US3321507A - Process for the production of unsaturated nitriles - Google Patents
Process for the production of unsaturated nitriles Download PDFInfo
- Publication number
- US3321507A US3321507A US356045A US35604564A US3321507A US 3321507 A US3321507 A US 3321507A US 356045 A US356045 A US 356045A US 35604564 A US35604564 A US 35604564A US 3321507 A US3321507 A US 3321507A
- Authority
- US
- United States
- Prior art keywords
- molar
- acrylonitrile
- ammonia
- molar ratio
- olefins
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000002825 nitriles Chemical class 0.000 title description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 23
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 8
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 6
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims description 2
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 150000001336 alkenes Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 5
- 229910052750 molybdenum Inorganic materials 0.000 description 5
- 239000011733 molybdenum Substances 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007792 gaseous phase Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 2
- 229940010552 ammonium molybdate Drugs 0.000 description 2
- 235000018660 ammonium molybdate Nutrition 0.000 description 2
- 239000011609 ammonium molybdate Substances 0.000 description 2
- 150000001621 bismuth Chemical class 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 239000011964 heteropoly acid Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- MXUPILKWZJJDFH-UHFFFAOYSA-N acetonitrile;prop-2-enenitrile Chemical compound CC#N.C=CC#N MXUPILKWZJJDFH-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ALTWGIIQPLQAAM-UHFFFAOYSA-N metavanadate Chemical compound [O-][V](=O)=O ALTWGIIQPLQAAM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000002317 scanning near-field acoustic microscopy Methods 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/31—Chromium, molybdenum or tungsten combined with bismuth
-
- 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
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Definitions
- ammoxydation reaction has been known for a long time, which takes place when an olefin is reacted in the gaseous phase, with oxygen or ammonia in the presence of suitable catalysts, obtaining nitrogen compounds which in suitable conditions are prevailingly unsaturated nitriles.
- Acrylonitrile is obtained by ammoxydation of propylene.
- catalysts the literature indicates a vast range of metals from the End to the VIIth group of the periodic system or their compounds, for instance oxides or mixtures thereof.
- the known processes have not revealed so far the possibility of obtaining acrylonitrile starting from olefinic mixtures containing both propylene and butylenes, which however would be very convenient and advantageous.
- one operates with mixtures of olefins, oxygen, ammonia, in which the olefins are overall (C +C.,) in molar quantities smaller with respect to oxygen, and about equal or smaller with respect to ammonia.
- the active part of the catalysts employed, which are conveniently supported, may be mixtures of oxides of molybdenum, vanadium and bismuth, or be other compounds or mixtures of compounds, in particular, the product of the calcination of a bismuth salt of a heteropolyacid of vanadium or molybdenum.
- the oxygen should be fed in ratios to said overall quantity of olefins higher than 1 and preferably not higher than 2. It is advantageous that the oxygen should be fed with convenient diluents, such as nitrogen or carbon dioxide. In particular it is convenient to feed air.
- the time of contact is not critical, showing an optimum for durations shorter than 30 and preferably shorter than 10 seconds and equal at least to 0.5 second.
- the presence of saturated hydrocarbons in the feed does not cause any inconveniences.
- the catalyst is generally supported on kieselguhr, celite or carborundum. In this case it can be prepared by mixing the active part with a support, kneading and then drying the whole. The solid mass obtained is ground to a convenient grain size and is then tabletted after previous addition of a suitable substance having the func tion of a binder.
- the tabletted catalyst is charged into the reactor and is activated in situ by oxygen or air at 480 to 540 C., the optimum being shifted towards the temperatures closest to the upper limit.
- a further advantage of the present invention is the absence of any danger in connection with the production of acrylonitrile, since no formation of acrolein has been noticed, the mixtures of which with air are notoriously explosive, or at any rate the formation of this aldehyde has always been below the explosive limits. It is obvious that it is possible to convert into nitriles, in the manner described in the present patent application, not only the mixtures of olefins but also the individual olefins that normally form part of the mixtures.
- EXAMPLE 1 2700 g. of Bi(NO -5H O, 1200 g. of ammonium molybdate and 70 g. of ammonium metavanadate, are calcined separately in a mufile at 450 to 500 C. and then mixed.
- a catalyst is obtained consisting of a mixture of oxides of vanadium, molybdenum and bismuth.
- the active part so obtained is mixed with 1 kg. of celite, kneaded with water, extruded and reduced into pellets.
- the catalyst so prepared is charged, after drying, into the reactor constituted by a steel tube, and is activated in situ with air for 8 hours at 500 C.
