JP4178483B2 - シクロアルキルアルキルエーテル化合物の製造方法 - Google Patents
シクロアルキルアルキルエーテル化合物の製造方法 Download PDFInfo
- Publication number
- JP4178483B2 JP4178483B2 JP2008010964A JP2008010964A JP4178483B2 JP 4178483 B2 JP4178483 B2 JP 4178483B2 JP 2008010964 A JP2008010964 A JP 2008010964A JP 2008010964 A JP2008010964 A JP 2008010964A JP 4178483 B2 JP4178483 B2 JP 4178483B2
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- ion exchange
- exchange resin
- reaction
- acidic ion
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- 150000001875 compounds Chemical class 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 title claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 62
- 239000003456 ion exchange resin Substances 0.000 claims description 62
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 62
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- -1 alicyclic olefin Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 22
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 76
- 239000000203 mixture Substances 0.000 description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 150000001935 cyclohexenes Chemical class 0.000 description 14
- 150000001941 cyclopentenes Chemical class 0.000 description 14
- 239000003729 cation exchange resin Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000005443 coulometric titration Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 229920000307 polymer substrate Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- FSWCCQWDVGZMRD-UHFFFAOYSA-N 4-methylcyclohexene Chemical compound CC1CCC=CC1 FSWCCQWDVGZMRD-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910000266 aqualite Inorganic materials 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011964 heteropoly acid Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- XTCMQAVNRXZBRH-UHFFFAOYSA-N 1,3-dimethylcyclohexene Chemical compound CC1CCCC(C)=C1 XTCMQAVNRXZBRH-UHFFFAOYSA-N 0.000 description 1
- QIIAONVJAUZQQR-UHFFFAOYSA-N 1,3-dimethylcyclopentene Chemical compound CC1CCC(C)=C1 QIIAONVJAUZQQR-UHFFFAOYSA-N 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- JHJLETSOSKVZGF-UHFFFAOYSA-N 1-fluorocyclohexene Chemical compound FC1=CCCCC1 JHJLETSOSKVZGF-UHFFFAOYSA-N 0.000 description 1
- IFRIJEKNVVMZBB-UHFFFAOYSA-N 1-fluorocyclopentene Chemical compound FC1=CCCC1 IFRIJEKNVVMZBB-UHFFFAOYSA-N 0.000 description 1
- ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LMEOVPMTQBNCFK-UHFFFAOYSA-N 2-bromobutan-1-ol Chemical compound CCC(Br)CO LMEOVPMTQBNCFK-UHFFFAOYSA-N 0.000 description 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
- CXOZQHPXKPDQGT-UHFFFAOYSA-N 3-Methylcyclopentene Chemical compound CC1CCC=C1 CXOZQHPXKPDQGT-UHFFFAOYSA-N 0.000 description 1
- WCMSFBRREKZZFL-UHFFFAOYSA-N 3-cyclohexen-1-yl-Benzene Chemical compound C1CCCC(C=2C=CC=CC=2)=C1 WCMSFBRREKZZFL-UHFFFAOYSA-N 0.000 description 1
- IIUVWPOGYTYFPM-UHFFFAOYSA-N 3-methylsulfanylbutan-1-ol Chemical compound CSC(C)CCO IIUVWPOGYTYFPM-UHFFFAOYSA-N 0.000 description 1
- NCDVDTXDSDVLPL-UHFFFAOYSA-N 4-chlorocyclohexene Chemical compound ClC1CCC=CC1 NCDVDTXDSDVLPL-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XWCWNUSFQVJNDI-UHFFFAOYSA-N cyclohex-3-en-1-ylbenzene Chemical compound C1C=CCCC1C1=CC=CC=C1 XWCWNUSFQVJNDI-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- CXMYOMKBXNPDIW-UHFFFAOYSA-N cyclopenten-1-ylbenzene Chemical compound C1CCC=C1C1=CC=CC=C1 CXMYOMKBXNPDIW-UHFFFAOYSA-N 0.000 description 1
- BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 description 1
- YOXHCYXIAVIFCZ-UHFFFAOYSA-N cyclopropanol Chemical compound OC1CC1 YOXHCYXIAVIFCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- AOWTYVFGMCEIRN-UHFFFAOYSA-N ethoxycyclopentane Chemical compound CCOC1CCCC1 AOWTYVFGMCEIRN-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B49/00—Grignard reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/184—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring to a carbon atom of a non-condensed ring
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5022—Organic solvents containing oxygen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
- C11D2111/22—Electronic devices, e.g. PCBs or semiconductors
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/263—Ethers
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- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B20/00—Signal processing not specific to the method of recording or reproducing; Circuits therefor
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- G11B20/00—Signal processing not specific to the method of recording or reproducing; Circuits therefor
- G11B20/00086—Circuits for prevention of unauthorised reproduction or copying, e.g. piracy
- G11B20/0021—Circuits for prevention of unauthorised reproduction or copying, e.g. piracy involving encryption or decryption of contents recorded on or reproduced from a record carrier
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Description
本発明の第2によれば、水含有量が5重量%以下の酸性イオン交換樹脂の存在下に、シクロペンテンとメタノールとを、気体状態で反応させることを特徴とする、シクロペンチルメチルエーテルの製造方法が提供される。
分析機器:Hitachi GC390
カラム:Neutrabond Capillary Column 60×I
D0.25φ(1.5μ mdf、GLサイエンス社製)
カラム温度:50℃(10min)、100℃→300℃(20℃/min)
注入口温度:200℃
検出器温度:300℃
キャリアーガス:N2
検出器:FID
注入量:1μL
市販のスチレン系酸性イオン交換樹脂(三菱化学(株)製、商品名:RCP145、含水量46重量%)10gを乾燥機に入れ、常圧下、温度105℃付近で10時間乾燥した後、デシケーターに入れ、室温で2週間さらに乾燥した。この乾燥した酸性イオン交換樹脂の含水量をカールフィッシャー電量滴定法で測定したところ、3.0重量%であった。
上記で得た乾燥酸性イオン交換樹脂を、直径1インチ(2.54cm)、長さが40cmの反応管に詰めて、100℃で乾燥窒素ガスを5時間流通した後、室温に戻した。得られた乾燥酸性イオン交換樹脂の含水量をカールフィッシャー電量滴定法で測定したところ、水分は1.5重量%であった。このようにして得た酸性イオン交換樹脂(以下、「乾燥酸性イオン交換樹脂」という。)を反応に使用した。
