DE2915216A1 - Verfahren zur herstellung eines gemisches aus 2- und 4-hydroxybenzylalkohol - Google Patents
Verfahren zur herstellung eines gemisches aus 2- und 4-hydroxybenzylalkoholInfo
- Publication number
- DE2915216A1 DE2915216A1 DE19792915216 DE2915216A DE2915216A1 DE 2915216 A1 DE2915216 A1 DE 2915216A1 DE 19792915216 DE19792915216 DE 19792915216 DE 2915216 A DE2915216 A DE 2915216A DE 2915216 A1 DE2915216 A1 DE 2915216A1
- Authority
- DE
- Germany
- Prior art keywords
- polyalkylene
- hydroxybenzyl alcohol
- ether
- phenol
- alcohol
- 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- Withdrawn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
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 title claims description 35
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229920000570 polyether Polymers 0.000 claims description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 229920001281 polyalkylene Polymers 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229920001223 polyethylene glycol Polymers 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 8
- 229920002866 paraformaldehyde Polymers 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003983 crown ethers Chemical class 0.000 claims description 3
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 4
- -1 hydroxybenzyl alcohols Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 2
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- GTAKOUPXIUWZIA-UHFFFAOYSA-N 2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethanol Chemical compound CCOCCOCCOCCOCCO GTAKOUPXIUWZIA-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- GHYUCQLUMXYVRT-UHFFFAOYSA-N 8-[2-[2-[2-(2-quinolin-8-yloxyethoxy)ethoxy]ethoxy]ethoxy]quinoline Chemical compound C1=CN=C2C(OCCOCCOCCOCCOC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 GHYUCQLUMXYVRT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/115—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using acetals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792915216 DE2915216A1 (de) | 1979-04-14 | 1979-04-14 | Verfahren zur herstellung eines gemisches aus 2- und 4-hydroxybenzylalkohol |
| US06/071,428 US4238629A (en) | 1979-04-14 | 1979-08-30 | Process for the preparation of a mixture of 2-and 4-hydroxybenzyl alcohol |
| DE8080101750T DE3060070D1 (en) | 1979-04-14 | 1980-04-02 | Process for the preparation of a mixture of 2-hydroxybenzyl alcohol and 4-hydroxybenzyl alcohol |
| EP80101750A EP0017851B1 (de) | 1979-04-14 | 1980-04-02 | Verfahren zur Herstellung eines Gemisches aus 2- und 4-Hydroxybenzylalkohol |
| JP4631680A JPS55141423A (en) | 1979-04-14 | 1980-04-10 | Manufacture of 22 and 44hydroxyybenzylalcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792915216 DE2915216A1 (de) | 1979-04-14 | 1979-04-14 | Verfahren zur herstellung eines gemisches aus 2- und 4-hydroxybenzylalkohol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2915216A1 true DE2915216A1 (de) | 1980-10-23 |
Family
ID=6068345
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792915216 Withdrawn DE2915216A1 (de) | 1979-04-14 | 1979-04-14 | Verfahren zur herstellung eines gemisches aus 2- und 4-hydroxybenzylalkohol |
| DE8080101750T Expired DE3060070D1 (en) | 1979-04-14 | 1980-04-02 | Process for the preparation of a mixture of 2-hydroxybenzyl alcohol and 4-hydroxybenzyl alcohol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8080101750T Expired DE3060070D1 (en) | 1979-04-14 | 1980-04-02 | Process for the preparation of a mixture of 2-hydroxybenzyl alcohol and 4-hydroxybenzyl alcohol |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4238629A (enExample) |
| EP (1) | EP0017851B1 (enExample) |
| JP (1) | JPS55141423A (enExample) |
| DE (2) | DE2915216A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4351962A (en) * | 1980-07-11 | 1982-09-28 | Rhone Poulenc Inc. | Process for the preparation of hydroxy benzene carboxaldehydes |
| FR2508440B1 (fr) * | 1981-06-25 | 1985-11-08 | Saint Gobain Isover | Procede de preparation d'alcools orthohydroxybenzyliques |
| US5019656A (en) * | 1989-03-04 | 1991-05-28 | Mitsubishi Petrochemical Co., Ltd. | Process for preparing p-hydroxybenzyl alcohol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US526786A (en) * | 1894-10-02 | Otto manasse | ||
| FR1331448A (fr) * | 1962-05-21 | 1963-07-05 | Prod Chim Shell Saint Gobain S | Procédé d'hydroxyalcoylation |
| JPS51125035A (en) * | 1974-10-09 | 1976-11-01 | Shionogi & Co Ltd | New process for preparing 0-hydroxybenzylalcohols |
-
1979
- 1979-04-14 DE DE19792915216 patent/DE2915216A1/de not_active Withdrawn
- 1979-08-30 US US06/071,428 patent/US4238629A/en not_active Expired - Lifetime
-
1980
- 1980-04-02 DE DE8080101750T patent/DE3060070D1/de not_active Expired
- 1980-04-02 EP EP80101750A patent/EP0017851B1/de not_active Expired
- 1980-04-10 JP JP4631680A patent/JPS55141423A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0017851A1 (de) | 1980-10-29 |
| US4238629A (en) | 1980-12-09 |
| JPS6341377B2 (enExample) | 1988-08-17 |
| EP0017851B1 (de) | 1981-11-04 |
| JPS55141423A (en) | 1980-11-05 |
| DE3060070D1 (en) | 1982-01-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60028086T2 (de) | Herstellung von polytrimethylene ether glycol und copolymere davon | |
| DE69914773T2 (de) | Verfahren zur reinigung von 1,3-propandiol | |
| EP1224157A1 (de) | Verfahren zur herstellung von arylalkylethern | |
| EP0150794A2 (de) | Verfahren zur Herstellung von Gemischen aus C6-C10-Fettsäuren | |
| DE3443596A1 (de) | Verfahren zur herstellung von phthalsaeureestern, zur herstellung von phthalsaeureestern verwendbarer katalysator und verfahren zu seiner herstellung | |
| DE2915216A1 (de) | Verfahren zur herstellung eines gemisches aus 2- und 4-hydroxybenzylalkohol | |
| DE2421309C2 (de) | Veresterte Isopropanolamine, Verfahren zu ihrer Herstellung und Verwendung derselben | |
| DE2555366C2 (de) | Verfahren zur Herstellung hochmolekularer Polycarbonate | |
| EP0449918A1 (de) | Verfahren zur verbesserten herstellung von (meth)acrylsäureestern mehrwertiger alkohole (i). | |
| DE3706047A1 (de) | Erdalkalimetallsalze vicinal hydroxy, alkoxy-substituierter c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)6(pfeil abwaerts)-c(pfeil abwaerts)2(pfeil abwaerts)(pfeil abwaerts)2(pfeil abwaerts)-fettsaeuren, verfahren zu ihrer herstellung und ihre verwendung als alkoxylierungskatalysatoren | |
| WO1995013260A1 (de) | Verfahren zur herstellung von gemischen schaumarmer nicht-ionischer tenside mit acetalstruktur | |
| EP0454742A1 (de) | Verfahren zur herstellung von guerbet-alkoholen | |
| EP0158052B1 (de) | Verfahren zur Herstelllung von Polyestern verbesserter Anfärbbarkeit | |
| DE1495397C3 (de) | Verfahren zur Herstellung von hochmolekularen Polyestern der Kohlensäure | |
| DE3420708C1 (de) | Modifizierte Polyethylenglykole | |
| EP0087517B1 (de) | Verfahren zur Herstellung von Polyester- und/oder Polyester-polyether-polyolen | |
| WO1999050213A1 (de) | Verfahren zur herstellung von dialkylethern | |
| EP0489761B1 (de) | Verfahren zur herstellung von salzfreien estern von fettsäuren mit oligoglycerinen bzw. mit anlagerungsprodukten von ethylenoxid und/oder propylenoxid an oligoglycerine | |
| DE2745545A1 (de) | Vulkanisierbare elastomermasse | |
| AT149988B (de) | Verfahren zur Darstellung von höhermolekularen Äthern. | |
| DE2461608C3 (de) | Verfahren zur Herstellung von Kondensationsprodukten aus Phenolen und Acetessigsä u re estern | |
| DE69027190T2 (de) | Herstellung von Polyalkylenglykoläthern | |
| DE1037136B (de) | Verfahren zur Herstellung von polymeren Trimethylenoxydderivaten | |
| DE1795224A1 (de) | Hochmolekulare,lineare aromatische Polyesteramide | |
| DE1495316C (de) | Verfahren zur Herstellung hoch molekularer Polycarbonate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |