NL9401708A - Werkwijze voor de bereiding van 3-fenylpropanal. - Google Patents

Werkwijze voor de bereiding van 3-fenylpropanal. Download PDF

Info

Publication number: NL9401708A
Authority: NL; Netherlands
Prior art keywords: phenylpropanal; cinnamaldehyde; preparation; oxidation; carried out
Prior art date: 1994-10-17

Application number

NL9401708A

Other languages

English (en)

Dutch (nl)

Inventor

Anna Maria Cornelia Castelijns

Johanna Margreet Hogeweg

Simon Petrus Johannes M Nispen

Original Assignee

Dsm 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.)

1994-10-17

Filing date

1994-10-17

Publication date

1996-06-03

1994-10-17 Application filed by Dsm Nv filed Critical Dsm Nv

1994-10-17 Priority to NL9401708A priority Critical patent/NL9401708A/nl

1995-10-17 Priority to ES95935615T priority patent/ES2133817T3/es

1995-10-17 Priority to DE69509800T priority patent/DE69509800T2/de

1995-10-17 Priority to DK95935615T priority patent/DK0804401T3/da

1995-10-17 Priority to PCT/NL1995/000359 priority patent/WO1996011898A1/en

1995-10-17 Priority to EP95935615A priority patent/EP0804401B1/en

1995-10-17 Priority to JP51312396A priority patent/JP3895372B2/ja

1995-10-17 Priority to AT95935615T priority patent/ATE180245T1/de

1996-06-03 Publication of NL9401708A publication Critical patent/NL9401708A/nl

1997-04-16 Priority to US08/834,456 priority patent/US5811588A/en

Links

YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 title claims abstract description 40
238000000034 method Methods 0.000 title claims abstract description 39
238000002360 preparation method Methods 0.000 title claims abstract description 15
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims abstract description 36
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims abstract description 20
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims abstract description 20
229940117916 cinnamic aldehyde Drugs 0.000 claims abstract description 20
238000007254 oxidation reaction Methods 0.000 claims abstract description 19
230000003647 oxidation Effects 0.000 claims abstract description 18
239000003054 catalyst Substances 0.000 claims abstract description 17
238000006243 chemical reaction Methods 0.000 claims abstract description 14
239000011541 reaction mixture Substances 0.000 claims abstract description 11
239000004030 hiv protease inhibitor Substances 0.000 claims abstract description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
239000003814 drug Substances 0.000 claims abstract description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 19
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
235000011056 potassium acetate Nutrition 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
229910001882 dioxygen Inorganic materials 0.000 claims description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
229940122440 HIV protease inhibitor Drugs 0.000 claims 3
229910052783 alkali metal Inorganic materials 0.000 claims 3
-1 alkali metal salt Chemical class 0.000 claims 3
230000002378 acidificating effect Effects 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 2
230000000840 anti-viral effect Effects 0.000 abstract 1
239000003153 chemical reaction reagent Substances 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 description 12
VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
229930016911 cinnamic acid Natural products 0.000 description 3
235000013985 cinnamic acid Nutrition 0.000 description 3
229910052593 corundum Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910001845 yogo sapphire Inorganic materials 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
241000723347 Cinnamomum Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
235000017803 cinnamon Nutrition 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
239000001496 (E)-2-methyl-3-phenylprop-2-enal Substances 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 1
101150116295 CAT2 gene Proteins 0.000 description 1
101100326920 Caenorhabditis elegans ctl-1 gene Proteins 0.000 description 1
101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 1
101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 1
101100005280 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-3 gene Proteins 0.000 description 1
101100126846 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) katG gene Proteins 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000002871 cinnamic aldehydes group Chemical group 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000007787 solid Substances 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Compounds Of Unknown Constitution (AREA)
Inorganic Fibers (AREA)
Glass Compositions (AREA)