参考例1において、乾燥酸性イオン交換樹脂に代えて、含水量46重量%の酸性イオン交換樹脂(三菱化学(株)製、商品名:RCP145)を使用した以外は参考例1と同様に反応を行なった。反応液をガスクロマトグラフィーにより分析したところ、シクロペンチルメチルエーテルは転化率0.4%でしか得られていなかった。
ステンレス製の密閉可能な反応容器(内容積200ml)に、シクロペンテン3.4g(0.05モル)、メタノール32g(1.0モル)及び合成ゼオライト系触媒(モービル社製、商品名:ZSM−5)3.0gを入れ、反応容器を密閉し、120℃、反応容器内の圧力1.0MPaで、6〜8時間内容物を撹拌した。反応液をガスクロマトグラフィーにより分析したところ、シクロペンチルメチルエーテルが転化率0.07%でしか得られていなかった。参考例1と同様に精製を試みたが、シクロペンチルメチルエーテルの生成量が微量であるため、単離することができなかった。
製造例1と同様にして、種々の酸性イオン交換樹脂A1〜G1を乾燥して、乾燥酸性イオン交換樹脂A2〜G2をそれぞれ得た。得られた乾燥酸性イオン交換樹脂の含水量を測定したところ、第1表に示すようにすべて1.5重量%以下であった。
酸性イオン交換樹脂A1:SPC108(バイエル社製)
酸性イオン交換樹脂B1:SPC118(バイエル社製)
酸性イオン交換樹脂C1:PK208LH(三菱化学(株)製)
酸性イオン交換樹脂D1:PK216LH(三菱化学(株)製)
酸性イオン交換樹脂E1:PK228LH(三菱化学(株)製)
酸性イオン交換樹脂F1:Amberlyst15(オルガノ(株)製)
酸性イオン交換樹脂G1:RCP145(三菱化学(株)製)
また、以下においては、酸性イオン交換樹脂A1を乾燥したものを乾燥酸性イオン交換樹脂A2とする(B2〜G2も同様である)。
実施例1〜7は、第1図(b)に示す反応装置を使用して行なった。直径2.54cm(1インチ)、長さ40cmのSUS製の反応カラム3b、3cに、上記で得られた乾燥酸性イオン交換樹脂A2〜G2をそれぞれ充填し(充填量約80ml)、カラム3b、3cのそれぞれの全体を90℃に保温した。
実施例1〜7において、乾燥酸性イオン交換樹脂A2〜G2に代えて、含水量40〜70重量%の酸性イオン交換樹脂A1〜G1を使用する以外は、実施例1〜7と同様に反応を行なった。用いた酸性イオン交換樹脂の種類、メタノールの転化率及び反応選択率を第1表にまとめた。シクロペンチルメチルエーテルは、生成量が微量であるため、単離することができなかった。
Claims (2)
- 水含有量が5重量%以下の酸性イオン交換樹脂の存在下に、脂環式オレフィンとアルコール類とを、気体状態で反応させることを特徴とする、式(1):R1−O−R2(式中、R1は置換基を有していてもよいシクロペンチル基または置換基を有していてもよいシクロヘキシル基を表し、R2は置換基を有していてもよい炭素数1〜10のアルキル基または置換基を有していてもよい炭素数3〜8のシクロアルキル基を表す。)で表されるシクロアルキルアルキルエーテル化合物の製造方法。
- 水含有量が5重量%以下の酸性イオン交換樹脂の存在下に、シクロペンテンとメタノールとを、気体状態で反応させることを特徴とする、シクロペンチルメチルエーテルの製造方法。
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EP (2) | EP1405840B1 (ja) |
JP (3) | JP4140523B2 (ja) |
KR (4) | KR20040012990A (ja) |
CN (1) | CN100509734C (ja) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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Families Citing this family (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7494962B2 (en) * | 2001-06-28 | 2009-02-24 | Zeon Corporation | Solvents containing cycloakyl alkyl ethers and process for production of the ethers |
WO2004046075A1 (ja) * | 2002-11-20 | 2004-06-03 | Zeon Corporation | シクロアルキルエーテル化合物を含有してなる結晶化用溶剤及び該溶剤を用いる結晶化方法 |
US7384667B2 (en) * | 2003-01-30 | 2008-06-10 | Alberto Blanco | System and method for producing simulated oil paintings |
JP2004292358A (ja) * | 2003-03-27 | 2004-10-21 | Nippon Zeon Co Ltd | シクロアルキルアルキルエーテルの製造方法 |
JP2004292756A (ja) * | 2003-03-28 | 2004-10-21 | Nippon Zeon Co Ltd | プライマー組成物 |
JP2004300076A (ja) * | 2003-03-31 | 2004-10-28 | Nippon Zeon Co Ltd | シクロアルキルアルキルエーテルの製造方法 |
US8557343B2 (en) | 2004-03-19 | 2013-10-15 | The Boeing Company | Activation method |
JP4386192B2 (ja) * | 2004-12-28 | 2009-12-16 | 日本ゼオン株式会社 | フルオロカーボン膜用洗浄剤 |
DE602006012798D1 (de) | 2005-01-21 | 2010-04-22 | Commw Scient Ind Res Org | Aktivierungsverfahren mithilfe eines modifikationsmittels |
JP4609642B2 (ja) * | 2005-01-31 | 2011-01-12 | 日本ゼオン株式会社 | シクロアルキルアルキルエーテルの製造方法 |
