JPS6140656B2 - - Google Patents
Info
- Publication number
- JPS6140656B2 JPS6140656B2 JP57079714A JP7971482A JPS6140656B2 JP S6140656 B2 JPS6140656 B2 JP S6140656B2 JP 57079714 A JP57079714 A JP 57079714A JP 7971482 A JP7971482 A JP 7971482A JP S6140656 B2 JPS6140656 B2 JP S6140656B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- cobalt
- acetal
- reaction
- present
- 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
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 16
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000010941 cobalt Substances 0.000 claims description 11
- 229910017052 cobalt Inorganic materials 0.000 claims description 11
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 11
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 10
- 150000002739 metals Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000001869 cobalt compounds Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000011734 sodium Substances 0.000 description 17
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 150000001241 acetals Chemical class 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- -1 organic acid salts Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910007926 ZrCl Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001477 organic nitrogen group Chemical group 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- UIOXNNAWANDJCZ-UHFFFAOYSA-N 1,1-dimethoxypropane Chemical compound CCC(OC)OC UIOXNNAWANDJCZ-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- SWTCCCJQNPGXLQ-UHFFFAOYSA-N 1-(1-butoxyethoxy)butane Chemical compound CCCCOC(C)OCCCC SWTCCCJQNPGXLQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 229910018119 Li 3 PO 4 Inorganic materials 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical group [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- MBNMGGKBGCIEGF-UHFFFAOYSA-N 1,1-diethoxypropane Chemical compound CCOC(CC)OCC MBNMGGKBGCIEGF-UHFFFAOYSA-N 0.000 description 1
- MISTZQJSHHTDCF-UHFFFAOYSA-N 1-(1-propoxyethoxy)propane Chemical compound CCCOC(C)OCCC MISTZQJSHHTDCF-UHFFFAOYSA-N 0.000 description 1
- MYCXIDKAJBXPCZ-UHFFFAOYSA-N 1-ethoxy-1-methoxyethane Chemical compound CCOC(C)OC MYCXIDKAJBXPCZ-UHFFFAOYSA-N 0.000 description 1
- CBQQIJZTSICUJL-UHFFFAOYSA-N 1-ethoxy-1-methoxypropane Chemical compound CCOC(CC)OC CBQQIJZTSICUJL-UHFFFAOYSA-N 0.000 description 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- IPUDBCXGMBSQGH-UHFFFAOYSA-N 2-methoxybutan-1-ol Chemical compound CCC(CO)OC IPUDBCXGMBSQGH-UHFFFAOYSA-N 0.000 description 1
- 241001289141 Babr Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910013184 LiBO Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 229910019440 Mg(OH) Inorganic materials 0.000 description 1
- 241001460678 Napo <wasp> Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910003514 Sr(OH) Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- OBWXQDHWLMJOOD-UHFFFAOYSA-H cobalt(2+);dicarbonate;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Co+2].[Co+2].[Co+2].[O-]C([O-])=O.[O-]C([O-])=O OBWXQDHWLMJOOD-UHFFFAOYSA-H 0.000 description 1
- AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 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
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019820 disodium diphosphate Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004704 methoxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical group [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical group [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Description
本発明は２―アルコキシ―アルコールの製造法
に関する。さらに詳しくは一酸化炭素および水素
と、アセタールを反応させて２―アルコキシ―ア
ルコールを製造する方法に関する。
従来、合成ガスとアセタール特にジメチルアセ
タールからの２―アルコキシ―アルコールの製造
方法としては米国特許第2555950号明細書に記載
の方法が公知方法として知られている。しかしな
がら、この方法は高温高圧下（250℃、850〜
950atm）の過酷な条件を必要としているにもか
かわらず、反応活性は低く、収率（４〜15％）も
低い。
本発明者らは従来法の欠点を解消すべく、反応
条件の緩和、反応速度および収率の向上を目的と
して鋭意研究を設け、本発明に到達した。
すなわち本発明は
(a)一酸化炭素および(b)水素と
(c)式
The present invention relates to a method for producing 2-alkoxy-alcohols. More specifically, the present invention relates to a method for producing 2-alkoxy-alcohol by reacting carbon monoxide and hydrogen with acetal. Conventionally, the method described in US Pat. No. 2,555,950 has been known as a method for producing 2-alkoxy-alcohol from synthesis gas and acetal, particularly dimethyl acetal. However, this method is not possible under high temperature and high pressure (250℃, 850℃~850℃).
Despite requiring harsh conditions (950 atm), the reaction activity is low and the yield (4-15%) is low. In order to overcome the drawbacks of conventional methods, the present inventors conducted extensive research aimed at relaxing reaction conditions and improving reaction rate and yield, and arrived at the present invention. That is, the present invention combines (a) carbon monoxide, (b) hydrogen, and (c) formula
【式】のアセタール
を反応させて２―アルコキシ―アルコールを製造
するに際し、コバルトまたはコバルト化合物と
周期表のＡ族、Ａ族、Ａ族、Ａ族、
Ａ族、Ａ族、Ｂ族、およびＢ族からなる群
から選ばれた１種以上の金属または該金属の化合
物を用いることを特徴とする２―アルコキシーア
ルコールの製造法。
〔式中、R1、R2およびR3は炭素数１〜６のア
ルキル基、あるいは炭素数７〜12のアラールキル
基を示し、おたがいに同一でも異なつていてもよ
い。〕
本発明による一酸化炭素および水素とアセター
ルの詳細な反応機構は明確ではないが、総合反応
として次の化学反応式によつて表わすことができ
る。
本発明において主触媒金属として使用するコバ
ルトまたはコバルト化合物としては有機・無機の
コバルト化合物が利用できる。たとえば金属コバ
ルト、コバルトオクタカルボニル、コバルトヒド
ロカルボニル、酸化コバルト、硝酸コバルト、水
酸化コバルト、ヨウ化コバルト、塩基性炭酸コバ
ルトなどの塩基性塩、酢酸コバルト、ナフテン酸
コバルトなどの有機酸塩、ビスアセチルアセトナ
トコバルトなどのキレート化合物等が使用され
る。
本発明ではコバルトまたはコバルト化合物とと
もに周期表のＡ族、Ａ族、Ａ族、Ａ族、
Ａ族、Ａ族、Ｂ族およびＢ族からなる群
から選ばれた一種以上の金属または該金属の化合
物とするが、それらの金属元素としては
Ａ族：リチウム、ナトリウム
Ａ族：マグネシウム、カルシウム、ストロン
チウム、バリウム
Ａ族：イツトリウム
Ａ族：チタン、ジルコニウム、ハフニウム
Ａ族：パナジウム、ニオブ、タンタル
Ａ族：クロム、モリブデン、タングステン
Ｂ族：アンチモン
Ｂ族：テルル
であり、好ましくは
Ａ族：リチウム、ナトリウム
Ａ族：バリウム
、Ａ族：イツトリウム
Ａ族：チタン、ジルコニウム
Ａ族：バナジウム
Ａ族：クロム、モリブデン、タングステン
Ｂ族：アンチモン
Ｂ族：テルル
であり、さらに好ましくは
Ａ族：リチウム、ナトリウム
Ａ族：バリウム
Ａ族：チタン
であり、特に
Ａ族：リチウム
が有効である。
ところで、前記の金属または金属化合物の形態
は任意のあらゆる型で利用できる。たとえば、金
属それ自体、または微粉砕した形の金属、ラネー
金属の形態あるいは炭酸塩、酸化物、水酸化物、
硝酸塩、硫酸塩、燐酸塩、ハロゲン化物、シアン
化物、チオシアン化物、スルフオン酸塩、C1〜
C3の低級アルコキシドたとえばメトキシドまた
はエトキシド、フエノキシド、カルボキシイオン
が１〜20炭素原子のアルカン酸から誘導される金
属カルボン酸塩、オキシハロゲン化物、水素化
物、亜硝酸塩、亜硫酸塩、亜リン酸塩、アルチル
アセトン塩、硫化物、およびアンモニア、シア
ン、アミン類、アミノ酸類等を配位した化合物あ
るいはフエニル基、アルキル基が結合した有機金
属化合物がある。その一部を例示すれば、Li，
LiC2H3O2・2H2O，LiBO2，LiBr・2H2O，
Li2CO3，LiHCO2，LiCl，Li2CrO4・2H2O，
Li3C6H5O7・4H2O，LiF，Li2SiF6・2H2O，
LiHCO2・H2O，LiOH，LiOH・H2O，LiI，
LiI・3H2O，Li2C2O4，Li2O，Li3PO4，Li3PO4・
12H2O，LiH2PO4，LiC7H5O3，Li2SO4，
Li2SO4・H2O，LiHSO4，Li2SO3，NaC2H3O2，
NaC2H3O2，NaNH4HPO4・4H2O，NaC7H5O2，
NaBO2，NaBO2・4H2O，Na2B4O7，NaBr，
NaBr・2H2O，Na2CO3，Na2CO3・H2O，Na3H
（CO3）2・2H2O，NaHCO3，NaCl，Na3C6H5O7・
2H2O，Na2S2O6・2H2O，NaOH，NaHCO2，
NaH2P2O6・6H2O，NaH2PO2・H2O，NaI，
NaI・2H2O，NaC3H5O3，Na2S2O5，Na2MoO4・
2H2O，Na2MoO7，Na2C2O4，NaHC2O4・H2O，
NaBO3・H2O，Na2S2O3，NaH2PO4・H2O，
Na2HPO4，Na3PO4，NaPO3，Na4P2O7，
