US1794126A - Method of producing acetyl cellulose - Google Patents
Method of producing acetyl cellulose Download PDFInfo
- Publication number
- US1794126A US1794126A US155332A US15533226A US1794126A US 1794126 A US1794126 A US 1794126A US 155332 A US155332 A US 155332A US 15533226 A US15533226 A US 15533226A US 1794126 A US1794126 A US 1794126A
- Authority
- US
- United States
- Prior art keywords
- cellulose
- bath
- water
- acetic acid
- producing acetyl
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title description 9
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 title description 4
- 229940081735 acetylcellulose Drugs 0.000 title description 3
- 229920002301 cellulose acetate Polymers 0.000 title description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 229920002678 cellulose Polymers 0.000 description 14
- 239000001913 cellulose Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 230000000397 acetylating effect Effects 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 230000021736 acetylation Effects 0.000 description 5
- 238000006640 acetylation reaction Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000012345 acetylating agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HRSANNODOVBCST-UHFFFAOYSA-N Pronethalol Chemical compound C1=CC=CC2=CC(C(O)CNC(C)C)=CC=C21 HRSANNODOVBCST-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MROAQUNKLFXYQN-UHFFFAOYSA-N methanamine;sulfuric acid Chemical compound NC.OS(O)(=O)=O MROAQUNKLFXYQN-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/06—Cellulose acetate, e.g. mono-acetate, di-acetate or tri-acetate
Definitions
- Our invention relates to a method of producing acetyl cellulose compounds.
- ing solution is viscosity.
- a high degree of viscosity of the spinning solution generally results in the filaments to be produced therefrom being very strong; the lustre is also improved by an increased viscosity and spinning takes place more easily.
- the method according to our invention is characterized in this that before acetylation, the water content of the acetylating bath or of the catalyst (s) to be used in the acetylation or of both is adjusted exactly in accordof the desired final water and water vapour being excluded.
- our invention comprises a method whereby the acetylating bath either previously treated in the manner referred to or without preliminary treatment, is mixed With the catalyst (s), and thereupon left standing for some time with the exclusion of Water and water vapour.
- acetylating-bath When reference is made in the specification and claims to acetylating-bath this is to be understood asthe actual acetylating agent, such as for instance acetic anhydride mixed with suitable diluents, such as glacial acetic acid and the like.
- the catalysts in question are: sulphuric acid, sulphury-l chloride, methylamine sulphate and other substances usually employed as well as mixtures of two or more of these substances.
- cellulose includes, besides cellulose, alsocellulose hydrate and other near con- 1 version products of cellulose such as. commonly in use in the artificial silk industry.
- the method according to. our invention is carried out in such a manner that the acetyl-atingagent is practically entirely anhydrous, before the same is caused to act upon the cellulose, it is possible by correctly choosing th'e'water content of the cellulose employed to control the acetylation"reaction to a very definite extent and consequently to control to a greater extent the nature of the resulting final products.
- the cellulose used can consist of the materials usual for this purpose and may be subjected if desired to a preliminary treatment.
- Ewample I 4 kg. acetic anhydride are mixed-with L5 kg. glacial acetic acid'and this mixture is left standing for about 6 hours. 60 g. sulphuryl chloride are'then added as condensation agent, whereupon the'mixture is allowed to stand again for a few hours, care being taken, as in the first instance, that water or water vapour is excluded. 1 kg. cellulose having a moisture content of 6% is then immersed in the mixture produced in the manner referred to. The acetylation-takes place at 60 C. and requires about 6 hours.
- the solution produced in this way is worked up in a known manner, either by precipitatingthe resulting cellulose compound, dissolving in a volatile solvent and spinning in an atmosphere which may be heated if desired, or by directly spinning the solution in a suitable precipitating bath or by working up into plastic masses.
- acetyl cellul0se comprising providing an acetylizing bath consisting of acetic acid anhydride and glacial acetic acid, permltting said bath'to stand for several hours until a part of the As a general rule it Water in the acid has combined with the anhydride and subsequently introducing the cellulose into said bath.
- acetyl cellulose comprising providing an acetylizing bath-consisting of acetic acid anhydride and glacial acetic acid, permitting said bath to stand for several hours until a part of the water in the acid'has combined with the anhydride, then introducing a catalyzer and subsequently introducing the cellulose into said bath.
- the m-ethod'of producing acetyl cellulose comprising providing an acetylizing bath consisting of acetic acid anhydride and glacial acetic acid. pcrmitting said bath to stand for several hours until a part of the water inthc acid has cornbinedwith the anhydride, then introducinga catalyzer then allowing the bath to stand for several more hours and then introducing the. cellulose into sald bath.
Description
. ance with the viscosit product.
Patented Feb. 24, 1931 UNITED STATES PAT ENT o FIc SAMUEL rsrnoon YVLES AND LOUIS DE noor, or ARNHEM, NETH RLAN S, Assienons 'ro ALGEMEENE KUNSTZIJDE UNIE iv. v., or Anni- BM, NETHERLANDS METHOD OF PRODUCING ACETYL CELLULOSE No Drawing. Application filed December 16, 1926, Serial No. 155,332, 7 24, 1925. 1
Our invention relates to a method of producing acetyl cellulose compounds.
It is known that one of the most important requirements to be satisfied by a good spin: ing solution is viscosity. A high degree of viscosity of the spinning solution generally results in the filaments to be produced therefrom being very strong; the lustre is also improved by an increased viscosity and spinning takes place more easily.
