JP2008507526A - 多ヒドロキシル化脂肪族炭化水素又はそのエステルのクロロヒドリンへの転化 - Google Patents
多ヒドロキシル化脂肪族炭化水素又はそのエステルのクロロヒドリンへの転化 Download PDFInfo
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- JP2008507526A JP2008507526A JP2007522625A JP2007522625A JP2008507526A JP 2008507526 A JP2008507526 A JP 2008507526A JP 2007522625 A JP2007522625 A JP 2007522625A JP 2007522625 A JP2007522625 A JP 2007522625A JP 2008507526 A JP2008507526 A JP 2008507526A
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- Prior art keywords
- acid
- chlorohydrin
- catalyst
- hydrogen chloride
- ester
- 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.)
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 title claims abstract description 104
- 150000002148 esters Chemical class 0.000 title claims abstract description 104
- 238000006243 chemical reaction Methods 0.000 title claims description 97
- 150000003945 chlorohydrins Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims abstract description 226
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 157
- 230000008569 process Effects 0.000 claims abstract description 150
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 135
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 135
- 239000003054 catalyst Substances 0.000 claims abstract description 121
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims abstract description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 81
- 230000036961 partial effect Effects 0.000 claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 claims abstract description 25
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 261
- 235000011187 glycerol Nutrition 0.000 claims description 98
- 239000000203 mixture Substances 0.000 claims description 92
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 76
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 75
- -1 alkaline earth metal salt Chemical class 0.000 claims description 36
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims description 34
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 32
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 31
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 claims description 30
- 239000007789 gas Substances 0.000 claims description 25
- 125000000524 functional group Chemical group 0.000 claims description 24
- 235000011054 acetic acid Nutrition 0.000 claims description 23
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 22
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 17
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 claims description 16
- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 claims description 16
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 16
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 14
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 14
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
- XWWKSLXUVZVGSP-UHFFFAOYSA-N 6-chlorohexanoic acid Chemical compound OC(=O)CCCCCCl XWWKSLXUVZVGSP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 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
- OXOWTLDONRGYOT-UHFFFAOYSA-N 4-(dimethylamino)butanoic acid Chemical compound CN(C)CCCC(O)=O OXOWTLDONRGYOT-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 150000001735 carboxylic acids Chemical class 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 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 8
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical group OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 claims description 8
- 150000007942 carboxylates Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 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
- 239000002243 precursor Substances 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000002924 oxiranes Chemical class 0.000 claims description 7