JP2006282558A (ja) * | 2005-03-31 | 2006-10-19 | Nippon Zeon Co Ltd | シクロアルキルアルキルエーテルの製造方法 |
US20070251551A1 (en) * | 2005-04-15 | 2007-11-01 | Korzenski Michael B | Removal of high-dose ion-implanted photoresist using self-assembled monolayers in solvent systems |
JP2007022921A (ja) * | 2005-07-12 | 2007-02-01 | Tosoh Finechem Corp | メチルリチウム溶液およびその製造方法 |
DE102005053553A1 (de) * | 2005-11-08 | 2007-05-16 | Heraeus Gmbh W C | Lotpasten mit harzfreien Flussmittel |
JP2007145747A (ja) * | 2005-11-28 | 2007-06-14 | Nippon Zeon Co Ltd | 有機溶剤の分別回収方法 |
DE102007026763A1 (de) * | 2007-06-09 | 2009-01-15 | Saltigo Gmbh | Verfahren zur Herstellung substituierter Heteroaromaten |
WO2010030932A2 (en) * | 2008-09-12 | 2010-03-18 | Brigham Young University | Optical data media containing an ultraviolet protection layer |
JP5437671B2 (ja) * | 2009-03-17 | 2014-03-12 | 株式会社日本触媒 | グリニヤール試薬の製造方法 |
JP5836576B2 (ja) * | 2009-09-01 | 2015-12-24 | 日本合成化学工業株式会社 | 樹脂組成物及び当該樹脂組成物を用いた多層構造体及びその製造方法 |
JP2011190216A (ja) * | 2010-03-15 | 2011-09-29 | Asahi Glass Co Ltd | (トリフルオロメチル)アルキルケトンの製造方法 |
CN101838738A (zh) * | 2010-04-27 | 2010-09-22 | 中国神华能源股份有限公司 | 一种由粉煤灰提取镓的方法 |
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US20120101307A1 (en) * | 2010-10-25 | 2012-04-26 | Basf Se | Process for the preparation of 1-methyl-1-alkoxycyclopentanes |
US20120101306A1 (en) * | 2010-10-25 | 2012-04-26 | Basf Se | Process for the preparation of 1-methylcyclopentane derivatives |
JP2012106968A (ja) * | 2010-11-19 | 2012-06-07 | Agc Seimi Chemical Co Ltd | フルオロブタジエン化合物の製造方法 |
EP2667954A1 (en) * | 2011-01-28 | 2013-12-04 | Wems, Inc. | Method and system for solvent purification |
CN102500570A (zh) * | 2011-11-01 | 2012-06-20 | 宁波市鑫友光伏有限公司 | 太阳能电池硅片清洗方法 |
CA2856196C (en) | 2011-12-06 | 2020-09-01 | Masco Corporation Of Indiana | Ozone distribution in a faucet |
WO2013146390A1 (ja) * | 2012-03-27 | 2013-10-03 | 株式会社クラレ | 3-アルコキシ-3-メチル-1-ブタノールの製造方法 |
CN105050994A (zh) | 2013-03-29 | 2015-11-11 | 日本瑞翁株式会社 | 环烷基烷基醚化合物的制造方法 |
CN104370685A (zh) * | 2014-10-20 | 2015-02-25 | 哈尔滨工业大学(威海) | 一种绿色合成四甲基联苯异构体化合物的方法 |
CN105481660B (zh) * | 2015-12-01 | 2017-09-26 | 浙江阿尔法化工科技有限公司 | 一种环戊基甲醚的连续化生产系统及合成方法 |
WO2017112795A1 (en) | 2015-12-21 | 2017-06-29 | Delta Faucet Company | Fluid delivery system including a disinfectant device |
CN108368016B (zh) * | 2015-12-28 | 2023-09-26 | 日本瑞翁株式会社 | 环戊基烷基醚化合物的制造方法 |
JP6934069B2 (ja) * | 2017-12-21 | 2021-09-08 | オルガノ株式会社 | 非水液状物質の精製方法及びイオン交換樹脂充填カートリッジの作製方法 |
US10370320B2 (en) * | 2017-12-30 | 2019-08-06 | Rohm And Haas Electronic Materials Llc | Purification methods |
CN108753494A (zh) * | 2018-05-08 | 2018-11-06 | 张家港康得新光电材料有限公司 | 一种lens清洗剂 |
KR20210104664A (ko) | 2018-12-17 | 2021-08-25 | 아란세오 도이치란드 게엠베하 | 대체 용매를 이용하여 hnbr 용액을 제조하기 위한 공정 |
RU2722163C1 (ru) * | 2019-01-09 | 2020-05-27 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Уфимский государственный нефтяной технический университет" | Способ получения простых эфиров гем-дихлорциклопропилалканолов |
US11529568B2 (en) * | 2019-03-19 | 2022-12-20 | Imagine Tf, Llc | Layered structures with spacers and channels for separation |
MX2023010771A (es) * | 2021-03-15 | 2024-01-16 | Gary david mcknight | Métodos de reacción para producir compuestos de fosforilo nitrogenado que están en composiciones fluidas in situ. |
CN114152691B (zh) * | 2021-11-26 | 2024-01-02 | 黄河三角洲京博化工研究院有限公司 | 一种气相色谱分析环戊烷及萃取剂含量的方法 |
Family Cites Families (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3496223A (en) * | 1966-12-19 | 1970-02-17 | Monsanto Co | Process for preparing phosphonic acids |
US3641159A (en) * | 1969-03-05 | 1972-02-08 | Universal Oil Prod Co | Process for the preparation of organic halides and organic ethers |
US4134924A (en) * | 1977-08-11 | 1979-01-16 | Union Carbide Corporation | Preparation of 2-cyclopentenyl ethers |
NL7803135A (nl) * | 1978-03-23 | 1979-09-25 | Shell Int Research | Werkwijze ter bereiding van tertiaire alkyl- ethers. |
JPS55149219A (en) * | 1979-05-11 | 1980-11-20 | Mitsui Toatsu Chem Inc | Preparation process of methyl tertiarybutyl ether |
US4306100A (en) | 1980-06-16 | 1981-12-15 | Standard Oil Company (Indiana) | Process for production of alkenediols |
JPS58118531A (ja) * | 1982-01-06 | 1983-07-14 | Sumitomo Chem Co Ltd | メチルタ−シヤリ−ブチルエ−テルの製造方法 |
JPS5925345A (ja) | 1982-08-02 | 1984-02-09 | Mitsubishi Gas Chem Co Inc | 第三級エ−テルの製造法 |
US4511488A (en) | 1983-12-05 | 1985-04-16 | Penetone Corporation | D-Limonene based aqueous cleaning compositions |
JPS61249945A (ja) * | 1985-04-26 | 1986-11-07 | Asahi Chem Ind Co Ltd | エ−テルの製造法 |
US4640719A (en) | 1985-07-01 | 1987-02-03 | Petroleum Fermentations N.V. | Method for printed circuit board and/or printed wiring board cleaning |
EP0241429A3 (de) * | 1986-04-11 | 1990-02-07 | Ciba-Geigy Ag | Mikrobizide Silane |
JPS62246590A (ja) * | 1986-04-17 | 1987-10-27 | Mitsubishi Chem Ind Ltd | ジチオフエノレ−ト系錯体及び同錯体を含有する光学記録媒体 |
US5192728A (en) * | 1988-06-24 | 1993-03-09 | Mobil Oil Corporation | Tin-colating microporous crystalline materials and their use as dehydrogenation, dehydrocyclization reforming catalysts |
DE3829142A1 (de) * | 1988-08-27 | 1990-03-01 | Basf Ag | Verfahren zur abtrennung von cyclohexanol |
JP2604632B2 (ja) | 1989-07-31 | 1997-04-30 | 花王株式会社 | 洗浄剤組成物 |
US5210205A (en) * | 1989-12-21 | 1993-05-11 | Ciba-Geigy Corporation | Pesticidal compositions |
JP2890603B2 (ja) * | 1990-02-16 | 1999-05-17 | 日本油脂株式会社 | 不飽和カルボン酸ジエステルの製造方法 |
JP3126190B2 (ja) * | 1991-12-16 | 2001-01-22 | 三井化学株式会社 | エーテル類の製造方法 |
