DE1211152B - Verfahren zur Herstellung von Vinylaethern und Vinylsulfiden - Google Patents
Verfahren zur Herstellung von Vinylaethern und VinylsulfidenInfo
- Publication number
- DE1211152B DE1211152B DER30797A DER0030797A DE1211152B DE 1211152 B DE1211152 B DE 1211152B DE R30797 A DER30797 A DE R30797A DE R0030797 A DER0030797 A DE R0030797A DE 1211152 B DE1211152 B DE 1211152B
- Authority
- DE
- Germany
- Prior art keywords
- acetylene
- vinyl
- mol
- water
- alkylene oxide
- Prior art date
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 11
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title claims description 8
- 150000008127 vinyl sulfides Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 27
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 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 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 14
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- -1 alkoxy radical Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- UIYCHXAGWOYNNA-UHFFFAOYSA-N divinyl sulphide Natural products C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- CJDXLHTYSXHWDC-UHFFFAOYSA-N 2-ethenylsulfanylethanol Chemical compound OCCSC=C CJDXLHTYSXHWDC-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000006886 vinylation reaction Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MBQIGVLDESBKFG-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-methoxyethane Chemical compound COCCOCCOC=C MBQIGVLDESBKFG-UHFFFAOYSA-N 0.000 description 1
- GXZPMXGRNUXGHN-UHFFFAOYSA-N 1-ethenoxy-2-methoxyethane Chemical compound COCCOC=C GXZPMXGRNUXGHN-UHFFFAOYSA-N 0.000 description 1
- ULPCQLFOPAJTBL-UHFFFAOYSA-N 1-ethenoxy-4-[(2-methylpropan-2-yl)oxy]butane Chemical compound C(=C)OCCCCOC(C)(C)C ULPCQLFOPAJTBL-UHFFFAOYSA-N 0.000 description 1
- BMAANCPDDFIZMG-UHFFFAOYSA-N 1-ethenylsulfanylpropan-2-ol Chemical compound CC(O)CSC=C BMAANCPDDFIZMG-UHFFFAOYSA-N 0.000 description 1
- ISVBFNQFNVSKOA-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)-2-methylpropane Chemical compound CC(C)(C)OCCOC=C ISVBFNQFNVSKOA-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- LTRQMIRHHAOUEB-UHFFFAOYSA-N C=CSCC(C1=CC=CC=C1)O Chemical compound C=CSCC(C1=CC=CC=C1)O LTRQMIRHHAOUEB-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- AAYFQAPISKPSSI-UHFFFAOYSA-N [N].C#C Chemical compound [N].C#C AAYFQAPISKPSSI-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- LUFUWJZCIDKWJV-UHFFFAOYSA-N methanol;oxirane Chemical compound OC.C1CO1 LUFUWJZCIDKWJV-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
- C07C41/08—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only to carbon-to-carbon triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46357A US3062892A (en) | 1960-08-01 | 1960-08-01 | One step synthesis of vinyl ethers and vinyl sulfides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1211152B true DE1211152B (de) | 1966-02-24 |
| DE1211152C2 DE1211152C2 (en, 2012) | 1966-09-01 |
Family
ID=21943021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER30797A Granted DE1211152B (de) | 1960-08-01 | 1961-07-21 | Verfahren zur Herstellung von Vinylaethern und Vinylsulfiden |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3062892A (en, 2012) |
| BE (1) | BE606780A (en, 2012) |
| DE (1) | DE1211152B (en, 2012) |
| GB (1) | GB989883A (en, 2012) |
| NL (1) | NL267743A (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3345255A (en) * | 1964-07-13 | 1967-10-03 | Stauffer Chemical Co | Controlling fungi with 1, 2-dichlorovinyl hydroxyethyl sulfide |
| US4086278A (en) * | 1976-03-15 | 1978-04-25 | Ortho Pharmaceutical Corporation | 1-alkenyl thioethers |
| DE3903279A1 (de) * | 1988-02-03 | 1989-08-10 | Mitsubishi Gas Chemical Co | Schwefel enthaltende aromatische vinylverbindung |
| JP2003089752A (ja) * | 2001-03-23 | 2003-03-28 | Canon Inc | 刺激応答性ポリマーを含む組成物、それを含むインク組成物、並びに該インク組成物を用いた画像形成方法および装置 |
| JP3595805B2 (ja) * | 2001-08-07 | 2004-12-02 | キヤノン株式会社 | 刺激応答性組成物、並びに該組成物を用いた画像形成方法および装置 |
| EP1371696B1 (en) | 2002-06-14 | 2006-08-09 | Canon Kabushiki Kaisha | Particle composition, recording method, and recording apparatus using the particle composition |
| JP4020301B2 (ja) * | 2002-06-14 | 2007-12-12 | キヤノン株式会社 | インクジェット用記録インク |
| JP3891571B2 (ja) * | 2002-06-14 | 2007-03-14 | キヤノン株式会社 | 機能性組成物、それを用いた画像形成方法及び画像形成装置 |
| JP3890266B2 (ja) * | 2002-07-03 | 2007-03-07 | キヤノン株式会社 | ブロックポリマー化合物、インク組成物、分散性組成物及び画像形成方法並びに画像形成装置 |
| WO2021183340A1 (en) | 2020-03-10 | 2021-09-16 | Sirrus, Inc. | Radiation cured copolymers of dicarbonyl substituted-l-alkenes and electron rich comonomers |
-
0
- NL NL267743D patent/NL267743A/xx unknown
-
1960
- 1960-08-01 US US46357A patent/US3062892A/en not_active Expired - Lifetime
-
1961
- 1961-07-21 DE DER30797A patent/DE1211152B/de active Granted
- 1961-07-27 GB GB27300/61A patent/GB989883A/en not_active Expired
- 1961-08-01 BE BE606780A patent/BE606780A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB989883A (en) | 1965-04-22 |
| BE606780A (fr) | 1962-02-01 |
| DE1211152C2 (en, 2012) | 1966-09-01 |
| NL267743A (en, 2012) | |
| US3062892A (en) | 1962-11-06 |
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