CA1085865A - Process for preparing cyclic ethers - Google Patents
Process for preparing cyclic ethersInfo
- Publication number
- CA1085865A CA1085865A CA273,444A CA273444A CA1085865A CA 1085865 A CA1085865 A CA 1085865A CA 273444 A CA273444 A CA 273444A CA 1085865 A CA1085865 A CA 1085865A
- Authority
- CA
- Canada
- Prior art keywords
- cyclic ether
- water
- acetic acid
- preparing
- reaction zone
- Prior art date
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 150000004292 cyclic ethers Chemical class 0.000 title claims description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000002168 ethanoic acid esters Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 16
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003377 acid catalyst Substances 0.000 claims abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 77
- 239000007788 liquid Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 13
- 239000008246 gaseous mixture Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- -1 diacetic acid ester Chemical class 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 238000007599 discharging Methods 0.000 claims description 4
- 239000013505 freshwater Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000007792 gaseous phase Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical group 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- CKGMDQVIRZYXHU-UHFFFAOYSA-N but-1-ene hydrate Chemical compound O.CCC=C CKGMDQVIRZYXHU-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 abstract description 5
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 abstract description 2
- 229960000583 acetic acid Drugs 0.000 description 20
- 235000011054 acetic acid Nutrition 0.000 description 20
- 239000002253 acid Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 8
- 239000011973 solid acid Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XUKSWKGOQKREON-UHFFFAOYSA-N 1,4-diacetoxybutane Chemical compound CC(=O)OCCCCOC(C)=O XUKSWKGOQKREON-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 238000006137 acetoxylation reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000036647 reaction Effects 0.000 description 3
- 229910000619 316 stainless steel Inorganic materials 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 238000001577 simple distillation Methods 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
- FLVQOAUAIBIIGO-UHFFFAOYSA-N 4-hydroxybutyl acetate Chemical compound CC(=O)OCCCCO FLVQOAUAIBIIGO-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000370685 Arge Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005262 decarbonization Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052716 thallium 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
- 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
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2845376A JPS52111559A (en) | 1976-03-16 | 1976-03-16 | Production of cyclic ethers |
| JP51-28453 | 1976-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085865A true CA1085865A (en) | 1980-09-16 |
Family
ID=12249074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA273,444A Expired CA1085865A (en) | 1976-03-16 | 1977-03-08 | Process for preparing cyclic ethers |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4094887A (forum.php) |
| JP (1) | JPS52111559A (forum.php) |
| CA (1) | CA1085865A (forum.php) |
| DE (1) | DE2710265C2 (forum.php) |
| FR (1) | FR2344554A1 (forum.php) |
| GB (1) | GB1517144A (forum.php) |
| IT (1) | IT1072805B (forum.php) |
| NL (1) | NL7702812A (forum.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN102816139A (zh) * | 2012-07-30 | 2012-12-12 | 南通星辰合成材料有限公司 | 四氢呋喃的提纯工艺 |
| CN106432143B (zh) * | 2016-09-30 | 2019-02-19 | 浙江捷达科技有限公司 | 一种二氢呋喃连续化生产及分离的装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1170222A (en) * | 1968-06-10 | 1969-11-12 | Shell Int Research | Process for the preparation of Tetrahydrofuran and/or Homologues thereof |
| US4005112A (en) * | 1973-11-30 | 1977-01-25 | General Electric Company | Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid |
| US4011244A (en) * | 1973-12-03 | 1977-03-08 | General Electric Company | Process for preparing tetrahydrofuran |
| US4010171A (en) * | 1973-12-03 | 1977-03-01 | General Electric Company | Process for preparing tetrahydrofuran |
| US4005113A (en) * | 1973-12-03 | 1977-01-25 | General Electric Company | Multi-step process for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid |
| DE2442886B2 (de) * | 1974-09-07 | 1976-09-30 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von tetrahydrofuran |
-
1976
- 1976-03-16 JP JP2845376A patent/JPS52111559A/ja active Granted
-
1977
- 1977-03-07 US US05/774,899 patent/US4094887A/en not_active Expired - Lifetime
- 1977-03-08 CA CA273,444A patent/CA1085865A/en not_active Expired
- 1977-03-08 GB GB9752/77A patent/GB1517144A/en not_active Expired
- 1977-03-09 DE DE2710265A patent/DE2710265C2/de not_active Expired
- 1977-03-15 IT IT67565/77A patent/IT1072805B/it active
- 1977-03-15 FR FR7707652A patent/FR2344554A1/fr active Granted
- 1977-03-16 NL NL7702812A patent/NL7702812A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2344554B1 (forum.php) | 1980-04-11 |
| GB1517144A (en) | 1978-07-12 |
| US4094887A (en) | 1978-06-13 |
| FR2344554A1 (fr) | 1977-10-14 |
| JPS565396B2 (forum.php) | 1981-02-04 |
| NL7702812A (nl) | 1977-09-20 |
| DE2710265A1 (de) | 1977-09-22 |
| DE2710265C2 (de) | 1986-01-16 |
| IT1072805B (it) | 1985-04-13 |
| JPS52111559A (en) | 1977-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4032458A (en) | Production of 1,4-butanediol | |
| CN101426756B (zh) | 连续制备不饱和羧酸酐的方法 | |
| US4198530A (en) | Production of tertiary butyl methyl ether | |
| AU707824B2 (en) | Process for preparing gamma-butyrolactone, butane-1,4-diol and tetrahydrofuran | |
| US4093633A (en) | Process for preparing tetrahydrofuran | |
| US5214185A (en) | Continuous process for preparing dimethyl carbonate | |
| CA1184202A (en) | Process for continuously preparing ethylene glycol | |
| EP0277168A1 (en) | PROCESS FOR THE CO-PRODUCTION OF BUTANE-1,4-DIOL AND $i(GAMMA)-BUTYROLACTONE | |
| US4172961A (en) | Production of 1,4-butanediol | |
| GB2146636A (en) | Process for producing acrylic acid | |
| CA1085865A (en) | Process for preparing cyclic ethers | |
| US4156685A (en) | Process for producing a hydrofuran and a 1,4-diol | |
| US4802956A (en) | Process for the purification of dimethylether by distillation | |
| US4562283A (en) | Continuous separation of maleic anhydride from gaseous reaction mixtures | |
| AU9753398A (en) | Process for the preparation of butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran | |
| CN1103767C (zh) | 2,5－二氢呋喃转化成2,3－二氢呋喃的连续法 | |
| GB1561603A (en) | Process for the separation of water from gas mixtures formed in the manufacture of vinyl acetate | |
| JPH0629280B2 (ja) | 粗テトラヒドロフランの精製方法 | |
| US4124600A (en) | Preparation of tetrahydrofuran | |
| US4005112A (en) | Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid | |
| JPH0572371B2 (forum.php) | ||
| CA1088084A (en) | Process for producing a cyclic ether from an acetic ester of a 1,4-glycol | |
| CA1324781C (en) | Purification of alkyl glyoxylate in a continuous column by azeotropic distillation | |
| KR100934056B1 (ko) | 테트라히드로푸란과 피롤리돈을 동시에 제조하는 방법 | |
| JP5912407B2 (ja) | ジアルキルカーボネートの連続的製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |