WO2015075733A2 - Polymerization of hydrocarbons - Google Patents
Polymerization of hydrocarbons Download PDFInfo
- Publication number
- WO2015075733A2 WO2015075733A2 PCT/IN2014/000655 IN2014000655W WO2015075733A2 WO 2015075733 A2 WO2015075733 A2 WO 2015075733A2 IN 2014000655 W IN2014000655 W IN 2014000655W WO 2015075733 A2 WO2015075733 A2 WO 2015075733A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- reaction vessel
- hydrocarbon
- light
- light source
- photo
- Prior art date
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 51
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 51
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 31
- 239000003999 initiator Substances 0.000 claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 238000005401 electroluminescence Methods 0.000 claims description 8
- 238000010926 purge Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- 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 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000001261 hydroxy acids Chemical class 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000379 polymerizing effect Effects 0.000 description 5
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000008376 long-term health Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/08—Isoprene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/127—Sunlight; Visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/04—Acids; Metal salts or ammonium salts thereof
- C08F120/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J2219/0869—Feeding or evacuating the reactor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J2219/12—Processes employing electromagnetic waves
- B01J2219/1203—Incoherent waves
Definitions
- the present invention relates to a process and an apparatus for polymerizing hydrocarbons.
- Polymerization is a process of reacting monomer molecules together in a chemical reaction to form linear chains or a three-dimensional network of polymer chains.
- Conventional processes for polymerization include radical polymerization, cationic polymerization, anionic polymerization, photo-irradiation polymerization and coordination catalytic polymerization
- photo-irradiation polymerization process utilizes UV light emitted by various sources such as a filament-based lamp, vapor/gas-based lamp and the like.
- the filament-based or vapor/gas-based lamp used as a source of UV light emits defused or multi-directional UV light that exhibits a high rate of intensity decay with distance. Therefore, these lamps are incapable of inducing effective reactions which further lead to consumption of high amount of electrical power. Additionally, these lamps are bulky and have a short life period (8000- 15000 hours).
- LEDs Light Emitting Diodes
- the present disclosure provides a process for polymerization of a hydrocarbon comprises reacting, under agitation, the hydrocarbon and a photo-initiator in an atmosphere containing oxygen less than 0.65% in a reaction vessel by passing visible light of wavelength ranging from 390 to 780nm emitted by at least one light source, into the reaction vessel for a predetermined time period to obtain a polymerized hydrocarbon.
- an apparatus for polymerization of a hydrocarbon comprises a reaction vessel, a purging means to purge fluids into said reaction vessel, a guiding means to guide the light to a reaction zone of the reaction vessel, a centrally mounted stirrer and at least one light source.
- Figure 1(a) and 1(b) illustrate schematic illustration of the apparatus used for polymerization of hydrocarbons with light source placed inside and outside the reaction vessel respectively.
- At least one hydrocarbon and at least one photo-initiator is introduced in an atmosphere containing oxygen less than 0.65% into a reaction vessel and the mixture is agitated for a predetermined period of time.
- Hydrocarbons used in accordance with the present disclosure include but are not limited to isoprene, acrylic acid alcohol, epoxide, hydroxyacid, lactum and vinyl monomers.
- the hydrocarbon can be introduced in the reaction vessel in the form of a slurry or a solution. In one embodiment of the present disclosure the hydrocarbon is in the form of slurry.
- the hydrocarbon is heated at a temperature of 40 to 90°C before passing visible light into the reaction vessel.
- the photo-initiator used the present disclosure includes but is not limited to one or more peroxides selected from the group consisting of hydrogen peroxide, benzoyl peroxide t- butylhydroperoxide, perbenzoic acid and peracetic acid.
- the amount of photo-initiator used in the process of present disclosure ranges from 20 to 800ppm.
- a low oxygen level is maintained in the reaction vessel.
- the oxygen is less than 0.65% in the reaction vessel.
- Oxygen can be removed when introducing hydrocarbon in the reaction vessel or during the step of agitating the mixture of hydrocarbon and photo-initiator in the reaction vessel. The oxygen must be removed from the reaction vessel, as oxygen hinders the photo-initiated polymerization process.
- the method step of agitation is carried out with the help of a rotating stirrer at speeds ranging from 200 to 850 rpm for a time period of 5 to 60 minutes.
- an atmosphere containing oxygen less than 0.65% is established in the reaction vessel by purging an inert gas and subsequently visible light is passed for a period of 2 to 12 hours into the reaction vessel to obtain the polymerized hydrocarbon.
- the light source from which the visible light of wavelength 390 to 780 nm is emitted, is a bank of solid state light emitting devices.
- the solid state light emitting devices includes but not limited to Light Emitting Diodes (LEDs), LASER, Organic Electroluminescence material, Inorganic Electroluminescence, Organic Light Emitting Diodes and Inorganic Light Emitting Diodes.
- the light source is placed on at least one location selected from the group consisting of outside the reaction vessel, inside the reaction vessel and embedded on the walls of the reaction vessel.
- the distance between the exterior wall of the reaction vessel and the light source, placed outside the reaction vessel is in the range of 0.2 to 12 cm, preferably at a distance of 0.5 to 4cm.
- the step of passing light from a light source placed outside the reaction vessel includes guiding the beam of light to a reaction zone of reaction vessel in which the process is taking place.
- the apparatus includes a reaction vessel 1, purging means 3 and 4 to purge fluids into the reaction vessel, a centrally mounted stirrer 2 and at least one light source 6 placed inside the reaction vessel.
- the temperature in the reaction vessel is measured and maintained using a thermometer and heating bath 8 and 5 respectively.
- the apparatus of the present discloser also includes guiding means to guide the light from the light source to a reaction zone in the reaction vessel.
- the guiding means includes but is not limited to waveguide, lens and set of lenses. The entire set-up is supported using a clamping arrangement 7.
- the light source 6 is placed outside the reaction vessel keeping rest of the elements of the apparatus same as in the first embodiment.
- the light source from which the visible light of wavelength 390 to 780 nm is emitted, is solid state light emitting devices which includes but not limited to Light Emitting Diodes (LEDs), LASER, Organic Electroluminescence material, Inorganic Electroluminescence, Organic Light Emitting Diodes, Inorganic Light emitting Diodes and combinations thereof.
- LEDs Light Emitting Diodes
- LASER Organic Electroluminescence material
- Inorganic Electroluminescence Inorganic Electroluminescence
- Organic Light Emitting Diodes Inorganic Light emitting Diodes and combinations thereof.
- the light source is placed on at least one location selected from the group consisting of outside the reaction vessel, inside the reaction vessel and embedded on the walls of the reaction vessel.
- the distance between the exterior wall of the reaction vessel and the bank of LEDs placed outside the reaction vessel is in the range of 0.2 to 12 cm, preferably at a distance of 0.5 to 4cm.
- the reaction vessel is glass walled and transparent.
- Example 3 Radical-initiated Polymerization of an Unsaturated Hydrocarbon in the absence of inert gas purging:
- the present disclosure provides the process for polymerizing hydrocarbons that is carried out without addition of an additive.
- the process for polymerizing hydrocarbons is carried out in solid state light emitting devices.
- the process for the polymerizing hydrocarbons is simple and cost effective and environmentally safe.
