CN101244990B - Production method for 1-hydroxyethyl-4-oxygen ethyl-hydroxyethyl benzenediether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzenediether - Google Patents
Production method for 1-hydroxyethyl-4-oxygen ethyl-hydroxyethyl benzenediether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzenediether Download PDFInfo
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- CN101244990B CN101244990B CN2008100107268A CN200810010726A CN101244990B CN 101244990 B CN101244990 B CN 101244990B CN 2008100107268 A CN2008100107268 A CN 2008100107268A CN 200810010726 A CN200810010726 A CN 200810010726A CN 101244990 B CN101244990 B CN 101244990B
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- hydroxyethyl
- resorcinol
- oxygen ethyl
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- 239000001301 oxygen Substances 0.000 title claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 239000012263 liquid product Substances 0.000 claims abstract description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 80
- 239000000463 material Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- IQHHLQVUUXLKFL-UHFFFAOYSA-N 2-(2-ethylphenyl)ethanol Chemical compound CCC1=CC=CC=C1CCO IQHHLQVUUXLKFL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002808 molecular sieve Substances 0.000 claims description 9
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- WJEIYVAPNMUNIU-UHFFFAOYSA-N [Na].OC(O)=O Chemical compound [Na].OC(O)=O WJEIYVAPNMUNIU-UHFFFAOYSA-N 0.000 claims description 6
- 235000017550 sodium carbonate Nutrition 0.000 claims description 5
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 4
- 238000011085 pressure filtration Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 2
- 238000012805 post-processing Methods 0.000 claims 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 abstract description 13
- 239000000047 product Substances 0.000 abstract description 13
- 229920002635 polyurethane Polymers 0.000 abstract description 9
- 239000004814 polyurethane Substances 0.000 abstract description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 2
- PTBNHEHHLXZZSX-UHFFFAOYSA-N OCCC1=NNC2=C(C=C1)C=CC=C2.C(C)OCC Chemical compound OCCC1=NNC2=C(C=C1)C=CC=C2.C(C)OCC PTBNHEHHLXZZSX-UHFFFAOYSA-N 0.000 abstract 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 230000008676 import Effects 0.000 description 3
- KJTCSAZPIJBBJC-UHFFFAOYSA-N C(C)C=1C(=C(C=CC1)C(C)O)CCO Chemical compound C(C)C=1C(=C(C=CC1)C(C)O)CCO KJTCSAZPIJBBJC-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- -1 dihydroxy ethyl Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 2
- VKWZWOKLRQWMPC-UHFFFAOYSA-N 1-(2-hydroxybutoxy)butan-2-ol Chemical compound CCC(O)COCC(O)CC VKWZWOKLRQWMPC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for manufacturing 1-etylol-4-oxygen ethyl ether hydroxyethyl benzodiazepine (liquid HQEE) and 1-etylol-3-oxygen ethyl ether hydroxyethyl benzodiazepine (liquid HER), which includes the steps: water is added in a reaction vessel, and hydroquinone or catechol and sodium carbonate are added during the period of mixing; under the protection of nitrogen, ethylene oxide is added when temperature is less than 50 DEG C, and reaction is carried out for 6 to 12h in 1MPa and 60 to 120 DEG C; hydrochloride is used for causing the pH of reaction solution to be 7.0 when temperature is reduced to 40 to 50 DEG C, then pressure is reduced, and distillating and removing water are carried out; 3A molecular sieve is added when 95 percent water is steamed, and distillation is continued until water content is less than 0.1 percent; pressuring and filtering are carried out in 80 DEG C, thus obtaining colorless and transparent liquid product. The method for manufacturing the 1-etylol-4-oxygen ethyl ether hydroxyethyl benzodiazepine (liquid HQEE) and the 1-etylol-3-oxygen ethyl ether hydroxyethyl benzodiazepine (liquid HER) is reasonable and proper in raw material choosing, proportion, and production technique, high in yield of products, high in purity, and good in quality, which can facilitate the operation, reduce the reaction temperature, and adjust the hardness, softness and transparency of the products in the production of downstream polyurethane products.
Description
Technical field
The present invention relates to is the preparation method of aromatic series (polynary) alcohol, particularly uses oxirane and (polynary) phenol prepared in reaction to have the preparation method of aromatic series (polynary) alcohol of ether structure, and wherein Sauerstoffatom one end is connected with carbocyclic ring.
Background technology
The dihydroxy ethyl bis ether of aromatic hydrocarbons all has widely and uses in macromolecular materials such as urethane, polycarbonate, polyester and Synolac synthetic.Particularly HQEE (is the general abbreviation of Hydroquinone bis{2-hydroxyethyl}ether, Chinese by name 1,4-dihydroxyethylbenzenand diether, down with)/or HER (be the abbreviation of Bis{2-hydroxyethyl}ether of resorcinol, Chinese is called 1,3-dihydroxyethylbenzenand diether, down together) in the preparation of polyurethane high molecule compound, be to use more linking agent, can obviously promote the physicochemical property of goods.
