NL8701063A - Werkwijze voor de bereiding van benzaldehyde in de gasfase. - Google Patents

Werkwijze voor de bereiding van benzaldehyde in de gasfase. Download PDF

Info

Publication number: NL8701063A
Authority: NL; Netherlands
Prior art keywords: catalyst; manganese; process according; benzoic acid; preparation
Prior art date: 1987-05-06

Application number

NL8701063A

Other languages

English (en)

Dutch (nl)

Original Assignee

Stamicarbon

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.)

1987-05-06

Filing date

1987-05-06

Publication date

1988-12-01

1987-05-06 Application filed by Stamicarbon filed Critical Stamicarbon

1987-05-06 Priority to NL8701063A priority Critical patent/NL8701063A/nl

1988-05-03 Priority to DE8888200860T priority patent/DE3862420D1/de

1988-05-03 Priority to ES88200860T priority patent/ES2022594B3/es

1988-05-03 Priority to AT88200860T priority patent/ATE62654T1/de

1988-05-03 Priority to EP88200860A priority patent/EP0290096B1/de

1988-05-04 Priority to CA000565862A priority patent/CA1308119C/en

1988-05-06 Priority to JP63109245A priority patent/JPS6445330A/ja

1988-05-06 Priority to US07/191,053 priority patent/US4987265A/en

1988-12-01 Publication of NL8701063A publication Critical patent/NL8701063A/nl

1991-07-11 Priority to GR91400994T priority patent/GR3002297T3/el

Links

238000002360 preparation method Methods 0.000 title claims abstract description 25
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title claims abstract description 24
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 title claims abstract description 12
238000000034 method Methods 0.000 title claims description 19
239000003054 catalyst Substances 0.000 claims abstract description 66
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 46
239000005711 Benzoic acid Substances 0.000 claims abstract description 23
235000010233 benzoic acid Nutrition 0.000 claims abstract description 23
239000011572 manganese Substances 0.000 claims abstract description 23
229910052748 manganese Inorganic materials 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
238000000975 co-precipitation Methods 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 12
239000007789 gas Substances 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims abstract description 8
150000002696 manganese Chemical class 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 5
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 4
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052782 aluminium Inorganic materials 0.000 claims abstract description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052735 hafnium Inorganic materials 0.000 claims abstract description 4
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052758 niobium Inorganic materials 0.000 claims abstract description 4
239000010955 niobium Substances 0.000 claims abstract description 4
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims abstract description 4
239000010936 titanium Substances 0.000 claims abstract description 4
229910052719 titanium Inorganic materials 0.000 claims abstract description 4
229910052726 zirconium Inorganic materials 0.000 claims abstract description 4
238000001354 calcination Methods 0.000 claims abstract description 3
230000002378 acidificating effect Effects 0.000 claims description 8
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
229910002651 NO3 Inorganic materials 0.000 claims description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 claims description 4
229910052684 Cerium Inorganic materials 0.000 claims description 3
150000003935 benzaldehydes Chemical class 0.000 claims description 3
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 3
SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical group CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 claims description 2
238000010574 gas phase reaction Methods 0.000 claims description 2
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical group COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims 2
239000004411 aluminium Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 24
239000000243 solution Substances 0.000 description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
VEVJTUNLALKRNO-TYHXJLICSA-N benzoyl-CoA Chemical compound O=C([C@H](O)C(C)(COP(O)(=O)OP(O)(=O)OC[C@@H]1[C@H]([C@@H](O)[C@@H](O1)N1C2=NC=NC(N)=C2N=C1)OP(O)(O)=O)C)NCCC(=O)NCCSC(=O)C1=CC=CC=C1 VEVJTUNLALKRNO-TYHXJLICSA-N 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001721 carbon Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 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
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000004898 kneading Methods 0.000 description 1
DSGIMNDXYTYOBX-UHFFFAOYSA-N manganese zirconium Chemical compound [Mn].[Zr] DSGIMNDXYTYOBX-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc 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
- B01J23/32—Manganese, technetium or rhenium
- B01J23/34—Manganese
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- 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
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof

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)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8701063A 1987-05-06 1987-05-06 Werkwijze voor de bereiding van benzaldehyde in de gasfase. NL8701063A (nl)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
NL8701063A NL8701063A (nl)	1987-05-06	1987-05-06	Werkwijze voor de bereiding van benzaldehyde in de gasfase.
DE8888200860T DE3862420D1 (de)	1987-05-06	1988-05-03	Verfahren zur herstellung von benzaldehyd in der gasphase.
ES88200860T ES2022594B3 (es)	1987-05-06	1988-05-03	Proceso para la preparacion de benzaldehido en fase gaseosa.
AT88200860T ATE62654T1 (de)	1987-05-06	1988-05-03	Verfahren zur herstellung von benzaldehyd in der gasphase.
EP88200860A EP0290096B1 (de)	1987-05-06	1988-05-03	Verfahren zur Herstellung von Benzaldehyd in der Gasphase
CA000565862A CA1308119C (en)	1987-05-06	1988-05-04	Process for the preparation of benzaldehyde in the gas phase
JP63109245A JPS6445330A (en)	1987-05-06	1988-05-06	Manufacture of benzaldehyde in gas phase
US07/191,053 US4987265A (en)	1987-05-06	1988-05-06	Process for the preparation of benzaldehyde in the gas phase
GR91400994T GR3002297T3 (en)	1987-05-06	1991-07-11	Process for the preparation of benzaldehyde in the gas phase

