TWI376366B - Conversion of a multihydroxylated-alphatic hydrocarbon or ester thereof to a chlorohydrin - Google Patents
Conversion of a multihydroxylated-alphatic hydrocarbon or ester thereof to a chlorohydrin Download PDFInfo
- Publication number
- TWI376366B TWI376366B TW094124531A TW94124531A TWI376366B TW I376366 B TWI376366 B TW I376366B TW 094124531 A TW094124531 A TW 094124531A TW 94124531 A TW94124531 A TW 94124531A TW I376366 B TWI376366 B TW I376366B
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- ester
- alcohol
- catalyst
- polyhydroxylated
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 86
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 title claims description 85
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 6
- 229930195733 hydrocarbon Natural products 0.000 title claims description 6
- 238000000034 method Methods 0.000 claims abstract description 204
- 239000003054 catalyst Substances 0.000 claims abstract description 111
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 84
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 77
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 74
- 230000036961 partial effect Effects 0.000 claims abstract description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 304
- 235000011187 glycerol Nutrition 0.000 claims description 106
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 99
- 239000000203 mixture Substances 0.000 claims description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
- 239000007789 gas Substances 0.000 claims description 81
- 239000002253 acid Substances 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 238000004519 manufacturing process Methods 0.000 claims description 31
- 235000011054 acetic acid Nutrition 0.000 claims description 30
- -1 alcohol ester Chemical class 0.000 claims description 29
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 26
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 26
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 25
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims description 25
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 24
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 23
- 239000012530 fluid Substances 0.000 claims description 20
- 125000000524 functional group Chemical group 0.000 claims description 20
- 238000002309 gasification Methods 0.000 claims description 20
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 claims description 16
- 150000003945 chlorohydrins Chemical class 0.000 claims description 16
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- 235000021419 vinegar Nutrition 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- 150000001298 alcohols Chemical class 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 13
- 239000000052 vinegar Substances 0.000 claims description 13
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 12
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- CSEWAUGPAQPMDC-UHFFFAOYSA-N 2-(4-aminophenyl)acetic acid Chemical compound NC1=CC=C(CC(O)=O)C=C1 CSEWAUGPAQPMDC-UHFFFAOYSA-N 0.000 claims description 11
- 150000002009 diols Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Chemical class 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- OXOWTLDONRGYOT-UHFFFAOYSA-N 4-(dimethylamino)butanoic acid Chemical compound CN(C)CCCC(O)=O OXOWTLDONRGYOT-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002924 oxiranes Chemical class 0.000 claims description 6
- 229920000573 polyethylene Polymers 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- XWWKSLXUVZVGSP-UHFFFAOYSA-N 6-chlorohexanoic acid Chemical compound OC(=O)CCCCCCl XWWKSLXUVZVGSP-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Polymers 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002596 lactones Chemical class 0.000 claims description 5
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 5
- 229940005605 valeric acid Drugs 0.000 claims description 5
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 235000021355 Stearic acid Nutrition 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 4
- 235000014655 lactic acid Nutrition 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000004584 polyacrylic acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000779 smoke Substances 0.000 claims description 4
