CA1047526A - Acetoxy-4 butyraldehyde et acetoxy-4 butanol - Google Patents

Acetoxy-4 butyraldehyde et acetoxy-4 butanol

Info

Publication number: CA1047526A
Authority: CA; Canada
Prior art keywords: reaction; acetoxybutyraldehyde; hydroformylation; mixture; cobalt
Prior art date: 1974-09-16
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

CA209,307A

Other languages

English (en)

Inventor

William E. Smith

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.)

General Electric Co

Original Assignee

General Electric 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.)

1974-09-16

Filing date

1974-09-16

Publication date

1979-01-30

1974-09-16 Application filed by General Electric Co filed Critical General Electric Co

1974-09-16 Priority to CA209,307A priority Critical patent/CA1047526A/fr

1979-01-30 Application granted granted Critical

1979-01-30 Publication of CA1047526A publication Critical patent/CA1047526A/fr

Status Expired legal-status Critical Current

Links

OZTUJRSHRYXRFW-UHFFFAOYSA-N 4-oxobutyl acetate Chemical compound CC(=O)OCCCC=O OZTUJRSHRYXRFW-UHFFFAOYSA-N 0.000 title claims abstract description 33
238000000034 method Methods 0.000 title claims description 25
230000008569 process Effects 0.000 title claims description 23
FLVQOAUAIBIIGO-UHFFFAOYSA-N 4-hydroxybutyl acetate Chemical compound CC(=O)OCCCCO FLVQOAUAIBIIGO-UHFFFAOYSA-N 0.000 title claims description 15
239000003054 catalyst Substances 0.000 claims abstract description 55
238000007037 hydroformylation reaction Methods 0.000 claims abstract description 54
239000000203 mixture Substances 0.000 claims abstract description 41
239000010941 cobalt Substances 0.000 claims abstract description 27
229910017052 cobalt Inorganic materials 0.000 claims abstract description 27
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 26
UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 claims abstract 3
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims description 12
239000011541 reaction mixture Substances 0.000 claims description 8
MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 claims description 7
150000001868 cobalt Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 abstract description 43
150000001299 aldehydes Chemical class 0.000 abstract description 21
150000001298 alcohols Chemical class 0.000 abstract description 14
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract description 13
IYOJOSWOUUPBRK-UHFFFAOYSA-N 1-oxobutan-2-yl acetate Chemical compound CCC(C=O)OC(C)=O IYOJOSWOUUPBRK-UHFFFAOYSA-N 0.000 abstract description 12
229910000073 phosphorus hydride Inorganic materials 0.000 abstract description 8
-1 phosphine -modified cobalt Chemical class 0.000 abstract description 6
230000009467 reduction Effects 0.000 abstract description 2
239000000047 product Substances 0.000 description 51
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 19
229910002091 carbon monoxide Inorganic materials 0.000 description 19
229940105305 carbon monoxide Drugs 0.000 description 19
229910052751 metal Inorganic materials 0.000 description 17
239000002184 metal Substances 0.000 description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
229910052739 hydrogen Inorganic materials 0.000 description 16
239000001257 hydrogen Substances 0.000 description 16
NXAWYWHMPNQUJN-UHFFFAOYSA-N (2-methyl-3-oxopropyl) acetate Chemical class O=CC(C)COC(C)=O NXAWYWHMPNQUJN-UHFFFAOYSA-N 0.000 description 13
239000007789 gas Substances 0.000 description 13
230000000694 effects Effects 0.000 description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
150000001336 alkenes Chemical class 0.000 description 9
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
CEAFMKFVSIOXOA-UHFFFAOYSA-N 1-hydroxybutan-2-yl acetate Chemical compound CCC(CO)OC(C)=O CEAFMKFVSIOXOA-UHFFFAOYSA-N 0.000 description 5
BMNRJWUOBYYCRX-UHFFFAOYSA-N 1-hydroxybutyl acetate Chemical compound CCCC(O)OC(C)=O BMNRJWUOBYYCRX-UHFFFAOYSA-N 0.000 description 5
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 5
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 5
150000002009 diols Chemical class 0.000 description 5
239000000376 reactant Substances 0.000 description 5
229910052703 rhodium Inorganic materials 0.000 description 5
239000010948 rhodium Substances 0.000 description 5
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 5
IYAIBVKPRAZUDT-UHFFFAOYSA-N (3-hydroxy-2-methylpropyl) acetate Chemical compound OCC(C)COC(C)=O IYAIBVKPRAZUDT-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000003003 phosphines Chemical class 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
238000009740 moulding (composite fabrication) Methods 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
ODKLKBUOGOLEJW-UHFFFAOYSA-N (3-acetyloxy-2-methylpropyl) acetate Chemical compound CC(=O)OCC(C)COC(C)=O ODKLKBUOGOLEJW-UHFFFAOYSA-N 0.000 description 2
XUKSWKGOQKREON-UHFFFAOYSA-N 1,4-diacetoxybutane Chemical compound CC(=O)OCCCCOC(C)=O XUKSWKGOQKREON-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
150000001242 acetic acid derivatives Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
238000007323 disproportionation reaction Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
238000006170 formylation reaction Methods 0.000 description 2
KPTMSNPLDZKSST-UHFFFAOYSA-N glyceryl diacetate or diacetin Chemical compound CC(=O)OC(CC)COC(C)=O KPTMSNPLDZKSST-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
239000003607 modifier Substances 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
IKUJAIDSWVXUGG-UHFFFAOYSA-N prop-1-enyl acetate Chemical compound CC=COC(C)=O IKUJAIDSWVXUGG-UHFFFAOYSA-N 0.000 description 2
238000012552 review Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000001149 thermolysis Methods 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
101100242191 Tetraodon nigroviridis rho gene Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
OIQOECYRLBNNBQ-UHFFFAOYSA-N carbon monoxide;cobalt Chemical compound [Co].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] OIQOECYRLBNNBQ-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001869 cobalt compounds Chemical class 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
230000022244 formylation Effects 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000013067 intermediate product Substances 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
238000006317 isomerization reaction Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA209,307A 1974-09-16 1974-09-16 Acetoxy-4 butyraldehyde et acetoxy-4 butanol Expired CA1047526A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA209,307A CA1047526A (fr)	1974-09-16	1974-09-16	Acetoxy-4 butyraldehyde et acetoxy-4 butanol

