CA1048533A - Deformylhydratation des acetoxybutyraldehydes - Google Patents

Deformylhydratation des acetoxybutyraldehydes

Info

Publication number: CA1048533A
Authority: CA; Canada
Prior art keywords: mixture; acetoxybutyraldehyde; produce; allyl acetate; acetate
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

CA74209308A

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

1979-02-13

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

1974-09-16 Priority to CA74209308A priority Critical patent/CA1048533A/fr

1979-02-13 Application granted granted Critical

1979-02-13 Publication of CA1048533A publication Critical patent/CA1048533A/fr

Status Expired legal-status Critical Current

Links

IYOJOSWOUUPBRK-UHFFFAOYSA-N 1-oxobutan-2-yl acetate Chemical class CCC(C=O)OC(C)=O IYOJOSWOUUPBRK-UHFFFAOYSA-N 0.000 title claims abstract description 41
239000000203 mixture Substances 0.000 claims abstract description 65
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims abstract description 44
OZTUJRSHRYXRFW-UHFFFAOYSA-N 4-oxobutyl acetate Chemical compound CC(=O)OCCCC=O OZTUJRSHRYXRFW-UHFFFAOYSA-N 0.000 claims abstract description 41
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 38
239000003054 catalyst Substances 0.000 claims abstract description 36
238000007037 hydroformylation reaction Methods 0.000 claims abstract description 26
229910000510 noble metal Inorganic materials 0.000 claims abstract description 23
230000007935 neutral effect Effects 0.000 claims abstract description 13
UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 91
238000000034 method Methods 0.000 claims description 33
150000001299 aldehydes Chemical class 0.000 claims description 26
230000008569 process Effects 0.000 claims description 26
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
NXAWYWHMPNQUJN-UHFFFAOYSA-N (2-methyl-3-oxopropyl) acetate Chemical compound O=CC(C)COC(C)=O NXAWYWHMPNQUJN-UHFFFAOYSA-N 0.000 claims description 15
238000005984 hydrogenation reaction Methods 0.000 claims description 14
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 13
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
239000012808 vapor phase Substances 0.000 claims description 12
229910052763 palladium Inorganic materials 0.000 claims description 9
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 9
FLVQOAUAIBIIGO-UHFFFAOYSA-N 4-hydroxybutyl acetate Chemical compound CC(=O)OCCCCO FLVQOAUAIBIIGO-UHFFFAOYSA-N 0.000 claims description 8
238000005886 esterification reaction Methods 0.000 claims description 8
229910052703 rhodium Inorganic materials 0.000 claims description 7
239000010948 rhodium Substances 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
230000008878 coupling Effects 0.000 claims description 5
238000010168 coupling process Methods 0.000 claims description 5
238000005859 coupling reaction Methods 0.000 claims description 5
230000006872 improvement Effects 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
229910017052 cobalt Inorganic materials 0.000 claims description 4
239000010941 cobalt Substances 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
230000015556 catabolic process Effects 0.000 claims description 3
150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 2
150000002009 diols Chemical class 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
239000000758 substrate Substances 0.000 claims description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 2
230000015572 biosynthetic process Effects 0.000 claims 2
238000006731 degradation reaction Methods 0.000 claims 2
239000011541 reaction mixture Substances 0.000 claims 2
239000011949 solid catalyst Substances 0.000 claims 2
230000001590 oxidative effect Effects 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 71
229920000728 polyester Polymers 0.000 abstract description 3
239000000047 product Substances 0.000 description 31
238000009835 boiling Methods 0.000 description 22
239000001257 hydrogen Substances 0.000 description 13
229910052739 hydrogen Inorganic materials 0.000 description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
238000004821 distillation Methods 0.000 description 11
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 10
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 9
229940090181 propyl acetate Drugs 0.000 description 9
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 9
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000007791 liquid phase Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 7
229910002091 carbon monoxide Inorganic materials 0.000 description 7
239000007789 gas Substances 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 6
239000002253 acid Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
239000006227 byproduct Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000006170 formylation reaction Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
-1 terephthalic acid Chemical class 0.000 description 3
BMNRJWUOBYYCRX-UHFFFAOYSA-N 1-hydroxybutyl acetate Chemical class CCCC(O)OC(C)=O BMNRJWUOBYYCRX-UHFFFAOYSA-N 0.000 description 2
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
238000003763 carbonization Methods 0.000 description 2
239000012159 carrier gas Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000007701 flash-distillation Methods 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
239000000376 reactant Substances 0.000 description 2
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 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
241000282320 Panthera leo Species 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
241000950638 Symphysodon discus Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
238000005882 aldol condensation reaction Methods 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000006324 decarbonylation Effects 0.000 description 1
238000006606 decarbonylation reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
230000022244 formylation Effects 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
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
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 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000013021 overheating Methods 0.000 description 1
238000005691 oxidative coupling reaction Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1

Landscapes

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

CA74209308A 1974-09-16 1974-09-16 Deformylhydratation des acetoxybutyraldehydes Expired CA1048533A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA74209308A CA1048533A (fr)	1974-09-16	1974-09-16	Deformylhydratation des acetoxybutyraldehydes