- EXAMPLE 2 2700 g. of Bi(NO -5H O are dissolved in 300 ml, of nitric acid diluted with one liter of water. Another solution is prepared apart by dissolving 1200 g. of ammonium molybdate (81% of M00 and 70 g. of metavanadate of ammonium in 1 liter of water saturated with ammonia, then diluting the Whole with 1500 ml. of water. After having heated the two solutions up to C., the second solution is added to the first one, keeping the whole under stirring. A sludgy paste of brown colour is obtained which when cooled and washed with water and dried, shows on analysis the following results:
- the active part so obtained is mixed with 1 kg. of kieselguhr and with water: the paste so prepared is extruded and reduced into pellets. These are dried and calcined in a muflle at 450 to 500 C. for 12 hours.
- One liter of the catalyst so prepared is charged into the same synthesis reactor of Example 1 and then activated by a stream of oxygen at 510 C. for 8 hours.
- the volumetric ratios in the feed between refinery gas, ammonia, air and water are 1/ 1/ 3.5/20.
- the yield of useful products is 79% (again calculated with respect to the unsaturated compounds).
- a process for the production of acrylonitrile in which a refinery gas consisting essentially of C H +C H in a molar ratio range of 0.6% to 3.7%, of C H in a molar ratio range of 11.8% to 22.1%, of C H in a molar range of 19.2% to 28.9%, of iso C H in a molar range of 12.5% to 18.6%, of C H in a molar ratio range of 8.2% to 20.1% and of C H in a molar ratio range of 22.7% to 33.3%, the sum total of said components in the gas being essentially is reacted with ammonia and oxygen in the presence of an oxidation catalyst consisting essentially of a mixture of bismuth oxide, molybdenum oxide, and vanadium oxide, where the vanadium content is between 0.5 and 3%, the reaction being conducted at a temperature between 450 C. and 525 C. and for from 0.5 to 30 seconds.
- a refinery gas consisting essentially of C H +C H
- reaction time is less than ten seconds.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT660363 | 1963-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3321507A true US3321507A (en) | 1967-05-23 |
Family
ID=11121244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US356045A Expired - Lifetime US3321507A (en) | 1963-04-01 | 1964-03-31 | Process for the production of unsaturated nitriles |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3321507A (en&quot) |
| BE (1) | BE643909A (en&quot) |
| CA (1) | CA759474A (en&quot) |
| CH (1) | CH441287A (en&quot) |
| FR (1) | FR1382521A (en&quot) |
| GB (1) | GB1065552A (en&quot) |
| IT (1) | IT690486A (en&quot) |
| LU (1) | LU45402A1 (en&quot) |
| NL (2) | NL294731A (en&quot) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3492248A (en) * | 1965-06-30 | 1970-01-27 | Snam Progetti | Molybdenum - bismuth - vanadium ternary compounds useful as oxidation catalysts |
| US3541129A (en) * | 1966-08-12 | 1970-11-17 | Ube Kogyo Kk | Process for the preparation of acrylonitrile |
| US3875204A (en) * | 1972-08-01 | 1975-04-01 | Sir Soc Italiana Resine Spa | Process for the production of acrylonitrile |
| US4565658A (en) * | 1979-12-17 | 1986-01-21 | Monsanto Company | Oxidation and ammoxidation process |
| US5220090A (en) * | 1989-11-15 | 1993-06-15 | Mitsui Toatsu Chemicals, Inc. | Method for preparing unsaturated compounds |
| US5220049A (en) * | 1989-11-15 | 1993-06-15 | Mitsui Toatsu Chemicals, Inc. | Method for preparing unsaturated compounds |
| US5268497A (en) * | 1992-02-24 | 1993-12-07 | The Boc Group, Inc. | Process for the production of nitriles |
| US5756802A (en) * | 1995-09-11 | 1998-05-26 | Air Products And Chemicals, Inc. | Ammoxidation process for producing acetonitrile |
| US20090032057A1 (en) * | 2007-02-01 | 2009-02-05 | Henkel Corporation | Acid inhibitor compositions for metal cleaning and/or pickling |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3142697A (en) * | 1961-05-31 | 1964-07-28 | Shell Oil Co | Production of lower aliphatic nitriles |
