CS345591A3 - Process for preparing anhydrides and nitriles and apparatus for making same - Google Patents
Process for preparing anhydrides and nitriles and apparatus for making same Download PDFInfo
- Publication number
- CS345591A3 CS345591A3 CS913455A CS345591A CS345591A3 CS 345591 A3 CS345591 A3 CS 345591A3 CS 913455 A CS913455 A CS 913455A CS 345591 A CS345591 A CS 345591A CS 345591 A3 CS345591 A3 CS 345591A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrocarbon
- carbon monoxide
- gas
- reactor
- stream
- Prior art date
Links
- 150000002825 nitriles Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 16
- 150000008064 anhydrides Chemical class 0.000 title description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 162
- 229930195733 hydrocarbon Natural products 0.000 claims description 161
- 239000004215 Carbon black (E152) Substances 0.000 claims description 152
- 239000007789 gas Substances 0.000 claims description 98
- 238000000034 method Methods 0.000 claims description 78
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 77
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 68
- 239000000047 product Substances 0.000 claims description 66
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 64
- -1 cyclic anhydrides Chemical class 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
- 239000001569 carbon dioxide Substances 0.000 claims description 36
- 239000001301 oxygen Substances 0.000 claims description 36
- 238000007254 oxidation reaction Methods 0.000 claims description 35
- 230000003647 oxidation Effects 0.000 claims description 29
- 230000036961 partial effect Effects 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 22
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 13
- 238000001179 sorption measurement Methods 0.000 claims description 13
- 239000012808 vapor phase Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 10
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 10
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical group CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 4
- 239000001282 iso-butane Substances 0.000 claims description 4
- 239000012263 liquid product Substances 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 229920002683 Glycosaminoglycan Polymers 0.000 claims 1
- 229910002090 carbon oxide Inorganic materials 0.000 claims 1
- 239000008246 gaseous mixture Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 238000004880 explosion Methods 0.000 description 9
- 239000011261 inert gas Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 6
- 238000009825 accumulation Methods 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910001935 vanadium oxide Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical group [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- LUYWGGWGYMURNR-UHFFFAOYSA-M [O-2].[O-2].[OH-].O.P.[V+5] Chemical compound [O-2].[O-2].[OH-].O.P.[V+5] LUYWGGWGYMURNR-UHFFFAOYSA-M 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- WFAADKZBQQNDRX-UHFFFAOYSA-N ctk0h7075 Chemical compound FP=O WFAADKZBQQNDRX-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 238000013386 optimize process Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 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
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/18—Preparation of carboxylic acid nitriles by reaction of ammonia or amines with compounds containing carbon-to-carbon multiple bonds other than in six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
-
- 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
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl 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
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
-
- 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
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61343790A | 1990-11-14 | 1990-11-14 | |
| US69320791A | 1991-04-30 | 1991-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS345591A3 true CS345591A3 (en) | 1992-06-17 |
Family
ID=27087023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS913455A CS345591A3 (en) | 1990-11-14 | 1991-11-14 | Process for preparing anhydrides and nitriles and apparatus for making same |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5278319A (de) |
| EP (1) | EP0486286A3 (de) |
| JP (1) | JPH04288023A (de) |
| KR (1) | KR940009530B1 (de) |
| CN (1) | CN1033749C (de) |
| AU (1) | AU652195B2 (de) |
| CA (1) | CA2055395A1 (de) |
| CS (1) | CS345591A3 (de) |
| HU (1) | HUT58680A (de) |
| IE (1) | IE913947A1 (de) |
| PL (1) | PL292372A1 (de) |
| RU (1) | RU2058978C1 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5466837A (en) * | 1993-09-30 | 1995-11-14 | The Boc Group, Inc. | Process for the production of hydrocarbon partial oxidation products |
| TW338064B (en) * | 1995-06-01 | 1998-08-11 | Boc Group Inc | Process for the production of petrochemicals |
| US5672196A (en) * | 1995-08-01 | 1997-09-30 | The Boc Group, Inc. | Process and apparatus for the separation of gases |
