DE102009047196A1 - Verfahren zur Herstellung von 1,6-Hexandiol - Google Patents
Verfahren zur Herstellung von 1,6-Hexandiol Download PDFInfo
- Publication number
- DE102009047196A1 DE102009047196A1 DE102009047196A DE102009047196A DE102009047196A1 DE 102009047196 A1 DE102009047196 A1 DE 102009047196A1 DE 102009047196 A DE102009047196 A DE 102009047196A DE 102009047196 A DE102009047196 A DE 102009047196A DE 102009047196 A1 DE102009047196 A1 DE 102009047196A1
- Authority
- DE
- Germany
- Prior art keywords
- hexanediol
- distillation
- esters
- ppm
- acid
- 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.)
- Withdrawn
Links
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims description 44
- 238000004821 distillation Methods 0.000 claims description 31
- 238000009835 boiling Methods 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 20
- 150000001735 carboxylic acids Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 34
- 239000001361 adipic acid Substances 0.000 description 17
- 235000011037 adipic acid Nutrition 0.000 description 17
- 238000005984 hydrogenation reaction Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- -1 Ammonium ions Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- YDJZXHZRXDLCEH-UHFFFAOYSA-N methyl 6-hydroxyhexanoate Chemical compound COC(=O)CCCCCO YDJZXHZRXDLCEH-UHFFFAOYSA-N 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003809 water extraction Methods 0.000 description 4
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- CROLBRYGLOVQCD-UHFFFAOYSA-N 6-methoxyhexan-1-ol Chemical compound COCCCCCCO CROLBRYGLOVQCD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-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
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- MJJZTPGTCPUANF-UHFFFAOYSA-N OC(=O)CCCCC(O)=O.CC(=C)C(=O)OCCCCCCO Chemical compound OC(=O)CCCCC(O)=O.CC(=C)C(=O)OCCCCCCO MJJZTPGTCPUANF-UHFFFAOYSA-N 0.000 description 1
- VTVNQCSYBWJJSB-UHFFFAOYSA-N OC(C(=O)OCCCCCCO)CCCC Chemical compound OC(C(=O)OCCCCCCO)CCCC VTVNQCSYBWJJSB-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- WPEOOEIAIFABQP-UHFFFAOYSA-N hexanedioic acid;hexane-1,6-diol Chemical compound OCCCCCCO.OC(=O)CCCCC(O)=O WPEOOEIAIFABQP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 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
- C07C29/74—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009047196A DE102009047196A1 (de) | 2009-11-26 | 2009-11-26 | Verfahren zur Herstellung von 1,6-Hexandiol |
| JP2012540377A JP5693603B2 (ja) | 2009-11-26 | 2010-11-22 | １，６−ヘキサンジオールの製造方法 |
| ES10781500.3T ES2498769T3 (es) | 2009-11-26 | 2010-11-22 | Procedimiento para la producción de 1,6-hexanodiol |
| PCT/EP2010/067881 WO2011064155A1 (de) | 2009-11-26 | 2010-11-22 | Verfahren zur herstellung von 1,6-hexandiol |
| CN201080053138.8A CN102666456B (zh) | 2009-11-26 | 2010-11-22 | 制备1,6-己二醇的方法 |
| EP10781500.3A EP2504301B1 (de) | 2009-11-26 | 2010-11-22 | Verfahren zur herstellung von 1,6-hexandiol |
| US12/952,956 US8124815B2 (en) | 2009-11-26 | 2010-11-23 | Process for preparing 1,6-hexanediol |
| US13/303,857 US8236996B2 (en) | 2009-11-26 | 2011-11-23 | Process for preparing 1,6-hexanediol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009047196A DE102009047196A1 (de) | 2009-11-26 | 2009-11-26 | Verfahren zur Herstellung von 1,6-Hexandiol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102009047196A1 true DE102009047196A1 (de) | 2011-06-01 |
Family
ID=43587401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102009047196A Withdrawn DE102009047196A1 (de) | 2009-11-26 | 2009-11-26 | Verfahren zur Herstellung von 1,6-Hexandiol |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8124815B2 (https=) |
| EP (1) | EP2504301B1 (https=) |
| JP (1) | JP5693603B2 (https=) |
| CN (1) | CN102666456B (https=) |
| DE (1) | DE102009047196A1 (https=) |
| ES (1) | ES2498769T3 (https=) |
| WO (1) | WO2011064155A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112521256B (zh) * | 2019-09-18 | 2024-03-12 | 中国石油化工股份有限公司 | 一种高效分离环己酮和脱除环己醇中杂质的方法 |
| TWI905687B (zh) * | 2023-04-13 | 2025-11-21 | 日商Ｄｉｃ股份有限公司 | 六亞甲基(甲基)丙烯酸酯組成物、活性能量線硬化型樹脂組成物、硬化物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10112117A1 (de) | 2001-03-14 | 2002-09-19 | Basf Ag | Verfahren zur Herstellung von Polyalkoholen mit definiertem CPR-Wert |
| DE10112114A1 (de) | 2001-03-14 | 2002-10-02 | Vossloh Schwabe Elektronik | Steuereinrichtung für eine Beleuchtungseinrichtung |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03294327A (ja) * | 1990-04-13 | 1991-12-25 | Dai Ichi Kogyo Seiyaku Co Ltd | 貯蔵安定性の良好な末端イソシアネート基含有ウレタンプレポリマーの製造法 |
| JPH082811B2 (ja) * | 1990-11-30 | 1996-01-17 | 宇部興産株式会社 | １，６―ヘキサンジオールの精製方法 |
| JP3217538B2 (ja) * | 1993-05-21 | 2001-10-09 | 株式会社日本触媒 | １，６−ヘキサンジオールの製造方法 |
| DE59703470D1 (de) * | 1996-03-01 | 2001-06-07 | Basf Ag | Verfahren zur herstellung von 1,6-hexandiol mit einer reinheit über 99 % |
| DE19750532A1 (de) * | 1997-11-14 | 1999-05-20 | Basf Ag | Verfahren zur Herstellung von 1,6-Hexandiol und 6-Hydroxycapronsäure bzw. deren Estern |
| JP2001097904A (ja) * | 1999-09-27 | 2001-04-10 | Mitsubishi Chemicals Corp | １，６−ヘキサンジオールの製造方法 |
| AU1055701A (en) * | 1999-11-05 | 2001-06-06 | Asahi Kasei Kabushiki Kaisha | Process for the preparation of diol mixtures |
| DE102004033557A1 (de) * | 2004-07-09 | 2006-02-16 | Basf Ag | Verfahren zur Herstellung von 1,6-Hexandiol in einer Reinheit von über 99,5% |
| MY148576A (en) | 2007-12-21 | 2013-04-30 | Basf Se | Process for preparing epsilon-caprolactone |
| KR20110110359A (ko) | 2009-01-28 | 2011-10-06 | 바스프 에스이 | 순수 시클로도데칸온의 제조 방법 |
| SG174379A1 (en) | 2009-04-08 | 2011-10-28 | Basf Se | Method for producing 1,6-hexanediol by hydrogenation of oligo- and polyesters |
-
2009
- 2009-11-26 DE DE102009047196A patent/DE102009047196A1/de not_active Withdrawn
-
2010
- 2010-11-22 WO PCT/EP2010/067881 patent/WO2011064155A1/de not_active Ceased
- 2010-11-22 EP EP10781500.3A patent/EP2504301B1/de active Active
- 2010-11-22 CN CN201080053138.8A patent/CN102666456B/zh not_active Expired - Fee Related
- 2010-11-22 ES ES10781500.3T patent/ES2498769T3/es active Active
- 2010-11-22 JP JP2012540377A patent/JP5693603B2/ja not_active Expired - Fee Related
- 2010-11-23 US US12/952,956 patent/US8124815B2/en active Active
-
2011
- 2011-11-23 US US13/303,857 patent/US8236996B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10112117A1 (de) | 2001-03-14 | 2002-09-19 | Basf Ag | Verfahren zur Herstellung von Polyalkoholen mit definiertem CPR-Wert |
| DE10112114A1 (de) | 2001-03-14 | 2002-10-02 | Vossloh Schwabe Elektronik | Steuereinrichtung für eine Beleuchtungseinrichtung |
Non-Patent Citations (1)
| Title |
|---|
| JIS (Japan Industrial Standard) K 1557-1970 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110124925A1 (en) | 2011-05-26 |
| JP2013512210A (ja) | 2013-04-11 |
| EP2504301A1 (de) | 2012-10-03 |
| EP2504301B1 (de) | 2014-07-02 |
| CN102666456B (zh) | 2015-05-13 |
| WO2011064155A1 (de) | 2011-06-03 |
| US20120071624A1 (en) | 2012-03-22 |
| CN102666456A (zh) | 2012-09-12 |
| JP5693603B2 (ja) | 2015-04-01 |
| US8124815B2 (en) | 2012-02-28 |
| US8236996B2 (en) | 2012-08-07 |
| ES2498769T3 (es) | 2014-09-25 |
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| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
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