CA1037487A - Mode de preparation de tetrahydrofuranne - Google Patents

Mode de preparation de tetrahydrofuranne

Info

Publication number: CA1037487A
Authority: CA; Canada
Prior art keywords: silica; mixture; tetrahydrofuran; diols; diol
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

CA211,068A

Other languages

English (en)

Other versions

CA211068S (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 CA1037487A publication Critical patent/CA1037487A/fr

Status Expired legal-status Critical Current

Links

WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 35
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 21
238000004519 manufacturing process Methods 0.000 title abstract description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 30
239000003054 catalyst Substances 0.000 claims abstract description 25
230000018044 dehydration Effects 0.000 claims abstract description 19
238000006297 dehydration reaction Methods 0.000 claims abstract description 19
238000010438 heat treatment Methods 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 17
150000002009 diols Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 11
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
238000006243 chemical reaction Methods 0.000 claims description 7
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 6
-1 allyl carboxylate Chemical class 0.000 claims description 6
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 6
239000000377 silicon dioxide Substances 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
239000000395 magnesium oxide Substances 0.000 claims description 4
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
238000007037 hydroformylation reaction Methods 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
208000005156 Dehydration Diseases 0.000 claims 4
229940083957 1,2-butanediol Drugs 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
239000012535 impurity Substances 0.000 claims 2
239000002243 precursor Substances 0.000 claims 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
235000012245 magnesium oxide Nutrition 0.000 claims 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
238000005984 hydrogenation reaction Methods 0.000 description 5
150000002148 esters Chemical class 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
239000012808 vapor phase Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910021536 Zeolite Inorganic materials 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000006136 alcoholysis reaction Methods 0.000 description 2
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
244000261422 Lysimachia clethroides Species 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
239000004927 clay Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000007257 deesterification 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
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
229910052621 halloysite Inorganic materials 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229910052900 illite Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 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
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 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
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229910052757 nitrogen 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
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 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

Landscapes

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

CA211,068A 1973-12-03 1974-10-09 Mode de preparation de tetrahydrofuranne Expired CA1037487A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US42085273A	1973-12-03	1973-12-03

Publications (1)

Publication Number	Publication Date
CA1037487A true CA1037487A (fr)	1978-08-29

Family

ID=23668098

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA211,068A Expired CA1037487A (fr)	1973-12-03	1974-10-09	Mode de preparation de tetrahydrofuranne

Country Status (1)

Country	Link
CA (1)	CA1037487A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4656297A (en) *	1985-03-11	1987-04-07	Amoco Corporation	Coproduction of butanediol and tetrahydrofuran and their subsequent separation from the reaction product mixture
WO2015038548A1 (fr) *	2013-09-10	2015-03-19	Invista Technologies S.A R.L.	Procédé amélioré de production de tétrahydrofuranne

1974
- 1974-10-09 CA CA211,068A patent/CA1037487A/fr not_active Expired

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4656297A (en) *	1985-03-11	1987-04-07	Amoco Corporation	Coproduction of butanediol and tetrahydrofuran and their subsequent separation from the reaction product mixture
WO2015038548A1 (fr) *	2013-09-10	2015-03-19	Invista Technologies S.A R.L.	Procédé amélioré de production de tétrahydrofuranne
CN105531266A (zh) *	2013-09-10	2016-04-27	因温斯特技术公司	用于制造四氢呋喃的改进型方法
CN105531266B (zh) *	2013-09-10	2018-01-19	因温斯特技术公司	用于制造四氢呋喃的改进型方法

Publication	Publication Date	Title
CA1048550A (fr)	1979-02-13	Synthese d'alcools allyliques
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
CA1154014A (fr)	1983-09-20	Reactions catalysees par des protons dans lesquelles l'eau n'est pas un reactif stoechiometrique; catalyse par des argiles stratifiees avec echange cationique metallique
CA1128544A (fr)	1982-07-27	Procede d'obtention d'ethylesters d'acides carboxyliques aliphatiques
US4010171A (en)	1977-03-01	Process for preparing tetrahydrofuran
US4656297A (en)	1987-04-07	Coproduction of butanediol and tetrahydrofuran and their subsequent separation from the reaction product mixture
US4005113A (en)	1977-01-25	Multi-step process for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
CA1037487A (fr)	1978-08-29	Mode de preparation de tetrahydrofuranne
TW460444B (en)	2001-10-21	Hydrogenation process for production of at least one C4 compound selected from butane-1,4-diol, γ-butyrolactone and tetrahydrofuran
US4011244A (en)	1977-03-08	Process for preparing tetrahydrofuran
US4005112A (en)	1977-01-25	Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
KR100878914B1 (ko)	2009-01-15	테트라히드로푸란의 제조 방법
EP1313723B1 (fr)	2006-03-01	Procede de fabrication de lactones
CA1236486A (fr)	1988-05-10	Procede en continu pour l'obtention de 1,2- pentanediol
US4110403A (en)	1978-08-29	Process for preparing β,γ-unsaturated aldehydes
US4136099A (en)	1979-01-23	Production of tetrahydrofuran from 1,4-butanediol using tungsten on alumina catalysts
US4124600A (en)	1978-11-07	Preparation of tetrahydrofuran
CA1037486A (fr)	1978-08-29	Mode de preparation de tetahydrofuranne
CA1042470A (fr)	1978-11-14	Mode de preparation de diols
CA1048517A (fr)	1979-02-13	Butyrolactone-4
CA1048534A (fr)	1979-02-13	Esters allyliques d'acides carboxyliques et d'alcools allyliques
CA1037488A (fr)	1978-08-29	Mode de preparation de tetrahydrofuranne
DE2461922A1 (de)	1976-07-08	Verfahren zur herstellung von tetrahydrofuran
US4080366A (en)	1978-03-21	Conversion of esters of 1,4-butanediol to tetrahydrofuran
CA1088085A (fr)	1980-10-21	Obtention de tetrahydrofurane