| US3161670A (en) * | 1960-12-12 | 1964-12-15 | Shell Oil Co | Preparation of olefinic compounds |
| US3164627A (en) * | 1960-03-09 | 1965-01-05 | Asahi Chemical Ind | Method for preparing unsaturated aliphatic nitriles |
| US3173957A (en) * | 1961-08-21 | 1965-03-16 | Eastman Kodak Co | Process for the preparation of acrolein |
| US3186955A (en) * | 1962-05-28 | 1965-06-01 | Standard Oil Co | Bismuth-molybdenum oxidation catalyst promoted with a ba-si oxide mixture |
| US3226421A (en) * | 1961-07-14 | 1965-12-28 | Edison Soc | Catalytic process for the preparation of nitriles |
| US3232978A (en) * | 1961-11-30 | 1966-02-01 | Toyo Rayon Co Ltd | Preparation of acrylonitrile |
-
0
- NL NL121947D patent/NL121947C/xx active
- CA CA759474A patent/CA759474A/en not_active Expired
- IT IT690486D patent/IT690486A/it unknown
- NL NL294731D patent/NL294731A/xx unknown
-
1964
- 1964-02-11 LU LU45402D patent/LU45402A1/xx unknown
- 1964-02-11 FR FR963375A patent/FR1382521A/fr not_active Expired
- 1964-02-17 BE BE643909D patent/BE643909A/xx unknown
- 1964-02-17 CH CH184664A patent/CH441287A/it unknown
- 1964-03-04 GB GB9238/64A patent/GB1065552A/en not_active Expired
- 1964-03-31 US US356045A patent/US3321507A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3164627A (en) * | 1960-03-09 | 1965-01-05 | Asahi Chemical Ind | Method for preparing unsaturated aliphatic nitriles |
| US3161670A (en) * | 1960-12-12 | 1964-12-15 | Shell Oil Co | Preparation of olefinic compounds |
| US3142697A (en) * | 1961-05-31 | 1964-07-28 | Shell Oil Co | Production of lower aliphatic nitriles |
| US3226421A (en) * | 1961-07-14 | 1965-12-28 | Edison Soc | Catalytic process for the preparation of nitriles |
| US3173957A (en) * | 1961-08-21 | 1965-03-16 | Eastman Kodak Co | Process for the preparation of acrolein |
| US3232978A (en) * | 1961-11-30 | 1966-02-01 | Toyo Rayon Co Ltd | Preparation of acrylonitrile |
| US3186955A (en) * | 1962-05-28 | 1965-06-01 | Standard Oil Co | Bismuth-molybdenum oxidation catalyst promoted with a ba-si oxide mixture |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3492248A (en) * | 1965-06-30 | 1970-01-27 | Snam Progetti | Molybdenum - bismuth - vanadium ternary compounds useful as oxidation catalysts |
| US3541129A (en) * | 1966-08-12 | 1970-11-17 | Ube Kogyo Kk | Process for the preparation of acrylonitrile |
| US3875204A (en) * | 1972-08-01 | 1975-04-01 | Sir Soc Italiana Resine Spa | Process for the production of acrylonitrile |
| US4565658A (en) * | 1979-12-17 | 1986-01-21 | Monsanto Company | Oxidation and ammoxidation process |
| US5220090A (en) * | 1989-11-15 | 1993-06-15 | Mitsui Toatsu Chemicals, Inc. | Method for preparing unsaturated compounds |
| US5220049A (en) * | 1989-11-15 | 1993-06-15 | Mitsui Toatsu Chemicals, Inc. | Method for preparing unsaturated compounds |
| US5321186A (en) * | 1989-11-15 | 1994-06-14 | Mitsui Toatsu Chemicals, Inc. | Method for preparing unsaturated compounds |
| US5268497A (en) * | 1992-02-24 | 1993-12-07 | The Boc Group, Inc. | Process for the production of nitriles |
| US5756802A (en) * | 1995-09-11 | 1998-05-26 | Air Products And Chemicals, Inc. | Ammoxidation process for producing acetonitrile |
| US20090032057A1 (en) * | 2007-02-01 | 2009-02-05 | Henkel Corporation | Acid inhibitor compositions for metal cleaning and/or pickling |
| US8278258B2 (en) | 2007-02-01 | 2012-10-02 | Henkel Ag & Co. Kgaa | Acid inhibitor compositions for metal cleaning and/or pickling |
Also Published As
| Publication number | Publication date |
|---|---|
| NL294731A (en&quot) | |
| LU45402A1 (en&quot) | 1965-08-11 |
| IT690486A (en&quot) | |
| CH441287A (it) | 1967-08-15 |
| FR1382521A (fr) | 1964-12-18 |
| CA759474A (en) | 1967-05-23 |
| GB1065552A (en) | 1967-04-19 |
| BE643909A (en&quot) | 1964-08-17 |
| NL121947C (en&quot) |
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