Na2H2P2O7，NaKC4H4O6・4H2O，NaC7H5O3，
Na2SO4，NaHSO4，Na2SO3，NaHSO3，
Na2S2O3，Mg（C2H3O2）2，MgCl2，MgI2，
MgO，Mg（OH）2，Ca（C2H3O2）2，CaCO3，
CaI2，CaO，Ca（OH）2，Sr（C2H3O2）2，
SrCO3，SrI2，SrO，Sr（OH）2，Ba
（C2H3O2）2，BaBr2，BaCO3，BaCl2，BaS2O6・
2H2O，Ba（OH）2・8H2O，BaI2，BaO，
BaPO3，BaSO3，BaSO4，Ｙ（C2H3O2）・
4H2O，Ｙ（OH）3，YI3，Y2O3，TiBr2，TiBr3，
TiBr4，TiCl2，TiCl3，TiCl4，TiI2，TiI3，
TiI4，Ti2（C2O4）3・10H2O，TiO，Ti2O3，
TiO2，TiOBr2，TiOCl2，TiOI2，ZrBr2，
ZrBr3，ZrBr4，ZrCl2，ZrCl3，ZrCl4，Zr
（OH）4，ZrI3，ZrI4，ZrO2，ZrOCl2，Zr
（SO4）2，HfBr2，HfCl4，HfO2，VBr3，VBr4，
VCl2，V2O3，NbBr3，NbCl4，NbI5，Nb2O3，Cr
（C2H3O2）2，CrCl2，CrI3，CrO3，Mo（CO）6，
H2MoO4，MoCl3，WOBr4，H2W4O13・9H2O，
H2WO4，SbBr2，SbBr3，SbI5，Sb2O3，TeBr2，
TeBr2I2，TeO2等である。前記金属または金属化
合物のうち、入手の難易、価格等の点から、酢酸
等の有機酸塩または酸化物の形態の金属化合物を
用いることは好ましい実施態様である。
本発明において使用するコバルト触媒の使用量
は金属原子基準で反応液の全容量、１当り
0.001〜10ｇ―atom、好ましくは0.005〜５ｇ―
atom、さらに好ましくは0.01〜２ｇ―atomであ
る。コバルト触媒とともに用いられる周期表の
Ａ族、Ａ族、Ａ族、Ａ族、Ａ族、Ａ
族、Ｂ族およびＢ族の金属または該金属の化
合物はコバルト１ｇ―atomに対して0.01〜100ｇ
―atom、好ましくは0.03〜30ｇ―atom、さらに
好ましくは0.1〜20ｇ―atomの範囲で使用される
が、その使用量は通常、反応液の全容量を基準に
して１ｇ当り10-6〜30ｇ―atom、好ましくは10-4
〜20ｇ―atom、さらに好ましくは10-3〜10ｇ―
atomの範囲が選ばれる。
本発明の方法を実施するための反応は反応温度
がたとえば50〜350℃、好ましくは80〜300℃、さ
らに好ましくは100〜250℃の範囲が適当である。
反応全圧は反応媒体を液相に保ち、一酸化炭素お
よび水素を適当な分圧に保つのに十分であればよ
い。一酸化炭素および水素の好適な分圧は１〜
500気圧、最適な分圧は３〜300気圧、さらに最適
な分圧は５〜200気圧であるが、これより広い
0.05〜1000気圧の範囲の分圧でもさしつかえな
い。
前述の生成反応式における原料ガスの一酸化炭
素対水素の化学量論理は１：２である。しかしな
がら実際上は一酸化炭素対水素のモル比ははるか
に広い範囲、１：100〜100：１、好ましくは１：
50〜50：１、さらに好ましくは１：10〜10：１を
使用できる。一酸化炭素対水素の化学量論理比に
近い混合ガスの時、最良の結果がが得られるので
一酸化炭素対水素のモル比を１：0.5〜１：５の
範囲にすることは特に好ましい。又、本発明で使
用される一酸化炭素及び水素は各々単独で反応帯
へ圧入してよく、又、一酸化炭素及び水素混合の
いわゆる“合成ガス”の形態で導入しても良い。
又、これらの原料ガスは必ずしも純度の高いもの
ではなくても良く、二酸化炭素、メタン、窒素、
希ガス等を含有していても良い。しかし極端に低
い純度の原料ガスは反応系の圧力を増加するので
好ましくない。
本発明の主原料であるアセタールは式When producing a 2-alkoxy-alcohol by reacting the acetal of [Formula], cobalt or a cobalt compound and Group A, Group A, Group A, Group A of the periodic table,
A method for producing a 2-alkoxy alcohol, characterized by using one or more metals selected from the group consisting of Group A, Group A, Group B, and Group B, or a compound of the metal. [In the formula, R 1 , R 2 and R 3 represent an alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 12 carbon atoms, and may be the same or different. Although