CA1037486A - Mode de preparation de tetahydrofuranne - Google Patents

Mode de preparation de tetahydrofuranne

Info

Publication number: CA1037486A
Authority: CA; Canada
Prior art keywords: butanediol; carboxylic acid; catalyst; silica; grams
Prior art date: 1973-12-03
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

CA211,038A

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.)

1973-12-03

Filing date

1974-10-09

Publication date

1978-08-29

1974-10-09 Application filed by General Electric Co filed Critical General Electric Co

1978-08-29 Application granted granted Critical

1978-08-29 Publication of CA1037486A publication Critical patent/CA1037486A/fr

Status Expired legal-status Critical Current

Links

WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 48
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 26
238000004519 manufacturing process Methods 0.000 title claims abstract description 5
239000003054 catalyst Substances 0.000 claims abstract description 31
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
-1 carboxylic acid diester Chemical class 0.000 claims abstract description 17
238000010438 heat treatment Methods 0.000 claims abstract description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 16
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
238000005984 hydrogenation reaction Methods 0.000 claims description 8
239000010457 zeolite Substances 0.000 claims description 8
BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 5
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
238000004064 recycling Methods 0.000 claims description 4
239000000377 silicon dioxide Substances 0.000 claims description 4
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims 4
239000007790 solid phase Substances 0.000 claims 4
150000007942 carboxylates Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 13
239000000047 product Substances 0.000 description 12
150000002009 diols Chemical class 0.000 description 11
239000002253 acid Substances 0.000 description 9
XUKSWKGOQKREON-UHFFFAOYSA-N 1,4-diacetoxybutane Chemical compound CC(=O)OCCCCOC(C)=O XUKSWKGOQKREON-UHFFFAOYSA-N 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 6
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 5
150000001733 carboxylic acid esters Chemical class 0.000 description 5
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
KYCXTUXIIANKNP-UHFFFAOYSA-N 1-acetyloxybutyl acetate Chemical compound CCCC(OC(C)=O)OC(C)=O KYCXTUXIIANKNP-UHFFFAOYSA-N 0.000 description 3
FLVQOAUAIBIIGO-UHFFFAOYSA-N 4-hydroxybutyl acetate Chemical compound CC(=O)OCCCCO FLVQOAUAIBIIGO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
229910021536 Zeolite Inorganic materials 0.000 description 3
150000001242 acetic acid derivatives Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000395 magnesium oxide Substances 0.000 description 3
239000008188 pellet Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
BMNRJWUOBYYCRX-UHFFFAOYSA-N 1-hydroxybutyl acetate Chemical compound CCCC(O)OC(C)=O BMNRJWUOBYYCRX-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
230000015556 catabolic process 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
238000006731 degradation reaction Methods 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000007323 disproportionation reaction Methods 0.000 description 2
238000007037 hydroformylation reaction Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
NXAWYWHMPNQUJN-UHFFFAOYSA-N (2-methyl-3-oxopropyl) acetate Chemical compound O=CC(C)COC(C)=O NXAWYWHMPNQUJN-UHFFFAOYSA-N 0.000 description 1
ODKLKBUOGOLEJW-UHFFFAOYSA-N (3-acetyloxy-2-methylpropyl) acetate Chemical compound CC(=O)OCC(C)COC(C)=O ODKLKBUOGOLEJW-UHFFFAOYSA-N 0.000 description 1
IYAIBVKPRAZUDT-UHFFFAOYSA-N (3-hydroxy-2-methylpropyl) acetate Chemical compound OCC(C)COC(C)=O IYAIBVKPRAZUDT-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
IYOJOSWOUUPBRK-UHFFFAOYSA-N 1-oxobutan-2-yl acetate Chemical compound CCC(C=O)OC(C)=O IYOJOSWOUUPBRK-UHFFFAOYSA-N 0.000 description 1
IEDVQOXHVRVPIX-UHFFFAOYSA-N 2-(oxolan-2-yl)acetic acid Chemical compound OC(=O)CC1CCCO1 IEDVQOXHVRVPIX-UHFFFAOYSA-N 0.000 description 1
OZTUJRSHRYXRFW-UHFFFAOYSA-N 4-oxobutyl acetate Chemical compound CC(=O)OCCCC=O OZTUJRSHRYXRFW-UHFFFAOYSA-N 0.000 description 1
241001527902 Aratus Species 0.000 description 1
241000905957 Channa melasoma Species 0.000 description 1
241000761389 Copa Species 0.000 description 1
244000261422 Lysimachia clethroides Species 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000010724 circulating oil Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
229910052900 illite Inorganic materials 0.000 description 1
238000007373 indentation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
210000003739 neck Anatomy 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
VGIBGUSAECPPNB-UHFFFAOYSA-L nonaaluminum;magnesium;tripotassium;1,3-dioxido-2,4,5-trioxa-1,3-disilabicyclo[1.1.1]pentane;iron(2+);oxygen(2-);fluoride;hydroxide Chemical compound [OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[F-].[Mg+2].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[K+].[K+].[K+].[Fe+2].O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2 VGIBGUSAECPPNB-UHFFFAOYSA-L 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
101150002764 purA gene Proteins 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
238000006798 ring closing metathesis reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000002226 simultaneous effect Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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