- the present disclosure also provides an apparatus for polymerizing hydrocarbons.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14863811.7A EP3058000A4 (en) | 2013-10-18 | 2014-10-16 | Polymerization of hydrocarbons |
| US15/029,957 US9969825B2 (en) | 2013-10-18 | 2014-10-16 | Polymerization of hydrocarbons |
| CN201480057162.7A CN105658680A (zh) | 2013-10-18 | 2014-10-16 | 烃的聚合 |
| JP2016524464A JP6598770B2 (ja) | 2013-10-18 | 2014-10-16 | 炭化水素の重合 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3272/MUM/2013 | 2013-10-18 | ||
| IN3272MU2013 IN2013MU03272A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2013-10-18 | 2014-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2015075733A2 true WO2015075733A2 (en) | 2015-05-28 |
| WO2015075733A3 WO2015075733A3 (en) | 2015-12-17 |
Family
ID=53180343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2014/000655 WO2015075733A2 (en) | 2013-10-18 | 2014-10-16 | Polymerization of hydrocarbons |
Country Status (6)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201528379A (zh) * | 2013-12-20 | 2015-07-16 | Applied Materials Inc | 雙波長退火方法與設備 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857322A (en) * | 1954-04-28 | 1958-10-21 | Chemstrand Corp | Photopolymerization of acrylonitrile |
| US3859189A (en) * | 1968-01-14 | 1975-01-07 | Central De Chimie Fizica | Polymerization of acrylonitrile using radiation in the presence of dimethylsulphoxide and a protein |
| NL162087C (nl) * | 1970-04-21 | 1980-04-15 | Ceskoslovenska Akademie Ved | Werkwijze voor het polymeriseren van monoalkenische monomeren op zichzelf of voor het copolymeriseren met andere onverzadigde verbindingen. |
| FR2200283B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-09-22 | 1979-01-26 | Toyo Soda Mfg Co Ltd | |
| US4325794A (en) * | 1980-06-02 | 1982-04-20 | Calgon Corporation | Combined visible light and thermally activated continuous polymerization process |
| US4517063A (en) * | 1984-02-13 | 1985-05-14 | The Standard Oil Company | Photochemical reactor and method for carrying out photochemical reactions therein |
| JP2692194B2 (ja) | 1988-11-14 | 1997-12-17 | 日本合成ゴム株式会社 | 水素化ブロック共重合体及びその組成物 |
| US5149895A (en) * | 1990-01-16 | 1992-09-22 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5187236A (en) * | 1990-01-16 | 1993-02-16 | Mobil Oil Corporation | Solid block and random elastomeric copolymers |
| USH1786H (en) * | 1993-07-12 | 1999-02-02 | Shell Oil Company | Process for radiation cured conjugated diene-vinyl aromatic hydrocarbon block copolymers |
| WO2002055565A1 (fr) * | 2001-01-15 | 2002-07-18 | Kaneka Corporation | Procede et appareil pour produire une resine chloree de chlorure de vinyle |
| GB2396331A (en) * | 2002-12-20 | 2004-06-23 | Inca Digital Printers Ltd | Curing ink |
| US7524889B2 (en) * | 2006-07-06 | 2009-04-28 | Bisco, Inc. | Light emitting diode curable acrylates with reduced yellowing |
| CN102181001B (zh) * | 2011-03-11 | 2013-01-23 | 北京化工大学 | 一种可控/活性自由基聚合方法 |
| EP2778180B1 (en) * | 2011-11-07 | 2017-03-29 | Kaneka Corporation | Method for producing chlorinated vinyl chloride resin |
-
2014
- 2014-10-16 IN IN3272MU2013 patent/IN2013MU03272A/en unknown
- 2014-10-16 EP EP14863811.7A patent/EP3058000A4/en not_active Withdrawn
- 2014-10-16 CN CN201811130106.8A patent/CN109651535A/zh active Pending
- 2014-10-16 CN CN201480057162.7A patent/CN105658680A/zh active Pending
- 2014-10-16 JP JP2016524464A patent/JP6598770B2/ja active Active
- 2014-10-16 US US15/029,957 patent/US9969825B2/en active Active
- 2014-10-16 WO PCT/IN2014/000655 patent/WO2015075733A2/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| EP3058000A4 (en) | 2017-04-05 |
| CN109651535A (zh) | 2019-04-19 |
| WO2015075733A3 (en) | 2015-12-17 |
| EP3058000A2 (en) | 2016-08-24 |
| CN105658680A (zh) | 2016-06-08 |
| JP6598770B2 (ja) | 2019-10-30 |
| US20160244541A1 (en) | 2016-08-25 |
| US9969825B2 (en) | 2018-05-15 |
| IN2013MU03272A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-07-17 |
| JP2016533419A (ja) | 2016-10-27 |
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