IL24162A - Process and catalyst for the production of aromatic nitriles - Google Patents

Process and catalyst for the production of aromatic nitriles

Info

Publication number: IL24162A
Authority: IL; Israel
Prior art keywords: catalyst; antimony; vanadium; alkyl; support
Prior art date: 1964-08-17

Application number

IL24162A

Other languages

English (en)

Original Assignee

Halcon International Inc

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.)

1964-08-17

Filing date

1965-08-16

Publication date

1969-07-30

1965-08-16 Application filed by Halcon International Inc filed Critical Halcon International Inc

1969-07-30 Publication of IL24162A publication Critical patent/IL24162A/en

Links

239000003054 catalyst Substances 0.000 title claims description 30
238000000034 method Methods 0.000 title claims description 14
-1 aromatic nitriles Chemical class 0.000 title claims description 13
238000004519 manufacturing process Methods 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 12
229910052787 antimony Inorganic materials 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 10
229910052720 vanadium Inorganic materials 0.000 claims description 9
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims description 2
150000001463 antimony compounds Chemical class 0.000 claims description 2
UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 4
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
239000000203 mixture Substances 0.000 claims 2
239000000243 solution Substances 0.000 claims 2
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 1
239000007864 aqueous solution Substances 0.000 claims 1
238000001035 drying Methods 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
229910001935 vanadium oxide Inorganic materials 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
229910021529 ammonia Inorganic materials 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 5
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
150000001491 aromatic compounds Chemical class 0.000 description 3
239000011651 chromium Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910000975 Carbon steel Inorganic materials 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
125000002015 acyclic group Chemical group 0.000 description 2
LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 2
239000010962 carbon steel Substances 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 2
229920006391 phthalonitrile polymer Polymers 0.000 description 2
239000004291 sulphur dioxide Substances 0.000 description 2
235000010269 sulphur dioxide Nutrition 0.000 description 2
150000003682 vanadium compounds Chemical class 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
CKDXMVPILZEZSP-UHFFFAOYSA-N 2-(2-methylphenyl)benzonitrile Chemical compound CC1=CC=CC=C1C1=CC=CC=C1C#N CKDXMVPILZEZSP-UHFFFAOYSA-N 0.000 description 1
YFDJCWXBKWRDPW-UHFFFAOYSA-N 4-propan-2-ylbenzonitrile Chemical compound CC(C)C1=CC=C(C#N)C=C1 YFDJCWXBKWRDPW-UHFFFAOYSA-N 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
UKUJCSBWRBWNAV-UHFFFAOYSA-N [Sn].[V] Chemical compound [Sn].[V] UKUJCSBWRBWNAV-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
QPUYECUOLPXSFR-UHFFFAOYSA-N alpha-methyl-naphthalene Natural products C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
229910000410 antimony oxide Inorganic materials 0.000 description 1
RJAAXVMENUVEAN-UHFFFAOYSA-N antimony vanadium Chemical compound [V].[Sb] RJAAXVMENUVEAN-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical class [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Classifications

- 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
- C07C253/28—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing six-membered aromatic rings, e.g. styrene
- 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
- B01J23/18—Arsenic, antimony or bismuth
- 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
- B01J23/20—Vanadium, niobium or tantalum
- B01J23/22—Vanadium

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)
Catalysts (AREA)

IL24162A 1964-08-17 1965-08-16 Process and catalyst for the production of aromatic nitriles IL24162A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US39020664A	1964-08-17	1964-08-17

Publications (1)

Publication Number	Publication Date
IL24162A true IL24162A (en)	1969-07-30

Family

ID=23541548

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL24162A IL24162A (en)	1964-08-17	1965-08-16	Process and catalyst for the production of aromatic nitriles

Country Status (7)

