CA1086330A - Process for the addition of organic acids to acetylenic compounds contained in inorganic or organic hydrocarbon streams - Google Patents
Process for the addition of organic acids to acetylenic compounds contained in inorganic or organic hydrocarbon streamsInfo
- Publication number
- CA1086330A CA1086330A CA256,496A CA256496A CA1086330A CA 1086330 A CA1086330 A CA 1086330A CA 256496 A CA256496 A CA 256496A CA 1086330 A CA1086330 A CA 1086330A
- Authority
- CA
- Canada
- Prior art keywords
- ions
- carried out
- gem
- stripping
- alone
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 16
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 16
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 title claims abstract description 11
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 6
- 235000005985 organic acids Nutrition 0.000 title description 3
- 229920005989 resin Polymers 0.000 claims abstract description 26
- 239000011347 resin Substances 0.000 claims abstract description 26
- 230000002378 acidificating effect Effects 0.000 claims abstract description 10
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 8
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 8
- 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 7
- 229910006069 SO3H Inorganic materials 0.000 claims abstract 2
- 150000002500 ions Chemical class 0.000 claims description 19
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 12
- -1 polyphenolic Substances 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 9
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 229920001567 vinyl ester resin Polymers 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 6
- 238000007259 addition reaction Methods 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 claims description 4
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229940116441 divinylbenzene Drugs 0.000 claims description 2
- 239000007792 gaseous phase Substances 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 229910001987 mercury nitrate Inorganic materials 0.000 claims description 2
- DRXYRSRECMWYAV-UHFFFAOYSA-N nitrooxymercury Chemical compound [Hg+].[O-][N+]([O-])=O DRXYRSRECMWYAV-UHFFFAOYSA-N 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims 2
- 150000002730 mercury Chemical class 0.000 claims 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 16
- 239000002253 acid Substances 0.000 abstract description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 abstract description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- ORMNPSYMZOGSSV-UHFFFAOYSA-N mercury(II) nitrate Inorganic materials [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 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
- C07C7/17—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with acids or sulfur oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25171/75A IT1039740B (it) | 1975-07-08 | 1975-07-08 | Procedimento per l addizione di acidi organici a composti acetile nici contenuti in correnet i idrocar buriche inorganiche do organiche |
| IT25171A/75 | 1975-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086330A true CA1086330A (en) | 1980-09-23 |
Family
ID=11215901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,496A Expired CA1086330A (en) | 1975-07-08 | 1976-07-07 | Process for the addition of organic acids to acetylenic compounds contained in inorganic or organic hydrocarbon streams |
Country Status (34)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3127751A1 (de) * | 1981-07-14 | 1983-02-03 | EC Erdölchemie GmbH, 5000 Köln | Verfahren zur hydrierung von kohlenwasserstoffen |
| GB9314514D0 (en) * | 1993-07-13 | 1993-08-25 | Ici Plc | Hydrocarbon processing |
| US5952523A (en) * | 1997-07-24 | 1999-09-14 | Praxair Technology, Inc. | Method for producing vinyl acetate |
| RU2228301C2 (ru) * | 2001-01-09 | 2004-05-10 | Государственное образовательное учреждение высшего профессионального образования "Самарская государственная архитектурно-строительная академия" | Способ очистки масло- и жиросодержащих сточных вод |
| DE10113381A1 (de) * | 2001-02-13 | 2002-08-14 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von hochreinem Diisobuten |
| US8742194B2 (en) * | 2012-05-21 | 2014-06-03 | CM Global Systems, LLC | Hydrocarbon-containing mixture and method and system for making the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL291243A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-04-25 | 1900-01-01 | ||
| US3287402A (en) * | 1964-05-25 | 1966-11-22 | Mobil Oil Corp | Synthesis of vinyl esters in the presence of a crystalline aluminosilicate catalyst |
-
1975
- 1975-07-08 IT IT25171/75A patent/IT1039740B/it active
-
1976
- 1976-06-25 ZA ZA763798A patent/ZA763798B/xx unknown
- 1976-06-25 NO NO762205A patent/NO145572C/no unknown
- 1976-06-30 AU AU15437/76A patent/AU500172B2/en not_active Expired
- 1976-07-05 YU YU01645/76A patent/YU164576A/xx unknown
- 1976-07-05 DK DK303876A patent/DK303876A/da not_active Application Discontinuation
- 1976-07-06 DD DD7600200188A patent/DD130572A5/xx unknown
- 1976-07-06 US US05/703,121 patent/US4066713A/en not_active Expired - Lifetime
- 1976-07-06 IN IN1196/CAL/1976A patent/IN144603B/en unknown
- 1976-07-06 CS CS764466A patent/CS194770B2/cs unknown
- 1976-07-06 EG EG407/76A patent/EG12199A/xx active
- 1976-07-06 DD DD193730A patent/DD127302A5/xx unknown
- 1976-07-06 TR TR18997A patent/TR18997A/xx unknown
- 1976-07-06 ES ES449922A patent/ES449922A1/es not_active Expired
- 1976-07-06 GB GB28110/76A patent/GB1499646A/en not_active Expired
- 1976-07-06 LU LU75312A patent/LU75312A1/xx unknown
- 1976-07-07 CA CA256,496A patent/CA1086330A/en not_active Expired
- 1976-07-07 NL NL7607525A patent/NL7607525A/xx not_active Application Discontinuation
- 1976-07-07 AT AT498776A patent/AT345263B/de not_active IP Right Cessation
- 1976-07-07 IE IE1502/76A patent/IE43389B1/en unknown
- 1976-07-07 HU HU76SA2940A patent/HU178719B/hu unknown
- 1976-07-07 PT PT65331A patent/PT65331B/pt unknown
- 1976-07-07 RO RO7686861A patent/RO74131A/ro unknown
- 1976-07-07 CH CH872976A patent/CH626267A5/it not_active IP Right Cessation
- 1976-07-07 FR FR7620820A patent/FR2317256A1/fr active Granted
- 1976-07-08 AR AR263905A patent/AR221029A1/es active
- 1976-07-08 BE BE168744A patent/BE843917A/xx not_active IP Right Cessation
- 1976-07-08 DE DE2630783A patent/DE2630783C3/de not_active Expired
- 1976-07-08 PL PL1976191023A patent/PL108187B1/pl unknown
- 1976-07-08 PH PH18661A patent/PH13775A/en unknown
- 1976-07-08 SE SE7607853A patent/SE425385B/xx unknown
- 1976-07-08 MX MX165433A patent/MX144146A/es unknown
- 1976-07-08 JP JP51080431A patent/JPS602287B2/ja not_active Expired
- 1976-07-08 BR BR7605717A patent/BR7605717A/pt unknown
- 1976-07-08 SU SU762379564A patent/SU751320A3/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |