CA1099730A - Procede d'obtention de gamma-hydroxytetrahydrofuranes et de tetrahydrofuranes par hydroformylation d'allyl- alcools - Google Patents

Procede d'obtention de gamma-hydroxytetrahydrofuranes et de tetrahydrofuranes par hydroformylation d'allyl- alcools

Info

Publication number: CA1099730A
Authority: CA; Canada
Prior art keywords: gamma; catalyst; preparation; hydroxytetrahydrofuran; tetrahydrofuran
Prior art date: 1975-11-05
Legal status (The legal status 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 status listed.): Expired

Application number

CA264,936A

Other languages

English (en)

Inventor

Jung W. Kang

William L. Hergenrother

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bridgestone Firestone Inc

Original Assignee

Firestone Tire and Rubber 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.)

1975-11-05

Filing date

1976-11-03

Publication date

1981-04-21

1976-11-03 Application filed by Firestone Tire and Rubber Co filed Critical Firestone Tire and Rubber Co

1981-04-21 Application granted granted Critical

1981-04-21 Publication of CA1099730A publication Critical patent/CA1099730A/fr

Status Expired legal-status Critical Current

Links

WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 66
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 title claims abstract description 34
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 33
238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 29
239000003054 catalyst Substances 0.000 claims abstract description 62
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 31
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 13
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 11
229910002091 carbon monoxide Inorganic materials 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical group C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 6
229910019142 PO4 Inorganic materials 0.000 claims description 5
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 5
239000011261 inert gas Substances 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
150000002739 metals Chemical class 0.000 claims description 5
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
KAQHZJVQFBJKCK-UHFFFAOYSA-L potassium pyrosulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OS([O-])(=O)=O KAQHZJVQFBJKCK-UHFFFAOYSA-L 0.000 claims description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
239000010452 phosphate Substances 0.000 claims description 4
-1 phosphite compound Chemical class 0.000 claims description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 3
239000000741 silica gel Substances 0.000 claims description 3
229910002027 silica gel Inorganic materials 0.000 claims description 3
229910001931 tungsten(III) oxide Inorganic materials 0.000 claims description 3
229910052786 argon Inorganic materials 0.000 claims description 2
239000001307 helium Substances 0.000 claims description 2
229910052734 helium Inorganic materials 0.000 claims description 2
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
229910015427 Mo2O3 Inorganic materials 0.000 claims 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
229910052593 corundum Inorganic materials 0.000 claims 1
229910001845 yogo sapphire Inorganic materials 0.000 claims 1
238000006297 dehydration reaction Methods 0.000 abstract description 7
230000018044 dehydration Effects 0.000 abstract description 6
150000001875 compounds Chemical class 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 description 20
239000000047 product Substances 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
150000001336 alkenes Chemical class 0.000 description 4
239000011521 glass Substances 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
239000010948 rhodium Substances 0.000 description 3
JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
150000003284 rhodium compounds Chemical class 0.000 description 2
229910001923 silver oxide Inorganic materials 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
JTMCAHGCWBGWRV-UHFFFAOYSA-N 3-hydroxy-2-methylpropanal Chemical compound OCC(C)C=O JTMCAHGCWBGWRV-UHFFFAOYSA-N 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 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
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
YEJRWHAVMIAJKC-UHFFFAOYSA-N gamma-butyrolactone Natural products O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

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

CA264,936A 1975-11-05 1976-11-03 Procede d'obtention de gamma-hydroxytetrahydrofuranes et de tetrahydrofuranes par hydroformylation d'allyl- alcools Expired CA1099730A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US62916875A	1975-11-05	1975-11-05
US629,168		1975-11-05

Publications (1)

Publication Number	Publication Date
CA1099730A true CA1099730A (fr)	1981-04-21

Family

ID=24521884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA264,936A Expired CA1099730A (fr)	1975-11-05	1976-11-03	Procede d'obtention de gamma-hydroxytetrahydrofuranes et de tetrahydrofuranes par hydroformylation d'allyl- alcools

Country Status (5)

Country	Link
CA (1)	CA1099730A (fr)
DE (1)	DE2649900A1 (fr)
FR (1)	FR2347360A1 (fr)
GB (1)	GB1528697A (fr)
IT (1)	IT1066754B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4091041A (en) *	1977-06-13	1978-05-23	General Electric Company	Preparation of 1,4-diols by hydrolysis-hydrogenation of 2-alkoxytetrahydrofurans
US4123444A (en) *	1977-06-13	1978-10-31	General Electric Company	2-Alkoxy-tetrahydrofurans via hydroformylation of allylic alcohols
DE3308931A1 (de) *	1983-03-12	1984-09-20	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von 3-hydroxytetrahydrofuran
US4529808A (en) *	1984-02-02	1985-07-16	Texaco Inc.	Bi-solvent system for the hydroformylation of allyl alcohol using a rhodium catalyst
US4533742A (en) *	1984-02-02	1985-08-06	Texaco Inc.	Preparation of 2-hydroxytetrahydrofuran by hydroformylation of allyl alcohol using ketone solvents
US5254701A (en) *	1991-05-20	1993-10-19	Eastman Kodak Company	Process for the production of mixtures of 2-hydroxytetrahydrofuran and 4-hydroxybutanal
JP3065430B2 (ja)	1992-06-01	2000-07-17	昭和電工株式会社	アリルアルコールのヒドロホルミル化方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3527809A (en) *	1967-08-03	1970-09-08	Union Carbide Corp	Hydroformylation process
DE2359101A1 (de) *	1972-12-04	1974-06-06	Piero Prof Dr Pino	Verfahren zur asymmetrischen hydroformylierung
DE2410156A1 (de) *	1974-03-02	1975-09-11	Basf Ag	2-aethyl-3-propylbutan-1,4-diol und 2,4-diaethylpentan-1,5-diol enthaltende gemische sowie ein verfahren zu deren herstellung

1976
- 1976-10-29 DE DE19762649900 patent/DE2649900A1/de not_active Withdrawn
- 1976-10-29 IT IT5194776A patent/IT1066754B/it active
- 1976-10-29 FR FR7632804A patent/FR2347360A1/fr active Granted
- 1976-11-03 CA CA264,936A patent/CA1099730A/fr not_active Expired
- 1976-11-05 GB GB4625976A patent/GB1528697A/en not_active Expired

Also Published As

Publication number	Publication date
FR2347360B1 (fr)	1980-06-27
DE2649900A1 (de)	1977-05-12
GB1528697A (en)	1978-10-18
FR2347360A1 (fr)	1977-11-04
IT1066754B (it)	1985-03-12

Legal Events

Date	Code	Title	Description
1998-04-21	MKEX	Expiry

Publication	Publication Date	Title
US4633021A (en)	1986-12-30	Olefin hydroformylation
KR890003749B1 (ko)	1989-10-04	2-에칠헥사놀의 제조방법
US4064145A (en)	1977-12-20	Production of tetrahydrofuran
US4072720A (en)	1978-02-07	Production of alcohol
US3972952A (en)	1976-08-03	Vapor-phase conversion of methanol and ethanol to higher linear primary alcohols by heterogeneous catalysis
US2564104A (en)	1951-08-14	Process for reacting olefinic compounds with carbon monoxide and hydrogen
Neibecker et al.	1989	Synthesis of 2-arylpropionaldehydes through hydroformylation
US4091041A (en)	1978-05-23	Preparation of 1,4-diols by hydrolysis-hydrogenation of 2-alkoxytetrahydrofurans
CA2131337A1 (fr)	1995-03-10	Methode pour l'hydroformylation de buta-1,3-diene
US4258214A (en)	1981-03-24	Process for the production of aldehydes
CA1106857A (fr)	1981-08-11	Procede d'obtention de 3-(4-methyl-3-cyclohexen-1-yl) butyraldehyde
US5945571A (en)	1999-08-31	Preparation of 1,4-butanediol
US4235744A (en)	1980-11-25	Carbonylation of olefinically unsaturated compounds
US4129579A (en)	1978-12-12	Preparation of 2,3-dihydrofuran
HK1000886A1 (en)	2002-03-28	A method for production of 3-formyl-tetrahydrofuran
HK1000886B (en)	2002-03-28	A method for production of 3-formyl-tetrahydrofuran
CA1257878A (fr)	1989-07-25	Methode de preparation de nonadecanediols
CA1157047A (fr)	1983-11-15	Hydroformylation de composes olefiniques
US4105677A (en)	1978-08-08	Production of tetrahydrofuran
KR0134494B1 (ko)	1998-04-20	하이드리도카르보닐트리스(트리오가노포스포러스)로듐의 제조방법
US3975451A (en)	1976-08-17	Diols and process for preparation thereof
US4160771A (en)	1979-07-10	Synthesis of tetrahydrofuran
US4533742A (en)	1985-08-06	Preparation of 2-hydroxytetrahydrofuran by hydroformylation of allyl alcohol using ketone solvents
US4318860A (en)	1982-03-09	Preparation of unsaturated monester precursor for pelargonic acid
CA1309108C (fr)	1992-10-20	Hydroformylation de formaldehyde aqueuse a l'aide d'un systeme de catalyseur rhodium-tricyclohexylphosphine