SE504282C2 - Process for the preparation of a selectively substituted triol - Google Patents
Process for the preparation of a selectively substituted triolInfo
- Publication number
- SE504282C2 SE504282C2 SE9500206A SE9500206A SE504282C2 SE 504282 C2 SE504282 C2 SE 504282C2 SE 9500206 A SE9500206 A SE 9500206A SE 9500206 A SE9500206 A SE 9500206A SE 504282 C2 SE504282 C2 SE 504282C2
- Authority
- SE
- Sweden
- Prior art keywords
- triol
- formal
- cyclic
- process according
- ethoxylated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 150000004072 triols Chemical class 0.000 title abstract 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims abstract description 42
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000002012 dioxanes Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- BGFBWRWYROQISE-UHFFFAOYSA-N 5-ethyl-1,3-dioxane-5-methanol Chemical compound CCC1(CO)COCOC1 BGFBWRWYROQISE-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
' 504 282 varvid den under (ii) bildade cykliska triolformalen kan reageras med etenoxid el- ler propenoxid till motsvarande etoxylerade eller propoxylerade cykliska triolfor- mal enligt (i). '504 282 wherein the cyclic triol formula formed under (ii) can be reacted with ethylene oxide or propylene oxide to the corresponding ethoxylated or propoxylated cyclic triol form according to (i).
Triolen i den cykliska triolformalen utgörs företrädesvis av trimetylolpropan, tri- metyloletan eller glycerol. Den cykliska triolformalen kan framställas genom reak- tion av triolen med formaldehyd. Reaktionen utföres företrädesvis i närvaro av en sur katalysator såsom svavelsyra, saltsyra, metansulfonsyra eller paratoluensulfon- syra samt vid en temperatur av 20-l50°C, vanligtvis 20-100°C.The triol in the cyclic triol formal is preferably trimethylolpropane, trimethylolethane or glycerol. The cyclic triol formal can be prepared by reacting the triol with formaldehyde. The reaction is preferably carried out in the presence of an acid catalyst such as sulfuric acid, hydrochloric acid, methanesulfonic acid or paratoluenesulfonic acid and at a temperature of 20-150 ° C, usually 20-100 ° C.
Det är ofta lämpligt att reaktionen utföres i närvaro av ett lågkokande lösningsme- del såsom bensen.It is often convenient for the reaction to be carried out in the presence of a low boiling solvent such as benzene.
Normalt anlagras i steg (i) i genomsnitt 2-30 mol etenoxid eller propenoxid till formalens fria hydroxylgrupp.Normally, in step (i), an average of 2-30 moles of ethylene oxide or propylene oxide are deposited to the free hydroxyl group of the form.
Reaktionen i stg (i) går lämpligen till så att etenoxid eller propenoxid leds in i for- malen vilken föreligger i flytande form. Temperaturen under reaktionen är vanligen 100-l80°C, trycket 100-1000 kPa (1-10 bar) och reaktionen utföres företrädesvis i alkalisk miljö, varvid bla. natriumhydroxid eller kaliumhydroxid kan användas som katalysator.The reaction in step (i) is conveniently carried out so that ethylene oxide or propylene oxide is introduced into the form which is in liquid form. The temperature during the reaction is usually 100-180 ° C, the pressure 100-1000 kPa (1-10 bar) and the reaction is preferably carried out in an alkaline environment, whereby i.a. sodium hydroxide or potassium hydroxide can be used as catalyst.