The linking agent that is used for urethane is divided into the compound of " amine " and " hydroxyl " two big classes usually.Although their resulting polyurethane products have their own characteristics each because used isocyanic ester () reactive behavior difference for example, TDI or MDI, the linking agent of " amine " class can not with the compatible use of MDI.Greatly faster than TDI, be applicable to " hydroxyl " compound crosslink agent of MDI based on the growth of MDI, be gesture in the ascendant.
The linking agent of " hydroxyl " compound according to structure, can be divided into fat (polynary) alcohol, fragrance (polynary) alcohol and heterocyclic (polynary) alcohol.They are mutually crosslinked with the MDI compatibility separately, obtain the different polyurethane high molecule synthetic materials of performance.
Because HQEE (105 ℃ of MP) and HER (89 ℃ of MP) are solid phase prods at normal temperature, want heating and melting during use, be not convenient for the application that derived product is produced.For the mode of appearance of its HQEE and HER is changed into liquid, carried out in its contained hydroxyethyl, continue to introduce oxygen ethyl (OCH
2CH
2-) exploitation.Be about to original hydroxyethyl ether and become oxygen ethyl-hydroxyethyl ether (OCH
2CH
2OCH
2CH
2OH).So just HQEE and HER outward appearance are changed over liquid.Moreover, because the lengthening of aliphatic hydrocarbon segment makes its compound (prepared material) more become soft.This adjusts the material hardness aspect also for when being applied to polyurethane preparation, and an advantageous conditions may be provided.
Summary of the invention
Target compound of the present invention is from the structure of self, be meant a hydroxyethyl among solid HQEE or the solid HER is proceeded hydroxyethylation and then generated the oxygen ethyl-hydroxyethyl compound, 4-oxygen ethyl-hydroxyethyl-1-hydroxyethylbenzene diether (Hydroquinone 4-oxyethylhydroxyethyl-1-hydroxyethyl ether, abbreviate liquid HQEE as, together following) or 3-oxygen ethyl-hydroxyethyl-1-hydroxyethylbenzene diether (3-oxyethylhydroxyethyl-1-hydroxyethyl ether of resorcinol, abbreviate liquid HER as, down together).
The chemical structure of liquid HQEE and liquid HER is as described below:
These two target compounds, because-OCH
2CH
2Segmental lengthening, the feature that discloses significantly be, the first, changed the appearance attribute of compound, and change into liquid by solid, made things convenient for application in derived product; The second ,-OCH
2CH
2Segmental lengthening makes it (when being used to prepare macromolecular compound) rerum natura soft-hardness that becomes and becomes low.This aspect the adjustment material hardness, provides a comparatively wide range of choice just for when being used for preparing the polyurethane material with " firmly " segment and " soft " segmented structure.
Further understand the feature of these two target compounds, as can be seen, owing to be transformed into the change of this attribute of liquid from solid, having broken usually need be in the restriction of carrying out polyurethane preparation more than 100 ℃---and can carry out under the condition at normal temperature, provide greatly convenient for directly using at the scene at polyurethane elastomer, sealing agent, tackiness agent, coating-forming agent or the like.Conceivable arriving, one directly in the scene in the use of (two-pack) urethane of normal-temperature reaction, re-use with the needs heating and to compare, its superiority is conspicuous.Owing to introduced " soft " segment, these two target compounds in, showed good performance aspect the preparation of the polyurethane product of soft 30～70 (S.A).
These two target compounds are to realize by following chemical reaction:
Issuable side reaction is as shown in the table in the reaction:
Owing in the process that generates target compound, or react simultaneously (for example generate to pay and produce compound 2) or further in-depth reaction (generate to pay and produce compound 1), all be possible.So must select preferential processing condition and in process of production strictness controlled, it is good so just to obtain quality, the target compound that yield is high.
Dihydric phenol need be in alkaline medium in the process of introducing epoxy (alkane) hydrocarbon, through inducing, cause, and then reacts, and present method has selected a kind of alkalescence-yellow soda ash as catalyzer.
The present invention is raw materials used to be: oxyethane, Resorcinol or Resorcinol, catalyzer carbonic acid sodium, molecular sieve etc.Its composition of raw materials is as follows:
Oxyethane and Resorcinol or Resorcinol mol ratio are 3.0～4.0
Water and Resorcinol or Resorcinol weight ratio are 9～11
The mol ratio of catalyzer carbonic acid sodium and Resorcinol or Resorcinol is 0.01～0.20
Dewatering agent is 2～3% of Resorcinol or a Resorcinol weight
Preparation method's technology is divided into reaction and aftertreatment two portions.Reactions steps is: add entry in the reactor of the import and export that have chuck, agitator, condenser, various materials and temperature, pressure indicator etc., stir add down to or Resorcinol, yellow soda ash, in nitrogen medium, add oxyethane in being lower than under 50 ℃ the situation, in 1MPa, 60～120 ℃, reaction 6～12h promptly finishes reaction.Aftertreatment is that to add the pH that hydrochloric acid (30～31%) makes reaction solution when reactant is cooled to 40～50 ℃ be 7.0, underpressure distillation dehydration then, when the water yield steams 95% left and right sides, the 3A molecular sieve can be added wherein, continue distillation moisture, treat that water content is below 0.1% in the material after, carry out pressure filtration in 80 ℃, remove sodium-chlor and molecular sieve in the material, can obtain outward appearance is water white liquid product, i.e. liquid HQEE or liquid HER.
Compared with prior art, no matter the inventive method is material choice, proportioning, or production craft step is all reasonable, proper, and product yield height, purity height, quality are good.The product that production makes is colourless transparent liquid, can be so that have made things convenient for operation in the production of downstream polyurethane products, reduced temperature of reaction, can adjust product " soft durometer ", and transparency of products improves and quality product is improved.
Embodiment
Embodiment 1
In 3.0M
3Stainless steel reaction pot (subsidiary import and export that chuck, agitator, condenser, various materials are arranged and temperature, pressure indicator etc.) add entry 2000Kg, open and stir, add Resorcinol 200Kg, add yellow soda ash 9.6Kg.In nitrogen medium, add oxyethane 252Kg under 50 ℃ the situation in being lower than, again in 1.0MPa, 80～90 ℃, react and promptly finished reaction in 8 hours.Be cooled to 40～50 ℃, add hydrochloric acid (30%) 33.0～35.0Kg, make the PH of reaction (material) liquid, be controlled at 7.0.(under 20 * 133.322Pa) the condition, water is distilled fully in vacuum then in 60～80 ℃.According to practical situation, when approximately the water yield steams 95% left and right sides, the 3A molecular sieve of 6Kg can be added wherein, continue distillation moisture, after treating that water content is below 0.1%, carry out pressure filtration with (equipment that 15 tunic nets are arranged), remove sodium-chlor and molecular sieve in the material in 80 ℃, can obtain outward appearance is water white liquid HQEE396.0Kg (yield is 90.0%), hydroxyl value 465mgKOH/g.
Embodiment 2
In 3.0M
3Stainless steel reaction pot (subsidiary import and export that chuck, agitator, condenser, various materials are arranged and temperature, pressure indicator etc.) add entry 2000Kg, open and stir, add Resorcinol 200Kg, add yellow soda ash 9.6Kg.In nitrogen medium, add oxyethane 252Kg under 50 ℃ the situation in being lower than, again in 1.0MPa, 80～90 ℃, react and promptly finished reaction in 8 hours.Be cooled to 40～50 ℃, add hydrochloric acid (30%) 33.0～35.0Kg, make the PH of reaction (material) liquid, be controlled at 7.0.(under 20 * 133.322Pa) the condition, and water is distilled fully in vacuum then in 60～80 ℃.According to practical situation, when approximately the water yield steams 95% left and right sides, the 3A molecular sieve of 6Kg can be added wherein, continue distillation moisture, after treating that water content is below 0.1%, carry out pressure filtration with (equipment that 15 tunic nets are arranged), remove sodium-chlor and molecular sieve in the material in 80 ℃, can obtain outward appearance is water white liquid HQEE 387.5Kg (yield is 88.0%), hydroxyl value 462mgKOH/g.
Embodiment 3
According to the foregoing description 1, the add-on of oxyethane is risen to 320kg (molecular ratio that is Resorcinol and oxyethane is 1: 4), can obtain outward appearance is water white liquid HQEE 468Kg (yield is 90.0%), hydroxyl value 420mgKOH/g.
Embodiment 4
According to the foregoing description 2, the add-on of oxyethane is risen to 320kg (molecular ratio that is Resorcinol and oxyethane is 1: 4), can obtain outward appearance is water white liquid HER 465Kg (yield is 89.4%), hydroxyl value 425mgKOH/g.
Claims (4)
1.1-hydroxyethyl-4-oxygen ethyl-hydroxyethyl benzene diether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzene diether manufacture method, it is characterized in that it being raw materials usedly to be: oxyethane, Resorcinol or Resorcinol, catalyzer carbonic acid sodium, dewatering agent molecular sieve, its prescription is:
Oxyethane and Resorcinol or Resorcinol mol ratio are 3.0～4.0,
Water and Resorcinol or Resorcinol weight ratio are 9～11,
The mol ratio of catalyzer carbonic acid sodium and Resorcinol or Resorcinol is 0.01～0.20,
The dewatering agent molecular sieve is 2～3% of Resorcinol or a Resorcinol weight;
Preparation method's technology is divided into reaction and aftertreatment two portions:
(1) reaction: add entry in the reactor, stir add down to or Resorcinol, yellow soda ash, in nitrogen medium, add oxyethane in being lower than under 50 ℃ the situation, 1MPa, 60～120 ℃, reaction 6～12h promptly finishes reaction;
(2) aftertreatment: reactant adds concentration when being cooled to 40～50 ℃ be 30～31% hydrochloric acid, the pH that makes reaction solution is 7.0, underpressure distillation dehydration then, when the water yield steams 95% left and right sides, add the dewatering agent molecular sieve, continue distillation moisture, after treating that water content is below 0.1% in the material, carry out pressure filtration in 80 ℃, remove sodium-chlor and molecular sieve in the material, can obtain outward appearance is water white liquid product, i.e. liquid 1-hydroxyethyl-4-oxygen ethyl-hydroxyethyl benzene diether or liquid 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzene diether.
2. according to the described 1-hydroxyethyl of claim 1-4-oxygen ethyl-hydroxyethyl benzene diether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzene diether manufacture method, it is characterized in that in the raw materials used prescription that water and Resorcinol or Resorcinol weight ratio are 10.
3. according to the described 1-hydroxyethyl of claim 1-4-oxygen ethyl-hydroxyethyl benzene diether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzene diether manufacture method, it is characterized in that in the raw materials used prescription, the mol ratio of catalyzer carbonic acid sodium and Resorcinol or Resorcinol is 0.05.
4. according to claim 1,2 or 3 described 1-hydroxyethyl-4-oxygen ethyl-hydroxyethyl benzene diether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzene diether manufacture method, it is characterized in that raw materials used prescription is:
Oxyethane and Resorcinol or Resorcinol mol ratio are 3.0～4.0,
Water and Resorcinol or Resorcinol weight ratio are 10,
The mol ratio of catalyzer carbonic acid sodium and Resorcinol or Resorcinol is 0.05;
The dewatering agent molecular sieve is 2～3% of Resorcinol or a Resorcinol weight;
Pressure in the reactions steps is 1Mpa; In the post-processing step when reactant is cooled to 40～50 ℃ with concentration be 30% hydrochloric acid to make the pH of reaction solution be 7.0, dewatering agent is the 3A molecular sieve.
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|---|---|---|---|
| CN2008100107268A CN101244990B (en) | 2008-03-21 | 2008-03-21 | Production method for 1-hydroxyethyl-4-oxygen ethyl-hydroxyethyl benzenediether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzenediether |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100107268A CN101244990B (en) | 2008-03-21 | 2008-03-21 | Production method for 1-hydroxyethyl-4-oxygen ethyl-hydroxyethyl benzenediether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzenediether |
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| Publication Number | Publication Date |
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| CN101244990B true CN101244990B (en) | 2010-11-10 |
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| CN115850032A (en) * | 2022-11-17 | 2023-03-28 | 沈阳化工研究院有限公司 | Preparation method of hydroquinone dihydroxyethyl ether (HQEE) |
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Assignee: Suzhou Xiangyuan Speical Fine Chemical Co., Ltd. Assignor: Zhou Jian Contract record no.: 2010320001035 Denomination of invention: Production method for 1-hydroxyethyl-4-oxygen ethyl-hydroxyethyl benzenediether and 1-hydroxyethyl-3-oxygen ethyl-hydroxyethyl benzenediether License type: Exclusive License Open date: 20080820 Record date: 20100726 |
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Effective date of registration: 20160928 Address after: Suzhou City, Xiangcheng District province 215138 Jiangsu Yangchenghu town (Hunan City) ten Village Patentee after: Suzhou Xiangyuan Speical Fine Chemical Co., Ltd. Address before: 215138 Yangcheng Lake Town, Xiangcheng District, Suzhou, Jiangsu Patentee before: Zhou Jian |
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Address after: 215138 No. 1 Zhangtangbangxiang, Yangchenghu Town, Xiangcheng District, Suzhou City, Jiangsu Province Patentee after: Suzhou Xiangyuan New Materials Co., Ltd. Address before: Suzhou City, Xiangcheng District province 215138 Jiangsu Yangchenghu town (Hunan City) ten Village Patentee before: Suzhou Xiangyuan Speical Fine Chemical Co., Ltd. |
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