AU751399B2 - Process for the preparation of butanediol, butyrolactone and tetrahydrofuran - Google Patents
Process for the preparation of butanediol, butyrolactone and tetrahydrofuran Download PDFInfo
- Publication number
- AU751399B2 AU751399B2 AU31560/99A AU3156099A AU751399B2 AU 751399 B2 AU751399 B2 AU 751399B2 AU 31560/99 A AU31560/99 A AU 31560/99A AU 3156099 A AU3156099 A AU 3156099A AU 751399 B2 AU751399 B2 AU 751399B2
- Authority
- AU
- Australia
- Prior art keywords
- process according
- high boiling
- boiling solvent
- esterification
- maleic anhydride
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 61
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims description 56
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims description 28
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 title claims description 6
- 229930188620 butyrolactone Natural products 0.000 title claims description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 238000009835 boiling Methods 0.000 claims description 81
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 69
- 239000002904 solvent Substances 0.000 claims description 68
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 58
- 238000005886 esterification reaction Methods 0.000 claims description 56
- 230000032050 esterification Effects 0.000 claims description 54
- 239000003054 catalyst Substances 0.000 claims description 53
- 238000005984 hydrogenation reaction Methods 0.000 claims description 46
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 45
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical group COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 32
- -1 C 4 compound Chemical class 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 27
- 238000007254 oxidation reaction Methods 0.000 claims description 27
- 230000003647 oxidation Effects 0.000 claims description 25
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 20
- 229960001826 dimethylphthalate Drugs 0.000 claims description 20
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 14
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 14
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical group COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 12
- 230000003197 catalytic effect Effects 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 10
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- 238000005201 scrubbing Methods 0.000 claims description 9
- 239000002912 waste gas Substances 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 150000004702 methyl esters Chemical group 0.000 claims description 8
- 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 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000003456 ion exchange resin Substances 0.000 claims description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- MJHNUUNSCNRGJE-UHFFFAOYSA-N trimethyl benzene-1,2,4-tricarboxylate Chemical group COC(=O)C1=CC=C(C(=O)OC)C(C(=O)OC)=C1 MJHNUUNSCNRGJE-UHFFFAOYSA-N 0.000 claims description 4
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 3
- 150000004668 long chain fatty acids Chemical class 0.000 claims description 3
- 238000010926 purge Methods 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 230000001174 ascending effect Effects 0.000 claims description 2
- PCFNKFGGJYQMTR-UHFFFAOYSA-N dibutyl naphthalene-2,6-dicarboxylate Chemical group C1=C(C(=O)OCCCC)C=CC2=CC(C(=O)OCCCC)=CC=C21 PCFNKFGGJYQMTR-UHFFFAOYSA-N 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- RJIFVNWOLLIBJV-UHFFFAOYSA-N tributyl benzene-1,2,4-tricarboxylate Chemical group CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C(C(=O)OCCCC)=C1 RJIFVNWOLLIBJV-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000007327 hydrogenolysis reaction Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IZMOTZDBVPMOFE-UHFFFAOYSA-N dimethyl dodecanedioate Chemical compound COC(=O)CCCCCCCCCCC(=O)OC IZMOTZDBVPMOFE-UHFFFAOYSA-N 0.000 description 6