- 239000008117 stearic acid Substances 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004348 Glyceryl diacetate Substances 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 238000012217 deletion Methods 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 235000019443 glyceryl diacetate Nutrition 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 claims 2
- YSXDKDWNIPOSMF-UHFFFAOYSA-N 5-chloropentanoic acid Chemical compound OC(=O)CCCCCl YSXDKDWNIPOSMF-UHFFFAOYSA-N 0.000 claims 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 235000013985 cinnamic acid Nutrition 0.000 claims 2
- 229930016911 cinnamic acid Natural products 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims 2
- OQOGEOLRYAOSKO-UHFFFAOYSA-N 1,1-dichloro-1-nitroethane Chemical compound CC(Cl)(Cl)[N+]([O-])=O OQOGEOLRYAOSKO-UHFFFAOYSA-N 0.000 claims 1
- OIFAHDAXIUURLN-UHFFFAOYSA-N 2-(fluoromethyl)oxirane Chemical compound FCC1CO1 OIFAHDAXIUURLN-UHFFFAOYSA-N 0.000 claims 1
- OAKXPRADUXVRHB-UHFFFAOYSA-N 2-[4-(didecylamino)phenyl]acetic acid Chemical compound CCCCCCCCCCN(CCCCCCCCCC)C1=CC=C(CC(O)=O)C=C1 OAKXPRADUXVRHB-UHFFFAOYSA-N 0.000 claims 1
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 claims 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims 1
- 229940006015 4-hydroxybutyric acid Drugs 0.000 claims 1
- PHOJOSOUIAQEDH-UHFFFAOYSA-N 5-hydroxypentanoic acid Chemical compound OCCCCC(O)=O PHOJOSOUIAQEDH-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- ZOFITJLZMNVYQJ-UHFFFAOYSA-N CCCCCCCCCCN(CCCCCCCCCC)CCCC(O)=O Chemical compound CCCCCCCCCCN(CCCCCCCCCC)CCCC(O)=O ZOFITJLZMNVYQJ-UHFFFAOYSA-N 0.000 claims 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 241000208125 Nicotiana Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical group 0.000 claims 1
- XYAUIVRRMJYYHR-UHFFFAOYSA-N acetic acid;propane-1,2,3-triol Chemical compound CC(O)=O.OCC(O)CO XYAUIVRRMJYYHR-UHFFFAOYSA-N 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003575 carbonaceous material Substances 0.000 claims 1
- 230000037430 deletion Effects 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 229940074045 glyceryl distearate Drugs 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 230000000887 hydrating effect Effects 0.000 claims 1
- 238000007689 inspection Methods 0.000 claims 1
- 239000002370 magnesium bicarbonate Substances 0.000 claims 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 claims 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 claims 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims 1
- 239000001095 magnesium carbonate Substances 0.000 claims 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims 1
- 229930189471 penicacid Natural products 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- PSCXFXNEYIHJST-UHFFFAOYSA-N trans-styrilacetic acid Natural products OC(=O)CC=CC1=CC=CC=C1 PSCXFXNEYIHJST-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 62
- 239000000047 product Substances 0.000 abstract description 37
- 239000007858 starting material Substances 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 7
- 229960000583 acetic acid Drugs 0.000 description 28
- 238000012545 processing Methods 0.000 description 19
- 239000003377 acid catalyst Substances 0.000 description 14
- 238000007038 hydrochlorination reaction Methods 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 11
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 11
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 9
- 239000003518 caustics Substances 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
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- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
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- ZHWLPDIRXJCEJY-UHFFFAOYSA-N alpha-hydroxyglycine Chemical compound NC(O)C(O)=O ZHWLPDIRXJCEJY-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
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- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- QRZAKQDHEVVFRX-UHFFFAOYSA-N biphenyl-4-ylacetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1 QRZAKQDHEVVFRX-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
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- 239000006184 cosolvent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- CNLMHVUZVNKYJA-UHFFFAOYSA-N decyl pentanoate Chemical compound CCCCCCCCCCOC(=O)CCCC CNLMHVUZVNKYJA-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000011066 ex-situ storage Methods 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- VEZFHIQRLMBZBS-UHFFFAOYSA-N hexylphosphane;hydrochloride Chemical compound [Cl-].CCCCCC[PH3+] VEZFHIQRLMBZBS-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