Spaltningen i steg (ii) utföres i sur miljö samt lämpligen under vakuum. Företrä- desvis höjs temperaturen tills bildad formal avgår varpå överskott av polyol avdri- ves och den etoxylerade eller propoxylerade triolen kvarstår. Vakuumet är O-l3,3 kPa (0-100 torr), företrädesvis 0-665 Pa (0-5 torr) och allra helst 0-399 (O-3 torr) Genom att enligt uppfinningen utföra spaltningen i steg (ii) i närvaro av den triol som ingår i den cykliska triolformalen som används i steg (i) når man flera förde- lar. Den allra viktigaste är naturligtvis att en tillfredsställande spaltningsreaktion över huvud taget möjliggörs Eventuellt överskott av triol som avdrivs i steg (ii) kan användas för framställning av den cykliska formalen. Samma cykliska formal bildas i steg (ii) och kan överföras till steg (i). Processen i sin helhet blir därför synnerligen ekonomiskt fördelaktig. De ekonomiska fördelarna förstärks givetvis också av att användningen av en lägre envärd alkohol samt avskiljning och uppar- betning av denna undviks.The cleavage in step (ii) is carried out in an acidic environment and preferably under vacuum. Preferably, the temperature is raised until the formal formed leaves, after which excess polyol is evaporated off and the ethoxylated or propoxylated triol remains. The vacuum is 0-13.3 kPa (0-100 torr), preferably 0-665 Pa (0-5 torr) and most preferably 0-399 (0-3 torr). According to the invention, by carrying out the decomposition in step (ii) of the presence of the triol included in the cyclic triol formula used in step (i) achieves several benefits. The most important is, of course, that a satisfactory cleavage reaction is possible at all. Any excess triol stripped in step (ii) can be used to prepare the cyclic formula. The same cyclic form is formed in step (ii) and can be transferred to step (i). The process as a whole will therefore be extremely economically advantageous. Of course, the economic benefits are also enhanced by avoiding the use of a lower monovalent alcohol and its separation and processing.
Uppfmningen förklaras närmare i anslutning till nedanstående utföringsexempel samt bifogade figur som schematiskt formelmässigt illustrerar de olika stegen i förfarandet enligt uppfinningen utgående från en reaktion mellan TMP och formaldehyd. 504 282 Exempel 1 illustrerar därvid en utföringsform enligt uppfinningen medan exempel 2 avser jämförelseförsök där steg (ii) utförs utanför uppfinningens ram.The invention is explained in more detail in connection with the following exemplary embodiments and the accompanying figure which schematically illustrates in formula form the various steps in the process according to the invention based on a reaction between TMP and formaldehyde. Example 1 illustrates an embodiment according to the invention, while Example 2 relates to comparative experiments where step (ii) is performed outside the scope of the invention.
Exempel I I en reaktor utrustad med omrörare, återloppskondensor och termometer satsades 400 g trimetyolpropan (TMP), 243,2 g 37-procentig formalin, 18 g paratoluensul- fonsyra och 3 lbensen.Example I 400 g of trimethiol propane (TMP), 243.2 g of 37% formalin, 18 g of paratoluenesulphonic acid and 3 l of benzene were charged to a reactor equipped with a stirrer, reflux condenser and thermometer.
Blandningen återloppskokades vid ca lO0°C tills ungeför 209 g vatten hade av- lägsnats. Reaktionsblandningen kyldes sedan och extraherades med 3 x 100 ml 30-procentig vattenlösning av natriumformiat för att avlägsna katalysatorn.The mixture was refluxed at about 100 ° C until about 209 g of water had been removed. The reaction mixture was then cooled and extracted with 3 x 100 ml of 30% aqueous sodium formate solution to remove the catalyst.
Det erhållna organiska skiktet torkades varpå bensenet avlägsnades genom indunstning, Den kvarstående produkten destillerades under vakuum, 381 g av den cykliska for- malen 5-etyl-5-hydroximetyl-1,3-dioxan erhölls, kokpunkt 110-'120°C vid 399 Pa (3 torr), 292 g (2,0 mol) S-etyl-S-hydroximetyl-l,3-dioxan i flytande form satsades i en re- aktor. 14,0 mol etenoxid leddes in i det flytande dioxanderivatet i reaktorn. Tem- peraturen i reaktorn var 150°C och trycket 500 kPa (5 bar). I reaktorn fanns 0,61 g KOH. Den erhållna reaktionsblandningen neutraliserades genom tillsatsav 0,66 g ättiksyra.The resulting organic layer was dried and the benzene was removed by evaporation. The residual product was distilled under vacuum, 381 g of the cyclic formula 5-ethyl-5-hydroxymethyl-1,3-dioxane were obtained, b.p. 110 DEG-120 DEG C. at 399 DEG. Pa (3 torr), 292 g (2.0 mol) of S-ethyl-S-hydroxymethyl-1,3-dioxane in liquid form were charged to a reactor. 14.0 moles of ethylene oxide were introduced into the liquid dioxane derivative in the reactor. The temperature in the reactor was 150 ° C and the pressure was 500 kPa (5 bar). The reactor contained 0.61 g of KOH. The resulting reaction mixture was neutralized by the addition of 0.66 g of acetic acid.