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229960002380 dibutyl phthalate Drugs 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- 101100410404 Arabidopsis thaliana PUMPKIN gene Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 239000000498 cooling water Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 229940014772 dimethyl sebacate Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JQCVPZXMGXKNOD-UHFFFAOYSA-N 1,2-dibenzylbenzene Chemical compound C=1C=CC=C(CC=2C=CC=CC=2)C=1CC1=CC=CC=C1 JQCVPZXMGXKNOD-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- PYWJUJAIGZXCMW-UHFFFAOYSA-N dibutyl dodecanedioate Chemical compound CCCCOC(=O)CCCCCCCCCCC(=O)OCCCC PYWJUJAIGZXCMW-UHFFFAOYSA-N 0.000 description 2
- CZGCYHISZCRQFR-UHFFFAOYSA-N dimethyl 2-methoxybutanedioate Chemical compound COC(=O)C(OC)CC(=O)OC CZGCYHISZCRQFR-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- ZSQCNVWYBBKUHS-UHFFFAOYSA-N (2,3-dimethylphenyl)-phenylmethanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C ZSQCNVWYBBKUHS-UHFFFAOYSA-N 0.000 description 1
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- GGMPTLAAIUQMIE-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobiphenyl Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=CC=CC=C1 GGMPTLAAIUQMIE-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KWKAPIYICPFWRC-YPKPFQOOSA-N 4-o-dodecyl 1-o-methyl (z)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C/C(=O)OC KWKAPIYICPFWRC-YPKPFQOOSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- WERYXYBDKMZEQL-CQDYUVAPSA-N butane-1,4-diol Chemical group O[13CH2]CC[13CH2]O WERYXYBDKMZEQL-CQDYUVAPSA-N 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
- SVGGKWILBMPIJV-UHFFFAOYSA-N butyl (9Z,12Z)-octadeca-9,12-dienoate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCCCC SVGGKWILBMPIJV-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- ANSWCYTXKAIJOK-UHFFFAOYSA-N dibutyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCOC(=O)C1CCCCC1C(=O)OCCCC ANSWCYTXKAIJOK-UHFFFAOYSA-N 0.000 description 1
- HEJZJSIRBLOWPD-WCWDXBQESA-N didodecyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCCCC HEJZJSIRBLOWPD-WCWDXBQESA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical class CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 1
- MPDGBCOIHNLQMR-UHFFFAOYSA-N dimethyl naphthalene-2,3-dicarboxylate Chemical compound C1=CC=C2C=C(C(=O)OC)C(C(=O)OC)=CC2=C1 MPDGBCOIHNLQMR-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IODOXLXFXNATGI-UHFFFAOYSA-N methyl naphthalene-2-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OC)=CC=C21 IODOXLXFXNATGI-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical group COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98302163 | 1998-03-23 | ||
| EP98302163A EP0962438B1 (en) | 1998-03-23 | 1998-03-23 | Process for the preparation of 1,4-butanediol, butyrolactone and tetrahydrofuran. |
| PCT/GB1999/000881 WO1999048852A1 (en) | 1998-03-23 | 1999-03-19 | Process for the preparation of butanediol, butyrolactone and tetrahydrofuran |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3156099A AU3156099A (en) | 1999-10-18 |
| AU751399B2 true AU751399B2 (en) | 2002-08-15 |
Family
ID=8234727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU31560/99A Ceased AU751399B2 (en) | 1998-03-23 | 1999-03-19 | Process for the preparation of butanediol, butyrolactone and tetrahydrofuran |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6274743B1 (enExample) |
| EP (1) | EP0962438B1 (enExample) |
| JP (1) | JP2002507587A (enExample) |
| CN (1) | CN1158233C (enExample) |
| AR (1) | AR015737A1 (enExample) |
| AU (1) | AU751399B2 (enExample) |
| BR (1) | BR9908993A (enExample) |
| CA (1) | CA2325499A1 (enExample) |
| DE (1) | DE69800886T2 (enExample) |
| ES (1) | ES2158645T3 (enExample) |
| ID (1) | ID26243A (enExample) |
| MY (1) | MY124354A (enExample) |
| NO (1) | NO20004695D0 (enExample) |
| SA (1) | SA99200188B1 (enExample) |
| TW (1) | TW557294B (enExample) |
| WO (1) | WO1999048852A1 (enExample) |
| ZA (1) | ZA200002941B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19818340A1 (de) * | 1998-04-23 | 1999-10-28 | Basf Ag | Verfahren zur Herstellung von Gemischen aus 1,4-Butandiol, Tetrahydrofuran und gamma-Butyrolacton |
| MY122525A (en) * | 1999-10-12 | 2006-04-29 | Kvaerner Process Tech Ltd | Process for the simultaneous production of maleic anyhydride and its hydrogenated derivatives |
| TWI266760B (en) * | 2000-03-20 | 2006-11-21 | Kvaerner Process Tech Ltd | Process for the preparation of propane-1,3-diol |
| GB0117090D0 (en) * | 2001-07-12 | 2001-09-05 | Kvaerner Process Tech Ltd | Process |
| KR100495335B1 (ko) * | 2002-11-15 | 2005-06-14 | 주식회사 엘지화학 | 스팀의 직접접촉을 이용한 고분자 회수방법 |
| GB0325530D0 (en) | 2003-10-31 | 2003-12-03 | Davy Process Techn Ltd | Process |
| GB0325526D0 (en) | 2003-10-31 | 2003-12-03 | Davy Process Techn Ltd | Process |
| GB0421928D0 (en) | 2004-10-01 | 2004-11-03 | Davy Process Techn Ltd | Process |
| MY157438A (en) | 2010-09-24 | 2016-06-15 | Basf Se | Process for the production of tetrahydrofuran |
| US9186599B2 (en) | 2010-09-24 | 2015-11-17 | Basf Se | Process for isolating tetrahydrofuran |
| EP2782893B1 (en) | 2011-11-25 | 2017-08-23 | Conser SPA | Process for producing 1,4-butanediol, gamma-butyrolactone and tetrahydrofuran by hydrogenating dialkyl maleate in mixed liquid/vapor phase |
| KR20230156824A (ko) | 2021-03-12 | 2023-11-14 | 꼰세르 엣세.삐.아. | 2개의 스테이지들에서 디알킬 말리에이트를 수소화함으로써 디알킬 숙시네이트 및 1,4-부탄디올의 공생산을 위한 공정 |
| CN116102425A (zh) * | 2023-01-09 | 2023-05-12 | 惠州博科环保新材料有限公司 | 一种延长加氢催化剂寿命的丁二酸二烷基酯加氢方法 |
| US12497372B2 (en) | 2023-03-21 | 2025-12-16 | SipChem Sahara International Petrochemical Company JSC | Oxygenated hydrocarbon production system with acidic impurity removal resin column |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2638481A (en) | 1950-05-26 | 1953-05-12 | Hercules Powder Co Ltd | Maleic acid manufacture |
| GB727828A (en) | 1952-12-09 | 1955-04-06 | Chempatents Inc | Recovery of polycarboxylic acid anhydrides |
| GB763339A (en) | 1953-03-23 | 1956-12-12 | Chempatents Inc | Improvements in recovery of maleic and phthalic acid anhydrides |
| FR1089012A (fr) | 1953-10-08 | 1955-03-14 | Chempatents | Procédé de récupération des anhydrides d'acides polycarboxyliques à partir de mélanges gazeux dilués |
| BE547079A (enExample) | 1955-04-20 | |||
| US2893924A (en) | 1956-04-17 | 1959-07-07 | Saint Gobain | Separation and purification of anhydrides of organic diacids |
| US3040059A (en) | 1959-07-02 | 1962-06-19 | Foster Wheeler Corp | Recovery of the anhydrides of polycarboxylic acids |
| BE792879A (fr) | 1971-12-17 | 1973-03-30 | Chevron Res | Procede d'isolement de l'anhydride maleique |
| US3891680A (en) | 1972-11-29 | 1975-06-24 | Chevron Res | Maleic anhydride recovery using nonaqueous medium |
| US3850758A (en) | 1973-07-02 | 1974-11-26 | Allied Chem | Purification of crude maleic anhydride by treatment with dimethylbenzophenone |
| DE2444824A1 (de) | 1974-09-19 | 1976-04-08 | Basf Ag | Verfahren zur gewinnung von maleinsaeureanhydrid |
| US4071540A (en) | 1976-07-08 | 1978-01-31 | Chevron Research Company | Anhydride separation process |
| US4118403A (en) | 1976-11-18 | 1978-10-03 | Monsanto Company | Recovery of maleic anhydride |
| GB8331793D0 (en) | 1983-11-29 | 1984-01-04 | Davy Mckee Ltd | Process |
| BR8507068A (pt) | 1984-11-21 | 1987-07-14 | Davy Mckee London | Processo para a producao de butano-1,4-diol |
| GB8514002D0 (en) | 1985-06-04 | 1985-07-10 | Davy Mckee Ltd | Process |
| GB8618888D0 (en) | 1986-08-01 | 1986-09-10 | Davy Mckee Ltd | Process |
| WO1988000937A1 (en) * | 1986-08-01 | 1988-02-11 | Davy Mckee (London) Limited | Process for the co-production of butane-1,4-diol and gamma-butyrolactone |
| GB8618890D0 (en) | 1986-08-01 | 1986-09-10 | Davy Mckee Ltd | Process |
| GB8717993D0 (en) | 1987-07-29 | 1987-09-03 | Davy Mckee Ltd | Process |
| GB8717992D0 (en) | 1987-07-29 | 1987-09-03 | Davy Mckee Ltd | Process |