the detailed reaction mechanism of carbon monoxide and hydrogen and acetal according to the present invention is not clear, the overall reaction can be expressed by the following chemical reaction formula. As the cobalt or cobalt compound used as the main catalyst metal in the present invention, organic and inorganic cobalt compounds can be used. For example, metallic cobalt, cobalt octacarbonyl, cobalt hydrocarbonyl, cobalt oxide, cobalt nitrate, cobalt hydroxide, cobalt iodide, basic salts such as basic cobalt carbonate, organic acid salts such as cobalt acetate and cobalt naphthenate, bisacetyl Chelate compounds such as cobalt acetonate are used. In the present invention, along with cobalt or a cobalt compound, group A, group A, group A, group A of the periodic table,
One or more metals selected from the group consisting of Group A, Group A, Group B, and Group B, or compounds of these metals, and the metal elements include: Group A: lithium, sodium Group A: magnesium, calcium, Strontium, barium Group A: Yttrium Group A: Titanium, zirconium, hafnium Group A: Panadium, niobium, tantalum Group A: Chromium, molybdenum, tungsten Group B: Antimony Group B: Tellurium, preferably Group A: Lithium, sodium Group A: barium, Group A: yttrium Group A: titanium, zirconium Group A: vanadium Group A: chromium, molybdenum, tungsten Group B: antimony Group B: tellurium, more preferably Group A: lithium, sodium Group A: Barium Group A: Titanium, and Group A: Lithium is particularly effective. Incidentally, the metals or metal compounds mentioned above can be used in any and all forms. For example, the metal itself or in finely divided form, in the form of Raney metals or in the form of carbonates, oxides, hydroxides,
Nitrates, sulfates, phosphates, halides, cyanides, thiocyanides, sulfonates, C1 ~
C 3 lower alkoxides, such as methoxides or ethoxides, phenoxides, metal carboxylates, oxyhalides, hydrides, nitrites, sulfites, phosphites, in which the carboxy ion is derived from alkanoic acids of 1 to 20 carbon atoms; There are altylacetone salts, sulfides, compounds coordinated with ammonia, cyanide, amines, amino acids, etc., and organometallic compounds to which phenyl groups and alkyl groups are bonded. To give some examples, Li,