| US5659077A (en) * | 1996-03-22 | 1997-08-19 | Natural Resources Canada | Production of acetic acid from methane |
| US6018060A (en) * | 1997-07-10 | 2000-01-25 | Membrane Technology And Research, Inc. | Membrane process and apparatus for argon purging from oxidation reactors |
| BE1012101A6 (fr) * | 1998-06-23 | 2000-05-02 | Pantochim Sa | Procede de conversion a haut rendement de n-butane en anhydride maleique par recyclage des gaz uses. |
| DE69916217T2 (de) * | 1998-11-27 | 2005-04-07 | Mitsubishi Chemical Corp. | Verfahren zur Herstellung von Maleinsäureanhydrid |
| EP1055670B1 (de) * | 1999-05-25 | 2008-02-20 | Mitsubishi Chemical Corporation | Verfahren zur Herstellung von Maleinsäureanhydrid |
| AU2001296666A1 (en) * | 2000-10-11 | 2002-04-22 | Union Carbide Chemicals And Plastics Technology Corporation | Processes for oxidizing hydrocarbyl moieties to carboxylic acids and anhydrides |
| CN108017557B (zh) * | 2017-12-06 | 2020-11-24 | 中国科学院兰州化学物理研究所苏州研究院 | 一种制备腈类化合物的氰化方法 |
| CN117326938A (zh) * | 2022-06-24 | 2024-01-02 | 中国石油化工股份有限公司 | 环己烷氧化的方法及其产物 |
| CN117326928A (zh) * | 2022-06-24 | 2024-01-02 | 中国石油化工股份有限公司 | 尾气回用的环己烷氧化的方法和产物及系统 |
| WO2025062466A1 (en) | 2023-09-19 | 2025-03-27 | Conser Spa | Gas recycle maleic anydride process for high productivity and low carbon emissions |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB887667A (en) * | 1959-04-06 | 1962-01-24 | Richard Klar | Process for carrying out chemical reactions |
| US3904652A (en) * | 1972-11-16 | 1975-09-09 | Standard Oil Co Indiana | Recycle process for oxidation of n-butane to maleic anhydride |
| US3868400A (en) * | 1973-05-04 | 1975-02-25 | Sun Research Development | Process for vapor phase ammoxidation |
| US4118402A (en) * | 1974-12-02 | 1978-10-03 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Preparation of maleic anhydride |
| US4000178A (en) * | 1975-09-19 | 1976-12-28 | Monsanto Company | Paraffin ammoxidation process |
| US4127591A (en) * | 1975-12-26 | 1978-11-28 | Mitsubishi Chemical Industries Ltd. | Method of producing maleic anhydride |
| US4316856A (en) * | 1979-12-28 | 1982-02-23 | The Standard Oil Co. | Molybdenum-promoted antimony phosphate oxide complex catalysts also containing at least one of bismuth and tellurium |
| US4322368A (en) * | 1979-12-28 | 1982-03-30 | The Standard Oil Co. | Copper-promoted antimony phosphate oxide complex catalysts |
| US4339394A (en) * | 1980-10-01 | 1982-07-13 | The Standard Oil Co. | Process of ammoxidation of olefins in the presence of multiply promoted Sn-Sb oxide catalysts |
| US4609502A (en) * | 1985-02-14 | 1986-09-02 | The Halcon Sd Group, Inc. | Process for preparing unsaturated nitriles from alkanes |
| US4754049A (en) * | 1985-02-14 | 1988-06-28 | Atlantic Richfield Company | Process for preparing unsaturated nitriles from alkanes |
| US4863330A (en) * | 1987-07-15 | 1989-09-05 | Northrop Corporation | Composite fastener and method of manufacture |
| CA1320735C (en) * | 1987-11-24 | 1993-07-27 | Ramakrishnan Ramachandran | Process for the production of nitriles and anhydrides |
| US4849538A (en) * | 1988-03-23 | 1989-07-18 | The Boc Group, Inc. | Process for the production of nitriles |
| US4987239A (en) * | 1988-04-06 | 1991-01-22 | The Boc Group, Inc. | Process for the production of anhydrides |
| US4870201A (en) * | 1988-12-08 | 1989-09-26 | The Boc Group, Inc. | Process for the production of nitriles |
| US4943650A (en) * | 1989-01-30 | 1990-07-24 | The Boc Group, Inc. | Process for the production of nitriles |
| US5126463A (en) * | 1990-10-31 | 1992-06-30 | The Boc Group, Inc. | Process for the production of anhydrides |
-
1991
- 1991-11-11 HU HU913527A patent/HUT58680A/hu unknown
- 1991-11-12 AU AU87771/91A patent/AU652195B2/en not_active Ceased
- 1991-11-13 PL PL29237291A patent/PL292372A1/xx unknown
- 1991-11-13 EP EP19910310483 patent/EP0486286A3/en not_active Withdrawn
- 1991-11-13 IE IE394791A patent/IE913947A1/en not_active Application Discontinuation
- 1991-11-13 RU SU915010307A patent/RU2058978C1/ru active
- 1991-11-13 CA CA002055395A patent/CA2055395A1/en not_active Abandoned
- 1991-11-13 KR KR1019910020156A patent/KR940009530B1/ko not_active Expired - Fee Related
- 1991-11-14 CN CN91111545A patent/CN1033749C/zh not_active Expired - Fee Related
- 1991-11-14 CS CS913455A patent/CS345591A3/cs unknown
- 1991-11-14 JP JP3299114A patent/JPH04288023A/ja active Pending
-
1992
- 1992-04-14 US US07/868,594 patent/US5278319A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR940009530B1 (ko) | 1994-10-14 |
| AU8777191A (en) | 1992-05-21 |
| HUT58680A (en) | 1992-03-30 |
| EP0486286A2 (de) | 1992-05-20 |
| CN1062343A (zh) | 1992-07-01 |
| IE913947A1 (en) | 1992-05-20 |
| RU2058978C1 (ru) | 1996-04-27 |
| JPH04288023A (ja) | 1992-10-13 |
| CN1033749C (zh) | 1997-01-08 |
| CA2055395A1 (en) | 1992-05-15 |
| US5278319A (en) | 1994-01-11 |
| PL292372A1 (en) | 1992-07-27 |
| EP0486286A3 (en) | 1992-09-16 |
| AU652195B2 (en) | 1994-08-18 |
| HU913527D0 (en) | 1992-01-28 |
| KR920009814A (ko) | 1992-06-25 |
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