CA1170665A - Methode de reaction des epoxys avec un compose organique ayant un hydrogene actif - Google Patents

Methode de reaction des epoxys avec un compose organique ayant un hydrogene actif

Info

Publication number: CA1170665A
Authority: CA; Canada
Prior art keywords: calcium; strontium; barium; reaction; grams
Prior art date: 1979-09-27
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

CA000359572A

Other languages

English (en)

Inventor

James H. Mccain, Jr.

Donald J. Foster

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.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1979-09-27

Filing date

1980-09-04

Publication date

1984-07-10

1980-09-04 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1984-07-10 Application granted granted Critical

1984-07-10 Publication of CA1170665A publication Critical patent/CA1170665A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 40
238000006243 chemical reaction Methods 0.000 title claims abstract description 31
239000001257 hydrogen Substances 0.000 title claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 22
150000002894 organic compounds Chemical class 0.000 title claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 6
150000002118 epoxides Chemical class 0.000 title claims abstract 5
239000011575 calcium Substances 0.000 claims abstract description 41
229910052791 calcium Inorganic materials 0.000 claims abstract description 41
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 37
239000007795 chemical reaction product Substances 0.000 claims abstract description 26
229910052712 strontium Inorganic materials 0.000 claims abstract description 26
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims abstract description 26
229910052788 barium Inorganic materials 0.000 claims abstract description 20
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 19
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 17
150000001447 alkali salts Chemical class 0.000 claims abstract description 15
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 15
229920005862 polyol Polymers 0.000 claims abstract description 13
150000003077 polyols Chemical class 0.000 claims abstract description 13
150000001298 alcohols Chemical class 0.000 claims abstract description 11
239000000376 reactant Substances 0.000 claims abstract description 9
150000002989 phenols Chemical class 0.000 claims abstract description 7
150000001412 amines Chemical class 0.000 claims abstract description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
-1 alkaline earth metal salt Chemical class 0.000 claims description 44
239000003054 catalyst Substances 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 32
230000003197 catalytic effect Effects 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000011065 in-situ storage Methods 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
150000001336 alkenes Chemical class 0.000 claims description 2
150000004767 nitrides Chemical class 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
JENCOQNWECEFQI-UHFFFAOYSA-N azanide;barium(2+) Chemical class [NH2-].[NH2-].[Ba+2] JENCOQNWECEFQI-UHFFFAOYSA-N 0.000 claims 1
HMOHOVASWYMMHA-UHFFFAOYSA-L barium(2+);diphenoxide Chemical class [Ba+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 HMOHOVASWYMMHA-UHFFFAOYSA-L 0.000 claims 1
239000000047 product Substances 0.000 abstract description 32
238000009826 distribution Methods 0.000 abstract description 17
239000002253 acid Substances 0.000 abstract description 8
150000007513 acids Chemical class 0.000 abstract description 4
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239000002184 metal Substances 0.000 description 14
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PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
238000005227 gel permeation chromatography Methods 0.000 description 8
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
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WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
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239000006227 byproduct Substances 0.000 description 5
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241000894007 species Species 0.000 description 5
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238000006386 neutralization reaction Methods 0.000 description 4
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BWKDLDWUVLGWFC-UHFFFAOYSA-N calcium;azanide Chemical class [NH2-].[NH2-].[Ca+2] BWKDLDWUVLGWFC-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
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230000002349 favourable effect Effects 0.000 description 3
239000000463 material Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
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HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
GYIWFHXWLCXGQO-UHFFFAOYSA-N barium(2+);ethanolate Chemical compound [Ba+2].CC[O-].CC[O-] GYIWFHXWLCXGQO-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
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238000006482 condensation reaction Methods 0.000 description 2
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ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
150000002483 hydrogen compounds Chemical class 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
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GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
XGQJZNCFDLXSIJ-UHFFFAOYSA-N pentadecanal Chemical compound CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 2
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AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
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239000001110 calcium chloride Substances 0.000 description 1
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239000001569 carbon dioxide Substances 0.000 description 1
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150000001735 carboxylic acids Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
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125000004122 cyclic group Chemical group 0.000 description 1
QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
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230000001419 dependent effect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
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UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
WTQUVYBGJUBJSW-UHFFFAOYSA-N oxacycloundecane Chemical compound C1CCCCCOCCCC1 WTQUVYBGJUBJSW-UHFFFAOYSA-N 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229940067107 phenylethyl alcohol Drugs 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003152 propanolamines Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229940095050 propylene Drugs 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
YTBRWVXQNMQQTK-UHFFFAOYSA-N strontium;ethanolate Chemical compound CCO[Sr]OCC YTBRWVXQNMQQTK-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Landscapes

Epoxy Resins (AREA)
Polyethers (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000359572A 1979-09-27 1980-09-04 Methode de reaction des epoxys avec un compose organique ayant un hydrogene actif Expired CA1170665A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7953879A	1979-09-27	1979-09-27
US079,538		1979-09-27

Publications (1)

Publication Number	Publication Date
CA1170665A true CA1170665A (fr)	1984-07-10

Family

ID=22151180

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000359572A Expired CA1170665A (fr)	1979-09-27	1980-09-04	Methode de reaction des epoxys avec un compose organique ayant un hydrogene actif

Country Status (2)

Country	Link
JP (1)	JPS5650920A (fr)
CA (1)	CA1170665A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62500178A (ja) *	1984-12-04	1987-01-22	ザ　ダウ　ケミカル　カンパニ−	熱安定性熱可塑性樹脂の製造方法
JPS63280986A (ja) *	1987-05-11	1988-11-17	明星工業株式会社	ペネトレ−ション用ブ−ツ取付け構造
JPH0633380B2 (ja) *	1990-06-25	1994-05-02	日揮株式会社	代替天然ガスの製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4856798A (fr) *	1971-11-22	1973-08-09

1980
- 1980-09-04 CA CA000359572A patent/CA1170665A/fr not_active Expired
- 1980-09-24 JP JP13178580A patent/JPS5650920A/ja active Granted

Also Published As

Publication number	Publication date
JPS5650920A (en)	1981-05-08
JPS6256891B2 (fr)	1987-11-27

Legal Events

Date	Code	Title	Description
2001-07-10	MKEX	Expiry

Publication	Publication Date	Title
EP0026546B1 (fr)	1985-09-04	Procédé pour la réaction des époxydes avec des composés ayant un hydrogène actif
EP0026547B1 (fr)	1984-02-01	Procédé pour la préparation de sels alcalino-terreux basiques
EP0026544B1 (fr)	1984-02-15	Procédé pour la préparation de sels basiques de barium
CA1247650A (fr)	1988-12-28	Preparation de surfactifs non ioniques - oxyalcoylation a l'aide de catalyseurs actives a base de baryum
CA1260018A (fr)	1989-09-26	Methode d'alcoxylation utilisant un catalyseur oxo bimetallique
EP0777527B1 (fr)	2002-02-13	Procede de preparation de catalyseurs d'alcoxylation et procede d'alcoxylation
EP0115083B1 (fr)	1986-03-26	Procédé catalytique de préparation de surfactifs non ioniques
CA1260017A (fr)	1989-09-26	Methode d'alcoxylation utilisant un catalyseur oxo bimetallique
EP1358142B1 (fr)	2006-06-07	Procede d'alcoxylation au moyen d'un catalyseur renfermant du bore
CA1170665A (fr)	1984-07-10	Methode de reaction des epoxys avec un compose organique ayant un hydrogene actif
AU2005288959A1 (en)	2006-04-06	Process for preparing an alkoxylated alcohol or phenol
EP0398450A2 (fr)	1990-11-22	Procédé d'alkoxylation catalysé par phosphate de barium
EP1351910B1 (fr)	2004-10-27	Procede d'alcoxylation en presence de triflimides de terres rares
KR100199303B1 (ko)	1999-06-15	나트륨-또는 칼륨 바륨 포스페이트에 의해 촉매된 알콕시화 방법
JP2005536348A (ja)	2005-12-02	炭酸塩からの希土類リン酸塩触媒の調製およびアルコキシ化反応におけるその使用
JP2739648B2 (ja)	1998-04-15	ランタン系列の触媒を用いるアルコキシル化方法
CA1187106A (fr)	1985-05-14	Methode de preparation d'agents tensioactifs anioniques a masse moleculaire concentree
WO2026005975A1 (fr)	2026-01-02	Alcoxylation à polydispersité étroite avec catalyseur alternatif
ZA200500916B (en)	2006-11-29	Preparation of earth phosphate catalysts from carbonate salts and their use in alkoxylation reactions