Hitherto however for producing an increased viscosity attention has been concentrated almost exclusively upon the proportions in which the various constituents of the acetylating mixture are mixed and their quantity as well as that of the catalyst used has been adapted to suit the content of moisture in the cellulose.
After continued experiments We have found however that the desired object can be obtained in a much simpler manner, While the viscosity of the acetyl compounds can be more exactly controlled than is the case With the usual methods.
The method according to our invention is characterized in this that before acetylation, the water content of the acetylating bath or of the catalyst (s) to be used in the acetylation or of both is adjusted exactly in accordof the desired final water and water vapour being excluded.
Further, our invention comprises a method whereby the acetylating bath either previously treated in the manner referred to or without preliminary treatment, is mixed With the catalyst (s), and thereupon left standing for some time with the exclusion of Water and water vapour.
Finally it is possible according to our invention to cause the acetylating bath or acetylating mixture previously treated in the and. inthe-Netherlands December manner referred to, to act upon cellulose, the water content of which has been exactly adjusted beforehand.
When reference is made in the specification and claims to acetylating-bath this is to be understood asthe actual acetylating agent, such as for instance acetic anhydride mixed with suitable diluents, such as glacial acetic acid and the like. The catalysts in question are: sulphuric acid, sulphury-l chloride, methylamine sulphate and other substances usually employed as well as mixtures of two or more of these substances.
In thespecification and the claimsthe ex-v pression cellulose includes, besides cellulose, alsocellulose hydrate and other near con- 1 version products of cellulose such as. commonly in use in the artificial silk industry.
I By applying our inve'ntiomthe Water content oantherefore be regulated very exactly,
, hus resulting in very much improved ac'ety-- lation products and consequently-in, much better final products. According to our invention it is'possible to, prevent undesirable amounts of-wa-ter exerting upon the reaction an influence which causes the acetylation to adopt a definite course or produces by-reac: tions which are undesirable-forobtaining a satisfactory product. I
Moreover the valuable advantage is obtained that by employing our invention, slight variations in temperature have less detrimental results. This. again facilitates the acetyla-tion to a considerableeXt-ent and causes it to progress more regularly.
If the method according to. our invention is carried out in such a manner that the acetyl-atingagent is practically entirely anhydrous, before the same is caused to act upon the cellulose, it is possible by correctly choosing th'e'water content of the cellulose employed to control the acetylation"reaction to a very definite extent and consequently to control to a greater extent the nature of the resulting final products. The cellulose used can consist of the materials usual for this purpose and may be subjected if desired to a preliminary treatment.
The following examples give some .of the many Ways in which. our invention can be used; it is to be understood however, that several alterations may be applled Without departing from the scope of our invention.
Ewample I 4 kg. acetic anhydride are mixed-with L5 kg. glacial acetic acid'and this mixture is left standing for about 6 hours. 60 g. sulphuryl chloride are'then added as condensation agent, whereupon the'mixture is allowed to stand again for a few hours, care being taken, as in the first instance, that water or water vapour is excluded. 1 kg. cellulose having a moisture content of 6% is then immersed in the mixture produced in the manner referred to. The acetylation-takes place at 60 C. and requires about 6 hours. The solution produced in this way is worked up in a known manner, either by precipitatingthe resulting cellulose compound, dissolving in a volatile solvent and spinning in an atmosphere which may be heated if desired, or by directly spinning the solution in a suitable precipitating bath or by working up into plastic masses.
Ewample [I As a general rule the quantities of the acetic anhydride, glacial acetic acid and condensation agent, as Well as the moisture content of the cellulose and the time during which the mixture is left standing are chosen to correspond with the desired viscosity of the acetate solution. may be said that the greater-the desired viscosity the longer should the mixture be left standing. The most highly viscous solutions are produced When use is made of an acetylating bath which has been left standing for a very long time for instance 10 hours, so that practically the last traces of water in the acetic acid have combined with the acetic anhydride. As already mentioned in the foregoing, the viscosity of the products is of very great importance.
Themethod according to our invention which'enables the viscosity to be adjusted arbitrarily to an extremely exact degree is thereforeof greatest importance for the acetate silk indnstry. lVe claim:
'1. The method of producing acetyl cellul0se comprising providing an acetylizing bath consisting of acetic acid anhydride and glacial acetic acid, permltting said bath'to stand for several hours until a part of the As a general rule it Water in the acid has combined with the anhydride and subsequently introducing the cellulose into said bath.
2. The method of producing acetyl cellulose comprising providing an acetylizing bath-consisting of acetic acid anhydride and glacial acetic acid, permitting said bath to stand for several hours until a part of the water in the acid'has combined with the anhydride, then introducing a catalyzer and subsequently introducing the cellulose into said bath.
3. The m-ethod'of producing acetyl cellulosecomprising providing an acetylizing bath consisting of acetic acid anhydride and glacial acetic acid. pcrmitting said bath to stand for several hours until a part of the water inthc acid has cornbinedwith the anhydride, then introducinga catalyzer then allowing the bath to stand for several more hours and then introducing the. cellulose into sald bath. V
in testimony whereof we affix our signatures.
S. I. VLES. L. DE HOOP.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1794126X | 1925-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1794126A true US1794126A (en) | 1931-02-24 |
Family
ID=19873112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US155332A Expired - Lifetime US1794126A (en) | 1925-12-24 | 1926-12-16 | Method of producing acetyl cellulose |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1794126A (en) |
-
1926
- 1926-12-16 US US155332A patent/US1794126A/en not_active Expired - Lifetime
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