NL9401708A 1994-10-17 1994-10-17 Werkwijze voor de bereiding van 3-fenylpropanal. NL9401708A (nl)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
NL9401708A NL9401708A (nl)	1994-10-17	1994-10-17	Werkwijze voor de bereiding van 3-fenylpropanal.
ES95935615T ES2133817T3 (es)	1994-10-17	1995-10-17	Procedimiento para la preparacion de 3-fenil-propanal.
DE69509800T DE69509800T2 (de)	1994-10-17	1995-10-17	Verfahren zur herstellung von propionaldehyd
DK95935615T DK0804401T3 (da)	1994-10-17	1995-10-17	Fremgangsmåde til fremstilling af 3-phenylpropanal
PCT/NL1995/000359 WO1996011898A1 (en)	1994-10-17	1995-10-17	Process for the preparation of 3-phenylpropanal
EP95935615A EP0804401B1 (en)	1994-10-17	1995-10-17	Process for the preparation of 3-phenylpropanal
JP51312396A JP3895372B2 (ja)	1994-10-17	1995-10-17	３−フェニルプロピオンアルデヒドの製造方法
AT95935615T ATE180245T1 (de)	1994-10-17	1995-10-17	Verfahren zur herstellung von propionaldehyd
US08/834,456 US5811588A (en)	1994-10-17	1997-04-16	Process for the preparation of 3-phenylpropanal

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL9401708A NL9401708A (nl)	1994-10-17	1994-10-17	Werkwijze voor de bereiding van 3-fenylpropanal.
NL9401708		1994-10-17

Publications (1)

Publication Number	Publication Date
NL9401708A true NL9401708A (nl)	1996-06-03

Family

ID=19864784

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9401708A NL9401708A (nl)	1994-10-17	1994-10-17	Werkwijze voor de bereiding van 3-fenylpropanal.

Country Status (9)

Country	Link
US (1)	US5811588A (da)
EP (1)	EP0804401B1 (da)
JP (1)	JP3895372B2 (da)
AT (1)	ATE180245T1 (da)
DE (1)	DE69509800T2 (da)
DK (1)	DK0804401T3 (da)
ES (1)	ES2133817T3 (da)
NL (1)	NL9401708A (da)
WO (1)	WO1996011898A1 (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5939581A (en) *	1997-08-20	1999-08-17	First Chemical Corporation	Processes for preparing hydrocinnamic acid
DE19949672A1 (de) *	1999-10-14	2001-04-19	Basf Ag	Kontinuierliches Verfahren zur Herstellung von Zimtaldehydderivaten
US6229187B1 (en)	1999-10-20	2001-05-08	Advanced Micro Devices, Inc.	Field effect transistor with non-floating body and method for forming same on a bulk silicon wafer
DE60140250D1 (de) *	2000-05-16	2009-12-03	Ajinomoto Kk	Verfahren zur herstellung von cinnamylaldehyd-derivaten und ihre verwendung
US6566557B2 (en)	2001-03-14	2003-05-20	Council Of Scientific And Industrial Research	Process for the preparation of substituted trans-cinnamaldehyde, a natural yellow dye, from phenylpropane derivatives
GB0112093D0 (en) *	2001-05-18	2001-07-11	Univ Belfast	Hydrogenation processes
DE102016116347A1 (de)	2016-09-01	2018-03-01	Leibniz-Institut Für Katalyse E.V. An Der Universität Rostock	Verfahren zur gleichzeitigen und kontinuierlichen herstellung von cyclohexanon und hydrozimtaldehyd aus cyclohexanol und zimtaldehyd
WO2026009596A1 (ja) *	2024-07-05	2026-01-08	三菱瓦斯化学株式会社	アルデヒドの製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB955421A (en) *	1960-02-04	1964-04-15	Ici Ltd	Improvements in and relating to the oxidation of aldehydes
DE2030031A1 (en) *	1968-07-15	1971-12-23		Hydrogenation of cinnamaldehyde to give - increased yields of dihydrocinnamaldehyde

1994
- 1994-10-17 NL NL9401708A patent/NL9401708A/nl not_active Application Discontinuation
1995
- 1995-10-17 EP EP95935615A patent/EP0804401B1/en not_active Expired - Lifetime
- 1995-10-17 ES ES95935615T patent/ES2133817T3/es not_active Expired - Lifetime
- 1995-10-17 AT AT95935615T patent/ATE180245T1/de not_active IP Right Cessation
- 1995-10-17 DE DE69509800T patent/DE69509800T2/de not_active Expired - Lifetime
- 1995-10-17 DK DK95935615T patent/DK0804401T3/da active
- 1995-10-17 WO PCT/NL1995/000359 patent/WO1996011898A1/en not_active Ceased
- 1995-10-17 JP JP51312396A patent/JP3895372B2/ja not_active Expired - Fee Related
1997
- 1997-04-16 US US08/834,456 patent/US5811588A/en not_active Expired - Lifetime