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA209,307A CA1047526A (fr)	1974-09-16	1974-09-16	Acetoxy-4 butyraldehyde et acetoxy-4 butanol

Publications (1)

Publication Number	Publication Date
CA1047526A true CA1047526A (fr)	1979-01-30

Family

ID=4101145

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA209,307A Expired CA1047526A (fr)	1974-09-16	1974-09-16	Acetoxy-4 butyraldehyde et acetoxy-4 butanol

Country Status (1)

Country	Link
CA (1)	CA1047526A (fr)

1974
- 1974-09-16 CA CA209,307A patent/CA1047526A/fr not_active Expired

Publication	Publication Date	Title
EP0104197B1 (fr)	1986-05-28	Procede de production d'ethanol
US4148830A (en)	1979-04-10	Hydroformylation of olefins
US4247486A (en)	1981-01-27	Cyclic hydroformylation process
US4973741A (en)	1990-11-27	Difunctional products from ethylene oxide and synthesis gas
US3929915A (en)	1975-12-30	Process for the production of butanediol
US4072709A (en)	1978-02-07	Production of lactic acid
CA1090823A (fr)	1980-12-02	Hydroformylation cyclique
WO1980001691A1 (fr)	1980-08-21	Procede de preparation d'aldehydes
EP0343944A2 (fr)	1989-11-29	Procédé pour la fabrication de diols-1,2 à partir d'époxides
JPH027295B2 (fr)	1990-02-16
US5004844A (en)	1991-04-02	Process for the reduction of carbonyl compounds
JP3844781B2 (ja)	2006-11-15	１，３−プロパンジオールを製造する方法
US5053562A (en)	1991-10-01	Process for making 1,3-diols from epoxides
US4017550A (en)	1977-04-12	Manufacture of 1,4-butanediol
US5135901A (en)	1992-08-04	A catalyst composition comprising rhodium, ruthenium,and a promoter
CA1155458A (fr)	1983-10-18	Procede pour l'hydroformylation selective du methanol en acetaldehyde
EP0018161B1 (fr)	1983-05-25	Aldéhyde-éthers et procédé pour leur préparation
CA1047526A (fr)	1979-01-30	Acetoxy-4 butyraldehyde et acetoxy-4 butanol
CA1048534A (fr)	1979-02-13	Esters allyliques d'acides carboxyliques et d'alcools allyliques
CA1157047A (fr)	1983-11-15	Hydroformylation de composes olefiniques
GB2075857A (en)	1981-11-25	Making hydroformylation catalysts
US5043480A (en)	1991-08-27	Difunctional products from ethylene oxide and synthesis gas
US3981931A (en)	1976-09-21	Diols by transesterification using magnesia catalysts
JPH0436251A (ja)	1992-02-06	可塑剤用アルコール
EP0150943B1 (fr)	1989-01-04	Hydroformylation d'alcool allylique