LiC 2 H 3 O 2・2H 2 O, LiBO 2 , LiBr・2H 2 O,
Li 2 CO 3 , LiHCO 2 , LiCl, Li 2 CrO 4・2H 2 O,
Li 3 C 6 H 5 O 7・4H 2 O, LiF, Li 2 SiF 6・2H 2 O,
LiHCO 2 H 2 O, LiOH, LiOH H 2 O, LiI,
LiI・3H 2 O, Li 2 C 2 O 4 , Li 2 O, Li 3 PO 4 , Li 3 PO 4・
12H 2 O, LiH 2 PO 4 , LiC 7 H 5 O 3 , Li 2 SO 4 ,
Li 2 SO 4・H 2 O, LiHSO 4 , Li 2 SO 3 , NaC 2 H 3 O 2 ,
NaC 2 H 3 O 2 , NaNH 4 HPO 4・4H 2 O, NaC 7 H 5 O 2 ,
NaBO 2 , NaBO 2・4H 2 O, Na 2 B 4 O 7 , NaBr,
NaBr・2H 2 O, Na 2 CO 3 , Na 2 CO 3・H 2 O, Na 3 H
(CO 3 ) 2・2H 2 O, NaHCO 3 , NaCl, Na 3 C 6 H 5 O 7・
2H 2 O, Na 2 S 2 O 6・2H 2 O, NaOH, NaHCO 2 ,
NaH 2 P 2 O 6・6H 2 O, NaH 2 PO 2・H 2 O, NaI,
NaI・2H 2 O, NaC 3 H 5 O 3 , Na 2 S 2 O 5 , Na 2 MoO 4・
2H 2 O, Na 2 MoO 7 , Na 2 C 2 O 4 , NaHC 2 O 4・H 2 O,
NaBO 3・H 2 O, Na 2 S 2 O 3 , NaH 2 PO 4・H 2 O,
Na 2 HPO 4 , Na 3 PO 4 , NaPO 3 , Na 4 P 2 O 7 ,
Na2H2P2O7 , NaKC4H4O6 ・ 4H2O , NaC7H5O3 , _ _ _
Na 2 SO 4 , NaHSO 4 , Na 2 SO 3 , NaHSO 3 ,
Na 2 S 2 O 3 , Mg (C 2 H 3 O 2 ) 2 , MgCl 2 , MgI 2 ,
MgO, Mg(OH) 2 , Ca(C 2 H 3 O 2 ) 2 , CaCO 3 ,
CaI 2 , CaO, Ca(OH) 2 , Sr(C 2 H 3 O 2 ) 2 ,
SrCO 3 , SrI 2 , SrO, Sr(OH) 2 , Ba
(C 2 H 3 O 2 ) 2 , BaBr 2 , BaCO 3 , BaCl 2 , BaS 2 O 6・
2H 2 O, Ba(OH) 2・8H 2 O, BaI 2 , BaO,
BaPO 3 , BaSO 3 , BaSO 4 , Y(C 2 H 3 O 2 )・
4H 2 O, Y(OH) 3 , YI 3 , Y 2 O 3 , TiBr 2 , TiBr 3 ,
TiBr 4 , TiCl 2 , TiCl 3 , TiCl 4 , TiI 2 , TiI 3 ,
TiI 4 , Ti 2 (C 2 O 4 ) 3・10H 2 O, TiO, Ti 2 O 3 ,
TiO 2 , TiOBr 2 , TiOCl 2 , TiOI 2 , ZrBr 2 ,
ZrBr 3 , ZrBr 4 , ZrCl 2 , ZrCl 3 , ZrCl 4 , Zr
(OH) 4 , ZrI 3 , ZrI 4 , ZrO 2 , ZrOCl 2 , Zr
(SO 4 ) 2 , HfBr 2 , HfCl 4 , HfO 2 , VBr 3 , VBr 4 ,
VCl 2 , V 2 O 3 , NbBr 3 , NbCl 4 , NbI 5 , Nb 2 O 3 , Cr
(C 2 H 3 O 2 ) 2 , CrCl 2 , CrI 3 , CrO 3 , Mo(CO) 6 ,
H 2 MoO 4 , MoCl 3 , WOBr 4 , H 2 W 4 O 13・9H 2 O,
H 2 WO 4 , SbBr 2 , SbBr 3 , SbI 5 , Sb 2 O 3 , TeBr 2 ,
TeBr 2 I 2 , TeO 2 , etc. Among the metals or metal compounds mentioned above, it is a preferred embodiment to use metal compounds in the form of organic acid salts or oxides such as acetic acid in terms of availability, cost, and the like. The amount of cobalt catalyst used in the present invention is per total volume of the reaction solution on a metal atom basis.