- 235000019260 propionic acid Nutrition 0.000 claims description 7
- 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 7
- DYPJJAAKPQKWTM-UHFFFAOYSA-N 2-chloropropane-1,3-diol Chemical compound OCC(Cl)CO DYPJJAAKPQKWTM-UHFFFAOYSA-N 0.000 claims description 6
- YSXDKDWNIPOSMF-UHFFFAOYSA-N 5-chloropentanoic acid Chemical compound OC(=O)CCCCCl YSXDKDWNIPOSMF-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 6
- 235000021355 Stearic acid Nutrition 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 6
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000002314 glycerols Chemical class 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 6
- 229920000573 polyethylene Polymers 0.000 claims description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000008117 stearic acid Substances 0.000 claims description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 5
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000003951 lactams Chemical class 0.000 claims description 5
- 150000002596 lactones Chemical class 0.000 claims description 5
- 239000004584 polyacrylic acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Chemical group 0.000 claims description 4
- UXDDRFCJKNROTO-UHFFFAOYSA-N Glycerol 1,2-diacetate Chemical compound CC(=O)OCC(CO)OC(C)=O UXDDRFCJKNROTO-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 229960002684 aminocaproic acid Drugs 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 229930195733 hydrocarbon Chemical group 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Chemical class 0.000 claims description 4
- 235000013772 propylene glycol Nutrition 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 229910052723 transition metal Chemical group 0.000 claims description 4
- 150000003624 transition metals Chemical group 0.000 claims description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
- 239000003513 alkali Substances 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000001805 chlorine compounds Chemical group 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 4
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 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
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims 2
- 229940006015 4-hydroxybutyric acid Drugs 0.000 claims 2
- PHOJOSOUIAQEDH-UHFFFAOYSA-N 5-hydroxypentanoic acid Chemical compound OCCCCC(O)=O PHOJOSOUIAQEDH-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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
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- 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
- 229940005605 valeric acid Drugs 0.000 claims 2
- KQGHTOZUPICELS-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]acetic acid Chemical compound CN(C)C1=CC=C(CC(O)=O)C=C1 KQGHTOZUPICELS-UHFFFAOYSA-N 0.000 claims 1
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- PVTRUXDNYDEGHN-UHFFFAOYSA-N CN(C)C.CCCC(Cl)=O Chemical compound CN(C)C.CCCC(Cl)=O PVTRUXDNYDEGHN-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- GUAJYQUIMFAYNN-YFOILCSASA-N [(3s,5r,6r,8r,9s,10s,13r,14s,17r)-6-chloro-10-formyl-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C=O)CC[C@@H](C[C@]5(O)[C@H](Cl)C[C@H]4[C@@]3(O)CC2)OC(=O)C)=CC(=O)OC1 GUAJYQUIMFAYNN-YFOILCSASA-N 0.000 claims 1
- KDRNUUNCAZHOOH-UHFFFAOYSA-N acetic acid;3-chloropropane-1,2-diol Chemical compound CC(O)=O.OCC(O)CCl KDRNUUNCAZHOOH-UHFFFAOYSA-N 0.000 claims 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 claims 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
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- 239000000047 product Substances 0.000 abstract description 35
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- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical class CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 5
