CA1066723A - Hydrolyse et hydrogenation en une etape d'acetaldehyde - Google Patents

Hydrolyse et hydrogenation en une etape d'acetaldehyde

Info

Publication number: CA1066723A
Authority: CA; Canada
Prior art keywords: aldehyde; acetal; catalyst; hydro; 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

CA232,675A

Other languages

English (en)

Inventor

Harry B. Copelin

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 CA1066723A publication Critical patent/CA1066723A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 12
230000003301 hydrolyzing effect Effects 0.000 title abstract description 4
239000003054 catalyst Substances 0.000 claims abstract description 25
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 19
239000002253 acid Substances 0.000 claims abstract description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
239000003456 ion exchange resin Substances 0.000 claims abstract description 6
229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 6
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 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000011347 resin Substances 0.000 claims description 11
229920005989 resin Polymers 0.000 claims description 11
239000007868 Raney catalyst Substances 0.000 claims description 6
229910000564 Raney nickel Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 4
-1 acetal aldehyde Chemical class 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 9
150000001875 compounds Chemical class 0.000 abstract description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 9
229920005862 polyol Polymers 0.000 description 8
150000003077 polyols Chemical class 0.000 description 8
239000000203 mixture Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
229910052759 nickel Inorganic materials 0.000 description 5
229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
125000004036 acetal group Chemical group 0.000 description 2
239000010953 base metal Substances 0.000 description 2
230000003197 catalytic effect Effects 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
239000000463 material Substances 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical group CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
SOYANKPFXHJUCE-UHFFFAOYSA-N 1,4-dioxane-2-carbaldehyde Chemical compound O=CC1COCCO1 SOYANKPFXHJUCE-UHFFFAOYSA-N 0.000 description 1
229910000838 Al alloy Inorganic materials 0.000 description 1
FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
101150029512 SCG2 gene Proteins 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
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000007792 addition Methods 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
230000015572 biosynthetic process Effects 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
239000003610 charcoal Substances 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
229910000423 chromium oxide Inorganic materials 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
150000002012 dioxanes Chemical class 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002334 glycols Chemical class 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
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 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
239000007788 liquid Substances 0.000 description 1
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 description 1
239000002609 medium Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000000376 reactant Substances 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
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
125000001424 substituent group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA232,675A 1974-08-02 1975-07-31 Hydrolyse et hydrogenation en une etape d'acetaldehyde Expired CA1066723A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US49429274A	1974-08-02	1974-08-02

Publications (1)

Publication Number	Publication Date
CA1066723A true CA1066723A (fr)	1979-11-20

Family

ID=23963881

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA232,675A Expired CA1066723A (fr)	1974-08-02	1975-07-31	Hydrolyse et hydrogenation en une etape d'acetaldehyde

Country Status (6)

Country	Link
JP (1)	JPS5139614A (fr)
CA (1)	CA1066723A (fr)
DE (1)	DE2523840A1 (fr)
GB (1)	GB1486380A (fr)
IT (1)	IT1040326B (fr)
NL (1)	NL7509217A (fr)

Families Citing this family (2)

* 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

1975
- 1975-05-30 DE DE19752523840 patent/DE2523840A1/de not_active Ceased
- 1975-07-31 GB GB3212375A patent/GB1486380A/en not_active Expired
- 1975-07-31 CA CA232,675A patent/CA1066723A/fr not_active Expired
- 1975-08-01 IT IT2604475A patent/IT1040326B/it active
- 1975-08-01 JP JP9327475A patent/JPS5139614A/ja active Pending
- 1975-08-01 NL NL7509217A patent/NL7509217A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
IT1040326B (it)	1979-12-20
DE2523840A1 (de)	1976-02-12
NL7509217A (nl)	1976-02-04
JPS5139614A (ja)	1976-04-02
GB1486380A (en)	1977-09-21

Publication	Publication Date	Title
US5426249A (en)	1995-06-20	Process for the simultaneous production of 1,2- and 1,3-propanediol
EP0524713B1 (fr)	1996-01-31	Méthode de fabrication du 1,3-propanediol
US5446208A (en)	1995-08-29	Process for producing ether alcohols by hydrogenolysis of cyclic ketal
US5118884A (en)	1992-06-02	Hydrogenation of citral
US4044059A (en)	1977-08-23	One-step method for hydrolyzing and hydrogenating acetal-aldehydes
CA1066723A (fr)	1979-11-20	Hydrolyse et hydrogenation en une etape d'acetaldehyde
US3963754A (en)	1976-06-15	2-Vinyl-5-methyl-1,3-dioxane
KR100344962B1 (ko)	2002-07-20	무수말레인산을 원료로 한 감마 부티로락톤 제조방법
CA1105059A (fr)	1981-07-14	Procede d'obtention de polyols a partir d'acetals cycliques
US5210337A (en)	1993-05-11	Formaldehyde resistant catalyst for hydrogenation and hydrogenolysis of aldehydes, acetals, and esters
CA2194097C (fr)	2005-08-02	Procede de preparation de 1,4-butanediol
US7071362B2 (en)	2006-07-04	Process for producing alicyclic aldehydes
US4105677A (en)	1978-08-08	Production of tetrahydrofuran
CA1066722A (fr)	1979-11-20	Hydrolyse et hydrogenation en deux etapes d'acetaldehydes
US4292452A (en)	1981-09-29	Rhodium-catalyzed hydrogenation of unsaturated aldehydes to unsaturated alcohols
JPH0132214B2 (fr)	1989-06-29
US4105678A (en)	1978-08-08	Synthesis of tetrahydrofuran
CA1049020A (fr)	1979-02-20	Acetaldehydes cycliques
DE69931966T2 (de)	2007-01-04	Herstellung von optisch aktiven alphahydroxyacetalen
US4052401A (en)	1977-10-04	Production of 3-(1',3'-dioxane)-propionaldehyde compounds
US4161616A (en)	1979-07-17	Acrolein conversion to butanediol
US4209651A (en)	1980-06-24	Hydrogenation of butadienepolyperoxide to unsaturated diols
US2429876A (en)	1947-10-28	Catalytic hydrogenation of aminoacetonitrile to ethylene diamine
US4221726A (en)	1980-09-09	Process of making tetrahydrofuran
CA2004040A1 (fr)	1990-06-15	Catalysuer resistant a la formaldehyde pour l'hydrogenation et hydrogenolyse d'aldehydes, d'acetals et d'esters