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB955421A (en) *	1960-02-04	1964-04-15	Ici Ltd	Improvements in and relating to the oxidation of aldehydes
DE2030031A1 (en) *	1968-07-15	1971-12-23		Hydrogenation of cinnamaldehyde to give - increased yields of dihydrocinnamaldehyde

Also Published As

Publication number	Publication date
JP3895372B2 (ja)	2007-03-22
DE69509800T2 (de)	2000-01-13
EP0804401B1 (en)	1999-05-19
DE69509800D1 (de)	1999-06-24
DK0804401T3 (da)	1999-11-22
ES2133817T3 (es)	1999-09-16
WO1996011898A1 (en)	1996-04-25
US5811588A (en)	1998-09-22
JPH10508008A (ja)	1998-08-04
ATE180245T1 (de)	1999-06-15
EP0804401A1 (en)	1997-11-05

Legal Events

Date	Code	Title	Description
1996-06-03	A1B	A search report has been drawn up
1996-12-02	BV	The patent application has lapsed

Publication	Publication Date	Title
US4933507A (en)	1990-06-12	Method of dehydrogenating cyclohexenone
WO2000048972A1 (en)	2000-08-24	Oxidation method
JP2003525920A (ja)	2003-09-02	アルデヒドから脂肪族カルボン酸を製造する方法
Guertin et al.	1993	Chemoselective catalytic oxidation of sulfides to sulfones with tetrapropylammonium perruthenate (TPAP)
Brégeault et al.	2001	Catalytic oxidative carbon carbon bond cleavage of ketones with dioxygen: assessment of some metal complexes. Some alternatives for preparing α, ω-dicarboxylic acids
EP0512656B1 (en)	1996-04-10	Process for the preparation of vinyl derivatives
EP0804401B1 (en)	1999-05-19	Process for the preparation of 3-phenylpropanal
CA1162566A (en)	1984-02-21	Processes for producing 7-octen-1-al and derivatives thereof
JP2003525919A (ja)	2003-09-02	アルデヒドから直鎖状脂肪族カルボン酸を製造する方法
JP3059695B2 (ja)	2000-07-04	シクロヘキサン酸化生成物の洗浄水から二酸を製造する方法
US5003102A (en)	1991-03-26	Preparation of 5-formylvaleric esters
HU222573B1 (hu)	2003-08-28	Eljárás mono- vagy dikarbonsavak előállítására aldehidekből, ezek acetáljaiból vagy félacetáljaiból, továbbá ezek keverékéből
NL9401707A (nl)	1996-06-03	Werkwijze voor de bereiding van 3-fenylpropaanzuur.
EP1165479B1 (en)	2003-10-01	Preparation of carvone
JP5055262B2 (ja)	2012-10-24	水中におけるｐ−キシレンの液相酸化によるｐ−トルイル酸の製造方法
JPH0830026B2 (ja)	1996-03-27	グリオキシル酸類の製造法
Hara et al.	2002	A novel production of γ-butyrolactone catalyzed by homogeneous ruthenium complexes
JPS5926611B2 (ja)	1984-06-29	無水酢酸の製造方法
US5939581A (en)	1999-08-17	Processes for preparing hydrocinnamic acid
JP4297307B2 (ja)	2009-07-15	１−インダノン類の製造方法
JPH11511176A (ja)	1999-09-28	１，４−ブテンジオールの製造方法
JPH0510976B2 (da)	1993-02-12
JPH06157416A (ja)	1994-06-03	グリオキシル酸エステルの製造方法
JPS5929170B2 (ja)	1984-07-18	β−フエニルエチルアルコ−ルおよび酢酸β−フエニルエチルの製造方法
JPH1149710A (ja)	1999-02-23	トリメチルハイドロキノン類の製造法