0.001-10g-atom, preferably 0.005-5g-
Atom, more preferably 0.01 to 2 g-atom. Group A, Group A, Group A, Group A, Group A, A of the periodic table used with cobalt catalysts
0.01 to 100 g of metals of Group B, Group B, and Group B metals or compounds of these metals per 1 g-atom of cobalt.
-atom, preferably 0.03 to 30g-atom, more preferably 0.1 to 20g-atom, but the amount used is usually 10 -6 to 30g per 1g based on the total volume of the reaction solution. atoms, preferably 10 -4
~20g-atom, more preferably 10-3 ~10g-
A range of atoms is selected. The reaction temperature for carrying out the method of the present invention is suitably in the range of, for example, 50 to 350°C, preferably 80 to 300°C, and more preferably 100 to 250°C.
The total reaction pressure need only be sufficient to maintain the reaction medium in the liquid phase and carbon monoxide and hydrogen at appropriate partial pressures. The preferred partial pressure of carbon monoxide and hydrogen is 1~
500 atm, the optimal partial pressure is 3 to 300 atm, and the optimal partial pressure is 5 to 200 atm, but wider than this.
Partial pressures in the range of 0.05 to 1000 atm are also acceptable. The stoichiometric ratio of carbon monoxide to hydrogen in the raw material gas in the above-mentioned production reaction equation is 1:2. However, in practice the molar ratio of carbon monoxide to hydrogen has a much wider range, from 1:100 to 100:1, preferably 1:
50-50:1, more preferably 1:10-10:1 can be used. A molar ratio of carbon monoxide to hydrogen in the range of 1:0.5 to 1:5 is particularly preferred since the best results are obtained with a gas mixture close to the stoichiometric ratio of carbon monoxide to hydrogen. Further, carbon monoxide and hydrogen used in the present invention may be injected into the reaction zone individually, or may be introduced in the form of a so-called "synthesis gas" in which carbon monoxide and hydrogen are mixed.
In addition, these raw material gases do not necessarily have to be of high purity; carbon dioxide, methane, nitrogen,
It may contain a rare gas or the like. However, raw material gas of extremely low purity is undesirable because it increases the pressure of the reaction system. Acetal, the main raw material of the present invention, has the formula
【式】のアセタールである。式中、
R1，R2およびR3は炭素数１〜６のアルキル基、
あるいは炭素数７〜12のアラールキル基を示し、
おたがいに同一でも異なつていてもよい。かかる
アセタールの例として、アセトアルデヒドジメチ
ルアセタール、プロピオンアルデヒドジメチルア
セタール、アセトアルデヒドジエチルアセター
ル、プロピオンアルデヒドジエチルアセタール、
アセトアルデヒドメチルエチルアセタール、ピロ
ピオンアルデヒドメチルエチルアセタール、アセ
トアルデヒドジプロピルアセタール、アセトアル
デヒドジブチルアセタール、フエニルアセトアル
デヒドジメチルアセタール、トリルアセトアルデ
ヒドジメチルアセタール等を挙げることができ
る。
また、アセタールは基礎原料をエチレンなどの
石油製品に由来しない方法として、たとえばメタ
ノールと合成ガスの反応（特公昭48―2525、特開
昭51―149213、特開昭52―136110、特開昭52―
136111等）によつて生成するもの、あるいはこれ
から誘導されるものを供給することもできる。
本発明において使用される溶媒はベンゼン、ト
ルエン、キシレン、メシチレン、トリメチルベン