Landscapes

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

CA211,038A 1973-12-03 1974-10-09 Mode de preparation de tetahydrofuranne Expired CA1037486A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US42085373A	1973-12-03	1973-12-03

Publications (1)

Publication Number	Publication Date
CA1037486A true CA1037486A (fr)	1978-08-29

Family

ID=23668103

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA211,038A Expired CA1037486A (fr)	1973-12-03	1974-10-09	Mode de preparation de tetahydrofuranne

Country Status (8)

Country	Link
JP (1)	JPS5093961A (fr)
BR (1)	BR7409959A (fr)
CA (1)	CA1037486A (fr)
DE (1)	DE2456780A1 (fr)
FR (1)	FR2266700B1 (fr)
GB (1)	GB1487200A (fr)
IT (1)	IT1026704B (fr)
NL (1)	NL7415775A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2442886B2 (de) *	1974-09-07	1976-09-30	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von tetrahydrofuran
DE2856455A1 (de) *	1978-12-28	1980-07-17	Basf Ag	Verfahren zur herstellung von tetrahydrofuran
DE4005295A1 (de) *	1990-02-20	1991-08-22	Basf Ag	Verfahren zur gewinnung von tetrahydrofuran aus gemischen, die tetrahydrofuran, 1,4-butandiol, (gamma)-butyrolacton und bernsteinsaeureester enthalten

1974
- 1974-10-09 CA CA211,038A patent/CA1037486A/fr not_active Expired
- 1974-11-28 BR BR995974A patent/BR7409959A/pt unknown
- 1974-11-29 FR FR7439176A patent/FR2266700B1/fr not_active Expired
- 1974-11-30 DE DE19742456780 patent/DE2456780A1/de not_active Withdrawn
- 1974-12-02 JP JP49137073A patent/JPS5093961A/ja active Pending
- 1974-12-02 GB GB5202074A patent/GB1487200A/en not_active Expired
- 1974-12-02 IT IT3006974A patent/IT1026704B/it active
- 1974-12-03 NL NL7415775A patent/NL7415775A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
GB1487200A (en)	1977-09-28
JPS5093961A (fr)	1975-07-26
IT1026704B (it)	1978-10-20
DE2456780A1 (de)	1975-06-05
AU7585974A (en)	1976-06-03
BR7409959A (pt)	1976-05-25
FR2266700B1 (fr)	1980-04-11
NL7415775A (nl)	1975-06-05
FR2266700A1 (fr)	1975-10-31

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JP5124366B2 (ja)	2013-01-23	９９％を越える純度を有する１，６−ヘキサンジオールの製法
US4471136A (en)	1984-09-11	Preparation of ethyl acetate
CA1048550A (fr)	1979-02-13	Synthese d'alcools allyliques
KR20010032097A (ko)	2001-04-16	1,6-헥산디올 및 6-히드록시카프로산 또는 그의에스테르의 제조 방법
US3948986A (en)	1976-04-06	Alpha-hydroxy or alkoxy acid preparation
US4005113A (en)	1977-01-25	Multi-step process for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
US4656297A (en)	1987-04-07	Coproduction of butanediol and tetrahydrofuran and their subsequent separation from the reaction product mixture
CA1037486A (fr)	1978-08-29	Mode de preparation de tetahydrofuranne
US4005112A (en)	1977-01-25	Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
CA1064960A (fr)	1979-10-23	Procede pour la preparation d'esters allyliques d'acides carboxyliques
US4010171A (en)	1977-03-01	Process for preparing tetrahydrofuran
MXPA02009174A (es)	2003-03-12	Procedimiento para la preparacion de propano-1,3-diol mediante hidrogenacion de fase de vapor de 3-hidroxipropanal, beta-propiolactona, oligomeros de beta-propiolactona, esteres de acido 3-hidroxipropanoico o mezclas de los mismos.
US4136099A (en)	1979-01-23	Production of tetrahydrofuran from 1,4-butanediol using tungsten on alumina catalysts
US4011244A (en)	1977-03-08	Process for preparing tetrahydrofuran
US4124600A (en)	1978-11-07	Preparation of tetrahydrofuran
CA1048534A (fr)	1979-02-13	Esters allyliques d'acides carboxyliques et d'alcools allyliques
US4044059A (en)	1977-08-23	One-step method for hydrolyzing and hydrogenating acetal-aldehydes
US7071362B2 (en)	2006-07-04	Process for producing alicyclic aldehydes
CA1037487A (fr)	1978-08-29	Mode de preparation de tetrahydrofuranne
US3981931A (en)	1976-09-21	Diols by transesterification using magnesia catalysts
CA1037488A (fr)	1978-08-29	Mode de preparation de tetrahydrofuranne
KR20090034817A (ko)	2009-04-08	말레산 무수물 생산시의 푸마르산 침착물의 방지 방법
DE2461922A1 (de)	1976-07-08	Verfahren zur herstellung von tetrahydrofuran
JPH05255135A (ja)	1993-10-05	イソブチレンの製法
CA1088085A (fr)	1980-10-21	Obtention de tetrahydrofurane