Country	Link
BE (1)	BE668043A (fr)
CH (1)	CH448989A (fr)
DE (1)	DE1286002B (fr)
ES (1)	ES316568A1 (fr)
GB (1)	GB1114898A (fr)
IL (1)	IL24162A (fr)
LU (1)	LU49318A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE756613A (fr) *	1969-09-26	1971-03-01	Degussa	Catalyseur pour la preparation du dinitrile de l'acide o-phtalique
JPS5390238A (en) *	1977-01-14	1978-08-08	Nippon Kayaku Co Ltd	Preparation of arom. cyano cpds.
JPS56139444A (en)	1980-04-01	1981-10-30	Takeda Chem Ind Ltd	Production of aromatic nitrile
US6413485B2 (en)	1999-05-27	2002-07-02	The Standard Oil Company	Ammoxidation of a mixture of ketones to acetonitrile and HCN
EP2428267A1 (fr) *	2010-09-08	2012-03-14	Leibniz-Institut für Katalyse e.V. an der Universität Rostock	Catalyseur, sa préparation et utilisation pour la préparation de nitriles provenant de composés alkyl-aromatiques ou alkyl-heteroaromatiques

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1071690B (de) *		1959-12-24	The Dis'ftilliens Coimpany Limided, Edinburgh (Großbritannien)	Verfahren zur Herstellung von Nitrilen und bzw. ader Imiiiden von Bienzolcarbonsäuren
US3041363A (en) *	1959-08-14	1962-06-26	Dow Corning	Silethylenesiloxane copolymers
DE1141274B (de) *	1960-08-20	1962-12-20	Bayer Ag	Verfahren zur Herstellung von aromatischen Nitrilen

1965
- 1965-08-04 GB GB33386/65A patent/GB1114898A/en not_active Expired
- 1965-08-09 BE BE668043D patent/BE668043A/xx unknown
- 1965-08-13 LU LU49318D patent/LU49318A1/xx unknown
- 1965-08-16 IL IL24162A patent/IL24162A/en unknown
- 1965-08-16 CH CH1148865A patent/CH448989A/fr unknown
- 1965-08-17 ES ES0316568A patent/ES316568A1/es not_active Expired
- 1965-08-17 DE DEH56900A patent/DE1286002B/de active Pending

Also Published As

Publication number	Publication date
GB1114898A (en)	1968-05-22
BE668043A (fr)	1966-02-09
DE1286002B (de)	1969-01-02
LU49318A1 (fr)	1967-02-13
ES316568A1 (es)	1965-11-16
CH448989A (fr)	1967-12-31

Publication	Publication Date	Title
US5281745A (en)	1994-01-25	Process for producing nitriles
US3954855A (en)	1976-05-04	Process for preparing acrylic acid
JPH0132820B2 (fr)	1989-07-10
JPH02257A (ja)	1990-01-05	ニトリルの製造法
JPS6127097B2 (fr)	1986-06-24
US4124631A (en)	1978-11-07	Process for the production of aromatic nitriles
IL24162A (en)	1969-07-30	Process and catalyst for the production of aromatic nitriles
US3475350A (en)	1969-10-28	Ammoxidation catalyst
US4289656A (en)	1981-09-15	Catalyst for the preparation of ethylenimine
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JPH0832644B2 (ja)	1996-03-29	メタクリル酸および／またはメタクロレインの製造方法
JPH09124580A (ja)	1997-05-13	芳香族またはヘテロ芳香族ニトリルの製造方法、該方法のための担体付き触媒および該触媒の製造方法
US4113768A (en)	1978-09-12	Preparation of acrylic or methacrylic acid from acrolein or methacrolein
CA2010159A1 (fr)	1990-08-21	Cyanation de composes aromatiques halogenes a l'aide de catalyseurs generes in situ a partir de nicl ou de nicl.6h2o
GB1179373A (en)	1970-01-28	Process for Aromatic Substitution
US4146732A (en)	1979-03-27	Process for preparing unsaturated carboxylic acids by the catalytic oxidation in the gas phase of the corresponding aldehydes
JPH0525550B2 (fr)	1993-04-13
US5334743A (en)	1994-08-02	Catalytic ammoxidation of saturated hydrocarbons
US3969390A (en)	1976-07-13	Catalytic process for preparing unsaturated nitriles from olefins, ammonia and oxygen
US4054607A (en)	1977-10-18	Process for preparing anisaldehyde
US3089909A (en)	1963-05-14	Production of unsaturated aliphatic aldehydes
US4082785A (en)	1978-04-04	Manufacture of acrylonitrile from propylene, ammonia and oxygen
JPS60224652A (ja)	1985-11-09	３−メチル−２−ブテン−１−ア−ルの製造方法
US4530797A (en)	1985-07-23	Process for producing polychlorobenzonitrile
US3355479A (en)	1967-11-28	Process for producing aromatic nitriles