IE43609B1 - Process for the addition of alcohols to acetylenic compounds, and process for the removal of acetylenic compounds from mixtures - Google Patents
Process for the addition of alcohols to acetylenic compounds, and process for the removal of acetylenic compounds from mixturesInfo
- Publication number
- IE43609B1 IE43609B1 IE1501/76A IE150176A IE43609B1 IE 43609 B1 IE43609 B1 IE 43609B1 IE 1501/76 A IE1501/76 A IE 1501/76A IE 150176 A IE150176 A IE 150176A IE 43609 B1 IE43609 B1 IE 43609B1
- Authority
- IE
- Ireland
- Prior art keywords
- process according
- alcohol
- butyne
- ions
- acetylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 title claims description 13
- 150000001298 alcohols Chemical class 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002500 ions Chemical class 0.000 claims abstract description 14
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 7
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 6
- 239000011347 resin Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 13
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 12
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 12
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 claims description 7
- -1 hydrogen ions Chemical class 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 6
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- ORMNPSYMZOGSSV-UHFFFAOYSA-N dinitrooxymercury Chemical group [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 2
- 229920000178 Acrylic resin Polymers 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 150000002484 inorganic compounds Chemical class 0.000 claims description 2
- 229910010272 inorganic material Inorganic materials 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910021645 metal ion Inorganic materials 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract 2
- 238000007259 addition reaction Methods 0.000 abstract 1
- 229910001413 alkali metal ion Inorganic materials 0.000 abstract 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 abstract 1
- 150000001345 alkine derivatives Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25170/75A IT1039739B (it) | 1975-07-08 | 1975-07-08 | Procedimento per l addizione di alcoli a composti acetilenici contenuti in correnti idrocarburiche organiche od inorganiche |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43609L IE43609L (en) | 1977-01-08 |
| IE43609B1 true IE43609B1 (en) | 1981-04-08 |
Family
ID=11215900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1501/76A IE43609B1 (en) | 1975-07-08 | 1976-07-07 | Process for the addition of alcohols to acetylenic compounds, and process for the removal of acetylenic compounds from mixtures |
Country Status (34)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3700605A1 (de) * | 1987-01-10 | 1988-07-21 | Huels Chemische Werke Ag | Verfahren zur herstellung von alkoxibuteninen |
| GB9314514D0 (en) * | 1993-07-13 | 1993-08-25 | Ici Plc | Hydrocarbon processing |
| KR102561860B1 (ko) * | 2016-10-25 | 2023-08-02 | 삼성전자주식회사 | 전자장치 및 그 제어방법 |
-
1975
- 1975-07-08 IT IT25170/75A patent/IT1039739B/it active
-
1976
- 1976-06-25 NO NO762204A patent/NO762204L/no unknown
- 1976-06-25 ZA ZA763797A patent/ZA763797B/xx unknown
- 1976-06-30 YU YU1611/76A patent/YU37303B/xx unknown
- 1976-06-30 AU AU15433/76A patent/AU501768B2/en not_active Expired
- 1976-07-01 ZM ZM88/76A patent/ZM8876A1/xx unknown
- 1976-07-01 ZM ZM89/76A patent/ZM8976A1/xx unknown
- 1976-07-05 DK DK303676A patent/DK303676A/da not_active Application Discontinuation
- 1976-07-06 TR TR18958A patent/TR18958A/xx unknown
- 1976-07-06 CS CS764465A patent/CS194769B2/cs unknown
- 1976-07-06 DD DD7600200187A patent/DD131012A5/xx unknown
- 1976-07-06 DD DD193731A patent/DD127082A5/xx unknown
- 1976-07-06 ES ES449923A patent/ES449923A1/es not_active Expired
- 1976-07-06 IN IN1195/CAL/1976A patent/IN145252B/en unknown
- 1976-07-06 GB GB28109/76A patent/GB1519714A/en not_active Expired
- 1976-07-06 LU LU75304A patent/LU75304A1/xx unknown
- 1976-07-06 EG EG406/76A patent/EG12170A/xx active
- 1976-07-07 NL NL7607524A patent/NL7607524A/ not_active Application Discontinuation
- 1976-07-07 PT PT65330A patent/PT65330B/pt unknown
- 1976-07-07 CH CH872876A patent/CH626266A5/it not_active IP Right Cessation
- 1976-07-07 RO RO7686863A patent/RO70953A/ro unknown
- 1976-07-07 IE IE1501/76A patent/IE43609B1/en unknown
- 1976-07-07 AT AT498676A patent/AT345262B/de not_active IP Right Cessation
- 1976-07-07 FR FR7620819A patent/FR2317265A1/fr active Granted
- 1976-07-07 HU HU76SA2942A patent/HU178721B/hu unknown
- 1976-07-07 CA CA256,494A patent/CA1075721A/en not_active Expired
- 1976-07-08 BE BE168743A patent/BE843916A/xx not_active IP Right Cessation
- 1976-07-08 PL PL1976191024A patent/PL108186B1/pl unknown
- 1976-07-08 MX MX165436A patent/MX142865A/es unknown
- 1976-07-08 SU SU762379661A patent/SU991943A3/ru active
- 1976-07-08 AR AR263906A patent/AR217057A1/es active
- 1976-07-08 SE SE7607852A patent/SE7607852L/ not_active Application Discontinuation
- 1976-07-08 DE DE2630769A patent/DE2630769C3/de not_active Expired
- 1976-07-08 JP JP51080430A patent/JPS602286B2/ja not_active Expired
- 1976-07-08 BR BR7605718A patent/BR7605718A/pt unknown
- 1976-07-08 PH PH18662A patent/PH15669A/en unknown
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