JPS58180488A - 多価アルコ−ル誘導体及びその製法 - Google Patents
多価アルコ−ル誘導体及びその製法Info
- Publication number
- JPS58180488A JPS58180488A JP57063959A JP6395982A JPS58180488A JP S58180488 A JPS58180488 A JP S58180488A JP 57063959 A JP57063959 A JP 57063959A JP 6395982 A JP6395982 A JP 6395982A JP S58180488 A JPS58180488 A JP S58180488A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- sorbitol
- formula
- polyhydric alcohol
- xylitol
- 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.)
- Granted
Links
- 150000005846 sugar alcohols Polymers 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 66
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 43
- 239000000600 sorbitol Substances 0.000 claims abstract description 43
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims abstract description 39
- 239000000811 xylitol Substances 0.000 claims abstract description 27
- 229960002675 xylitol Drugs 0.000 claims abstract description 27
- 239000003377 acid catalyst Substances 0.000 claims abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229960002920 sorbitol Drugs 0.000 claims description 47
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000012431 aqueous reaction media Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000004020 conductor Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000005070 ripening Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 230000008034 disappearance Effects 0.000 claims 1
- 150000003839 salts Chemical group 0.000 claims 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 abstract description 20
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 abstract description 18
- 235000010447 xylitol Nutrition 0.000 abstract description 18
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 abstract description 16
- 150000001875 compounds Chemical class 0.000 abstract description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract description 8
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000725 suspension Substances 0.000 abstract description 6
- 239000007864 aqueous solution Substances 0.000 abstract description 5
- 239000000654 additive Substances 0.000 abstract description 4
- 230000000996 additive effect Effects 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 229920005672 polyolefin resin Polymers 0.000 abstract description 2
- QMDPLUNYAOTGEC-RZFFKMDDSA-N C(C)[C@@](C(O)=CC1=CC=CC=C1)(O)[C@@H](O)[C@H](O)[C@H](O)CO Chemical compound C(C)[C@@](C(O)=CC1=CC=CC=C1)(O)[C@@H](O)[C@H](O)[C@H](O)CO QMDPLUNYAOTGEC-RZFFKMDDSA-N 0.000 abstract 1
- 230000007547 defect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- -1 xyl alcohol Chemical compound 0.000 description 12
- HZVFRKSYUGFFEJ-YVECIDJPSA-N (2r,3r,4s,5r)-7-phenylhept-6-ene-1,2,3,4,5,6-hexol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=CC1=CC=CC=C1 HZVFRKSYUGFFEJ-YVECIDJPSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- VKFWQGFYGLIANZ-WOPDTQHZSA-N (2r,3s,4r)-6-phenylhex-5-ene-1,2,3,4,5-pentol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C(O)=CC1=CC=CC=C1 VKFWQGFYGLIANZ-WOPDTQHZSA-N 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000013081 microcrystal Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- QJBBDEZQLAJWDC-XEZLXBQYSA-N (2R,3R,4S,5S)-5-chloro-7-phenylhept-6-ene-1,2,3,4,5,6-hexol Chemical compound Cl[C@@](C(O)=CC1=CC=CC=C1)(O)[C@@H](O)[C@H](O)[C@H](O)CO QJBBDEZQLAJWDC-XEZLXBQYSA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 241000218691 Cupressaceae Species 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 206010015719 Exsanguination Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000234479 Narcissus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007562 laser obscuration time method Methods 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57063959A JPS58180488A (ja) | 1982-04-19 | 1982-04-19 | 多価アルコ−ル誘導体及びその製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57063959A JPS58180488A (ja) | 1982-04-19 | 1982-04-19 | 多価アルコ−ル誘導体及びその製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58180488A true JPS58180488A (ja) | 1983-10-21 |
| JPH0259832B2 JPH0259832B2 (enrdf_load_stackoverflow) | 1990-12-13 |
Family
ID=13244353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57063959A Granted JPS58180488A (ja) | 1982-04-19 | 1982-04-19 | 多価アルコ−ル誘導体及びその製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58180488A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60260501A (ja) * | 1984-06-07 | 1985-12-23 | Shinto Paint Co Ltd | 固型かび防止塗料 |
| US4562265A (en) * | 1979-10-11 | 1985-12-31 | Milliken Research Corporation | Method for producing a di-acetal of sorbitol and an aromatic aldehyde |
| US4996334A (en) * | 1988-02-05 | 1991-02-26 | Mitsubishi Petrochemical Co., Ltd. | Sorbitol derivatives |
| WO1992003439A1 (en) * | 1990-08-27 | 1992-03-05 | New Japan Chemical Co., Ltd. | Method of producing acetals |
| WO1996027597A1 (fr) * | 1995-03-03 | 1996-09-12 | New Japan Chemical Co., Ltd. | Cristal hexagonal de diacetal, agent nucleant renfermant ce cristal hexagonal, composition de resine polyolefinique renfermant ledit cristal hexagonal, articles obtenus par moulage de cette composition, et procede de moulage de ladite composition |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6555696B2 (en) | 2001-03-23 | 2003-04-29 | Milliken & Company | Asymmetric dipolar multi-substituted alditol derivatives, methods of making thereof, and compositions and articles containing same |
| US6548581B2 (en) | 2001-03-23 | 2003-04-15 | Milliken & Company | Asymmetric halogen-alkyl alditol derivatives as nucleators and clarifiers for polyolefins, and polyolefin plastic compositions containing same |
-
1982
- 1982-04-19 JP JP57063959A patent/JPS58180488A/ja active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562265A (en) * | 1979-10-11 | 1985-12-31 | Milliken Research Corporation | Method for producing a di-acetal of sorbitol and an aromatic aldehyde |
| JPS60260501A (ja) * | 1984-06-07 | 1985-12-23 | Shinto Paint Co Ltd | 固型かび防止塗料 |
| US4996334A (en) * | 1988-02-05 | 1991-02-26 | Mitsubishi Petrochemical Co., Ltd. | Sorbitol derivatives |
| WO1992003439A1 (en) * | 1990-08-27 | 1992-03-05 | New Japan Chemical Co., Ltd. | Method of producing acetals |
| WO1996027597A1 (fr) * | 1995-03-03 | 1996-09-12 | New Japan Chemical Co., Ltd. | Cristal hexagonal de diacetal, agent nucleant renfermant ce cristal hexagonal, composition de resine polyolefinique renfermant ledit cristal hexagonal, articles obtenus par moulage de cette composition, et procede de moulage de ladite composition |
| US6043303A (en) * | 1995-03-03 | 2000-03-28 | New Japan Chemical Co. Ltd. | Hexagonal crystals of diacetals, nucleating agent comprising said hexagonal crystal, polyolefin resin composition and molding containing said hexagonal crystals, and method for molding said composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0259832B2 (enrdf_load_stackoverflow) | 1990-12-13 |
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