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA74209308A CA1048533A (fr)	1974-09-16	1974-09-16	Deformylhydratation des acetoxybutyraldehydes

Publications (1)

Publication Number	Publication Date
CA1048533A true CA1048533A (fr)	1979-02-13

Family

ID=4101146

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA74209308A Expired CA1048533A (fr)	1974-09-16	1974-09-16	Deformylhydratation des acetoxybutyraldehydes

Country Status (1)

Country	Link
CA (1)	CA1048533A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0295548B1 (fr) *	1987-06-15	1992-03-18	BASF Aktiengesellschaft	Procédé pour la fabrication d'esters d'acide penténoique à partir d'esters d'acide formyl-valérique
US10183899B2 (en)	2016-11-10	2019-01-22	Chevron Phillips Chemical Company Lp	Normal alpha olefin synthesis using metathesis and dehydroformylation
US10723672B2 (en)	2018-02-26	2020-07-28	Chervon Phillips Chemical Company Lp	Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation
US11123723B2 (en)	2018-02-26	2021-09-21	The Regents Of The University Of California	Oxidative dehydroxymethylation of alcohols to produce olefins
US12151993B2 (en)	2021-09-10	2024-11-26	Chevron Phillips Chemical Company Lp	Selective 1-hexene/1-octene production with 1-decene

1974
- 1974-09-16 CA CA74209308A patent/CA1048533A/fr not_active Expired

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0295548B1 (fr) *	1987-06-15	1992-03-18	BASF Aktiengesellschaft	Procédé pour la fabrication d'esters d'acide penténoique à partir d'esters d'acide formyl-valérique
US10183899B2 (en)	2016-11-10	2019-01-22	Chevron Phillips Chemical Company Lp	Normal alpha olefin synthesis using metathesis and dehydroformylation
US10435334B2 (en)	2016-11-10	2019-10-08	Chevron Phillips Chemical Company Lp	Normal alpha olefin synthesis using metathesis and dehydroformylation
US10723672B2 (en)	2018-02-26	2020-07-28	Chervon Phillips Chemical Company Lp	Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation
US11123723B2 (en)	2018-02-26	2021-09-21	The Regents Of The University Of California	Oxidative dehydroxymethylation of alcohols to produce olefins
US12151993B2 (en)	2021-09-10	2024-11-26	Chevron Phillips Chemical Company Lp	Selective 1-hexene/1-octene production with 1-decene

Publication	Publication Date	Title
CA1191866A (fr)	1985-08-13	Methode d'hydroformylation
KR19980701460A (ko)	1998-05-15	하이드로포르밀화 공정(hydroformylation process)
EP0586522B1 (fr)	1997-07-23	Procede de production de melanges de 2-hydroxytetrahydrofurane et de 4-hydroxybutanal
US8809594B2 (en)	2014-08-19	Dual catalyst system for the self-condensation of alcohols
US4138588A (en)	1979-02-06	Process for the improved manufacture of 2-ethylhexanol
CA1048533A (fr)	1979-02-13	Deformylhydratation des acetoxybutyraldehydes
US3020314A (en)	1962-02-06	Process for the preparation of alcohols, aldehydes and ketones
US3253018A (en)	1966-05-24	Decobalting aldehydic acid ester oxo reaction mixtures using oxalic acid at reflux temperatures and atmospheric pressure
EP0155002A2 (fr)	1985-09-18	Hydroformylation de 3-méthyl-3-butène-1-ol et utilisation de tels produits d'hydroformylation
US4096192A (en)	1978-06-20	Process for the preparation of 2-methyl-1,3-propanediol
US4258214A (en)	1981-03-24	Process for the production of aldehydes
US4035408A (en)	1977-07-12	Process for hydroformylation of allyl acetate or 1-propenyl acetate
US3941851A (en)	1976-03-02	1,4-Butanediol from hydrogenated hydroformylated allyl acetate
US3880913A (en)	1975-04-29	Dehydroformylation of acetoxybutyraldehydes
Yokokawa et al.	1964	Studies of the Organic Reactions of Metal Carbonyl. III. The Hydroformylation of Olefin Oxides
KR840000276B1 (ko)	1984-03-13	알데히드-에테르의 제조방법
EP0038609A1 (fr)	1981-10-28	Préparation du 2-hydroxytétrahydrofurane
CA1048534A (fr)	1979-02-13	Esters allyliques d'acides carboxyliques et d'alcools allyliques
EP0365996B1 (fr)	1995-01-11	Procédé de production d'alcools homo-allyliques
US3236869A (en)	1966-02-22	Allenic acids
CA1202326A (fr)	1986-03-25	Raffinage d'un aldehyde brut
CA1042470A (fr)	1978-11-14	Mode de preparation de diols
US2678950A (en)	1954-05-18	Process of producing acrolein
US3341601A (en)	1967-09-12	Preparation of diels-alder adducts
JP2827431B2 (ja)	1998-11-25	可塑剤用アルコールの製造法