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- 239000013067 intermediate product Substances 0.000 description 1
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- NMJORVOYSJLJGU-UHFFFAOYSA-N methane clathrate Chemical compound C.C.C.C.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O NMJORVOYSJLJGU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 235000013336 milk Nutrition 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- NQCBIMOYRRMVNA-UHFFFAOYSA-N propane-1,2,3-triol;hydrochloride Chemical compound Cl.OCC(O)CO NQCBIMOYRRMVNA-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- RGZQGGVFIISIHZ-UHFFFAOYSA-N strontium titanium Chemical compound [Ti].[Sr] RGZQGGVFIISIHZ-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
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- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
-
- 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
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58968304P | 2004-07-21 | 2004-07-21 | |
| US67321005P | 2005-04-19 | 2005-04-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200613254A TW200613254A (en) | 2006-05-01 |
| TWI376366B true TWI376366B (en) | 2012-11-11 |
Family
ID=35276487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094124531A TWI376366B (en) | 2004-07-21 | 2005-07-20 | Conversion of a multihydroxylated-alphatic hydrocarbon or ester thereof to a chlorohydrin |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8088957B2 (enExample) |
| EP (3) | EP1771403B1 (enExample) |
| JP (4) | JP2008507526A (enExample) |
| KR (3) | KR101226291B1 (enExample) |
| CN (1) | CN102516205B (enExample) |
| AT (1) | ATE454370T1 (enExample) |
| DE (1) | DE602005018778D1 (enExample) |
| MY (2) | MY143660A (enExample) |
| TW (1) | TWI376366B (enExample) |
| WO (1) | WO2006020234A1 (enExample) |
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| US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
| EP1682465A1 (en) | 2003-07-15 | 2006-07-26 | GRT, Inc. | Hydrocarbon synthesis |
| US20050171393A1 (en) | 2003-07-15 | 2005-08-04 | Lorkovic Ivan M. | Hydrocarbon synthesis |
| EA200800129A1 (ru) | 2003-11-20 | 2008-04-28 | Солвей (Сосьете Аноним) | Псевдоазеотропная композиция, содержащая дихлорпропанол, и способ ее получения |
| US20060100469A1 (en) | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
| US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
| ITMI20050686A1 (it) * | 2005-04-18 | 2006-10-19 | Aser S R L | Processo per la produzione di alfa, gamma-dicloridrina da glicerina ed acido cloridrico |
| KR20080037618A (ko) * | 2005-05-20 | 2008-04-30 | 솔베이(소시에떼아노님) | 폴리히드록실화 지방족 탄화수소 및 염소화제 간의 반응에의한 클로로히드린 제조 방법 |
| US8173823B2 (en) * | 2005-05-20 | 2012-05-08 | Solvay (Société Anonyme) | Method for making an epoxide |
| WO2007092410A2 (en) | 2006-02-03 | 2007-08-16 | Grt, Inc. | Separation of light gases from halogens |
| KR101368416B1 (ko) | 2006-02-03 | 2014-03-05 | 리액션 35, 엘엘씨 | 천연 가스를 액체 탄화수소로 변환시키는 연속 공정 |
| EP2043984A1 (en) | 2006-06-14 | 2009-04-08 | Solvay S.A. | Crude glycerol-based product, process for its purification and its use in the manufacture of dichloropropanol |
| JP2008001856A (ja) * | 2006-06-26 | 2008-01-10 | Doshisha | バイオディーゼル油の製造方法 |
| WO2008074733A1 (en) * | 2006-12-19 | 2008-06-26 | Akzo Nobel N.V. | Process for the catalytic halogenation of a hydroxylated organic compound |
| US7930651B2 (en) | 2007-01-18 | 2011-04-19 | Research In Motion Limited | Agenda display in an electronic device |
| US20100032617A1 (en) * | 2007-02-20 | 2010-02-11 | Solvay (Societe Anonyme) | Process for manufacturing epichlorohydrin |
| FR2912743B1 (fr) * | 2007-02-20 | 2009-04-24 | Solvay | Procede de fabrication d'epichlorhydrine |
| FR2913421B1 (fr) | 2007-03-07 | 2009-05-15 | Solvay | Procede de fabrication de dichloropropanol. |
| FR2913684B1 (fr) * | 2007-03-14 | 2012-09-14 | Solvay | Procede de fabrication de dichloropropanol |
| CN101657400B (zh) * | 2007-04-12 | 2013-07-03 | 陶氏环球技术公司 | 用于制备氯代醇的方法和设备 |
| WO2008128010A1 (en) | 2007-04-12 | 2008-10-23 | Dow Global Technologies Inc. | Process and apparatus for recovery of dichlorohydrins via codistillation |
| TW200906776A (en) * | 2007-04-12 | 2009-02-16 | Dow Global Technologies Inc | Conversion of a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin |
| WO2008128014A1 (en) * | 2007-04-12 | 2008-10-23 | Dow Global Technologies Inc. | Process and apparatus for vapor phase purification during hydrochlorination of multi-hydroxylated aliphatic hydrocarbon compounds |
| WO2008128005A1 (en) | 2007-04-12 | 2008-10-23 | Dow Global Technologies Inc. | Process and apparatus for reducing heavy byproduct formation during recovery of dichlorohydrins |
| WO2008128004A1 (en) | 2007-04-12 | 2008-10-23 | Dow Global Technologies Inc. | Multi-stage process and apparatus for recovering dichlorohydrins |
| KR20090130123A (ko) * | 2007-04-12 | 2009-12-17 | 다우 글로벌 테크놀로지스 인크. | 다이클로로하이드린의 공비 회수를 위한 방법 및 장치 |
| CN101765574A (zh) | 2007-05-24 | 2010-06-30 | Grt公司 | 使卤化氢可逆性俘获与释放相结合的区域反应器 |
| TW200911740A (en) | 2007-06-01 | 2009-03-16 | Solvay | Process for manufacturing a chlorohydrin |
| TWI500609B (zh) | 2007-06-12 | 2015-09-21 | Solvay | 含有環氧氯丙烷的產品，其製備及其不同應用中的用途 |
| TW200911693A (en) | 2007-06-12 | 2009-03-16 | Solvay | Aqueous composition containing a salt, manufacturing process and use |
| FR2918058A1 (fr) * | 2007-06-28 | 2009-01-02 | Solvay | Produit a base de glycerol, procede pour sa purification et son utilisation dans la fabrication de dichloropropanol |
| JP2010241689A (ja) * | 2007-08-17 | 2010-10-28 | Kashima Chemical Kk | クロロヒドリンの製造方法 |
| WO2009026208A2 (en) | 2007-08-23 | 2009-02-26 | Dow Global Technologies Inc. | Brine purification |
| KR20100044911A (ko) | 2007-08-23 | 2010-04-30 | 다우 글로벌 테크놀로지스 인크. | 산업적 염수의 정제를 위한 방법, 적응된 미생물, 조성물 및 장치 |
| CN101784481B (zh) | 2007-08-23 | 2013-05-01 | 陶氏环球技术公司 | 用于纯化工业盐水的方法和设备 |
| JP4596084B2 (ja) * | 2007-09-28 | 2010-12-08 | ダイソー株式会社 | クロロヒドリン類の製造方法 |
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| US2198600A (en) * | 1936-09-10 | 1940-04-30 | Dow Chemical Co | Glycerol dichlorohydrin |
| DE955233C (de) * | 1954-02-19 | 1957-01-03 | Degussa | Verfahren zur Herstellung von Pentaerythrittrichlorhydrin |
| NL261755A (enExample) * | 1960-04-01 | 1900-01-01 | ||
| JPS62242638A (ja) * | 1986-04-14 | 1987-10-23 | Nisso Yuka Kogyo Kk | 塩素化エ−テル化合物の製造方法 |
| BE1005719A3 (fr) * | 1992-03-17 | 1993-12-28 | Solvay | Procede de production d'epichlorhydrine. |
| US5256727A (en) * | 1992-04-30 | 1993-10-26 | Georgia-Pacific Resins, Inc. | Resins with reduced epichlorohydrin hydrolyzates |
| JPH1112208A (ja) * | 1997-06-24 | 1999-01-19 | Nisso Yuka Kogyo Kk | １，３−ジクロロプロパノールの精製法 |
| BE1011576A3 (fr) | 1997-11-27 | 1999-11-09 | Solvay | Produit a base d'epichlorhydrine et procede de fabrication de ce produit. |
| JP4385487B2 (ja) * | 1999-06-08 | 2009-12-16 | 昭和電工株式会社 | ジクロロプロパノールの製造方法 |
| JP4665309B2 (ja) * | 2000-12-08 | 2011-04-06 | 東ソー株式会社 | 高純度３−クロロ−１−プロパノールの製造方法 |
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| EA200800129A1 (ru) * | 2003-11-20 | 2008-04-28 | Солвей (Сосьете Аноним) | Псевдоазеотропная композиция, содержащая дихлорпропанол, и способ ее получения |
| FR2862644B1 (fr) * | 2003-11-20 | 2007-01-12 | Solvay | Utilisation de ressources renouvelables |
| US7910781B2 (en) * | 2004-07-21 | 2011-03-22 | Dow Global Technologies Llc | Process for the conversion of a crude glycerol, crude mixtures of naturally derived multihydroxylated aliphatic hydrocarbons or esters thereof to a chlorohydrin |
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| JP2015193673A (ja) | 2015-11-05 |
| KR101228260B1 (ko) | 2013-01-31 |
| CN102516205A (zh) | 2012-06-27 |
| EP2181979B1 (en) | 2015-04-22 |
| KR101226291B1 (ko) | 2013-01-25 |
| KR101225402B1 (ko) | 2013-01-23 |
| US20080045728A1 (en) | 2008-02-21 |
| EP1771403B1 (en) | 2010-01-06 |
| DE602005018778D1 (de) | 2010-02-25 |
| JP2012158594A (ja) | 2012-08-23 |
| KR20070034599A (ko) | 2007-03-28 |
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| EP1771403A1 (en) | 2007-04-11 |
| EP2174925B1 (en) | 2014-10-15 |
| KR20100090812A (ko) | 2010-08-17 |
| EP2174925A1 (en) | 2010-04-14 |
| JP2008507526A (ja) | 2008-03-13 |
| KR20100090813A (ko) | 2010-08-17 |
| JP2013136643A (ja) | 2013-07-11 |
| WO2006020234A1 (en) | 2006-02-23 |
| MY164459A (en) | 2017-12-15 |
| US8088957B2 (en) | 2012-01-03 |
| ATE454370T1 (de) | 2010-01-15 |
| JP5647290B2 (ja) | 2014-12-24 |
| EP2181979A1 (en) | 2010-05-05 |
| TW200613254A (en) | 2006-05-01 |
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