JPS5843142B2 - オレフインケイカゴウブツノカサンカスイソニヨルエポキシカオヨビヒドロキシカニサイシテノシヨクバイノカイシユウホウホウ - Google Patents

オレフインケイカゴウブツノカサンカスイソニヨルエポキシカオヨビヒドロキシカニサイシテノシヨクバイノカイシユウホウホウ

Info

Publication number: JPS5843142B2
Authority: JP; Japan
Prior art keywords: catalyst; reaction; reaction vessel; water; resin
Prior art date: 1974-11-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP50130554A

Other languages

English (en)

Japanese (ja)

Other versions

JPS51101799A (en

Inventor

クレーマンアクセル

ハイムウオルフガング

シエライエルゲルト

コルプハインツ

フリードリツヒハインツ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Evonik Operations GmbH

Original Assignee

Degussa GmbH

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.)

1974-11-18

Filing date

1975-10-31

Publication date

1983-09-24

1974-11-18 Priority claimed from DE19742454630 external-priority patent/DE2454630C3/de

1975-10-31 Application filed by Degussa GmbH filed Critical Degussa GmbH

1976-09-08 Publication of JPS51101799A publication Critical patent/JPS51101799A/ja

1983-09-24 Publication of JPS5843142B2 publication Critical patent/JPS5843142B2/ja

Status Expired legal-status Critical Current

Links

239000003822 epoxy resin Substances 0.000 title 2
229920000647 polyepoxide Polymers 0.000 title 2
125000002887 hydroxy group Chemical group [H]O* 0.000 title 1
229920005989 resin Polymers 0.000 title 1
239000011347 resin Substances 0.000 title 1
239000003054 catalyst Substances 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 34
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 25
239000012530 fluid Substances 0.000 claims description 21
239000000463 material Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
238000004821 distillation Methods 0.000 claims description 11
238000006735 epoxidation reaction Methods 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 9
238000005805 hydroxylation reaction Methods 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 8
239000011343 solid material Substances 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
-1 olefin compound Chemical class 0.000 claims description 2
239000013543 active substance Substances 0.000 claims 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 18
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 12
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 11
239000002912 waste gas Substances 0.000 description 10
230000033444 hydroxylation Effects 0.000 description 8
239000000126 substance Substances 0.000 description 8
238000002485 combustion reaction Methods 0.000 description 7
235000011187 glycerol Nutrition 0.000 description 7
239000002245 particle Substances 0.000 description 7
239000004576 sand Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 6
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 6
238000005406 washing Methods 0.000 description 6
239000002253 acid Substances 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
229910052721 tungsten Inorganic materials 0.000 description 4
239000010937 tungsten Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 2
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
238000003287 bathing Methods 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000004927 clay Substances 0.000 description 2
WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
YBVAXJOZZAJCLA-UHFFFAOYSA-N nitric acid nitrous acid Chemical compound ON=O.O[N+]([O-])=O YBVAXJOZZAJCLA-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000011084 recovery Methods 0.000 description 2
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
229910010271 silicon carbide Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
229910052720 vanadium Inorganic materials 0.000 description 2
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
239000002699 waste material Substances 0.000 description 2
239000002351 wastewater Substances 0.000 description 2
BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
YQCOCCVQWUFVFN-UHFFFAOYSA-N N(=O)O.[N+](=O)(O)[O-].[N+](=O)(O)[O-] Chemical compound N(=O)O.[N+](=O)(O)[O-].[N+](=O)(O)[O-] YQCOCCVQWUFVFN-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
238000007664 blowing Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229910052593 corundum Inorganic materials 0.000 description 1
239000010431 corundum Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010304 firing Methods 0.000 description 1
239000003546 flue gas Substances 0.000 description 1
238000005243 fluidization Methods 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000012716 precipitator Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
150000003658 tungsten compounds Chemical class 0.000 description 1

Classifications

- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/92—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G31/00—Compounds of vanadium
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G39/00—Compounds of molybdenum
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Epoxy Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Devices And Processes Conducted In The Presence Of Fluids And Solid Particles (AREA)

JP50130554A 1974-11-18 1975-10-31 オレフインケイカゴウブツノカサンカスイソニヨルエポキシカオヨビヒドロキシカニサイシテノシヨクバイノカイシユウホウホウ Expired JPS5843142B2 (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742454630 DE2454630C3 (de)		1974-11-18	Verfahren zur Wiedergewinnung von Katalysatoren bei der Epoxidation und Hydroxylierung von olefinischen Verbindungen mit Wasserstoffperoxid

Publications (2)

Publication Number	Publication Date
JPS51101799A JPS51101799A (en)	1976-09-08
JPS5843142B2 true JPS5843142B2 (ja)	1983-09-24

Family

ID=5931138

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP50130554A Expired JPS5843142B2 (ja)	1974-11-18	1975-10-31	オレフインケイカゴウブツノカサンカスイソニヨルエポキシカオヨビヒドロキシカニサイシテノシヨクバイノカイシユウホウホウ

Country Status (6)

Country	Link
JP (1)	JPS5843142B2 (de)
AT (1)	AT347908B (de)
BE (1)	BE835663A (de)
FR (1)	FR2290951A1 (de)
NL (1)	NL182292C (de)
PL (1)	PL98066B1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3263557A1 (de) *	2016-06-30	2018-01-03	Evonik Degussa GmbH	Verfahren zur reaktivierung eines homogenen oxidationskatalysators

1975
- 1975-09-24 NL NLAANVRAGE7511251,A patent/NL182292C/xx not_active IP Right Cessation
- 1975-10-22 FR FR7532363A patent/FR2290951A1/fr active Granted
- 1975-10-31 JP JP50130554A patent/JPS5843142B2/ja not_active Expired
- 1975-11-17 PL PL1975184784A patent/PL98066B1/pl unknown
- 1975-11-17 BE BE6045255A patent/BE835663A/xx not_active IP Right Cessation
- 1975-11-18 AT AT877975A patent/AT347908B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
NL182292B (nl)	1987-09-16
ATA877975A (de)	1978-06-15
FR2290951B1 (de)	1978-04-07
NL182292C (nl)	1988-02-16
DE2454630A1 (de)	1976-05-26
JPS51101799A (en)	1976-09-08
DE2454630B2 (de)	1977-05-12
FR2290951A1 (fr)	1976-06-11
PL98066B1 (pl)	1978-04-29
AT347908B (de)	1979-01-25
NL7511251A (nl)	1976-05-20
BE835663A (fr)	1976-05-17

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JPS5843142B2 - オレフインケイカゴウブツ ノ カサンカスイソニヨル エポキシカ オヨビ ヒドロキシカニサイシテノ シヨクバイノ カイシユウホウホウ - Google Patents