SE520985C2 - Förfarande för framställning av ett alkoholderivat - Google Patents

Förfarande för framställning av ett alkoholderivat

Info

Publication number: SE520985C2
Authority: SE; Sweden
Prior art keywords: process according; alcohol; alkyl; oxetane; propanediol
Prior art date: 1998-12-16

Application number

SE9804338A

Other languages

English (en)

Swedish (sv)

Other versions

SE9804338L (sv

SE9804338D0 (sv

Inventor

Ulf Annby

Nicola Rehnberg

Original Assignee

Perstorp Ab

Priority date (The priority date 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 date listed.)

1998-12-16

Filing date

1998-12-16

Publication date

2003-09-16

1998-12-16 Application filed by Perstorp Ab filed Critical Perstorp Ab

1998-12-16 Priority to SE9804338A priority Critical patent/SE520985C2/sv

1998-12-16 Publication of SE9804338D0 publication Critical patent/SE9804338D0/xx

1999-12-06 Priority to JP2000588156A priority patent/JP3759698B2/ja

1999-12-06 Priority to US09/868,031 priority patent/US6515152B1/en

1999-12-06 Priority to AT99964837T priority patent/ATE249447T1/de

1999-12-06 Priority to DE69911251T priority patent/DE69911251T2/de

1999-12-06 Priority to AU30880/00A priority patent/AU3088000A/en

1999-12-06 Priority to ES99964837T priority patent/ES2205931T3/es

1999-12-06 Priority to KR1020017007576A priority patent/KR100643730B1/ko

1999-12-06 Priority to PCT/SE1999/002267 priority patent/WO2000035895A1/en

1999-12-06 Priority to EP99964837A priority patent/EP1140884B1/de

1999-12-06 Priority to CNB998157252A priority patent/CN1144798C/zh

2000-06-17 Publication of SE9804338L publication Critical patent/SE9804338L/xx

2003-09-16 Publication of SE520985C2 publication Critical patent/SE520985C2/sv

Links

150000001298 alcohols Chemical class 0.000 title claims abstract description 7
238000004519 manufacturing process Methods 0.000 title abstract description 4
238000000034 method Methods 0.000 claims abstract description 56
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims abstract description 34
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 33
239000004202 carbamide Substances 0.000 claims abstract description 31
238000006243 chemical reaction Methods 0.000 claims abstract description 26
239000003054 catalyst Substances 0.000 claims abstract description 20
238000000197 pyrolysis Methods 0.000 claims abstract description 10
239000011541 reaction mixture Substances 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
238000004821 distillation Methods 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 30
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 19
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 11
-1 hydroxyalkyloxy Chemical group 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
239000006227 byproduct Substances 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
229920000642 polymer Polymers 0.000 claims description 8
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
150000004703 alkoxides Chemical group 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 6
239000000539 dimer Substances 0.000 claims description 6
125000005027 hydroxyaryl group Chemical group 0.000 claims description 6
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
239000013638 trimer Substances 0.000 claims description 6
229920000166 polytrimethylene carbonate Polymers 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 4
WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 2
PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 2
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
239000012300 argon atmosphere Substances 0.000 claims description 2
239000012298 atmosphere Substances 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
239000012299 nitrogen atmosphere Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 3
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims 2
JHSWSKVODYPNDV-UHFFFAOYSA-N 2,2-bis(prop-2-enoxymethyl)propane-1,3-diol Chemical compound C=CCOCC(CO)(CO)COCC=C JHSWSKVODYPNDV-UHFFFAOYSA-N 0.000 claims 1
LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 claims 1
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims 1
150000000185 1,3-diols Chemical class 0.000 abstract description 3
235000013877 carbamide Nutrition 0.000 abstract 2
230000000977 initiatory effect Effects 0.000 abstract 1
230000001737 promoting effect Effects 0.000 abstract 1
238000005481 NMR spectroscopy Methods 0.000 description 15
238000003756 stirring Methods 0.000 description 12
238000012512 characterization method Methods 0.000 description 8
UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000000376 reactant Substances 0.000 description 7
229920005862 polyol Polymers 0.000 description 6
150000003077 polyols Chemical class 0.000 description 6
DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 4
150000002921 oxetanes Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
125000003003 spiro group Chemical group 0.000 description 4
239000011701 zinc Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
101001047746 Homo sapiens Lamina-associated polypeptide 2, isoform alpha Proteins 0.000 description 2
101001047731 Homo sapiens Lamina-associated polypeptide 2, isoforms beta/gamma Proteins 0.000 description 2
102100023981 Lamina-associated polypeptide 2, isoform alpha Human genes 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
125000003566 oxetanyl group Chemical group 0.000 description 2
PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
SCNCJKBJMHZKSF-UHFFFAOYSA-N [3,9-diethyl-3-(hydroxymethyl)-1,5,7,11-tetraoxaspiro[5.5]undecan-9-yl]methanol Chemical compound O1CC(CC)(CO)COC21OCC(CC)(CO)CO2 SCNCJKBJMHZKSF-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
238000002328 two-dimensional heteronuclear correlation spectroscopy Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SE9804338A 1998-12-16 1998-12-16 Förfarande för framställning av ett alkoholderivat SE520985C2 (sv)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
SE9804338A SE520985C2 (sv)	1998-12-16	1998-12-16	Förfarande för framställning av ett alkoholderivat
CNB998157252A CN1144798C (zh)	1998-12-16	1999-12-06	氧杂环丁烷的制备方法
DE69911251T DE69911251T2 (de)	1998-12-16	1999-12-06	Verfahren zur herstellung eines oxetans
US09/868,031 US6515152B1 (en)	1998-12-16	1999-12-06	Process for production of an oxetane
AT99964837T ATE249447T1 (de)	1998-12-16	1999-12-06	Verfahren zur herstellung eines oxetans
JP2000588156A JP3759698B2 (ja)	1998-12-16	1999-12-06	オキセタンの製造方法
AU30880/00A AU3088000A (en)	1998-12-16	1999-12-06	Process for production of an oxetane
ES99964837T ES2205931T3 (es)	1998-12-16	1999-12-06	Procedimiento para producir un oxetano.
KR1020017007576A KR100643730B1 (ko)	1998-12-16	1999-12-06	옥세탄의 제조방법
PCT/SE1999/002267 WO2000035895A1 (en)	1998-12-16	1999-12-06	Process for production of an oxetane
EP99964837A EP1140884B1 (de)	1998-12-16	1999-12-06	Verfahren zur herstellung eines oxetans

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE9804338A SE520985C2 (sv)	1998-12-16	1998-12-16	Förfarande för framställning av ett alkoholderivat

Publications (3)

Publication Number	Publication Date
SE9804338D0 SE9804338D0 (sv)	1998-12-16
SE9804338L SE9804338L (sv)	2000-06-17
SE520985C2 true SE520985C2 (sv)	2003-09-16

Family

ID=20413670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE9804338A SE520985C2 (sv)	1998-12-16	1998-12-16	Förfarande för framställning av ett alkoholderivat

Country Status (11)

Country	Link
US (1)	US6515152B1 (de)
EP (1)	EP1140884B1 (de)
JP (1)	JP3759698B2 (de)
KR (1)	KR100643730B1 (de)
CN (1)	CN1144798C (de)
AT (1)	ATE249447T1 (de)
AU (1)	AU3088000A (de)
DE (1)	DE69911251T2 (de)
ES (1)	ES2205931T3 (de)
SE (1)	SE520985C2 (de)
WO (1)	WO2000035895A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE525080C2 (sv) *	2003-03-21	2004-11-23	Perstorp Specialty Chem Ab	Förfarande för framställning av en allyleter
US9278966B2 (en)	2011-06-07	2016-03-08	Kureha Corporation	Method for manufacturing oxetane compound, method for manufacturing azolylmethylcyclopentanol compound, and intermediate compound
CN102321097A (zh) *	2011-07-18	2012-01-18	沈阳化工大学	一种螺环原碳酸酯单体的合成方法
US9108911B1 (en)	2014-03-26	2015-08-18	Oxea Bishop Llc	Process for the manufacture of di-TMP
CN106881132B (zh) *	2015-12-15	2020-04-24	中国科学院大连化学物理研究所	一种合成氨的催化剂
KR20220163415A (ko)	2020-04-03	2022-12-09	창저우 트론리 어드벤스드 일렉트로닉 머티어리얼스 컴퍼니, 리미티드	마이크로 반응기를 통해 옥세탄 화합물을 합성하는 방법

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB787406A (en) *	1955-04-20	1957-12-11	Bayer Ag	Process for the manufacture of trimethylene oxide compounds containing hydroxyl groups
JPH07165651A (ja) *	1993-12-14	1995-06-27	Mitsui Toatsu Chem Inc	ジペンタエリスリトールの製造方法
JP3840695B2 (ja) *	1996-06-20	2006-11-01	東亞合成株式会社	水酸基を有するオキセタン化合物の製造方法

1998
- 1998-12-16 SE SE9804338A patent/SE520985C2/sv not_active IP Right Cessation
1999
- 1999-12-06 KR KR1020017007576A patent/KR100643730B1/ko not_active Expired - Fee Related
- 1999-12-06 JP JP2000588156A patent/JP3759698B2/ja not_active Expired - Lifetime
- 1999-12-06 EP EP99964837A patent/EP1140884B1/de not_active Expired - Lifetime
- 1999-12-06 AT AT99964837T patent/ATE249447T1/de not_active IP Right Cessation
- 1999-12-06 WO PCT/SE1999/002267 patent/WO2000035895A1/en not_active Ceased
- 1999-12-06 AU AU30880/00A patent/AU3088000A/en not_active Abandoned
- 1999-12-06 DE DE69911251T patent/DE69911251T2/de not_active Expired - Lifetime
- 1999-12-06 US US09/868,031 patent/US6515152B1/en not_active Expired - Lifetime
- 1999-12-06 ES ES99964837T patent/ES2205931T3/es not_active Expired - Lifetime
- 1999-12-06 CN CNB998157252A patent/CN1144798C/zh not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JP3759698B2 (ja)	2006-03-29
AU3088000A (en)	2000-07-03
WO2000035895A1 (en)	2000-06-22
EP1140884A1 (de)	2001-10-10
DE69911251D1 (de)	2003-10-16
EP1140884B1 (de)	2003-09-10
US6515152B1 (en)	2003-02-04
ES2205931T3 (es)	2004-05-01
ATE249447T1 (de)	2003-09-15
CN1144798C (zh)	2004-04-07
CN1333763A (zh)	2002-01-30
SE9804338L (sv)	2000-06-17
DE69911251T2 (de)	2004-07-01
SE9804338D0 (sv)	1998-12-16
JP2002532484A (ja)	2002-10-02
KR20010093185A (ko)	2001-10-27
KR100643730B1 (ko)	2006-11-10

Legal Events

Date	Code	Title	Description
2019-01-29	NUG	Patent has lapsed

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