NO328177B1 - Integrert prosess for fremstilling av epoksyder - Google Patents

Integrert prosess for fremstilling av epoksyder Download PDF

Info

Publication number: NO328177B1
Authority: NO; Norway
Prior art keywords: set forth; reaction; stated; solvent; olefin
Prior art date: 2000-08-11

Application number

NO20021698A

Other languages

English (en)

Norwegian (no)

Other versions

NO20021698D0 (no

NO20021698L (no

Inventor

Aloisio Rino D

Giuseppe Paparatto

Anna Forlin

Giordano De Alberti

Paolo Tegon

Original Assignee

Polimeri Europa Spa

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.)

2000-08-11

Filing date

2002-04-10

Publication date

2009-12-28

2002-04-10 Application filed by Polimeri Europa Spa filed Critical Polimeri Europa Spa

2002-04-10 Publication of NO20021698D0 publication Critical patent/NO20021698D0/no

2002-06-11 Publication of NO20021698L publication Critical patent/NO20021698L/no

2009-12-28 Publication of NO328177B1 publication Critical patent/NO328177B1/no

Links

150000002118 epoxides Chemical class 0.000 title claims abstract 8
238000004519 manufacturing process Methods 0.000 title description 19
238000000034 method Methods 0.000 claims abstract description 149
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 147
150000001336 alkenes Chemical class 0.000 claims abstract description 70
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 65
239000002904 solvent Substances 0.000 claims abstract description 64
239000003054 catalyst Substances 0.000 claims abstract description 51
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 43
239000001301 oxygen Substances 0.000 claims abstract description 43
229910052760 oxygen Inorganic materials 0.000 claims abstract description 43
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 40
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
238000006735 epoxidation reaction Methods 0.000 claims abstract description 34
239000001257 hydrogen Substances 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
239000011261 inert gas Substances 0.000 claims abstract description 25
229910052763 palladium Inorganic materials 0.000 claims abstract description 20
229910052697 platinum Inorganic materials 0.000 claims abstract description 18
239000011541 reaction mixture Substances 0.000 claims abstract description 13
239000006172 buffering agent Substances 0.000 claims abstract description 11
230000001476 alcoholic effect Effects 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 7
239000007810 chemical reaction solvent Substances 0.000 claims abstract description 5
238000000926 separation method Methods 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 83
238000006243 chemical reaction Methods 0.000 claims description 62
239000007788 liquid Substances 0.000 claims description 52
239000000047 product Substances 0.000 claims description 50
239000000203 mixture Substances 0.000 claims description 44
239000007789 gas Substances 0.000 claims description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
238000004821 distillation Methods 0.000 claims description 32
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
238000003786 synthesis reaction Methods 0.000 claims description 20
-1 halogen ions Chemical class 0.000 claims description 19
239000010936 titanium Substances 0.000 claims description 19
229910052719 titanium Inorganic materials 0.000 claims description 19
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 18
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 18
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 18
239000012429 reaction media Substances 0.000 claims description 17
239000007791 liquid phase Substances 0.000 claims description 16
239000012071 phase Substances 0.000 claims description 14
150000001298 alcohols Chemical class 0.000 claims description 12
239000006227 byproduct Substances 0.000 claims description 12
239000002609 medium Substances 0.000 claims description 12
238000009833 condensation Methods 0.000 claims description 11
230000005494 condensation Effects 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
238000007254 oxidation reaction Methods 0.000 claims description 9
239000012808 vapor phase Substances 0.000 claims description 9
150000002739 metals Chemical class 0.000 claims description 8
230000003647 oxidation Effects 0.000 claims description 8
238000003776 cleavage reaction Methods 0.000 claims description 7
238000000746 purification Methods 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
241000196324 Embryophyta Species 0.000 claims description 5
238000010924 continuous production Methods 0.000 claims description 5
238000001914 filtration Methods 0.000 claims description 5
239000001294 propane Substances 0.000 claims description 5
VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 claims description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
230000000295 complement effect Effects 0.000 claims description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 4
239000006185 dispersion Substances 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
230000007017 scission Effects 0.000 claims description 4
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
239000005695 Ammonium acetate Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
235000019257 ammonium acetate Nutrition 0.000 claims description 3
229940043376 ammonium acetate Drugs 0.000 claims description 3
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 3
150000001722 carbon compounds Chemical class 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
238000011010 flushing procedure Methods 0.000 claims description 3
239000012263 liquid product Substances 0.000 claims description 3
239000008188 pellet Substances 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
229920005989 resin Polymers 0.000 claims description 3
239000011347 resin Substances 0.000 claims description 3
239000000377 silicon dioxide Substances 0.000 claims description 3
150000003457 sulfones Chemical class 0.000 claims description 3
239000010457 zeolite Substances 0.000 claims description 3
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 2
ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 2
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
235000013162 Cocos nucifera Nutrition 0.000 claims description 2
244000060011 Cocos nucifera Species 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
229910052786 argon Inorganic materials 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
229910052796 boron Inorganic materials 0.000 claims description 2
150000001649 bromium compounds Chemical class 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
229910052681 coesite Inorganic materials 0.000 claims description 2
229910052906 cristobalite Inorganic materials 0.000 claims description 2
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 2
239000004913 cyclooctene Substances 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
125000001033 ether group Chemical group 0.000 claims description 2
229910052733 gallium Inorganic materials 0.000 claims description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
229910052737 gold Inorganic materials 0.000 claims description 2
239000010931 gold Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000001307 helium Substances 0.000 claims description 2
229910052734 helium Inorganic materials 0.000 claims description 2
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
238000005470 impregnation Methods 0.000 claims description 2
239000012535 impurity Substances 0.000 claims description 2
229910052741 iridium Inorganic materials 0.000 claims description 2
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
239000003446 ligand Substances 0.000 claims description 2
239000003077 lignite Substances 0.000 claims description 2
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims description 2
239000004005 microsphere Substances 0.000 claims description 2
150000007522 mineralic acids Chemical group 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
239000003415 peat Substances 0.000 claims description 2
125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
238000001556 precipitation Methods 0.000 claims description 2
239000002994 raw material Substances 0.000 claims description 2
229910052703 rhodium Inorganic materials 0.000 claims description 2
239000010948 rhodium Substances 0.000 claims description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
235000012239 silicon dioxide Nutrition 0.000 claims description 2
238000004230 steam cracking Methods 0.000 claims description 2
229910052682 stishovite Inorganic materials 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
229910052905 tridymite Inorganic materials 0.000 claims description 2
239000002023 wood Substances 0.000 claims description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
238000005336 cracking Methods 0.000 claims 2
150000002825 nitriles Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
150000003573 thiols Chemical class 0.000 claims 1
238000007865 diluting Methods 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 17
150000002924 oxiranes Chemical class 0.000 description 8
230000003197 catalytic effect Effects 0.000 description 7
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 5
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
235000002639 sodium chloride Nutrition 0.000 description 4
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 3
239000002360 explosive Substances 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000002638 heterogeneous catalyst Substances 0.000 description 2
150000002432 hydroperoxides Chemical class 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
150000003333 secondary alcohols Chemical class 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000002699 waste material Substances 0.000 description 2
BVEIKFLZWBDLJG-UHFFFAOYSA-N 1-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCC BVEIKFLZWBDLJG-UHFFFAOYSA-N 0.000 description 1
HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 description 1
WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
QMGLMRPHOITLSN-UHFFFAOYSA-N 2,4-dimethyloxolane Chemical compound CC1COC(C)C1 QMGLMRPHOITLSN-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical class [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 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
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
229920005830 Polyurethane Foam Polymers 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000004880 explosion Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011496 polyurethane foam Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000006833 reintegration Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 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
229940048086 sodium pyrophosphate Drugs 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
- C01B15/01—Hydrogen peroxide
- C01B15/029—Preparation from hydrogen and oxygen
- 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
- Y02P20/10—Process efficiency

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Epoxy Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Epoxy Resins (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO20021698A 2000-08-11 2002-04-10 Integrert prosess for fremstilling av epoksyder NO328177B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2000MI001883A IT1318681B1 (it)	2000-08-11	2000-08-11	Procedimento integrato per la preparazione di epossidi.
PCT/EP2001/009034 WO2002014297A1 (en)	2000-08-11	2001-08-03	Integrated process for the preparation of epoxides