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8701063A NL8701063A (nl)	1987-05-06	1987-05-06	Werkwijze voor de bereiding van benzaldehyde in de gasfase.
NL8701063		1987-05-06

Publications (1)

Publication Number	Publication Date
NL8701063A true NL8701063A (nl)	1988-12-01

Family

ID=19849960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8701063A NL8701063A (nl)	1987-05-06	1987-05-06	Werkwijze voor de bereiding van benzaldehyde in de gasfase.

Country Status (9)

Country	Link
US (1)	US4987265A (de)
EP (1)	EP0290096B1 (de)
JP (1)	JPS6445330A (de)
AT (1)	ATE62654T1 (de)
CA (1)	CA1308119C (de)
DE (1)	DE3862420D1 (de)
ES (1)	ES2022594B3 (de)
GR (1)	GR3002297T3 (de)
NL (1)	NL8701063A (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3927786A1 (de) *	1989-08-23	1991-02-28	Bayer Ag	Verfahren zur herstellung von aldehyden
NL9200817A (nl) *	1992-05-07	1993-12-01	Dsm Nv	Omzetting van cycloalkanon in lacton.
DE4443704A1 (de)	1994-12-08	1996-06-13	Basf Ag	Verfahren zur Herstellung von Aldehyden
DE19509552A1 (de) *	1995-03-16	1996-09-19	Basf Ag	Verfahren zur Herstellung von 5- oder 6-gliedrigen, Stickstoff enthaltenden heterocyclischen Aldehyden
CN103204767B (zh) *	2013-04-25	2015-12-09	江苏理工学院	苯甲酸气相催化加氢制备无氯苯甲醛的方法
CN112473719B (zh) *	2021-01-25	2021-06-29	潍坊科技学院	一种多孔碳氮材料负载纳米双金属催化剂的制备方法及其在苯甲酸加氢反应中的使用方法
CN115715986B (zh) *	2022-11-02	2024-01-30	浙江大洋生物科技集团股份有限公司	一种低温常压甲苯催化氧化生成苯甲醛的催化剂制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4075251A (en) *	1975-07-17	1978-02-21	Exxon Research & Engineering Co.	Hydrogenation of organic compounds
DE3361923D1 (en) *	1982-08-09	1986-03-06	Shell Int Research	Process and catalytic composition for the preparation of aldehydes, and aldehydes thus prepared
EP0150961B1 (de) *	1984-01-18	1988-05-11	Mitsubishi Kasei Corporation	Katalytisches Verfahren zur Herstellung aromatischer Aldehyde
JPS60152434A (ja) *	1984-01-18	1985-08-10	Mitsubishi Chem Ind Ltd	芳香族アルデヒド類の製造方法
US4585899A (en) *	1985-01-22	1986-04-29	Chem Systems Inc.	Hydrogenation of carboxylic acid compounds to aldehydes using MnO2 on gamma alumina as catalyst
JPH0738944B2 (ja) *	1985-07-17	1995-05-01	三菱化学株式会社	カルボン酸の還元用触媒

1987
- 1987-05-06 NL NL8701063A patent/NL8701063A/nl not_active Application Discontinuation
1988
- 1988-05-03 DE DE8888200860T patent/DE3862420D1/de not_active Expired - Lifetime
- 1988-05-03 ES ES88200860T patent/ES2022594B3/es not_active Expired - Lifetime
- 1988-05-03 EP EP88200860A patent/EP0290096B1/de not_active Expired - Lifetime
- 1988-05-03 AT AT88200860T patent/ATE62654T1/de not_active IP Right Cessation
- 1988-05-04 CA CA000565862A patent/CA1308119C/en not_active Expired - Lifetime
- 1988-05-06 US US07/191,053 patent/US4987265A/en not_active Expired - Fee Related
- 1988-05-06 JP JP63109245A patent/JPS6445330A/ja active Pending
1991
- 1991-07-11 GR GR91400994T patent/GR3002297T3/el unknown

Also Published As

Publication number	Publication date
ES2022594B3 (es)	1991-12-01
US4987265A (en)	1991-01-22
JPS6445330A (en)	1989-02-17
GR3002297T3 (en)	1992-12-30
ATE62654T1 (de)	1991-05-15
EP0290096B1 (de)	1991-04-17
DE3862420D1 (de)	1991-05-23
EP0290096A1 (de)	1988-11-09
CA1308119C (en)	1992-09-29

Legal Events

Date	Code	Title	Description
1988-12-01	A1B	A search report has been drawn up
1990-01-02	BV	The patent application has lapsed

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