S92 g etoxylat av S-etyl-S-hydroximetyl-l,3-dioxan erhölls, där i genomsnitt 6,9 mol etenoxid anlagrats till den fria hydroxylgruppen.S92 g of ethoxylate of S-ethyl-S-hydroxymethyl-1,3-dioxane was obtained, where an average of 6.9 mol of ethylene oxide was deposited to the free hydroxyl group.
I en reaktionskolv nedsänkt i ett oljebad och försedd med omrörare och termome- ter samt kopplad till kylare, förlag, kylfälla och vakuumpump satsades 599,3 g (1,34 mol) av det etoxylerade dioxanderivatet, 273 g (2,03 mol) TMP och 4,4 g 96 procentig H2SO4, Blandningen sattes under ett vakuum av 133 Pa (1 torr) varpå temperaturen höjdes tills S-etyl-S-hydroximetyl-l,3-dioxan började drivas av.599.3 g (1.34 mol) of the ethoxylated dioxane derivative, 273 g (2.03 mol) of TMP were charged to a reaction flask immersed in an oil bath and equipped with stirrers and thermometers and connected to coolers, feeders, cooling traps and vacuum pumps. and 4.4 g of 96% H 2 SO 4. The mixture was placed under a vacuum of 133 Pa (1 torr) and the temperature was raised until S-ethyl-S-hydroxymethyl-1,3-dioxane began to evaporate.
Trycket bibehölls vid ca 133 Pa och temperaturen i kolven fick stiga till ca 145°C.The pressure was maintained at about 133 Pa and the temperature in the flask was allowed to rise to about 145 ° C.
Reaktionen fick fortgå i 2,4 timmar. Därvid erhålls ca 1,2 mol S-etyl-S-hydroximetyl-l,3-dioxan som destillat. Detta kunde användas vid förnyad etoxylering enligt ovan.The reaction was allowed to proceed for 2.4 hours. About 1.2 mol of S-ethyl-S-hydroxymethyl-1,3-dioxane are obtained as distillate. This could be used in renewed ethoxylation as above.
Därefter neutraliserades reaktionsblandningen. Temperaturen höjdes till 165°C, varvid trycket hölls vid ca 133 Pa, Temperaturen höjdes sedan successivt till ca 504 282 180°C, varvid kvarvarande överskott av TMP destillerade över tillsammans med den mindre del av dioxanderivatet som inte avdestillerades vid det första destilla- tionssteget. Denna TMP kunde användas vid förnyad reaktion med den etoxylerade dioxanen till 5-etyl-5-hydroximetyl-1,3-dioxan.Then the reaction mixture was neutralized. The temperature was raised to 165 ° C, keeping the pressure at about 133 Pa. The temperature was then gradually raised to about 504 282 180 ° C, with the remaining excess of TMP distilled over together with the smaller part of the dioxane derivative which was not distilled off in the first distillation step. . This TMP could be used in the reaction with the ethoxylated dioxane to give 5-ethyl-5-hydroxymethyl-1,3-dioxane.
I reaktionskolven kvarstod 580 g TMP-trietoxylat där etoxylatsubstitutionen ute- slutande fanns på en av OH-grupperna. Produkten innehöll ca 2 % ej avdestillerad TMP.580 g of TMP triethoxylate remained in the reaction flask, where the ethoxylate substitution was exclusively on one of the OH groups. The product contained about 2% non-distilled TMP.
Exempel 2 5 g av det etoxylerade S-etyl-S-hydroximetyl-1,3-dioxanet från exempel 1 löstes i etanol och l-n HCl. Viktförhållandet mellan de tre ingredienserna var 2:1:1.Example 2 5 g of the ethoxylated S-ethyl-S-hydroxymethyl-1,3-dioxane from Example 1 were dissolved in ethanol and 1-n HCl. The weight ratio of the three ingredients was 2: 1: 1.