Publications (3)

Publication Number	Publication Date
NO20021698D0 NO20021698D0 (no)	2002-04-10
NO20021698L NO20021698L (no)	2002-06-11
NO328177B1 true NO328177B1 (no)	2009-12-28

Family

ID=11445715

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20021698A NO328177B1 (no)	2000-08-11	2002-04-10	Integrert prosess for fremstilling av epoksyder

Country Status (13)

Country	Link
US (1)	US6541648B1 (de)
EP (1)	EP1307434B1 (de)
JP (1)	JP5047444B2 (de)
KR (1)	KR100830278B1 (de)
CN (1)	CN1388805A (de)
AT (1)	ATE349437T1 (de)
AU (1)	AU2001291736A1 (de)
CA (1)	CA2387083C (de)
DE (1)	DE60125548T2 (de)
ES (1)	ES2277942T3 (de)
IT (1)	IT1318681B1 (de)
NO (1)	NO328177B1 (de)
WO (1)	WO2002014297A1 (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1318682B1 (it) *	2000-08-11	2003-08-27	Enichem Spa	Procedimento integrato per la preparazione di ossidi olefinici.
EP1403259A1 (de) *	2002-09-30	2004-03-31	Degussa AG	Verfahren zur Epoxidierung von Olefinen
KR100495335B1 (ko) *	2002-11-15	2005-06-14	주식회사 엘지화학	스팀의 직접접촉을 이용한 고분자 회수방법
EP1424331A1 (de) *	2002-11-26	2004-06-02	Degussa AG	Verfahren zur Epoxidierung von Olefinen
EP1489074A1 (de) *	2003-06-18	2004-12-22	Degussa AG	Verfahren zur Epoxidierung von Propen
US6878836B2 (en)	2003-06-18	2005-04-12	Degussa Ag	Process for the epoxidation of propene
DE602004018510D1 (de) *	2003-08-19	2009-01-29	Shell Int Research	Verfahren zur herstellung von alkylenoxid
US6867312B1 (en) *	2004-03-17	2005-03-15	Arco Chemical Technology, L.P.	Propylene oxide process
US7501532B1 (en) *	2007-11-20	2009-03-10	Lyondell Chemical Technology, L.P.	Process for producing hydrogen peroxide
EP2103604A1 (de) *	2008-03-17	2009-09-23	Evonik Degussa GmbH	Verfahren zur Herstellung von Epichlorhydrin
EP2149570A1 (de) *	2008-08-01	2010-02-03	Hexion Specialty Chemicals Research Belgium S.A.	Verfahren zur Herstellung von Epichlorhydrin mit Wasserstoffperoxid und einem Mangankomplex
EP2149569A1 (de)	2008-08-01	2010-02-03	Hexion Specialty Chemicals Research Belgium S.A.	Verfahren zur Herstellung eines 1,2-Epoxid
EP2516409B1 (de) *	2009-12-21	2017-01-25	Blue Cube IP LLC	Verfahren zur herstellung von divinylarendioxiden
RU2663775C2 (ru) *	2013-10-02	2018-08-09	Солвей Са	Способ получения очищенного водного раствора пероксида водорода
EP3406603A1 (de) *	2017-05-22	2018-11-28	Evonik Degussa GmbH	Verfahren zur epoxidierung von propen
KR102306544B1 (ko)	2017-09-07	2021-09-30	주식회사 엘지화학	에스터화 반응에서의 1가 알코올의 제거 방법 및 이를 포함하는 에스터 조성물의 제조 방법
CN110339860B (zh) *	2019-07-29	2022-03-01	湖北工程学院	交联降冰片烯共聚物复合炭黑三维网络固载铂纳米催化剂及其制备方法和应用
CN113735800A (zh) *	2021-09-26	2021-12-03	华东理工大学	一种丙烯气相直接环氧化法制备环氧丙烷的反应工艺