ゼン等の芳香族炭化水素、ペンタン、ヘキサン、
ヘプタン、オクタン等の脂肪族炭化水素、テトラ
ヒドロフラン、アニソール等のエーテル、酢酸メ
チル、酢酸エチル、プロピオン酸メチル等の有機
酸エステル等が挙げられる。
本発明の方法においては、類縁反応において常
用される三価または五価の有機窒素族化合物を用
いない。三価または五価の有機窒素族化合物は安
定性に乏しく、その使用によつて一定時間毎に新
たな有機窒素族化合物を追加して活性の低下を防
ぐ必要がある上、更に副生物の分離除去に多大の
エネルギーが必要となる。その点、本発明の触媒
系では副生物を生ずるものがなく、飛躍的に触媒
寿命を延ばせる上に、製品の分離精製が容易で、
エネルギーの節約にも寄与する。
本発明の方法は回分式、連続式のいずれの反応
型式であつても好適に実施可能である。反応液か
らの生成物及び触媒の回収については蒸留などの
公知の方法により実施出来る。
以下、実施例により本発明を更に詳しく説明す
るが、本発明は以下の実施例に限定されるもので
はない。
実施例 １〜16
ステンレス製100ml容量電磁回転撹拌器付オー
トクレーブに、表１に示すように所定量の１，１
―ジメトキシエタン、触媒、溶媒を仕込み、オー
トクレーブ内を窒素置換したのち、所定圧の水素
と一酸化炭素を圧入した。表１に示す所定の温度
に昇温し撹拌させながら所定の時間反応させた。
反応器を冷却後、反応液をガスクロマトグラフイ
ーにより分析した。結果を表２に示す。
実施例 17
１，１―ジメトキシエタンの代りに１，１―ジ
メトキシプロパンを使用した他は実施例１と同様
にして実験を行なつた。実験条件を表１に示す。
原料の転化率は85.4％、生成物２―メトキシ―
ブタノールの選択率68.0％、生成速度は6.41mo
／．Hrであつた。
比較例 １〜３
助触媒を使用しない他は実施例１と同様にして
実験を行なつた。実験条件を表１に、結果を表２
に示す。It is an acetal of [Formula]. In the formula, R 1 , R 2 and R 3 are alkyl groups having 1 to 6 carbon atoms,
Or it represents an aralkyl group having 7 to 12 carbon atoms,
They may be the same or different. Examples of such acetals include acetaldehyde dimethyl acetal, propionaldehyde dimethyl acetal, acetaldehyde diethylacetal, propionaldehyde diethylacetal,
Examples include acetaldehyde methyl ethyl acetal, propionaldehyde methyl ethyl acetal, acetaldehyde dipropyl acetal, acetaldehyde dibutyl acetal, phenylacetaldehyde dimethyl acetal, and tolylacetaldehyde dimethyl acetal. In addition, acetal can be produced using methods that do not use petroleum products such as ethylene as the basic raw material, such as the reaction of methanol and synthesis gas (Japanese Patent Publication No. 48-2525, Japanese Patent Application Publication No. 149213-1971, Japanese Patent Application Publication No. 136110-1977, Japanese Patent Application Publication No. 52-1982). ―
136111 etc.) or derived from it. Solvents used in the present invention include aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and trimethylbenzene, pentane, hexane,
Examples include aliphatic hydrocarbons such as heptane and octane, ethers such as tetrahydrofuran and anisole, and organic acid esters such as methyl acetate, ethyl acetate and methyl propionate. In the method of the present invention, trivalent or pentavalent organic nitrogen group compounds commonly used in analogous reactions are not used. Trivalent or pentavalent organic nitrogen group compounds have poor stability, and when they are used, it is necessary to add new organic nitrogen group compounds at regular intervals to prevent a decrease in activity, and it is also necessary to separate by-products. Removal requires a large amount of energy. In this respect, the catalyst system of the present invention does not produce any by-products, dramatically extending the catalyst life, and making it easy to separate and purify the product.