JPH0794677B2 (ja) | 1992-06-18 | 1995-10-11 | 東京電線工業株式会社 | 洗浄剤 |
US5338347A (en) * | 1992-09-11 | 1994-08-16 | The Lubrizol Corporation | Corrosion inhibition composition |
JP2814896B2 (ja) * | 1993-10-25 | 1998-10-27 | 富士ゼロックス株式会社 | 静電写真用液体現像剤 |
US5529874A (en) * | 1993-05-07 | 1996-06-25 | Fuji Xerox Co., Ltd. | Liquid developer for electrophotography |
GB2281909B (en) * | 1993-09-21 | 1997-06-04 | Asahi Chemical Ind | Propylene glycol cyclohexyl ether derivatives, method of producing same and uses thereof |
DE4400464A1 (de) * | 1994-01-11 | 1995-07-13 | Bayer Ag | Endoparasitizide Mittel |
GB9406423D0 (en) | 1994-03-31 | 1994-05-25 | Ici Plc | Solvent extraction process |
US5444168A (en) * | 1994-05-16 | 1995-08-22 | Mobil Oil Corporation | Process for the production of symmetrical ethers from secondary alcohols |
JP2961304B2 (ja) * | 1996-10-08 | 1999-10-12 | 花王株式会社 | エポキシ樹脂の剥離剤組成物 |
CN1217726A (zh) * | 1997-02-26 | 1999-05-26 | 日本石油化学株式会社 | 三氟化硼配合物的回收方法及利用该方法进行的烯烃低聚物的制造方法 |
JPH10316598A (ja) * | 1997-05-16 | 1998-12-02 | Nippon Zeon Co Ltd | 弗素化炭化水素並びに洗浄剤と洗浄方法 |
EP0994089B1 (en) | 1997-05-16 | 2008-11-26 | Nippon Zeon Co., Ltd. | Polymer-containing solution and method for forming polymer film |
JPH11217526A (ja) * | 1998-02-02 | 1999-08-10 | Fuji Xerox Co Ltd | 画像表示用記録液 |
JPH11228478A (ja) * | 1998-02-17 | 1999-08-24 | Mitsubishi Chemical Corp | ジメチロールアルカナールの製造方法 |
JP2001261592A (ja) * | 2000-03-16 | 2001-09-26 | Nippon Zeon Co Ltd | 高純度シクロペンテン、その製造方法及びそれを用いるシクロペンタノールの製造方法 |
JP2002167347A (ja) * | 2000-11-30 | 2002-06-11 | Nippon Zeon Co Ltd | ジシクロペンチルエーテルの製造方法 |
US7494962B2 (en) * | 2001-06-28 | 2009-02-24 | Zeon Corporation | Solvents containing cycloakyl alkyl ethers and process for production of the ethers |
-
2002
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JP7090346B2 (ja) | 2017-07-14 | 2022-06-24 | アップコン株式会社 | 木骨造を補修する方法 |
Also Published As
Publication number | Publication date |
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WO2003002500A1 (fr) | 2003-01-09 |
KR100995840B1 (ko) | 2010-11-23 |
US20050065060A1 (en) | 2005-03-24 |
CN1543449A (zh) | 2004-11-03 |
JPWO2003002500A1 (ja) | 2004-10-14 |
EP2279995A3 (en) | 2012-01-11 |
IN2003KO01661A (ja) | 2006-03-17 |
KR100970133B1 (ko) | 2010-07-14 |
KR20080049149A (ko) | 2008-06-03 |
EP1405840A1 (en) | 2004-04-07 |
US7494962B2 (en) | 2009-02-24 |
US20080312125A1 (en) | 2008-12-18 |
JP2008156367A (ja) | 2008-07-10 |
EP2279995B1 (en) | 2013-09-18 |
KR20090085711A (ko) | 2009-08-07 |
JP2008179638A (ja) | 2008-08-07 |
EP2279995A2 (en) | 2011-02-02 |
CN100509734C (zh) | 2009-07-08 |
KR20040012990A (ko) | 2004-02-11 |
US8017813B2 (en) | 2011-09-13 |
JP4140523B2 (ja) | 2008-08-27 |
EP1405840B1 (en) | 2014-08-20 |
EP1405840A4 (en) | 2006-05-17 |
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