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- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000004313 potentiometry Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- FODWRUPJCKASBN-UHFFFAOYSA-M tetrabutylazanium;chloride;hydrate Chemical compound O.[Cl-].CCCC[N+](CCCC)(CCCC)CCCC FODWRUPJCKASBN-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Images
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)
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| PCT/US2005/025443 WO2006020234A1 (en) | 2004-07-21 | 2005-07-18 | Conversion of a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin |
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| JP2012063819A Division JP2012158594A (ja) | 2004-07-21 | 2012-03-21 | 多ヒドロキシル化脂肪族炭化水素又はそのエステルのクロロヒドリンへの転化 |
| JP2013081999A Division JP5647290B2 (ja) | 2004-07-21 | 2013-04-10 | 多ヒドロキシル化脂肪族炭化水素又はそのエステルのクロロヒドリンへの転化 |
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| JP2012063819A Withdrawn JP2012158594A (ja) | 2004-07-21 | 2012-03-21 | 多ヒドロキシル化脂肪族炭化水素又はそのエステルのクロロヒドリンへの転化 |
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| JP2008540611A (ja) * | 2005-05-20 | 2008-11-20 | ソルヴェイ(ソシエテ アノニム) | 液相におけるクロロヒドリンの調製方法 |
| JP2008540616A (ja) * | 2005-05-20 | 2008-11-20 | ソルヴェイ(ソシエテ アノニム) | クロロヒドリンの連続製造方法 |
| JP2008540610A (ja) * | 2005-05-20 | 2008-11-20 | ソルヴェイ(ソシエテ アノニム) | ポリヒドロキシ化された脂肪族炭化水素の塩素化によるクロロヒドリンの製造方法 |
| JP2008545641A (ja) * | 2005-05-20 | 2008-12-18 | ソルヴェイ(ソシエテ アノニム) | クロロヒドリンの製造方法 |
| JP2008545640A (ja) * | 2005-05-20 | 2008-12-18 | ソルヴェイ(ソシエテ アノニム) | 有機化合物の製造方法 |
| JP2008545642A (ja) * | 2005-05-20 | 2008-12-18 | ソルヴェイ(ソシエテ アノニム) | 耐腐食性装置内でのクロロヒドリンの調製方法 |
| JP2008540609A (ja) * | 2005-05-20 | 2008-11-20 | ソルヴェイ(ソシエテ アノニム) | ポリヒドロキシ化脂肪族炭化水素から出発するクロロヒドリンの調製方法 |
| JP2012167130A (ja) * | 2005-05-20 | 2012-09-06 | Solvay (Sa) | 有機化合物の製造方法 |
| JP2014156479A (ja) * | 2007-03-14 | 2014-08-28 | Solvay (Sa) | ジクロロプロパノールの製造方法 |
| JP2010523703A (ja) * | 2007-04-12 | 2010-07-15 | ダウ グローバル テクノロジーズ インコーポレイティド | ジクロロヒドリンの共沸回収方法及び装置 |
| JP2011516552A (ja) * | 2008-04-09 | 2011-05-26 | ダウ グローバル テクノロジーズ リミティド ライアビリティ カンパニー | ジクロロヒドリン類の効率的回収のための方法及び装置 |
| JP2011518160A (ja) * | 2008-04-16 | 2011-06-23 | ダウ グローバル テクノロジーズ リミティド ライアビリティ カンパニー | 多ヒドロキシル化脂肪族炭化水素またはそのエステルのクロロヒドリンへの変換 |
| JP2012510977A (ja) * | 2008-12-08 | 2012-05-17 | ソルヴェイ(ソシエテ アノニム) | グリセロール処理方法 |
| JP2013531672A (ja) * | 2010-06-30 | 2013-08-08 | サムスン ファイン ケミカルズ カンパニー リミテッド | クロロヒドリン類組成物の製造方法及びその方法によって製造されたクロロヒドリン類組成物を使用するエピクロロヒドリンの製造方法 |
| JP2013531671A (ja) * | 2010-06-30 | 2013-08-08 | サムスン ファイン ケミカルズ カンパニー リミテッド | クロロヒドリン類組成物の製造方法及びその方法によって製造されたクロロヒドリン類組成物を使用するエピクロロヒドリンの製造方法 |
| JP2013535417A (ja) * | 2010-06-30 | 2013-09-12 | サムスン ファイン ケミカルズ カンパニー リミテッド | クロロヒドリン類の製造方法及びその方法によって製造されたクロロヒドリン類を使用するエピクロロヒドリンの製造方法 |
| JP2013535416A (ja) * | 2010-06-30 | 2013-09-12 | サムスン ファイン ケミカルズ カンパニー リミテッド | クロロヒドリン類の製造方法及びその方法によって製造されたクロロヒドリン類を使用するエピクロロヒドリンの製造方法 |
| JP2013531670A (ja) * | 2010-06-30 | 2013-08-08 | サムスン ファイン ケミカルズ カンパニー リミテッド | クロロヒドリン類組成物の製造方法及びその方法によって製造されたクロロヒドリン類組成物を使用するエピクロロヒドリンの製造方法 |
| JP2013534250A (ja) * | 2010-08-18 | 2013-09-02 | デル マー ファーマスーティカルズ | ジアンヒドロガラクチトール等の置換ヘキシトールの合成方法 |
| JP2017109993A (ja) * | 2015-12-18 | 2017-06-22 | 長春人造樹脂廠股▲分▼有限公司 | ジクロロプロパノールの製造方法 |
| US9850190B2 (en) | 2015-12-18 | 2017-12-26 | Chang Chun Plastics Co., Ltd. | Process for preparing dichloropropanol |
Also Published As
| Publication number | Publication date |
|---|---|
| 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 |
| CN102516205B (zh) | 2016-05-04 |
| MY143660A (en) | 2011-06-30 |
| EP1771403A1 (en) | 2007-04-11 |
| EP2174925B1 (en) | 2014-10-15 |
| KR20100090812A (ko) | 2010-08-17 |
| EP2174925A1 (en) | 2010-04-14 |
| KR20100090813A (ko) | 2010-08-17 |
| JP2013136643A (ja) | 2013-07-11 |
| TWI376366B (en) | 2012-11-11 |
| 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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