CS219286B4 - Method of making the nitrosobenzene - Google Patents

Method of making the nitrosobenzene Download PDF

Info

Publication number: CS219286B4
Authority: CS; Czechoslovakia
Prior art keywords: nitrobenzene; water; nitrosobenzene; catalyst; carbon atoms
Prior art date: 1979-08-17

Application number

CS805015A

Other languages

Czech (cs)

English (en)

Inventor

Hans Zengel

Manfred Bergfeld

Werner Klostermeier

Original Assignee

Akzo Nv

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.)

1979-08-17

Filing date

1980-07-15

Publication date

1983-03-25

1980-07-15 Application filed by Akzo Nv filed Critical Akzo Nv

1983-03-25 Publication of CS219286B4 publication Critical patent/CS219286B4/cs

Links

NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 title claims abstract description 18
238000004519 manufacturing process Methods 0.000 title claims description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 72
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 24
239000003638 chemical reducing agent Substances 0.000 claims abstract description 10
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
239000003054 catalyst Substances 0.000 claims description 35
229930195733 hydrocarbon Natural products 0.000 claims description 16
150000002430 hydrocarbons Chemical class 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
239000004215 Carbon black (E152) Substances 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 6
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 6
-1 ethylene, propylene Chemical group 0.000 claims description 4
239000011261 inert gas Substances 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
239000001569 carbon dioxide Substances 0.000 claims description 3
229910052756 noble gas Inorganic materials 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 3
238000002360 preparation method Methods 0.000 abstract description 2
150000007824 aliphatic compounds Chemical class 0.000 abstract 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
239000007789 gas Substances 0.000 description 7
239000011572 manganese Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000009257 reactivity Effects 0.000 description 6
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 4
GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 4
238000002407 reforming Methods 0.000 description 4
230000000052 comparative effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
229910052748 manganese Inorganic materials 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000011324 bead Substances 0.000 description 2
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
229910000464 lead oxide Inorganic materials 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
229910052774 Proactinium Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005485 electric heating Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229910052745 lead Inorganic materials 0.000 description 1
RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 description 1
WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical group [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000002835 noble gases Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
239000010959 steel Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS805015A 1979-08-17 1980-07-15 Method of making the nitrosobenzene CS219286B4 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2933314A DE2933314C2 (de)	1979-08-17	1979-08-17	Verfahren zur Herstellung von Nitrosobenzol

Publications (1)

Publication Number	Publication Date
CS219286B4 true CS219286B4 (en)	1983-03-25

Family

ID=6078655

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS805015A CS219286B4 (en)	1979-08-17	1980-07-15	Method of making the nitrosobenzene

Country Status (15)

Country	Link
US (1)	US4314089A (it)
JP (1)	JPS5630951A (it)
BE (1)	BE884662R (it)
BR (1)	BR8005079A (it)
CA (1)	CA1132614A (it)
CS (1)	CS219286B4 (it)
DD (1)	DD152541A6 (it)
DE (1)	DE2933314C2 (it)
ES (1)	ES8104984A2 (it)
FR (1)	FR2463764A2 (it)
GB (1)	GB2056453B (it)
IT (1)	IT1145699B (it)
NL (1)	NL8004281A (it)
PL (1)	PL124384B3 (it)
RO (1)	RO79970A7 (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6039769A (ja) *	1983-08-12	1985-03-01	Matsushita Electric Ind Co Ltd	構成電池

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3504035A (en) *	1966-07-01	1970-03-31	American Cyanamid Co	Process for preparing aromatic amines from aromatic nitro compounds
GB1203698A (en) *	1967-11-24	1970-09-03	Ici Ltd	Process for the reduction of aromatic nitro compounds
GB1396936A (en) *	1972-09-14	1975-06-11	Ici Ltd	Reduction process
DE2713602C3 (de) *	1977-03-28	1980-03-20	Akzo Gmbh, 5600 Wuppertal	Verfahren zur Herstellung von Nitrosobenzol

1979
- 1979-08-17 DE DE2933314A patent/DE2933314C2/de not_active Expired
1980
- 1980-03-13 US US06/129,959 patent/US4314089A/en not_active Expired - Lifetime
- 1980-03-18 CA CA348,914A patent/CA1132614A/en not_active Expired
- 1980-07-12 RO RO80101676A patent/RO79970A7/ro unknown
- 1980-07-15 CS CS805015A patent/CS219286B4/cs unknown
- 1980-07-25 NL NL8004281A patent/NL8004281A/nl not_active Application Discontinuation
- 1980-07-28 FR FR8016579A patent/FR2463764A2/fr active Granted
- 1980-08-07 BE BE0/201668A patent/BE884662R/fr active
- 1980-08-11 IT IT49462/80A patent/IT1145699B/it active
- 1980-08-13 BR BR8005079A patent/BR8005079A/pt unknown
- 1980-08-13 DD DD80223306A patent/DD152541A6/de unknown
- 1980-08-14 ES ES494254A patent/ES8104984A2/es not_active Expired
- 1980-08-14 GB GB8026496A patent/GB2056453B/en not_active Expired
- 1980-08-16 PL PL1980226287A patent/PL124384B3/pl unknown
- 1980-08-18 JP JP11276780A patent/JPS5630951A/ja active Granted

Also Published As

Publication number	Publication date
BR8005079A (pt)	1981-02-24
RO79970A7 (ro)	1983-02-01
US4314089A (en)	1982-02-02
DD152541A6 (de)	1981-12-02
GB2056453A (en)	1981-03-18
CA1132614A (en)	1982-09-28
JPS5630951A (en)	1981-03-28
FR2463764A2 (fr)	1981-02-27
PL124384B3 (en)	1983-01-31
RO79970B1 (ro)	1983-01-30
NL8004281A (nl)	1981-02-19
DE2933314A1 (de)	1981-03-26
IT1145699B (it)	1986-11-05
ES494254A0 (es)	1981-04-01
PL226287A3 (it)	1981-03-27
DE2933314C2 (de)	1985-11-07
IT8049462A0 (it)	1980-08-11
GB2056453B (en)	1983-06-08
JPH0215528B2 (it)	1990-04-12
BE884662R (fr)	1980-12-01
FR2463764B2 (it)	1984-04-20
ES8104984A2 (es)	1981-04-01

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US4001260A (en)	1977-01-04	Synthesis of aromatic amines by reaction of aromatic compounds with ammonia
US3164627A (en)	1965-01-05	Method for preparing unsaturated aliphatic nitriles
US4178315A (en)	1979-12-11	Process for the preparation of nitrosobenzene
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US3278575A (en)	1966-10-11	Method for the manufacture of aliphatic nitriles
US3424781A (en)	1969-01-28	Production of unsaturated aliphatic nitriles
US2496659A (en)	1950-02-07	Production of nitriles
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US3923891A (en)	1975-12-02	Hydrogenation of benzonitrile to dibenzylamine
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US4216169A (en)	1980-08-05	Two-stage catalytic hydrogenation of olefinically unsaturated dinitriles
US4801751A (en)	1989-01-31	Process for the disproportionation of alkylated aromatic primary amines
US3718707A (en)	1973-02-27	Oxidative dehydrogenation
US2450641A (en)	1948-10-05	Production of nitriles
US2463466A (en)	1949-03-01	Production of nitriles
CA1154460A (en)	1983-09-27	Process for the preparation of nitrosobenzene