (en) | 2010-11-19 | 2011-01-05 | Invista Tech Sarl | Reaction process |
| CN103130203B (zh) * | 2011-11-29 | 2014-08-20 | 岳阳昌德化工实业有限公司 | 一种一氧化二氮的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2844626A (en) * | 1955-05-27 | 1958-07-22 | Goodyear Tire & Rubber | Process for the manufacture of adipic acid |
| FR2705036B1 (fr) * | 1993-05-10 | 1995-06-16 | Paroisse Sa Grande | Procédé pour abaisser la teneur en protoxyde d'azote dans les effluents gazeux, en particulier dans ceux qui sont issus de synthèses par oxydation nitrique. |
-
1999
- 1999-06-17 CA CA002336461A patent/CA2336461A1/fr not_active Abandoned
- 1999-06-17 JP JP2000558060A patent/JP2002519399A/ja not_active Withdrawn
- 1999-06-17 KR KR1020017000097A patent/KR20010071732A/ko not_active Withdrawn
- 1999-06-17 BR BR9911867-0A patent/BR9911867A/pt not_active IP Right Cessation
- 1999-06-17 WO PCT/US1999/013745 patent/WO2000001654A1/fr not_active Ceased
- 1999-06-17 PL PL99345383A patent/PL345383A1/xx unknown
- 1999-06-17 CN CN99810195A patent/CN1314877A/zh active Pending
- 1999-06-17 EP EP99928770A patent/EP1115685A1/fr not_active Withdrawn
- 1999-06-17 AU AU45761/99A patent/AU4576199A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BR9911867A (pt) | 2001-03-27 |
| EP1115685A1 (fr) | 2001-07-18 |
| AU4576199A (en) | 2000-01-24 |
| WO2000001654A1 (fr) | 2000-01-13 |
| JP2002519399A (ja) | 2002-07-02 |
| KR20010071732A (ko) | 2001-07-31 |
| CN1314877A (zh) | 2001-09-26 |
| PL345383A1 (en) | 2001-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20040617 |