Blandningen värmdes till 80°C i 4 timmar. Alla flyktiga beståndsdelar avdestillera- des. OH-talet för den erhållna produkten blev 128, dvs praktiskt taget samma som för S-etyl-S-hydroximetyl-LB-dioxanet som har ett OH-tal av 1251 En fullständig spaltning till TMP-trietoxylat hade gett ett OH-tal av ca 3801 Försöket visar att etoxylatet av S-etyl-S-hydroximetyl-l,3-dioxan spaltas i mycket 'liten utsträckning under dessa betingelser.The mixture was heated to 80 ° C for 4 hours. All volatile constituents were distilled off. The OH number of the product obtained was 128, i.e. practically the same as for the S-ethyl-S-hydroxymethyl-LB-dioxane which has an OH number of 1251 A complete cleavage to TMP triethoxylate had given an OH number of approx. The experiment shows that the ethoxylate of S-ethyl-S-hydroxymethyl-1,3-dioxane is decomposed to a very small extent under these conditions.
Uppñnningen är inte begränsad till de visade utföringsformerna, då dessa kan mo- difieras på olika sätt inom uppfinningens ramaThe invention is not limited to the embodiments shown, as these can be modified in different ways within the scope of the invention.
Claims (10)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9500206A SE504282C2 (en) | 1995-01-23 | 1995-01-23 | Process for the preparation of a selectively substituted triol |
| PCT/SE1996/000056 WO1996022956A1 (en) | 1995-01-23 | 1996-01-22 | Selectively hydroxysubstituted triol |
| AU45931/96A AU4593196A (en) | 1995-01-23 | 1996-01-22 | Selectively hydroxysubstituted triol |
| TW85100749A TW318835B (en) | 1995-01-23 | 1996-01-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9500206A SE504282C2 (en) | 1995-01-23 | 1995-01-23 | Process for the preparation of a selectively substituted triol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9500206D0 SE9500206D0 (en) | 1995-01-23 |
| SE9500206L SE9500206L (en) | 1996-07-24 |
| SE504282C2 true SE504282C2 (en) | 1996-12-23 |
Family
ID=20396907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9500206A SE504282C2 (en) | 1995-01-23 | 1995-01-23 | Process for the preparation of a selectively substituted triol |
Country Status (4)
| Country | Link |
|---|---|
| AU (1) | AU4593196A (en) |
| SE (1) | SE504282C2 (en) |
| TW (1) | TW318835B (en) |
| WO (1) | WO1996022956A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE509144C2 (en) * | 1997-04-09 | 1998-12-07 | Perstorp Ab | Shrink reducing agents for cement compositions |
| WO2022082285A1 (en) * | 2020-10-19 | 2022-04-28 | Oxiteno S.A. Indústria E Comércio | Composition, agrochemical formulation, methods for increasing water and nutrient availability and for improving pest control in plants and seeds, and uses of the composition and the agrochemical formulation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3163056D1 (en) * | 1980-06-20 | 1984-05-17 | Goldschmidt Ag Th | Process for the production of polymers with at least one terminal primary hydroxyl group |
| US5135683A (en) * | 1991-03-28 | 1992-08-04 | Arco Chemical Technology, L.P. | Process for producing a deprotected alkoxylated polyol |
-
1995
- 1995-01-23 SE SE9500206A patent/SE504282C2/en not_active IP Right Cessation
-
1996
- 1996-01-22 AU AU45931/96A patent/AU4593196A/en not_active Abandoned
- 1996-01-22 WO PCT/SE1996/000056 patent/WO1996022956A1/en active Application Filing
- 1996-01-23 TW TW85100749A patent/TW318835B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| WO1996022956A1 (en) | 1996-08-01 |
| SE9500206D0 (en) | 1995-01-23 |
| AU4593196A (en) | 1996-08-14 |
| TW318835B (en) | 1997-11-01 |
| SE9500206L (en) | 1996-07-24 |
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