CA1064045A - Procede pour preparer des derives de l'oxirane - Google Patents

Procede pour preparer des derives de l'oxirane

Info

Publication number: CA1064045A
Authority: CA; Canada
Prior art keywords: carbon atoms; acetic acid; mixture; acid; solvent
Prior art date: 1974-07-31
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

CA232,468A

Other languages

English (en)

Inventor

Gunther Nowy

Harald Haberlein

Helmut Korbanka

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1974-07-31

Filing date

1975-07-29

Publication date

1979-10-09

1974-07-31 Priority claimed from DE19742436827 external-priority patent/DE2436827C2/de

1975-05-22 Priority claimed from DE19752522661 external-priority patent/DE2522661A1/de

1975-07-29 Application filed by Hoechst AG filed Critical Hoechst AG

1979-10-09 Application granted granted Critical

1979-10-09 Publication of CA1064045A publication Critical patent/CA1064045A/fr

Status Expired legal-status Critical Current

Links

150000002924 oxiranes Chemical class 0.000 title abstract description 34
238000004519 manufacturing process Methods 0.000 title abstract description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 74
239000000203 mixture Substances 0.000 claims abstract description 47
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 36
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
238000006243 chemical reaction Methods 0.000 claims abstract description 22
239000007788 liquid Substances 0.000 claims abstract description 12
229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 34
239000002904 solvent Substances 0.000 claims description 17
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 14
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
230000008569 process Effects 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
230000002378 acidificating effect Effects 0.000 claims description 9
229930195733 hydrocarbon Natural products 0.000 claims description 8
150000002430 hydrocarbons Chemical class 0.000 claims description 8
230000003647 oxidation Effects 0.000 claims description 7
238000007254 oxidation reaction Methods 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
239000011347 resin Substances 0.000 claims description 4
229920005989 resin Polymers 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
229950011008 tetrachloroethylene Drugs 0.000 claims description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 2
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims 2
QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 claims 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 1
125000002091 cationic group Chemical group 0.000 claims 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
-1 aliphatic chlorinated hydrocarbons Chemical class 0.000 abstract description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 28
150000001336 alkenes Chemical class 0.000 description 28
239000011630 iodine Substances 0.000 description 28
229910052740 iodine Inorganic materials 0.000 description 28
229960000583 acetic acid Drugs 0.000 description 26
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
229910052760 oxygen Inorganic materials 0.000 description 17
239000001301 oxygen Substances 0.000 description 17
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 16
235000011054 acetic acid Nutrition 0.000 description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
239000007795 chemical reaction product Substances 0.000 description 15
229960002163 hydrogen peroxide Drugs 0.000 description 15
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
229940032330 sulfuric acid Drugs 0.000 description 12
239000012362 glacial acetic acid Substances 0.000 description 10
238000006735 epoxidation reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000001816 cooling Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000004965 peroxy acids Chemical class 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
IMYZYCNQZDBZBQ-UHFFFAOYSA-N (+-)-8-(cis-3-octyl-oxiranyl)-octanoic acid Natural products CCCCCCCCC1OC1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-UHFFFAOYSA-N 0.000 description 2
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
229960003750 ethyl chloride Drugs 0.000 description 2
NNYBQONXHNTVIJ-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-UHFFFAOYSA-N 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229940063718 lodine Drugs 0.000 description 2
CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
125000000466 oxiranyl group Chemical group 0.000 description 2
230000036647 reaction Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
241000022563 Rema Species 0.000 description 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000153282 Theope Species 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004106 carminic acid Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
235000019628 coolness Nutrition 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
239000000727 fraction Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
235000021081 unsaturated fats Nutrition 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
229940045860 white wax Drugs 0.000 description 1

Landscapes

Epoxy Compounds (AREA)

CA232,468A 1974-07-31 1975-07-29 Procede pour preparer des derives de l'oxirane Expired CA1064045A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19742436827 DE2436827C2 (de)		1974-07-31	Schaltung für einen schnellen Synchron-Delektor zur Trennung von AM-modulierten Zeitmultiplexsignalen
DE19752522661 DE2522661A1 (de)	1975-05-22	1975-05-22	Verfahren zur herstellung von oxiranverbindungen

Publications (1)

Publication Number	Publication Date
CA1064045A true CA1064045A (fr)	1979-10-09

Family

ID=25767495

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA232,468A Expired CA1064045A (fr)	1974-07-31	1975-07-29	Procede pour preparer des derives de l'oxirane

Country Status (1)

Country	Link
CA (1)	CA1064045A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116273185A (zh) *	2023-03-01	2023-06-23	大连理工大学	一种固载化双功能催化剂及其在外环路反应工艺中制备环状碳酸酯的方法

1975
- 1975-07-29 CA CA232,468A patent/CA1064045A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116273185A (zh) *	2023-03-01	2023-06-23	大连理工大学	一种固载化双功能催化剂及其在外环路反应工艺中制备环状碳酸酯的方法
CN116273185B (zh) *	2023-03-01	2024-04-19	大连理工大学	一种固载化双功能催化剂及其在外环路反应工艺中制备环状碳酸酯的方法

Publication	Publication Date	Title
US5166372A (en)	1992-11-24	Epoxidation process
US2831877A (en)	1958-04-22	Production of carboxylic acids from olefins
US4071541A (en)	1978-01-31	Epoxidation
JPH024223B2 (fr)	1990-01-26
CA1244043A (fr)	1988-11-01	Epoxydation d'hydrocarbures olefiniques a l'aide d'acide peracetique
GB1585012A (en)	1981-02-18	Process for the epoxidation of olefins
CA1064045A (fr)	1979-10-09	Procede pour preparer des derives de l'oxirane
US3954884A (en)	1976-05-04	Method for producing beta hydroxy ethylene glycol ethers
US2813885A (en)	1957-11-19	Process for making fatty peracids
US2890228A (en)	1959-06-09	New polyamide like condensation products and process of producing the same
US4193929A (en)	1980-03-18	Epoxidation
US4168274A (en)	1979-09-18	Production of a peracid and an oxirane
US3662004A (en)	1972-05-09	Process for producing hydroxyalkyl mercaptans
JPS6157813B2 (fr)	1986-12-09
US3755463A (en)	1973-08-28	Process for the preparation of hydroxyalkyl mercaptans
DE3002861C2 (de)	1981-11-12	Verfahren zur Herstellung von Epoxyalkanen
US3360531A (en)	1967-12-26	In situ epoxidation process
US3328430A (en)	1967-06-27	Epoxidation process
US3413278A (en)	1968-11-26	Process for the production of telomers of ethylene with amines and products
US4172840A (en)	1979-10-30	Epoxidation
US4177196A (en)	1979-12-04	Epoxidation
NO135997B (fr)	1977-03-28
US3141896A (en)	1964-07-21	Process for the percarboxylic acid epqxr
US4612398A (en)	1986-09-16	Alkyl mercaptan process
JPS6233166A (ja)	1987-02-13	脂環式ジエポキシドの製造法