diff --git a/rustminify/src/lib.rs b/rustminify/src/lib.rs
index 6714f4c..6fd30c7 100644
--- a/rustminify/src/lib.rs
+++ b/rustminify/src/lib.rs
@@ -112,8 +112,15 @@ pub fn minify_tokens(tokens: TokenStream) -> String {
                     st = State::None;
                 }
                 TokenTree::Ident(ident) => {
-                    match mem::replace(&mut st, State::AlnumUnderscoreQuote) {
-                        State::AlnumUnderscoreQuote => *acc += " ",
+                    match mem::replace(
+                        &mut st,
+                        if ident.to_string().contains('#') {
+                            State::PoundIdent
+                        } else {
+                            State::AlnumUnderscoreQuote
+                        },
+                    ) {
+                        State::AlnumUnderscoreQuote | State::PoundIdent => *acc += " ",
                         State::PunctChars(puncts, _, _) => *acc += &puncts,
                         _ => {}
                     }
@@ -131,7 +138,7 @@ pub fn minify_tokens(tokens: TokenStream) -> String {
                         (&*literal, State::AlnumUnderscoreQuote)
                     };
                     match mem::replace(&mut st, next) {
-                        State::AlnumUnderscoreQuote => *acc += " ",
+                        State::AlnumUnderscoreQuote | State::PoundIdent => *acc += " ",
                         State::PunctChars(puncts, _, _) => *acc += &puncts,
                         _ => {}
                     }
@@ -185,6 +192,14 @@ pub fn minify_tokens(tokens: TokenStream) -> String {
                             *spacing = punct.spacing();
                         }
                     } else {
+                        match &st {
+                            State::AlnumUnderscoreQuote => {
+                                if "#\"'".contains(punct.as_char()) {
+                                    *acc += " ";
+                                }
+                            }
+                            _ => {}
+                        }
                         st = State::PunctChars(
                             punct.as_char().to_string(),
                             cur_pos,
@@ -206,6 +221,7 @@ pub fn minify_tokens(tokens: TokenStream) -> String {
         enum State {
             None,
             AlnumUnderscoreQuote,
+            PoundIdent,
             PunctChars(String, LineColumn, Spacing),
         }
     }
@@ -338,6 +354,7 @@ pub fn remove_docs(mut file: File) -> File {
 
 #[cfg(test)]
 mod tests {
+    use core::str::FromStr;
     use proc_macro2::TokenStream;
     use quote::{quote, ToTokens as _};
     use syn::{parse_quote, File};
@@ -354,6 +371,32 @@ mod tests {
     #[test_case(quote!(x | || ())                             => "x| ||()"                        ; "zero_arg_closure"      )]
     #[test_case(quote!(println!("{}", 2 * 2 + 1))             => r#"println!("{}",2*2+1)"#        ; "println"               )]
     #[test_case(quote!(macro_rules! m { ($($_:tt)*) => {}; }) => "macro_rules!m{($($_:tt)*)=>{};}"; "macro_rules"           )]
+    // https://doc.rust-lang.org/reference/tokens.html#reserved-prefixes
+    #[test_case(
+        quote!(fn x(a: &'a u8[]) -> impl 'a + Clone {}) =>
+        "fn x(a:&'a u8[])->impl 'a+Clone{}";
+        "impl_lifetime"
+    )]
+    #[test_case(
+        quote!(match "a" { _ => false}) =>
+        r#"match "a"{_=>false}"#;
+        "match_str_literal"
+    )]
+    #[test_case(
+        quote!('s: loop { loop { break 's; }}) =>
+        "'s:loop{loop{break 's;}}";
+        "break_label"
+    )]
+    #[test_case(
+        TokenStream::from_str("macro_rules! m { ($($_:tt)*) => {} } m!{ a # foo }").unwrap() =>
+        "macro_rules!m{($($_:tt)*)=>{}}m!{a #foo}";
+        "macro_punct_pound"
+    )]
+    #[test_case(
+        TokenStream::from_str("macro_rules! m { ($($_:tt)*) => {} } m!{ r#let # foo }").unwrap() =>
+        "macro_rules!m{($($_:tt)*)=>{}}m!{r#let#foo}";
+        "macro_rawident_punct_pound"
+    )]
     fn minify_tokens(tokens: TokenStream) -> String {
         crate::minify_tokens(tokens)
     }