| US4932104A (en) | 1988-09-30 | 1990-06-12 | Adolf Kowal | Separable buckle |
| JP2596604B2 (ja) | 1988-12-14 | 1997-04-02 | 東燃株式会社 | １，４−ブタンジオールおよびテトラヒドロフランの製造方法 |
| BR9007038A (pt) | 1989-01-17 | 1991-11-12 | Davy Mckee London | Processo e aparelho |
| GB8917864D0 (en) | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
| GB8917859D0 (en) | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
| GB8917862D0 (en) | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
| US5347021A (en) | 1990-04-16 | 1994-09-13 | Isp Investments Inc. | Process of vapor phase catalytic hydrogenation of maleic anhydride to gamma-butyrolactone in high conversion and high selectivity using an activated catalyst |
| ZA973972B (en) * | 1996-05-14 | 1998-03-23 | Kvaerner Process Tech Ltd | A process for the production of at least one C4 compound selected from butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran. |
| ZA973971B (en) * | 1996-05-15 | 1998-03-23 | Kvaerner Process Tech Ltd | A process for the production of at least one C4 compound selected from butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran. |
-
1998
- 1998-03-23 DE DE69800886T patent/DE69800886T2/de not_active Expired - Lifetime
- 1998-03-23 EP EP98302163A patent/EP0962438B1/en not_active Expired - Lifetime
- 1998-03-23 ES ES98302163T patent/ES2158645T3/es not_active Expired - Lifetime
-
1999
- 1999-03-19 CA CA002325499A patent/CA2325499A1/en not_active Abandoned
- 1999-03-19 WO PCT/GB1999/000881 patent/WO1999048852A1/en not_active Ceased
- 1999-03-19 BR BR9908993-9A patent/BR9908993A/pt not_active IP Right Cessation
- 1999-03-19 CN CNB998042544A patent/CN1158233C/zh not_active Expired - Fee Related
- 1999-03-19 US US09/555,015 patent/US6274743B1/en not_active Expired - Lifetime
- 1999-03-19 AU AU31560/99A patent/AU751399B2/en not_active Ceased
- 1999-03-19 JP JP2000537838A patent/JP2002507587A/ja active Pending
- 1999-03-19 ID IDW20001103A patent/ID26243A/id unknown
- 1999-03-22 MY MYPI99001067A patent/MY124354A/en unknown
- 1999-03-23 AR ARP990101263A patent/AR015737A1/es unknown
- 1999-05-04 TW TW088107239A patent/TW557294B/zh not_active IP Right Cessation
- 1999-05-30 SA SA99200188A patent/SA99200188B1/ar unknown
-
2000
- 2000-06-12 ZA ZA200002941A patent/ZA200002941B/xx unknown
- 2000-09-20 NO NO20004695A patent/NO20004695D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69800886T2 (de) | 2001-10-11 |
| ZA200002941B (en) | 2001-07-25 |
| AR015737A1 (es) | 2001-05-16 |
| NO20004695L (no) | 2000-09-20 |
| JP2002507587A (ja) | 2002-03-12 |
| TW557294B (en) | 2003-10-11 |
| DE69800886D1 (de) | 2001-07-12 |
| SA99200188B1 (ar) | 2006-11-20 |
| BR9908993A (pt) | 2000-12-12 |
| US6274743B1 (en) | 2001-08-14 |
| ES2158645T3 (es) | 2001-09-01 |
| AU3156099A (en) | 1999-10-18 |
| CA2325499A1 (en) | 1999-09-30 |
| CN1294571A (zh) | 2001-05-09 |
| NO20004695D0 (no) | 2000-09-20 |
| EP0962438B1 (en) | 2001-06-06 |
| WO1999048852A1 (en) | 1999-09-30 |
| MY124354A (en) | 2006-06-30 |
| EP0962438A1 (en) | 1999-12-08 |
| ID26243A (id) | 2000-12-07 |
| CN1158233C (zh) | 2004-07-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6100410A (en) | Process for the production of 1,4-butanediol, γ-butyrolactone and tetrahydrofuran | |
| AU707824B2 (en) | Process for preparing gamma-butyrolactone, butane-1,4-diol and tetrahydrofuran | |
| AU751187B2 (en) | Process for preparing gamma-butyrolactone, butane-1,4-diol and tetrahydrofuran | |
| AU751399B2 (en) | Process for the preparation of butanediol, butyrolactone and tetrahydrofuran | |
| US6204395B1 (en) | Process for the preparation of butane-1,4-diol, γ-butyrolactone and tetrahydrofuran | |
| KR100464609B1 (ko) | 1,4-부탄디올,감마-부티로락톤및테트라하이드로푸란의제조방법 | |
| KR100538479B1 (ko) | 부탄디올, 부티롤락톤, 및 테트라하이드로푸란의 제조 방법 | |
| MXPA00009339A (en) | Process for the preparation of butanediol, butyrolactone and tetrahydrofuran | |
| MXPA00004663A (en) | Process for preparing gamma-butyrolactone, butane-1,4-diol and tetrahydrofuran |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |