CA1066722A - Hydrolyse et hydrogenation en deux etapes d'acetaldehydes - Google Patents

Hydrolyse et hydrogenation en deux etapes d'acetaldehydes

Info

Publication number: CA1066722A
Authority: CA; Canada
Prior art keywords: acetal; improvement; hydrogen; hydrogenation; cyclic acetal
Prior art date: 1974-08-02
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

CA232,645A

Other languages

English (en)

Inventor

Colie L. Jenkins (Jr.)

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and 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.)

1974-08-02

Filing date

1975-07-31

Publication date

1979-11-20

1975-07-31 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1979-11-20 Application granted granted Critical

1979-11-20 Publication of CA1066722A publication Critical patent/CA1066722A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 11
230000003301 hydrolyzing effect Effects 0.000 title description 2
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 29
239000003054 catalyst Substances 0.000 claims abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
-1 cyclic acetal Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 7
239000011347 resin Substances 0.000 claims description 7
229920005989 resin Polymers 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 6
229910000564 Raney nickel Inorganic materials 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
239000012736 aqueous medium Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 10
229920005862 polyol Polymers 0.000 abstract description 10
150000003077 polyols Chemical class 0.000 abstract description 10
150000001875 compounds Chemical class 0.000 abstract description 5
239000002253 acid Substances 0.000 abstract description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
239000003456 ion exchange resin Substances 0.000 abstract 1
229920003303 ion-exchange polymer Polymers 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 17
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
150000002500 ions Chemical class 0.000 description 5
239000007868 Raney catalyst Substances 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910045601 alloy Inorganic materials 0.000 description 2
239000000956 alloy Substances 0.000 description 2
239000010953 base metal Substances 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
229940023913 cation exchange resins Drugs 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
150000000185 1,3-diols Chemical class 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000000306 component Substances 0.000 description 1
230000002844 continuous effect Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Natural products CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases

Landscapes

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

CA232,645A 1974-08-02 1975-07-31 Hydrolyse et hydrogenation en deux etapes d'acetaldehydes Expired CA1066722A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US49429174A	1974-08-02	1974-08-02

Publications (1)

Publication Number	Publication Date
CA1066722A true CA1066722A (fr)	1979-11-20

Family

ID=23963875

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA232,645A Expired CA1066722A (fr)	1974-08-02	1975-07-31	Hydrolyse et hydrogenation en deux etapes d'acetaldehydes

Country Status (6)

Country	Link
JP (1)	JPS5139615A (fr)
CA (1)	CA1066722A (fr)
DE (1)	DE2524039A1 (fr)
GB (1)	GB1486379A (fr)
IT (1)	IT1040456B (fr)
NL (1)	NL7509206A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4096192A (en) *	1976-03-30	1978-06-20	E. I. Du Pont De Nemours And Company	Process for the preparation of 2-methyl-1,3-propanediol
GB1581379A (en) *	1976-12-28	1980-12-10	Du Pont	Preparation of diols by hydrogenation and hyrdrolysis of cyclic acetals
JPS5581058A (en) *	1978-12-13	1980-06-18	Ube Ind Ltd	Injection method and device of die-casting machine
BR8004345A (pt) *	1979-09-25	1981-04-28	Nl Industries Inc	Macho desgastavel para ser usado em um molde para fundicao sob pressao e processo para se formar, a partir de metal fundido, uma pecas de fundicao sob pressao com uma regiao rebaixada
US5166370A (en) *	1991-04-12	1992-11-24	Arco Chemical Technology, L.P.	Preparation of tetrahydrofuran using a supported transition metal
JPH06254657A (ja) *	1993-03-04	1994-09-13	Hanano Shoji Kk	シェルモールド用鋳型の成型面処理方法

1975
- 1975-05-30 DE DE19752524039 patent/DE2524039A1/de not_active Withdrawn
- 1975-07-31 CA CA232,645A patent/CA1066722A/fr not_active Expired
- 1975-07-31 GB GB3212275A patent/GB1486379A/en not_active Expired
- 1975-08-01 JP JP9327575A patent/JPS5139615A/ja active Pending
- 1975-08-01 NL NL7509206A patent/NL7509206A/xx not_active Application Discontinuation
- 1975-08-01 IT IT2604375A patent/IT1040456B/it active

Also Published As

Publication number	Publication date
IT1040456B (it)	1979-12-20
NL7509206A (nl)	1976-02-04
GB1486379A (en)	1977-09-21
DE2524039A1 (de)	1976-02-19
JPS5139615A (ja)	1976-04-02

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