It also contributes to energy savings. The method of the present invention can be suitably carried out in either batchwise or continuous reaction mode. The products and catalyst can be recovered from the reaction solution by known methods such as distillation. EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the following Examples. Examples 1 to 16 A predetermined amount of 1, 1 as shown in Table 1 was placed in a stainless steel 100 ml autoclave equipped with an electromagnetic rotary stirrer.
- Dimethoxyethane, a catalyst, and a solvent were charged, and the inside of the autoclave was replaced with nitrogen, then hydrogen and carbon monoxide were injected at a predetermined pressure. The temperature was raised to a predetermined temperature shown in Table 1, and the mixture was reacted for a predetermined time while stirring.
After cooling the reactor, the reaction solution was analyzed by gas chromatography. The results are shown in Table 2. Example 17 An experiment was carried out in the same manner as in Example 1 except that 1,1-dimethoxypropane was used instead of 1,1-dimethoxyethane. The experimental conditions are shown in Table 1. Conversion rate of raw material was 85.4%, product 2-methoxy-
Butanol selectivity 68.0%, production rate 6.41mo
/． It was Hr. Comparative Examples 1 to 3 Experiments were conducted in the same manner as in Example 1 except that no promoter was used. Experimental conditions are shown in Table 1, and results are shown in Table 2.
Shown below.
【表】【table】
【表】【table】
Claims (1)
するに際し、コバルトまたはコバルト化合物と、 周期表のＡ族、Ａ族、Ａ族、Ａ族、
Ａ族、Ａ族、Ｂ族、およびＢ族からなる群
から選ばれた１種以上の金属または該金属の化合
物を用いることを特徴とする２―アルコキシ―ア
ルコールの製造法。 〔式中、R1，R2およびR3は炭素数１〜６のア
ルキル基、あるいは炭素数７〜12のアラールキル
基を示し、おたがいに同一でも異なつていてもよ
い。〕[Claims] 1. When producing a 2-alkoxy-alcohol by reacting (a) carbon monoxide and (b) hydrogen with (c) an acetal of formula [formula], cobalt or a cobalt compound, A group, A group, A group, A group,
A method for producing a 2-alkoxy-alcohol, which comprises using one or more metals selected from the group consisting of Group A, Group A, Group B, and Group B, or a compound of the metal. [In the formula, R 1 , R 2 and R 3 represent an alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 12 carbon atoms, and may be the same or different. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57079714A JPS58198431A (en) | 1982-05-12 | 1982-05-12 | Preparation of 2-alkoxy-alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57079714A JPS58198431A (en) | 1982-05-12 | 1982-05-12 | Preparation of 2-alkoxy-alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58198431A JPS58198431A (en) | 1983-11-18 |
| JPS6140656B2 true JPS6140656B2 (en) | 1986-09-10 |
Family
ID=13697871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57079714A Granted JPS58198431A (en) | 1982-05-12 | 1982-05-12 | Preparation of 2-alkoxy-alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58198431A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9056313B2 (en) | 2011-06-24 | 2015-06-16 | Eastman Chemical Company | Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals |
| US8785697B2 (en) | 2011-06-24 | 2014-07-22 | Eastman Chemical Company | Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals |
| US8829206B2 (en) | 2011-06-24 | 2014-09-09 | Eastman Chemical Company | Production of cyclic acetals or ketals using solid acid catalysts |
| US9388105B2 (en) | 2011-06-24 | 2016-07-12 | Eastman Chemical Company | Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals |
| US8969598B2 (en) | 2011-06-24 | 2015-03-03 | Eastman Chemical Company | Production of cyclic acetals or ketals using liquid-phase acid catalysts |
| US9000229B2 (en) | 2011-06-24 | 2015-04-07 | Eastman Chemical Company | Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals |
| US8829207B2 (en) | 2011-06-24 | 2014-09-09 | Eastman Chemical Company | Production of cyclic acetals by reactive distillation |
-
1982
- 1982-05-12 JP JP57079714A patent/JPS58198431A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58198431A (en) | 1983-11-18 |
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