CA2260782A1 - Production of cellulose carbamate - Google Patents
Production of cellulose carbamate Download PDFInfo
- Publication number
- CA2260782A1 CA2260782A1 CA002260782A CA2260782A CA2260782A1 CA 2260782 A1 CA2260782 A1 CA 2260782A1 CA 002260782 A CA002260782 A CA 002260782A CA 2260782 A CA2260782 A CA 2260782A CA 2260782 A1 CA2260782 A1 CA 2260782A1
- Authority
- CA
- Canada
- Prior art keywords
- cellulose
- urea
- pressure
- mixture
- liquid ammonia
- 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.)
- Abandoned
Links
- 229920002678 cellulose Polymers 0.000 title claims abstract description 151
- 239000001913 cellulose Substances 0.000 title claims abstract description 151
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 132
- 239000004202 carbamide Substances 0.000 claims abstract description 107
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 106
- 238000000034 method Methods 0.000 claims abstract description 76
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 238000006053 organic reaction Methods 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000004880 explosion Methods 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000008096 xylene Substances 0.000 claims description 10
- 239000002360 explosive Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920001131 Pulp (paper) Polymers 0.000 claims description 3
- 238000002441 X-ray diffraction Methods 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000009736 wetting Methods 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 description 42
- 239000000243 solution Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000005470 impregnation Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GWUSZQUVEVMBPI-UHFFFAOYSA-N nimetazepam Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWUSZQUVEVMBPI-UHFFFAOYSA-N 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000009827 uniform distribution Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101150105088 Dele1 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B1/00—Preparatory treatment of cellulose for making derivatives thereof, e.g. pre-treatment, pre-soaking, activation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19628277A DE19628277C2 (de) | 1996-07-12 | 1996-07-12 | Verfahren zur Aktivierung eines Cellulose und Harnstoff enthaltenden Gemisches, aktiviertes Cellulose und Harnstoff enthaltendes Gemisch und Verwendung des aktivierten Gemisches zur Herstellung von Cellulosecarbamat |
| DE19628277.2 | 1996-07-12 | ||
| PCT/EP1997/003593 WO1998002464A1 (de) | 1996-07-12 | 1997-07-08 | Cellulosecarbamatherstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2260782A1 true CA2260782A1 (en) | 1998-01-22 |
Family
ID=7799739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002260782A Abandoned CA2260782A1 (en) | 1996-07-12 | 1997-07-08 | Production of cellulose carbamate |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0910585A1 (cs) |
| JP (1) | JP2000505135A (cs) |
| AU (1) | AU3443497A (cs) |
| BR (1) | BR9710297A (cs) |
| CA (1) | CA2260782A1 (cs) |
| CZ (1) | CZ4199A3 (cs) |
| DE (1) | DE19628277C2 (cs) |
| PL (1) | PL331046A1 (cs) |
| TR (1) | TR199900025T2 (cs) |
| WO (1) | WO1998002464A1 (cs) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19715617A1 (de) * | 1997-04-15 | 1998-10-22 | Zimmer Ag | Verfahren für die modifizierte Herstellung von Cellulosecarbamat |
| DE19742692A1 (de) * | 1997-09-26 | 1999-04-01 | Rhodia Acetow Ag | Verfahren zur Aktivierung von Polysacchariden |
| EP1066109A1 (de) | 1998-03-13 | 2001-01-10 | Rhodia Acetow GmbH | Vorrichtung, verfahren und druckreaktor zur behandlung von feststoffen mit verflüssigten gasen unter druck |
| DE19814137A1 (de) * | 1998-03-30 | 1999-10-14 | Rhodia Acetow Ag | Verfahren zum Austreiben von Ammoniak aus einem aktivierten Polysaccharid |
| DE19835688A1 (de) * | 1998-08-07 | 2000-02-10 | Piesteritz Stickstoff | Verfahren zur Herstellung von Cellulosecarbamat |
| DE10023753A1 (de) * | 2000-05-15 | 2001-11-29 | Zimmer Ag | Verfahren und Vorrichtung zur Behandlung von Zellstoff mit Harnstoff und Ammoniak |
| DE10223171A1 (de) * | 2002-05-24 | 2003-12-11 | Zimmer Ag | Verfahren zur Herstellung von Cellulosecarbamat |
| DE10223172B4 (de) * | 2002-05-24 | 2004-05-06 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Herstellung von Cellulosecarbamat mittels reaktiver Extrusion und die Verwendung der Verfahrensprodukte zur Herstellung von Formkörpern |
| JP2019001876A (ja) * | 2017-06-14 | 2019-01-10 | 国立大学法人京都大学 | 微細セルロース繊維、その製造方法、スラリー及び複合体 |
| JP7340195B2 (ja) * | 2017-06-14 | 2023-09-07 | 国立大学法人京都大学 | 微細セルロース繊維、その製造方法、スラリー及び複合体 |
| JP7088888B2 (ja) * | 2019-08-29 | 2022-06-21 | 大王製紙株式会社 | 繊維状セルロース複合樹脂の製造方法 |
| FI129441B (en) * | 2019-11-20 | 2022-02-28 | Andritz Oy | Method for producing cellulose carbamate |
| FI20215213A1 (en) * | 2021-02-26 | 2022-08-27 | Infinited Fiber Company Oy | Process for the production of cellulose carbamate |
| JP7213296B2 (ja) * | 2021-03-31 | 2023-01-26 | 大王製紙株式会社 | 繊維状セルロース含有物、繊維状セルロース複合樹脂、及び繊維状セルロース含有物の製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2290888A (en) * | 1932-01-30 | 1942-07-28 | North American Rayon Corp | Cellulose activated by liquid ammonia |
| FI62318C (fi) * | 1981-01-27 | 1982-12-10 | Neste Oy | Foerfarande foer framstaellning av ett alkaliloesligt cellulosaderivat |
| US4600590A (en) * | 1981-10-14 | 1986-07-15 | Colorado State University Research Foundation | Method for increasing the reactivity and digestibility of cellulose with ammonia |
| JPS62236802A (ja) * | 1986-04-08 | 1987-10-16 | Asahi Chem Ind Co Ltd | アルカリ可溶性セルロ−スの製造方法 |
| DE4242437C2 (de) * | 1992-12-16 | 1998-08-13 | Zimmer Ag | Verfahren zur Herstellung von Cellulosecarbamat und Verwendung des erhaltenen Cellulosecarbamats zur Bildung einer Lösung für die Herstellung von Celluloseregenerat-Produkten |
| DE4329937C1 (de) * | 1993-09-04 | 1994-11-24 | Rhodia Ag Rhone Poulenc | Verfahren zur Behandlung von Cellulose zu deren Aktivierung für nachfolgende chemische Reaktionen |
| HUP9802337A3 (en) * | 1995-03-25 | 1999-03-29 | Rhodia Ag Rhone Poulenc | Process for activating polysaccharides, polysaccharides produced by this process, and use thereof |
-
1996
- 1996-07-12 DE DE19628277A patent/DE19628277C2/de not_active Expired - Fee Related
-
1997
- 1997-07-08 CA CA002260782A patent/CA2260782A1/en not_active Abandoned
- 1997-07-08 CZ CZ9941A patent/CZ4199A3/cs unknown
- 1997-07-08 WO PCT/EP1997/003593 patent/WO1998002464A1/de not_active Application Discontinuation
- 1997-07-08 BR BR9710297A patent/BR9710297A/pt unknown
- 1997-07-08 JP JP10505577A patent/JP2000505135A/ja active Pending
- 1997-07-08 AU AU34434/97A patent/AU3443497A/en not_active Abandoned
- 1997-07-08 EP EP97930510A patent/EP0910585A1/de not_active Withdrawn
- 1997-07-08 PL PL97331046A patent/PL331046A1/xx unknown
- 1997-07-08 TR TR1999/00025T patent/TR199900025T2/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ4199A3 (cs) | 1999-05-12 |
| JP2000505135A (ja) | 2000-04-25 |
| DE19628277C2 (de) | 1998-07-09 |
| PL331046A1 (en) | 1999-06-21 |
| TR199900025T2 (xx) | 1999-04-21 |
| BR9710297A (pt) | 1999-08-17 |
| EP0910585A1 (de) | 1999-04-28 |
| AU3443497A (en) | 1998-02-09 |
| WO1998002464A1 (de) | 1998-01-22 |
| DE19628277A1 (de) | 1998-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |