BE887021A - Procede de production en continu d'alkylbenzaldehydes - Google Patents

Procede de production en continu d'alkylbenzaldehydes Download PDF

Info

Publication number: BE887021A
Authority: BE; Belgium
Prior art keywords: emi; reactor; reaction; xylene; formylation
Prior art date: 1980-01-10

Application number

BE0/203442A

Other languages

English (en)

French (fr)

Original Assignee

Mitsubishi Gas Chemical Co

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.)

1980-01-10

Filing date

1981-01-09

Publication date

1981-05-04

1980-01-10 Priority claimed from JP165280A external-priority patent/JPS5699433A/ja

1980-02-14 Priority claimed from JP1678580A external-priority patent/JPS56113730A/ja

1981-01-09 Application filed by Mitsubishi Gas Chemical Co filed Critical Mitsubishi Gas Chemical Co

1981-05-04 Publication of BE887021A publication Critical patent/BE887021A/fr

Links

238000000034 method Methods 0.000 title claims description 18
230000008569 process Effects 0.000 title description 13
238000010924 continuous production Methods 0.000 title description 4
238000006243 chemical reaction Methods 0.000 claims description 43
229910015900 BF3 Inorganic materials 0.000 claims description 33
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 28
150000004996 alkyl benzenes Chemical class 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 16
150000003738 xylenes Chemical class 0.000 claims description 12
239000008096 xylene Substances 0.000 claims description 11
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims 1
238000006170 formylation reaction Methods 0.000 description 23
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 20
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
230000022244 formylation Effects 0.000 description 18
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 13
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 10
150000001299 aldehydes Chemical class 0.000 description 9
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 9
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 9
239000002994 raw material Substances 0.000 description 9
WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 8
229940078552 o-xylene Drugs 0.000 description 7
GISVICWQYMUPJF-UHFFFAOYSA-N 2,4-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(C)=C1 GISVICWQYMUPJF-UHFFFAOYSA-N 0.000 description 6
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
238000009835 boiling Methods 0.000 description 5
238000007323 disproportionation reaction Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000007086 side reaction Methods 0.000 description 5
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 4
POQJHLBMLVTHAU-UHFFFAOYSA-N 3,4-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1C POQJHLBMLVTHAU-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
239000000945 filler Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
150000003934 aromatic aldehydes Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
238000004064 recycling Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
239000001431 2-methylbenzaldehyde Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
-1 paratolualdehyde Chemical class 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 description 1
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
SMUVABOERCFKRW-UHFFFAOYSA-N 2,5-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C)C(C=O)=C1 SMUVABOERCFKRW-UHFFFAOYSA-N 0.000 description 1
NTWBHJYRDKBGBR-UHFFFAOYSA-N 2-ethylbenzaldehyde Chemical compound CCC1=CC=CC=C1C=O NTWBHJYRDKBGBR-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241001292274 Eumenes Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
MOWNZPNSYMGTMD-UHFFFAOYSA-N boron monoxide Inorganic materials O=[B] MOWNZPNSYMGTMD-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000008016 vaporization Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE0/203442A 1980-01-10 1981-01-09 Procede de production en continu d'alkylbenzaldehydes BE887021A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP165280A JPS5699433A (en)	1980-01-10	1980-01-10	Continuous preparation of alkylbenzaldehyde
JP1678580A JPS56113730A (en)	1980-02-14	1980-02-14	Formylation of xylene mixture

Publications (1)

Publication Number	Publication Date
BE887021A true BE887021A (fr)	1981-05-04

Family

ID=26334925

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/203442A BE887021A (fr)	1980-01-10	1981-01-09	Procede de production en continu d'alkylbenzaldehydes

Country Status (2)

Country	Link
BE (1)	BE887021A (it)
IT (1)	IT1144303B (it)

1981
- 1981-01-09 BE BE0/203442A patent/BE887021A/fr not_active IP Right Cessation
- 1981-01-09 IT IT67016/81A patent/IT1144303B/it active

Also Published As

Publication number	Publication date
IT8167016A0 (it)	1981-01-09
IT1144303B (it)	1986-10-29

Legal Events

Date

Code

Title

Description

2000-07-31

RE

Patent lapsed

Owner name: MITSUBISHI GAS CHEMICAL CY INC.

Effective date: 20000131

Publication	Publication Date	Title
FR2501673A1 (fr)	1982-09-17	Procede continu de production d'acide terephtalique
FR2710638A1 (fr)	1995-04-07	Procédé de préparation d'isomères d'acides benzènedicarboxyliques de haute pureté.
US4460794A (en)	1984-07-17	Process for continuous production of alkylbenzaldehydes
FR3104571A1 (fr)	2021-06-18	Dispositif et procédé de conversion de composés aromatiques par alkylation de toluène par du CO pour production de paratolualdéhyde
FR2463116A1 (fr)	1981-02-20	Procede pour la production d'un acide polycarboxylique aromatique comportant au moins trois radicaux carboxyle
EP0648731B1 (fr)	1998-01-07	Procédé d'hydroxycarbonylation du butadiène
BE887021A (fr)	1981-05-04	Procede de production en continu d'alkylbenzaldehydes
EP0478428B1 (fr)	1995-03-08	Procédé de préparation d'oxyde borique par hydrolyse du borate de méthyle et sa mise en oeuvre dans l'oxydation d'hydrocarbures saturées en alcools
FR2682103A1 (fr)	1993-04-09	Procede de debromation de derives dibromes du naphtol.
FR2795410A1 (fr)	2000-12-29	Procede pour ameliorer la stabilite et/ou eviter la desactivation du catalyseur lors de la fabrication d'acide acetique et/ou d'acetate de methyle
EP0667331A1 (fr)	1995-08-16	Procédé de préparation d'hydroxybenzaldehydes
WO2002046096A1 (fr)	2002-06-13	Procede de fabrication d'hydrazine en solution aqueuse
FR2604998A1 (fr)	1988-04-15	Procede de preparation d'un melange renfermant du cyclohexanol et de la cyclohexanone a partir du cyclohexane
EP0889871B1 (fr)	2001-10-31	Procede de preparation d'acide acetique et/ou d'acetate de methyle par isomerisation et carbonylation
FR2470761A1 (fr)	1981-06-12	Procede de preparation de l'acide trimellitique
FR3104572A1 (fr)	2021-06-18	Conversion de composés aromatiques par alkylation de toluène par du CO et de benzène par l’éthanol pour production de paratolualdéhyde
US3187038A (en)	1965-06-01	Continuous oxidation process for production of benzoic acid
BE853377A (fr)	1977-10-07	Procede de preparation continue d'aldehydes par hydroformylation
EP0000302B1 (fr)	1980-10-01	Nouveau procédé de préparation de la quinidine.
EP0552325B1 (fr)	1995-04-26	Compose naphtalenique nouveau et procede pour son obtention
US3281459A (en)	1966-10-25	Preparation of aromatic polycarboxylic acids from 2, 2-ditolyl-alkanes
CH637104A5 (fr)	1983-07-15	Procede de synthese de dinitro-2,4 t-butyl-6 methyl-3 anisole.
CH341486A (fr)	1959-10-15	Procédé de préparation d'un acide monocarboxylique aromatique
BE529997A (it)
FR3104573A1 (fr)	2021-06-18	Dispositif et procédé de conversion de composés aromatiques par alkylation de toluène par du méthanol