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4772458A (en) *	1986-11-19	1988-09-20	E. I. Du Pont De Nemours And Company	Catalytic process for making hydrogen peroxide from hydrogen and oxygen employing a bromide promoter
US5194242A (en) *	1990-09-11	1993-03-16	E. I. Du Pont De Nemours And Company	Process for the production of hydrogen peroxide from hydrogen and oxygen
DE69732739T2 (de)	1996-06-14	2006-04-06	Sumitomo Chemical Co. Ltd.	Verfahren zur Herstellung von epoxidierten Olefineprodukten
IT1301999B1 (it) *	1998-08-05	2000-07-20	Enichem Spa	Catalizzatore, processo per la produzione di acqua ossigenata esuo impiego in processi di ossidazione.
DE19857137A1 (de) *	1998-12-11	2000-06-15	Bayer Ag	Integriertes Verfahren zur Herstellung von Epoxiden aus Olefinen
IT1313572B1 (it) *	1999-07-27	2002-09-09	Enichem Spa	Procedimento per la preparazione di epossidi.
IT1318682B1 (it) *	2000-08-11	2003-08-27	Enichem Spa	Procedimento integrato per la preparazione di ossidi olefinici.

2000
- 2000-08-11 IT IT2000MI001883A patent/IT1318681B1/it active
2001
- 2001-08-03 KR KR1020027004567A patent/KR100830278B1/ko active IP Right Grant
- 2001-08-03 DE DE60125548T patent/DE60125548T2/de not_active Expired - Lifetime
- 2001-08-03 CN CN01802382A patent/CN1388805A/zh active Pending
- 2001-08-03 EP EP01971869A patent/EP1307434B1/de not_active Expired - Lifetime
- 2001-08-03 WO PCT/EP2001/009034 patent/WO2002014297A1/en active IP Right Grant
- 2001-08-03 ES ES01971869T patent/ES2277942T3/es not_active Expired - Lifetime
- 2001-08-03 CA CA2387083A patent/CA2387083C/en not_active Expired - Lifetime
- 2001-08-03 US US10/088,899 patent/US6541648B1/en not_active Expired - Lifetime
- 2001-08-03 JP JP2002519439A patent/JP5047444B2/ja not_active Expired - Lifetime
- 2001-08-03 AU AU2001291736A patent/AU2001291736A1/en not_active Abandoned
- 2001-08-03 AT AT01971869T patent/ATE349437T1/de not_active IP Right Cessation
2002
- 2002-04-10 NO NO20021698A patent/NO328177B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP1307434A1 (de)	2003-05-07
ATE349437T1 (de)	2007-01-15
CN1388805A (zh)	2003-01-01
NO20021698D0 (no)	2002-04-10
KR20020060194A (ko)	2002-07-16
ITMI20001883A1 (it)	2002-02-11
ITMI20001883A0 (it)	2000-08-11
CA2387083A1 (en)	2002-02-21
ES2277942T3 (es)	2007-08-01
JP5047444B2 (ja)	2012-10-10
DE60125548D1 (de)	2007-02-08
US6541648B1 (en)	2003-04-01
JP2004506626A (ja)	2004-03-04
CA2387083C (en)	2011-10-04
KR100830278B1 (ko)	2008-05-16
AU2001291736A1 (en)	2002-02-25
DE60125548T2 (de)	2007-10-11
WO2002014297A1 (en)	2002-02-21
NO20021698L (no)	2002-06-11
EP1307434B1 (de)	2006-12-27
IT1318681B1 (it)	2003-08-27

Legal Events

Date	Code	Title	Description
2021-09-13	MK1K	Patent expired

Publication	Publication Date	Title
EP1307435B2 (de)	2007-01-10	Integriertes verfahren zur herstellung eines epoxids
KR100835131B1 (ko)	2008-06-09	올레핀계 옥사이드의 연속 제조방법
NO328177B1 (no)	2009-12-28	Integrert prosess for fremstilling av epoksyder
EP0720984B1 (de)	1998-04-22	Integriertes Epoxydationsverfahren
EP2323999B1 (de)	2012-01-04	Verfahren zur herstellung von propylenoxid
NO337335B1 (no)	2016-03-21	Fremgangsmåte for fremstilling av hydrogenperoksyd
JP2013079259A (ja)	2013-05-02	過酸化物化合物を用いたオキシランの製造方法
US7687647B2 (en)	2010-03-30	Propylene oxide process
JP2004525073A (ja)	2004-08-19	オレフィンオキシドの連続製造方法