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 (enExample) | 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 (enExample) |
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 (fr) * | 1990-08-27 | 1992-03-05 | New Japan Chemical Co., Ltd. | Procede de production de composes d'acetal |
| WO1996027597A1 (en) * | 1995-03-03 | 1996-09-12 | New Japan Chemical Co., Ltd. | Hexagonal diacetal crystal, nucleating agent containing the hexagonal crystal, polyolefin resin composition containing the hexagonal crystal, molded articles of the composition, and process for molding the composition |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
-
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 (fr) * | 1990-08-27 | 1992-03-05 | New Japan Chemical Co., Ltd. | Procede de production de composes d'acetal |
| WO1996027597A1 (en) * | 1995-03-03 | 1996-09-12 | New Japan Chemical Co., Ltd. | Hexagonal diacetal crystal, nucleating agent containing the hexagonal crystal, polyolefin resin composition containing the hexagonal crystal, molded articles of the composition, and process for molding the 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 (enExample) | 1990-12-13 |
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